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Composition Based On Allyl Monomers And Peroxide(s) For The Manufacture Of Organic Glasses

Abstract: The present invention relates to the use of one or more particular organic peroxides for the polymerisation of an allyl monomer and/or of at least one allyl copolymer. The invention also relates to a composition comprising at least one allyl monomer and/or at least one allyl copolymer and at least one particular organic peroxide. The invention also relates to the use of the composition as defined above for the manufacture of an organic glass, preferably an ophthalmic lens which can be tinted with pigments and/or organic or inorganic dyes.

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Patent Information

Application #
Filing Date
08 March 2019
Publication Number
22/2019
Publication Type
INA
Invention Field
POLYMER TECHNOLOGY
Status
Email
mail@rahulchaudhry.com
Parent Application
Patent Number
Legal Status
Grant Date
2022-02-03
Renewal Date

Applicants

ARKEMA FRANCE
420 rue d'Estienne d'Orves 92700 Colombes

Inventors

1. LAFARGE, Mélanie
39, Route des Fusillés SURESNES, 92150
2. VAN HEMELRYCK, Bruno
9, rue des Cerisiers 69630 Chaponost
3. DISSON, Jean-Pierre
364 Route des Condamines 69390 Vernaison

Specification

The present invention relates to the use of one or more particular organic peroxides for the polymerization of at least one allyl monomer and / or at least one allyl copolymer.
The invention also relates to a polymerizable composition comprising at least one allyl monomer and / or at least one allyl copolymer and at least one organic peroxide having the structure as defined below.
The invention also relates to the use of the composition as defined above for the manufacture of an organic glass, preferably an ophthalmic lens may be tinted using pigments and / or organic dyes, c that is to say with the aid of at least one coloring agent.

The present invention also relates to a method for preparing a plastic lens from the polymerization of the composition as defined above and that the organic glass itself.

The organic glasses, such as windows for optical instruments or detectors or alternatively the ophthalmic lenses may be prepared from the free radical polymerization of one or more allyl and / or copolymers of allyl monomers in the presence of one or more polymerization initiators, particularly organic peroxides.

By way of example, this polymerization can be implemented at a imp method liquant a molding step. In this case, the composition containing the mixture of allyl monomers and / or allyl copolymers in the presence of initiators inch lymérisation can be poured into a mold, may have a substantially concave or convex shape and po lymérisée and cured during an increase more or less gradual temperature. Once the polymerization is complete, we obtain an organic glass which can then undergo various types of treatment depending on the applications

desired. Alternatively, the composition may equally well be poured between two molds so as to recover, after polymerization, the corresponding organic glass.

However, organic peroxides, regularly used as polymerization initiators, are species usually very unstable when they are heated. Indeed, in case of an uncontrolled rise in temperature, some organic peroxides may undergo exothermic self-accelerating decomposition and s may ignite and / or explode so vio slow. Such behavior s' is therefore hardly compatible with the particular rules for the transport and storage of hazardous materials in areas intended for the production of plastic lenses.

Thus it s' is especially advantageous to formulate as liquid organic peroxides in so lvants (also called desensitation), that is to say in the dilute state, in order to reduce their thermal instability so as to then be able to store and transport safe.

For this purpose, organic peroxides belonging to the family of the dialkyl peroxydicarbonates can be solubilized in an allyl monomer such as diethylene glyco the bis (allyl carbonate) (ADC), marketed by the exemp under the name of CR-39® by PPG or as the RAV 7 by Acomon company Mitsui group. In this case, the allylic monomer acts as a reactive phlegmatisant which means it has the function on one hand, to solubilize the organic peroxide and, on the other hand, to intervene in the po radical lymérisation allyl monomers and / or allyl copolymers leading to the formation of organic glasses.

In particular, the use of diisopropyl peroxydicarbonate (often referred to as IPP), so lubilisé in diethylene glyco the bis (allyl carbonate) in an amount of 27% by weight relative to the total weight of the composition, during the radical polymerisation monomer (s) allyl (s) and / or allyl copolymers allows to lead to organic glasses having good optical properties, particularly in terms of transparency and low cost loration, as well as to good mechanical properties. In other words, the organic glasses obtained with such a composition of organic peroxide are transparent, inco lores and have good mechanical properties in terms of wear. Such an organic peroxide-based composition is by the exemp sold under the name Luperox ® IPP27 or by Arkema under the tradename Perkadox ® IPP-NS27 by Akzo.

However, the composition based on diisopropyl peroxydicarbonate still contains too much risk uncontrolled decomposition storage and transportation in case of an uncontrolled rise in temperature.

Indeed, diisopropyl peroxydicarbonate is a peroxide-called cold that is to say that it has alone or in mixture with other peroxides and / or desensitation reactive or not, a maximum transport temperature, also called temperature control set at 20 ° C in accordance with the recommendations on the Transport of dangerous materials a, 19 th edition 2015, in the section 2.5.3.2.4 on organic peroxides.

More generally, within the meaning of the present invention, by cold peroxide is any peroxide-based composition having a maximum transport temperature as defined above.

Thus, in spite of the dilution of the peroxydicarbonate diisopropyl in the allylic monomer, it s becomes necessary to place constantly at a temperature less than or equal to 20 ° C for the movement of products such as Luperox ® IPP27 or Perkadox ® IPP-NS27 particular to minimize the risk of uncontrolled decomposition, complicating significantly the conditions of transport and storage.

In addition, it is necessary to control the temperature during the transport and storage of these products so as to reduce the risk of early polymerization of the allyl monomer having a function of phlegmatiser the organic peroxide.

Furthermore, diisopropyl peroxydicarbonate has the drawback of being too reactive to be stored and transported at higher concentrations than 30% by weight in the allylic monomer.

In the state of the art, he already has been considered replacing peroxydicarbonate diisopropyl as initiator in radical polymerization based allyl monomers for the production of plastic lenses in order to overcome the disadvantages associated with safety problems previously exposed.

As examples, aromatic diacyl peroxides or peresters kind have already been used to.

Nevertheless, this type of organic peroxides, particularly benzoyl peroxide, d induces a strong yellowing of the organic glasses. Furthermore, peresters also have the disadvantage of being so low in lubles allyl monomers and to induce organic glasses are determined to be too weak mechanical properties. This is particularly the case peresters sold under the Luperox ® tradename 575 (tert-amyl peroxy-2-ethylhexanoate), Luperox ® 256 (2,5 -dimethyl-2,5 -di (2-ethylhexanoyl) peroxy) - hexane).

Similarly, the hydroperoxides alkyl such as tert-butyl hydroperoxide were also considered.

However, such peroxides have the disadvantage of generating free radicals at high temperatures compared with those of the dialkyl peroxydicarbonates in order to effectively carry out the radical polymerization of allyl monomers. Indeed, the hour half-life (Half Life Temperature in English or HLT) of hydroperoxides alkyl, ie the temperature at which half of the amount of peroxide is decomposed in a given time for a decomposition time of the same order of magnitude as the duration of polymerization of allyl monomers, s' is too high in the order of several tens of degrees. To generate free radicals at lower temperatures, of systems of chemical activation, such as ferrous ions, were added but these have proven inadequate due to the induced coloration in the resulting polymer which negatively impact on optical quality plastic lenses. Moreover, these activated hydroperoxides systems are sparingly soluble in the allylic monomers.

