RD 147821
COMPOSITIONS FOR ARTICLES COMPRISING REPLICATED
MICROSTRUCTURES
BACKGROUND
The invention relates generally to curable (meth)acrylate compositions and, more
specifically ultraviolet (UV) radiation curable (meth)acrylate compositions. The
compositions are suitable for optical articles and particularly for light management
films.
In backlight computer displays or other display systems, optical films are commonly
used to direct light. For example, in backlight displays, light management films use
prismatic structures (often referred to as microstructure) to direct light along a
viewing axis (i.e., an axis substantially normal to the display). Directing the light
enhances the brightness of the display viewed by a user and allows the system to
consume less power in creating a desired level of on-axis illumination. Films for
turning or directing light can also be used in a wide range of other optical designs,
such as for projection displays, traffic signals, and illuminated signs. Ultraviolet
radiation curable (meth)acrylate compositions find use in applications such as display
systems. Films for light management applications are typically prepared by curing a
composition in common molds, such as nickel or nickel/cobalt electroforms, into the
requisite shape.
In the preparation of light management films, the curable compositions employed tend
to stick to the molds used for microreplication. This results in poor replication,
roughened surfaces, buckling of the coating, and/or catastrophic loss of adhesion to
the carrier film and destruction of the mold. In addition, the product light
management films lack, in some instances, sufficient abrasion resistance to meet the
requirements of a particular application. There remains a continuing need for further
improvement in the materials used to make them, particularly materials that upon
curing possess the combined attributes desired to satisfy the increasingly exacting
requirements for light management film applications.
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RD 147821
BRIEF DESCRIPTION
In one aspect, the present invention provides a curable composition comprising:
(a) at least one silicone containing surfactant, wherein the
surfactant is present in a range corresponding to from about 0.01 to about 5 weight
percent based upon the total weight of the composition;
(b) a least one multifunctional (meth)acrylate represented by the
structure 1

wherein R1 is hydrogen or methyl; X1 is O, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical; and optionally
(c) one or more nanoparticulate fillers.
In one embodiment, the present invention provides a curable composition comprising:
(a) at least one silicone containing surfactant, wherein the
surfactant is present in a range corresponding to from about 0.01 to about 5 weight
percent based upon the total weight of the composition;
(b) a multifunctional (meth)acrylate represented by the structure 1

wherein R is hydrogen or methyl; X1 is O, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical;
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RD 147821
(c) at least one monofunctional (meth)acrylate; and optionally
(d) one or more nanoparticulate fillers.
In an alternate embodiment, the present invention provides a curable composition
comprising
(a) at least one silicone containing surfactant, wherein the
surfactant is present in a range corresponding to from about 0.01 to about 5 weight
percent based upon the total weight of the composition;
(b) a multifunctional (meth)acrylate represented by the structure I;
(c) at least one monofunctional (meth)acrylate having structure VI

wherein R10 is hydrogen or methyl; X2 and X3 are independently in each instance O,
S, or Se; R11 is a divalent C1-C20 aliphatic radical, a divalent C3-C20 cycloaliphatic
radical, or a divalent C3-C20 aromatic radical; and Ar is monovalent C3-C20 aromatic
radical; and optionally
(d) one or more nanoparticulate fillers.
In yet another embodiment another embodiment, the present invention provides a
curable composition comprising:
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RD 147821
(a) at least one silicone containing surfactant, wherein the
surfactant is present in a range corresponding to from about 0.01 to about 5 weight
percent based upon the total weight of the composition;
(b) a multifunctional (meth)acrylate represented by the structure IV

