Sign In to Follow Application
View All Documents & Correspondence

Hair Treatment Compositions

Abstract: The composition is particularly suitable for the treatment of hair which is dry, damaged and/or prone to manageability problems. The invention claims a method of treating hair by applying to the hair a composition comprising from 0.001 to 20 wt% of the total composition of the group consisting of Cucurbitine, 2-piperazinecarboxylic acid, derivatives thereof or mixtures thereof.

Get Free WhatsApp Updates!
Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
17 April 2009
Publication Number
27/2009
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application

Applicants

HINDUSTAN UNILEVER LIMITED
HINDUSTAN LEVER HOUSE, 165-166 BACKBAY RECLAMATION, MUMBAI-400 020, INDIA.

Inventors

1. CAO QUNHUA
UNILEVER (CHINA) INVESTING COMPANY, R&D DEPARTMENT, 3/F XIN MAO BUILDING, 99 TIAN ZHOU ROAD, 200233, SHANGHAI, CHINA.
2. KHOSHDEL EZAT
UNILEVER R&D PORT SUNLIGHT, QUARRY ROAD EAST, BEBINGTON, WIRRAL, MERSEY&DE CH63 3JW, UNITED KINGDOM
3. MACKAY COLINE
UNILEVER R&D PORT SUNLIGHT, QUARRY ROAD EAST, BEBINGTON, WIRRAL, MERSEY&DE CH63 3JW, UNITED KINGDOM
4. PLANT YVONNE CHRISTINE
UNILEVER R&D PORT SUNLIGHT, QUARRY ROAD EAST, BEBINGTON, WIRRAL, MERSEY&DE CH63 3JW, UNITED KINGDOM
5. SI XIANGGUO
UNILEVER (CHINA) INVESTING COMPANY, R&D DEPARTMENT, 3/F XIN MAO BUILDING, 99 TIAN ZHOU ROAD, 200233, SHANGHAI, CHINA.
6. YANG MING
UNILEVER (CHINA) INVESTING COMPANY, R&D DEPARTMENT, 3/F XIN MAO BUILDING, 99 TIAN ZHOU ROAD, 200233, SHANGHAI, CHINA.

Specification

J3841/C
FORM - 2
THE PATENTS ACT, 1970
(39 of 1970)
&
The Patents Rules, 2003


COMPLETE SPECIFICATION
(See Section 10 and Rule 13)
HAIR TREATMENT COMPOSITIONS

HINDUSTAN UNILEVER LIMITED, a company incorporated under
the Indian Companies Act, 1913 and having its registered office
at 165/166, Backbay Reclamation, Mumbai -400 020, Maharashtra, India
The following specification particularly describes the invention and the manner in which it is to be performed


WO 2008/046753

PCTVEP2007/060638

- 1 -
HAIR TREATMENT COMPOSITIONS
FIELD OF THE INVENTION
5 The present invention relates to hair treatment compositions which can be used to repair dry, damaged hair.
BACKGROUND AND PRIOR ART
10 Hair can suffer damage from a number of sources. For example, environmental sources of hair damage include exposure to UV light and chlorine. Chemical sources of hair damage include treatments such as bleaching, perming and straightening, and overly frequent washing with harsh
15 surfactant-based cleansing shampoo compositions. Mechanical sources of hair damage include excessive brushing and combing and prolonged use of heated appliances for drying and styling the hair.
20 Damage to the hair typically manifests itself in cuticle and protein loss from the hair fibre, hair fibre dryness, hair fibre brittleness and breakage and frayed or split ends.
Various organic molecules and combinations thereof have been 25 suggested for use in the treatment of dry, damaged and/or unmanageable hair.
WO 2004054526 and WO 2004054525 describes hair treatment compositions for the care and repair of damaged hair using 30 trehalose.
1 7 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 2 -
WO 2004006874 describes hair treatment compositions for repairing and preventing the principal symptoms of damaged hair, comprising specific branched amine and/or hydroxy compounds (in particular 3,3-dimethyl-l,2-butanediol). 5
US 5 637 997 and US 5 714 164 dicloses Cucurbitine or extracts of Cucunitacea for dermatoligicl compositions having an antiallergic acitivity.
10 The present inventors have found that hair treated with
compositions comprising Cucurbitine/derivatives thereof or extracts of Cucunitacea show improved efficacy in the repair of damaged hair.
15 Such compositions are also helpful in preventing scalp itch.
SUMMARY OF THE INVENTION
The present invention provides a method of treating hair by 20 applying to the hair a composition comprising from 0.001 to 20 wt% of the total composition from the group consisting of Cucurbitine, 2-piperazinecarboxylic acid, derivatives thereof or mixtures thereof.
25 The invention also provides the use of the above composition in the treatment of dry, damaged and/or unmanageable hair.
The invention also provides for the use of Cururbitine, 2-piperazinecarboxylic acid or derivatives thereof in the 30 preparation of a hair treatment composition
17 APR 2009

