# US 10,501,448 B2 · Aziridinated triglycerides and polymers formed therefrom

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- Number: US 10,501,448 B2
- Document ID: US10501448B2
- Status: Granted
- Kind: B2
- Application number: 16/042,565
- Filed: 2018-07-23
- Published: 2018-11-15
- Granted: 2019-12-10
- Earliest claimed: 2015-04-06
- Assignees: Iowa State University Research Foundation, Inc.
- Applicants: Iowa State University Research Foundation, Inc.
- Inventors: Ruqi Chen; Jason Shih-Hao Chen; Chaoqun Zhang; Michael Richard Kessler
- Web page: https://patentgrep.com/patent/US10501448B2

## CPC

- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C08G 63/6852: {derived from hydroxy carboxylic acids}
- C08G 73/02: Polyamines
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## 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.

## Claims

### Claim 1

A polymer comprising a plurality of units of Formula (I):
wherein
R1, R2, and R3 are each independently a substituted or unsubstituted (C1-C50)hydrocarbyl and at least one of R1, R2, and R3 is interrupted or terminated by the A end of at least one -AZP— group having the structure:
at each occurrence, Ll is independently a substituted or unsubstituted (C2-C50)hydrocarbyl interrupted or terminated with 0, 1, 2, or 3 groups independently chosen from —O—, —S—, and substituted or unsubstituted —NH—,
at each occurrence, R4, R5, R6, and R7 are independently chosen from —H and substituted or unsubstituted (C1-C10)hydrocarbyl interrupted or terminated with 0, 1, 2, or 3 groups independently chosen from —O—, —S—, and substituted or unsubstituted —NH—,
at each occurrence, Rb is independently a substituted or unsubstituted (C1-C50)hydrocarbyl having a valence of z+1, wherein Rb is interrupted or terminated by 0, 1, 2, or 3 groups independently chosen from —O—, —S—, substituted or unsubstituted —NH—, and —(O—(C2-C3)alkylene)n—, wherein n is about 1 to about 10,000 and wherein the (C2-C3)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 R1, R2, or R3 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).

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

The polymer of claim 1, wherein each of R1, R2, and R3 have no more than one -AZP— group.

### Claim 7 (depends on 1)

The polymer of claim 1, wherein at least one of R1, R2, and R3 is interrupted or terminated by at least two -AZP— groups.

### Claim 8 (depends on 1)

The polymer of claim 1, wherein R1, R2, and R3 are each independently a substituted or unsubstituted (C10-C50)hydrocarbyl and each of R1, R2, and R3 is interrupted or terminated by at least one -AZP—group.

### Claim 9 (depends on 1)

The polymer of claim 1, wherein R1, R2, and R3 are each independently unsubstituted (C1-C50)alkane; unsubstituted (C1-C50)alkane interrupted or terminated with at least one -AZP— group, or unsubstituted (C1-C50)alkane substituted with 0, 1, 2, 3, 4, or 5 epoxy groups.

### Claim 10 (depends on 1)

The polymer of claim 1, wherein R1, R2, and R3 are each independently an unsubstituted (C1-C50)alkane or unsubstituted (C1-C50)alkane interrupted or terminated with at least one -AZP— group.

### Claim 11 (depends on 1)

The polymer of claim 1, wherein at each occurrence, Ll is independently an unsubstituted (C2-C10)alkanylene.

### Claim 12 (depends on 1)

The polymer of claim 1, wherein at each occurrence, R4, R5, R6, and R7 are —H or unsubstituted (C1-C10)hydrocarbyl.

### Claim 13 (depends on 1)

The polymer of claim 1, wherein at each occurrence, R5, R6, and R7 are —H.

### Claim 14 (depends on 1)

The polymer of claim 1, wherein at each occurrence, R5, R6, and R7 are —H, and R4 is unsubstituted (C1-C10)hydrocarbyl.

### Claim 15 (depends on 1)

The polymer of claim 1, wherein at each occurrence, R5, R6, and R7 are —H, and R4 is unsubstituted (C1-C5)alkyl.

### Claim 16 (depends on 1)

The polymer of claim 1, wherein Rb 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.

### Claim 17 (depends on 1)

The polymer of claim 1, wherein Rb 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 (C5-C10)cycloalkyl and (C2-C10)heterocyclyl,
m and n are each independently 1-8, and
at each occurrence R′ is independently chosen from substituted or unsubstituted (C2-C10)hydrocarbylene.

### Claim 18 (depends on 1)

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

### Claim 19 (depends on 1)

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

### Claim 20 (depends on 1)

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, 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.