IP Library Granted Patent US 8,629,224
Granted Patent B2
US 8,629,224 · App. 12/747,727 · Granted Jan 14, 2014

Water-soluble or water-swellable polymers on the basis of salts of acryloyldimethyltaurine acid or the derivatives thereof, the production thereof and the use thereof as thickener, stabilizer and consistency agents

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Quick Facts
Patent No.
US 8,629,224
App. No.
12/747,727
Granted
Jan 14, 2014
Kind
B2
Abstract

Polymers are described comprising a) one or more of the recurring structural units of the formula (1) where R 1 is hydrogen, methyl or ethyl and A is C 1 -C 8 alkylene, and Q + is H + , NH 4 + , Li + , Na + , K + , ½ Ca ++ , ½ Mg ++ , ½ Zn ++ or ⅓ Al +++ , and the neutralization degree of the structural units of formula (1) is 50 to 100 mol-%, and b) one or more of the recurring structural units of the formula (2) where R 1 and A are R 1 and A from formula (1) and X + is [HNR 5 R 6 R 7 ] + , where R 5 , R 6 and R 7 can independently from each other be hydrogen, a linear or branched alkyl group with 1 to 22 carbon atoms, a linear or branched, simple or polyunsaturated alkenylene group with 2 to 22 carbon atoms, a C 6 -C 22 -alkylamidopropyl group, a linear monohydroxyalkyl group with 2 to 10 carbon atoms or a linear or branched dihydroxyalkyl group with 3 to 10 carbon atoms, and wherein at least one of the groups R 5 , R 6 and R 7 is not hydrogen.

Claims (43)

1. A polymer comprising

a) at least one structural repeat unit of the formula (1)

wherein R 1 is hydrogen, methyl or ethyl and A is C 1 -C 8 -alkylene, and Q + is H + , NH 4 + , Li + , Na + , K + , ½ Ca ++ , ½ Mg ++ , ½ Zn ++ or ⅓ Al +++ , and the degree of neutralization of the structural units of the formula (1) is from 50 to 100 mol %,

and

b) at least one structural repeat unit of the formula (2)

wherein R 1 and A have the definition of R 1 and A from formula (1) and X + is selected from the group consisting of laurylamidopropyldimethylammonium, stearylamidopropyldimethylammonium, behenylamidopropyldimethylammonium, C 12-18 -alkyldimethylammonium, and C 20 -C 22 -alkyldimethylammonium ion,

with the proviso that the molar ratio of the structural units of the formula (1) in which Q + is NH 4 + , Li + , Na + , K + , Ca ++ , Mg ++ , Zn ++ or Al +++ to the structural units of the formula (2) is from 97:3 to 55:45, and a corresponding alkylammonium chloride having a critical micelle concentration (CMC) <15 g/l,

and

d) 0% to 8% by weight based on the total weight of the polymer of crosslinking structural units originating from monomers having at least two olefinic double bonds.

2. The polymer as claimed in claim 1 , comprising

ab) 49.99% to 98.99% by weight based on the total weight of the polymer of a mixture of the structural repeat units of the formulae (1) and (2),

c1) 1% to 50% by weight based on the total weight of the polymer of the structural repeat units of the formula (3)

where n is an integer from 2 to 9,

or

c2) 1% to 50% by weight based on the total weight of the polymer of a mixture of the structural repeat unit of the formula (3) and the structural repeat unit of the formula (4)

where R 2 and R 3 are alike or different and are hydrogen or a linear or branched alkyl group having 1 to 22 carbon atoms or a linear or branched, singly or multiply unsaturated alkenyl group having 2 to 22 carbon atoms, and R 4 is hydrogen, methyl or ethyl,

and

d) 0% to 8% by weight based on the total weight of the polymer of crosslinking structural units originating from monomers having at least two olefinic double bonds.

3. The polymer as claimed in claim 1 , comprising

ab) 92% to 99.99% by weight based on the total weight of the polymer of a mixture of the structural repeat units of the formulae (1) and (2) and

d) 8% to 0.01% by weight based on the total weight of the polymer of crosslinking structural units originating from monomers having at least two olefinic double bonds.

4. The polymer as claimed in claim 2 , comprising

69.5% to 97.5% by weight based on the total weight of the polymer of a mixture of the structural units of the formulae (1) and (2),

2% to 30% by weight based on the total weight of the polymer of the structural units of the formula (3) or of a mixture of the structural units of the formulae (3) and (4),

and

0.2% to 3% by weight based on the total weight of the polymer of crosslinking structural units originating from monomers having at least two olefinic double bonds.

5. The polymer as claimed in claim 1 , wherein the structural units of the formulae (1) and (2) are derived from 2-acrylamido-2-methylpropanesulfonic acid.

6. The polymer as claimed in claim 2 , wherein the structural units of the formula (3) are derived from N-vinylpyrrolidone.

7. A polymer as claimed in claim 1 , wherein R 2 and R 3 in the structural units of the formula (4) are hydrogen or methyl and R 4 is hydrogen.

8. The polymer as claimed in claim 1 , wherein the non-H + counterion Q + in the structural units of the formula (1) is selected from the group consisting of NH 4 + , alkali metal + , and alkaline earth metal ++ .

9. A process for preparing a polymer as claimed in claim 1 , comprising the steps of

i) dispersing or dissolving monomers from which the structural units of the formulae (1) and (2) derive, and additionally, if desired, monomers from which the structural units of the formula (3) or of the formulae (3) and (4) derive, in a protic solvent,

ii) neutralizing the dispersion or solution from step i) with ammonia or with a base containing Li + , Na + , K + , Ca ++ , Mg ++ , Zn ++ or Al +++ , and with an alkylamine,

iii) optionally, adding one or more crosslinkers having at least two olefinic double bonds to the neutralized dispersion or solution from step ii) and

iv) initiating the polymerization by adding a free-radical-forming compound.

10. A thickener, bodying agent, emulsifier, sensorial additive, solubilizer, dispersant, lubricant, adhesive or stabilizer composition, comprising at least one polymer as claimed in claim 1 .

11. A thickener, bodying agent, emulsifier, sensorial additive, solubilizer, dispersant, lubricant, adhesive or stabilizer composition as claimed in claim 10 having an oil fraction of >5% by weight, based on the completed composition.

12. A cosmetic, pharmaceutical or dermatological composition comprising at least one polymer as claimed in claim 1 .

13. A composition as claimed in claim 12 , wherein the composition is in the form of a fluid, gel, oil, foam, spray, lotion or cream.

14. A composition as claimed in claim 12 , wherein the composition is in the form of an oil-in-water emulsion containing no emulsifiers or surfactants.

15. A composition as claimed in claim 12 , wherein the composition has a pH of 2 to 6.5.

16. A composition as claimed in claim 12 , wherein the composition further comprises at least one electrolyte.

17. A composition as claimed in claim 12 , wherein the composition is in the form of a sunscreen composition and further comprises one or more sun protection filters for protecting the hair and the skin from UV rays.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2015
From: CLARIANT FINANCE (BVI) LIMITED
To: CLARIANT INTERNATIONAL LTD.
Reel/Frame 036949/0673 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2010
From: LOEFFLER, MATTHIAS; LINDNER, THOMAS; BACK, UTE; HORNUNG, MICHAEL
To: CLARIANT FINANCE (BVI) LIMITED
Reel/Frame 024524/0717 →