WO 2008/046753

PCT7EP2007/060638

- 3 -
A further embodiment of the invention is the use of Cucurbitine or 2-piperazinecarboxylic acid to prevent or mitigate damage to hair and/orto mitigate scalp itch.
5 DETAILED DESCRIPTION AND PREFERRED EMBODIMENTS
Cucurbitine
Cucurbitine, or 3-amino-3-pyrrolidinecarboxylic acid, of the 10 following is a natural, water-soluble amino acid found in Cucurbitaceae (see V. H. Mihranian et al., LLOYDIA (1968), 31 (1) 23-29).
Cucurbitine may be obtained by means of extraction in 15 laevorotatory form, or synthetically in racemic form. Among
the various methods of synthesis of cucurbitine, special
mention may be made of the synthesis method of H. J.
Monteiro, J. Chem. Soc., Chem. Commun. (1973) 2.
Another synthesis method enables the two optical isomers of 20 cucurbitine to be obtained separately. This is the method of
Morimoto et al., Chem. Pharm. Bull. (1987) 35 (9) 3845-3849,
which is a stereospecific enzymatic method of synthesis by
the use of a pig liver esterase.
Further synthetic methods of preparing cucurbitine are 25 described in Bull. Korean Chem Soc.2000, vol. 21. No.l and
US 5 714 164.
Cucurbitine may be used either in free form, or in the form of one of its cosmetically or pharmaceutically, in 30 particular dermatologically, acceptable salts or esters. The abovementioned salts and esters may be prepared by
1 7 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 4 -
conventional processes which are well known to a person skilled in the art. Among salts, the mono- and dihydrobromide and the mono- and dihydrochloride are preferred. Among esters, the methyl ester and the ethyl 5 ester are preferred.
According to an advantageous variant, the abovementioned may be in the form of a plant extract containing cucurbitine. Extracts of Cucurbita maxima Duch., of Cucurbita pepo L. or 0 of Cucurbita moschata Duch are advantageous; particularly, an extract of pips or of fruit pulp.
Especially advantageous sources of the laevorotatory cucurbitine are the pulp and pips of Cucurbitaceae, 5 preferably of the species Cucurbita pepo L., Cucurbita maxima Duch. and Cucurbita moschata Duch.
Of particular use for this invention is an isomer of Cucurbitine known as 2-piperazinecarboxylic acid. 0
The level of cucurbitine or derivatives thereof is from 0.001 to 20 wt%, preferably from 0.05% to 10wt%, and more preferably 0.1 to 5%, by weight of the total composition.
5 Cucurbitine and/or derivatives thereof may be used in a cosmetically acceptable excipient, vehicle or carrier.
17 APR 2009

