Silane modified polymers and use of the same in adhesive compositions

Patent metadata

Field	Value
Publication number	US-11021565-B2
Application number	US-202015929486-A
Country	US
Kind code	B2
Filing date	May 5, 2020
Priority date	Nov 7, 2017
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

Disclosed is a moisture curable silane modified terpolymer comprising a polyether segment, a segment of polytetrahydrofuran or polycarbonate, a polysiloxane segment and terminal amino silane groups joined to the terpolymer via urethane linkages and wherein the polyether segment comprises at least 70% by weight based on the total weight of the silane modified terpolymer. Also disclosed is a method of forming moisture curable silane modified terpolymer.

First claim

We claim:

1. A moisture curable, silane modified terpolymer comprising:
at least one polyether segment; at least one segment selected from polytetrahydrofuran or polycarbonate; and at least one polysiloxane segment, each of the segments covalently bonded to an adjacent segment by a urethane linkage; and
at least one terminal silyl hydrolysable group connected to the polymer via a linking group derived from an isocyanate containing compound, wherein each terminal silyl hydrolysable group comprises one to three hydrolysable groups.

2. A silane modified terpolymer as recited in claim 1 wherein the polyether segment comprises at least 70% by weight based on the total weight of the silane modified polymer.

3. A silane modified terpolymer as recited in claim 1 wherein said polyether segment has a molecular weight of from 1000 to 30000.

4. A silane modified terpolymer as recited in claim 1 wherein said polyether segment is formed from ethylene oxide, propylene oxide, butylene oxide, an epichlorohydrin residue or a mixture thereof.

5. A silane modified terpolymer as recited in claim 1 wherein the polytetrahydrofuran segment has a molecular weight of 2000 daltons or less and the polycarbonate segment has a MW of 2000 dalton or less.

6. A silane modified terpolymer as recited in claim 1 wherein said polysiloxane segment has a molecular weight of 20,000 daltons or less.

7. A silane modified terpolymer as recited in claim 1 wherein said polysiloxane segment has a general formula of:
—(CH 2 ) m —Si(CH 3 ) 2 —O—[Si(CH 3 ) 2 —O] n —Si(CH 3 ) 2 —(CH 2 ) m —

wherein “m” has a value of from 0 to 30 and “n” has a value of from 30 to 50, such that the overall weight of the polysiloxane segment has a value of 5,000 daltons or less.

8. A silane modified terpolymer as recited in claim 1 comprising a segment including polycarbonate and no polytetrahydrofuran.

9. A silane modified terpolymer as recited in claim 1 wherein said urethane linkages are derived from 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI).

10. A silane modified terpolymer as recited in claim 1 wherein said terminal silyl hydrolysable groups have the general formula of:
—N(R 2 ) a (R 1 —SiXYZ) 2-a

wherein:
a is 0 or 1;
R 1 is a divalent hydrocarbyl group having 1 to 12 carbon atoms and linking the N and Si atom;
X, Y, Z are, independently of one another, selected from the group consisting of a hydroxyl, a C 1 to C 12 alkyl, or a C 1 to C 12 alkoxy and at least one of X, Y or Z is the alkoxy group; and
R 2 is hydrogen or a hydrocarbon residue having 1 to 12 carbon atoms.

11. A silane modified terpolymer as recited in claim 1 wherein the hydrolysable groups are alkoxy groups.

12. A silane modified terpolymer as recited in claim 1 wherein the hydrolysable groups may be the same or different.

13. Cured reaction products of the silane modified terpolymer of claim 1 .

14. A silane modified terpolymer comprising:
the reaction products of an intermediate terpolymer terminated with isocyanate groups and an amino silane;
wherein said intermediate terpolymer terminated with isocyanate groups comprises the reaction products of a mixture including polyether polyol; a polytetrahydrofuran having a molecular weight of 2000 daltons or less or a polycarbonate polyol having a molecular weight of 3000 daltons or less, a hydroxyl terminated polysiloxane or a carbinol siloxane having a molecular weight of 20,000 daltons or less, and an excess of diisocyanate.

15. The silane modified terpolymer of claim 14 ; comprising at least 70% by weight of polyether segments; from 0.1% to less than 20% by weight of polytetrahydrofuran or polycarbonate segments; and from 0.1% to less than 20% by weight of polysiloxane segments; by weight of the terpolymer.

16. A silane modified terpolymer as recited in claim 14 wherein said hydroxyl terminated polysiloxane has a general formula of:
HO—(CH 2 ) m —Si(CH 3 ) 2 —O—[Si(CH 3 ) 2 —O] n —Si(CH 3 ) 2 —(CH 2 ) m —OH

wherein “m” has a value of from 0 to 30 and “n” has a value of from 30 to 50, such that the overall weight of the polysiloxane segment has a value of 5,000 daltons or less.

17. An adhesive composition comprising the silane modified terpolymer of claim 14 .

18. Cured reaction products of the silane modified terpolymer of claim 14 .

19. A method of forming a silane modified terpolymer comprising:
providing a mixture comprising at least 70% by weight polyether polyol, about 0.1% to 20% by weight of polytetrahydrofuran polyol or a polycarbonate polyol, and about 0.1% to 20% by weight of a hydroxyl terminated polysiloxane or a carbinol polysiloxane;
reacting the mixture with an excess of equivalents of a diisocyanate to form an isocyanate functional terpolymer intermediate; and
reacting the isocyanate functional terpolymer intermediate with an amino silane to form the silane modified terpolymer, wherein the polyether polyol comprises at least 70% by weight based on the total weight of the silane modified terpolymer.

20. The method of forming a silane modified terpolymer as recited in claim 19 wherein the polyisocyanate is selected from the group consisting of 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), toluylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI) and combinations thereof.

Assignees

• Henkel IP & Holding GmbH
• Henkel Ag & Co Kgaa

Inventors

• Suen Wu
• Eodice Andrea Keys
• Meckel-Jonas Claudia
• Despotopoulou Christina
• Klein Johann

Classifications

• C08G18/755 Primary

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/61 Primary

  Polysiloxanes · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C09J175/08

  from polyethers · CPC title

• C08G18/44

  Polycarbonates · CPC title