IP Library Granted Patent US 12,252,590
Granted Patent B2
US 12,252,590 · App. 17/106,866 · Granted Mar 18, 2025

Acetoacetylated and (meth)acrylated resin compositions and thermosets and foams therefrom

Inventors: Dean C. Webster (Fargo, ND); Eric M. Krall (Minneapolis, MN); Kelly M. Sutko (Maple Grove, MN); Alexander T. Hart (Farmington, MN); Karan Bansal (Fargo, ND); Mohiuddin Quadir (West Fargo, ND)
Assignee: NDSU RESEARCH FOUNDATION
C08H6/00C08J9/141C08L97/005C08J2203/14C08J2397/00C08J2483/04
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Quick Facts
Patent No.
US 12,252,590
App. No.
17/106,866
Granted
Mar 18, 2025
Kind
B2
Abstract

The invention relates to acetoacetylated lignin resin compositions comprising the reaction product of lignin and an acetoacetate ester. The invention also relates to (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 acetoacetylated and (meth)acrylated lignin resin compositions. The invention also relates to curable coating compositions comprising the acetoacetylated and (meth)acrylated lignin resin compositions. 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. The invention also relates to foam materials comprising the reaction product of an acetoacetylated resin composition, a polyamine compound, and a physical blowing agent and/or a polysiloxane compound.

Claims (31)

1. A foam material, comprising the reaction product of:

a) at least one acetoacetylated resin composition;

b) at least one polyamine compound;

c) at least one physical blowing agent and/or at least one polysiloxane compound;

d) optionally at least one surfactant; and e) optionally phytic acid.

2. The foam of claim 1 , wherein the acetoacetylated resin composition comprises the reaction product of:

a1) at least one polyol;

a2) optionally lignin; and

a3) at least one acetoacetate ester.

3. The foam of claim 2 , wherein the at least one polyol is selected from the group consisting of a diol, a triol, and mixtures thereof.

4. The foam of claim 3 , 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.

5. The foam of claim 3 , wherein the triol is selected from the group consisting of trimethylolpropane, trimethylolethane, glycerol, and mixtures thereof.

6. The foam of claim 2 , wherein the lignin is present.

7. The foam of claim 2 , wherein the acetoacetate ester is tertiary-butyl acetoacetate.

8. The foam of claim 2 , wherein:

the polyol is selected from the group consisting of 1,4-butanediol, 1,3-propanediol, diethylene glycol, ethylene glycol, and glycerol;

the lignin is Kraft lignin; and

the acetoacetate ester is tertiary-butyl acetoacetate.

9. The foam of claim 1 , wherein the acetoacetylated resin composition is present in an amount ranging from about 25-95 wt %.

10. The foam of claim 1 , wherein the polyamine compound is tris (2-aminoethyl)amine.

11. The foam of claim 1 , wherein the polyamine compound is present in an amount ranging from about 5-75 wt %.

12. The foam of claim 1 , wherein the physical blowing agent is present in an amount ranging from about 0.5-45 wt %.

13. The foam of claim 1 , wherein the polysiloxane compound is selected from the group consisting of poly(methylhydrosiloxane), copolymers of poly(methylhydrosiloxane), tetramethylcyclotetrasiloxane, and mixtures thereof.

14. The foam of claim 1 , wherein the polysiloxane compound is present in an amount ranging from about 0.1-20 wt %.

15. The foam of claim 1 , wherein the surfactant is present in an amount ranging from about 0.1-5 wt %.

16. The foam of claim 1 , wherein the phytic acid is present in an amount ranging from about 0.1-45 wt %.

17. The foam of claim 1 , wherein the foam is fire retardant as determined by UL-94V standardization.

18. A method for making the foam of claim 1 , comprising the step of contacting the at least one acetoacetylated resin composition with the at least one polyamine compound, the at least one physical blowing agent and/or at least one polysiloxane compound, the at least one optional surfactant, and the optional phytic acid.

19. An article of manufacture, comprising the foam of claim 1 .

20. The foam of claim 6 , wherein the lignin is Kraft lignin.

21. The foam of claim 1 , wherein the polyamine compound is a polyfunctional amine compound.

Assignments (3)
CONFIRMATORY LICENSE Recorded Jun 7, 2023
From: NORTH DAKOTA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 063903/0629 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2021
From: WEBSTER, DEAN C.; KRALL, ERIC; SUTKO, KELLY M.; HART, ALEXANDER T.; BANSAL, KARAN; QUADIR, MOHIUDDIN
To: NORTH DAKOTA STATE UNIVERSITY
Reel/Frame 054902/0279 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2021
From: NORTH DAKOTA STATE UNIVERSITY
To: NDSU RESEARCH FOUNDATION
Reel/Frame 054902/0318 →
Continuity (3)
Continuation In Part 15794500 · Oct 26, 2017
Provisional Application 62413225 · Oct 26, 2016
Related Publication 20210171720A1 · Jun 10, 2021
References Cited (5)
US 20070173602A1 · Brinkman · 2007 [cited by examiner]
CN 105780474A · 2016 [cited by applicant]
EP 1165713B1 · 2003 [cited by examiner]
Dziurka et al., “The Effect of Grafting Particles with Acetoacetyl Groups on the Properties of Particleboards,” Elec. J. Polish Agric. Univ., Wood Tech., vol. 6, Issue 2 [retrieved on Apr. 13, 2019]. Retrieved from the … [cited by applicant]
CN 105780474 A, machine translation, EPO Espacenet. (Year: 2016). [cited by applicant]