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Publication numberUS3836537 A
Publication typeGrant
Publication dateSep 17, 1974
Filing dateOct 25, 1972
Priority dateOct 7, 1970
Publication numberUS 3836537 A, US 3836537A, US-A-3836537, US3836537 A, US3836537A
InventorsF Boerwinkle, D Waxberg
Original AssigneeMinnesota Mining & Mfg
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Zwitterionic polymer hairsetting compositions and method of using same
US 3836537 A
Abstract  available in
Images(4)
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Claims  available in
Description  (OCR text may contain errors)

United States Patent "Office 3,836,537 Patented Sept. 17, 1974 3,836,537 ZWITTERIONIC POLYMER HAIRSE'I'IING COM- POSITIONS AND METHOD OF USING SAME Fred P. Boerwinkle, Village of Lakeland, and Donald L. Waxberg, Village of Roseville, Minn. (both 3M Center, St. Paul, Minn. 55101) No Drawing. Continuation-impart of abandoned application Ser. No. 78,968, Oct. 7, 1970. This application Oct. 25, 1972, Ser. No. 300,832

Int. Cl. C08f 29/46, 37/00, 37/18 U.S. 'Cl. 26029.6 HN 22 Claims ABSTRACT OF THE DISCLOSURE Hairsetting is achieved with a solution containing a zwitterionic polymer having carboxylate and ammonium functionality.

CROSS-REFERENCE TO RELATED APPLICATION This is a continuation-in-part of application Ser. No. 78,968, filed Oct. 7, 1970 and now abandoned.

BACKGROUND OF THE INVENTION Almost since the beginning of time women have employed compositions of some sort to make straight hair curly and to hold it in position after doing so. Perhaps the earliest material employed was plain water which was used to soften hair, but hair which has been moistened, curled, and dried in curled condition retains its shape for only a short time. More recently, hair has been styled or arranged with solutions containing lacquers such as natural gums, resins, or synthetic plastics (e.g., polyvinyl pyrrolidone) which are deposited on the fibers of the hair to hold them in place.

Such prior art lacquers are known for their characteristics of making hair dulll, stiff, unnatural, sticky, and hard to clean. Many of them tend to flake unattractively. Some cause the hair to accumulate static electricity, making it difficult to comb or brush. Others, e.g., polyvinyl pyrrolidone, absorb moisture from the air and become sticky on damp days and hard and brittle in extremely dry weather. Still others are adversely affected by water vapor, permitting treated hair to lose its curl in moist weather.

SUMMARY The present invention provides a hairsetting composition which overcomes the objections inherent in the products of the prior art. In the practice of the invention, hair is imparted with a temporary setting which has excellent anti-static behavior and curl retention, gOOd comb-out and sheen, and which is easily removed by shampooing. Additionally, the excellent curl-retention is maintained at high relative humidity. The treated hair is flexible, readily arranged, pleasant smelling, clean, attractive, and glossy, retaining these characteristics for several days, regardless of the relative humidity of the air.

It has been found that zwitterionic polymers, when applied to hair fibers, provide the above-described desirable properties, maintaining very high curl-retention at high relative humidities.

In the context of the invention, the expressions zwitterionic polymer and zwitterionic monomer refer only to internally neutralized polymers and monomers con taining an acidic carboxylate group and a basic ammonium group.

DETAILED DESCRIPTION OF THE INVENTION In accordance with the invention, hair is treated with an aqueous solution containing from about 0.25 to about 10% by weight of zwitterionic polymer. Any one of a variety of such polymers will be useful in the practice of the invention but two particular types which have been found to be especially useful will be described below.

The aqueous solution of a zwitterionic polymer, to be useful for treating hair, should be sufficiently viscous to remain on hair fibers when applied thereto, and sufficiently thin to effectively wet the hair fibers. It has been found that useful zwitterionic polymers have a viscosity of about to 100,000 cps., preferably about 1,000 to about 25,000 cps., when tested at 24% solids in water with a Brookfield viscometer, using the appropriate spindle and speed therefor.