Among the organic peroxides families considered having a temperature of half life of less than 130 degrees for a period of 1 0:00, cyclic perkétals, such as those sold under the Luperox ® trade name 33 1 or Trigonox ® 22 (l, l - di (t-butylperoxy) -cyclohexane) or the Luperox ® tradename Trigonox ® 53 1 or 122 (l, l-di (t-amyl peroxy) cyclohexane), were tested. Such organic peroxides have the advantage to be able to be stored and transported at room temperature and are not subjected to a maximum temperature of transportation according to the recommendations for the transport of hazardous materials A as mentioned above.

However, the organic peroxides used in these commercial products are diluted in a so lvant such as a hydrocarbon, a mineral oil or a phthalate, which has the consequence of degrading the optical and mechanical properties of organic glasses recovered after polymerization. Indeed, these products have the disadvantage of introducing, for safety reasons, a third non-polymerizable material in the radical polymerization of allyl monomers thereby increasing the risk of heterogeneity in the finally obtained polymer.

Alternatively, the use of other percarbonates, such as those sold under the trade name Luperox ® 221 or 225 (respectively percarbonate, di-n-propyl percarbonate and di-sec-butyl), has also been considered as these lead to organic glasses with good optical and mechanical properties. For against these percarbonates still correspond to cold peroxides and pose the same safety problems in terms of transport and storage than compositions of diisopropyl peroxydicarbonate.

As a result, conventional peroxides often lead to organic lenses with lower mechanical and optical properties than plastic lenses obtained with cold peroxides.

Thus one of ective obj of the present invention is to overcome the aforementioned drawbacks, that is to say, to substitute the organic peroxides commonly used in the radical polymerization of allyl monomers and / or allyl copolymers, other polymerization initiators that may be stored and transported alone or mixed safely without degrading the optical and mechanical properties of organic glasses obtained.

In other words, there is a real need to offer other polymerization initiators that are likely to be stored and transported, alone or mixed, under strictly higher temperature conditions at 20 ° C while allowing manufacturing of organic glasses having good optical and mechanical properties, particularly in terms of transparency, low staining and wear.

The present invention thus has particular obj and the use of at least one peroxide of the formula (I):

1 -alcoxy- 1 -t-alkylperoxycyclohexane

(I)

Formula (I) wherein the alkoxy group comprises 1 to 4 carbon atoms, the group t-alkyl contains from 4 to 12 carbon atoms, and the cyclohexane ring is optionally substituted with 1 to 3 alkyl groups each having from 1 to 3 carbon atoms;

for polymerizing one or more allyl and / or copolymers of allylic monomers.

Peroxides of formula (I) have the advantage of having, alone or in mixture with other peroxides and / or desensitation reactive or not, a maximum transport temperature, also called temperature control, strictly greater than 20 ° C according to the recommendations for the transport of hazardous materials a, 19 th edition 20 15, in the section 2.5.3.2.4 on organic peroxides.

Thus the use of peroxides of formula (I), alone or in admixture, can improve safety conditions for transport and storage compared to cold peroxides, as defined above, in particular vis-à organic peroxides screw belonging to the family of the dialkyl peroxydicarbonates, especially in diisopropyl peroxydicarbonate so lubilisé in diethylene glyco the bis (allyl carbonate), and marketed under the trademark Luperox ® IPP27 or name Perkadox ® IPP-NS27.

In this way, the peroxides according to the invention are more easily manipulated and this safely thereby significantly reducing the costs of transport and storage.

Peroxides of formula (I) also have the advantage of being used alone, that is to say in the undiluted state thereby release itself on the one hand, the use of a not so lvant curable, such as oils, imposed for security reasons and likely to negatively impact on the optical and mechanical properties of organic glasses obtained and, on the other hand, the use of a so lvant polymerizable, such as an allyl monomer, likely to increase the risks for the transportation or storage of a start of polymerization not temperature regulated.

More generally, the peroxides of formula (I) make it possible to release itself from the installation of any type of storage dedicated to N polymerizable lvant or not the peroxide production sites (or device for storing a so lvant) which leads to significant space savings and reduced maintenance costs.

In other words, the peroxides according to the invention allow to release itself from any kind of problems related to the use of so lvants curable or not.

More particularly, the peroxides according to the invention make it possible to release itself phlegmatisant usual peroxides such as hydrocarbons, such as isododecane, mineral oils, esters such as liquid phthalates, ethylbenzene, allylic monomers.

And peroxides of formula (I) may be packaged in a variety of containers or devices that unstable thermally and conventional peroxides may decompose at an uncontrolled increase in temperature.

The peroxides according to the invention have a half life temperature at 10 hours (HLT l Oh) may allow efficient radical polymerization of allyl monomers and / or allyl copolymer.

Preferably, the peroxides according to the invention have a half life temperature at 1 hour (HLT lh) near the polymerization temperature.

Preferably, the composition polymerization temperature according to the invention is of more or less 20 ° C relative to the temperature half life of 1 hour of the peroxide used, preferably roughly 10 ° C relative to the half-life temperature at 1 hour of the peroxide.

In the case of a mixture of peroxides, the polymerization temperature is roughly 20 ° C relative to the temperature half life of 1 hour peroxide having the HLT higher, preferably roughly 10 ° C compared to the temperature half life of 1 hour peroxide having the highest HLT,

The term "polymerization temperature" is meant the maximum temperature reached during the heat cycle of crosslinking.

Thus the proposed peroxides may initiate polymerization of allyl monomers and / or allyl copolymers without necessarily resorting to systems for activating chemically, such as ferrous ions, which avoids the risks of coloring of plastic lenses.

Furthermore, the organic glasses obtained, following the polymerization of one or more allyl monomers and / or allyl copolymers in the presence of one or more peroxides of formula (I) have good optical and mechanical properties.

In particular, the organic glasses obtained are transparent, colorless or weakly colored and are resistant to wear.

Thus the or peroxides of formula (I) used in the polymerization of one or more allyl monomers and / or copolymers allyl, possible to manufacture organic glasses.

The invention also relates to a composition comprising at least one peroxide of the formula (I) as described above, and at least one allyl monomer and / or at least one allyl copolymer.

The composition according to the invention makes it possible to drive after polymerization to organic glasses having good optical and mechanical properties.

The composition according to the invention is polymerizable or capable of being polymerized.

Another object of the present invention relates to an organic glass obtained by po lymérisation of the composition as defined above.

Similarly, the invention relates to a preparation of an organic glass process comprising at least a step of polymerizing a composition as defined above in an apparatus comprising a mold.

Other features and advantages of the invention will become apparent from reading the description and examples that follow.

In what follows, and unless otherwise indicated, the limits of a range of values ​​are included in this document.

The term "at least one" is equivalent to the term "one or more".

use

As indicated above, the invention relates to the use of one or more peroxides of formula (I) as an initiator for polymerizing one or more allyl monomers and / or one or more copolymers allyl.

