Curable and cured compositions

Patent metadata

Field	Value
Publication number	US-9290683-B2
Application number	US-201113881429-A
Country	US
Kind code	B2
Filing date	Nov 8, 2011
Priority date	Nov 12, 2010
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

Curable compositions, cured compositions, and articles that include the cured compositions are described. The curable composition contains a) an epoxy resin, b) a curing agent, c) a reactive liquid modifier, and d) a toughening agent. The reactive liquid modifier is an acetoacetate ester of a polyol that is a vegetable oil, that is prepared from a vegetable oil, or that is a mixture thereof. The cured compositions can be used as adhesives such as structural adhesives or as polymeric coatings.

First claim

We claim:

1. A curable composition having a first part and a second part, the curable composition comprising:
a) an epoxy resin, wherein the epoxy resin is in the first part of the curable composition;
b) a curing agent having at least two groups of formula —NR 1 H where R 1 is selected from hydrogen, alkyl, aryl, or alkylaryl, wherein the curing agent is in the second part of the curable composition;
c) a toughening agent, wherein the toughening agent is in the first part, in the second part, or in both the first part and the second part of the curable composition and wherein the toughening agent is a core-shell polymer, a butadiene-nitrile rubber, acrylic polymer or copolymer, an adduct of an amino-terminated material and an epoxy resin, or an adduct of a carboxy-terminated material and an epoxy resin; and
d) a reactive liquid modifier that is in the first part of the curable composition, the reactive liquid modifier comprising an acetoacetate ester of a polyol that is a vegetable oil, that is prepared from a vegetable oil, or that is a mixture thereof, wherein the polyol comprises a triglyceride having at least two hydroxyl groups and wherein the acetoacetate ester has at least two acetoacetoxy groups.

2. The curable composition of claim 1 , wherein the polyol is of Formula (VIII)

wherein
each R 9 is an aliphatic group having at least 8 carbon atoms and that is saturated or unsaturated;
at least two of the R 9 groups have at least one hydroxyl group, and
each R 9 group is optionally substituted with at least one alkoxy group.

3. The curable composition of claim 1 , wherein the curable composition comprises 20 to 90 weight percent epoxy resin, 3 to 30 weight percent curing agent, 3 to 20 weight percent reactive liquid modifier, and 5 to 55 weight percent toughening agent based on a total weight of the curable composition.

4. The curable composition of claim 1 , wherein the curable composition is free or substantially free of an oil displacing compound, of an oil adsorbing filler, or both.

5. The curable composition of claim 1 , wherein the curable composition further comprises 0.1 to 25 weight percent oil displacing agent based on a total weight of the curable composition.

6. The curable composition of claim 1 , wherein the curable composition further comprises 0.1 to 8 weight percent of an oil adsorbing filler.

7. A cured composition comprising a reaction product of a curable composition comprising:
a) an epoxy resin;
b) a curing agent having at least two groups of formula —NR 1 H where R 1 is selected from hydrogen, alkyl, aryl, or alkylaryl;
c) a toughening agent that is a core-shell polymer, a butadiene-nitrile rubber, acrylic polymer or copolymer, an adduct of an amino-terminated material and an epoxy resin, or an adduct of a carboxy-terminated material and an epoxy resin; and
d) a reactive liquid modifier that is in the first part of the curable composition, the reactive liquid modifier comprising an acetoacetate ester of a polyol that is a vegetable oil, that is prepared from a vegetable oil, or that is a mixture thereof, wherein the polyol comprises a triglyceride having at least two hydroxyl groups and wherein the acetoacetate ester has at least two acetoacetoxy groups.

8. The cured composition of claim 7 , wherein the polyol is of Formula (VIII)

wherein
each R 9 is an aliphatic group having at least 8 carbon atoms and that is saturated or unsaturated;
at least two of the R 9 groups have at least one hydroxyl group, and
each R 9 group is optionally substituted with at least one alkoxy group.

9. The cured composition of claim 7 , wherein the cured composition is an adhesive.

10. The cured composition of claim 7 , wherein the cured composition is a polymeric coating.

11. The cured composition of claim 7 , wherein the curable composition is free or substantially free of an oil displacing compound, of an oil adsorbing filler, or both.

12. An article comprising a first substrate and a cured composition positioned adjacent to the first substrate, the cured composition comprising a reaction product of a curable composition comprising:
a) an epoxy resin;
b) a curing agent having at least two groups of formula —NR 1 H where R 1 is selected from hydrogen, alkyl, aryl, or alkylaryl;
c) a toughening agent that is a core-shell polymer, a butadiene-nitrile rubber, acrylic polymer or copolymer, an adduct of an amino-terminated material and an epoxy resin, or an adduct of a carboxy-terminated material and an epoxy resin; and
d) a reactive liquid modifier that is in the first part of the curable composition, the reactive liquid modifier comprising an acetoacetate ester of a polyol that is a vegetable oil, that is prepared from a vegetable oil, or that is a mixture thereof, wherein the polyol comprises a triglyceride having at least two hydroxyl groups and wherein the acetoacetate ester has at least two acetoacetoxy groups.

13. The article of claim 12 , wherein the polyol is of Formula (VIII)

wherein
each R 9 is an aliphatic group having at least 8 carbon atoms and that is saturated or unsaturated;
at least two of the R 9 groups have at least one hydroxyl group, and
each R 9 group is optionally substituted with at least one alkoxy group.

Assignees

• Campbell Christopher J
• Lewandowski Kevin M
• Owusu-Adom Kwame
• 3M Innovative Properties Co

Inventors

• Campbell Christopher J
• Lewandowski Kevin M
• Owusu-Adom Kwame

Classifications

• C08G59/4007 Primary

  Curing agents not provided for by the groups C08G59/42 - C08G59/66 · CPC title

• C09J163/00 Primary

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08G59/50

  Amines · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08G59/56

  together with other curing agents · CPC title