Compositions using polyuretdione resins

Patent metadata

Field	Value
Publication number	US-11292864-B2
Application number	US-201815933470-A
Country	US
Kind code	B2
Filing date	Mar 23, 2018
Priority date	Mar 23, 2018
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

The present invention provides a reaction mixture comprising a hot blend of a first isocyanate-based uretdione resin and a second isocyanate-based uretdione resin, a neutralized polyol and a tertiary amine catalyst, and optionally, an additive package selected from the group consisting of flow control additives, pigments (colorants), wetting agents, and solvents, wherein the first isocyanate and the second isocyanate are different. The isocyanate-based uretdiones that have been hot blended together produce coatings, adhesives, castings, composites, and sealants, which exhibit better performance properties (such as microhardness) than those coatings, adhesives, castings, composites, and sealants produced from the constituent isocyanate-based uretdiones alone.

First claim

What is claimed is:

1. A reaction mixture comprising:
a hot blend of a 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione resin and a 1,6-hexamethylene diisocyanate (HDI)-based uretdione resin;
a neutralized polyol comprising a reaction product of a polyester polyol and an acid scavenger; and
a tertiary amine catalyst selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,4,5,6-tetrahydro-1,2-dimethylpyrimidine, sodium-1,2,4-triazolide, 2-tert-butyl-1,1,3,3-tetramethylguanidine, and combinations thereof,
optionally, a hydrocarbon solvent,
optionally, an additive package selected from the group consisting of flow control additives, pigments, and wetting agents,
wherein 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione resin and 1,6-hexamethylene diisocyanate (HDI)-based uretdione resin are blended in a weight ratio of between 92:8 and 74:26.

2. The reaction mixture according to claim 1 , wherein the tertiary amine catalyst is 1,8-diazabicyclo[5.4.0]undec-7-ene.

3. The reaction mixture according to claim 1 , wherein the acid scavenger is covalently bonded to acidic groups within the polyol and is selected from the group consisting of carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, oxazolines, and combinations thereof.

4. One of a coating, an adhesive, a casting, a composite, and a sealant comprising the reaction mixture according to claim 1 .

5. A method of applying the reaction mixture according to claim 1 to a substrate, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.

6. A method of making a polymer comprising:
hot blending a 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione resin and a 1,6-hexamethylene diisocyanate (HDI)-based uretdione resin at a weight ratio of between 92:8 and 74:26 to form a resin hot blend;
reacting the resin hot blend with a neutralized polyester polyol in the presence of a tertiary amine catalyst and optionally a hydrocarbon solvent,
optionally, in the presence of an additive package selected from the group consisting of flow control additives, pigments, wetting agents,
wherein the neutralized polyester polyol comprises a reaction product of a polyester polyol and an acid scavenger and wherein the tertiary amine catalyst is selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,4,5,6-tetrahydro-1,2-dimethylpyrimidine, sodium-1,2,4-triazolide, 2-tert-butyl-1,1,3,3-tetramethylguanidine, and combinations thereof.

7. The method according to claim 6 , wherein the tertiary amine catalyst is 1,8-diazabicyclo[5.4.0]undec-7-ene.

8. The method according to claim 6 , wherein the acid scavenger is covalently bonded to acidic groups within the polyol and is selected from the group consisting of carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, oxazolines, and combinations thereof.

9. A polymer made according to the method of claim 6 .

10. One of a coating, an adhesive, a casting, a composite, and a sealant comprising the polymer made according to claim 6 .

11. A method of applying the polymer made according to claim 6 to a substrate, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.

Assignees

• Covestro Llc
• Covestro Deutschland Ag

Inventors

• Ekin Alan
• Stempfle Florian Johannes
• Bushmire Alan D

Classifications

• C08G18/027 Primary

  the polymeric products containing urethodione groups · CPC title

• C09D175/02

  Polyureas · CPC title

• C08G18/6229

  Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols · CPC title

• C08G18/798

  containing urethdione groups · CPC title

• C09J175/04

  Polyurethanes · CPC title