Curable compositions containing isocyanate functional components having improved durability

Patent metadata

Field	Value
Publication number	US-9290607-B2
Application number	US-201113885279-A
Country	US
Kind code	B2
Filing date	Nov 23, 2011
Priority date	Dec 20, 2010
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

A composition comprising: a) one or more isocyanate functional prepolymers; b) one or more catalysts for the reaction of isocyanate moieties with hydroxyl groups; c) one or more reinforcing fillers; and d) a stabilizing amount of one or more compounds comprising a dihydrocarbyl hydroxylamine, an alicyclic hydroxylamine, a nitrile oxide of a dihydrocarbyl hydroxylamine or a nitrile oxide of an alicyclic hydroxylamine. In another embodiment the invention is a method of bonding two or more substrates together which comprises contacting the two or more substrates together with a composition according to this invention disposed along at least a portion of the area wherein the substrates are in contact. The compositions of the invention are useful as an adhesive to bond substrates together.

First claim

What is claimed is:

1. A composition comprising
a) about 40 to about 70 percent by weight of one or more isocyanate functional prepolymers having an isocyanate content of about 0.5 to about 5.0 percent by weight based on the weight of the isocyanate functional prepolymers;
b) about 0.01 to about 2 percent by weight of one or more catalysts for the reaction of isocyanate moieties with active hydrogen atom containing;
c) one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitroxyl of a dihydrocarbyl hydroxyl amine wherein the nitroxyl is a group having the structure —NO. or a nitroxyl of an alicyclic hydroxyl amine wherein the nitroxyl is a group having the structure —NO. present in an amount of about 0.1 to about 0.5 percent by weight;
d) about 5 to about 35 percent by weight of one or more fillers; and
e) about 5 to about 40 percent by weight of one or more plasticizers;
wherein the amounts are based on the weight of the composition and the composition forms a polymeric matrix that is cured.

2. A composition according to claim 1 wherein the filler is a reinforcing filler.

3. A composition according to claim 2 wherein the reinforcing filler is carbon black.

4. A composition according to claim 2 wherein the carbon black is a high surface area carbon black which exhibits an iodine number of 130 mg/g or greater.

5. A composition according to claim 1 wherein the plasticizer is a branched plasticizer.

6. A composition according to claim 1 wherein the hydroxyl amines correspond to the formula (R 1 ) 2 N—OH and the nitroxyls of hydroxyl amines correspond to the formula (R 1 ) 2 —N—O. wherein R 1 is independently in each occurrence a hydrocarbyl moiety or two R 1 form a cyclic ring and the hydrocarbyl moieties may be substituted with a substituent which does not interfere in stabilizing the composition, wherein the substituent is hydroxyl, alkyl groups, ethers, tertiary amines or sulfides.

7. A composition according to claim 6 wherein the stabilizer is nitroxyl of a hydroxyl amine wherein the nitroxyl is a group having the structure —NO.

8. A composition according to claim 7 wherein the stabilizer is a nitroxyl of 4-hydroxy-2,2,6,6-tetramethyl piperdinyl oxide wherein the nitroxyl is a group having the structure —NO.

9. A composition according to claim 1 wherein the composition is a one part curable composition.

10. A composition according to claim 9 wherein the composition is substantially free of alkoxy silane groups.

11. A composition comprising
a) about 40 to about 70 percent by weight of one or more isocyanate functional prepolymers having an isocyanate content of about 6 to 35 percent by weight based on the weight of the isocyanate prepolymers;
b) one or more catalysts for the reaction of isocyanate moieties with active hydrogen atom containing groups present in an amount of about 0.01 to about 2 percent by weight;
c) one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitroxyl of a dihydrocarbyl hydroxyl amine wherein the nitroxyl is a group having the structure —NO. or a nitroxyl of an alicyclic hydroxyl amine wherein the nitroxyl is a group having the structure —NO. present in an amount of about 0.1 to about 0.5 percent by weight based on the weight of the composition;
d) about 5 to about 35 percent by weight of one or more fillers; and
e) about 5 to about 40 percent by weight one or more plasticizers;
wherein the amounts are based on the weight of the composition and the composition is a two part composition wherein part 1 comprises one or more isocyanate functional components; part 2 comprises one or more catalysts for the reaction of isocyanate moieties with active hydrogen atom containing groups and one or more components containing more than one active hydrogen containing groups; and the one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitroxyl of a dihydrocarbyl hydroxyl amine wherein the nitroxyl is a group having the structure —NO. or of a nitoxyl of an alicyclic hydroxyl amine, wherein the nitroxyl is a group having the structure —NO., may be present in part 1, part 2 or both.

12. A method of bonding two or more substrates together which comprises contacting the two or more substrates together with a composition according to claim 1 disposed along at least a portion of the area wherein the substrates are in contact.

13. A method according to according to claim 12 wherein at least one of the substrates is window glass and at least one of the other substrates is a building or a vehicle.

14. A method according to claim 13 wherein the composition is a two part composition and the parts are contacted together prior to contacting the composition with one or more of the substrates.

15. A composition according to claim 1 wherein the one or more isocyanate functional prepolymers are the reaction product of a mixture of one or more polyether diols and one or more polyether triols.

16. A composition according to claim 1 wherein the composition includes a polyfunctional isocyanate.

Assignees

• Jialanella Gary L
• Ristoski Toni
• Frishcosy Mike
• Dow Global Technologies Llc

Inventors

• Jialanella Gary L
• Ristoski Toni
• Frishcosy Mike

Classifications

• C08K5/005

  Stabilisers against oxidation, heat, light, ozone · CPC title

• C09J175/02

  Polyureas · CPC title

• E06B3/56

  by means of putty, cement, or adhesives only (E06B3/64 {E06B3/5427} take precedence) · CPC title

• B32B37/00

  Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding · CPC title

• C09J175/04

  Polyurethanes · CPC title