Thus the invention relates particularly to the use of one or more peroxides of formula (I) for the radical polymerization of one or more allyl monomers and / or one or more copolymers allyl.

In other words, the one or more peroxides of formula (I) is or are used in particular as an radical polymerization initiator.

Or the peroxides of formula (I) may be used alone or in admixture, in particular with other polymerization initiators in the po lymérisation of one or more allyl monomers and / or one or more copolymers allyl.

Preferably, the or peroxides of formula (I) are used alone.

Alternatively, the or peroxides of formula (I) may be used in admixture with one or more peroxides of formula (III):

bis-t-alkylperoxycyclohexane (III)

Formula (III) wherein each group includes t-alkyl of 4 to 12 carbon atoms and the cyclohexane ring is optionally substituted with 1 to 3 alkyl groups each having 1 to 3 carbon atoms.

Preferably, the compound of formula (III) is selected from the group consisting of 1, 1 -di (tert-butylperoxy) -3, 3, 5 -trimethylcyclohexane, 1, 1 -di (tert-amyl peroxy) - cyclohexane, 1, 1 -di (t-butylperoxy) -cyclohexane and mixtures thereof.

A particularly preferred mixture comprises 1-methoxy-l-tert-amylperoxycyclohexane as compound of formula (I) and at least one compound of formula (III), preferably selected from the

consisting of l, l-di (tert-butylperoxy) -3, 3, 5 -trimethylcyclohexane, the l, l-di (tert-amyl peroxy) cyclohexane, 1, 1 -di (t-butylperoxy) -cyclohexane and mixtures thereof.

Preferably, when the or peroxides of formula (I) are used in admixture with one or more other polymerization initiators, preferably with one or more peroxides of formula (III), the ratio between the compound of formula (I ) and the one or more other polymerization initiators, preferably one or more peroxides of formula (III) is between 99: 1 and 30: 70, preferably between 50: 50 and 99: 1, more preferably between 60: 40 and 80: 20.

Peroxide of formula (I)

The one or more peroxides according to the invention have a structure of formula (I):

1 -alcoxy- 1 -t-alkylperoxycyclohexane

(I)

Formula (I) wherein the alkoxy group comprises 1 to 4 carbon atoms, the group t-alkyl contains from 4 to 12 carbon atoms, and the cyclohexane ring is optionally substituted with 1 to 3 alkyl groups each having from 1 to 3 carbon atoms.

Preferably, in formula (I), the alco xy group corresponds to a methoxy or ethoxy group, preferably a methoxy group.

Preferably, in formula (I), the group t-alkyl contains from 4 to 8 carbon atoms, preferably four or five carbon atoms, more preferably five carbon atoms.

According to one embodiment, the cyclohexane ring is substituted by 1 to 3 alkyl groups each having 1 to 3 carbon

atoms, preferably substituted by three alkyl groups each having one carbon atom.

Preferably, the or peroxides of formula (I) is or are selected from 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC), 1-methoxy-1-t-butylperoxycyclohexane (TBPMC), 1 -methoxy- 1-t-amylperoxy-3, 3, 5 -triméthylcyclohexane, 1-methoxy-1-t-butylperoxy-3, 3, 5 -triméthylcyclohexane, 1 -ethoxy-1-t-amylperoxycyclohexane (Tāpēc), 1 - ethoxy-1-t-butylperoxycyclohexane (TBPEC), 1 -ethoxy-l -t-amy the peroxy-3, 3, 5 -trimethylcyclohexane and / or 1-ethoxy-1-t-butyl peroxy the 3, 3 5 -trimethylcyclo hexane.

More preferably, the peroxide of formula (I) is 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC) as sold under the trade name Luperox ®V 10 by Arkema.

Advantageously, the peroxides of formula (I) present (ent) a half-life temperature at 10 hours, denoted the HLT Oh, greater than or equal to 60 ° C and less than or equal to 130 ° C.

mixtures

Or the peroxides of formula (I) may be used in mixture, especially with other polymerization initiators.

Preferably, the or peroxides of formula (I) may be used in admixture with one or more peroxides of formula (III):

bis-t-alkylperoxycyclohexane (III)

Formula (III) wherein each group includes t-alkyl of 4 to 12 carbon atoms and the cyclohexane ring is optionally substituted with 1 to 3 alkyl groups each having 1 to 3 carbon atoms.

Preferably, the compound of formula (III) is selected from the group consisting of 1, 1 -di (tert-butylperoxy) -3, 3, 5 -trimethylcyclohexane, 1, 1 -di (tert-amyl peroxy) - cyclohexane, 1, 1 -di (t-butylperoxy) -cyclohexane and mixtures thereof.

A particularly preferred mixture comprises 1-methoxy-l-tert-amylperoxycyclohexane as compound of formula (I) and at least one compound of formula (III), preferably selected from the consisting of l, l-di (tert butylperoxy) -3, 3, 5 -trimethylcyclohexane, the l, l-di (tert-amyl peroxy) cyclohexane, 1, 1 -di (t-butylperoxy) -cyclohexane and mixtures thereof.

Preferably, when the or peroxides of formula (I) are used in admixture with one or more other polymerization initiators, preferably with one or more peroxides of formula (III), the ratio between the compound of formula (I ) and the one or more other polymerization initiators, preferably one or more peroxides of formula (III) is between 99: 1 and 30: 70, preferably between 50: 50 and 99: 1, more preferably between 60: 40 and 80: 20.

Monomer (s) allyl (s) and / or copolymer (s) allyl (s)

The or allyl monomers may be selected from monomers bis (allyl carbonate).

Advantageously, the allylic monomer is or monomers are chosen from bis (allyl carbonate) of the dio of formula (II):

OO

R a - O-C-O-R- O-C-O-R c

Formula (II) wherein:

• R a and R c , identical or different, represent an allyl group of the following formula:

Formula wherein Rd is selected from:

- a hydrogen atom,

- a halogen atom, preferably a fluorine or chlorine atom,

- an alkyl group, linear or branched C 1 - C 4,

• Rb is selected from alkylene groups, ether groups alkylene, ether groups of aromatic alkylene polyether groups alkylene, carbonate groups alkylene and mixtures thereof.

Preferably, in formula (II), R a and R c are identical.

Preferably, R a and R c are identical and represent an allyl group wherein Rd represents a hydrogen atom, a chlorine atom, a bromine atom, methyl or ethyl.

More preferably, R a and R c are identical and represent an allyl group wherein Rd represents a hydrogen atom.

Preferably, Rb represents an alkylene group, an ether group or an alkylene ether group of aromatic alkylene.

More preferably, Rb represents an alkylene group or an ether group of alkylene.

Even more preferably, Rb is an ether group of alkylene, especially the group of the following formula:

In formula (II), Rb is preferably aliphatic, that is to say that it is not an ether of aromatic alkylene. In other words, the one or more allyl monomers is or are preferably selected from monomers bis (allyl carbonate) of the aliphatic dio of formula (II).

