IP Library Patent Application 17560026
Patent Application
App. No. 17/560,026

ELASTOMER GEL FROM EPOXIDIZED VEGETABLE OIL AND USES THEREOF

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Patent No.
US None
App. No.
17/560,026
Abstract

The present disclosure relates to gel compositions comprising the reaction product of at least one epoxidized molecule and at least one crosslinker, which has the benefit of compatibility with personal care components and the resulting personal care formulations. The present disclosure also relates to methods of preparing gel compositions.

Claims (72)

1 . An elastomer comprising the reaction product of at least one epoxidized molecule and at least one crosslinker.

2 . The elastomer of claim 1 , wherein the at least one epoxidized molecule is a compound of formula (I)

wherein

R 1 is C 6 -C 100,000 alkyl group, C 6 -C 100,000 heteroalkyl group, C 6 -C 100,000 alkene group, C 6 -C 100,000 heteroalkene group, C 6 -C 100,000 alkyne group, C 6 -C 100,000 heteroalkyne group, C 6 -C 100,000 cyclic group, or C 6 -C 100,000 heterocyclic group;

R 2 is hydrogen, C 1 -C 100,000 alkyl group, C 1 -C 100,000 heteroalkyl group, C 2 -C 100,000 alkene group, C 2 -C 100,000 heteroalkene group, C 2 -C 100,000 alkyne group, C 2 -C 100,000 heteroalkyne group, C 3 -C 100,000 cyclic group, or C 3 -C 100,000 heterocyclic group; and

m is an integer from 2 to 1,000.

3 . The elastomer of claim 1 , wherein the at least one epoxidized molecule is at least one epoxidized vegetable oil.

4 . The elastomer of claim 1 , wherein the at least one crosslinker is selected from the group consisting of:

(i) a carboxylic acid comprising the structure of formula (II)

wherein

R 3 is C 2 -C 200 alkyl group, C 2 -C 200 heteroalkyl group, C 2 -C 200 alkene group, C 2 -C 200 heteroalkene group, C 2 -C 200 alkyne group, C 2 -C 200 heteroalkyne group, C 3 -C 200 cyclic group, or C 2 -C 200 heterocyclic group; and

n is an integer from 2 to 10;

(ii) an anhydride comprising the structure of formula (III)

wherein

R 4 is C 2 -C 200 alkyl group, C 2 -C 200 heteroalkyl group, C 2 -C 200 alkene group, C 2 -C 200 heteroalkene group, C 2 -C 200 alkyne group, C 2 -C 200 heteroalkyne group, C 3 -C 200 cyclic group, or C 2 -C 200 heterocyclic group;

(iii) an amine comprising the structure of formula (IV)

wherein

R 5 is C 2 -C 200 alkyl group, C 2 -C 200 heteroalkyl group, C 2 -C 200 alkene group, C 2 -C 200 heteroalkene group, C 2 -C 200 alkyne group, C 2 -C 200 heteroalkyne group, C 3 -C 200 cyclic group, or C 2 -C 200 heterocyclic group; and

p is an integer from 2 to 10;

(iv) an alcohol comprising the structure of formula (V)

wherein

R 6 is C 2 -C 200 alkyl group, C 2 -C 200 heteroalkyl group, C 2 -C 200 alkene group, C 2 -C 200 heteroalkene group, C 2 -C 200 alkyne group, C 2 -C 200 heteroalkyne group, C 3 -C 200 cyclic group, or C 2 -C 200 heterocyclic group;

q is an integer from 2 to 10;

(v) a hydroxyl carboxylic acid comprising the structure of formula (VI)

wherein

R 7 is C 1 -C 200 alkyl group, C 1 -C 200 heteroalkyl group, C 2 -C 200 alkene group, C 2 -C 200 heteroalkene group, C 2 -C 200 alkyne group, C 2 -C 200 heteroalkyne group, C 3 -C 200 cyclic group, or C 2 -C 200 heterocyclic group;

(vi) a amine carboxylic acid comprising the structure of formula (VII)

wherein

R 8 is C 1 -C 200 alkyl group, C 1 -C 100,000 heteroalkyl group, C 2 -C 200 alkene group, C 2 -C 200 heteroalkene group, C 2 -C 200 alkyne group, C 2 -C 200 heteroalkyne group, C 3 -C 200 cyclic group, or C 2 -C 200 heterocyclic group;

and combinations thereof.

5 . The elastomer of claim 4 , wherein the at least one crosslinker is a carboxylic acid comprising the structure of formula (II) wherein R 2 is C 2 -C 60 alkyl group, C 2 -C 60 heteroalkyl group, C 2 -C 60 alkene group, or C 2 -C 60 heteroalkene group; and n is an integer from 2 to 6.

6 . The elastomer of claim 4 , wherein the carboxylic acid is selected from the group consisting of citric acid, isocitric acid, aconitic acid, propane-1,2,3-tricarboxylic acid, trimesic acid, carballylic acid, C 54 trimer acid, mellitic acid, reaction product of ricinoleic acid and sebacic acid, reaction product of C 36 dimer acid and C 36 dimer diol, and combinations thereof.

7 . The elastomer of claim 5 , wherein the carboxylic acid is a dicarboxylic acid.

8 . The elastomer of claim 7 , wherein the dicarboxylic acid is selected from the group consisting of malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, hexadecanedioic acid, C 21 dimer acid, C 36 dimer acid, hydrogenated C 36 dimer acid, aspartic acid, glutamic acid, tartaric acid, malic acid, and combinations thereof. In a further aspect, the dicarboxylic acid may be selected from the group consisting of malonic acid, succinic acid, adipic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, C 21 dimer acid, C 36 dimer acid, hydrogenated C 36 dimer acid, and combinations thereof.

