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-9409930-B2
Application number	US-201314395750-A
Country	US
Kind code	B2
Filing date	Feb 25, 2013
Priority date	Apr 20, 2012
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

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 process for preparing a composition comprising an acrylamido-functional siloxanol, the process comprising reacting, at least partially in the presence of water, as a component A, an aminoalkyl-functional silicon compound selected from the group consisting of
(i) at least one aminoalkyl-functional alkoxysilane or a mixture of aminoalkyl-functional alkoxysilanes of formula (I):
(R 1 O) 3-a-b (R 2 ) a Si(B) 1+b   (I),

(ii) a hydrolysis or condensation product of the at least one aminoalkyl-functional alkoxysilane of formula (I), and
(iii) a mixture comprising the at least one aminoalkyl-functional alkoxysilane of the formula (I) and a hydrolysis product, condensation product, or both, of the at least one aminoalkyl-functional alkoxysilane of the formula (I),

with an acrylic anhydride of the formula IV:
(CHR 5 ═CR 4 CO) 2 O  (IV),

and optionally at least partly removing hydrolyzed alcohol formed in the reaction,
wherein:
B in formula (I) 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), or

B in formula (I) represents a group of formula (III):
—(CH 2 ) j —NH 2-p (CH 2 —CH 2 —NH 2 ) p   (III);

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

2. The process according to claim 1 , wherein the aminoalkyl-functional alkoxysilane of the formula (I) is defined such that:
a) R 1 is independently methyl or ethyl, a=0, b=0, c=1, 2 or 3, B represents the group of formula (II), g=0, e=1, and h=0, d=1, 2, 3;
b) R 1 is independently methyl or ethyl, and with a=0, b=0, c=3, B represents the group of formula (II), and g, e and h are each 0, or, in an alternative, with a=0, b=0, c=3, B represents the group of formula (II), e=1, d=1, 2, 3, g=0, and h=0, or with B representing the group of formula II, e=g=0 or 1, d=f=2 or 3, h=0, and c=3, or with B representing the group of formula III, j=3 and p=1 or 2;
c) R 1 is independently methyl or ethyl, and with a=0, b=0, c=2, B represents the group of formula (II), and g, e and h are each 0, or, in an alternative, with a=0, b=0, c=3, B represents the group of formula (II), e=1, d=1, 2, 3, g=0, and h=0, or with B representing the group of formula (II), e=g=0 or 1, d=f=2 or 3, h=0, and c=2, or with B representing the group of formula (III), j=3 and p=1 or 2; or
d) R 1 is independently methyl or ethyl, and with a=0, b=0, c=1, B representing the group of formula (II), g, e and h each 0, or, in an alternative, with a=0, b=0, c=3, B represents the group of formula (II), e=1, d=1, 2, 3, g=0, and h=0, or with B representing the group of formula (II), e=g=0 or 1, d=f=2 or 3, h=0, and c=1, or with B representing the group of the formula (III), j=3, and p=1 or 2.

3. The process according to claim 1 , wherein the aminoalkyl-functional silane of formula (I) is selected from the group consisting of 3-aminopropyl trimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyl dimethoxysilane, 3-aminopropylmethyldiethoxysilane, 1-aminomethyltrimethoxysilane, 1-aminomethyltriethoxy silane, 2-aminoethyltrimethoxysilane, 2-aminoethyltriethoxysilane, 3-aminoisobutyl trimethoxysilane, 3-aminoisobutyltriethoxysilane, N-n-butyl-3-aminopropyl triethoxysilane, N-n-butyl-3-aminopropylmethyldiethoxysilane, N-n-butyl-3-aminopropyl trimethoxysilane, N-n-butyl-3-aminopropylmethyldimethoxysilane, methyltriethoxysilane, N-n-butyl-1-aminomethylmethyldimethoxysilane, N-n-butyl-1-amino methyltrimethoxysilane, N-n-butyl-1-aminomethylmethyltriethoxysilane, benzyl-3-amino propyltrimethoxysilane, benzyl-3-aminopropyltriethoxysilane, benzyl-2-aminoethyl-3-amino propyltrimethoxysilane, benzyl-2-aminoethyl-3-aminopropyltriethoxysilane, diaminoethylene-3-propyltrimethoxysilane, diaminoethylene-3-propyltriethoxysilane, triaminodiethylene-3-propyltrimethoxysilane, triaminodiethylene-3-propyltriethoxysilane, (2-aminoethylamino)ethyltrimethoxysilane, (2-aminoethylamino)ethyltriethoxysilane, (1-aminoethylamino)methyltrimethoxysilane and (1-aminoethylamino)methyltriethoxysilane.

4. The process according to claim 1 , wherein the acrylic anhydride of formula (IV) is methacrylic anhydride or (unsubstituted) acrylic anhydride.

5. The process according to claim 1 , wherein from 0.1 to 4.5 mol of the water per mole of silicon atoms in the aminoalkyl-functional silicon compound is added in the process.

6. The process according to claim 1 , wherein an amount of the water added to the reaction is established prior to the reaction with the acrylic anhydride.

7. The process according to claim 1 , comprising:
admixing the component A, optionally in a mixture with a diluent, with the water;
optionally at least partly removing the hydrolized alcohol, the diluent, or both, from a reaction mixture;
adding the acrylic anhydride of the formula (IV) to a resulting mixture; and
optionally adding a stabilizer to the resulting mixture,
wherein
after the admixing, the removal of the hydrolized alcohol, the added diluent, or both, optionally occurs under ambient or reduced pressure and elevated temperature,
after the admixing, a base is optionally added to the reaction mixture,
a precipitate is optionally removed from the reaction mixture, and
an organic acid is optionally added to the reaction mixture.

8. The process according claim 1 , wherein a molar ratio of nitrogen atoms in the aminoalkyl-functional silicon compound to acryloylcarbonyl function released from the acrylic anhydride of the formula (IV) is from 1:5 to 5:1 with a range of variation of plus/minus 0.5.

9. The process according to claim 1 , further comprising adjusting an active ingredient content of the acrylamido-functional siloxanol in the composition to 0.0001 to 99.9% by weight.

10. The process according to claim 1 , wherein a pH of the composition is between 5 and 11.

11. The process according to claim 1 , wherein a volatile diluent and the hydrolyzed alcohol are removed down to a content in the overall composition of less than or equal to 12% by weight to 0% by weight.

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

• C07F7/0838

  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

• C07F7/18 Primary

  Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages · CPC title

• C07F7/10

  containing nitrogen {having a Si-N linkage} · CPC title