Silane-containing isocyanate-terminated polyurethane polymers

• US 4,374,237 A
• Filed: 12/21/1981
• Issued: 02/15/1983
• Est. Priority Date: 12/21/1981
• Status: Expired due to Term

• Current Assignee: Witco Corporation (Lanxess AG)
• Original Assignee: Union Carbide Corporation (Dow, Inc.)
• Inventors: Berger, Mitchell H., Mayer, Walter P., Ward, Robert J.
• Primary Examiner(s): Cockeram, H. S.
• Application Number:
  US06/333,103
• Time in Patent Office: 421 Days
• Field of Search: 528/28, 528/38, 528/59
• US Class Current: 528/28
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/289 containing silicon
• CPC Class Codes: C08G 18/3893 containing silicon
• CPC Class Codes: C08G 2190/00 Compositions for sealing or packing joints
• CPC Class Codes: C09K 3/1021 Polyurethanes or derivatives thereof

Abstract

Curable isocyanate prepolymers have been made in which all or a portion of the available isocyanate terminal groups have been reacted with a secondary amine-containing silane monomer having two trialkoxy silane groups.

Claims

1. A curable composition comprising the reaction product of an isocyanate terminated polyurethane prepolymer having at least two urethane linkages per polymer molecule and a bis silane, said reaction product having a number average molecular weight of about 750 to about 20,000 and having 2 to about 9 functional groups, per average molecular weight, selected from the group consisting of:

##STR10## wherein R is a lower alkyl having 1 to about 6 carbons;

R¹ is a lower alkyl having 1 to about 4 carbons;

each of R² and R³ is an alkylene radical having 2 to 18 carbons or arylene radicals having 6 to 18 carbons, and

a is an integer having values of 0 to 2;

##STR11## wherein R, R¹ and a are as above,

each of R⁴ and R⁵ is an alkylene radical having 1 to 4 carbons, and

Q is a monovalent radical selected from the group consisting of hydrogen, alkyl having 1 to 4 carbons, phenyl, --COOR¹ or --CN; and

##STR12## wherein R, R¹ and a are as above,

each of R⁷ and R⁸ is an alkylene radical having 1 to 4 carbons, and

Q is a monovalent radical selected from the group consisting of hydrogen, alkyl having 1 to 4 carbons, phenyl, COOR¹ or --CN,

with the proviso that at least 0.1 percent of the total of said functional groups (1), (2), (3) and (4) is at least one of (2), (3), or (4).

2. Composition claimed in claim 1 containing about 0.1 to about 100 percent of functional group (2).

3. Composition claimed in claim 1 containing about 0.1 to about 100 percent of functional group (3).

4. Composition claimed in claim 1 containing about 0.1 to about 100 percent of functional group (4).

5. Composition claimed in claim 2 wherein the functional group (2) is:

##STR13##

6. Composition claimed in claim 3 wherein the functional group (3) is:

##STR14##

7. Composition claimed in claim 4 wherein the functional group (4) is:

##STR15##

8. Composition claimed in claim 1 wherein the polyurethane is the reaction product of polyoxyalkylene polyol and an aromatic diisocyanate.

9. Composition claimed in claim 8 wherein the polyoxyalkylene polyol is a polyoxyalkylene glycol and the aromatic diisocyanate is toluene diisocyanate.

10. Composition claimed in claim 1 wherein the polyurethane is the reaction product of a polyoxyalkylene diol, a polyoxyalkylene triol and an aromatic polyisocyanate.

11. Composition claimed in claim 10 wherein the polyoxyalkylene diol is a polyoxypropylene glycol, the polyoxyalkylene triol is a polyoxypropylene triol and the aromatic polyisocyanate is toluene diisocyanate.

12. The cured polymer of claim 1.

13. The cured polymer of claim 2.

14. The cured polymer of claim 3.

15. The cured polymer of claim 4.

16. The cured polymer of claim 5.

17. The cured polymer of claim 6.

18. The cured polymer of claim 7.

19. A sealant composition comprising the curable composition claimed in claim 1.

20. A method of formulating a sealant composition having enhanced wet adhesion which comprises:

(1) reacting a polyol with a stoichiometric excess of a polyisocyanate to provide an --NCO terminated polyurethane prepolymer; and

(2) end-capping at least 0.1% of said --NCO terminal groups by contacting them with a bis-silane selected from the group consisting of;

##STR16## wherein R is a lower alkyl having 1 to about 6 carbons;

R¹ is a lower alkyl having 1 to about 4 carbons,

each of R² and R³ is an alkylene radical having 2 to 18 carbons or arylene radicals having 6 to 18 carbons, and

a is an integer having values of 0 to 2;

##STR17## wherein R, R¹ and a are as above,

each of R⁴ and R⁵ is an alkylene radical having 1 to 4 carbons, and

Q is a monovalent radical selected from the group consisting of hydrogen, alkyl having 1 to 4 carbons, phenyl, --COOR¹ or --CN; and

##STR18## wherein R, R¹ and a are as above,

each of R⁷ and R⁸ is an alkylene radical having 1 to 4 carbons, and

Q is a monovalent radical selected from the group consisting of hydrogen, alkyl having 1 to 4 carbons, phenyl, COOR¹ or --CN.

21. Method claimed in claim 20 wherein the bis-silane is (A).

22. Method claimed in claim 20 wherein the bis-silane is (B).

23. Method claimed in claim 20 wherein the bis-silane is (C).