Aziridinated triglycerides and polymers formed therefrom

Patent metadata

Field	Value
Publication number	US-10501448-B2
Application number	US-201816042565-A
Country	US
Kind code	B2
Filing date	Jul 23, 2018
Priority date	Apr 6, 2015
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

Various embodiments disclosed relate to aziridinated triglycerides and polymers formed therefrom. In various embodiments, the present invention provides an aziridinated triglyceride having the structure described herein. In various embodiments, the present invention provides a method of making the aziridinated triglyceride, a method of crosslinking the aziridinated triglyceride to form a polymer, the polymer formed from the aziridinated triglyceride, a triglyceride with at least one pendent unsaturated group that can be used to form the aziridinated triglyceride, and a method of making the triglyceride having at least one pendent unsaturated group.

First claim

What is claimed is:

1. A polymer comprising a plurality of units of Formula (I):

wherein
R 1 , R 2 , and R 3 are each independently a substituted or unsubstituted (C 1 -C 50 )hydrocarbyl and at least one of R 1 , R 2 , and R 3 is interrupted or terminated by the A end of at least one -AZP— group having the structure:

at each occurrence, L l is independently a substituted or unsubstituted (C 2 -C 50 )hydrocarbyl interrupted or terminated with 0, 1, 2, or 3 groups independently chosen from —O—, —S—, and substituted or unsubstituted —NH—,
at each occurrence, R 4 , R 5 , R 6 , and R 7 are independently chosen from —H and substituted or unsubstituted (C 1 -C 10 )hydrocarbyl interrupted or terminated with 0, 1, 2, or 3 groups independently chosen from —O—, —S—, and substituted or unsubstituted —NH—,
at each occurrence, R b is independently a substituted or unsubstituted (C 1 -C 50 )hydrocarbyl having a valence of z+1, wherein R b is interrupted or terminated by 0, 1, 2, or 3 groups independently chosen from —O—, —S—, substituted or unsubstituted —NH—, and —(O—(C 2 -C 3 )alkylene) n— , wherein n is about 1 to about 10,000 and wherein the (C 2 -C 3 )alkylene is substituted or unsubstituted,
z is about 1 to about 1,000, and
each B end of the -AZP— group independently interrupts or terminates R 1 , R 2 , or R 3 of the same unit of Formula (I) or of one or more separate units of Formula (I), and at least one -AZP— group links two or more separate units of Formula (I).

2. The polymer of claim 1 , wherein the polymer has about 2 to about 100,000,000 units of Formula (I).

3. The polymer of claim 1 , wherein -AZP— has the structure:

4. The polymer of claim 1 , wherein triglyceride I has the structure:

5. The polymer of claim 1 , wherein the unit of Formula (I) comprises two or more -AZP— groups.

6. The polymer of claim 1 , wherein each of R 1 , R 2 , and R 3 have no more than one -AZP— group.

7. The polymer of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is interrupted or terminated by at least two -AZP— groups.

8. The polymer of claim 1 , wherein R 1 , R 2 , and R 3 are each independently a substituted or unsubstituted (C 10 -C 50 )hydrocarbyl and each of R 1 , R 2 , and R 3 is interrupted or terminated by at least one -AZP—group.

9. The polymer of claim 1 , wherein R 1 , R 2 , and R 3 are each independently unsubstituted (C 1 -C 50 )alkane; unsubstituted (C 1 -C 50 )alkane interrupted or terminated with at least one -AZP— group, or unsubstituted (C 1 -C 50 )alkane substituted with 0, 1, 2, 3, 4, or 5 epoxy groups.

10. The polymer of claim 1 , wherein R 1 , R 2 , and R 3 are each independently an unsubstituted (C 1 -C 50 )alkane or unsubstituted (C 1 -C 50 )alkane interrupted or terminated with at least one -AZP— group.

11. The polymer of claim 1 , wherein at each occurrence, L l is independently an unsubstituted (C 2 -C 10 )alkanylene.

12. The polymer of claim 1 , wherein at each occurrence, R 4 , R 5 , R 6 , and R 7 are —H or unsubstituted (C 1 -C 10 )hydrocarbyl.