The one or more allyl monomers is or are preferably selected (s) among the éthylèneglyco the bis allyl carbonate, diethylene glyco the bis 2-methyl carbonate, diethylene glycol bis (allyl carbonate) or ADC, the éthylèneglyco the bis (2 chloro allyl carbonate), triéthylèneglyco the bis (allyl carbonate), 1, 3 -propanedio the bis (allyl carbonate), propylene glyco the bis (2-ethyl allyl carbonate), 1, 3 -butènedio la ( allyl carbonate), 1, 4-butènedio the bis (2-bromo allyl carbonate), dipropylèneglyco the bis (allyl carbonate), triméthylèneglyco the bis (2-ethyl allyl carbonate), pentaméthylèneglyco the bis (allyl carbonate), isopropylene bis pheno bis (allyl carbonate) and mixtures thereof.

Preferably, the allylic monomer is diéthylèneglyco the bis

(Allyl carbonate), also called ADC, such as that sold under the trade name CR-39 by PPG or RAV 7 by Acomon company Mitsui group.

Other allyl monomers may be used alone or in combination with the monomers bis (allyl carbonate) of the aforementioned dio such as for example monomers bis (allyl carbonate) having no dio l in their structure.

The allyl or copolymers can be obtained from the polymerization of monomers bis (allyl carbonate) of the dio mentioned above.

The allyl or copolymers is or are preferably selected from poly (allyl carbonates) of polyo l.

The or po ly (allyl carbonates) of po lyols is or are obtained (s) from the polymerization of a polyo l and a monomer bis (allyl) carbonate.

Among the polyo ls used in the preparation of poly (allyl carbonates) of polyo bs, we may notably mention the polyols selected from 1, 6-hexanediol l, 1, 4-dimethano the cyclohexane, the dio ls polylactone, the dio ls polyethoxylated glycerol, alpha, alpha-xylènedio l, 1, 4-bis (hydroxyethyl) toluene, 2,2- (bis (4-hydroxyethyl) phenyl) propane, pentaérythrito l, l triméthylo propane the dipentaérythrito l, l ditriméthylo propane, tris (hydroxyethyl) isocyanurate.

The allyl or copolymers chosen from poly (allyl carbonates) of polyo l may be used in combination with allyl monomers mentioned above, including monomers bis (allyl carbonate) of the dio of formula (II).

The allyl or copolymers may also be obtained (s) from the polymerization of a monomer bis (allyl) carbonate and a polyether diol.

Polyether dio l is preferably selected from homopolymers, copolymers or block polymers dio ls polyethers such as those described in patent application US 6,506,864.

Preferably, the invention relates to the use of at least one peroxide of the formula (I) for the radical polymerization of one or more allyl monomers, preferably those chosen from the monomers bis (allyl carbonate) of the dio of formula (II).

More preferably, the invention relates to the use of 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC) for the radical polymerization of diéthylèneglyco the bis (allyl carbonate) (ADC).

Composition

As indicated previously, the composition according to the invention comprises at least an allyl monomer and / or at least one allyl copolymer and at least one polymerization initiator selected from peroxides of formula (I) as described above.

Preferably, the composition comprises at least one allylic monomer.

Preferably, the composition comprises at least one allylic monomer selected from monomers bis (allyl carbonate).

Preferably, the composition comprises at least one allylic monomer selected from monomers bis (allyl carbonate) dio l of formula (II), as described above, especially the monomers bis (allyl carbonate) dio the aliphatic of formula (II ).

According to one embodiment, the composition comprises at least one peroxide of the formula (I), wherein the alkoxy group represents a methoxy or ethoxy group, and at least one allyl monomer selected from monomers bis (allyl carbonate) diol formula (II), wherein R a and R c are identical and represent an allyl group wherein Rd represents a hydrogen atom and Rb represents an alkylene group or an alkylene ether group.

Preferably, the composition comprises 1-methoxy-1-tert-amylperoxycyclohexane and at least one allyl monomer selected from monomers bis (allyl carbonate) diol of formula (II) as described above.

More preferably, the composition comprises diethylene glycol bis (allyl carbonate) and 1-methoxy-1-tert-amylperoxycyclohexane.

The one or more peroxides may be present in the composition according to the invention in a content ranging from 0.01 to 10%, preferably from 0.01 to 5% by weight relative to the total weight of the allyl monomers and / allyl or copolymers present in the composition.

Preferably, the one or more peroxides may be present in the composition according to the invention in a content ranging from 0.01 to 10%, preferably from 0.01 to 5% by weight relative to the total weight of the monomer allyl present in the composition.

The composition according to the invention may also comprise at least one different polymerization initiator, organic peroxides of formula (I).

In this case, the polymerization initiator may be a different additional organic peroxide and organic peroxides of formula (I) or a non-peroxide compound.

In particular, the composition according to the invention may also comprise at least one additional organic peroxide different organic peroxides of formula (I).

Preferably, the one or more peroxide (s) organic (s) Additional (s) is or are selected from the peroxides of formula (III):

bis-t-alkylperoxycyclohexane (III)

Formula (III) wherein each group includes t-alkyl of 4 to 12 carbon atoms and the cyclohexane ring is optionally substituted with 1 to 3 alkyl groups each having 1 to 3 carbon atoms.

Preferably, the compound of formula (III) is selected from the group consisting of 1, 1 -di (tert-butylperoxy) -3, 3, 5 -trimethylcyclohexane, 1, 1 -di (tert-amyl peroxy) - cyclohexane, 1, 1 -di (t-butylperoxy) -cyclohexane and mixtures thereof.

A particularly preferred mixture comprises 1-methoxy-l-tert-amylperoxycyclohexane as compound of formula (I) and at least one compound of formula (III), preferably selected from the group consisting of l, l -di ( tert-butylperoxy) -3, 3, 5 -trimethylcyclohexane, the l, l-di (tert-amylperoxy) -cyclohexane, 1, 1 -di (t-butylperoxy) -cyclohexane and mixtures thereof.

Preferably, when the or peroxides of formula (I) are used in admixture with at least one different additional peroxide peroxides of formula (I), preferably selected from peroxides of formula (III), the ratio or peroxides of formula (I) and at least one different additional peroxide peroxides of formula (I), preferably selected from peroxides of formula (III) is between 99: 1 and 30: 70, preferably between 50: 50 and 99: 1, more preferably between 60: 40 and 80: 20.

The composition according to the invention may also comprise one or more photoinitiators such as those selected from the derivatives of acetophenone and benzophenone.

The composition according to the invention may also comprise one or more additional monomers of allyl monomers.

The additional monomers is or are selected from acrylic monomers or methacrylic monomers such as those chosen from methyl acrylate, methyl methacrylate, phenyl methacrylate, vinyl acetate isophthalate iso allyl, diallyl terephthalate and diallyl adipate.

The composition according to the invention may also comprise at least one pigment and / or at least one organic co lorant, that is to say at least one coloring agent.

In this case, the composition may also comprise at least one dispersing agent operative to disperse the pigment in said composition.

According to a preferred embodiment, the composition comprises the diéthylèneglyco the bis (allyl carbonate) and 1-methoxy-1-tert-amylperoxycyclohexane and at least one pigment and / or organic co lorant and optionally at least one dispersant.

Preferably, the coloring agent is a pigment.