Aqueous solutions of the zwitterionic polymer that have been found to be most effective for setting hair have from about 0.25 to about 10% by weight, preferably about 1 to about 5%, of the zwitterionic polymer. Polymers having viscosities higher than those mentioned above when measured as 24% solids aqueous solutions or hairsetting solutions having excess of 10% by Weight of zwitterionic polymer provide a stiffer curl which is more difficult to comb-out and cause the hair fibers to feel undesirably slippery during application.

The hairsetting solutions of the invention may contain an alcohol as a co-solvent with water, particularly when the zwitterionic polymer is a copolymer containing a water-insoluble monomer, as will be hereinafter described. The solutions may also contain other additives that are normally found in conventional hairsetting solutions such as perfumes, coloring dyes and the like.

It has been also discovered that the addition of a small amount of zwitterionic polymer to prior art hairsetting solutions provides improved curl-retention and anti-static behavior. The addition of as little as 0.25% by weight of zwitterionic polymer to such prior art hairsetting compositions has been found to be effective for such purposes.

PRESENTLY PREFERRED ZW'ITTERIONIC POLYMERS (A) Homopolymers and copolymers may be prepared by polymerizing zwitterionic monomers having the general formula wherein R represents a polymerizable unsaturated group, which permits homopolymerization of the monomer or copolymerization with other polymerizable monomers. Such polymerizable unsaturated groups are preferably selected from the group consisting of acrylate, methacrylate, acrylamide, and methacrylamide. Subscripts x and y represent an integer from 1 to 3 inclusive to provide methylene, ethylene, or propylene groups in the polymer backbone, groups larger than 3 carbon atoms reducing the water solubility of the resultant polymer such that it may not be useful as a hair-setting composition. R and R represent hydrogen, methyl, ethyl or propyl radicals, larger alkyl radicals reducing the water solubility of the polymer. R and R represent a hydrogen atom or an alkyl radical, with the total sum of the carbon atoms in R and R not exceeding six, larger alkyl radicals also reducing the water solubility of the polymer.

Typical zwitterionic monomers having the general formula shown above and useful in preparing homopolymers or copolymers useful in the hairsetting compositions of the invention, include, beta-methacryloxyethyl beta-dimethyl amino propionate betaine. Zwitterionic monomers of this type may be prepared by methods known to the art, e.g., U.S. Pats. 2,744,130, and 2,777,872.

The aforementioned zwitterionic monomers may either be homopolymerized or copolymerized with other polymerizable monomers to provide the zwitterionic polymers useful for setting hair, the resultant polymer retaining the above-described desirable properties even when relatively large proportions of non-zwitterionic comonomer are used. Generally, the zwitterionic moiety of the desired copolymer should comprise at least, on a molar basis, about 10%, preferably at least about 20%, of the copolymer to retain the above-described properties. Typical water-soluble non-zwitterionic monomers suitable for copolymerization include vinyl pyrrolidone, dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl acrylate, and diethylaminoethyl methacrylate.

Other non-zwitterionic monomers which are not watersoluble, such as alkyl acrylates or methacrylates, e.g., methyl acrylate, and acrylamides, methacrylamides, or vinyl acetate, may also be copolymerized with the previously mentioned zwitterionic monomers to provide copolymers useful for setting hair. However, substantially less of this type of non-zwitterionic monomer is utilized so as to maintain the requisite solubility.

(B) Zwitterionic polymers containing carboxylate and ammonium functionality are also prepared by copolymerizing a monomer having basic ammonium functionality with monomer having acid carboxylate functionality. The acidic monomers are preferably substituted vinyl compounds of the general formula CR H=CR OO H, wherein R is a hydrogen atom or a CO H group and R is a hydrogen or chlorine atom or a methyl group; exemplary compounds of this type include acrylic acid, methacrylic acid, maleic acid and a-chloroacrylic acid. The basic monomers are preferably substituted vinyl compounds of the formula CH =CR COQ wherein R is a hydrogen atom or a methyl group and Q is an organic radical containing a basic nitrogen-containing group, such compounds including dialkyl aminoalkyl methacrylates (e.g., dimethylaminoethyl methacrylate), dialkyl aminoalkyl acrylates, N(1,1-dirnethyl-3-dimethyl-amino propyl) acrylamide methacrylamino pyridine, and the The zwitterionic copolymer produced from acidic and basic monomers preferably will be formed of monomers of acrylic acid or methacrylic acid polymerized with monomers of dimethylaminoethyl methacrylate or diethylaminoethyl acrylate.