wherein R1 is hydrogen or methyl, and U is a bond, an oxygen atom, a sulfur atom, a
selenium atom, an SO2 group, an SO group, a CO group, a C1-C20 aliphatic radical,
C3-C20 cycloaliphatic radical, or a C3-C20 aromatic radical;
(c) at least one monofunctional (meth)acrylate having structure VI;
and optionally
(d) one or more nanoparticulate fillers.
In yet another embodiment, the present invention provides a cured composition
comprising:
(a) at least one silicone containing surfactant, wherein the
surfactant is present in a range corresponding to from about 0.01 to about 5 weight
percent based upon the total weight of the composition;
(b) structural units derived from at least one multifunctional
(meth)acrylate represented by the structure I; and optionally
(c) one or more nanoparticulate fillers.
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RD 147821
In yet another embodiment, the present invention provides a cured composition
comprising:
(a) at least one silicone containing surfactant, wherein the
surfactant is present in a range corresponding to from about 0,01 to about 5 weight
percent based upon the total weight of the composition;
(b) structural units derived from at least one multifunctional
(meth)acrylate represented by the structure I;
(c) structural units derived from at least one monofunctional
(meth)acrylate; and optionally
(d) one or more nanoparticulate fillers.
In various aspects and embodiments, the present invention provides an article
comprising the cured compositions comprising of the invention. In certain
embodiments, the articles provided by the present invention arc useful as light
management films.
DETAILED DESCRIPTION
Approximating language, as used herein throughout the specification and claims, may
be applied to modify any quantitative representation that could permissibly vary
without resulting in a change in the basic function to which it is related. Accordingly,
a value modified by a term or terms, such as "about" and "substantially", are not to be
limited to the precise value specified. In at least some instances, the approximating
language may correspond to the precision of an instrument for measuring the value.
Here and throughout the specification and claims, range limitations may be combined
and/or interchanged, such ranges are identified and include all the sub-ranges
contained therein unless context or language indicates otherwise.
The present invention may be understood more readily by reference to the following
detailed description of preferred embodiments of the invention and the examples
included therein. In the following specification and the claims which follow, reference
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RD 147821
will be made to a number of terms which shall be defined to have the following
meanings.
The singular forms "a", "an" and "the" include plural referents unless the context
clearly dictates otherwise.
As used herein, the term "integer" is defined to be any whole number including zero.
"Optional" or "optionally" means that the subsequently described event or
circumstance may or may not occur, and that the description includes instances where
the event occurs and instances where it does not.
As used herein, the term "nanoparticulate filler" includes functionalized
nanoparticulate fillers and unfunctionalized nanoparticulate fillers.
As used herein, he expression "one or more" includes the meaning of the term "at
least one". Thus, with reference to a composition, the expression "optionally
comprising one or more nanoparticulate fillers" describes compositions devoid of
even a single nanoparticulate filler, and also describes compositions comprising at
least one nanoparticulate filler. The expression "optionally comprising one or more
nanoparticulate fillers" is at times herein used in preference to the expression
"optionally comprising at least one nanoparticulate fillers" for stylistic reasons.
As used herein, the term "aromatic radical" refers to an array of atoms having a
valence of at least one comprising at least one aromatic group. The array of atoms
having a valence of at least one comprising at least one aromatic group may include
heteroatoms such as nitrogen, sulfur, selenium, silicon and oxygen, or may be
composed exclusively of carbon and hydrogen. As used herein, the term "aromatic
radical" includes but is not limited to phenyl, pyridyl, furanyl, thienyl naphthyl,
phenylenc, and biphenyl radicals. As noted, the aromatic radical contains at least one
aromatic group. The aromatic group is invariably a cyclic structure having 4n+2
"delocalized" electrons where "n" is an integer equal to 1 or greater, as illustrated by
phenyl groups (n = 1), thienyl groups (n = 1), furanyl groups (n = 1), naphthyl groups
(n = 2), azulcnyl groups (n = 2), anthraceneyl groups (n = 3) and the like. The
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RD 147821
aromatic radical may also include nonaromatic components. For example, a benzyl
group is an aromatic radical which comprises a phenyl ring (the aromatic group) and a
methylene group (the nonaromatic component). Similarly a tetrahydronaphthyl radical
is an aromatic radical comprising an aromatic group (C6H3) fused to a nonaromatic
component -(CH2)4- For convenience, the term "aromatic radical" is defined herein
to encompass a wide range of functional groups such as alkyl groups, alkenyl groups,
alkynyl groups, haloalkyl groups, haloaromatic groups, conjugated dienyl groups,
alcohol groups, ether groups, aldehydes groups, ketone groups, carboxylic acid
groups, acyl groups (for example carboxylic acid derivatives such as esters and
amides), amine groups, nitro groups, and the like. For example, the 4-methylphenyl
radical is a C7 aromatic radical comprising a methyl group, the methyl group being a
functional group which is an alkyl group. Similarly, the 2-nitrophenyl group is a C6
aromatic radical comprising a nitro group, the nitro group being a functional group.
Aromatic radicals include halogenated aromatic radicals such as 4-
trifluoromethylphenyl, hexafluoroisopropylidenebis(4-phen-l-yloxy) (i.e., -
OPhC(CF3)2PhO-), 4-chloromethylphen-l-yl, 3-trifluorovinyl-2-thienyl, 3-
trichloromethylphen-1-yl (i.e., 3-CCl3Ph-), 4-(3-bromoprop-l-yl)phen-l-yl (i.e., 4-
BrCH2CH2CH2Ph-), and the like. Further examples of aromatic radicals include 4-
allyloxyphcn-1-oxy, 4-aminophen-]-yl (i.e., 4-H2NPh-), 3-aminocarbonylphen-l-yl
(i.e., NH2COPh-), 4-benzoylphen-l-yl, dicyanomethylidenebis(4-phen-l-yloxy) (i.e.,
-OPhC(CN)2PhO-), 3-methylphen-l-yl, methylenebis(4-phen-l-yloxy) (i.e., -
OPhCH2PhO-), 2-ethylphen-l-yl, phenylcthenyl, 3-forrny]-2-thienyl, 2-hexyl-5-
furanyl, hexamethylene-l,6-bis(4-phen-l-yloxy) (i.e., -OPh(CH2)6PhO-), 4-
hydroxymethylphen-1-yl (i.e., 4-HOCH2Ph-), 4-mercaptomethylphen-l-yl (i.e., 4-
HSCH2Ph-), 4-methylthiophen-l-yl (i.e., 4-CH3SPh-), 3-methoxyphen-l-yl, 2-
methoxycarbonylphen-1-yloxy (e.g., methyl salicyl), 2-nitromethylphen-l-yl (i.e., 2-
NO2CH2Ph), 3-trimethylsilylphen-l-yl, 4-t-butyldimethylsilylphenl-l-yl, 4-vinylphen-
1-yl, vinylidenebis(phenyl), and the like. The term "a C3 - C10 aromatic radical"
includes aromatic radicals containing at least three but no more than 10 carbon atoms.
The aromatic radical 1-imidazolyl (C3H2N2-) represents a C3 aromatic radical. The
benzyl radical (C7H7-) represents a C7 aromatic radical.
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RD 147821
As used herein the term "cycloaliphatic radical" refers to a radical having a valence of
at least one, and comprising an array of atoms which is cyclic but which is not
aromatic. As defined herein a "cycloaliphatic radical" does not contain an aromatic
group. A "cycloaliphatic radical" may comprise one or more noncyclic components.
For example, a cyclohexylmethyl group (C6H11CH2) is an cycloaliphatic radical
which comprises a cyclohexyl ring (the array of atoms which is cyclic but which is
not aromatic) and a methylene group (the noncyclic component). The cycloaliphatic
radical may include heteroatoms such as nitrogen, sulfur, selenium, silicon and
oxygen, or may be composed exclusively of carbon and hydrogen. For convenience,
the term "cycloaliphatic radical" is defined herein to encompass a wide range of
functional groups such as alky] groups, alkenyl groups, alkynyl groups, haloalkyl
groups, conjugated dienyl groups, alcohol groups, ether groups, aldehyde groups,
ketone groups, carboxylic acid groups, acyl groups (for example carboxylic acid
derivatives such as esters and amides), amine groups, nitro groups, and the like. For
example, the 4-methylcyclopent-l-yl radical is a C6, cycloaliphatic radical comprising
a methyl group, the methyl group being a functional group which is an alkyl group.
Similarly, the 2-nitrocyclobut-l-yl radical is a C4 cycloaliphatic radical comprising a
nitro group, the nitro group being a functional group. A cycloaliphatic radical may
comprise one or more halogen atoms which may be the same or different. Halogen
atoms include, for example; fluorine, chlorine, bromine, and iodine. Cycloaliphatic
radicals comprising one or more halogen atoms include 2-trifluoromethylcyclohex-l-
yl, 4-bromodifluoromethylcyclooct-1 -yl, 2-chlorodifluoromethylcyclohex-1 -yl,
hexafluoroisopropylidene-2,2-bis (cyclohex-4-yl) (i.e., -C6H10C(CF3)2 C6H10-), 2-
chloromethylcyclohex-1-yl, 3- difluoromethylenecyclohex-1-yl, 4-
trichloromethylcyclohex-1-yloxy, 4-bromodichloromethylcyclohex-1 -ylthio, 2-
bromoethylcyclopent-1-yl, 2-bromopropylcyclohex-l-yloxy (e.g.,
CH3CHBrCH2C6H10O-), and the like. Further examples of cycloaliphatic radicals
include 4-allyloxycyclohex-l-yI, 4-aminocyclohex-l-yl (i.e., H2NC6H10-), 4-
aminocarbonylcyclopent-1-yl (i.e., NH2COC5H8-), 4-acetyloxycyclohex-l-yl, 2,2-
dicyanoisopropylidenebis(cyclohex-4-yloxy) (i.e., -OC6H10C(CN)2C6H10O-), 3-
methylcyclohex-1-yl, methylenebis(cyclohex-4-yloxy) (i.e., -OC6H10CH2CH10O-),
1 -ethylcyclobut-1 -yl, cyclopropylethenyl, 3-formyl-2-tcrahydrofuranyl, 2-hexyl-5-
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RD 147821
tetrahydrofuranyl, hexamethylene-l,6-bis(cyclohex-4-yloxy) (i.e., -O
C6H10(CH2)6C6H10O-), 4-hydroxymcthylcyclohex-l-yl (i.e., 4-HOCH2C6H10-), 4
mercaptomcthylcyclohex-1-yl (i.e., 4-HSCH2C6U10-), 4-methylthiocyclohex-l-yl (i.e.,
4-CH3SC6H10-), 4-methoxycyclohex-l-yl, 2-methox.ycarbonylcyclohex-l-yloxy (2-
CH3OCOC6H10O-), 4-nitromethylcyclohex-l-yl (i.e., N02CH2C6H10-), 3-
trimethylsilylcyclohex-1-yl, 2-t-butyldimethylsilylcyclopent-l-yl, 4-
trimethoxysilylethylcyclohex-1-yl (e.g., (CH30)3SiCH2CH2C6H10-), 4-
vinylcyclohexen-1-yl, vinylidenebis(cyclohexyl), and the like. The term "a C3 - C10
cycloaliphatic radical" includes cycloaliphatic radicals containing at least three but
no more than 10 carbon atoms. The cycloaliphatic radical 2-tctrahydrofuranyl
(C4H7O-) represents a C4 cycloaliphatic radical. The cyclohexylmethyl radical
(C6H11CH2-) represents a C7 cycloaliphatic radical.
As used herein the term "aliphatic radical" refers to an organic radical having a
valence of at least one consisting of a linear or branched array of atoms which is not
cyclic. Aliphatic radicals are defined to comprise at least one carbon atom. The array
of atoms comprising the aliphatic radical may include heteroatoms such as nitrogen,
sulfur, silicon, selenium and oxygen or may be composed exclusively of carbon and
hydrogen. For convenience, the term "aliphatic radical" is defined herein to
encompass, as part of the "linear or branched array of atoms which is not cyclic" a
wide range of functional groups such as alkyl groups, alkenyl groups, alkynyl groups,
haloalkyl groups , conjugated dienyl groups, alcohol groups, ether groups, aldehyde
groups, ketone groups, carboxylic acid groups, acyl groups (for example carboxylic
acid derivatives such as esters and amides), amine groups, nitro groups, and the like.
For example, the 4-methylpent-l-yl radical is a C6 aliphatic radical comprising a
methyl group, the methyl group being a functional group which is an alkyl group.
Similarly, the 4-nitrobut-l-yl group is a C4 aliphatic radical comprising a nitro group,
the nitro group being a functional group. An aliphatic radical may be a haloalkyl
group which comprises one or more halogen atoms which may be the same or
different. Halogen atoms include, for example; fluorine, chlorine, bromine, and
iodine. Aliphatic radicals comprising one or more halogen atoms include the alkyl
halides trifluoromethyl, bromodifluoromethyl, chlorodifluoromethyl,
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RD 147821
hexafluoroisopropylidcne, chloromethyl, difluorovinylidene, trichloromethyl,
bromodichloromcthyl, bromoethyl, 2-bromotrirnethylene (e.g., -CH2CHBrCH2-), and
the like. Further examples of aliphatic radicals include allyl, aminocarbonyl (i.e.. -
CONH2), carbonyl, 2,2-dicyanoisopropylidenc (i.e., -CH2C(CN)2CH2-), methyl (i.e., -
CH3), methylene (i.e., -CH2-), ethyl, ethylene, formyl (i.e.,-CHO), hexyl,
hexamethylene, hydroxymethyl (i.c.,-CH2OH), mercaptomethyl (i.e., --CH2SH),
methylthio (i.e., -SCH3), methylthiomethyl (i.e., -CH2SCH3), methoxy,
methoxycarbonyl (i.e., CH3OCO-) , nitromethyl (i.e., -CH2NO2). thiocarbonyl,
trimethylsilyl ( i.e., (CH3)3Si-), t-butyldimethylsilyl, 3-tnmcthyoxysilypropyl (i.e.,
(CH3O)3SiCH2CH2CH2-), vinyl, vinylidene, and the like. By way of further
example, a C1 - C10 aliphatic radical contains at least one but no more than 10 carbon
atoms. A methyl group (i.e., CH3-) is an example of a C| aliphatic radical. A decyl
group (i.e., CH3(CH2)9-) is an example of a C10 aliphatic radical.
The phrase "(meth)acrylate monomer" refers to any of the monomers comprising at
least one acrylate unit, wherein the substitution of the double bonded carbon adjacent
to the carbonyl group is either a hydrogen or a methyl substitution. Examples of
"(meth)acylate monomers" include methyl methacrylate (CAS No. 80-62-6) where
the substitution on the double bonded carbon adjacent to the carbonyl group is a
methyl group, acrylic acid where the substitution on the double bonded carbon
adjacent to the carbonyl group is a hydrogen group, phenyl methacrylate where the
substitution on the double bonded carbon adjacent to the carbonyl group is a methyl
group, phenyl thioethyl methacrylate where the substitution on the double bonded
carbon adjacent to the carbonyl group is a methyl group, ethyl acrylate where the
substitution on the double bonded carbon adjacent to the carbonyl group is a hydrogen
group, 2,2-bis((4-(meth)acryloxy)phenyl)propane (CAS No. 3253-39-2, also known
as Bisphenol A dimethacrylate) where the substitution on the double bonded carbon
adjacent to the carbonyl group is a methyl group, Bisphenol A diglyciyl ether
dimethaerylate (CAS No. 1565-94-2) where the substitution on the double bonded
carbon adjacent to the carbonyl group is a methyl group, and the like.
This invention is related to a curable composition comprising at least one silicone
containing surfactant, at least one (meth)acrylate monomer, and optionally, one or
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RD 147821
more nanoparticulate fillers. Thus, in one embodiment, the presesent invention
provides a curable composition comprising at least one silicone containing surfactant,
and at least one (meth)acrylate monomer. In an alternate embodiment, the curable
composition further comprises at least one nanoparticulate filler.
In one aspect, the curable composition is a solvent-free, high refractive index,
radiation curable composition that provides a cured material having an excellent
balance of properties. The compositions are ideally suited for light management film
applications. In one aspect, light management films prepared from the curable
compositions exhibit excellent abrasion resistance.
As noted, in one embodiment, the present invention provides a curable composition
comprising (a) at least one silicone containing surfactant, wherein the surfactant is
present in a range corresponding to from about 0.01 to about 5 weight percent based
upon the total weight of the composition; and (b) a multifunctional (meth)acrylate
represented by the structure I

