Aziridinated triglycerides and polymers formed therefrom

Patent metadata

Field	Value
Publication number	US-10077257-B2
Application number	US-201615085345-A
Country	US
Kind code	B2
Filing date	Mar 30, 2016
Priority date	Apr 6, 2015
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

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. An aziridinated triglyceride having the structure:

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 at least one -AZ- group having the structure:

at each occurrence, L 1 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—.

2. The aziridinated triglyceride of claim 1 , wherein the aziridinated triglyceride comprises at least two -AZ- groups.

3. The aziridinated triglyceride 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 -AZ- group.

4. The aziridinated triglyceride of claim 1 , wherein R 1 , R 2 , and R 3 are each independently a substituted or unsubstituted (C 1 -C 50 )alkane and at least one of R 1 , R 2 and R 3 is interrupted or terminated with at least one -AZ— group.

5. The aziridinated triglyceride 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 -AZ- group, or unsubstituted (C 1 -C 50 )alkane substituted with 0, 1, 2, 3, 4, or 5 epoxy groups.

6. The aziridinated triglyceride 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 -AZ- group.

7. The aziridinated triglyceride of claim 1 , wherein at each occurrence, L 1 is independently an unsubstituted (C 2 -C 50 )alkanylene.

8. The aziridinated triglyceride of claim 1 , wherein at each occurrence, L 1 is independently an unsubstituted (C 2 -C 10 )alkanylene.

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

10. The aziridinated triglyceride of claim 1 , wherein at each occurrence, R 5 , R 6 , and R 7 are —H.

11. The aziridinated triglyceride 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.

12. The aziridinated triglyceride 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.

13. The aziridinated triglyceride of claim 1 , wherein -AZ- has the structure:

14. The aziridinated triglyceride of claim 1 , wherein the aziridinated triglyceride 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, sunflower oil, taramira oil, tea seed oil, thistle oil, tigernut oil, tobacco seed oil, tomato seed oil, walnut oil, watermelon seed oil, wheat germ oil, agarwood oil, allspice oil, almond oil, anise oil, basil oil, bay leaf oil, benzoin oil, bergamot oil, buchu oil, camphor oil, cannabis oil, cassia oil, cedar oil, celery oil, chamomile oil, cinnamon oil, clary sage oil, clove oil, copaiba oil, cumin oil, eucalyptus oil, frankincense oil, galangal oil, geranium oil, ginger oil, grapefruit oil, guava oil, hops oil, hyssop oil, jasmine oil, juniper oil, lavender oil, lemon grass oil, lemon oil, lemongrass oil, lime oil, manuka oil, mandarin orange, marjoram oil, melaleuca oil, myrrh oil, nutmeg oil, orange oil, oregano oil, patchouli oil, peppermint oil, pine oil, rose oil, rosehip oil, rosemary oil, rosewood oil, sage oil, sandalwood oil, sassafras oil, spearmint oil, tangerine oil, tea tree oil, thyme oil, tsuga oil, valerian oil, vanilla oil, wintergreen oil, ylang-ylang oil, one or more fractions thereof, or a combination thereof.

15. The aziridinated triglyceride of claim 1 , wherein the aziridinated triglyceride is derived from an oil by a method comprising epoxidizing the oil, treating the epoxidized product with a substituted or unsubstituted (C 3 -C 50 )carboxylic acid including at least one aliphatic unsaturated carbon-carbon bond, and treating the (C 3 -C 50 )carboxylic acid-treated product with an aziridine having the structure:

16. The aziridinated triglyceride of claim 1 , wherein the aziridinated triglyceride is derived from soybean oil.

17. The aziridinated triglyceride of claim 1 , having the structure:

18. A polymer prepared by contacting the aziridinated triglyceride of claim 1 with a polycarboxylic acid crosslinker.

Assignees

• Univ Iowa State Res Found Inc

Inventors

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

Classifications

• C08G63/6852

  derived from hydroxy carboxylic acids · CPC title

• C07D405/12 Primary

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

• C08G73/02

  Polyamines · CPC title