Curable compositions containing silyl groups, and use thereof

Patent metadata

Field	Value
Publication number	US-8974627-B2
Application number	US-201013322468-A
Country	US
Kind code	B2
Filing date	Apr 26, 2010
Priority date	May 25, 2009
Publication date	Mar 10, 2015
Grant date	Mar 10, 2015

Abstract

This invention relates to curable compositions containing hydroxyl compounds that carry silyl groups as well as to the use of said compositions.

First claim

The invention claimed is:

1. A curable composition comprising:
a hydroxyl compound which bears silyl groups; and
at least one further silane compound;
wherein the hydroxyl compound is of the formula 1:

where:
a is an integer from 1 to 3;
b is an integer from 0 to 2;
the sum of a and b is equal to 3;

where:
c is an integer from 0 to 22;
d is an integer from 1 to 1,000;
e is an integer from 0 to 10,000;
f is an integer from 0 to 1,000;
g is an integer from 0 to 1,000;
h, i, and j are each integers from 0 to 500; and
n is an integer from 2 to 8;
with the proviso that the fragments with the indices d to j are freely permutable with one another; and

where:
R represents one or more identical or different, linear or branched, saturated or monounsaturated or polyunsaturated, alkyl or haloalkyl radicals having 1 to 20 carbon atoms;
R 1 is:
a saturated or unsaturated, optionally branched radical attached via an oxygen atom; or
a polyether radical of the alkoxy, arylalkoxy or alkylarylalkoxy group type, in which the carbon chain is optionally interrupted by oxygen atoms; or
a polyetheralkoxy radical; or
an optionally singly or multiply fused aromatic aryloxy group;

R 2 and R 3 are each independently:
H; or
a saturated or monounsaturated or polyunsaturated, optionally-substituted, monovalent or polyvalent hydrocarbon radical, it being the case that, when the R 2 and R 3 radicals are each a polyvalent hydrocarbon radical, the R 2 and R 3 radicals are cycloaliphatically bridged via the Y fragment, where:
 Y is absent, or is a methylene bridge having 1 or 2 methylene units;
 wherein, if Y is absent, R 2 and R 3 are each independently a linear or branched radical having 1 to 20 carbon atoms;

R 4 is:
a linear or branched alkyl radical of 1 to 24 carbon atoms; or
an aromatic or cycloaliphatic radical which optionally bears at least one alkyl group;

R 5 and R 6 are each independently:
H; or
a saturated or monounsaturated or polyunsaturated, optionally-substituted, hydrocarbon radical; or
a linear or branched radical having 1 to 20 carbon atoms;

R 7 and R 8 are each independently
hydrogen; or
an alkyl, alkoxy, aryl, or aralkyl group which is copolymerized with ring-opening polymerization to give a crosslinkable polyether ester containing alkoxysilane groups;

R 9 and R 10 are each independently
hydrogen; or
an alkyl, alkenyl, alkoxy, aryl, or aralkyl group; and

R 11 and R 12 are each independently;
hydrogen; or
an alkyl, alkenyl, alkoxy, aryl, or aralkyl group;
where the hydrocarbon radical R 11 and R 12 radicals are optionally bridged cycloaliphatically or aromatically via the Z fragment; and
where, if present, Z is a divalent alkylene or alkenylene radical.

2. The composition as claimed in claim 1 ;
wherein the further silane compound used is an alkoxysilyl-functional prepolymer, an alkoxysilyl-terminated polyether, an alkoxysilyl-terminated polyester, an alkoxysilyl-terminated polyether ester, an alkoxysilyl-terminated polyurethane, a polysiloxane or polyether siloxane having alkoxysilyl groups, or mixtures thereof.

3. The composition as claimed in claim 1 ;
wherein R 1 is a silicon-containing radical or a siloxane radical which is optionally substituted by alkyl and/or aryl groups.