WO 2008/046753

PCT7EP2007/060638

- 5 -
Product Form
Hair treatment compositions according to the invention may suitably take the form of shampoos, conditioners, sprays, 5 mousses, gels, waxes or lotions.
Particularly preferred product forms are shampoos, post-wash conditioners (leave-in and rinse-off) and hair treatment products such as hair oils and lotions. 10
Shampoo Compositions
Shampoo compositions of the invention are generally aqueous, i.e. they have water or an aqueous solution or a lyotropic 15 liquid crystalline phase as their major component.
Suitably, the shampoo composition will comprise from 50 to 98%, preferably from 60 to 90% water by weight based on the total weight of the composition. 20
Anionic Cleansing Surfactant
Shampoo compositions according to the invention will generally comprise one or more anionic cleansing surfactants 25 which are cosmetically acceptable and suitable for topical application to the hair.
Examples of suitable anionic cleansing surfactants are the alkyl sulphates, alkyl ether sulphates, alkaryl sulphonates, 30 alkanoyl isethionates, alkyl succinates, alkyl
sulphosuccinates, alkyl ether sulphosuccinates, N-alkyl
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 6 -
sarcosinates, alkyl phosphates, alkyl ether phosphates, and alkyl ether carboxylic acids and salts thereof, especially their sodium, magnesium, ammonium and mono-, di- and triethanolamine salts. The alkyl and acyl groups generally 5 contain from 8 to 18, preferably from 10 to 16 carbon atoms and may be unsaturated. The alkyl ether sulphates, alkyl ether sulphosuccinates, alkyl ether phosphates and alkyl ether carboxylic acids and salts thereof may contain from 1 to 20 ethylene oxide or propylene oxide units per molecule.
10
Typical anionic cleansing surfactants for use in shampoo compositions of the invention include sodium oleyl succinate, ammonium lauryl sulphosuccinate, sodium lauryl sulphate, sodium lauryl ether sulphate, sodium lauryl ether
15 sulphosuccinate, ammonium lauryl sulphate, ammonium lauryl ether sulphate, sodium dodecylbenzene sulphonate, triethanolamine dodecylbenzene sulphonate, sodium cocoyl isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid and sodium N-lauryl sarcosinate.
20
Preferred anionic cleansing surfactants are sodium lauryl sulphate, sodium lauryl ether sulphate (n)EO, (where n is from 1 to 3), sodium lauryl ether sulphosuccinate{n)EO, (where n is from 1 to 3), ammonium lauryl sulphate, ammonium
25 lauryl ether sulphate(n)EO, (where n is from 1 to 3), sodium cocoyl isethionate and lauryl ether carboxylic acid (n) EO (where n is from 10 to 20).
Mixtures of any of the foregoing anionic cleansing 30 surfactants may also be suitable.
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 7 -
The total amount of anionic cleansing surfactant in shampoo compositions of the invention generally ranges from 0.5 to 45%, preferably from 1.5 to 35%, more preferably from 5 to 20% by total weight anionic cleansing surfactant based on 5 the total weight of the composition.
Co-surfactant
The composition can include co-surfactants, to help impart 10 aesthetic, physical or cleansing properties to the composition.
An example of a co-surfactant is a nonionic surfactant, which can be included in an amount ranging from 0.5 to 8%, 15 preferably from 2 to 5% by weight based on the total weight of the composition.
For example, representative nonionic surfactants that can be included in shampoo compositions of the invention include 20 condensation products of aliphatic (C8 - Cis) primary or
secondary linear or branched chain alcohols or phenols with alkylene oxides, usually ethylene oxide and generally having from 6 to 30 ethylene oxide groups.
25 Other representative nonionic surfactants include mono- or di-alkyl alkanolamides. Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.
Further nonionic surfactants which can be included in shampoo 30 compositions of the invention are the alkyl polyglycosides (APGs). Typically, the APG is one which comprises an alkyl
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 8 -
group connected (optionally via a bridging group) to a block of one or more glycosyl groups. Preferred APGs are defined by the following formula:
5 RO - (G)n
wherein R is a branched or straight chain alkyl group which may be saturated or unsaturated and G is a saccharide group.
10 R may represent a mean alkyl chain length of from about C5 to about C20. Preferably R represents a mean alkyl chain length of from about C3 to about C12. Most preferably the value of R lies between about 9.5 and about 10.5. G may be selected from C5 or C6 monosaccharide residues, and is preferably a
15 glucoside. G may be selected from the group comprising
glucose, xylose, lactose, fructose, mannose and derivatives thereof. Preferably G is glucose.
The degree of polymerisation, n, may have a value of from 20 about 1 to about 10 or more. Preferably, the value of n lies from about 1.1 to about 2. Most preferably the value of n lies from about 1.3 to about 1.5.
Suitable alkyl polyglycosides for use in the invention are 25 commercially available and include for example those
materials identified as: Oramix NS10 ex Seppic; Plantaren 1200 and Plantaren 2000 ex Henkel.
Other sugar-derived nonionic surfactants which can be 30 included in compositions of the invention include the C10_C18
17 APR 2009

