Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
1999-01-25
2001-08-07
Zitomer, Fred (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S303100, C526S306000, C526S307100, C526S307300, C526S310000, C526S312000, C424S070100
Reexamination Certificate
active
06271327
ABSTRACT:
The invention relates to water-soluble polymers, to processes for their preparation and to their use in cosmetic compositions.
Polymers are widely employed in cosmetology and medicine. In soaps, creams and lotions, for example, they generally serve as formulation auxiliaries, for example as thickener, foam stabilizer or water-absorbent, or else to lessen the irritation caused by other ingredients or to improve the dermal application of active ingredients. Their function in hair cosmetology, in contrast, is to influence the properties of the hair. Thus conditioners are used in order to improve the dry and wet combing properties, feel, luster and appearance of the hair and to give it antistatic properties. Furthermore, they may have a setting effect, by forming hydrophobic films on the hair.
It is preferred to use water-soluble polymers having polar, frequently cationic functionalities, which have a greater affinity for the negatively charged surface of the hair. The structure and mode of action of various hair treatment polymers have been described in Cosmetics & Toiletries 103 (1988) 23. Examples of customary commercial conditioning polymers are cationic hydroxyethylcellulose, cationic polymers based on N-vinylpyrrolidone, acrylamide and diallyldimethylammonium chloride, or silicones.
U.S. Pat. No. 4,713,236 describes hair conditioners based on polymers containing vinylamine units. Mention is made therein in particular of polyvinylamine and its salts, &agr;-substituted polyvinylamines, for example poly (&agr;-aminoacrylic acid), or else copolymers containing, in addition to vinylamine, comonomers such as vinyl alcohol, acrylic acid, acrylamide, maleic anhydride, vinylsulfonate and 2-acrylamido-2-methylpropanesulfonic acid.
U.S. Pat. No. 5,478,553 discloses the use of homo- and copolymers of N-vinylformamide as hairsetting agents, especially in water-containing gels. Possible comonomers listed there are styrene, acrylic and methacrylic acid, and their esters and amides, vinyl esters and vinyl ethers. WO 96/03969, moreover, describes the use of such polymers as conditioners for shampoos.
JP 06 122 725 makes mention, inter alia, of the use of pulverulent N-vinylformamide homo- and copolymers in the cosmetics field.
Hydrolyzed oligomers of N-vinylformamide which can be employed as a constituent of body care compositions are known from U.S. Pat. No. 5,373,076.
EP 510 246 and Japanese Specification J0 3223-304 disclose crosslinked, predominantly anionic homo- and copolymers of N-vinylcarboxamides which are employed as water absorbers and thickeners in the cosmetics field. In addition, copolymers of acrylamide and methacrylic acid which may include N-vinylcarboxamides as well, as further monomers, are likewise employed as thickeners in DE 34 27 220.
EP 452 758 describes the use of water-soluble polymers containing, inter alia, N-vinylcarboxamide units as constituents of gels for dermal cosmetic and medical applications. According to DE 38 17 425, crosslinked hydrogels can also be used for this purpose.
The conditioner polymers known from the prior art, however, are still not entirely satisfactory. There is therefore a need for additional conditioner polymers having improved properties.
N-Vinylamide polymers with various structures are also known from other technical fields.
For example, polymers containing N-vinyl-N-alkylcarboxamide units are described in DE-A 28 29 652. Poly-N-vinyl-N-methylformamide is specified in U.S. Pat. No. 3,558,581, poly-N-vinyl-N-methylacetamide in GB 1 082 016.
Homopolymers of N-vinylformamide are known from U.S. Pat. No. 4,421,602 and EP-B-0 071 050. These polymers serve as a precursor for polymers containing copolymerized vinylamine units. For example, a description is given of copolymers containing from 90 to 10 mol-% of N-vinylformamide units and from 10 to 90 mol-% of vinylamine units. These polymers are obtained by free-radical polymerization of N-vinylformamide with subsequent hydrolytic cleavage of some of the formyl radicals using acids or bases. These polymers find application as auxiliaries in papermaking or as sludge flocculants.
