CA2372457C - Conditioning/styling terpolymers - Google Patents

Conditioning/styling terpolymers Download PDF

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Publication number
CA2372457C
CA2372457C CA2372457A CA2372457A CA2372457C CA 2372457 C CA2372457 C CA 2372457C CA 2372457 A CA2372457 A CA 2372457A CA 2372457 A CA2372457 A CA 2372457A CA 2372457 C CA2372457 C CA 2372457C
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Prior art keywords
terpolymer
alkyl
dmapma
terpolymer according
terpolymers
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Expired - Lifetime
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CA2372457A
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French (fr)
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CA2372457A1 (en
Inventor
Janusz Jachowicz
Kou-Chang Liu
Roger L. Mc Mullen, Jr.
Thomas Winkler
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ISP Investments LLC
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ISP Investments LLC
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/10—N-Vinyl-pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
    • C08F220/606—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen and containing other heteroatoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Abstract

What is described herein are conditioning/styling terpolymers of vinylpyrrolidone (VP), dimethylaminopropyl methacrylamide (DMAPMA) and C9-C24 alkyl dimethylamino-propyl methacrylic acid quaternized monomers (QDMAPMA), in a defined compositional range. Hair and skin care compositions which include these terpolymers exhibit advantageous low tackiness and high humidity resistance.

Description

CONDITIONING/STYLING TERPOLYMERS
BACKGROUND OF THE INVENTION
1. Field of the Invention This invention relates to polymers for use in hair and skin care compositions, and, more particularly, to conditioning and styling terpolymers having advantageous low tackiness and high humidity resistance.
2. Description of the Prior Art Copolymers of VP and DMAPMA have been used extensively as active components of hair and skin compositions. While these copolymers are generally suitable polymers for such products as conditioners and shampoos, it is desired to provide new polymers having improved performance characteristics in these and other personal care products.
SUMMARY OF THE INVENTION
What is described herein is a terpolymer of vinylpyrrolidone (VP), dimethylaminopropyl methacrylamide (DMAPMA) and C9-C24 alkyl dimethylaminopropyl methacrylic acid quaternized monomers (QDMAPMA), within a defined compositional range, for use in hair and skin care compositions, which are characterized by low tackiness and high humidity resistance.

DETAILED DESCRIPTION OF THE INVENTION
The terpolymers of the invention comprises the following X, Y, and Z monomers, having the formulas given below:
O H
N
\R
(CH2) n H
where:
X is a vinyl cyclic amide, e.g. vinyl pyrrolidone;
n = 3 to 6; R is H or C1-C5 alkyl and wt~ of X = 40-95;
preferably 60-90;

