Urethane-containing silylated prepolymers and process for preparation thereof

Patent metadata

Field	Value
Publication number	US-9315614-B2
Application number	US-85973110-A
Country	US
Kind code	B2
Filing date	Aug 19, 2010
Priority date	Aug 19, 2009
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

Novel urethane- and silyl-containing prepolymers and compositions obtained as reaction products from alkoxysilyl-bearing compounds and isocyanate-bearing compounds, and a process for preparation thereof.

First claim

The invention claimed is:

1. Urethane-containing reaction products obtained by the reaction of:
(a) at least one compound having one or more isocyanate groups, and bearing no alkoxysilyl and/or alkylsilyl groups; with
(b) at least one compound bearing a plurality of alkoxysilyl groups and additionally bearing at least one hydroxyl group;
(c) optionally in the presence of at least one catalyst;
wherein the molecules of the reaction products have an average of more than one alkoxysilyl group per urethane group.

2. The reaction products according to claim 1 ;
wherein the component (b) utilized is a compound of formula 1:

where:
a is an integer from 1 to 3; and
b is an integer from 0 to 2;
with the proviso that a sum of a plus b is 3;

where:
c is an integer from 0 to 22;
d is an integer from 2 to 500;
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 independently integers from 0 to 500;
n is an integer from 2 to 8;
Y is absent;
R is independently one or more, identical or different, linear or branched, saturated, monounsaturated, or polyunsaturated, alkyl or haloalkyl radical having 1 to 20 carbon atoms;
R 1 is:
a hydroxyl group; or
a saturated or unsaturated, linear, branched, or cyclic, substituted or unsubstituted, organic oxygen-containing radical having 1 to 1500 carbon atoms, where the carbon atoms are optionally interrupted by at least one hetero atom selected from the group consisting of O, S, Si, and N; or
a radical comprising an aromatic oxygen-containing radical;

R 2 and R 3 are each independently:
H; or
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 alkyl groups;

R 5 and R 6 radicals are each:
H; or
a monovalent hydrocarbon radical;

R 7 and R 8 are each independently:
hydrogen; or
alkyl, alkoxy, aryl, or aralkyl groups; and

R 9 and R 12 are each independently:
hydrogen; or
an alkyl, alkenyl, alkoxy, aryl, or aralkyl group; and

R 10 and R 11 are each independently:
hydrogen; or
an alkyl, alkenyl, alkoxy, aryl, or aralkyl group;
where R 10 and R 11 are optionally bridged cycloaliphatically or aromatically via the Z fragment; and
where, if present, Z is a divalent alkylene or alkenylene radical;

wherein, optionally, at least two of the fragments with the indices d, e, f, and h are freely permutable with one another, are distributed randomly or successively in blocks, and hence are exchangeable for one another in the sequence within the polymer chain.

3. Reaction products according to claim 2 ;
wherein the compound of formula 1 is a silyl polyether where:
e is an integer from 2 to 10,000.

4. A copolymer obtained by the reaction of:
the reaction products according to claim 1 ; with
at least one further component (d) reactive towards the reaction products.

5. The copolymer according to claim 4 ;
wherein component (d) comprises at least one compound with a functional group with protic hydrogen, selected from the group consisting of alcohols, amines, thiols, organofluorine hydroxyl compounds, alkoxysilanes, water.

6. A composition comprising:
at least one reaction product according to claim 1 .

7. A composition comprising:
at least one urethane-containing reaction product according to claim 1 ; and
at least one additional compound selected from the group consisting of:
compounds with at least one isocyanate, hydroxyl, epoxy, and/or unsaturated C═C group; and
acrylates, methacrylates, vinyl compounds, allyl compounds, silanes, and silyl-functional compounds.

8. A composition comprising:
at least one urethane-containing reaction product according to claim 1 ; and
at least one additional compound;
wherein the at least one additional compound comprises a silane of the formula (4):
U x SiV (4-x)   (4);

where:
U represents identical or different groups not hydrolysable in the presence of water and catalytic amounts of Brønsted acid at temperatures up to 100° C.;
V represents identical or different groups hydrolysable in the presence of water and catalytic amounts of Brønsted acid at temperatures up to 100° C., or hydroxyl groups; and
X is 1, 2, or 3; and/or

wherein the at least one additional compound comprises a silyl-functional compound of the formula (5):

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 sulphonate group, or is an oxygen atom,
w is an integer from 1 to 8;
v is an integer from 1 to 20; and
“Polymer-” is selected from a group consisting of alkyd resins, oil-modified alkyd resins, saturated or unsaturated polyesters, natural oils, epoxides, polyamides, polycarbonates, polyethylenes, polypropylenes, polybutylenes, polystyrenes, ethylene-propylene copolymers, (meth)acrylates, (meth)acrylamides and salts thereof, phenol resins, polyoxymethylene homo- and copolymers, polyurethanes, polysulphones, polysulphide rubbers, nitrocelluloses, vinyl butyrates, vinyl polymers, ethylcelluloses, cellulose acetates, cellulose butyrates, rayon, shellac, waxes, ethylene copolymers, organic rubbers, polysiloxanes, polyethersiloxanes, silicone resins, polyethers, polyetheresters, and polyethercarbonates.

9. A process for preparing the reaction products according to claim 1 , comprising:
reacting component (b) with component (a), to obtain the reaction products.

10. The process according to claim 9 ;
wherein a molar excess of component (a), based on component (b), is utilized in the reaction.

11. The process according to claim 10 ;
wherein alkoxysilyl-modified allophanates are formed.

12. The process according to claim 9 ;
wherein a molar excess of component (b), based on component (a), is utilized in the reaction.

13. A process comprising:
reacting the reaction products according to claim 1 with at least one further reactive component to obtain copolymers.

14. The process according to claim 13 ;
wherein the at least one further reactive component is selected from the group consisting of alcohols, diols, polyols, thiols, amines, amino-functional polymers, aminoalkoxysilanes, alkoxysilanes, acrylated alcohols, organic alkoxylates, polyetherdiols, polyesterdiols, polytetrahydrofuran, silicone polyether copolymers, OH-functional polyether radicals, acid chlorides, and organofluorine compounds.

Assignees

• Schubert Frank
• Ferenz Michael
• Knott Wilfried
• Evonik Degussa Gmbh

Inventors

• Schubert Frank
• Ferenz Michael
• Knott Wilfried

Classifications

• C07F7/0818

  Chemistry & Metallurgy · mapped topic

• C07F7/025

  without C-silicon linkages · CPC title

• C08G18/227

  of antimony, bismuth or arsenic · CPC title

• C07F7/081

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

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title