IP Library › Granted Patent US 9,856,343
Granted Patent B2
US 9,856,343 · App. 15/474,101 · Granted Jan 2, 2018

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

Inventors: Giuseppe R. Palmese (Hainesport, NJ); John Joseph La Scala (Wilmington, DE); Joshua Matthew Sadler (Middle River, MD); Anh-Phuong Thy Lam (Newark, DE)
Assignees: Drexel University; The United States of America as Represented by the Secretary of the Army
C08F222/20C07D493/04C08F122/20C08F124/00C08F220/32C08F224/00C08F2220/325
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Quick Facts
Patent No.
US 9,856,343
App. No.
15/474,101
Granted
Jan 2, 2018
Kind
B2
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.

Claims (21)

1. A polymerizable monomer selected from the group consisting of:

2. A polymerizable monomer as claimed in claim 1 , wherein the monomer is:

3. A polymerizable monomer as claimed in claim 1 , wherein the monomer is:

4. A polymerizable monomer as claimed in claim 1 , wherein the monomer is:

5. A polymerizable monomer as claimed in claim 1 , wherein the monomer is:

6. A polymerizable monomer as claimed in claim 1 , wherein the monomer is:

7. A copolymer formed by curing a curable composition comprising at least one monomer selected from the group consisting of the polymerizable monomers of claim 1 using a free-radical initiator.

8. The copolymer of claim 7 , wherein the curable composition comprises at least one vinyl ester resin monomer and/or at least one unsaturated polyester monomer.

9. The copolymer of claim 8 , wherein the curable composition further comprises at least one reactive diluent.

10. The copolymer of claim 8 , wherein the curable composition comprises 1-99% by weight of at least one monomer selected from the group consisting of the polymerizable monomers of claim 1 , 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.

11. The copolymer of claim 8 , wherein the curable composition comprises 5-95% by weight of at least one monomer selected from the group consisting of the polymerizable monomers of claim 1 , 10-55% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-50% by weight of at least one reactive diluent.

12. The copolymer of claim 9 , wherein the composition comprises 15-90% by weight of at least one monomer selected from the group consisting of the polymerizable monomers of claim 1 , 10-55% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 5-45% by weight of at least one reactive diluent.

13. The copolymer of claim 8 , comprising a vinyl ester resin monomer selected from the group consisting of (meth)acrylated glycidyl ethers of bisphenols, (meth)acrylated ethoxylated bisphenols and novolac vinyl esters.

14. The copolymer of claim 8 , comprising a vinyl ester monomer 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.

15. The copolymer of claim 14 , wherein the curable composition further comprises a reactive diluent selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacrylated lauric acid and methacrylated fatty acids.

16. The copolymer of claim 15 , wherein the monomer of claim 1 is selected from a monomer of the formula 5 and a monomer of the formula 5a.

17. The copolymer of claim 15 , wherein the monomer of claim 1 is selected from a monomer of the formula 7 and a monomer of the formula 8.

18. The copolymer of claim 8 , wherein the curable composition comprises an unsaturated polyester monomer 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.

19. The copolymer of claim 18 , wherein the curable composition further comprises a reactive diluent selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacrylated lauric acid and methacrylated fatty acids.

20. The copolymer of claim 19 , wherein the monomer of claim 1 is selected from a monomer of the formula 5 and a monomer of the formula 5a.

21. The copolymer of claim 19 , wherein the monomer of claim 1 is selected from a monomer of the formula 7 and a monomer of the formula 8.

Continuity (4)
Continuation 15130165 · Apr 15, 2016
Continuation 14237170
Provisional Application 61521981 · Aug 10, 2011
Related Publication 20170298165A1 · Oct 19, 2017