H~ i ~ R4 where:
Y is a derivative of acrylic acid; P is O or NR2; R1, R2 , R3 , R4 are independently H or C1-CS alkyl ; R5 is CZ-Cls alkyl alkylene; and wt~ of Y = 0.1 to 55; preferably 5-30;
O Rs H~ -p-R5-N\ Rs M C Z ) HT~1R1 ' Ra where:
Z is a quaternized derivative of an acrylic acid; P
is O or NR2 ; R1, R2 , R3 , R4 are independently H or C1-C5 alkyl ; R5 is a C2-C16 alkylene ; and R6 is C9-C24 alkyl ; M is a halide, tosylate or phosphate anion; and wt~ of Z = 0.25 to 50, preferably 1-30.
The terpolymers of the invention are hydrophobically-modified cationic polymers having long alkyl-chains therein. A typical terpolymer thus has the following formulas:
-~CH2- i H-j--E-CH2- iH~---~CHZ-i H-3--N ~ =O C=O
~O
H NH
N\ xe N~
Ter (VP-DMAPMA-QDMAPMA) Ci2-ie Suitably, monomer Z is prepared by tosylating DMAPMA
as follows CH2=CH
C=O
DMAPMA + Dodecyltosylate --~ H
Tse N~
In preferred embodiments of the invention, X is vinyl pyrrolidone;
Y is dimethylaminopropyl methacrylamide, and Z is a C1z-C18 alkyl quaternized derivative of an acrylic acid;
X is about 60-90 wt~, Y is about 5-30 wt~ and Z is about 1-30 wt~; Z is C12 alkyl quaternized monomer; the weight average molecular weight of the terpolymer is 200,000 to 2,000,000; preferably 400,000 to 800,000; it is water soluble or water dispersible; and forms a clear humidity resistant, hydrophobic film When cast upon a support surface; Which is surface active and hydrolytically stable; and is a homogeneous terpolymer.
Cosmetic compositions of advantageous properties including about 0.1 to 10~ by weight of the terpolymer can be prepared conveniently in this invention.
Preferably, the homogeneous terpolymers of the invention are made according to the method described by Kou-Chang Liu et al. in U.S. Patent 5,626,836.
swnur~rs~
The preparation of (dodecyldimethyl methacryloimidopropyl ammonium tosylate). [DMAPMA-Cl6Ts]
A mixture of 360 g of dodecyl tosylate and 200 g of DMAPMA were slowly heated up to 70°C without a solvent.
Stirring was continued at 70°C for 2 hours. Then the reaction was cooled to room temperature and solidified product was further used in polymerization without purification .

Terpolymer of VP/DMAPMA/DMAPMAA-CRTs Quat N-Vinylpyrrolidone (VP) (280 g) and deionized water (1400 g) are charged into a 2-liter resin pot equipped with a gas inlet, liquid inlet, a thermometer, and a condenser. The pH of the solution is adjusted to about 7.5 with KOH. Then a stream of nitrogen is introduced which bubbles through the solution during the reaction.
The solution is gradually heated to 65°C for Lupersol~ 11 catalyzed reaction, or to 78°C for a Vazo~ 67 initiated process. Then, DMAPMA (17.5 g) and DMAPMAA-Cl2Ts goat (52.5 g) are added continuously and uniformly into the pot with vigorous stirring for 4 hours so that the relative concentrations of the monomeric VP, DMAPMA, and DMAPMAA-CRTs goat monomer remain practically constant throughout the reaction at predetermined levels.
As soon as DMAPMA and the DMAPMAA-CRTs goat are introduced into the pot, Lupersol~ 11 (t-butylperoxy pivalate in mineral spirits) or Vazo~ 67 2,2-azobis(2-methylbutanenitrile), catalyst is added. The rate of the addition of the catalyst is such that 2 ml of Lupersol is completely delivered in 4 hours. Then the solution is held for an additional 3 hours at 68°C (or 78°C for Vazo 67 initiator). The product is an aqueous solution of a homogeneous terpolymer of VP, DMAPMA and a DMAPMAA-CizTs goat has a predetermined composition indicative of the relative amounts of each monomer used in the process and is substantially free of any residual homopolymer or copolymer. The yield of the terpolymer product is substantially quantitative.

Terpolymers of VP/DMAPMA/QDMAPMAA-DTs (Dodecyl Tosylate Hydrophobe) Ex. Composition (wt~) Conc M" D ~ Resid Resid Resid VP/DMAPMA/ ~ x103 x103 VP DMAPMA HDMAPMA
QDMAPMAA-DTs w/w [cps] [ppm] [ppm] ~C120H
1 74/19.3/6.7 10 540 4.7 117 210 <100 0.34 2 74/19.3/6.7 15 560 4.6 163 640 <100 0.58 3 74/19.3/6.7 10 550 4.6 34.6 640 <100 0.58 4* 80/71/12.9 20 - - 41.4 - - -5* 80/10.36/9.64 20 - - 35 - - -6* 77/20/3 20 - - 26.8 - - -* Vazo 67 initiator used Preparation of cocoyldimethyl methacrylamidopropyl ammonium tosylate A mixture of 284.4 g of C16-Cie tosylate and 126.7 g of DMAPMA were slowly heated up to 70°C without a solvent. Stirring was continued at 70°C for 3 hours.
Then the temperature was raised to 80°C and maintained for 6 hours while stirring. Then the reaction was cooled to room temperature and solidified product was further used in polymerization without purification.
Terpolymer of VP/DMAPMA/DMAPMAA
C16-Cl8Ts Quat .
The copolymerization of VP/DMAPMA/DMAPMAA-Cl6Ts Quat followed the same procedure as given in Example 2.

