IP Library › Granted Patent US 8,907,014
Granted Patent B2
US 8,907,014 · App. 14/113,318 · Granted Dec 9, 2014

Silane terminated polymer for coating, adhesives, sealant and elastomer applications

Inventors: Kamesh R. Vyakaranam (Pearland, TX); William A. Koonce (Pearland, TX); Ling Zhang (Missouri City, TX); Jean-Luc Roser (Thalwil, CH)
Assignee: Dow Global Technologies LLC
C08G81/025C08G18/10C08G18/289C08G18/632C08G18/718C08G18/7621
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Quick Facts
Patent No.
US 8,907,014
App. No.
14/113,318
Granted
Dec 9, 2014
Kind
B2
Abstract

A copolymer-filled crosslinkable silane-terminated polymer having at least one crosslinkable silyl group in each molecule is provided. The copolymer-filled crosslinkable silane-terminated polymer is the reaction product of a copolymer-filled polyol and an isocyanate capped hydrosilylated polymer. The isocyanate capped hydrosilylated polymer is the reaction product of at least one isocyanate and a hydrosilylated polymer. The hydrosilylated polymer is the reaction product of a polymer having at least one unsaturated group and at least one alcoholic group in each molecule and a compound having a hydrogen-silicon bond and a crosslinkable silyl group in each molecule. The copolymer-filled crosslinkable silane-terminated polymers exhibit improved modulus and tensile strength properties while maintaining elongation properties.

Claims (33)

1. A composition comprising:

a copolymer-filled crosslinkable silane-terminated polymer having at least one crosslinkable silyl group in each molecule, wherein the copolymer-filled crosslinkable silane-terminated polymer is the reaction product of:

a copolymer-filled polyol; and

an isocyanate capped hydrosilylated polymer comprising the reaction product of:

at least one isocyanate; and

a hydrosilylated polymer comprising the reaction product of:

a polymer having at least one unsaturated group and at least one alcoholic group in each molecule; and

a compound having a hydrogen-silicon bond and a crosslinkable silyl group in each molecule.

2. The composition of claim 1 , wherein the hydrosilylated polymer is reacted with the isocyanate at an isocyanate index of between about 100 and about 250.

3. The composition of claim 1 , wherein the hydrosilylated polymer is a reaction product of a hydrosilylation efficiency of at least about 70% as determined by 1H-NMR.

4. The composition claim 1 , wherein the polymer having at least one unsaturated group and at least one alcoholic hydroxyl group in each molecule has a number average molecular weight of between about 100 and about 5,000.

5. The composition claim 1 , wherein the polymer having at least one unsaturated group and at least one alcoholic hydroxyl group in each molecule is a propylene glycol monoallyl ether having a number average molecular weight between 600 and 1,000 and an OH number between 50 and 90.

6. The composition of claim 1 , wherein the copolymer-filled polyol comprises:

a polyether polyol matrix; and

a solid copolymer phase.

7. The composition of claim 6 , wherein the polyether polyol matrix is derived from ethylene oxide, propylene oxide, butylene oxide, tetramethylene oxide, and combinations thereof.

8. The composition of claim 6 , wherein the solid copolymer phase is at least one of copolymerized styrene and acrylonitrile, styrene-acrylonitrile, acrylonitrile, polyurea (PHD) polymer solids, and polyurethane-urea particles (PIPA).

9. An article comprising the crosslinkable silane-terminated polymer of claim 1 .

10. A method of producing a composition comprising a copolymer-filled crosslinkable silane-terminated polymer having at least one crosslinkable silyl group in each molecule, the method comprising:

providing a polymer having at least one unsaturated group and at least one alcoholic hydroxyl group in each molecule and having a number average molecular weight of between about 100 and about 5,000;

adding to the polymer a compound having a hydrogen-silicon bond and a crosslinkable silyl group in each molecule and a hydrosilylation catalyst to thereby carry out a hydrosilylation reaction to form a composition comprising hydrosilylated polymer;

capping the hydrosilylated polymer by exposing the hydrosilylated polymer to at least one isocyanate at an isocyanate index of between about 100 and about 250 to form a composition comprising isocyanate capped hydrosilylated polymers; and

reacting the isocyanate capped hydrosilylated polymer with a copolymer-filled polyol to form the composition comprising a crosslinkable silane-terminated polymer.

11. The method of claim 10 , wherein the hydrosilylation reaction has a hydrosilylation efficiency of at least about 70% as determined by 1 H-NMR.

12. The method of claim 10 , wherein the polymer having at least one unsaturated group and at least one alcoholic hydroxyl group in each molecule has a number average molecular weight of between about 800 and about 2,000 g/mol.

13. The method of claim 10 , wherein the polymer having at least one unsaturated group and at least one alcoholic hydroxyl group in each molecule comprises a propylene glycol monoallyl ether having a number average molecular weight between about 600 and about 1,000, and an OH number of between about 50 and about 90.

14. The method of claim 10 , wherein the isocyanate index is between about 160 and about 200.

15. The method of claim 11 , wherein the hydrosilylation efficiency is at least about 85%.

16. The method of claim 10 , wherein the compound having a hydrogen-silicon bond and a crosslinkable silyl group comprises at least one of trimethoxysilane, triethoxysilane, methyldiethoxysilane, methyldimethoxysilane, phenyldimethoxysilane, trimethylsiloxymethylmethoxysilane and trimethylsiloxydiethoxysilane.

17. The method of claim 10 , wherein the isocyanate comprises at least one of 4,4′-, 2 , 4 ′ and 2,2′-isomers of diphenylmethane diisocyante, 2,4-toluene diisocyanate and 20% 2,6-toluene diisocyanate, or blends thereof.

18. The method of claim 10 , wherein the crosslinkable silane-terminated polymer is cured with an amine containing catalyst to form a cured polymer.

19. The method of claim 10 , wherein the capping the hydrosilylated polymer is a catalyst-free reaction.

20. The method of claim 10 , wherein the composition comprising the crosslinkable silane-terminated polymer is cured with a tin catalyst.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2014
From: ROSER, JEAN-LUC
To: DOW EUROPE GMBH
Reel/Frame 034120/0173 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2014
From: DOW EUROPE GMBH
To: THE DOW CHEMICAL COMPANY
Reel/Frame 034120/0252 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2014
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES LLC.
Reel/Frame 034120/0392 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2014
From: VYAKARANAM, KAMESH R; KOONCE, WILLIAM A; ZHANG, LING
To: DOW GLOBAL TECHNOLOGIES LLC.
Reel/Frame 034120/0490 →
Continuity (1)
Related Publication 20140309372A1 · Oct 16, 2014