4. The composition as claimed in claim 1 ;
wherein the further silane compound is a silane-modified polymer of the formula (2):

where:
X 1 , X 2 , and X 3 are each independently alkyl or alkoxy radicals having 1-8 carbon atoms;
A is:
a radical containing a carboxyl, carbamate, amide, carbonate, ureido, or sulfonate group; or
an oxygen atom;

w is an integer from 1 to 8;
v is an integer from 1 to 20; and
polymer is a polymer radical selected from a group consisting of alkyd resins, oil-modified alkyd resins, saturated polyesters, unsaturated polyesters, natural oils, epoxides, polyamides, polycarbonates, polyethylenes, polypropylenes, polybutylenes, polystyrenes, ethylene-propylene copolymers, (meth)acrylates, (meth)acrylamides and salts thereof, phenol resins, polyoxymethylene homopolymers, polyoxymethylene copolymers, polyurethanes, polysulfones, polysulfide rubbers, nitrocelluloses, vinyl butyrates, vinyl polymers, ethylcelluloses, cellulose acetates, cellulose butyrates, rayon, shellac, waxes, ethylene copolymers, organic rubbers, polysiloxanes, polyether siloxanes, silicone resins, polyethers, polyether esters, and polyether carbonates.

5. The composition as claimed in claim 4 ;
wherein v is 1, so that the alkoxysilyl-functional prepolymers of the formula (2) are α-silane-terminated polymers whose reactive alkoxysilyl groups are separated only by one methylene unit (v=1) from a nitrogen-containing polymer-bound A group.

6. The composition as claimed in claim 1 ;
wherein the hydroxyl compound of the formula 1 is mixed with dimethoxy(methyl)silylmethyl carbamate-terminated polyethers and/or trimethoxysilylmethyl carbamate-terminated polyethers.

7. The composition as claimed in claim 4 ;
wherein:
v=3; and
A is a urethane group or is a radical bearing urea groups.

8. The composition as claimed in claim 7 ;
wherein the silane polymer of the formula (2) is dimethoxy(methyl)silylpropyl carbamate- and/or trimethoxysilylpropyl carbamate-terminated polyether.

9. The composition as claimed in claim 4 ;
wherein the silane polymer of the formula (2) is a urethane-free and urea-free silyl-terminated polyether; and
where wherein A is oxygen.

10. The composition as claimed in claim 1 ,
wherein the further silane compound is a monomeric silane of the formula (2a):
W x SiV (4-x)   (2a);

where:
W represents identical or different nonhydrolyzable groups, which are optionally substituted by one or more substituents and which are selected from the group consisting of:
alkyl, alkenyl, alkynyl, aryl, alkylaryl, and aralkyl radicals, where the alkyl chain optionally has 0 to 50 carbon atoms and optionally is interrupted by at least one heteroatom;

V represents identical or different hydrolyzable groups or hydroxyl groups, which are optionally substituted by one or more substituents, and which are selected from the group consisting of:
hydrogen and halogen; and
alkoxy, aryloxy, acyloxy, acyl, amino, monoalkylamino, and dialkylamino groups; and

x is 1, 2, 3, or 4.

11. The composition as claimed in claim 10 ;
wherein the nonhydrolyzable W radical, in at least one case, is a selected from the group consisting of glycidyl, glycidyloxyalkylene, β-glycidyloxyethyl, γ-glycidyloxypropyl, δ-glycidyloxypropyl, ε-glycidyloxypentyl, ω-glycidyloxyhexyl, 2-(3,4-epoxycyclohexyl)ethyl, methacryloyloxyalkylene, acryloyloxyalkylene, methacryloyloxymethyl, acryloyloxymethyl, methacryloyloxyethyl, acryloyloxyethyl, methacryloyloxypropyl, acryloyloxypropyl, methacryloyloxybutyl, acryloyloxybutyl, and 3-isocyanatopropyl radicals.

12. The composition as claimed in claim 10 ,
the monomeric silane of the formula (2a) is at least one compound selected from the group consisting of
N-cyclohexylaminomethyltrimethoxysilane, N-cyclohexyl-3-aminopropyltriethoxysilane, 3-aminopropyltrimethaxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyldimethoxymethylsilane, 3-isocyanato-propyltrimethoxysilane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-methacryloyloxypropyltrimethoxysilane,

Assignees

• Schubert Frank
• Knott Wilfried
• Evonik Degussa Gmbh

Inventors

• Schubert Frank
• Knott Wilfried

Classifications

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title

• C09D183/06

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title

• C09J183/06

  containing silicon bound to oxygen-containing groups (C09J183/12 takes precedence) · CPC title

• C08B15/05

  Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur (esters or phosphorous acids C08B5/00) · CPC title

• C09D183/04

  Polysiloxanes · CPC title