The pigment may be present in the composition may be organic or inorganic.

Among the inorganic pigments, mention may be made of inorganic pigments which can optionally be surface treated.

Or the inorganic pigments are preferably selected from titanium oxides, especially titanium dioxide, iron oxides such as red iron oxide, iron oxide ell j, and zirconium oxides.

Organic pigments may be selected from phthalocyanine blue, phthalocyanine green, the chromophtal vio let and green oxidized chromophtal.

Among the pigments, there may be mentioned pigments phthalocyanines, especially copper phthalocyanines pigments, especially phthalocyanine pigment blue copper, and iron oxides.

According to one embodiment, the pigments are inorganic. Advantageously, the pigments are organic.

The composition according to the invention is in particular a liquid at room temperature, that is to say liquid at a temperature between 10 ° C and 30 ° C, preferably between 15 ° C and 25 ° C.

The composition according to the invention as defined above is a composition inch lymérisable, that is to say that it is likely to be polymerized under the action of heat, in particular to at least a temperature ranging from 40 to 140 ° C.

The invention also relates to the use of the polymerizable composition as defined above for the manufacture of an organic glass, preferably an ophthalmic lens may be tinted using pigments and / or organic dyes.

Preferably, the composition according to the invention may comprise a release agent such as Zelec® UN.

organic glass

The polymerizable composition according to the invention results after curing in a plastic lens.

Thus, the present invention also relates to an organic glass obtained from the polymerization of a composition as previous defined.

More specifically, the invention also relates an organic glass obtained from the radical polymerization of a composition as defined above.

The organic glass is preferably selected from the windows of instruments or optical detectors or ophthalmic lenses.

Preferably, the organic glass is selected from ophthalmic lenses.

Within the meaning of the present invention, the ophthalmic term means a drink capable of being mounted in bezel and whose function is to protect the eyes, in particular against sun, including ultravio lets rays (glass so lar), or correct vision. In the latter case, the ophthalmic lens is preferably afocal, unifocal, bifocal, trifocal or progressive.

And the ophthalmic lens may be of Multifunction Multifunction callus or progressive or degressive cal, that is to say of Multifunction variable power lens spacers.

The ophthalmic lens obtained can be covered with a coating or be treated at its surface.

Advantageously, the invention relates to an ophthalmic lens derived from polymerizing a composition as defined above.

According to one embodiment, the ophthalmic lens is obtained from the polymerization of a composition consisting of 1 -methoxy-1-tert-amylperoxycyclohexane and at least one allyl monomer selected from monomers bis (allyl carbonate) dio l formula (II) as described above.

Preferably, the ophthalmic lens is obtained from the polymerization of a composition consisting of 1 -methoxy-1-tert-amylperoxycyclohexane and diéthylèneglyco the bis (allyl carbonate).

According to one embodiment, the organic glass is chosen from tinted ophthalmic lenses with one or more pigments and / or organic co lorants.

According to this mo embodiment, the ophthalmic lens is preferably obtained from the polymerisation of a composition comprising 1-methoxy-1-tert-amylperoxycyclohexane and at least one allyl monomer selected from monomers bis (allyl carbonate) diol of formula (II), as described above, and one or more pigments and / or organic dyes.

More specifically, the ophthalmic lens is preferably obtained from the polymerisation of a composition comprising 1-methoxy-1-tert-amylperoxycyclohexane, the diéthylèneglyco the bis (allyl carbonate) and one or more pigments and / or organic dyes.

Product of the polymerizable composition

Another object of the present invention relates to the product obtained by po lymérisation of one or more allyl monomers and / or one or more copolymers allyl in the presence of one or more peroxides of formula (I).

Thus the product is a polymer composition (or a polymer product) resulting from the po lymérisation of one or more allyl monomers and / or one or more copolymers allyl in the presence of one or more peroxides of formula (I).

Po lymère composition is derived from the polymerization of the polymerizable composition as defined above and more specifically the various constituents of the polymerizable composition.

In other words, the polymer composition corresponds to a resin that can serve as base material for manufacturing any type of object that is used for its good mechanical and optical properties, including its optical properties.

Preferably, the polymer product or polymer composition can be shaped so as to obtain an organic glass or another object used for its good mechanical and optical properties, including transparency and low co loration or its colorless nature.

The polymer composition is particularly in the form so lide at room temperature, that is to say so lide at a temperature between 10 ° C and 30 ° C, preferably between 15 ° C and 25 ° C.

A process for preparing the polymer composition

Similarly, the invention also relates to a process for preparing the polymer composition as defined above, comprising at least a step of polymerizing a polymerizable composition as defined above to one or more temperatures ranging from 40 at 140 ° C, preferably from 50 to 130 ° C, more preferably from 60 to 130 ° C.

organic glass of the preparation method

The process for the preparation of an organic glass comprises at least a step of polymerizing a composition, as defined above, to one or more temperatures ranging from 40 to 140 ° C, preferably from 50 to 130 ° C, more preferably from 60 to 130 ° C, in a device comprising at least one mold.

According to a mo embodiment, the organic glass of the preparation process comprises at least the following steps:

- a step of introducing a polymerizable composition as defined above, in a device comprising at least one mold,

- a step of polymerization of said composition at one or more temperatures ranging from 40 to 140 ° C, preferably from 50 to 130 ° C, more preferably from 60 to 130 ° C; preferably, the polymerization step is a sequence of steps at different temperatures to control the removal and polymerization,

- an organic glass recovery step.

According to this mo embodiment, the step of introducing is a step of casting or inj ection of the polymerizable composition according to the invention in a device comprising at least one mold.

The device may comprise at least one mold having a complex geometry, for example a bi-p lan mold, a mold having a concave portion and a convex portion or a concave-shaped mold.

Preferably, the device comprises at least one mold having at least one concave portion and at least one convex portion.

More generally, the device comprises at least one mold whose geometrical shape has the final geometry of the desired organic glass.

The device may also comprise at least one mold having a face having a geometry corresponding to the final geometry of the desired organic glass and another face which is not regulated according to the final geometry of the organic glass but which allows

preparing a second side of the organic glass which can then be processed.

Preferably, the step of introducing comprises pouring the polymerizable composition between two molds having the required surface geometries, e.g., a mold having a concave and a mold having a convex shape.

According to the embodiment, the composition preferably comprises at least one peroxide of the formula (I), at least an allylic monomer selected from monomers bis (allyl) dio l of formula (II) and at least one pigment and / or at least one organic co lorant.

According to this embodiment, the composition may comprise at least one dispersing agent.

The polymerization step is in particular a radical polymerization.

The polymerization step can be carried out by performing the steps of heat treatment in a temperature range varying from 40 to 140 ° C, preferably from 50 to 130 ° C, more preferably from 60 to 130 ° C for a sufficient time to conduct the polymerization, in particular periods of up to 1 0 hours to 30 hours.

Thus the temperature may be gradually increased during the polymerization step.

The polymerization step makes it possible to yield the desired organic glass.

The organic glass of the preparation process may comprise, after the step of polymerization, an organic glass of the annealing step to remove any residual stresses in the glass. The annealing step may be conducted at temperatures ranging from 60 to 130 ° C preferably 70 to 100 ° C and this for a period ranging from 1 hour to 20 hours.