For most purposes the mole ratio of basic monomer to the acidic monomer of the aforementioned zwitterionic copolymer ranges from 0.821 to 2.5 :1, preferably 1:1 to 15:1. In the case of difunctional monomers, suitable adjustment should be made in mole ratios to maintain a similar acid-base balance. For monomers with difunc tional acidity, the ratio of basic monomer to acidic monomer will be 1.7 :1 to :1, preferably 2:1 to 3:1. The resultant copolymer is preferably substantially completely neutralized, although partially neutralized copolymers are also useful for setting hair.

The neutralizing agents are acidic and basic compounds which will not, once having served their function, produce substances which will deleteriously affect hair or the copolymers ability to set hair. Acidic neutralizing agents include hydrochloric acid, acetic acid and the like. Basic neutralizing agents include ammonia, amines and the like.

Zwitterionic copolymers, besides being formed of acidic and basic monomers, may include additional monomers which do not contain acidic or basic groups, which may be added to reduce cost. Such monomers typically include lower alkyl acrylates or methacrylates, e.g., methyl acrylate, and acrylamides or methacrylamides. These neutral monomers, which can be water-soluble or water-insoluble, will be contained in the copolymer in proportions which do not adversely affect the solubility of the resultant copolymer. Typically, water-insoluble monomers will be a minor proportion of the resultant copolymer.

The effectiveness of zwitterionic polymers for use in hairsetting compositions is readily determined by means 4 of a curl retention test which also provides information with respect to anti-static behavior, comb-out, and sheen. In conducting the test, a predetermined weight of human hair (approximately 6 inch length) is shampooed, rinsed with water, saturated with the respective hairsetting composition being tested, and combed four times. Each hair swatch is then wound on a hair roller, secured with bobby pins and dried at 140 F. for approximately two and onehalf hours. Immediately following drying, the hair swatches are unwound from the rollers, brushed five times, and are then ready for determination of curl retention.

Ten hair swatches are prepared for each hairsetting composition to be tested. The initial hair length is recorded and the test swatches placed in a high relative humidity test environment (about relative humidity at about 75 F. for one hour). The change in curl length is observed immediately after the period of time in the humidity chamber, the percent of curl retention being calculated by the formula t L X where L is the length of the hair fully extended, L is the length of the hair when curled before exposure to the humidity environment, and L is the length of the hair after exposure to the high humidity environment. Because factors such as humidity in the drying oven, etc. cause results to be somewhat different for tests conducted on different days, all compositions are compared relative to a control sample evaluated at the same time. The percent curl retention for each hairsetting composition is then divided by the percent curl retention of the control and multiplied by 100 to obtain the relative curl retention. The composition of Example 1 was used as a control in each instance.

The following examples, in which all parts are by weight unless otherwise indicated, illustrate preparation of the hairsetting compositions of the invention, without limiting the scope thereof.

Example 1 As a control, polydimethylaminoethyl methacrylate fully quaternized with methyl bromide was prepared and evaluated as a hairsetting lotion at 3% solids by weight in water, as disclosed in British Pat. 1,161,642. When tested by the previously described method, a relative curl retention of 100 was obtained.

Example 2 This example illustrates preparation of a hairsetting composition utilizing a zwitterionic polymer comprising an 80:20 mole ratio copolymer of dimethylaminoethyl methacryloxyethyl, beta-dimethyl aminopropionate betaine.

A polymerization flask fitted with a stirrer, nitrogen inlet, thermocouple, and addition funnel, was charged with 2842 gms. of water, 315.2 gms. of a 37% hydrochloric acid water solution, 618 gms. of dimethylaminoethyl methacrylate, and 225.2 gms. of beta-dimethyl, beta-methacryloxyethylamino propionate. betaine. The solution, with stirring, was evacuated to boiling for about 30 minutes, the flask purged with nitrogen, and the solution heated to 600 C. for 16 hours, during which time ml. of water containing 40 gms. of K S O was added in four equal portions about 30 minutes apart. The resultant polymer solution had a Brookfield viscosity of 16,600 cps. at 25 C. (#4 spindle at 30 r.p.rn.).

