Ester carbonate polyols for hydrolytically stable adhesives

Patent metadata

Field	Value
Publication number	US-9222008-B2
Application number	US-201214357262-A
Country	US
Kind code	B2
Filing date	Dec 4, 2012
Priority date	Dec 14, 2011
Publication date	Dec 29, 2015
Grant date	Dec 29, 2015

Abstract

A two-component curable adhesive or sealant composition is provided. The first component may comprise a mixture of at least one polyol selected from the group comprising a polyester polyol, a polyester-polycarbonate copolymer polyol, and combinations thereof, a resin, and optionally a solvent. The second component may comprise a prepolymer obtained by reacting a polyester-polycarbonate copolymer polyol which is the reaction product of a polyester polyol which is the reaction product of one or more organic acids, and one or more glycols having a functionality of two or more and one or more polycarbonate polyols, at least one organic polyisocyanate component, and at least one chain extending agent and optionally a solvent. Alternatively, the first component may comprise a polyester-polycarbonate copolymer polyol, a resin, and optionally a solvent. The second component may comprise a polyisocyanate curative and optionally a solvent. The cured adhesive exhibits improved hydrolytic properties while maintaining excellent processability and adhesive properties.

First claim

The invention claimed is:

1. A two-component curable ahesive or sealant composition; comprising:
(a) a first component comprising a mixture of:
(i) at least one polyol selected from the group comprising a polyester polyol, a polyester-polycarbonate copolymer polyol, and combinations thereof;
(ii) a resin; and
(iii) optionally a solvent; and

(b) a second component comprising:
(i) a prepolymer obtained by reacting:
a polyester-polycarbonate copolymer polyol which is the reaction product of:
a polyester polyol which is the reaction product of:
 one or more organic acids; and
 one or more glycols having a functionality of two or more; and
one or more polycarbonate polyols;

at least one organic polyisocyanate component; and
at least one chain extending agent; and

(ii) optionally a solvent.

2. The composition of claim 1 , wherein the one or more organic acids are selected from phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, tetrachlorophthalic acid, oxalic acid, adipic acid, azelaic acid, sebacic acid, succinic acid, malic acid, glutaric acid, malonic acid, pimelic acid, suberic acid, 2,2-dimethylsuccinic acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, maleic acid, fumaric acid, itaconic acid, fatty acids, and combinations thereof.

3. The composition of claim 2 , wherein the one or more glycols having a functionality of two or more are selected from ethylene glycol, propylene glycol-(1,2), propylene glycol-(1,3), octane-1,8-diol, neopentyl glycol, cyclohexane dimethanol (1,4-bis-hydroxymethylcyclohexane), 1-6-hexanediol, 1,4-butanediol, 2-methyl-1,3-propane diol, glycerine, trimethylolpropane, hexanetriol-(1,2,6) butane triol-(1,2,4), trimethylolethane, pentaerythritol, quinitol, mannitol, sorbitol, methylglycoside, diethylene glycol, triethylene glycol, tetrathylene glycol, polyethylene glycols, dibutylene glycol, polybutylene glycols, and combinations thereof.

4. The compositions of claim 3 , wherein the one or more organic acids include adipic acid and isophthalic acid and the one more glycols includes 1, 6-hexanediol.

5. The composition of claim 1 , wherein the one or more polycarbonate polyols comprise:
(a) repeating units from one or more alkane diols having 2 to 50 carbon atoms with a number average molecular weight between 500 and 3,000; and
(b) at least one carbonate compound selected from alkylene carbonates, diaryl carbonates, dialkyl carbonates, dioxolanones, hexanediol bis-chlorocarbonates, phosgene, urea, and combinations thereof.

6. The composition of claim 5 , wherein the one or more alkane diols is selected from 1,4-butanediol, 1,5-pentanediol, 1,6-hexandiol, 1,7-heptanediol, 1,2-dodecanediol, cyclohexanedimethanol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, bis(2-hydroxyethyl)ether, bis(6-hydroxyhexyl)ether or short-chain C 2 , C 3 or C 4 polyether diols having a number average molecular weight of less than 700 g/mol, and combinations thereof.

7. The composition of claim 5 , wherein the at least one carbonate compound is selected from alkylene carbonates, diaryl carbonates, dialkyl carbonates, dioxolanones, hexanediol bis-chlorocarbonates, phosgene or urea.

8. The composition of claim 1 , wherein the at least one organic polyisocyanate components are selected from polymeric polyisocyanates, aromatic isocyanates, cycloaliphatic isocyanates, or aliphatic isocyanates.

9. The composition of claim 8 , wherein the at least one organic polyisocyanate components is a polymethylene polyphenylisocyanate that contains diphenylmethane diisocyanate (MDI).

10. The composition of claim 1 , wherein the resin is selected from an acrylic resin, a phenol-formaldehyde resin, and combinations thereof.

11. The composition of claim 1 , wherein the chain extending agent is trimethylol propane.

12. The composition of claim 1 further comprising: in either or both of (a) and (b), one or more materials selected from the group consisting of leveling agents, wetting agents, flow control agents, fillers, viscosity regulators, plasticizers, pigments, dyes, UV absorbers, adhesion promoters, thermal stabilizers, and mixtures thereof.

13. The composition of claim 1 , wherein the at least one polyol is present at from 30 to 80 weight percent of the first component (a).

14. The composition of claim 1 , wherein the polyester -polycarbonate copolymer polyol is present at from 10 to 60 weight percent of the prepolymer.

15. The composition of claim 1 , wherein the first component (a) is present at from 60 to 90 weight percent of the two-component composition and the second component (b) is present at from 10 to 40 weight percent of the two-component composition.

Assignees

• Singh Harpreet
• Bertolone Viviano
• Rubulotta Orazio
• Jimenez Jorge
• Heath William H
• Singh Amarnath
• Koonce William A
• Dow Global Technologies Llc
• Rohm & Haas

Inventors

• Singh Harpreet
• Bertolone Viviano
• Rubulotta Orazio
• Jimenez Jorge
• Heath William H
• Singh Amarnath
• Koonce William A

Classifications

• C08G63/64 Primary

  Polyesters containing both carboxylic ester groups and carbonate groups · CPC title

• C09J163/04

  Epoxynovolacs · CPC title

• C08G18/10 Primary

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C09J175/06 Primary

  from polyesters · CPC title

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title