The organic glass of the recovery step may be a step of opening the mold and collect the organic glass.

Thus, the organic glass of the preparation process preferably comprises a step of casting or inj ection of the composition according to the invention in a device comprising at least one mold having a complex geometry, for example a bi-p mold lan , a mold having a concave portion and a convex portion or a concave-shaped mold, preferably a mold having at least one concave portion and at least one convex portion, a step of closing the mold, a step of polymerizing the composition as defined above, and a step of opening the mold and co llecter organic glass.

The process according to the invention makes it possible to prepare an ophthalmic lens as described above.

The organic glass obtained as a result of this preparation process may undergo any type of treatment such as surface treatments to improve its mechanical and optical properties or its wettability.

According to one embodiment, as described above, the polymerizable composition according to the invention may further comprise at least one coloring agent, preferably at least one pigment and / or at least one organic dye.

Alternatively, the organic glass of the preparation process according to the invention may comprise an additional step of adding at least one coloring agent, preferably at least one pigment, after obtaining the organic glass, that is to say after the polymerization step.

The organic glass obtained as a result of this process has good mechanical and optical properties.

The optical quality plastic lenses according to the invention can be assessed by determining in particular the at least one of the following:

- the 'index of refraction (n D 2 O) to make a réfractomètre Abbe (méthode standardisée ASTM D-542),

- the yellow index (YI) which is obtained by spectroscopically (standardized method ASTM D-1925-63) using a Macbeth spectrophotometer 1500 More using the following equation:

YI = 100 / Y (1.277X-1,06Z)

Equation wherein X, Y and Z are the trichromatic coordinates of the sample, measured by the spectrophotometer over the entire spectrum between 380 and 780 nanometers, or with a spectro-colorimeter manufacturer X RITE type SP60, according to CIE 1976 standard.

Preferably, the yellowness index YI is obtained with a Spectro-colorimeter manufacturer X-RITE type SP60, according to CIE Standard 1976.

Preferably the yellowness index YI of the organic glass according to the invention, according to the CIE 1976 standard, is between -10 and +10, and still preferably between -5 and 5 and most preferably between - 1 and 2.

- The haze value (Haze) that can be determined according to ASTM D 1003 standard.

Preferably, the haze value of the organic glass according to the invention is less than 5, and more preferably less than 1, and even more preferably less than 0.5.

The mechanical properties of organic glasses according to the invention can be evaluated by determining including at least the following parameters:

- Rockwell hardness measured by using a Rockwell hardness machine (standardized method ASTM D-785),

- Shore Hardness D (ASTM D 2240 standard method, BS

903 Part A26).

Preferably, the organic glass of the Shore D hardness according to the invention is greater than 65.0.

- modulus of elasticity, or

- the friction coefficient.

The following examples serve to illustrate the invention without being limiting in nature.

EXAMPLES

A. Synthesis Example 1-methoxy-1-t-amylperoxycyclohexane (TAPMC)

A mixture of t-amyl hydroperoxide (TAHP), cyclohexanone and the methano that is treated by means of 70% sulfuric acid at a temperature between -6 ° C and -4 ° C.

In fifteen minutes, an equilibrium mixture of 1-methoxy-1-t-amylperoxycyclohexane, 1, 1 -di (t-amylperoxy) - cyclohexane and starting materials unreacted, cyclohexanone and TAHP, forms.

A small amount (about 2%) of cyclohexane-1, 1 -diméthoxycétal (CDMK) is also obtained in the reaction mixture.

The reaction mixture is treated with cold water, then the aqueous phase is separated from the organic phase, which is purified by rinsing.

This method of manufacturing the main initiator of the process according to the invention is given here by way of example, it being understood that those skilled in the art can optionally be obtained by other means well known to the skilled person . Moreover, it should be noted that organic peroxides belonging to the same family (close or very close TAPMC) were carried out and showed the same technical effects obtained in the framework of the present invention, namely for the polymerization of allyl monomers and / or allyl copolymer.

B. Example of preparing a curable composition

a polymerizable composition was prepared based on diethylene glyco the bis (allyl carbonate) (CAS 142-22-3) sold under the trademark CR-39® by PPG and 1-methoxy-1-t-amylperoxycyclohexane (TAPMC ). The composition comprises

preferably a release agent, such as Zelec® A, available from the Stepan Company.

1-methoxy-1-t-amylperoxycyclohexane is present at a content of 4% by weight based on the weight of diethylene glyco the bis (allyl carbonate).

C. Preparation Example of an organic glass

Then flowing the composition obtained above in a mold having a concave portion and a convex portion. Once casting is closed the convex portion to the concave portion of the mold followed by heating the assembly to a temperature of 90 ° C. Several steps in bearings or temperature gradients from 60-1 30 ° C. were performed for a period of 10 to 30h.

The product thus obtained inch lymérisé is annealed for a period ranging from 1 to 20 hours at temperatures ranging up to 130 ° C.

then recovering the organic glass.

Organic glass having good optical and mechanical properties in accordance with at least one of the previously described parameters.

D. biplane system for measuring optical properties

Different optical properties, namely a yellowing index (YI), a haze measurement (Haze) and a Shore D hardness were measured for different organic glasses. These organic glasses were prepared according to the protocol described above, except the polymerization was carried out between flat glass plates of 10 * 15 cm thickness 4 mm, arranged vertically, separated by a seal silicone rubber of 4 mm in diameter, the mechanical cohesion of the assembly being carried out by a collet

constant pressure. All tests were performed with a snorkel mold top.

The yellowness index YI is obtained with a Spectro-colorimeter manufacturer X-RITE type SP60, according to CIE 1976 standard (color channel). The tri-color coordinates are those of Hunter Lab. Calibrating the measurement is performed each day with a standard calibration plate (white and black), serial number: 20609 D65: WO 10 ° 18/02/2010 A89274.

The YI measurement was performed in their glass thickness of 4 mm and is expressed by difference from the YI measured on the white area of ​​the card Leneta Form 2A (including the measurement of yellowness index is 10.48 after calibration of the spectrophotometer) .

haze value (Haze), is determined using a Hazemeter: Haze-Gard plus instrument, BYK-GARDNER manufacturer, according to ASTM D 1003 (Standard Calibration (zero) No. 4733 -Calibration clarity No. 4732).

The Shore D hardness was measured using a durometer portable type HPE II Shore D (Manufacturer: BAREISS, apparatus standard NF T51-174; DIN EN ISO 868, ISO 7619, ASTM D 2240; BS 903 Part A26).

