MXPA01011277A - Conditioning/styling terpolymers - Google Patents

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

TERPOLIMERS FOR CONDITIONING / STYLING BACKGROUND OF THE INVENTION 1, Field of the Invention This invention relates to polymers for use in hair care and skin care compositions, and, more particularly, to terpolymers for conditioning and styling, which have advantageous low viscosity strength and high humidity. 2. Description of the Prior Art VP and DMAPMA copolymers 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 novel polymers having improved performance characteristics in these and other personal care products.

BRIEF DESCRIPTION OF THE INVENTION What is described herein is a terpolymer of vinylpyrrolidone (VP), dimethylaminopropylmethacrylamide (DMAP.MA) and quaternized monomers of C9-C24 alkyldimethyl-aminopropylmethacrylic acid (QDMAPMA), within a defined conventional range, for use in compositions REF 133844 for the care of the hair and skin, which are characterized by resistance of low tackiness and high humidity.

DETAILED DESCRIPTION OF THE INVENTION The terpolymers of the invention comprise the following monomers X, Y and Z, having the formulas given below: wherein: X is a cyclic vinyl amide, for example vinylpyrrolidone; n = 3 to 6; R is H or C 1 -C 5 alkyl and the weight% of X = 40-95 / preferably 60-90; where: Y is a derivative of acrylic acid; P is = 0 or NR2; Ri, R2, R3, R4 are independently H or C1-C5 alkyl; R 5 is C 1 -C 6 alkylalkylene; and the% by weight of Y = 0.1 to 55; preferably 5-30; where: Z is a quaternized derivative of an acrylic acid; P is O or NR2; R1 f R2, R3, R are independently H or C? -C5 alkyl; R5 is an alkylene of C2-C6; and Re is Cg-C2 alkyl; M is a halide, tosylate or phosphate anion; and the% by weight of Z = 0.25 to 50, preferably 1-30. The terpolymers of the invention are hydrophobically modified cationic polymers, which have long alkyl chains in the present. In this way a typical terpolymer has the following formulas: Ter Suitably, the monomer Z is prepared by tosylation of DMAPMA as follows: CH2 = CH DMAPMA + Dodßsiltosilato In the preferred embodiments of the invention, X is vinylpyrrolidone; Y is dimethylaminopropylmethacrylamide, and Z is a quaternized derivative of C? 2-C? Alkyl of an acrylic acid; X is about 60-90% by weight, Y is about 5-30% by weight and Z is about 1-30% by weight; Z is a quaternized C? 2 alkyl monomer; the weight average molecular weight of the terpolymer is 200,000 to 2,000,000; preferably from 400,000 to 800,000; is soluble in water or dispersible in water; and forms a clear hydrophobic film, resistant to moisture when it occurs on a support surface; which is surfactant and hydrolytically stable; and it is a homogeneous terpolymer.

Cosmetic compositions of advantageous properties which include from about 0.1 to 10% by weight of the terpolymer in this invention can be conveniently prepared. 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.

EXAMPLE 1 The preparation of (dodecyldimethyl-methacryloimidopropylammonium tosylate). [DMAPMA-C? 6Ts] A mixture of 360 g of dodecyl tosylate and 200 g of DMAPMA was heated slowly to 70 ° C without a solvent. Stirring was continued at 70 ° C for 2 hours. The reaction was then cooled to room temperature and the solidified product was further used in polymerization without purification.