WO 2008/046753

PCT7EP2007/060638

- 9 -
N-alkyl (C1-C6) polyhydroxy fatty acid amides, such as the C12~ C18 N-methyl glucamides, as described for example in WO 92 06154 and US 5 194 639, and the N-alkoxy polyhydroxy fatty acid amides, such as C10-C18 N-(3-methoxypropyl) 5 glucamide.
A preferred example of a co-surfactant is an amphoteric or zwitterionic surfactant, which can be included in an amount ranging from 0.5 to about 8%, preferably from 1 to 4% by 10 weight based on the total weight of the composition.
Examples of amphoteric or zwitterionic surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines), alkyl glycinates,
15 alkyl carboxyglycinates, alkyl amphoacetates, alkyl
amphopropionates, alkylamphoglycinates, alkyl amidopropyl hydroxysultaines, acyl taurates and acyl glutamates, wherein the alkyl and acyl groups have from 8 to 19 carbon atoms. Typical amphoteric and zwitterionic surfactants for use in
2 0 shampoos of the invention include lauryl amine oxide, cocodimethyl sulphopropyl betaine, lauryl betaine, cocamidopropyl betaine and sodium cocoamphoacetate.
A particularly preferred amphoteric or zwitterionic 25 surfactant is cocamidopropyl betaine.
Mixtures of any of the foregoing amphoteric or zwitterionic surfactants may also be suitable. Preferred mixtures are those of cocamidopropyl betaine with further amphoteric or 30 zwitterionic surfactants as described above. A preferred
1 7 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 10 -
further amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.
The total amount of surfactant (including any co-surfactant, 5 and/or any emulsifier) in a shampoo composition of the
invention is generally from 1 to 50%, preferably from 2 to 40%, more preferably from 10 to 25% by total weight surfactant based on the total weight of the composition.
10 Cationic Polymers
Cationic polymers are preferred ingredients in a shampoo composition of the invention for enhancing conditioning performance.
15
Suitable cationic polymers may be homopolymers which are cationically substituted or may be formed from two or more types of monomers. The weight average (Mw) molecular weight of the polymers will generally be between 100 000 and 2
20 million daltons. The polymers will have cationic nitrogen containing groups such as quaternary ammonium or protonated amino groups, or a mixture thereof. If the molecular weight of the polymer is too low, then the conditioning effect is poor. If too high, then there may be problems of high
25 extensional viscosity leading to stringiness of the composition when it is poured.
The cationic nitrogen-containing group will generally be present as a substituent on a fraction of the total monomer 30 units of the cationic polymer. Thus when the polymer is not a homopolymer it can contain spacer non-cationic monomer
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 11 -
units. Such polymers are described in the CTFA Cosmetic Ingredient Directory, 3rd edition. The ratio of the cationic to non-cationic monomer units is selected to give polymers having a cationic charge density in the required range, which 5 is generally from 0.2 to 3.0 meq/gm. The cationic charge density of the polymer is suitably determined via the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for nitrogen determination.
0 Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamides, alkyl (meth)acrylate, vinyl caprolactone
5 and vinyl pyrrolidine. The alkyl and dialkyl substituted monomers preferably have C1-C7 alkyl groups, more preferably Cl-3 alkyl groups. Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol and ethylene glycol.
0
The cationic amines can be primary, secondary or tertiary amines, depending upon the particular species and the pH of the composition. In general secondary and tertiary amines, especially tertiary, are preferred.
5
Amine substituted vinyl monomers and amines can be polymerised in the amine form and then converted to ammonium by quaternization.
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 12 -
The cationic polymers can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
5 Suitable cationic polymers include, for example:
- cationic diallyl quaternary ammonium-containing
polymers including, for example,
dimethyldiallylammonium chloride homopolymer and
10 copolymers of acrylamide and dimethyldiallylammonium chloride, referred to in the industry (CTFA) as Polyquaternium 6 and Polyquaternium 7, respectively;
- mineral acid salts of amino-alkyl esters of homo-and
15 co-polymers of unsaturated carboxylic acids having
from 3 to 5 carbon atoms, (as described in U.S. Patent 4, 009,256);
- cationic polyacrylamides (as described in W095/22311).
20
Other cationic polymers that can be used include cationic polysaccharide polymers, such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives. 25
Cationic polysaccharide polymers suitable for use in compositions of the invention include monomers of the formula:
30
17 APR 2009

