IP Library Granted Patent US 7,186,405
Granted Patent B2
US 7,186,405 · App. 10/433,113 · Granted Mar 6, 2007

Deodorants and anti-perspirants

Assignee: Clariant Produkte (Deutschland) GmbH
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Quick Facts
Patent No.
US 7,186,405
App. No.
10/433,113
Granted
Mar 6, 2007
Kind
B2
Abstract

The invention relates to deodorants and antiperspirants comprising at least one copolymer. The copolymer is obtained by free-radical copolymerization of A) acryloyldimethyltaurine and/or acryloyldimethyltaurates, and B) optionally, one or more further olefinically unsaturated, noncationic comonomers, C) optionally, one or more olefinically unsaturated, cationic comonomers, D) optionally, one or more silicon-containing component(s), E) optionally, one or more fluorine-containing component(s), F) optionally, one or more macromonomers, G) optionally, the copolymerization taking place in the presence of at least one polymeric additive, H) with the proviso that component A) is copolymerized with at least one component selected from one of the groups D) to G).

Claims (59)

1. A deodorant or antiperspirant which comprises at least one copolymer obtained by free-radical copolymerization of

A) acryloyldimethyltaurine or acryloyldimethyltaurate or a mixture thereof,

B) optionally, one or more further olefinically unsaturated, noncationic, comonomer which has at least one oxygen, nitrogen, sulfur or phosphorus atom and has a molecular weight of less than 500 g/mol,

C) optionally, one or more olefinically unsaturated, cationic comonomer which has at least one oxygen, nitrogen, sulfur or phosphorus atom and possess a molecular weight of less than 500 g/mol,

D) one or more silicon-containing component capable of free-radical polymerization and having a functionality of at least one, at least one silicon-containing component being a compound selected from the group consisting of

in which f=2 to 500,

in which f=2 to 500,

in which f=2–500, and mixtures thereof,

E) optionally, one or more fluorine-containing components capable of free-radical polymerization and having a functionality of at least one,

F) optionally, one or more olefinically mono- or polyunsaturated, optionally crosslinking macromonomers each possessing at least one oxygen, nitrogen, sulfur or phosphorus atom and having a number-average molecular weight of greater than or equal to 200 g/mol, the macromonomers not being a silicon-containing component D) fluorine-containing component E),

G) optionally the copolymerization taking place in the presence of at least one polymeric additive having number-average molecular weights of from 200 g/mol to 10 8 g/mol, and

at least one compound selected from the group consisting of glycerol, an active antimicrobial substance, an astringent, and mixtures thereof.

2. The deodorant or antiperspirant as claimed in claim 1 , wherein the comonomer B) is selected from the group consisting of unsaturated carboxylic acids, salts of unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, esters of unsaturated carboxylic acids with aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic alcohols having 1 to 22 carbon atoms, open-chain N-vinyl amides, cyclic N-vinyl amides having a ring size of from 3 to 9, amides of acrylic acid, amides of methacrylic acid, amides of substituted acrylic acids, amides of substituted methacrylic acids, 2-vinylpyridine, 4-vinylpyridine, vinyl acetate, styrene, acrylonitrile, vinyl chloride, vinylidene chloride, tetrafluoroethylene, vinylphosphonic acid or esters or salts thereof, vinylsulfonic acid or esters or salts thereof, allylphosphonic acid or esters or salts thereof, methallylsulfonic acid or esters or salts thereof, and mixtures thereof.

3. The deodorant or antiperspirant as claimed in claim 1 , wherein the comonomer C) is selected from the group consisting of diallyldimethylammonium chloride (DADMAC), [2 -methacryloyloxy)ethyl]trimethylammonium chloride (MAPTAC), [2-(acryloyloxy)ethyl)]trimethylammonium chloride, [2 -methacryloyloxy)ethyl]trimethylammonium chloride, [2-(acryloyloxy)ethyl)]trimethylammonium chloride, N-methyl-2-vinylpyridinium chloride, N-methyl-4-vinylpyridinium chloride, dimethylaminoethyl methacrylate, dimethylaminopropylmethacrylamide, methacryloylethyl N-oxide, methacryloylethylbetaine, and mixtures thereof.