EXAMPLE 2 Terpolymer of VP / DMAPMA / DMAPMAA-C12Ts Cuat. N-vinylpyrrolidone (VP) (280 g) and deionized water (1400 g) were charged in a 2 liter resin vessel equipped with a gas inlet, a liquid inlet, a thermometer and a condenser. The pH of the solution was adjusted to approximately 7.5 with KOH. Then a stream of nitrogen bubbling through the solution was introduced during the reaction. The solution was gradually heated to 65 ° C by the catalyzed reaction of Lupersol® 11, or at 78 ° C by an initiated Vazo® 67 process. Then, DMAPMA (17.5 g) and DMAPM were added continuously and uniformly. C? 2Ts cuat (52.5 g) in a vessel with vigorous stirring for 4 hours so that the relative concentrations of the monomeric VP monomer, DMAPMA and DMAPMAA-C? 2Ts cuat remain constant for virtually the entire reaction at predetermined levels. As soon as DMAPMA and DMAPMAA-C? 2Ts cuat are introduced into the vessel, Lupersol® catalyst (t-butylperoxypivalate in mineral spirits) or Vazo® 67 2, 2-azobis (2-methylbutanonitrile) is added. The speed of the catalyst addition is such that 2 ml of Lupersol is completely distributed in 4 hours. Then the solution is maintained for an additional 3 hours at 68 ° C (or 78 ° C by Vazo 67 primer). The product is an aqueous solution of a homogeneous terpolymer of VP, DMAPMA and a DMAPMAA-C? 2Ts cuat 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.

EXAMPLES 1-6 VP / DMAPMA / QDMAPMAA-DTs Terpolymers (Dodecyl Tosylate Hydrophobic) Example Composition (% by weight) Conc. M »0 n Residue Residue Residue VP / DMXPI? /% XíO3 xl0J VP DMA PMA HDtAPM? QD.MWMXA-DT * p / p lepa] [ppm] tpppi] * C "OH 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 - - - * Initiator Vazo 67 used EXAMPLE 7 Preparation of cocoyl dimethyl methacrylamidopropylammonium tosylate A mixture of 284.4 g of C 6 -CI 8 tosylate and 126.7 g of DMAPMA was slowly heated to 70 ° C without a solvent. Stirring was continued at 70 ° C for 3 hours. The temperature was then raised to 80 ° C and maintained while stirring for 6 hours. The reaction was then cooled to room temperature and the solidified product was further used in polymerization without purification.

EXAMPLE 8 Terpolymer of VP / DMAPMA / DMAPMAA C? 6-C? 8Ts Cuat. The copolymerization of VP / DMAPMA / DMAPMAA-C? 6Ts Cuat followed the same procedure given in Example 2.

EXAMPLES 8-10 Polymers of VP / DMAPMA / DMAPMAA-CX6Ts (Hydrophobic Hexadecyl Tosylate) Eí. Composition (% by weight) Conc. W / MS? PMA / DMAÍMAA-CnTs% p / p 8 74 / 19.3 / 6.7 15 9 74/20/6 20 10 77/20/3 20 EXAMPLE 11 Preparation of Lauryldimethylmethacrylamidopropylammonium 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%) and 6 drops of concentrated sulfuric acid. The reaction mixture was heated to 95 ° C and N2 was bubbled completely. The conversion was followed by CG. After 24 hours, the reaction mixture was extracted by cooling (95% conversion of vinyl chloride) and the product was further used in polymerization without purification.

EXAMPLE 12-17 Lauryl Chloride Terpolymer of VP / DMAPMA / QDMAPMA Terpolymerization of Cl of VP / DMAPMA / DMAPMAA-CX6 cuat followed the same procedure described in Example 2.

Ej- Composition (% by weight) Conc. H. O n Residue Residue VP / DMA.BM? /% 10J xlO5 VP CU QDMAPMX? - CI, p / p [cps] [ppm] [ppm] 12 77/70/3 20 615 5. S 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 EXAMPLE 18 CONDITIONING CREAM RINSE FORMULATION Part A 86.4% Deionized H20 0.5% SLES (Cerasynt LP; ISP) 0.1% NaEDTA (disodium salt dihydrate, ethylene diaminotetraacetic acid, Aldrich) Part B 2.55 Cetilestearyl Alcohol (Lanette ax 0, Henkel Corporation) Part C 10% 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 Party B to Party A once Party A appears well mixed and homogeneous. Stirring continues slowly and the solution is allowed to cool to room temperature. Part C is added while adding Part D in agitation and eventually.