Polymers of VP/DMAPMA/DMAPMAA-Cl6Ts (Hexadecyl Tosylate Hydrophobe) Ex. Composition (vrt$)Conc.

VP/DMAPMA/

DMAPMAA-Cl6Ts ~ w/~a 8 74/19.3/6.7 15 Preparation of Lauryl-Dimethyl Methacrylamidopropyl Ammonium Chloride A mixture of 350 g of DMAPMA and 280 g of chlorododecene (1.5:1) was stirred with 111.2 g of water (15~k) and 6 drops of concentrated sulfuric acid. The reaction mixture was heated up to 95°C and N2 was bubbled through it. The conversion Was followed by GC. After 24 hours the reaction mixture was cooled off (95g conversion of vinyl chloride) and product was further used in polymerization without purification.

EXAMPhES 12-17 Terpolymer of VP/DMAPMA/QDMAPMA Lauryl Chloride The terpolymerization of VP/DMAPMA/DMAPMAA-C16 C1 goat followed the same procedure as described in Example 2.
Ex.Composition Conc I~" D r~ Resid Resid (wt'k) VP/DMAPMA/ $ 103 X103 VP I~CLA

QDMAPMAA-LCI. w/w (cps) IPPmI IPPm) 12 77/70/3 20 615 5.5 28 600 400 13 74/70/6 20 510 5.4 35 600 800 14 71/70/9 20 485 6.2 64 500 1300 15 93.3/3.7/3 20 493 5.3 13 200 400 16 86.5/7.5/6 20 550 6.8 14 400 800 17 79.8/11.2/9 20 575 7.2 30 300 1300 EXAMPhE 18 CONDITIONING CREAM RINSE FORMUhATION
Part A
86.4 Deionized H20 0.5~ ShES (Cerasynt LP; ISP) 0.1~ NaEDTA (Ethylenediaminetetraacetic acid disodium salt dehydrate; Aldrich) Part B
2.55 Cetyl Stearyl Alcohol (hanette Wax O; Henkel Corporation) Part C
lOg Aculyn 46 (modified polyethylene glycol, enzymatically modified starch; Rohm & Haas) Part D
0.5~ Conditioning Additive of Example 13 Instructions Heat Part A to 60°C with moderately slow stirring. Add Part B to Part A once Part A appears well mixed and homogeneous. Continue slow stirring and allow solution to cool to an ambient temperature. Add Part C while stirring and eventually add Part D.

CONDITIONING SHAMPOO FORMULATION
Part A
15~ Ammonium Lauryl Sulfate (Standapol A, Henkel Corporation) 15~ Sodium Lauryl Sulfate (Rhodapon SB-8208/S, Rhone Poulenc) 8~ Cocamidopropyl Betaine (Mitratine CB, Rhone Poulenc) 2~ Lauramide DEA (Monamid 716, Mona Industries) Part B
1$ Conditioning Additive of Example 13 58.88 Deionized H20 Part C
0.2g Diazolidinyl Urea/Iodopropynyl Butylcarbamate (Germall Plus, ISP) Instructions Heat Part A to 60°C with moderately slow stirring for approximately 1-~ hr. or until solution becomes transparent. At the same time, heat Part B to 55°C while stirring until homogeneous solution is obtained. Add Part B to Part A while continuously stirring. Remove temperature source. Once the resulting solution has reached 45°C, add Part C. Continue to stir (slowly) until the target solution has cooled to an ambient temperature.
In the conditioners and shampoo formulations tested under actual use conditions in comparison with similar formulations with known polymers, the terpolymers of the invention have excellent wet combing, excellent dry feel and softness, and excellent wet feel.
Furthermore they are characterized by excellent styling properties in terms of stiffness, humidity resistance and dry and wet feel.