wherein R1 is hydrogen or methyl; X1 is O, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical, and optionally (c) one or more nanoparticulate fillers.
Thus, in one aspect, the curable composition provided by the present invention does
not require the presence of a monofunctional (meth)acrylate in order to provide a
useful curable composition, for example a composition which can be used in the
preparation of a light management film. In embodiments in which a monofunctional
(meth)acrylate is not required, the curable composition may comprise one or more
multifunctional (meth)acrylates. In one embodiment, the curable composition
comprises at least one multifunctional (meth)acrylatc selected from the group
consisting of aliphatic diol (meth)acrylates, cycloaliphatic diol (meth)acrylates, and
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aromatic diol (meth)acrylates. Aliphatic diol (meth)acrylatcs arc multifunctional
(meth)acrylates which may be prepared, for example, by reaction of an aliphatic diol
such as 1,6-hexanediol with (meth)acryloyl chloride. Cycloaliphatic diol
(ineth)acrylates are defined analogously and may be prepared in via methods known
to those skilled in the art from the corresponding aliphatic diol and (meth)acryloyl
chloride. Aromatic diol (meth)acrylates are likewise known to those skilled in the art
to be available by reaction of the corresponding aromatic diol with (meth)acryloyl
chloride and by other methods. Various mixtures of multifunctional (meth)acrylates
may be employed to provide useful curable compositions that may be used in the
preparation of cured articles such as light management films. In the disclosure which
follows, a wide variety of multifunctional (meth)acrylates arc described as suitable for
use in the curable compositions of the present invention. Such multifunctional
(meth)acrylates are also useful in the preparation of curable compositions which do
not comprise a monofunctional (meth)acrylate. Although much of the disclosure
which follows is directed to curable compositions comprising at least one
monofunctional (meth)acrylate, as will be recognized by those skilled in the art,
various aspects of the disclosed structures, compositions, and principles apply equally
in a number of embodiments to curable compositions not requiring the presence of a
monofunctional (meth)acrylatc. Thus, for example, in one embodiment the present
invention provides a curable composition comprising (a) at least one silicone
containing surfactant, wherein the surfactant is present in a range corresponding to
from about 0.01 to about 5 weight percent based upon the total weight of the
composition; (b) at least one multifunctional (meth)acrylate represented by the
structure I wherein R is a polyvalent aromatic radical having structure 111; and
optionally (c) one or more nanoparticulate fillers. In yet another embodiment, the
present invention provides a curable composition comprising (a) at least one silicone
containing surfactant, wherein the surfactant is present in a range corresponding to
from about 0.01 to about 5 weight percent based upon the total weight of the
composition; (b) at least one multifunctional (rneth)acrylate represented by the
structure IV; and optionally (c) one or more nanoparticulate fillers. In yet another
embodiment, the present invention provides a curable composition comprising (a) at
least one silicone containing surfactant, wherein the surfactant is present in a range
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RD 147821
corresponding to from about 0.01 to about 5 weight percent based upon the total
weight of the composition; (b) at least one multifunctional (meth)acrylate prepared by
the ring opening reaction of tetrabromobisphenol A diglycidyl ether with
(meth)acrylic acid; and optionally (c) one or more nanoparticulate filler-. In still yet
another embodiment, the present invention provides a cured composition comprising:
(a) at least one silicone containing surfactant, wherein the surfactant is present in a
range corresponding to from about 0.01 to about 5 weight percent based upon the total
weight of the composition; (b) structural units derived from at least one
multifunctional (mefh)acrylate having structure I; and optionally (c) one or more
nanoparticulate fillers. In still yet another embodiment, the present invention
provides a cured composition comprising (a) at least one silicone containing
surfactant, wherein the surfactant is present in a range corresponding to from about
0.01 to about 5 weight percent based upon the total weight of the composition; and (b)
structural units derived from at least one multifunctional (meth)acrylate represented
by the structure I wherein R is a polyvalent aromatic radical having structure III, and
optionally (c) one or more nanoparticulate fillers. In yet another embodiment, the
present invention provides a cured composition comprising (a) at least one silicone
containing surfactant, wherein the surfactant is present in a range corresponding to
from about 0.01 to about 5 weight percent based upon the total weight of the
composition; and (b) structural units derived from at least one multifunctional
(meth)acrylate represented by the structure IV; and optionally (c) one or more
nanoparticulate fillers. In yet another embodiment, the present invention provides a
cured composition comprising (a) at least one silicone containing surfactant, wherein
the surfactant is present in a range corresponding to from about 0.01 to about 5 weight
percent based upon the total weight of the composition; and (b) structural units
derived from at least one multifunctional (meth)acrylate prepared by the ring opening
reaction of tetrabromobisphenol A diglycidyl ether with (meth)acrylic acid; and
optionally (c) one or more nanoparticulate fillers.
Typically, the curable compositions of the present invention are liquids at room
temperature. In one embodiment, the curable composition of the present invention is
a low melting solid (i.e. the composition has a melting point of less than about 50"C).
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RD 147821
In yet another embodiment, the curable composition of the present invention has a
melting point of less than about 100°C. In an alternate embodiment, the curable
composition of the present invention is an amorphous solid having a softening point
of less than about 50°C.
The compositions of the present invention are "curable" in the sense that the
composition comprises as monomeric species, at least one multifunctional
(meth)acrylate and optionally at least one monofunctional (meth)acrylate, which when
subjected to curing conditions afford a cured, polymeric composition. Various curing
conditions may be employed to convert the curable compositions of the present
invention into the corresponding cured compositions. In one embodiment, the
composition is "curable" in the sense that it may converted into a cured, polymeric
composition upon exposure to ultraviolet (UV) radiation. The curable compositions
of the present invention in certain embodiments comprise a photo-active
polymerization initiator. Alternatively, the curable compositions of the present
invention may comprise a polymerization initiator which may be activated thermally,
for example 2,2'-bisazobisiosbutyronitrile (AIBN, CAS No. 78-67-1), 1,1'-
azobis(cyclohexanecarbonitrile), 4,4'azobis(4-cyanovaleric acid), 2,2'azobis(2-
methylproionamidine) dihydrochloride (CAS No. 2997-92-4), azo-tert-butane, and the
like. In one embodiment, the presence of a polymerization initiator is not required
and the curable composition may be polymerized by simply heating or irradiating.
In one embodiment, the curable composition of the present invention comprises a
peroxide polymerization initiator. Such peroxy-based initiators that may be used to
promote polymerization of the curable composition by thermal activation. Suitable
peroxide polymerization initiators include, for example, dibenzoyl peroxide, dicumyl
peroxide, methyl ethyl ketone peroxide, lauryl peroxide, cyclohexanone peroxide, t-
butyl hydroperoxide, t-butyl benzene hydroperoxide, t-butyl peroctoate, 2,5-
dimethylhexane-2,5-dihydroperoxide, 2,5-dimethyl-2,5-di(t-butylperoxy)-hex-3-yne,
di-t-butylperoxide, t-butylcumyl peroxide, alpha, alpha'-bis(t-butylperoxy-m-
isopropyl)benzene, 2,5-dimetbyl-2,5-di(t-butylperoxy)hexane, dicumylperoxide, di(t-
butylperoxy isophthalate, t-butylperoxybenzoatc, 2,2-bis(t-butylperoxy)butane, 2,2-
bis(t-butylperoxy)octane, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane,
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RD 147821
di(trimethylsilyl)pcroxide, trimethylsilylphenyltriphenylsilyl peroxide, and the like,
and combinations comprising at least one of the foregoing polymerization initiators.
In one embodiment, the curable composition of the present invention comprises a
photoinitiator which serves to promote the on-demand polymerization (curing) of the
(meth)acrylate components of the curable composition. Suitable polymerization
initiators include photoinitiators that promote polymerization of the components upon
exposure to ultraviolet radiation. Particularly suitable photoinitiators include
phosphine oxide photoinitiators. Examples of such photoinitiators include the
1RGACURE® and DAROCURTM series of phosphine oxide photoinitiators available
from CIBA SPECIALTY CHEMICALS; the LUCIRIN® series of photoinitiators
available from BASF Corp.; and the ESACURE®) series of photoinitiators. Other
useful photoinitiators include ketone-based photoinitiators, such as hydroxy- and
alkoxyalkyl phenyl ketones, and thioalkylphenyl morpholinoalkyl ketones. Also
suitable are benzoin ether photoinitiators.
In one embodiment, the curable composition of the present invention may comprise at
least one C10-C40 aliphatic acid. In certain instances, the C10-C40 aliphatic acid
component of the curable composition may prevent fouling of surfaces in contact with
the composition during polymerization (curing). Thus, for instance, during the
preparation of a light management film, such as a brightness enhancement film,
comprising surface microstructures the curable composition is contacted with an
electroforrn (also referred to as a "master", a "shim" or a "cast roll") comprising
surface features which will be replicated in the brightness enhancement film. In order
to replicate the microstructures of the electro form in the film, the curable composition
is polymerized (cured) while in contact with the electroforrn. After polymerization of
the curable composition, the cured composition comprising the microstructures
replicated from the microstructures on the surface of the electroform is disengaged
from (peeled from) the electroform. Typically, the cured composition is in the form
of a film. As successive mierostructure-containing film samples are prepared and
peeled from the electroform, fouling of the electroform may occur. In certain
embodiments, the presence of at least one aliphatic acid in the curable composition
prevents fouling of the electroform, and as a result, the electroform may be used to
15

