Acetoacetylated and (meth)acrylated lignin and thermosets therefrom

Patent metadata

Field	Value
Publication number	US-10851244-B2
Application number	US-201715794500-A
Country	US
Kind code	B2
Filing date	Oct 26, 2017
Priority date	Oct 26, 2016
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

The invention relates to novel acetoacetylated lignin resin compositions comprising the reaction product of lignin and an acetoacetate ester. The invention also relates to novel (meth)acrylated lignin resin compositions comprising the reaction product of lignin and a (meth)acrylic compound. The invention also relates to methods of making the novel acetoacetylated lignin resin compositions and the novel (meth)acrylated lignin resin compositions. The invention also relates to curable coating compositions comprising the novel acetoacetylated lignin resin composition or (meth)acrylated lignin resin composition. The invention also relates to methods of making the curable coating compositions of the invention. The invention also relates to methods of applying curable coating compositions of the invention to substrates. The invention also relates to articles of manufacture comprising a curable coating composition of the invention and a method of making such article.

First claim

The claimed invention is:

1. An acetoacetylated lignin resin composition, comprising the reaction product of a mixture of lignin and at least one polyol with an acetoacetate ester.

2. The acetoacetylated lignin resin composition of claim 1 , wherein at least a fraction of the hydroxyl groups on the lignin are substituted with acetoacetate groups.

3. The acetoacetylated lignin resin composition of claim 1 , wherein the hydroxyl groups on the lignin are fully substituted with acetoacetate groups.

4. The acetoacetylated lignin resin composition of claim 1 , wherein the hydroxyl groups on the polyol are substituted with acetoacetate groups.

5. The acetoacetylated lignin resin composition of claim 1 , wherein the acetoacetate ester is tertiary-butyl acetoacetate.

6. The acetoacetylated lignin resin composition of claim 1 , wherein the at least one polyol is selected from the group consisting of a diol, a triol, and mixtures thereof.

7. The acetoacetylated lignin resin composition of claim 6 , wherein the diol is selected from the group consisting of diethylene glycol, 2-butyl-2-ethyl-1,3-propanediol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, neopentyl glycol, and mixtures thereof.

8. The acetoacetylated lignin resin composition of claim 6 , wherein the triol is selected from the group consisting of trimethylolpropane, trimethylolethane, glycerol, and mixtures thereof.

9. The acetoacetylated lignin resin composition of claim 1 , wherein:
the lignin is Kraft lignin;
the polyol is selected from the group consisting of 1,4-butanediol, diethylene glycol, ethylene glycol, and glycerol; and
the acetoacetate ester is tertiary-butyl acetoacetate.

10. The acetoacetylated lignin resin composition of claim 1 , further comprising at least one additive.

11. A method for producing the acetoacetylated lignin resin composition of claim 1 , comprising the step of contacting lignin with the acetoacetate ester in the presence of the at least one polyol, and optionally, a catalyst.

12. A curable composition comprising the acetoacetylated lignin resin composition of claim 1 and a multifunctional amine, or a melamine formaldehyde resin and a catalyst, or a multifunctional acrylic acid ester and a catalyst.

13. A cured composition of claim 12 .

14. An article of manufacture, comprising the curable composition of claim 12 .

15. A substrate coated with the curable composition of claim 12 .

16. The substrate of claim 15 , wherein the substrate is selected from the group consisting of paper, polyester film, metal, glass, and urethane elastomers.

Assignees

• Ndsu Res Foundation

Inventors

• Webster Dean C
• Krall Eric
• Sutko Kelly M

Classifications

• C08H6/00

  Macromolecular compounds derived from lignin, e.g. tannins, humic acids · CPC title

• C08K5/10

  Esters; Ether-esters · CPC title

• C08L97/005 Primary

  Lignin · CPC title

• C08K5/1515

  Three-membered rings · CPC title