EP 0 216 387 describes copolymers containing not only N-vinylformamide but also other ethylenically unsaturated monomers such as vinyl acetate, vinyl propionate, C
1
- to C
4
-alkyl vinyl ethers, esters, nitriles and amides of acrylic and methacrylic acid, and N-vinylpyrrolidone. Partial or complete hydrolysis of these copolymers likewise leads to copolymers containing copolymerized vinylamine units. EP 0 251 182 discloses copolymers which in addition to N-vinylformamide and vinylamine also contain acrylonitrile units, with or without small proportions of acrylamide units and acrylic acid units. These copolymers too find application in the paper industry.
The preparation of these known polymers is generally by free-radical homopolymerization or copolymerization of the corresponding monomers. owing to the poor availability of specifically substituted N-vinylcarboxamides, or their poor polymerizability, it is appropriate, by reaction of primary and secondary polymers containing vinylamine units with carboxylic acid derivatives, to obtain N-vinylcarboxamide functions. Macromol. Chem. Phys. 195 (1994) 679 describes the reaction of polyvinylamine with aliphatic carboxylic acid chlorides. The reaction with aromatic sulfonic acid chlorides to form the corresponding sulfonamides is known from U.S. Pat. No. 4,403,072 and U.S. Pat. No. 4,275,002. The formation of amide functions starting from polymers containing copolymerized vinylamine units, by reaction with carboxylic esters, on the other hand, is not described.
The reaction of polyvinylamine or its hydrochloride with various sugar lactones, for example glucolactone, is described in Macro-mol. Chem. 184 (1983) 1441. These reactions are generally carried out in nonaqueous polar solvents, requiring the complex isolation beforehand of polymers synthesized in aqueous solution.
Badesso et al. in Adv. Chem. Ser. 248 (1996) 490-504 describe preparing polyvinylamine by hydrolyzing poly(N-ethenylformamide). The preparation of certain polyvinylamid derivatives is also described. Described inter alia is a product of reacting polyvinylamine and &ggr;-butyrolactone in which 24 mol % of the amine units are substituted by a radical of the formula
—C (O)—CH
2
—CH
2
—CH
2
—OH.
The solvent used is methanol. Possible fields of use specified for the butyrolactone derivative are wastewater treatment and papermaking. A possibly advantageous possibility of employing the derivative in cosmetics is not mentioned.
It is an object of the present invention, therefore, to provide novel N-vinylamide polymers having improved cosmetic properties, and in particular to provide polymers which enhance the wet combing properties of head hair.
We have found that this object is achieved, surprisingly, by using polymers whose essential structural elements comprise hydroxy-substituted N-vinylcarboxamide units.
Unless specified otherwise, the following specific description of the invention is subject to the following definitions.
Alkyls that can be used in accordance with the invention comprise straight-chain or branched, saturated chains of 1 to 20 carbons, possible examples being alkyls of 1 to 12 carbons, such as the C
1
-C
6
-alkyls methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, t-butyl, n-pentyl, sec-pentyl, i-pentyl, n-hexyl, 1-, 2- or 3-methylpentyl; and longer-chain radicals, such as unbranched heptyl, octyl, nonyl, decyl, undecyl, lauryl and the singly or multiply branched analogs thereof; and also alkyls with more than 12 carbons, such as unbranched tridecyl, myristyl, pentadecyl, palmityl, heptadecyl, stearyl, nonadecyl and eicosyl and the singly or multiply branched analogs thereof.
Cycloalkyls that can be used in accordance with the invention comprise, in particular, C
3
-C
12
-cycloalkyls, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylethyl, cyc
Hossel Peter
Niessner Manfred
Nilz Claudia
Rubenacker Martin
BASF - Aktiengesellschaft
Keil & Weinkauf
Zitomer Fred
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