RD 147821
prepare a greater number of film samples than could be prepared using a curable
composition lacking an aliphatic acid component.
In one embodiment, the C10-C40 aliphatic acid component is present in an amount
corresponding to from about 0.01 weight percent to about 1 weight percent based
upon a total weight of the composition. In an alternate embodiment, the C10-C40
aliphatic acid component is present in an amount corresponding to from about 0.05
weight percent to about 0.5 weight percent based upon a total weight of the
composition. In yet another embodiment, the C10-C40 aliphatic acid component is
present in an amount corresponding to from about 0.1 weight percent to about 0.4
weight percent based upon a total weight of the composition.
In one embodiment, the C10-C40 aliphatic acid component comprises a carboxylic acid
having structure II

wherein R3 is a C9-C39 aliphatic radical. Suitable aliphatic acid components include,
but are not limited to, naturally occurring and synthetic fatty acids such as palmitic-
acid, stearic acid, and myristic acid. In one embodiment, the aliphatic acid component
comprises at least one fatty acid selected from the group consisting of myristic acid,
palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and eicosanoic acid.
In an alternate embodiment, the aliphatic acid component comprises a synthetic C10-
C40 aliphatic acid which is not a fatty acid, for example alpha-hexadecyloxy acetic-
acid, alpha-hexadecylthio acetic acid, alpha-octadecyloxy acetic acid, and the like.
As noted, the curable composition of the present invention comprises at least one a
multifunctional (meth)acrylate represented by the structure I.
16

RD 147821

wherein R1 is hydrogen or methyl; X1 is O, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical. The term "multifunctional (meth)acrylate" means a
composition comprising at least two (meth)acryloyl groups, a (meth)acryloyl group
having the structure

wherein R1 is hydrogen or methyl and the dashed line (—) signals the point of
attachment of the (meth)acryloyl group to the multifunctional (meth)acrylatc.
As noted, the group R is a polyvalent aromatic radical. By "polyvalent aromatic
radical" it is meant that R2 possesses at least two points of attachment (valences) to
which (meth)acryloyl groups may be attached. In one embodiment, R2 is a divalent
aromatic radical to which may be attached two (meth)acryloyl groups. In an alternate
embodiment, R is a trivalent aromatic radical to which may be attached three
(meth)acryloyl groups. R2 is an aromatic radical within the definition of the term
"aromatic radical" given herein. As such, the group R2 comprises at least one
aromatic ring. By way of further example, in bisphenol A dimethacrylate, two
acryloyl groups are attached to an aromatic radical having the formula C15H14O2.
In one embodiment, R2 is a divalent aromatic radical having structure III

RD 147821

wherein and U is a bond, an oxygen atom, a sulfur atom, a selenium atom, an SO2
group, an SO group, a CO group, a C1-C20 aliphatic radical, C3-C20 cycloaliphatic
radical, or a C3-C20 aromatic radical; R4 is independently at each occurrence a halogen
atom, a nitro group, a cyano group, an amino group, a hydroxy group, a C1-C20
aliphatic radical, a C3-C20 cycloaliphatic radical, or a C3-C20 aromatic radical; R5 is
independently at each occurrence a hydrogen atom, a hydroxy group, a thiol group, or
an amino group; W is a bond, a divalent C1-C20 aliphatic radical, a divalent C3-C20
cycloaliphatic radical, a divalent C3-C20 aromatic radical; and "m" and "p" are
independently integers ranging from 0 to 4.
Suitable aromatic radicals represented by structure III are illustrated by Examples I-1,
1-2, 1-3, 1-4, and 1-5, in Table 1, in which the group R2 falls within the genus
encompassed by structure III. For instance, in Example 1-1 of Table 1, R2 represents
structure III wherein the group U is an isopropylidene group ((CH3)2C) the groups R4
represent bromine atoms, the values of "m" and "p" are each 2, the 4 bromine atoms
are located at the 2, 2', 6, and 6' positions of a bisphenol A residue, R5 is hydroxy
(OH), and "W" represents a methylene (CH2) group. To further illustrate the
relationship between structures I and III, attention is called to Example 1-1 of Table 1
wherein each of the terminal methylene groups (—CH2 or CH2—) shown in the
structure under the heading "R2" (the structure which illustrates generic formula 111)
serves as the point of attachment for the (meth)acryloyloxy groups


RD 147821
present in the di(meth)acrylate composition-represented by structure I wherein R1 is
methyl (Me), X1 is oxygen (O), and "n" = 2 .
TABLE 1 MULTIFUNCTIONAL (METH)ACRYLATES HAVING STRUCTURE I


RD 147821
In one embodiment, the multifunctional (meth)acrylate comprises at least one
di(meth)acrylate having structure IV

wherein R1 is hydrogen or methyl, and U is a bond, an oxygen atom, a sulfur atom, a
selenium atom, an SO2 group, an SO group, a CO group, a divalent C1-C20 aliphatic
radical, a divalent C3-C20 cycloaliphatic radical, or a divalent C3-C20 aromatic radical.
Brominated di(meth)acrylates falling within the genus represented by structure IV are
illustrated by Examples 1-1, 1-2, and 1-3 of Table 1.
As will be appreciated by those skilled in the art, multifunctional (meth)acrylates may
be prepared by nucleophilic ring opening of a polyglycidyl ether such as
tetrabromobisphenol A diglycidyl ether with acrylic acid or (meth)acrylic acid, and by
other methods known to those skilled in the art such as esterification of the hydroxyl
groups of a dihydroxy compound comprising the aromatic radical R2 with
(meth)acryloyl chloride. Suitable polyglycidyl ethers which can serve as precursors
to the corresponding multifunctional (meth)acrylate represented by the structure 1
include bisphenol A diglyeidyl ether, bisphenol-F diglycidyl ether, tetrabromo
bisphcnol-F diglycidyl ether, rcsorcinol diglycidyl ether, hydroquinone diglycidyl
ether, tetrabromocatechol diglycidyl ether; 3',3", 5',5"-tetrabromophenolphthalein
(CAS No. 1301-20-8) diglycidyl ether; 4,4'-biphenol diglycidyl ether; 1,3,5-
trihydroxybenzene triglycidyl ether; ],l,l-tris(4-hydroxyphenyl)ethane triglycidyl
ether, and the like.
20

RD 147821
Multifunctional (meth)acrylatcs represented by the structure 1 are also available
commercially. For example, a suitable multifunctional (meth)acrylate derived from
tetrabrominated bisphenol A diglycidyl ether is RDX 51027 available from Cytec
Surface Specialties. Other commercially available multifunctional acrylates include
EB600, EB3600, EB3605, EB3700, EB3701, EB3702, EB3703, and EB3720, all
available from Cytec Surface Specialties, and CN104 and CNI20 available from
SARTOMER.
The curable compositions of the present invention, and cured compositions prepared
from them, comprise at least one silicone-containing surfactant. Silicone-containing
surfactants are illustrated by polyalkyleneoxide modified polydimethyl siloxanes. In
certain instances, the curable compositions of the present invention exhibit
exceptional mold release properties upon curing. The preparation of
polyalkyleneoxide modified polydimethyl siloxanes is well known in the art.
Polyalkyleneoxide modified polydimethyl siloxanes of the present invention can be
prepared according to the procedure set forth in U.S. Pat. No. 3,299,112. Silicone-
containing surfactants are described in more detail in Kirk Othmer's Encyclopedia of
Chemical Technology, 4th Ed., Vol. 22, pp. 82-142, "Surfactants and Detersive
Systems." Further suitable nonionic detergent surfactants are generally disclosed in
U.S. Pat. No. 3,929,678, Laughlin et al., issued Dec. 30, 1975, at column 13, line 14
through column 16, line 6.
In one embodiment, the curable composition comprises a silicone-containing
surfactant, said surfactant comprising a polyalkyleneoxide modified
polydimethylsiloxane having structure V


RD 147821
wherein R6, R7, R8, and R arc independently at each occurrence a C1-C20 aliphatic
radical; A is a hydrogen or a C1-C20 monovalent aliphatic radical; "a" and "e" are
independently numbers ranging from 1 to 20; and "f" and "g" are independently
numbers ranging from 1 to 50.
Silicone-containing surfactants are widely available commercially and typically
comprise compositions comprising hydrophilic polyethcr substructures and
hydrophobic silicon-containing substructures. S1LWET 7602 and SILWET 720 are in
some embodiments preferred silicone-containing surfactants and are available from
OSi Specialty Chemicals, Ltd. Other suitable silicone-containing surfactants are
illustrated by, but are not limited to SILWET L-7608, SJLWET L-7607, SILWET L-
77, SILWET L-7605, SILWET L-7604, SILWET L-7600, SILWET L-7657 and
combinations thereof.
In one embodiment, the curable composition comprises a silicone-containing
. surfactant, wherein said surfactant comprises a polyalkyleneoxy group having a
molecular weight is less than or equal to about 10,000 grams per mole (g/mol). In an
alternate embodiment of the present invention, the molecular weight of the
polyalkyleneoxy group is less than or equal to about 8,000 g/mol. In yet another
embodiment the molecular weight of the polyalkyleneoxy group ranges from about
300 to about 5,000 g/mol.
Other silicone-containing surfactants are available from BYK-CHEM1E (for example,
BYK-300 and BYK-301), DOW CORNING (for example, ADDITIVE 11 AND
ADDITIVE 57), and EFKA (for example, EFKA 3236, EFKA 3239, EFKA 3299 and
EFKA 3232).
The silicone-containing surfactant is typically present in an amount corresponding to
from about 0.01 to about 5 weight percent based upon the total weight of the curable
composition. In one embodiment, the silicone-containing surfactant is present in an
amount corresponding to from about 0.1 to about 1 weight percent based upon the
total weight of the curable composition. In an alternate embodiment of the present
invention, the silicone-containing surfactant is present in an amount corresponding to
22