STYLING LOTION
A styling lotion formulation was prepared in aqueous solution using 1$ by weight of the terpolymer of Example 1 and 0.1~ preservative.

EXAMPhE 21 STYhING MOUSSE
A concentrate is prepared by dissolving 1 g of the terpolymer of Example 1, 0.1 g of preservative and 98.9 g of deionized water.
A styling mousse formation a.s prepared by mixing 70 g of the concentrate and 30 of hydrocarbon propellant in an aerosol can provided with a mousse dispenser.
While the invention has been described with particular reference to certain embodiments thereof, it will be understood that changes and modifications may be made which are within the skill of the art. Accordingly, it is intended to be bound only by the following claims, in which:

Claims (12)

WHAT IS CLAIMED IS:
1. A terpolymer comprised of the following monomers;

X, Y and Z;

where:
n is 3 to 6; R is H or C1-C5 alkyl and wt% of X = 40-95;

where:
P is O or NR2 ; R1, R2, R3, R4 are independently H or C1-C5 alkyl; R5 is C2-C16 alkyl alkylene; and wt% of Y = 0.1 to 55; and where:

P is O or NR2 ; R1, R2, R3, R4 are independently H or C1-C5 alkyl; R5 is a C2-C16 alkylene; R6 is C9-C24 alkyl;

M is a halide, tosylate or phosphate anion; and wt% of Z = 0.25 to 50.
2. A terpolymer according to claim 1 wherein:

X is vinyl pyrrolidone, Y is dimethylaminopropyl methacrylamide, and Z is a C12-C18 alkyl quaternized derivative of an acrylic acid.
3. A terpolymer according to claim 2 wherein X is about 60-90 wt%, Y is about 5-30 wt% and Z is about 1-30 wt%.
4. A terpolymer according to claim 2 wherein Z is C12 alkyl quaternized monomer.
5. A terpolymer according to claim 1 Wherein the weight average molecular weight is 200,000 to 2,000,000.
6. A terpolymer according to claim 5 wherein said molecular Weight is 400,000 to 800,000.
7. A terpolymer according to claim 2 which is water soluble or water dispersible.
8. A terpolymer according to claim 1 which forms a clear humidity resistant, hydrophobic film when cast upon a support surface.
9. A terpolymer according to claim 1 which is surface active and hydrolytically stable.
10. A terpolymer according to claim 1 which is a homogeneous terpolymer.
11. A cosmetic composition including about 0.1 to 10% by weight of the terpolymer of claim 1.
12. A cosmetic composition according to claim 11 which is a hair or skin care product.
CA2372457A 1999-05-07 2000-04-05 Conditioning/styling terpolymers Expired - Lifetime CA2372457C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/307,211 1999-05-07
US09/307,211 US6207778B1 (en) 1999-05-07 1999-05-07 Conditioning/styling terpolymers
PCT/US2000/009065 WO2000068282A1 (en) 1999-05-07 2000-04-05 Conditioning/styling terpolymers

Publications (2)

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CA2372457A1 CA2372457A1 (en) 2000-11-16
CA2372457C true CA2372457C (en) 2010-06-22

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US (1) US6207778B1 (en)
EP (1) EP1194460A4 (en)
JP (1) JP4999230B2 (en)
KR (1) KR100681630B1 (en)
CN (1) CN1147510C (en)
AU (1) AU767677B2 (en)
BR (1) BR0010360B1 (en)
CA (1) CA2372457C (en)
WO (1) WO2000068282A1 (en)

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