The polymer, at 3% solids in water, was evaluated as a hairsetting resin by the previously described test method, a relative curl retention of 148, moderate comb-out, good sheen, and low static retention being obtained.

Examples 3-12 The following polymers were prepared in a manner y are integers from 1 to 3 inclusive, and R and R represent a hydrogen atom or an alkyl radical with the total sum of the carbon atoms in R and R not exceeding six, and

EXAMPLES 3l2 Composition Brookfield viscosity (cps.) and conditions Relative Temp NaZSZOa, curl re- Example Monomers Mole ratio percent 24% Spindle R.p.m. 3% Spindle Rpm. tention o u 4 DMAEMA-betaine 1 Homopolymer 60 0.5 9 21,500 4 154 DEAEA IMAA 3 50:50 60 1.0 .000 4 125 X fi Dimethyl fi-methacryloxyethylaminopropionate betaine. 2 Diethylaminoethyl acrylate.

3 Methacrylic acid.

4 Dimethylaminoethyl methacrylate.

5 Diethylaminoethyl methacrylate.

' N(l,1 dimethyl-3-dimethylaminopropyl) acrylamlde.

B 4% solids.

9 20% solids.

Example 14 Into a 5 liter flask was placed 2137 gms. anhydrous ethanol, 160.5 g. acrylic acid mole percent), 350 gms. dimethylaminoethyl methacrylate (35 mole percent), 164.3 gms. methyl acrylate (30 mole percent) and 1.687 gms. azobisisobutyronitrile. The solution was heated to 70 C. for 17 hrs, producing thereafter a white solution which was diluted with water to 3% solids to provide a hairsetting composition which gave a relative curl retention of 136.

Example 15 A polymer was prepared in a manner similar to that described in Example 14 except vinyl acetate was used in place of methyl acrylate. A relative curl retention of 119 was obtained with a 3 solution.

Example 16 A hairsetting composition was prepared containing 2.75 percent by weight polyvinyl pyrrolidone and 0.25% by weight of the polymer of Example 3 in water. Upon testing by the previously described method, the composition was found to have a relative curly retention of 106. As a comparison, a hairsetting lotion containing only 3% by weight polyvinyl pyrrolidone, was tested in the previously described manner and was found to have a relative curl retention of 86.

What is claimed is:

1. A method of setting hair comprising the sequential steps of (1) moistening the hair, (2) applying at ambient temperature an aqueous hairsetting composition comprising from about 0.25 to about 1 0% by weight of a zwitterionic polymer in water, said polymer containing at least 10% on a molar basis of zwitterionic moiety, a 24% solids aqueous solution of said polymer having a Brookfield viscosity of from about 100 to 100,000 cps. (3) and drying the hair, thereby imparting to said hair excellent anti-static behavior, comb-out, sheen, and high curl retention maintainable even at high relative humidity, said polymer being selected from a group consisting of (A) polymers of carboxy betaines having the repeating wherein R represents a polymerizable unsaturated group selected from the group consisting of acrylate, methacrylate, acrylamide and methacrylamide, R and R are hydrogen atoms or lower groups, x and 10% solids.

11 Excess amine neutralized with HCl.

12 Excess amine neutralized with acetic acid. 13 Acrylamide.

14 Run at 12% solids.

1E 12% solids.

N-(y-methacryloxy, fl hydr0xypropyl)N-trimethyl ammonium chloride.

(B) copolymers of monomers (1) and (2), shown below:

(1) substituted acidic vinyl compounds having the general formula =CR H=CR CO H wherein R represents a hydrogen atom or a carboxylic acid group and R represents a hydrogen atom, a chlorine atom or a methyl group, and

(2) substituted basic vinyl compounds having the general formula CH =CR COQ wherein R represents a hydrogen atom or a methyl group and Q is an organic radical containing a basic nitrogen-containing group, wherein said acidic and basic functionalities are retained in the copolymer structure and wherein the mole ratio of basic monomer to acidic monomer in said copolymer is from 0.8:1 to 2.5:1, except where R; is CO H, the mole ratio is 1.721 to 5:1.