RD 147821
from about 0.1 to about 0.5 weight percent based upon the total weight of the curable
composition.
Typically, the multifunctional (meth)acrylate is present in the curable composition in
an amount corresponding to from about 30 to about 80 weight percent of the total
weight of the composition. In one embodiment, an amount of multifunctional
(meth)acrylate greater than or equal to about 35 weight percent may be present in the
curable composition. In yet another embodiment an amount of multifunctional
(meth)acrylate greater than or equal to about 45 weight percent may be present in the
curable composition. In still yet another embodiment, an amount of multifunctional
(meth)acrylate greater than or equal to about 50 weight percent may be present in the
curable composition. In one embodiment, an amount of multifunctional
(meth)aerylate corresponding to less than or equal to about 75 weight percent may be
may be present in the curable composition. In yet another embodiment, an amount of
multifunctional (meth)acrylate corresponding to less than or equal to about 70 weight
percent may be may be present in the curable composition. In still yet another
embodiment, an amount of multifunctional (meth)acrylate corresponding to less than
or equal to about 65 weight percent may be may be present in the curable
composition.
Typically, monofunctional (meth)acrylate is present in the curable composition in an
amount corresponding to from about 20 to about 50 weight percent of the total weight
of the composition. Within this range, it may be preferred to use an amount of greater
than or equal to about 20 weight percent, and in certain embodiments more preferably
greater than or equal to about 30 weight percent.
In one embodiment, the present invention provides a curable composition wherein
said multifunctional (meth)acrylate I is present in an amount corresponding to from
about 30 to about 80 weight percent of the total weight of the composition, and said
monofunctional (meth)acrylate is present in an amount corresponding to from about
20 to about 70 weight percent of the total weight of the composition.
23

RD 147821
As noted, in one embodiment, the present invention provides a curable composition
comprising (a) at least one silicone containing surfactant, wherein the surfactant is
present in a range corresponding to from about 0.01 to about 5 weight percent based
upon the total weight of the composition; (b) a multifunctional (meth)acrylate
represented by the structure I; (c) at least one monofunctional (meth)acrylate; and
optionally (d) one or more nanoparticulate fillers. In one embodiment, the
monofunctional (meth)acrylate is selected from the group consisting of methyl
acrylate, methyl (meth)acrylate, and arylether (meth)acrylate monomers having
structure VI

wherein R10 is hydrogen or methyl; X2 and X3 are independently in each instance O,
S, or Se; R11 is a divalent C1-C20 aliphatic radical, a divalent C3-C20 cycloaliphatic
radical, or a divalent C3-C20 aromatic radical; and Ar is monovalent C3-C20 aromatic
radical.
In an alternate embodiment, the present invention provides a curable composition
comprising (a) at least one silicone containing surfactant, wherein the surfactant is
present in a range corresponding to from about 0.01 to about 5 weight percent based
upon the total weight of the composition; (b) a multifunctional (meth)acrylatc
represented by the structure I; (c) at least one monofunctional (mcth)acrylate having
structure VI ; and optionally (d) one or more nanoparticulate fillers.
24

RD 147821
Suitable monofunctional (meth)acrylates having structure VI are illustrated by, but are
not limited to, the specific examples provided in Table 2 below.
25
TABLE 2 MONOFUNCTIONAL (METH)ACRYLATES HAVING STRUCTURE
VI


RD 147821
In one embodiment, the present invention provides a curable composition comprising
at least one monofunctional (meth)acrylate which is a phcnylthioethyl (meth)acrylate
having structure VII

wherein R10 is hydrogen or methyl.
In an alternate embodiment, the present invention provides a curable composition
comprising at least one monofunctional (meth)acrylate which is a naphthylthioethyl
(meth)acrylate VIII

wherein R10 is hydrogen or methyl.
In addition to providing curable compositions, the present invention also provides
cured compositions prepared from the curable compositions and articles comprising
the cured compositions. Any of the curable compositions disclosed herein may be
converted into the corresponding cured composition by polymerizing the
multifunctional (meth)acrylate and monofunctional (meth)acrylate components of the
curable composition. Those skilled in the art will appreciate that the multifunctional
(meth)acrylate and monofunctional (meth)acrylatc components of the curable
composition will be consumed as the curable composition is cured to give the cured
composition. Those skilled in the art will further appreciate that the multifunctional
26

RD 147821
(meth)acrylate and monofunctional (mcth)acrylate components of the curable
composition will be converted into structural units derived from the multifunctional
(meth)acrylate components and structural units derived from the monofunctional
(meth)acrylate components. For example, a curable composition comprising as the
monofunctional (meth)acrylate a phenylthioethyl (meth)acrylate having structure VII
will, upon curing, comprise structural units derived from the phenylthioethyl
(meth)acrylate VII, said structural units being represented by structure IX

wherein R10 is hydrogen or methyl, and further wherein the wavy lines
indicate the connections to adjacent structural units within the cured
composition. Those skilled in the art will appreciate that in most instances, the non-
polymerizable components of the curable composition will be present in the cured
composition as well.
Thus, in one embodiment, the present invention provides a cured composition
comprising:
(a) at least one silicone containing surfactant, wherein the
surfactant is present in a range corresponding to from about 0.01 to about 5 weight
percent based upon the total weight of the composition;
(b) structural units derived from at least one multifunctional
(meth)acrylatc represented by the structure 1
27

RD 147821

I
wherein R1 is hydrogen or methyl; X1 is O, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical;
(c) structural units derived from at least one monofunctional
(meth)acrylate; and optionally
(d) one or more nanoparticulatc fillers.
As noted, in certain embodiments, the curable compositions of the present invention
comprise at least one nanoparticulate filler. Nanoparticulate fillers, which are also
referred to as "nanoscale fillers" are particulate materials which are nanoscale in size
having a particle size no greater than about 250 nanometers (nm). In one
embodiment, the particle size is preferably between about 1 nanometers and about
100 nanometers, or any range there between. In yet another embodiment of the
present invention the particle size is between about 5 nanometers and about 50
nanometers. Measurements of nanoparticulate filler particle size may be made using
known techniques such as transmission electron microscopy (TEM).
Examples of materials suitable for use as nanoparticulate fillers include, but are not
limited to nanoparticulate silica, zirconia, titania, ceria, alumina, antimony oxide, and
mixtures thereof. Metal oxide nanoparticles are also referred to herein at times as
"nanoparticulate metal oxides". In one embodiment, the nanoparticulate filler
comprises a nanoparticulate mixed metal oxide. Nanoparticulate fillers comprising a
variety of metal oxides are commercially available. For example, nanoparticulate
silica is available in a variety of forms from DeGussa AG. Mixed metal oxide
nanoparticles are available from the Catalysts and Chemical Industries Corporation
(Japan).
28

RD 147821
In one embodiment of the present invention, the nanoparticulate filler additionally
comprises organic functional groups. Suitable organic functional groups include
(meth)acryloyloxy groups

wherein R1 is hydrogen or methyl. Other suitable organic functional groups include
aliphatic radicals such as decyl groups, cycloalipghhatic radicals such as
cyclohexylethyl groups, and cromatic radicals such as styryl groups. The structure of
the functional groups present in the functionalized nanoparticulate filler may be
adjusted depending upon the requirements of the application for which the
composition is intended. For example, the structure of the functional groups present
in the functionalized nanopaniculate filler may be tailored to provide a functionalized
nanoparticulate filler having u hydrophobic surface as in the case of an functionalized
nanoparticulate filler comprising surface decyl groups. Alternatively, the structure of
the functional groups present in the functionalized nanoparticulate filler may be
tailored to provide a nanopaiiculate filler having a hydrophilic surface. As in the
case of functionalized nanoparticulate fillers comprising (mefh)acryloyloxy groups,
the functional groups may be tailored to provide a functionalized nanoparticulate filler
which is reactive with (meth)acryloyloxy groups present in other components of a
curable composition. For example, in one embodiment, the present invention
provides a curable composition comprising (a) at least one silicone containing
surfactant, wherein the surfactant is present in a range corresponding to from about
0.01 to about 5 weight percent based upon the total weight of the composition; (b) at
least one multifunctional (meth)acrylate represented by the structure I; and (c) at least
one functionalized nanoparticulate filler, said functionalized nanoparticulate filler
comprising (meth)acryloyloxy groups. In an alternate embodiment, the present
invention provides a curable composition comprising (a) at least one silicone
containing surfactant, wherein the surfactant is present in a range corresponding to
from about 0.01 to about 5 weight percent based upon the total weight of the
composition; (b) at least one multifunctional (meth)acrylate represented by the
29

