Aldehyde free thermoset bioresins and biocomposites

Patent metadata

Field	Value
Publication number	US-2016215088-A1
Application number	US-201314442458-A
Country	US
Kind code	A1
Filing date	Nov 12, 2013
Priority date	Nov 16, 2012
Publication date	Jul 28, 2016
Grant date	—

Abstract

Aldehyde-free bio-based resin and composite materials include flexible or rigid thermoset resins of epoxidized oils derived from unsaturated oils which are cured with crosslinking carboxylic acids, natural food acids, anhydrides and acid anhydrides, and may be combined with different lignocellulosic fibers, forestry products or waste, with up to 100% renewable content.

First claim

1 . A method for preparing a thermoset resin prepolymer comprising the step of reacting an epoxidized oil derived from an unsaturated oil with a crosslinking carboxylic acid or an anhydride to prepare a prepolymer.

2 . The method of claim 1 comprising the further step of molding and curing the prepolymers at elevated temperatures to make neat thermoset resins.

3 . The method of claim 1 comprising the further step of mixing the prepolymer with reinforcing fibers and curing the material to form a thermoset composite material.

4 . The method of claim 3 wherein some or all of the epoxidized oil, or the carboxylic acid, or the reinforcing fibers, are derived from renewable sources.

5 . The method of claim 4 wherein the carboxylic acid comprises a natural food acid.

6 . The method of claim 1 wherein the carboxylic acid comprises citric, malic, tartaric, oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, or lactic acid, or mixtures thereof.

7 . The method of claim 1 wherein the crosslinking anhydride comprises aliphatic and aromatic anhydride or acid anhydride.

8 . The method of claim 7 wherein the crosslinking anhydride comprises maleic, phthalic, trimellitic, pyromellitic, isophthalic, tetraphthtalic or succinic anhydrides, or mixtures thereof.

9 . The method of claim 4 wherein the epoxidized oil is derived from an oil or fat comprising esterified unsaturated fatty acids.

10 . The method of claim 9 wherein the epoxidized oil is derived from unsaturated oil comprising acylglycerides comprising monounsaturated or polyunsaturated fatty acids.

11 . The method of claim 9 wherein the epoxidized oil is derived from alkyl esters of unsaturated fatty acids.

12 . The method of claim 10 wherein the epoxidized oil is derived from linseed, canola, soybean, or camelina oil.

13 . A thermoset resin prepolymer comprising an epoxidized oil derived from an unsaturated oil, mixed with a crosslinking carboxylic acid or a crosslinking anhydride.

14 . The prepolymer of claim 13 wherein the epoxidized oil and the carboxylic acid are derived from renewable sources.

15 . The prepolymer of claim 10 wherein the carboxylic acid comprises a natural food acid.

16 . The prepolymer of claim 15 wherein the carboxylic acid comprises citric, malic, tartaric, acetic, oxalic, tannic, caffeotannic, benzoic, butyric, or lactic acid.

17 . The prepolymer of claim 13 wherein the epoxidized oil is derived from vegetable oil comprising acylglycerols comprising mono- or polyunsaturated fatty acids.

18 . The prepolymer of claim 17 wherein the epoxidized oil is derived from linseed, canola, soybean, or camelina oil.

19 . A thermoset polymer comprising a cured prepolymer as claimed in claim 13 .

20 . A biocomposite material comprising a cured prepolymer as claimed in claim 13 and a reinforcing fiber.

21 . (canceled)

Assignees

• Univ Alberta

Inventors

• Omonov Tolibjon
• Curtis Jonathan

Classifications

• C08G59/20

  characterised by the epoxy compounds used · CPC title

• C08G59/027

  obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer · CPC title

• C08G59/4207 Primary

  aliphatic · CPC title

• C08J2363/00

  Characterised by the use of epoxy resins; Derivatives of epoxy resins · CPC title

• C08G59/4238

  heterocyclic · CPC title