EXAMPLE 19 FORMULATION OF SHAMPOO IN CONDITIONING Part A 15% Ammonium Lauryl Sulfate (Standapol A, Henkel Corporation) 15% Sodium Lauryl Sulfate (Rhodapon SB-8208 / S, Rhône Poulenc) 8% Cocamidopropyl Betaine (Mitratine CB, Rhône Poulenc) 2% Lauramida DEA (Monamid 716, Mona Industries) Part B 1% Conditioning Additive of Example 13 58.8% Deionized H20 Part C 0.2% Diazolidinylurea / Yodopropynyl Butylcarbamate (Germall Plus, ISP) Instructions Heat Part A to 60 ° C with moderately slow stirring for about an hour or until the solution becomes clear. At the same time, heat Part B to 55 ° C while stirring until homogenous solution is obtained. Add Part B to Part A while the agitation is continuously. Separate the temperature source. Once the resulting solution has reached 45 ° C, Part C is added. Stirring continues (slowly) until the target solution has cooled to room temperature. In the conditioner and shampoo formulations tested under conditions of current use as compared to similar formulations with known polymers, the terpolymers of the invention have excellent wet combing, excellent dry feeling and softness and excellent wet feel.

In addition, they are characterized by excellent styling properties in terms of resistance to stiffness, moisture and dry and wet sensation.

EXAMPLE 20 LOTION FOR STYLIZATION A lotion formulation for aqueous solution was prepared using 1% by weight of the terpolymer of Example 1 and 0.1% of preservative.

EXAMPLE 21 MOUSSE (FOAM) FOR STYLIZATION A concentrate was prepared by dissolving 1 g of the terpolymer of Example 1, 0.1 g of preservative and 98.9 g of deionized water. An ousse formation for styling was prepared by mixing 70 g of the concentrate and 30 g of hydrocarbon propellant in an aerosol can supplied with an automatic mousse dispenser. While the invention has been described with particular reference to certain embodiments thereof, it will be understood that changes and modifications can be made that are within the skill of the art. Accordingly, it is understood that it is only bound by the following claims wherein: It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects or products to which it refers.

Claims (12)

CLAIMS Having described the invention as above, the content of the following claims is claimed as property:

1. A terpolymer characterized in that it is composed of the following monomers; X, Y and Z; where: n is from 3 to 6; R is H or C 1 -C 5 alkyl and the weight% of X = 40-95; where: P is 0 or NR2; R1 t R2, R, R4 are independently H or C? -C5 alkyl; R5 is C2-C6alkylalkylene; and the% by weight of Y = 0.1 to 55; Y where: P is 0 or NR2; Ri, R2, R3, R4 are independently H or C1-C5 alkyl; R5 is an alkylene of C2-C6; R6 is Cg-C2 alkyl; M is a halide, tosylate or phosphate anion; and the% by weight of Z = 0.25 to 50.

2. A terpolymer according to claim 1, characterized in that: X is vinylpyrrolidone; Y is dimethylaminopropyl methacrylamide, and Z is a quaternized C 1 -C 2 alkyl derivative of an acrylic acid.

3. A terpolymer according to claim 2, characterized in that X is about 60-90% by weight, Y is about 5-30% by weight and Z is about 1-30% by weight.

4. A terpolymer according to claim 2, characterized in that Z is a quaternized C? 2 alkyl monomer.

5. A terpolymer according to claim 1, characterized in that the weight average molecular weight is from 200,000 to 2,000,000,000.

6. A terpolymer according to claim 5, characterized in that the molecular weight is from 400,000 to 800,000.

7. A terpolymer according to claim 2, characterized in that it is soluble in water or dispersible in water.

8. A terpolymer according to claim 1, characterized in that it forms a clear hydrophobic film, resistant to moisture when it occurs on a support surface.

9. A terpolymer according to claim 1, characterized in that it is surfactant and hydrolytically stable.

10. A terpolymer according to claim 1, characterized in that it is a homogeneous terpolymer.

11. A cosmetic composition, characterized in that it includes from about 0.1 to 10% by weight of the terpolymer according to claim 1.

12. A cosmetic composition according to claim 11, characterized in that it is a product for the care of hair or skin.