RD 147821
structure 1; (c) at least one monofunctional (meth)acrylate; and (d) at least one
functionalized nanoparticulate filler, said functionalized nanoparticulate filler
comprising (meth)acryloyloxy groups. In one embodiment, the functionalized
nanoparticulate filler comprises functional groups which are relatively inert (e.g.
ureido groups). In one embodiment, the present invention provides a curable
compositon comprising a nanoparticulate filler which is a nanoparticulate titania
coated with a urea formadehyde resin. Functionalized nanoparticulate fillers
comprising relatively inert functioanl groups are useful in applications requiring
greater stability of the nanoparticulate filler component of the composition.
In one embodiment, the nanoparticulate filler is an acrylate functionalized inorganic
nanoparticle, for example, an acrylate functionalized nanoparticulate silica, zirconia,
titania, ceria, alumina, antimony oxide, or mixture thereof. In a particular
embodiment, the nanoparticulate filler is an acrylate functionalized silica. In another
embodiment, the nanoparticulate filler is an acrylate functionalized mixed metal
oxide. The acrylate functionalized inorganic nanoparticulate filler can be produced by
adding an acrylate functionalized alkoxy silane such as acryloyloxypropyl
trimethoxysilane, methacryloyloxypropyl trimethoxysilane, acryloyloxypropyl
triethoxysilane, methacryloyloxypropyl triethoxysilane, mixtures of two or more of
the foregoing, and the like to an aqueous mixture of the inorganic nanoparticle, (for
example an aqueous mixture comprising a nanoscale silica colloid) and heating the
mixture to promote condensation of reactive groups on the surface of the inorganic
nanoparticle (for example hydroxyl groups) with the acrylate functionalized alkoxy
silane. Those skilled in the art will appreciate that a nanoparticle may be "completely
functionalized" or "partially functionalized" and the degree to which a nanoparticle is
functionalized may depend on the relative amounts of functionalizing agent and the
parent nanoparticle employed in the functionalization reaction. In one embodiment,
the degree to which a nanoparticle is functionalized may be predicted based upon a
proposition (See ILER in U.S. Patent No. 2786042) that each gram of nanoparticle
will require 19.7/d millimoles (19.7 divided by the diameter of the nanoparticle
expressed in nanometers) of functionalizing agent to achieve complete (100%)
functionalization. While not wishing to be bound by this relationship, it may
30

RD 147821
nonetheless serve as a guide to those wishing to effect complete or partial
functionalization of a nanoparticle. In one embodiment, the nanoparticle is folly
functionalized. In another embodiment, the nanoparticle is from about 1% to about
100% functionalized. In yet another embodiment another embodin.ent, the
nanoparticle is from about 3% to about 75% functionalized. In yet still another
embodiment, the nanoparticle is from about 5% to about 50% functionalized. In one
embodiment, the inorganic nanoparticle comprises nanoparticulate silica, the
nanoparticulate silica comprising silanol groups (SiOH) groups which are then
condensed with an acryloyloxy silane (for example methacryloyloxypropyl
trimethoxysilane). In one embodiment, water is removed from the mixture
comprising the product functionalized nanoparticulate filler, by the addition of an
organic solvent followed by vacuum stripping. Removal of water allows solution
blending of the functionalized nanoparticulate filler with the other components of the
curable composition. Suitable materials for the organic solvents include organic
solvents forming azeotropes with water (for example t-butanol) and solvents having a
boiling point higher than that of water. In one embodiment, the solvent is an acrylate,
for example ethyl mefhacrylate (boiling point = 118-119°C).
The amount and/or nature of the nanoparticulate filler in the curable composition may
be adjusted depending upon the requirements of the application for which the
composition is intended. The term "nature of nanoparticulate filler" is meant to
encompass the composition, chemical properties and physical properties of the
nanoparticulate filler. For example, the desired useable shelf life of a curable
composition may be adjusted by varying the amount and/or nature of the
nanoparticulate filler. Other properties of the curable composition and cured
compositions prepared from it may be adjusted by varying the amount and/or nature
of the nanoparticulate filler present in the curable composition. Properties which may
be tailored by varying the amount and/or nature of the nanoparticulate filler include
adhesion, abrasion resistance, weatherability, and thermal crack resistance to name a
few.
Typically, the amount of nanoparticulate filler present in the compositions of the
present invention is less than about 65 weight percent of the total weight of the
31

RD 147821
composition. In one embodiment, the nanoparticulate filler in the curable composition
is present in an amount corresponding to from about 1 weight percent to about 65
weight percent based upon the total weight of the curable composition. In another
embodiment, the nanoparticulate filler is present in an amount corresponding to from
about 1 to about 40 weight %. In yet another embodiment, the nanoparticulate filler is
present in an amount corresponding to from about 3 to about 35 weight %. In yet
another embodiment, the nanoparticulate filler is present in an amount corresponding
to from about 5 to about 30 weight %. In another embodiment, the nanoparticulate
filler is present in an amount corresponding to from about 1 to about 15 weight %.
The curable compositions of the present invention may, optionally, further comprise
an additive selected from flame retardants, antioxidants, thermal stabilizers,
ultraviolet stabilizers, dyes, colorants, anti-static agents, and the like, and a
combination comprising at least one of the foregoing additives, so long as the additive
does not deleteriously affect the polymerization of the composition.
The curable compositions of the present invention provide materials having excellent
refractive indices without the need for the addition of known high refractive index
additives. Such compositions, when cured into microstructured films, provide films
exhibiting excellent brightness.
The curable composition may be prepared by simply blending the components
thereof, with efficient mixing to produce a homogeneous mixture. When forming
articles from the curable composition, it is often preferred to remove air bubbles by
application of vacuum or the like, with gentle heating if the mixture is viscous. The
composition can then be charged to a mold that may bear a microstructure to be
replicated and polymerized by exposure to ultraviolet radiation or heal to produce an
article comprising the cured composition.
In one embodiment, the curable composition is applied as a liquid to a surface of a
base film substrate. The coated base film is then passed through a compression nip
defined by a nip roll and a casting drum, the casting drum having a negative pattern
master of the microstructures desired in the cured film. The compression nip applies
32

RD 147821
a sufficient pressure to the uncured composition and the base film substrate to control
the thickness of the coating of the curable composition and to press the composition
into full dual contact with both the base film substrate and the casting drum to exclude
any air between the composition and the drum. The base film substrate can be made
of any material that can provide a sufficient backing for the curable composition such
as, for example, polymethyl mcthacrylate (i.e., PLEXIGLASS ™), polyester (e.g.
MYLAR™), polycarbonate (such as LEXAN™), polyvinyl chloride (VELBEX ®), or
even paper. In a preferred embodiment, the base film substrate is a bisphenol A
polycarbonate film.
In one embodiment, the curable composition is cured by directing radiation energy
through the base film substrate from the surface opposite the surface coated with the
curable composition while the curable composition is in full contact with the casting
drum to cause the microstructured pattern of the casting drum to be replicated in the
cured composition layer. This process is particularly suited for continuous
preparation of a cured composition disposed upon transparent substrate.
In one embodiment, the curable compositions arc preferably cured by UV radiation.
The wavelength of the UV radiation may be from about 1800 angstroms to about
4000 angstroms. Suitable wavelengths of UV radiation include, for example, UVA,
UVB, UVC, UVV, and the like; the wavelengths of the foregoing are well known in
the art. The lamp systems used to generate such radiation include ultraviolet lamps
and discharge lamps, as for example, xenon, metallic halide, metallic arc, low or high
pressure mercury vapor discharge lamp, and the like. The term "curing" includes both
polymerization (chain growth steps) and, optionally, cross-linking steps to form a
non-tacky material.
When heat curing is used, the temperature selected is typically in a range from about
80° to about 130°C. Within this range, a temperature of greater than or equal to about
90°C may be preferred. Also within this range, a temperature of greater than or equal
to about 100°C may be preferred. The heating period is typically in a range of from
about 30 seconds to about 24 hours. In certain embodiments, it may be preferred to
use a heating time of greater than or equal to about 1 minute, more preferably greater
33

RD 147821
than or equal to about 2 minutes. Such curing may be staged to produce a partially
cured and often tack-free composition, which then is fully cured by heating for longer
periods. In one embodiment, the composition may be both heat cured and UV cured.
In one embodiment, the curable composition is may be used in a continuous process
to prepare a cured film material in combination with a substrate. To achieve the rapid
production of cured material using a continuous process, the composition preferably
cures in a short amount of time.
Current manufacturing processes for the low cost production of cured films,
particularly light management films, require rapid and efficient curing of materials
followed by easy release of the cured film from the mold. The curable compositions
of the present invention have been found to efficiently cure under typical conditions
employed for the rapid, continuous production of cured, coated films employing UV
irradiation. Such compositions exhibit excellent relative degree of cure under a
variety of processing conditions.
In one embodiment, the present invention provides a curable composition comprising
at least one silicone containing surfactant, wherein the surfactant is present in a range
corresponding to from about 0.01 to about 5 weight percent based upon the total
weight of the composition; about 80 to about 20 weight percent of a multifunctional
(meth)acrylate; about 20 to about 80 weight percent of a monofunctional
(meth)acrylate, 0.01 to about 1 weight percent of an aliphatic a C10-C40 aliphatic acid;
and about 0.1 to about 2 weight percent of a phosphine oxide photoinitiator.
Other embodiments of the present invention include articles made from any of the
curable compositions. Articles that may be fabricated from the compositions of the
present invention include, for example, optical articles, such as light management
films for use in back-light displays, projection displays, traffic signals, illuminated
signs, optical lenses; Fresnel lenses, optical disks, diffuser films, holographic-
substrates, and as substrates in combination with conventional lenses, prisms or
mirrors.
EXAMPLES
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The following examples are intended only to illustrate methods and embodiments in
accordance with the invention, and as such should not be construed as imposing
limitations upon the claims. Unless specified otherwise, all ingredients are
commercially available.
The compositions prepared in Examples 1-7 and Comparative Examples 2-10 did not
contain a nanoparticulate filler. Data for Examples 1-7 and Comparative Examples 2-
10 illustrate the surprising effect of silicone containing surfactants on the performance
of films prepared from the curable compositions of the invention. The formulations
for Examples 1-7 and Comparative Examples 2-10 were prepared from the
components listed in Table 3.
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Table 3