2. The method of claim 1 wherein the (B)(l) monomers are selected from the group consisting of acrylic acid, maleic acid, u-chloroacrylic acid and methacrylic acid and the (B)(2) monomers are selected from the group consisting of dialkyl amino alkyl methacrylates, dialkylamino alkyl acrylates and methacrylamino pyridine, wherein molar amounts of basic monomer to acidic monomer in the copolymer are in a range of 0.8:1 to 2.5 :1 with excess acid or excess base being substantially neutralized, except where R is CO H, the mole ratio is 1.7:1 to 5:1.

3. The method of claim 2 wherein said range of basic monomer to acidic monomer in said copolymer is from 1:1 to 1.5 :1, except that where R is CO H, the mole ratio is 2:1 to 3:1.

4. The method of claim 1 wherein said zwitterionic polymer also contains non-zwitterionic monomer.

5. The method of claim 4. wherein said non-zwitterionic monomer is selected from a group consisting of vinyl pyrrolidone, dialkylaminoalkyl acrylates, dialkylaminoalkyl methacrylates, quaternary ammonium acrylates, quaternary ammonium methacrylates, alkyl acrylates, alkyl methacrylates, acrylamides, methacrylamides, and vinyl acetate.

6. The method of claim 1 wherein said (B)(2) monomer is selected from the group consisting of N(1,1-dimethyl 3-dimethylaminopropyl) acrylamide, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, and diethylaminoethyl acrylate and wherein said (B) (1) monomer is selected from the group acrylic acid and methacrylic acid.

7. The method of claim 1 wherein said (A) monomer is beta-methacryloxyethyl beta-dimethyl aminopropionate betaine.

8. The method of claim 1 wherein R is selected from the group consisting of acrylate, methacrylate, acrylamide, and methacrylamide.

9. The method of claim 1 wherein x and y are 2.

10. The method of claim 1 wherein said aqueous hairsetting composition also contains an amount effective for setting hair of a water-soluble hairsetting resin previously known for setting hair.

11. The method of claim 10 wherein said previously known resin is polyvinyl pyrrolidone.

12. Method of claim 1 wherein said polymer is a copolymer of dimethylaminoethyl methacrylate and betamethacryloxyethyl beta-dimethyl aminopropionate betaine containing less than 30 mole percent of dimethylaminoethyl methacrylate.

13. Method of claim 1 wherein said polymer is a copolymer of vinyl acetate and beta-methacryloxyethyl betadimethyl aminopropionate betaine containing less than 80 mole percent of vinyl acetate.

14. Method of claim 1 wherein the polymer is a copolymer of beta-dimethyl beta-methacryloxyethyl aminopropionate betaine and less than 30 mole percent of a comonomer selected from the group consisting of quaternary ammonium acrylates and quaternary ammonium methacrylates.

15. The method of claim 1 wherein said hairsetting composition contains from 1-5% by weight zwitterionic polymer.

16. A liquid composition for imparting to hair treated therewith static-free behavior, good comb-out andl sheen, and high curl retention maintainable even at high relative humidity, consisting essentially of an aqueous solution containing from about 0.25 to about 10% by weight of a zwitterionic polymer containing at least 10% on a molar basis of zwitterionic moiety, a 24% solids aqueous solution of said polymer having a Brookfield viscosity of from about 100 to 100,000 cps, said polymer being a copolymer of monomers (1) and (2),

(1) substituted acidic vinyl compounds having the general formula CR H=CR OO H wherein R represents a hydrogen atom or a carboxylic acid group and R represents a hydrogen atom, a chlorine atom or a methyl group, and

(2) substituted basic vinyl compounds having the general formula CH =CR COQ wherein R represents a hydrogen atom or a methyl group and Q is an organic radical containing a basic nitrogen-containing group wherein said acidic and basic functionalities are retained in the copolymer structure, said acidic monomers being selected from the group consisting of acrylic acid, maleic acid, a-chloro-acrylic acid and methacrylic acid and said basic monomers being selected from the group consisting of diallrylamino alkyl methacrylates, dialkylamino alkyl acrylates and methacrylamino pyridine, wherein the mole ratio of said basic monomer to said acidic monomer in said copolymer is from 0.8:1 to 2.5:1, except where R; is CO H when said mole ratio is 1.7:1 to :1.