The following organic peroxides were tested:

- bisisopropyle peroxydicarbonate (CAS 105-64-6) at 27% weight in the CR-39®, sold by Arkema under the name Luperox® IPP27 (Comparative Example 1);

- 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC) as sold under the trade name Luperox ®V10 by the Company

Arkema (example 2 according to the invention);

a mixture of 70 wt% 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC) and 30%> by weight of l, l-di (tert-butylperoxy) -3,3,5-trimethylcyclohexane as sold under the

tradename Luperox Luperox ®V10 and ®231 by Arkema (Example 3 according to the invention);

a mixture of 70 wt% 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC) and 30% by weight of l, l-di (tert-amylperoxy) -cyclohexane as sold under the trade name Luperox Luperox ®V10 and ®531M60 by Arkema (example 4 according to the invention);

O O-tert-amy 1-0- (2 -Ethylhexyl) -monoperoxy carbonate sold by Arkema under the name Luperox® TAEC (Comparative Example 5);

OO-tert-butyl LO- (2 -Ethylhexyl) -monoperoxy carbonate sold by Arkema under the name Luperox® TBEC (Example 6 comparative).

The thermal cure cycle is adapted depending on the decomposition temperature of the organic peroxides used (half-life temperatures (HLT) for lh and LOH) according to the following scheme: 14h mounted to the temperature of half-life lOh (HLT lOH) of the peroxide used (in the case of a mixture of peroxides, to the HLT lOh peroxide having the HLT lOh Highest either for example 3, that of Luperox 231, and example 4 that of Luperox 531M60), then mounted in 4 h at the HTL to a temperature of half life at lh (HLT lh) of the peroxide used (in the case of a mixture of peroxides, until HLT lh peroxide having the HLT lh Highest is for example 3, that of Luperox 231, and example 4 that of Luperox 531M60), then cooling to 70 ° C, temperature at which is formed the mold.

The results are presented in the table below:

+ Plates showing no fracture to release. The silicone gasket has always been removed plates without exhibiting area of ​​removal.

* Sometimes broken plates in the mold, slight adhesion to the joint, without tearing the seal during its removal by manual traction.

** Plates always very brittle to mold, adherent silicone seal, cut-away material during manual release of the joint after release.

Active oxygen% is expressed as follows: A [0] = n *

16 * titre (%) / Mw, where n = number of peroxides functions present in the peroxide molecule, 16 is the molecular weight in g / mole of the oxygen atom and Mw is the molecular weight in g / mole of the peroxide .

Note that the use of TAPMC at significantly higher temperature compared to the reference made with IPP27 hardly alters the yellowness index.

It is also noted that active oxygen content equivalent to Example 1, (around 0.23%), the compositions of Examples 3 and 4 do not alter significantly the value of YI despite a temperature again more higher than for example 1, and allows a higher hardness, however, leading to brittle plates releasability.

We also note that at lower dosage corresponding to an A [0] 0,12- around 0.13%, the addition of a cyclic difunctional peroxide according to the invention (Example 3) or perkétal tert-amyl (example 4) can approach a hardness similar to that of example 1.

Examples 5 and 6, it can be concluded that the mono tert-amyl percarbonate Luperox® TAEC and the mono tert-butyl percarbonate Luperox® TBEC result in plates which have a yellowness index YI much higher compared to the reference of the example 1 and examples 2 to 4. in addition, for example 6, in spite of a comparable hardness to that of example 5, the plates break upon demolding after curing and the plate can not be detached easily from the seal tears partly.

Examples 5 and 6 thus show that the use of percarbonate peroxides does not form plaques good yellowness index YI, low haze and high hardness without that it is not accompanied by breaking the mold .

CLAIMS
1. Use of one or more peroxides of formula (I):
1 -alcoxy- 1 -t-alkylperoxycyclohexane
(I)

Formula (I) wherein the alkoxy group comprises 1 to 4 carbon atoms, the group t-alkyl contains from 4 to 12 carbon atoms, and the cyclohexane ring is optionally substituted with 1 to 3 alkyl groups each having from 1 to 3 carbon atoms;

for polymerizing one or more allyl and / or copolymers of allylic monomers.

2. Use according to Claim 1, characterized in that the or peroxides of formula (I) is or are selected from 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC), 1-methoxy-1-t-butylperoxycyclohexane (TBPMC), 1-methoxy-1-t-amylperoxy-3, 3, 5 -triméthylcyclohexane, the l -methoxy-l -t-butylperoxy-3, 3, 5 -triméthylcyclohexane, 1 -ethoxy- 1 -t -amylperoxycyclohexane (Tāpēc), 1 -ethoxy-1-t-butylperoxycyclohexane (TBPEC), 1 -ethoxy-l -t-amy the peroxy-3, 3, 5 -trimethylcyclohexane and / or 1-ethoxy-1 - t-butyl peroxides the 3, 3, 5 -trimethylcyclohexane.

3. Use according to claim 1 or 2, characterized in that the peroxide of formula (I) is 1-methoxy-1-tert-amylperoxycyclohexane.

4. Use according to any one of the preceding claims, characterized in that the allyl or monomers is or are selected from monomers bis (allyl carbonate).

5. Use according to any one of the preceding claims, characterized in that the allyl or monomers is or are selected from monomers bis (allyl carbonate) of the dio of formula (II):

OO

R a - O-C-O-R- O-C-O-R c

Formula (II) wherein:

• R a and R c , identical or different, represent an allyl group of the following formula:

- C CH ^

Formula wherein Rd is selected from:

- a hydrogen atom,

- a halogen atom, preferably a fluorine or chlorine atom,

- an alkyl group, linear or branched C 1 - C 4,

• Rb is selected from alkylene groups, ether groups alkylene, ether groups of aromatic alkylene polyether groups alkylene, carbonate groups alkylene and mixtures thereof.

6. Use according to any one of the preceding claims, characterized in that the or allyl monomer is selected from the éthylèneglyco bis allyl carbonate, diethylene glyco the bis 2-methyl carbonate, diéthylèneglyco the bis (allyl carbonate) the éthylèneglyco the bis (2-chloro allyl carbonate), triéthylèneglyco the bis (allyl carbonate), 1, 3 -propanedio the bis (allyl carbonate), propylene glyco the bis (2-ethyl allyl carbonate), 1, 3 -butènedio the bis (allyl carbonate), 1, 4-butenedio the bis (2-bromo allyl carbonate), dipropylèneglyco the bis (allyl carbonate), triméthylèneglyco the bis (2-ethyl allyl carbonate), pentaméthylèneglyco the bis (allyl carbonate), isopropylene bis pheno bis (allyl carbonate) and mixtures thereof.

7. Use according to any one of the preceding claims, characterized in that the allyl monomer is selected from diéthylèneglyco the bis (allyl carbonate).

8. Use according to any one of the preceding claims, characterized in that the copolymers or the allyl is or are obtained from the po lymérisation monomers bis (allyl carbonate) of the dio as defined according to claim 5 or 6 .

9. Use according to any one of the preceding claims, characterized in that the allyl or copolymers is or are chosen from poly (allyl carbonates) of polyo l.

10. Use according to any one of the preceding claims, characterized in that the allyl or copolymers is or are obtained (s) from the polymerization of a monomer bis (allyl) carbonate and a polyether diol.

January 1. polymerizable composition comprising at least one peroxide of the formula (I) as defined according to any one of claims 1 to 3 and at least one allyl monomer as defined according to any one of claims 1, 6 and 7, and / or at least one allyl copolymer as defined according to any one of claims 1, 8 to 10.