Component Trade Name Description Source
RDX51027("RDX") RDX51027 Diacrylate of tetrabromobisphenol-A diglycidy!ether Cytec SurfaceSpecialties
PTEA BX-PTEA Phenylthioethyl acrylate BimaxCompany
PEA SR339 2-Phenoxyethyl acrylate Sartomer
1RGACURE IRGACURE819 Bis(2,4,6-trimcthylbenzoyl)-phenylphosphine oxide Ciba-Geigy
Darocur Darocur4265 2-Hydroxy-2-methyl-l -phenyl-propan-1-one andBis(2,4,6-trimethylbenzoyl)-phenylphosphinc oxide Ciba SpecialtyChemicals
HDDA SR238 Hexanediol Diacrylate Sartomer
BDDA SR213 Butanediol Diacrylate Sartomer
Polyether modifieddimethylpolysiloxane-copolymer BYK301 Polyether modifieddimethylpolysiloxane-copolymer BYK-Chcmic
Polyether modifieddimethylpolysiloxane-copolymer SILWETL7602 Polyether modifieddimethylpolysiloxane-copolymer OSi SpecialtyChemicals, Ltd
Polyether modifieddimethylpolysiloxane-copolymer SILWETL720 Polyether modifieddimethylpolysiloxane-copolymer OSi SpecialtyChemicals, Ltd
Polycarbonate Lcxan Optical Quality Film GE AdvancedMaterials
36

RD 147821
A laminating process was used to coat polycarbonate film. The laminating unit
consisted of two rubber rolls: a bottom variable speed drive roll and a pneumatically
driven top nip roll. This system was used to press together laminate stacks that are
passed between the rolls. Coated films were prepared by placing approximately 5mL
of liquid coating at the front or leading edge of an 11" x 12" electro formed tool held
in place on a steel plate by adhesive tape. A piece of polycarbonate film was then
placed over the electroformed tool with the liquid coating and the resulting stack sent
through the laminating unit to press and distribute the photopolymerizable liquid
uniformly between the electroformed tool and polycarbonate substrate.
Photopolymerization of the coating within the stack was accomplished using a Fusion
EPIC 6000UV curing system by passing the stack under a 600-watt V-bulb.
After curing, the coated polycarbonate film was removed from the electroformed tool
by peeling away. This was accomplished by lifting the film away from the
electroformed tool at approximately a 45-90 degree angle. When no surfactant was
used, considerable force was required to peel the coated film from the electroformed
tool, i.e. molding tool, whereas less force was required when the proper release
additive was used. The effort or force required to remove the coated film from the
tool was assessed and used to develop a Mold Release Score as described in Table 4.
Typically, the problems with the nature of the release include buckling or curling of
the film after release, phase separation of components, delamination of the coated film
from the plastic backing, adhesion to the plastic backing. The coated cured ilat film
was then peeled from the flat tool and used for abrasion, % haze, % transmission,
color, yellowness index, and adhesion measurements.
Coated cured microstructured films for measuring luminance were made in the same
manner as coated cured flat films by substituting the highly polished flat steel plate
with an electroformed tool with a prismatic geometry. The geometry of the prisms
can be found in Figure 6 of the copending United States Application Serial No.
10/065,981 entitled "Brightness Enhancement Film With Improved View Angle" filed
December 6, 2002, which is incorporated by reference herein in its entirety.
Table 4
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ExampleNo. Formulation ToolTemp(°F) CureTemp(°F) StripTemp(°F) Tool Release Score * GLuminance
Example 1 59.5%RDX /39.5%PTEA7 1%SILWET L720 104 111 102 -++++
Example 2 59.75%RDX /39.75%PTEA / 0.5%SILWET L7602 103 104 104 +++ (-)1%
Example 3 59.9%RDX /39.9%PTEA / 0.2%SILWET L720 106 109 106 +++ (-)1%
ComparativeExample 2 60%RDX /35%PTEA /5%HDDA 106 109 102 (-)2%
ComparativeExample 3 60%RUX /35%PTEA/5%1,4-BDDA 106 109 104 ++ (-)2%
CompraliveExample 4 60%RDX /37.5%PTEA /2.5%HDDA 106 109 102 +
ComparativeExample 5 60%RDX /35%PTEA /2.5%1,4-BDDA 106 108 102 +
Example 4 59.95%RDX /39.95%PTEA/0.1%SILWET L7602 105 105 104 +
Example 5 59.9%RDX /39.9%PTEA / 0.2%SILWET 1.720 95 108 95 +
Example 6 59.95%RDX /39.95%PTEA/0.l%SILWET L720 105 104 104 +
Example 7 60%RDX /40%PTEA / 0.3%DYK301 104 105 102 -
Comparative 6()%RDX / 106 105 99 -
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Example 7 40%PTEA
ComparativeExample 8 60%RDX /30%PTEA /10%HDDA 95 95 93
ComparativeExample 9 60%RDX /40%PTEA 81 88 86
ComparativeExample 10 60%RDX /40%PTEA 73 82 80
* The tool release score is a measure of the release of the film from the tool and is a
combination of multiple characteristics such as release, buckling of the film, adhesion
to the substrate, and luminance.
"++++" represents excellent release and excellent film characteristics, "+++"
represents excellent release and good film characteristics, "++" represents good
release and good film characteristics, "+" represents average release and average film
characteristics, "-" represents a weakness in either the release or the film
characteristics, "- -" represents poor release and poor film characteristics,"—"
represents very poor release and very poor film characteristics
The data in Table 4 demonstrate that those compositions comprising the silicone-
containing surfactants, even in concentrations as low as 0.1 % by weight to 1% by
weight, possess better release characteristics as compared to the compositions that do
not contain the surfactants. There was reduced delamination between the coating and
polymer substrate, better adhesion between the two layers, and excellent release for
those compositions comprising the silicone-containing surfactant. These examples
show the surprising discovery of the effect of silicone-containing surfactants at low
concentrations on the coating compositions. While the data in Table 4 also show that
HDDA was effective for providing acceptable tool release characteristics, its use was
accompanied by an unacceptably high loss of luminance.
Curable Compositions Comprising Nanopartieulate Fillers: Examples 8-13
Preparation Of Curable Compositions Comprising Antimony Oxide Nanoparticles.
Examples 9-13 were prepared according to the following procedure using varying
amounts of the antimony oxide nanoparticle. Example 8 was prepared identically but
without the incorporation of the antimony oxide nanoparticle. Suncolloid AMT-33OS
antimony oxide (particle size less than 7 nm) as a mixture comprising 30% solids in
39

RD 147821
methanol, was obtained from Nissan Chemical Industries, Ltd. To 100 parts by
weight (pbw) of a curable composition comprising 60 pbw RDX51027 tertrabromo
BPA "epoxy" acrylate (Cytec Surface Specialties), 40 pbw phenylthioethyl acrylate,
0.50 pbw IRGACURE 819, 0.25 pbw acrylic acid, and 0.25 pbw S1LWET 7602 was
added an amount of the Suncolloid AMT-33OS corresponding to the amount set forth
in Table 5 below. Methanol was removed by distillation to afford the curable
composition containing various levels of dispersed antimony oxide.
Table 5 Curable Compositions Comprising Varying Levels of Unfunctionalized
Sb2O3 Nanoparticles

Example No. CurableComposition pbw SuncolloidAMT-330S, pbw Sb2O5 in UVResin, %
8 100 0 0
9 100 17.5 5
10 100 29 8
11 100 37 10
12 100 45.5 12
13 100 58.8 15
Preparation of Cured Films Comprising Surface Microstructures
The curable compositions of Examples 8-13 were used to prepare cured films
comprising surface microstructures. The cured film samples were prepared on a
continuous polycarbonate base film. Thus, about 5 grams of each of the curable
compositions of Examples 8-13 was applied as a bead across the web between a nip
roll and a cast roll held at 50° C. The cast roll had attached to its outer surface a metal
form with a microstructured surface. The coating formulation was cured while in
contact with the microstructured surface of the metal form by exposure to the output
of two high intensity UV lamps equipped with V-bulbs with the web running at 50
feet per minute. This technique was employed for each of the curable compositions
of Examples 8-13 to provide cured films comprising surface microstructures, said
films comprising structural units derived from RDX51027 diacrylate and
phenylthioethyl acrylate, as well as the silicone surfactant, presumably unchanged by
40

RD 147821
the irradiative curing step. The cured films prepared from the curable compositions of
Examples 9-13 also comprised the antimony oxide nanoparticles in the amounts
shown in Table 5. The cured films prepared from the curable composition of
Example 8 contained no antimony oxide nanoparticles. All of the cured films
exhibited excellent mold release.
Cured Film Abrasion Tests
The abrasion performance of the cured film samples was measured in an oscillating
bead abrasion test. Prior to being subjected to the oscillating bead abrasion test, the
percent transmission of each of the cured film prepared from the curable compositions
of Examples 8-13 was measured using a Gardner HAZE-GARD PLUS instrument by
shining the collimated light through the back side of the microstructured film. The
total internal reflection properties of such films results in very low transmission in this
configuration. Any increase in % transmission after abrasion is a direct measure of
damage to the prismatic structures. In the abrasion test the cured test film was
attached to the bottom of a fiat bin and 13.5 grams of 4 mm glass beads were placed
on top of the film. The bin was placed on an oscillator and oscillated at 180
oscillations per minute (opm) for 2 minutes. The test film was then removed and the
percent transmission of the film was measured. Four replicate cured films made from
each of the curable compositions of Examples 8-13 were subjected to this test. The
difference in percent transmission before and after glass bead abrasion was averaged.
A BEFI1 film (3M Corporation) was subjected to the abrasion resistance test.
Abrasion test results for the BEF11 are included here as a control. Results are set forth
in the Table 6 below.
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Table 6 Abrasion Performance Of Films Prepared From The Curable Compositions
Of Examples 8-13