17. The composition of claim 16 wherein said zwitterionic polymer also contains non-zwitterionic monomer.

18. The composition of claim 17 wherein said nonzwitterionic monomer is selected from a group consisting of vinyl pyrrolidone, dialkylaminoalkyl acrylates, dialkylaminoalkyl methacrylates, quaternary ammonium acrylates, quaternary ammonium methacrylates, alkyl acrylates, alkyl methacrylates, and vinyl acetate.

' 19. The composition of claim 16 wherein said basic monomer is selected from the group consisting of N(l,ldimethyl-3-dimethylaminopropyl) acrylamide, dimethylaminoethyl methacrylate, and diethylaminoethyl acrylate and wherein said acidic monomer is selected from the group acrylic acid and methacrylic acid.

20. The composition of claim 16 wherein said hairsetting composition contains from 1-5% by weight zwitterionic polymer.

21. A liquid composition for imparting to hair treated therewith static-free behavior, good comb-out and sheen, and high curl retention maintainable even at high relative humidity, consisting essentially of an aqueous solution cotaining from about 0.25 to about 10% by weight of a zwitterionic polymer containing at least 10% on a molar basis of zwitterionic moiety, a 24% solids aqueous solution of said polymer having a Brookfield viscosity of from about to 100,000 cps, said polymer being selected from a group consisting of (A) polymers of carboxy betaines having the repeating formula wherein R represents a polymerizable unsaturated group selected from the group consisting of acrylate, methacrylate, acrylamide and methacrylamide, R and R are hydrogen atoms or lower alkyl groups, x and y are integers from 1 to 3 inclusive, and R and R represent a hydrogen atom or an alkyl radical with the total sum of the carbon atoms in R and R not exceeding six, and

(B) copolymers of monomers (1) and (2), shown below:

(1) substituted acidic vinyl compounds having the general formula CR H=CR CO H wherein R represents a hydrogen atom or a carboxylic acid group and R represents a hydrogen atom, a chlorine atom or a methyl group, and

(2) substituted basic vinyl compounds having the general formula OH =CR COQ wherein R represents a hydrogen atom or a methyl group and Q is an organic radical containing a basic nitrogen-containing group, wherein said acidic and basic functionalities are retained in the copolymer structure and wherein the mole ratio of the basic monomer to acidic monomer in said copolymer is from 0.8:1 to 2.5:1, except where R; is CO H, the mole ratio is 1.7:1 to 5:1, wherein said aqueous hairsetting composition also contains an amount efiective for setting hair of a water-soluble hairsetting resin previously known for setting hair.

22. The composition of claim 21 wherein said previously known resin is polyvinyl pyrrolidone.

References Cited UNITED STATES PATENTS 2,744,130 5/1956 Winberg 260-482 2,777,872 1/1957 lShaoklett 260-482 2,833,650 5/1958 Shacklett 96-114 2,834,758 5/1958 Shacklett 260-78 2,846,417 8/1958 Shacklett 260-78 3,598,641 8/1971 Miller et al 117-138.8 E 3,671,305 6/1972 Brown et al. 117-1388 F 3,689,470 9/1972 Shachat et al. 260-861 N OTHER REFERENCES Mitra et al. J. Electroanal. Chem. 15, 399-404 (1967).

Ryabov et al., Tr. Khim. Khim. T eckhnoL, 1967(2), 49-51.

Ryabov et al., Tr. Kkim. Khim. TecknoL, 1968(1), 51-55.

MELVIN GOLDSTEIN, Primary Examiner US. Cl. X.R.

132-7; 260-2936 WB; 424-71, Dig. 2

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Classifications
U.S. Classification524/548, 524/555, 524/516, 524/551, 424/70.11, 424/DIG.200, 132/203
International ClassificationA61Q5/06, C08F20/34, A61K8/81, C08F20/52, C08F20/60
Cooperative ClassificationA61K2800/5428, C08F20/60, A61K8/8152, A61Q5/06, Y10S424/02, C08F20/52, C08F20/34
European ClassificationC08F20/52, C08F20/60, A61Q5/06, C08F20/34, A61K8/81K4