(Meth)acrylic acid esters of unsaturated aminoalcohols and preparation thereof

• US 7,652,111 B2
• Filed: 11/18/2004
• Issued: 01/26/2010
• Est. Priority Date: 11/25/2003
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Schwalm, Reinhold, Dietsche, Frank, Riegel, Ulrich, Daniel, Thomas, Elliott, Mark, Hermeling, Dieter
• Primary Examiner(s): Wu; David
• Assistant Examiner(s): BERNSHTEYN, MICHAEL
• Application Number:
  US10/576,892
• Publication Number:
  US 20070043191A1
• Time in Patent Office: 1,895 Days
• Field of Search: 526/319, 560/222
• US Class Current: 526/319
• CPC Class Codes: C07C 219/08 having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C08F 20/40 Esters of unsaturated alcohols , e.g. allyl (meth)acrylate
• CPC Class Codes: C08F 220/14 Methyl esters , e.g. methyl (meth)acrylate
• CPC Class Codes: C08F 226/02 by a single or double bond to nitrogen
• CPC Class Codes: C08F 226/04 Diallylamine

Abstract

Disclosed are novel (meth)acrylic esters of unsaturated amino alcohols, a process for their preparation and their use for preparing crosslinked swellable hydrogel-forming polymers and crosslinked swellable hydrogel-forming polymers.

Claims

1. (Meth)acrylic esters of unsaturated aminoalcohols of general formula (I)

2. (Meth)acrylic esters of claim 1 wherein

R¹, R², R³, R⁴, and R⁵ are each hydrogen,

R⁶ is C₁ to C₃ alkyl, of which C₃ alkyl may be branched or unbranched,

R⁷ is hydrogen or methyl,

m is 0 or 1,

n is 1 or 2,

o is 0 or 1,

p is 1 or 2,

q is an integer from 3 to 40,

the sum total of n, o, and p is 3, and

A represents identical or different radicals selected from the group consisting of

3. (Meth)acrylic esters of claim 1 wherein

R¹, R², R³, R⁴, and R⁵ are each hydrogen,

R⁷ is hydrogen or methyl,

m is 1,

n is 1 or 2,

o is 0,

p is 1 or 2,

q is an integer from 5 to 20,

the sum total of n, o, and p is 3, and

A is

4. A process for preparing the (meth)acrylic esters of claim 1 comprising unsaturated aminoalcohols being transesterified with lower (meth)acrylic esters in the presence of a catalyst, a released lower alcohol being distilled off during the transesterification, optionally as an azeotrope, and unconverted lower (meth)acrylic ester being distilled off after the transesterification has ended, optionally diluted with water and filtered.

6. A swellable hydrogel-forming polymer comprising a copolymerized (meth)acrylic ester of an unsaturated aminoalcohol of claim 2 as an internal crosslinker.

7. A swellable hydrogel-forming polymer comprising a copolymerized (meth)acrylic ester of an unsaturated aminoalcohol of claim 3 as an internal crosslinker.

10. A process for preparing crosslinked swellable hydrogel-forming polymers of claim 6 which comprises polymerizing an aqueous mixture comprising a hydrophilic monomer, optionally at least one further monoethylenically unsaturated compound, at least one (meth)acrylic ester of unsaturated aminoalcohols, at least one free-radical initiator, optionally at least one grafting base, and optionally a reaction mixture obtained being post-crosslinked, dried, and brought to the desired particle size.

11. A process for preparing crosslinked swellable hydrogel-forming polymers of claim 7 which comprises polymerizing an aqueous mixture comprising a hydrophilic monomer, optionally at least one further monoethylenically unsaturated compound, at least one (meth)acrylic ester of unsaturated amino alcohols, at least one free-radical initiator, optionally at least one grafting base, and optionally a reaction mixture obtained being post-crosslinked, dried, and brought to the desired particle size.

12. The swellable hydrogel-forming polymer of claim 5 wherein the internal crosslinker of general formula (I) according to claim 1 is copolymerized with an acid functional monoethylenically unsaturated monomer, a salt thereof, or mixtures thereof.

13. The swellable hydrogel-forming polymer of claim 12 wherein the acid functional monoethylenically unsaturated monomer comprises acrylic acid, methacrylic acid, a salt thereof, or mixtures thereof.

14. The swellable hydrogel-forming polymer of claim 6 wherein the internal crosslinker according to claim 2 is copolymerized with an acid functional monoethylenically unsaturated monomer, a salt thereof, or mixtures thereof.

15. The swellable hydrogel-forming polymer of claim 14 wherein the acid functional monoethylenically unsaturated monomer comprises acrylic acid, methacrylic acid, a salt thereof, or mixtures thereof.

16. The swellable hydrogel-forming polymer of claim 7 wherein the internal crosslinker according to claim 3 is copolymerized with an acid functional monoethylenically unsaturated monomer, a salt thereof, or mixtures thereof.

17. The swellable hydrogel-forming polymer of claim 16 wherein the acid functional monoethylenically unsaturated monomer comprises acrylic acid, methacrylic acid, a salt thereof, or mixtures thereof.

5. A swellable hydrogel-forming polymer comprising a copolymerized internal crosslinker of a general formula (I)

8. A process for preparing crosslinked swellable hydrogel-forming polymers of claim 5 which comprises polymerizing an aqueous mixture comprising a hydrophilic monomer, optionally at least one further monoethylenically unsaturated compound, at least one (meth)acrylic ester of unsaturated aminoalcohols, at least one free-radical initiator, optionally at least one grafting base, and optionally a reaction mixture obtained being postcrosslinked, dried, and brought to the desired particle size.

9. A hygiene article comprising a crosslinked swellable hydrogel-forming polymer of claim 5.