Example No. Sb2O5 in CurableComposition % Change in Transmittance
8 0% 1.06
9 5% 1.2
10 8% 1.28
11 10% 1.15
12 12% 1.11
13 15% 1.13
BEFII Control 0% 0.73
The data in Table 6 show that the inclusion of unfunctionalized antimony oxide
nanoparticles in the eurable composition did not improve abrasion resistance (as
measured by the glass bead abrasion test) of cured films prepared from the curable
compositions of the present invention. A smaller change in % transmission was taken
to indicate better abrasion resistance.
Example 14 Preparation Of Chemically Modified Antimony Oxide Nanoparticles In
UV Resin
To 120.7 pbw of the Suncolloid AMT-330S antimony oxide nanoparticle dispersion
was added 12.93 pbw of 3-methacryloxypropyltrimethoxysilane, and 4.73-pbw water.
The mixture was then heated to reflux. After refluxing for 2 hours, the dispersion was
cooled and 25 pbw of t-butanol (solvent) was added. To this mixture was then added
112 grams of a curable composition comprising 60 pbw RDX51027 brominated
cpoxy acrylate (Cytec Surface Specialties), 40-pbw phenylthioethyl acrylate, 0.50
pbw IRGACURE 819, 0.25 pbw acrylic acid, and 0.25 pbw S1LWET 7602 silicone
polyether copolymer. Solvent was then removed under reduced pressure to afford
curable composition comprising chemically modified antimony oxide nanoparticles.
Preparation Of Cured Films Comprising Chemically modified Antimony Oxide
Nanoparticles
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Cured films incorporating surface microstructures were prepared as described for the
cured films prepared from the curable compositions of Examples 8-13. The curable
composition of Example 14 comprising the chemically modified antimony oxide
nanoparticlcs was used to prepare a representative number of cured films for abrasion
and luminance testing.
Oscillating Bead Abrasion Resistance Cured Films Comprising Chemically modified
Antimony Oxide Nanoparticles
The abrasion resistance of cured films prepared from the curable composition of
Example 14 was carried out as described for cured films prepared from the curable
compositions of Example 8-13. A BEF11 film was included as a control. Results are
gathered in Table 7.

Table 7
Example Sb 2O5 in Curable Comporion % Change in % Transmission
Example 14 25 0.43*
BEF II (control) 0 0.57
* Average value basec on four test films.
The data in Table 7 demonstrate that the cured films prepared from the curable
composition of Example 14 exhibits better abrasion resistance than a control film,
BEFI1. It is believed that the presence of reaction products in the cured film of the
chemically modified antimony oxide nanoparticles with other reactive components in
the curable composition (e.g. the multifunctional (mcth)acrylatc) provides a cured
film with a more robust microreplicated surface relative to the control film.
Luminance Of Cured Films Prepared from Curable Compositions Comprising
Chemically Modified Antimony Oxide Nanoparticles
Cured films supported on a polycarbonate substrate film were prepared using the
curable composition of Example 14 and the luminance of each film was measured and
compared to luminance of an otherwise identical cured film prepared using the
curable composition of Example 8 (no antimony oxide particles) and to a BEF11
43

RD 147821
control film. The data obtained ,arc presented in Table 8 and are "normalized" to the
BEFI1 control result.
Table 8

Example Luminance
Cured film prepared from the curable compositon ofExample 8 (no Sb2O5) 107.1
Cured film prepared from the curable compositon ofExample 14 (contains chemically modified Sb2O3) 107.8
DEF11 (control) 100
The data in Table 8 demonstrate that cured films prepared from curable compositions
comprising chemically modified antimony oxide nanoparticles exhibit greater
luminance than cured films prepared from curable compositions lacking chemically
modified nanoparticles.
The foregoing examples are merely illustrative, and represent specific embodiments
of the invention. The appended claims are intended to claim the invention as broadly
as it has been conceived and the examples herein presented are illustrative of selected
embodiments from a manifold of all possible embodiments. Accordingly, it is
Applicants' intention that the appended claims are not to be limited by the choice of
examples utilized to illustrate features of the present invention. As used in the claims,
the word "comprises" and its grammatical variants logically also subtend and include
phrases of varying and differing extent such as for example, but not limited thereto,
"consisting essentially of and "consisting of." Where necessary, ranges have been
supplied, those ranges are inclusive of all sub-ranges there between. It is to be
expected that variations in these ranges will suggest themselves to a practitioner
having ordinary skill in the art and where not already dedicated to the public, those
variations should where possible be construed to be covered by the appended claims.
It is also anticipated that advances in science and technology will make equivalents
and substitutions possible that are not now contemplated by reason of the imprecision
44

RD 147821
of language and these variations should also be construed where possible to be
covered by the appended claims.
45

RD 147821
WHAT IS CLAIMED IS:
1. A curable composition comprising:
(a) at least one silicone containing surfactant, wherein the surfactant
is present in a range corresponding to from about 0.01 to about 5 weight percent based
upon the total weight of the composition; and
(b) at least one multifunctional (meth)acrylate represented by the
structure 1

I
wherein R1 is hydrogen or methyl; X1 is O, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical.
2. The curable composition according to claim 1, further comprising at least
one nanoparticulate filler.
3. A curable composition comprising:

(a) at least one silicone containing surfactant, wherein the surfactant
is present in a range corresponding to from about 0.01 to about 5 weight percent based
upon the total weight of the composition;
(b) a multifunctional (meth)acrylate represented by the .structure 1


RD 147821
wherein R1 is hydrogen or methyl; X1 is 0, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical; and
(c) at least one monofunctional (meth)acrylate.
4. The curable composition according to claim 3, further comprising at least
one nanoparticulate filler.
5. The curable composition according to claim 4, wherein said nanoparticulate
filler comprises at least one organic functional group.
6. The curable composition according to claims 3 or 4, wherein R2 is a divalent
aromatic radical having structure III

wherein and U is a bond, an oxygen atom, a sulfur atom, a selenium atom, an SO2
group, an SO group, a CO group, a C1-C20 aliphatic radical, C3-C20 cycloaliphatic
radical, or a C3-C20 aromatic radical; R4 is independently at each occurrence a halogen
atom, a nitro group, a cyano group, an amino group, a hydroxy group, a C1-C20
aliphatic radical, a C3-C20 cycloaliphatic radical, or a C3-C20 aromatic radical; R5 is
independently at each occurrence a hydrogen atom, a hydroxy group, a thiol group, or
an amino group; W is a bond, a divalent C1-C20 aliphatic radical, a divalent C3-C20
cycloaliphatic radical, a divalent C3-C20 aromatic radical; and "m" and "p" are
independently integers ranging from 0 to 4.
47

RD 147821
7. The curable composition according to claims 3 or 4, wherein said silicone-
containing surfactant comprises a polyalkyleneoxidc modified polydimethylsiloxane
having structure V

wherein R6, R7, R8 and R9 are independently at each occurrence a C1-C20 aliphatic
radical; A is a hydrogen or a C1-C20 monovalent aliphatic radical; "a" and "e" are
independently numbers ranging from 1 to 20; and "f" and "g" are independently
numbers ranging from 1 to 50.
8. The curable composition according to claim 3 or 4, wherein said at least one
monofunctional (meth)acrylate is selected from the group consisting of methyl
acrylate, methyl (mefh)acrylate, and arylether (meth)acrylate monomers having
structure VI

wherein R10 is hydrogen or methyl; X2 and X3 are independently in each instance O,
S, or Se; R1' is a divalent C1-C20 aliphatic radical, a divalent C3-C20 cycloaliphatic
radical, or a divalent C3-C20 aromatic radical; and Ar is monovalent C3-C20 aromatic
radical.
48

RD 147821
9. The curable composition according to claim 3 or 4, further comprising an
aliphatic acid having structure II

wherein wherein R3 is a C9-C39 aliphatic radical, said aliphatic acid being present in
an amount corresponding to from about 0.01 to about 1 weight percent based upon a
total weight of the composition.
10. A cured composition comprising:
(a) at least one silicone-containing surfactant, said at least one
silicone-containing surfactant being present in an amount corresponding to from about
0.1 to about 5 weight percent based upon the total weight of the composition;
(b) structural units derived from at least one multifunctional
(meth)acrylate represented by the structure I

1
wherein R1 is hydrogen or methyl; X1 is O, S, or Se; n is at least 2; and R2 is a
polyvalent aromatic radical; and
(c) structural units derived from at least one monofunctional
(meth)acrylate.
11. The cured composition according to claim 10, further comprising at least one
nanoparticulate filler.

The present invention provides novel curable compositions useful in the preparation of light management films and other optical articles. The curable compositions comprise (a) at least one silicone-containing surfactant, (b) at least one a multifunctional (meth)acrylate having structure I; in certain embodiments (c) at least one nanoparticulate filler; and in certain embodiments, (d) at least one monofunctional (meth)acrylate. The curable compositions may be cured to provide the corresponding cured compositions and articles made therefrom.