WO 2008/046753

PCTYEP2007/060638

- 13 -
wherein: A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual. R is an alkylene, oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof. R1, R2 and R3 independently 5 represent alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms. The total number of carbon atoms for each cationic moiety (i.e., the sum of carbon atoms in R1, R2 and R3) is preferably about 20 or less, and x is an anionic 10 counterion.
Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred 15 to in the industry (CTFA) as Polyquatetnium 24. These
materials are available from the Amerchol Corporation, for instance under the tradename Polymer Lfy-200.
Other suitable cationic polysaccharide polymers include 2 0 quaternary nitrogen-containing cellulose ethers (e.g. as described in U.S. Patent 3,962,418), and copolymers of etherified cellulose and starch (e.g. as described in U.S. Patent 3,958,581) .
A particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative, such as guar hydroxypropyltrimethylammonium chloride (commercially available from Rhodia in their JAGUAR trademark series). Examples of such materials are JAGUAR C13S, JAGUAR C14, JAGUAR C15, and JAGUAR C17. 25
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 14 -
Mixtures of any of the above cationic polymers may be used.
Cationic polymer will generally be present in a shampoo composition of the invention at levels of from 0.01 to 5%, 5 preferably from 0.05 to 1%, more preferably from 0.08 to 0.5% by total weight of cationic polymer based on the total weight of the composition.
Suspending Agent
10
Preferably an aqueous shampoo composition of the invention further comprises a suspending agent. Suitable suspending agents are selected from polyacrylic acids, cross-linked polymers of acrylic acid, copolymers of acrylic acid with a
15 hydrophobic monomer, copolymers of carboxylic acid-containing monomers and acrylic esters, cross-linked copolymers of acrylic acid and acrylate esters, heteropolysaccharide gums and crystalline long chain acyl derivatives. The long chain acyl derivative is desirably
20 selected from ethylene glycol stearate, alkanolamides of
fatty acids having from 16 to 22 carbon atoms and mixtures thereof. Ethylene glycol distearate and polyethylene glycol 3 distearate are preferred long chain acyl derivatives, since these impart pearlescence to the composition.
25 Polyacrylic acid is available commercially as Carbopol 420, Carbopol 488 or Carbopol 493. Polymers of acrylic acid cross-linked with a polyfunctional agent may also be used; they are available commercially as Carbopol 910, Carbopol 934, Carbopol 941 and Carbopol 980. An example of a
30 suitable copolymer of a carboxylic acid containing monomer
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 15 -
and acrylic acid esters is Carbopol 1342. All Carbopol (trademark) materials are available from Goodrich.
Suitable cross-linked polymers of acrylic acid and acrylate 5 esters are Pemulen TR1 or Pemulen TR2. A suitable
heteropolysaccharide gum is xanthan gum, for example that available as Kelzan mu.
Mixtures of any of the above suspending agents may be used. 10 Preferred is a mixture of cross-linked polymer of acrylic acid and crystalline long chain acyl derivative.
Suspending agent will generally be present in a shampoo composition of the invention at levels of from 0.1 to 10%, 15 preferably from 0.5 to 6%, more preferably from 0.9 to 4% by total weight of suspending agent based on the total weight of the composition.
Conditioner Compositions 20
Conditioner compositions will typically comprise one or more cationic conditioning surfactants which are cosmetically acceptable and suitable for topical application to the hair.
25 Preferably, the cationic conditioning surfactants have the formula N+(R1) (R2) (R3) (R4) , wherein R1, R2, R3 and R4 are independently (C1 to C30) alkyl or benzyl.
Preferably, one, two or three of R1, R2, R3 and R4 are 30 independently (C4 to C30) alkyl and the other R1, R2, R3 and R4 group or groups are (C1-C6) alkyl or benzyl.
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 16 -
More preferably, one or two of R1, R2, R3 and R4 are independently {C5 to C30) alkyl and the other R1, R2, R3 and R"3 groups are (C1-C5) alkyl or benzyl groups. Optionally, the alkyl groups may comprise one or more ester (-OCO- or -COO-) 5 and/or ether (-0-) linkages within the alkyl chain. Alkyl groups may optionally be substituted with one or more hydroxyl groups. Alkyl groups may be straight chain or branched and, for alkyl groups having 3 or more carbon atoms, cyclic. The alkyl groups may be saturated or may 10 contain one or more carbon-carbon double bonds (e.g.,
oleyl). Alkyl groups are optionally ethoxylated on the alkyl chain with one or more ethyleneoxy groups.
Suitable cationic conditioning surfactants for use in
15 conditioner compositions according to the invention include cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride,
2 0 hexadecyltrimethylarnmonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride,
2 5 dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride, dihydrogenated tallow dimethyl ammonium chloride (e.g., Arquad 2HT/75 from Akzo Nobel), cocotrimethylammonium chloride, PEG-2-oleammonium chloride and the corresponding hydroxides thereof. Further suitable cationic surfactants
30 include those materials having the CTFA designations
Quaternium-5, Quaternium-31 and Quaternium-18. Mixtures of
1 7 APR 2009

