Renewable bio-based (meth)acrylated monomers as vinyl ester cross-linkers

Patent metadata

Field	Value
Publication number	US-10053529-B2
Application number	US-201715824629-A
Country	US
Kind code	B2
Filing date	Nov 28, 2017
Priority date	Aug 10, 2011
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

Anhydrosugar-based monomers prepared from isosorbide, isomannide, and isoidide and resin systems containing these anhydrosugar-based monomers that are partially to fully bio-based, which may produce materials having properties that meet or exceed the properties of similar petroleum derived vinyl ester resins.

First claim

What is claimed is:

1. A method of making a polymer comprising the step of curing a composition comprising at least one polymerizable monomer selected from the group consisting of:

2. The method of claim 1 , wherein the curing is carried out by free-radical curing.

3. The method of claim 1 , wherein the composition further comprises from 1 to 99% by weight of at least one reactive diluent selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacrylated lauric acid, and methacrylated fatty acids.

4. The method of claim 1 , wherein the composition further comprises from 1 to 99% by weight of at least one cross-linking agent.

5. The method of claim 4 , wherein the crosslinker is selected from the group consisting of: unsaturated polyester, vinyl ester and the structures in claim 1 .

6. A polymer obtained by the process of claim 1 .

7. A method of making a polymer comprising the step of curing a composition comprising at least one vinyl ester resin monomer or unsaturated polyester monomer and at least one anhydrosugar-based polymerizable monomer selected from the group consisting of:

8. The method of claim 7 , wherein the composition comprises 1-99% by weight of anhydrosugar-based monomers, 1-70% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-60% by weight of at least one reactive diluent.

9. The method of claim 7 wherein the composition comprises 5-95% by weight by weight of anhydrosugar-based monomers, 5-65% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-50% by weight of at least one reactive diluent.

10. The method of claim 7 , wherein the composition comprises 15-90% by weight of anhydrosugar-based monomers, 10-55% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-45% by weight of at least one reactive diluent.

11. The method of claim 8 , wherein the reactive diluent is selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacrylated lauric acid and methacrylated fatty acids.

12. The method of claim 11 , wherein the vinyl ester monomer is selected from the group consisting of (meth)acrylated glycidyl ethers of bisphenols, (meth)acrylated ethoxylated bisphenols and novolac vinyl esters.

13. The method of claim 12 , wherein the bisphenols are selected from the group consisting of: bisphenol A, hexafluorobisphenol A, bisphenol E, bisphenol F, tetramethyl bisphenol E, tetramethyl bisphenol F, bisphenol M, bisphenol C, bisphenol P and bisphenol Z.

14. The method of claim 13 , wherein the unsaturated polyester monomer is made from one or more of the following components: phthalic acid, terephthalic acid, m-phthalic acid, suberic acid, adipic acid, succinic acid, maleic acid, fumaric acid, butylene glycol, propylene glycol, and ethylene glycol.

15. The method of claim 12 , wherein said composition comprises 50-95% by weight of said at least one monomer and 5-50% by weight of said reactive diluent.

16. A polymer obtained by the method of claim 8 .

17. The method of making a polymer as claimed in claim 1 , wherein the at least one polymerizable monomer is selected from the group consisting of:

18. The method of making a polymer as claimed in claim 1 , wherein the at least one polymerizable monomer is selected from the group consisting of:

19. The method of making a polymer as claimed in claim 8 , wherein the at least one anhydrosugar-based polymerizable monomer is selected from the group consisting of:

20. The method of making a polymer as claimed in claim 1 , wherein the at least one anhydrosugar-based polymerizable monomer is selected from the group consisting of:

Assignees

• Univ Drexel
• Us Army
• Us Army

Inventors

• Palmese Giuseppe R
• La Scala John Joseph
• Sadler Joshua Matthew
• Lam Anh-Phuong Thy

Classifications

• C08F220/282

  and containing two or more oxygen atoms · CPC title

• C08F224/00

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F218/00; cyclic anhydrides of unsaturated acids C08F220/00, C08F222/00) · CPC title

• C07D493/04

  Ortho-condensed systems · CPC title

• C08F122/20

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• C08F124/00

  Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F118/00; cyclic anhydrides of unsaturated acids C08F120/00, C08F122/00) · CPC title