Neutralized crosslinked polymers of acrylamidoalkylsulfonic acids and N-vinylamides

• US 6,355,752 B1
• Filed: 02/10/2000
• Issued: 03/12/2002
• Est. Priority Date: 02/11/1999
• Status: Expired due to Term

• Current Assignee: Clariant Produkte Deutschland GmbH (Clariant AG)
• Original Assignee: Clariant GmbH (Clariant AG)
• Inventors: Löffler, Matthias, Brungs, Peter
• Primary Examiner(s): HENDERSON JR, CHRISTOPHER A
• Application Number:
  US09/501,904
• Time in Patent Office: 761 Days
• Field of Search: 526/287
• US Class Current: 526/287
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00

Abstract

Water-soluble or water-swellable polymers, preferably having a particle size no greater than 10 μm, which, in addition to from 0.01 to 5% by weight of crosslinking structures originating from monomers having at least two olefinic double bonds, comprise, in random distribution, from 1 to 50% by weight of the repeat structural unit (1) and from 49.99 to 98.99% by weight of the repeat structural unit (2),

in which R¹, R² and R³ independently of one another are a hydrogen atom or a methyl group, and Z is a C₁-C₄-alkylene group. These polymers are used as thickeners, preferably in cosmetic or pharmaceutical preparations.

Claims

1. A water-soluble or water-swellable polymer which, in addition to from 0.01 to 5% by weight of crosslinking structures originating from monomers having at least two olefinic double bonds, comprises, in random distribution, from 1 to 50% by weight of the repeat structural unit of the formula (1) and from 49.99 to 98.99% by weight of the repeat structural unit of the formula (2),

in which R¹, R² and R³ independently of one another are a hydrogen atom or a methyl group, and Z is a C₁-C₄-alkylene group.

2. The water-soluble or water-swellable polymer as claimed in claim 1 which, in addition to from 0.5 to 2% by weight of crosslinking structures originating from monomers having at least two olefinic double bonds, include, in random distribution, from 2 to 30% by weight of the repeat structural unit of the formula (1) and from 69.5 to 97.5% by weight of the repeat structural unit of the formula (2).

3. The water-soluble or water-swellable polymer as claimed in claim 1 which, in addition to from 0.5 to 2% by weight of crosslinking structures originating from monomers having at least two olefinic double bonds, includes, in random distribution, from 3 to 15% by weight of the repeat structural unit of the formula (1) and from 84.5 to 96.5% by weight of the repeat structural unit of the formula (2).

4. The water-soluble or water-swellable polymer as claimed in claim 1, wherein the repeat structural element of the formula (2) is derived from the ammonium salt of 2-acrylamido-2-methylpropanesulfonic acid.

5. The water-soluble or water-swellable polymer as claimed in claim 1, wherein the repeat structural element of the formula (1) is derived from N-vinylformamide.

6. The water-soluble or water-swellable polymer as claimed in claim 1, wherein the polymer has an average particle size of 10 μ

m or less.

7. The water-soluble or water-swellable polymer as claimed in claim 1, wherein the crosslinking structures are derived from dipropylene glycol diallyl ether, polyglycol diallyl ether, triethylene glycol divinyl ether, hydroquinone diallyl ether, tetraallyloxyethane or other allyl or vinyl ethers, polyfunctional alcohols, tetraethylene glycol diacrylate, triallylamine, trimethylolpropane diallyl ether, methylenebisacrylamide or divinylbenzene.

8. The water-soluble or water-swellable polymer as claimed in claim 1, wherein the crosslinking structures are derived from monomers of the formula (3),

in which R⁴ is hydrogen or methyl.

9. A process for the preparation of the water-soluble or water-swellable polymers as claimed in claim 1, which comprises

a) dissolving or dispersing from 49.99 to 98.99 parts by weight of the ammonium salt of acrylamidoalkylsulfonic acid of the formula (4),

 

in which R³ and Z are as defined above, in an alcoholic solvent or solvent mixture, or dissolving or dispersing from 49.99 to 98.99 parts by weight of the free acrylamidosulfonic acid derived from (4) in an alcoholic solvent and converting the acid into the ammonium salt by introducing ammonia or ammoniacal solution,

b) adding to the solution or dispersion obtained as in a) from 1 to 50 parts by weight of the N-vinylcarboxamide of the formula (5)

 

in which R¹ and R² are as defined in claim 1,

c) adding to the solution or dispersion obtained as in b) from 0.01 to 5 parts by weight of one or more crosslinkers having at least two double bonds, and

d) starting the polymerization in a manner known per se using free-radical-forming compounds, and carrying out the polymerization at a temperature of from 10 to 150°

C., the alcoholic solvent or solvent mixture used in a) being chosen such that the resulting polymers are largely insoluble in the solvent or solvent mixture.