WO 2008/046753

PCTVEP2007/060638

- 17 -
any of the foregoing materials may also be suitable. A particularly useful cationic surfactant for use in conditioners according to the invention is
cetyltrimethylammonium chloride, available commercially, for example as GENAMIN CTAC, ex Hoechst Celanese. Another particularly useful cationic surfactant for use in conditioners according to the invention is behenyltrimethylammonium chloride, available commercially, for example as GENAMIN KDMP, ex Clariant.
Another example of a class of suitable cationic conditioning surfactants for use in the invention, either alone or in admixture with one or more other cationic conditioning surfactants, is a combination of (i) and (ii) below:
(i) an amidoamine corresponding to the general formula (I):

in which R1 is a hydrocarbyl chain having 10 or more 0 carbon atoms,
R2 and R3 are independently selected from hydrocarbyl chains of from 1 to 10 carbon atoms, and m is an integer from 1 to about 10; and
5 (ii) an acid.
As used herein, the term hydrocarbyl chain means an alkyl or alkenyl chain.


WO 2008/046753

PCI7EP2007/060638

- 18 -
Preferred amidoamine compounds are those corresponding to formula (I) in which
R1 is a hydrocaxbyl residue having from about 11 to about 24 5 carbon atoms,
R2 and R3 are each independently hydrocarbyl residues, preferably alkyl groups, having from 1 to about 4 carbon atoms, and
m is an integer from 1 to about 4. 10
Preferably, R2 and R3 are methyl or ethyl groups.
Preferably, m is 2 or 3, i.e. an ethylene or propylene
group. 15
Preferred amidoamines useful herein include stearamido-
propyldimethylamine, stearamidopropyldiethylamine,
stearamidoethyldiethylamine, stearamidoethyIdimethylamine,
palmitamidopropyldimethylamine, 20 palmitamidopropyldiethy1amine, palmitamidoethyldiethylamine,
palmitamidoethyldimethylamine,
behenamidopropyldimethylamine, behenamidopropyldiethylmine,
behenamidoethyldiethylamine, behenamidoethyldimethylamine,
arachidamidopropyIdimethylamine, 25 arachidamidopropyldiethylamine, arachid-
amidoethyldiethylamine, arachidamidoethyIdimethylamine, and
mixtures thereof.
Particularly preferred amidoamines useful herein are 30 stearamidopropyldimethylamine, stearamidoethyldiethylamine, and mixtures thereof.
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 19 -
Commercially available amidoamines useful herein include: stearamidopropyldimethylamine with tradenames LEXAMINE S-13 available from Inolex (Philadelphia Pennsylvania, USA) and AMIDOAMINE MSP available from Nikko (Tokyo, Japan), 5 stearamidoethyldiethylamine with a tradename AMIDOAMINE S available from Nikko, behenamidopropyldimethylamine with a tradename INCROMINE BB available from Croda (North Humberside, England)., and various amidoamines with tradenames SCHERCODINE series available from Scher (Clifton 10 New Jersey, USA).
Acid (ii) may be any organic or mineral acid which is capable of protonating the amidoamine in the hair treatment composition. Suitable acids useful herein include
15 hydrochloric acid, acetic acid, tartaric acid, fumaric acid, lactic acid, malic acid, succinic acid, and mixtures thereof. Preferably, the acid is selected from the group consisting of acetic acid, tartaric acid, hydrochloric acid, fumaric acid, and mixtures thereof.
20
The primary role of the acid is to protonate the amidoamine in the hair treatment composition thus forming a tertiary amine salt (TAS) in situ in the hair treatment composition. The TAS in effect is a non-permanent quaternary ammonium or
25 pseudo-quaternary ammonium cationic surfactant.
Suitably, the acid is included in a sufficient amount to protonate all the amidoamine present, i.e. at a level which is at least equimolar to the amount of amidoamine present in 30 the composition.
17APRZ009

