IP Library Granted Patent US 11,021,565
Granted Patent B2
US 11,021,565 · App. 15/929,486 · Granted Jun 1, 2021

Silane modified polymers and use of the same in adhesive compositions

Inventors: Wu Suen (Pennington, NJ); Andrea Keys Eodice (Hillsborough, NJ); Claudia Meckel-Jonas (Duesseldorf, DE); Christina Despotopoulou (Minneapolis, MN); Johann Klein (Duesseldorf, DE)
Assignees: Henkel AG & Co. KGaA; Henkel IP & Holding GmbH
C08G18/61C08G18/12C08G18/44C08G18/4808C08G18/4845C08G18/4854C08G18/755C08G64/183C08G64/186C08G77/448C08G77/46C09J175/08
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Quick Facts
Patent No.
US 11,021,565
App. No.
15/929,486
Granted
Jun 1, 2021
Kind
B2
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.

Claims (37)

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.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059357/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2021
From: MECKEL-JONAS, CLAUDIA; KLEIN, JOHANN; DESPOTOPOULOU, CHRISTINA
To: HENKEL AG & CO. KGAA
Reel/Frame 055605/0081 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2021
From: SUEN, WU; EODICE, ANDREA KEYS
To: HENKEL IP & HOLDING GMBH
Reel/Frame 055370/0396 →