13. The polymer of claim 1 , wherein at each occurrence, R 5 , R 6 , and R 7 are —H.

14. The polymer of claim 1 , wherein at each occurrence, R 5 , R 6 , and R 7 are —H, and R 4 is unsubstituted (C 1 -C 10 )hydrocarbyl.

15. The polymer of claim 1 , wherein at each occurrence, R 5 , R 6 , and R 7 are —H, and R 4 is unsubstituted (C 1 -C 5 )alkyl.

16. The polymer of claim 1 , wherein R b taken together with the carboxylates to which it is attached corresponds to an oxalic acid, maleic acid, succinic acid, methylsuccinic acid, malonic acid, adipic acid, glutaric acid, fumaric acid, dihydroxyfumaric acid, malic acid, mesaconic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, 1,2, 1,3-, or 1,4-cyclohexane dicarboxylic acid, 1,2,3-cyclohexane tricarboxylic acid, 1,2,4-cyclohexane tricarboxylic acid, 1,3,5-cyclohexane tricarboxylic acid, 1,2-or 1,3-cyclopentane dicarboxylic acid, citric acid, tartaric acid, dihydroxyterephthalic acid, 1,2,3, 1,2,4, or 1,2,5-benzene tricarboxylic acid, tricarballylic acid, 1,2,4,5-benzene tetracarboxylic acid, norbornene tetracarboxylic acid, 3,3′,4,4′-benzophenone tetracarboxylic acid, 1,2,3,4,5,6-benzene hexacarboxylic acid, aspartic acid, polyacrylic acid, glutamic acid, or an isosorbide-based diacid linker.

17. The polymer of claim 1 , wherein R b taken together with the carboxylates to which it is attached, corresponds to a linker derived from

wherein
fused rings A and B are each independently chosen from substituted or unsubstituted (C 5 -C 10 )cycloalkyl and (C 2 -C 10 )heterocyclyl,
m and n are each independently 1-8, and
at each occurrence R′ is independently chosen from substituted or unsubstituted (C 2 -C 10 )hydrocarbylene.

18. The polymer of claim 1 , wherein R b taken together with the carboxylates to which it is attached, corresponds to a linker derived from:

19. The polymer of claim 1 , wherein R b taken together with the carboxylates to which it is attached, corresponds to a linker derived from:

20. The polymer of claim 1 , wherein the unit of Formula (I) is derived from açaí oil, almond oil, amaranth oil, apple seed oil, apricot oil, argan oil, avocado oil, babassu oil, beech nut oil, ben oil, bitter gourd oil, black seed oil, blackcurrant seed oil, borage seed oil, borneo tallow nut oil, bottle gourd oil, buffalo gourd oil, butternut squash seed oil, camelina sativa oil, cape chestnut oil, carob pod oil, cashew oil, cocklebur oil, cocoa butter, coconut oil, cohune oil, coriander seed oil, corn oil, cottonseed oil, date seed oil, dika oil, egusi seed oil, evening primrose oil, flaxseed oil, grape seed oil, grapefruit seed oil, hazelnut oil, hemp oil, kapok seed oil, kenaf seed oil, lallemantia oil, linseed oil, macadamia oil, mafura oil, marula oil, meadowfoam seed oil, mongongo nut oil, mustard oil, niger seed oil, okra seed oil, olive oil, orange oil, palm oil, papaya seed oil, peanut oil, pecan oil, pequi oil, perilla seed oil, persimmon seed oil, pili nut oil, pistachio oil, pomegranate seed oil, poppyseed oil, prune kernel oil, pumpkin seed oil, quinoa oil, ramtil oil, rapeseed oil, rice bran oil, royle oil, safflower oil, sapote oil, seje oil, sesame oil, shea butter, soybean oil, sun

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Chen Ruqi
• Chen Jason Shih-Hao
• Zhang Chaoqun
• Kessler Michael Richard

Classifications

• C08G73/02

  Polyamines · CPC title

• C07D405/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C08G63/6852

  derived from hydroxy carboxylic acids · CPC title