WO 2008/046753

PCT/EP2007/060638

- 20 -
In conditioners of the invention, the level of cationic conditioning surfactant will generally range from 0.01 to 10%, more preferably 0.05 to 7.5%, most preferably 0.1 to 5% by total weight of cationic conditioning surfactant based on 5 the total weight of the composition.
Conditioners of the invention will typically also incorporate a fatty alcohol. The combined use of fatty alcohols and cationic surfactants in conditioning compositions is believed 10 to be especially advantageous, because this leads to the formation of a lamellar phase, in which the cationic surfactant is dispersed.
Representative fatty alcohols comprise from 8 to 22 carbon 15 atoms, more preferably 16 to 22. Fatty alcohols are
typically compounds containing straight chain alkyl groups. Examples of suitable fatty alcohols include cetyl alcohol, stearyl alcohol and mixtures thereof. The use of these materials is also advantageous in that they contribute to 20 the overall conditioning properties of compositions of the invention.
The level of fatty alcohol in conditioners of the invention will generally range from 0.01 to 10%, preferably from 0.1 to
25 8%, more preferably from 0.2 to 7%, most preferably from 0.3 to 6% by weight of the composition. The weight ratio of cationic surfactant to fatty alcohol is suitably from 1:1 to 1:10, preferably from 1:1.5 to 1:8, optimally from 1:2 to 1:5. If the weight ratio of cationic surfactant to fatty
30 alcohol is too high, this can lead to eye irritancy from the
1 7 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 21 -
composition. If it is too low, it can make the hair feel squeaky for some consumers.
Hair Oils and Lotions 5
Compositions of the invention may suitably take the form of a hair oil, for pre-wash or post-wash use. Typically, hair oils will predominantly comprise water-insoluble oily conditioning materials, such as triglycerides, mineral oil 10 and mixtures thereof.
Compositions of the invention may also take the form of a hair lotion, typically for use in between washes. Lotions are aqueous emulsions comprising water-insoluble oily 15 conditioning materials. Suitable surfactants can also be included in lotions to improve their stability to phase separation.
Silicone Conditioning Agents
20
Hair treatment compositions according to the invention, particularly water-based shampoos and hair conditioners, will preferably also contain one or more silicone conditioning agents.
25
Particularly preferred silicone conditioning agents are silicone emulsions such as those formed from silicones such as polydiorganosiloxanes, in particular polydimethylsiloxanes which have the CTFA designation
30 dimethicone, polydimethyl siloxanes having hydroxyl end groups which have the CTFA designation dimethiconol, and
17 APR 2009

WO 2008/046753

PCT7EP2007/060638

- 22 -
amino-functional polydimethyl siloxanes which have the CTFA designation amodimethicone.
The emulsion droplets may typically have a Sauter mean 5 droplet diameter (D3,2) in the composition of the invention ranging from 0.01 to 20 micrometer, more preferably from 0.2 to 10 micrometer.
A suitable method for measuring the Sauter mean droplet 10 diameter (D3,2) is by laser light scattering using an instrument such as a Malvern Mastersizer.
Suitable silicone emulsions for use in compositions of the invention are available from suppliers of silicones such as
15 Dow Corning and GE Silicones. The use of such pre-formed
silicone emulsions is preferred for ease of processing and control of silicone particle size. Such pre-formed silicone emulsions will typically additionally comprise a suitable emulsifier such as an anionic or nonionic emulsifier, or
20 mixture thereof, and may be prepared by a chemical
emulsification process such as emulsion polymerisation, or by mechanical emulsification using a high shear mixer. Pre¬formed silicone emulsions having a Sauter mean droplet diameter (D3,2) of less than 0.15 micrometers are generally
25 termed microemulsions.
Examples of suitable pre-formed silicone emulsions include emulsions DC2-1766, DC2-1784, DC-1785, DC-1786, DC-1788 and microemulsions DC2-1865 and DC2-1870, all available from Dow 30 Corning. These are all emulsions/microemulsions of
dimethiconol. Also suitable are amodimethicone emulsions such
17 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 23 -
as DC2-8177 and DC939 (from Dow Coming? and SME253 (from GE Silicones).
Also suitable are silicone emulsions in which certain types 5 of surface active block copolymers of a high molecular weight have been blended with the silicone emulsion droplets, as described for example in WO03/094874. In such materials, the silicone emulsion droplets are preferably formed from polydiorganosiloxanes such as those described 10 above. One preferred form of the surface active block copolymer is according to the following formula:

15 wherein the mean value of x is 4 or more and the mean value of y is 25 or more.
Another preferred form of the surface active block copolymer is according to the following formula: 20

wherein the mean value of a is 2 or more and the mean value 25 of b is 6 or more.
Mixtures of any of the above described silicone emulsions may also be used.
30 The above described silicone emulsions will generally be
present in a composition of the invention at levels of from
1 7 APR 2009

WO 2008/046753

PCT/EP2007/060638

- 24 -
0.05 to 10%, preferably 0.05 to 5%, more preferably from 0.5 to 2% by total weight of silicone based on the total weight of the composition.
5 Other Optional Ingredients
A composition of the invention may contain other ingredients for enhancing performance and/or consumer acceptability. Such ingredients include fragrance, dyes and pigments, pH
10 adjusting agents, pearlescers or opacifiers, viscosity modifiers, and preservatives or antimicrobials. Each of these ingredients will be present in an amount effective to accomplish its purpose. Generally these optional ingredients are included individually at a level of up to 5%
15 by weight of the total composition.
Mode of Use
Hair treatment compositions of the invention are primarily 20 intended for topical application to the hair and/or scalp of a human subject, either in rinse-off or leave-on compositions, for the treatment of dry, damaged and/or unmanageable hair. Rinse-off compositions are preferred.
25 The invention will be further illustrated by the following,
non-limiting Examples, in which all percentages quoted are by weight based on total weight unless otherwise stated.