12. Composition according to claim 1 1, characterized in that it further comprises at least one additional different peroxide peroxides of formula (I), preferably selected from peroxides of formula (III):

bis-t-alkylperoxycyclohexane (III)

Formula (III) wherein each t-alkyl group comprises from 4 to 12 carbon atoms and the cyclohexane ring is optionally substituted with 1 to 3 alkyl groups each having 1 to 3 carbon atoms, preferably, the peroxide of formula (III) is selected from the group consisting of l, l-di (tert-butylperoxy) -3, 3, 5 -trimethylcyclohexane, 1, 1 -di (tert-amyl peroxy) cyclohexane, the l, l -di (t-butylperoxy) -cyclohexane and mixtures thereof.

13. The composition of claim 12, wherein the ratio or the peroxides of formula (I) and at least one additional different peroxide peroxides of formula (I), preferably selected from peroxides of formula (III) is between 99: 1 and 30: 70, preferably between 50: 50 and 99: 1, more preferably between 60: 40 and 80: 20.

14. Composition according to any one of the preceding claims, characterized in that it further comprises at least one photoinitiator, preferably selected from the derivatives of acetophenone and benzophenone.

15. Use of the composition as defined according to one of claims 1 1 to 14 for the manufacture of an organic glass, preferably an ophthalmic lens.

16. Composition inch lymère characterized in that it is obtained by polymerizing the polymerizable composition as defined according to any one of claims 1 1 to 14.

17. Organic glass obtained by polymerization of a polymerizable composition as defined according to any one of claims 1 1 to 14.

1 8. The organic glass according to claim 17, characterized in that it is selected from the windows of instruments or optical detectors or ophthalmic lenses.

19. The organic glass according to claim 1 8, characterized in that it is chosen from tinted ophthalmic lenses with one or more pigments and / or organic dyes.

20. A method of preparing a polymer composition as defined in claim 16, characterized in that it comprises at least one stage of polymerization of a polymerizable composition as defined according to any one of claims 1 1 to 14, to one or more temperatures ranging from 40 to 140 ° C, preferably from 50 to 130 ° C, more preferably from 60 to 130 ° C.

21. Process for the preparation of an organic glass comprising at least the following successive steps:

- a step of introducing a polymerizable composition as defined according to any one of claims 1 1 to 14 in a device comprising at least one mold,

- a polymerization of said composition of step to one or more temperatures ranging from 40 to 140 ° C, preferably from 50 to 130 ° C, more preferably from 60 to 130 ° C,

an organic glass recovery step.

Documents

Application Documents

# Name Date
1 201917009115-RELEVANT DOCUMENTS [26-06-2023(online)].pdf 2023-06-26
1 201917009115.pdf 2019-03-08
2 201917009115-IntimationOfGrant03-02-2022.pdf 2022-02-03
2 201917009115-STATEMENT OF UNDERTAKING (FORM 3) [08-03-2019(online)].pdf 2019-03-08
3 201917009115-PRIORITY DOCUMENTS [08-03-2019(online)].pdf 2019-03-08
3 201917009115-PatentCertificate03-02-2022.pdf 2022-02-03
4 201917009115-FORM 1 [08-03-2019(online)].pdf 2019-03-08
5 201917009115-FIGURE OF ABSTRACT [08-03-2019(online)].pdf 2019-03-08
5 201917009115-Annexure [31-01-2022(online)].pdf 2022-01-31
6 201917009115-Response to office action [31-01-2022(online)].pdf 2022-01-31
6 201917009115-DECLARATION OF INVENTORSHIP (FORM 5) [08-03-2019(online)].pdf 2019-03-08
7 201917009115-US(14)-HearingNotice-(HearingDate-02-02-2022).pdf 2021-12-20
7 201917009115-COMPLETE SPECIFICATION [08-03-2019(online)].pdf 2019-03-08
8 201917009115-CLAIMS [11-12-2021(online)].pdf 2021-12-11
8 201917009115-certified copy of translation (MANDATORY) [03-04-2019(online)].pdf 2019-04-03
9 201917009115-FER_SER_REPLY [11-12-2021(online)].pdf 2021-12-11
9 201917009115-Proof of Right (MANDATORY) [09-04-2019(online)].pdf 2019-04-09
10 201917009115-FER.pdf 2021-10-18
10 201917009115-FORM-26 [09-04-2019(online)].pdf 2019-04-09
11 201917009115-FORM 4(ii) [14-09-2021(online)].pdf 2021-09-14
11 201917009115-Power of Attorney-100419.pdf 2019-04-16
12 201917009115-FORM 18 [23-10-2020(online)].pdf 2020-10-23
12 201917009115-OTHERS-100419.pdf 2019-04-16
13 201917009115-Correspondence-100419.pdf 2019-04-16
13 201917009115-FORM 3 [07-08-2019(online)].pdf 2019-08-07
14 201917009115-Correspondence-100419.pdf 2019-04-16
14 201917009115-FORM 3 [07-08-2019(online)].pdf 2019-08-07
15 201917009115-FORM 18 [23-10-2020(online)].pdf 2020-10-23
15 201917009115-OTHERS-100419.pdf 2019-04-16
16 201917009115-Power of Attorney-100419.pdf 2019-04-16
16 201917009115-FORM 4(ii) [14-09-2021(online)].pdf 2021-09-14
17 201917009115-FORM-26 [09-04-2019(online)].pdf 2019-04-09
17 201917009115-FER.pdf 2021-10-18
18 201917009115-FER_SER_REPLY [11-12-2021(online)].pdf 2021-12-11
18 201917009115-Proof of Right (MANDATORY) [09-04-2019(online)].pdf 2019-04-09
19 201917009115-certified copy of translation (MANDATORY) [03-04-2019(online)].pdf 2019-04-03
19 201917009115-CLAIMS [11-12-2021(online)].pdf 2021-12-11
20 201917009115-COMPLETE SPECIFICATION [08-03-2019(online)].pdf 2019-03-08
20 201917009115-US(14)-HearingNotice-(HearingDate-02-02-2022).pdf 2021-12-20
21 201917009115-DECLARATION OF INVENTORSHIP (FORM 5) [08-03-2019(online)].pdf 2019-03-08
21 201917009115-Response to office action [31-01-2022(online)].pdf 2022-01-31
22 201917009115-Annexure [31-01-2022(online)].pdf 2022-01-31
22 201917009115-FIGURE OF ABSTRACT [08-03-2019(online)].pdf 2019-03-08
23 201917009115-FORM 1 [08-03-2019(online)].pdf 2019-03-08
23 201917009115-Written submissions and relevant documents [02-02-2022(online)].pdf 2022-02-02
24 201917009115-PRIORITY DOCUMENTS [08-03-2019(online)].pdf 2019-03-08
24 201917009115-PatentCertificate03-02-2022.pdf 2022-02-03
25 201917009115-STATEMENT OF UNDERTAKING (FORM 3) [08-03-2019(online)].pdf 2019-03-08
25 201917009115-IntimationOfGrant03-02-2022.pdf 2022-02-03
26 201917009115.pdf 2019-03-08
26 201917009115-RELEVANT DOCUMENTS [26-06-2023(online)].pdf 2023-06-26

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