Easily synthesizable, spontaneously water-soluble, essentially voc-free, environmentally friendly (meth)acrylamido-functional siloxanol systems, process for preparation thereof and use

Patent metadata

Field	Value
Publication number	US-9765095-B2
Application number	US-201615070417-A
Country	US
Kind code	B2
Filing date	Mar 15, 2016
Priority date	Apr 20, 2012
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

The invention relates to a composition and to a process for producing the composition comprising essentially water-soluble (meth)acrylamido-functional siloxanols, and to the use thereof.

First claim

The invention claimed is:

1. A composition, comprising at least one water-soluble acrylamido-functional siloxanol oligomer of formula (V):
(R 1 O)[(R 1 O) 1−a (R 2 ) a Si(C) 1+b O] u [(Y)Si(C) 1+b O] u′ R 1 .(HX)z   (V),

obtained by:
a) reacting a component A with an acrylic anhydride (B); and optionally
b) removing at least a portion of hydrolyzed alcohol, with optional addition of water for removal of the hydrolyzed alcohol,
wherein:
the component A is at least one aminoalkyl-functionalized silicon compound selected from the group consisting of
(i) an aminoalkyl-functional alkoxysilane or a mixture of aminoalkyl-functional alkoxysilanes, each in the presence of water,
(ii) a hydrolysis or condensation product of at least one aminoalkyl-functional alkoxysilane, and
(iii) a mixture comprising at least one aminoalkyl-functional alkoxysilane and a hydrolysis product, a condensation product, or both, of the at least one aminoalkyl-functional alkoxysilane:,
C represents an acrylamido group;
Y represents OR 1 or, in crosslinked and/or three-dimensionally crosslinked structures, independently to OR 1 or O 1/2 ;
R 1 represents hydrogen;
R 2 represents a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms;
HX is an acid, where X is an inorganic or organic acid radical;
a is 0 or 1;
b is 0 or 1;
u is an integer greater than or equal to 2;
u′ is greater than or equal to 1;
z is greater than or equal to 0;
(u +u′) is greater than or equal to 2; and
the composition is essentially free of diluents and releases essentially no alcohol during a crosslinking.

2. The composition according to claim 1 , wherein:
the aminoalkyl-functional alkoxysilane is defined by formula (I):
(R 1 O) 3−a−b (R 2 ) a Si(B) 1+b   (I);

B independently represents a group of formula (II):
—(CH 2 ) c —[(NH)(CH 2 ) d ] e [(NH)](CH 2 ) f ] g NH (2−h) R 3 h   (II),

R 1 are each independently a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms,
R 2 are each independently a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms,
R 3 are each independently a linear, branched or cyclic alkyl, aryl or alkylaryl group having 1 to 8 carbon atoms,
a is 0 or 1,
b is 0, 1 or 2,
c is 1, 2, 3, 4, 5 or 6,
d is 1, 2, 3, 4, 5 or 6,
e is 0, 1, 2, 3, 4, 5 or 6,
f is 1, 2, 3, 4, 5 or 6,
g is 0, 1, 2, 3, 4, 5 and 6, and
h is independently 0 or 1,
or

B is of formula (III):
—(CH 2 ) j —NH 2−p (CH 2 —CH 2 —NH 2 ) p   (III),

j is 1, 2 or 3, and
p is 0, 1 or 2.

3. The composition according to claim 1 , wherein:
the acrylic anhydride is of formula (IV):
(CHR 5 ═CR 4 CO) 2 O  (IV);

R 4 are each independently a hydrogen atom or a methyl group; and
R 5 are each independently a hydrogen atom or a methyl group.

4. An article, comprising the composition according to claim 1 , wherein the article is selected from the group consisting of an adhesion promoter, a dental impression compound, a polymer additive, an adhesive, a sealant, and a fiber composite material.

5. The composition according to claim 1 , wherein C is selected from the group consisting of
—(CH 2 ) c —[(NH)(CH 2 ) d ] e [(NH)](CH 2 ) f ] g NH (1−h) R 3 h —(CO)CR 4 ═CHR 5 ,

—(CH 2 ) j —NH(CH 2 —CH 2 —NH)—(CO)CR 4 ═CHR 5 , and

—(CH 2 ) j —NH 2−p (CH 2 —CH 2 —NH—(CO)CR 4 ═CHR 5 ) p ,

wherein:
c 1, 2, 3, 4, 5 or 6;
d 1, 2, 3, 4, 5 or 6;
e 0, 1, 2, 3, 4, 5 or 6;
f 1, 2, 3, 4, 5 or 6;
g 0, 1, 2, 3, 4, 5 or 6;
h 0 or 1;
j 1, 2 or 3;
p 0, 1 or 2;
R 3 is a linear, branched or cyclic alkyl, aryl or alkylaryl group having 1 to 8 carbon atoms; and
R 5 a hydrogen atom or a methyl group.

Assignees

• Wassmer Christian
• Standke Burkhard
• Schlosser Thomas
• Krause Regina
• Evonik Degussa Gmbh

Inventors

• Wassmer Christian
• Standke Burkhard
• Schlosser Thomas
• Krause Regina

Classifications

• A61K6/90

  Compositions for taking dental impressions · CPC title

• C07F7/081 Primary

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• C07F7/0834

  Compounds having one or more O-Si linkage (for compounds with C-O-Si linkages see C07F7/18) · CPC title

• C07F7/0838

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C07F7/1892 Primary

  by reactions not provided for in C07F7/1876 - C07F7/1888 · CPC title