WO 2008/046753

PCT7EP2007/060638

- 25 -
EXAMPLE
Conucurbitine was extracted from the pips of the Cucurbitaceae ( an aqueous extract of pumpkin seed Cucurbita 5 moschata Duch . The extract was separated into different fractions

Documents

Application Documents

# Name Date
1 741-MUMNP-2009- AMENDED CLAIMS.pdf 2022-11-23
1 741-MUMNP-2009_EXAMREPORT.pdf 2018-08-10
2 741-mumnp-2009-claims.doc 2018-08-10
2 741-mumnp-2009-pct-isa-210.pdf 2018-08-10
3 741-mumnp-2009-pct-ipea-416.pdf 2018-08-10
3 741-mumnp-2009-claims.pdf 2018-08-10
4 741-mumnp-2009-pct-ipea-409.pdf 2018-08-10
4 741-MUMNP-2009-CORRESPONDENCE(20-7-2010).pdf 2018-08-10
5 741-mumnp-2009-international publication report a1.pdf 2018-08-10
5 741-MUMNP-2009-CORRESPONDENCE(IPO)-(2-8-2013).pdf 2018-08-10
6 741-mumnp-2009-form 5.pdf 2018-08-10
6 741-MUMNP-2009-CORRESPONDENCE(IPO)-(24-9-2009).pdf 2018-08-10
7 741-mumnp-2009-form 3.pdf 2018-08-10
7 741-mumnp-2009-correspondence.pdf 2018-08-10
8 741-MUMNP-2009-FORM 3(4-8-2010).pdf 2018-08-10
9 741-mumnp-2009-description(complete).pdf 2018-08-10
9 741-MUMNP-2009-FORM 3(24-2-2010).pdf 2018-08-10
10 741-mumnp-2009-form 1.pdf 2018-08-10
10 741-MUMNP-2009-FORM 3(15-2-2011).pdf 2018-08-10
11 741-MUMNP-2009-FORM 18(20-7-2010).pdf 2018-08-10
11 741-mumnp-2009-form 2.pdf 2018-08-10
12 741-mumnp-2009-form 2(title page).pdf 2018-08-10
13 741-mumnp-2009-form 2(title page).pdf 2018-08-10
14 741-MUMNP-2009-FORM 18(20-7-2010).pdf 2018-08-10
14 741-mumnp-2009-form 2.pdf 2018-08-10
15 741-mumnp-2009-form 1.pdf 2018-08-10
15 741-MUMNP-2009-FORM 3(15-2-2011).pdf 2018-08-10
16 741-mumnp-2009-description(complete).pdf 2018-08-10
16 741-MUMNP-2009-FORM 3(24-2-2010).pdf 2018-08-10
17 741-MUMNP-2009-FORM 3(4-8-2010).pdf 2018-08-10
18 741-mumnp-2009-correspondence.pdf 2018-08-10
18 741-mumnp-2009-form 3.pdf 2018-08-10
19 741-mumnp-2009-form 5.pdf 2018-08-10
19 741-MUMNP-2009-CORRESPONDENCE(IPO)-(24-9-2009).pdf 2018-08-10
20 741-mumnp-2009-international publication report a1.pdf 2018-08-10
20 741-MUMNP-2009-CORRESPONDENCE(IPO)-(2-8-2013).pdf 2018-08-10
21 741-mumnp-2009-pct-ipea-409.pdf 2018-08-10
21 741-MUMNP-2009-CORRESPONDENCE(20-7-2010).pdf 2018-08-10
22 741-mumnp-2009-pct-ipea-416.pdf 2018-08-10
22 741-mumnp-2009-claims.pdf 2018-08-10
23 741-mumnp-2009-pct-isa-210.pdf 2018-08-10
24 741-MUMNP-2009_EXAMREPORT.pdf 2018-08-10
24 741-MUMNP-2009- AMENDED CLAIMS.pdf 2022-11-23