Curable compositions containing isocyanate functional components having improved durability

Patent metadata

Field	Value
Publication number	US-9403933-B2
Application number	US-201214353429-A
Country	US
Kind code	B2
Filing date	Jun 7, 2012
Priority date	Dec 20, 2010
Publication date	Aug 2, 2016
Grant date	Aug 2, 2016

Abstract

A composition comprising a) one or more isocyanate functional components, one or more oligomers or prepolymers containing isocyanate functional groups and alkoxysilane groups, or prepolymers having a flexible backbone and silane moieties capable of silanol condensation: b) one or more catalysts for the reaction of isocyanate moieties with active hydrogen atom containing groups or for silanol condensation; c) one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitrile oxide of a dihydrocarbyl hydroxyl amine or a nitrile oxide of an alicyclic hydroxyl amine in a sufficient amount to enhance the ultraviolet stability of the composition in a cured state; and d) a pigment that does not have reinforcing properties or the composition contains one of one or more oligomers or prepolymers containing isocyanate functional groups and alkoxysilane groups, or prepolymers having a flexible backbone and silane moieties capable of silanol condensation. The compositions are useful as adhesives and sealers.

First claim

What is claimed is:

1. A composition comprising
a) about 20 to about 70 percent by weight of one or more 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 prepolymers and one or more oligomers or prepolymers containing isocyanate functional groups and alkoxysilane groups;
b) about 0.1 to about 2 percent by weight of one or more catalysts for the reaction of isocyanate moieties with active hydrogen atom containing groups;
c) one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitroxyl of a dihydrocarbyl hydroxyl amine or a nitroxyl of an alicyclic hydroxyl amine in an amount of about 0.01 to about 2.0 percent by weight; and
d) about 0.01 to about 25 percent by weight of a pigment selected from zinc oxide, cerium oxide, titanium dioxide, phthalocyanines, anthraquinones, perylenes, carbazoles, monoazo- and disazobenzimidazolones, isoindolinones, monoazonaphthols, di-arylidepyrazolones, rhodamines, indigoids, quinacridones, diazo-pyranthrones, dinitranilines, pyrazolones, dianisidines, pyranthrones, tetrachloroisoindolinones, dioxazines, monoazo acrylides, anthrapyrimidines and mixtures thereof;
e) about 5 to about 40 percent by weight of one or more plasticizers, and
f) about 5 to about 75 percent by weight of one or more fillers;
wherein the amounts recited are based on the weight of the composition and the composition forms a cross-linked polyurethane upon cure.

2. A composition according to claim 1 wherein the pigment is a white pigment.

3. A composition according to claim 1 wherein the pigment is titanium dioxide.

4. A composition according to claim 1 wherein the one or more hydroxyl amines correspond to the formula (R 1 ) 2 N—OH and the nitroxyls 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.

5. A composition according to claim 4 wherein the component c is a nitroxyl.

6. A composition according to claim 1 which further comprises a second stablilizer selected from ultraviolet stabilizers, durability stabilizers and light stabilizers.

7. A composition comprising:
a) about 20 to about 70 percent by weight of one or more 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 prepolymer and one or more oligomers or prepolymers containing isocyanate functional groups and alkoxysilane groups;
b) about 0.1 to about 2 percent by weight of one or more catalysts for the reaction of isocyanate moieties with active hydrogen atom containing groups;
c) one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitroxyl of a dihydrocarbyl hydroxyl amine or a nitroxyl of an alicyclic hydroxyl amine in an amount of about 0.01 to about 2.0 percent by weight; and
d) about 0.01 to about 25 percent by weight of a pigment selected from zinc oxide, cerium oxide, titanium dioxide, phthalocyanines, anthraquinones, perylenes, carbazoles, monoazo- and disazobenzimidazolones, isoindolinones, monoazonaphthols, di-arylidepyrazolones, rhodamines, indigoids, quinacridones, diazo-pyranthrones, dinitranilines, pyrazolones, dianisidines, pyranthrones, tetrachloroisoindolinones, dioxazines, monoazo acrylides, anthrapyrimidines and mixtures thereof;
e) about 5 to about 40 percent by weight of one or more plasticizers; and
f) about 5 to about 75 percent by weight of the one or more fillers;
wherein the composition is a two part composition wherein part 1 comprises one or more isocyanate functional components or one or more oligomers or prepolymers containing isocyanate functional groups and alkoxysilane groups; 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; wherein the one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitroxyl of a dihydrocarbyl hydroxyl amine or a nitroxyl of an alicyclic hydroxyl amine and the pigment may be present in part 1, part 2 or both; the amounts recited are based on the weight of the composition and the composition forms a cross-linked polyurethane upon cure.

8. A composition comprising
a) about 20 to about 70 percent by weight of one or more isocyanate functional components comprising one or more oligomers or prepolymers containing isocyanate functional groups and alkoxysilane groups;
b) about 0.1 to about 2 percent by weight of one or more catalysts for the reaction of isocyanate moieties with active hydrogen atom containing groups; and
c) one or more compounds comprising a dihydrocarbyl hydroxyl amine, an alicyclic hydroxyl amine, a nitroxyl of a dihydrocarbyl hydroxyl amine or a nitroxyl of an alicyclic hydroxyl amine in an amount of about 0.01 to about 2.0 percent by weight of the composition to resist degradation of the composition in a cured state;
d) about 5 to about 40 percent by weight of one or more plasticizers; and;
e) about 5 to about 75 percent by weight one or more fillers;
wherein the amounts are based on the weight of the composition and the composition forms a cross-linked polyurethane upon cure.

9. 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.

10. A method of bonding two or more substrates together which comprises contacting the two or more substrates together with a composition according to according to claim 9 disposed along at least a portion of the area wherein the substrates are in contact 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.

11. A method according to claim 9 wherein at least one of the substrates is a non-structural component and at least one of the other substrates is a building or a vehicle.

12. A method comprising applying a composition according to claim 1 along adjoining surfaces of two components in a structure and allowing the composition to cure such that the space between the adjoining surfaces is sealed.

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

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

Assignees

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

Inventors

• Ristoski Toni
• Jialanella Gary L
• Frishcosy Michael

Classifications

• C08G18/307

  Atmospheric humidity · CPC title

• C08G18/12 Primary

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08K5/32

  Compounds containing nitrogen bound to oxygen · CPC title

• B60J1/00

  Windows; Windscreens; Accessories therefor (B60J10/00 takes precedence; air curtains instead of windows B60J9/04 {; sealing strips for windshields B60J10/70; sealing sash guides for sliding window panes B60J10/74; glass partitions inside vehicles to protect occupants against personal attack B60R21/12}) · CPC title

• C08L75/04

  Polyurethanes · CPC title