4. The deodorant or antiperspirant of claim 1 , wherein the fluorine-containing component E) is a compound of formula (II)

R 1 —Y—C r H 2r C s F 2s CF s   (II)

where

R 1 represents a polymerizable function of a vinylically unsaturated compound; Y is a chemical bridge, and

r, s are stoichiometric coefficients which independently of one another are numbers between 0 and 200.

5. The deodorant or antiperspirant of claim 1 , wherein the macromonomer F) is of formula (III)

R 1 —Y—[(A) v —(B) w —(C) x —(D) z ]—R 2   (III)

where R 1 represents a polymerizable function from a vinylically unsaturated compound;

Y is a bridging group;

A, B, C, and D independently of one another are discrete chemical repeating units;

v, w, x, and z independently of one another amount to from 0 to 500, the sum of v, w, x, and z being on average ≧1; and

R 2 is a linear or branched aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic (C 1 –C 50 ) hydrocarbon radical, OH, —NH 2 or —N(CH 3 ) 2 or is [—Y—R 1 ].

6. The deodorant or antiperspirant of claim 1 , wherein the polymeric additive G) is selected from the group consisting of polyalkylene glycol, alkylpolyglycol, and mixtures thereof or a homopolymer or copolymer of a compound selected from the group consisting of N-vinylformamide, N-vinylacetamide, N-vinylpyrrolidone, ethylene oxide, propylene oxide, acryloyldimethyltaurine, N-vinylcaprolactam, N-vinylmethylacetamide, acrylamide, acrylic acid, methacrylic acid, N-vinylmorpholide, hydroxymethyl methacrylate, diallyldimethylammonium chloride (DADMAC), [2-(methacryloyloxy)ethyl]trimethylammonium chloride (MAPTAC); and mixtures thereof.

7. The deodorant or antiperspirant of claim 1 , wherein the copolymerization takes place in the presence of at least one polymeric additive G).

8. The deodorant or antiperspirant of claim 1 , wherein the copolymer is crosslinked.

9. The deodorant or antiperspirant of claim 1 , wherein the copolymer is prepared by precipitation polymerization in tert-butanol.

10. The deodorant or antiperspirant of claim 1 , wherein the copolymer is water-soluble or water-swellable.

11. The deodorant or antiperspirant of claim 1 , which comprises, based on a finished composition, from 0.01 to 10% by weight of the copolymer.

12. The deodorant or antiperspirant of claim 1 , which comprises from 0.01 to 89% by weight of water.

13. The deodorant or antiperspirant of claim 1 , which comprises up to 10% by weight of glycerol.

14. The deodorant or antiperspirant of claim 1 , which comprises an active antimicrobial substance.

15. The deodorant or antiperspirant of claim 1 , which comprises astringent.

16. The deodorant or antiperspirant of claim 1 , which is in the form selected from the group consisting of a lotion, cream, stick, multiphase stick, spray, roll-on preparation, and powder.

17. The deodorant or antiperspirant of claim 4 wherein R 1 is a radical selected from the group consisting of vinyl, allyl, methallyl, methylvinyl, acryloyl, crotonyl, senecionyl, itaconyl, maleyl, fumaryl, styryl, and mixtures thereof.

18. The deodorant or antiperspirant of claim 4 , wherein the chemical bridge Y is selected from the group consisting of —O—, —C(O)—, —C(O)—O—, —S—, —O—CH 2 —CH(O—)—CH 2 OH, —O—CH 2 —CH(OH)—CH 2 —O—, —O—SO 2 —O—, —O—S(O)—O—, —PH—, —P(CH 3 )—, —PO 3 —, —NH—, —N(CH 3 )—, —O—(C 1 –C 50 )alkyl-O—, —O-phenyl-O—, —O-benzyl-O—, —O—(CH 5 –CH 8 )cycloalkyl-O—, —O—(C 1 –C 50 )alkenyl-O—, —O—(CH(CH 3 )—CH 2 —O) n —, —O—(CH 2 —CH 2 —O) n —, —O—([CH—CH 2 —O] n —[CH 2 —CH 2 —O] m ) o —, where n, m, and o independently of one another denote numbers from 0 to 200, and mixtures thereof.

19. The deodorant or antiperspirant of claim 5 wherein, R 1 is a radical selected from the group consisting of vinyl, allyl, methallyl, methylvinyl, acryloyl, methacryloyl, crotonyl, senecionyl, itaconyl, maleyl, fumaryl, styryl, and mixtures thereof.

20. The deodorant or antiperspirant of claim 5 , wherein the bridging group Y is selected from the group consisting of —O—, —S—, —C(O)—, —C(O)—O—, —O—CH 2 —CH(O—)—CH 2 OH, —O—CH 2 —CH(OH)—CH 2 O—, —O—SO 2 —O—, —O—SO—O—, —PH—, —P(CH 3 )—, —PO 3 —, —NH—, —N(CH 3 )—, and mixtures thereof.

21. The deodorant or antiperspirant of claim 5 wherein the discrete repeating units of A, B, C, and D are originating from a unit selected from the group consisting of acrylamide, methacrylamide, ethylene oxide, propylene oxide, AMPS, acrylic acid, methacrylic acid, methyl methacrylate, acrylonitrile, maleic acid, vinyl acetate, styrene, 1,3-butadiene, isoprene, isobutene, diethylacrylamide, and dilsopropylacrylamide.

22. The deodorant or antiperspirant of claim 5 wherein the discrete repeating units of A, B, C, and D are originating from a unit of ethylene oxide or propylene oxide.

23. The deodorant or antiperspirant of claim 5 , wherein v, w, x, and z independently of one another amount to from 1 to 30.

24. A deodorant or antiperspirant which comprises at least one copolymer obtained by free-radical copolymerization of acryloyldimethyltaurine or acryloyldimethyltaurate or mixtures thereof and

a) one or more silicon-containing component capable of free-radical polymerization and having a functionality of at least one, and selected from the group consisting of

in which f=2 to 500,

in which f=2to 500,

in which f=2–500, and mixtures thereof,

with or in the presence of at least one component selected from the group consisting of:

b) one or more fluorine-containing component capable of free-radical polymerization and having a functionality of at least one,

c) one or more olefinically mono- or polyunsaturated, macromonomer each possessing at least one oxygen, nitrogen, sulfur or phosphorus atom and having a number-average molecular weight of greater than or equal to 200 g/mol, the macromonomer not being the silicon-containing component a) or the fluorine-containing component b), and

d) at least one polymeric additive having number-average molecular weights of from 200 g/mol to 10 9 g/mol, and

at least one compound selected from the group consisting of glycerol, an active antimicrobial substance, an astringent, and mixtures thereof.

25. The deodorant or antiperspirant of claim 24 , wherein the copolymerization further comprises:

e) one or more further olefinically unsaturated, noncationic comonomer which has at least one oxygen, nitrogen, sulfur or phosphorus atom and has a molecular weight of less than 500 g/mol, or

f) one or more olefinically unsaturated, cationic comonomer which has at least one oxygen, nitrogen, sulfur or phosphorus atom and has a molecular weight of less than 500 g/mol.

26. The deodorant or antiperspirant of claim 24 , wherein said macromonomer c) is crosslinking.

27. The deodorant or antiperspirant of claim 25 , wherein said olefinically unsaturated, noncationic comonomer e) is crosslinking.

Assignments (4)
CHANGE OF NAME Recorded Dec 14, 2006
From: CLARIANT GMBH
To: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH
Reel/Frame 018632/0302 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2006
From: LOEFFLER, MATTHIAS; MORSHHAEUSER, ROMAN
To: CLARIANT GMBH
Reel/Frame 018572/0393 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2006
From: LOEFFLER, MATTHIAS; MORSCHHAEUSER, ROMAN
To: CLARIANT GMBH
Reel/Frame 018601/0019 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2006
From: LOEFFLER, MATTHIAS; MORSCHHAEUSER, ROMAN
To: CLARIANT GMBH
Reel/Frame 018610/0660 →
Priority Claims (1)
DE 100 59 823 · Dec 1, 2000 · national
Continuity (1)
Related Publication 20040096409A1 · May 20, 2004