9 . The elastomer of claim 5 , wherein the at least one crosslinker is an alcohol comprising the structure of formula (V) wherein R 6 is C 2 -C 200 alkyl group, C 2 -C 200 heteroalkyl group, C 2 -C 200 alkene group, or C 2 -C 200 heteroalkene group; and q is an integer from 2 to 6.

10 . The elastomer of claim 9 , wherein the alcohol is a diol.

11 . The elastomer of claim 10 , wherein the diol is selected from the group consisting of ethyleneglycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 1,2-hexanediol, 1,5-hexanediol, 1,6-hexanediol, C 36 dimer diol, hydrogenated C 36 dimer diol, and combinations thereof.

12 . The elastomer of claim 1 prepared by reacting at least one epoxidized molecule and at least one crosslinker in the presence of a first solvent thereby forming a crosslinking polymer structure.

13 . The elastomer of claim 12 , wherein the solvent is selected from the group consisting of a triglyceride solvent, a mono-ester solvent, a di-ester solvent, a citrate ester solvent, an ether solvent, a carbonate solvent, a hydrocarbon solvent, a silicone solvent, and combinations thereof.

14 . The elastomer of claim 13 , wherein the triglyceride solvent comprising the compound of formula (VIII)

wherein

R 11 , R 12 , and R n are independently C 1 -C 35 alkyl group, C 1 -C 35 heteroalkyl group, C 2 -C 35 alkene group, or C 2 -C 35 heteroalkene group.

15 . The elastomer of claim 13 , wherein the triglyceride solvent is selected from the group consisting of caprylic/capric triglyceride, triheptanoin, corn oil, soybean oil, olive oil, rape seed oil, cotton seed oil, coconut oil, almond oil, argon oil, rosehip oil, black seed oil, grape seed oil, avocado oil, apricot kernel oil, geranium oil, lavender oil, rosehip oil, macadamia oil, eucalyptus oil, sardine oil, herring oil, safflower oil, linseed oil, sunflower oil, olive oil, canola oil, sesame oil, cottonseed oil, palm oil, rapeseed oil, tung oil, fish oil, peanut oil, cuphea oil, milkweed oil, salicornia oil, whale oil, castor oil, and combinations thereof.

16 . The elastomer of claim 13 , wherein the mono-ester solvent is a compound of formula (IX)

wherein

R 14 is C 1 -C 35 alkyl group, C 1 -C 35 heteroalkyl group, C 2 -C 35 alkene group, or C 2 -C 35 heteroalkene group; and

R 15 is H, C 1 -C 35 alkyl group, C 1 -C 35 heteroalkyl group, C 2 -C 35 alkene group, or C 2 -C 35 heteroalkene group.

17 . The elastomer of claim 13 , wherein the mono-ester solvent is selected from the group consisting of coco-caprylate/caprate, coco-caprylate, coco-caprate, jojoba oil, jojoba esters, isopropyl jojobate, ethyl macadamiate, isoamyl laurate, heptyl undecylenate, methylheptyl isostearate, isostearyl isostearate, glyceryl ricinoleate, isostearyl palmitate, myristyl myristate, octyldodecyl myristate, octyldodecyl hydroxystearate, butyl myristate, ethylhexyl cocoate, ethylhexyl palmitate, ethylhexyl stearate, butyl stearate, decyl oleate, isocetyl behenate, isocetyl myristate, isocetyl palmitate, isocetyl stearate, isodecyl oleate, isopropyl isostearate, isopropyl myristate, isopropyl palmitate, oleyl oleate, propylene glycol laurate, octydodecyl erucate, Cu-CD alkyl lactate, C 12 -C 15 alkyl lactate, isostearyl lactate, glycereth-5 lactate, lauryl lactate, myristyl lactate, oleyl lactate, laureth-2 benzoate, C 12 -C 15 alkyl benzoate, C 12 -C 15 pareth-3 benzoate, dipropylene glycol benzoate, isodecyl salicylate, C 12 -C 15 alkyl salicylate, tridecyl salicylate, ethylhexyl isononanoate, cetyl ethylhexanoate, isononyl isononanoate, isodecyl ethylhexanoate, isodecyl isononanoate, tridecyl ethylhexanoate, isotridecyl isononanoate, isostearyl isononanoate, cetearyl isononanoate, laureth-2 ethylhexanoate, cetearyl ethylhexanoate, isodecyl neopentanoate, isostearyl neopentanoate, nyristyl neopentanoate, isostearyl behenate, octyldodecyl neopentanoate, tridecyl neopentanoate, and combinations thereof.

18 . The elastomer of claim 13 , wherein the di-ester solvent is a compound of formula (X), formula (XI), or formula (XII)

wherein

R 16 is C 1 -C 35 alkyl group, C 1 -C 35 heteroalkyl group, C 2 -C 35 alkene group, or C 2 -C 35 heteroalkene group; and

R 17 and V are independently H, C 1 -C 35 alkyl group, C 1 -C 35 heteroalkyl group, C 2 -C 35 alkene group, or C 2 -C 35 heteroalkene group.

19 . The elastomer of claim 13 , wherein the citrate ester is a compound of formula (XIII)

wherein

R 19 , R 20 , R 21 , and R 22 are independently H, C 1 -C 35 alkyl group, C 1 -C 35 heteroalkyl group, C 2 -C 35 alkene group, or C 2 -C 35 heteroalkene group.

20 . The elastomer of claim 13 , wherein the ether solvent is a compound of formula (XIV)

wherein

R 23 and R 24 are independently H, C 2 -C 20 alkyl group, C 2 -C 20 heteroalkyl group, C 2 -C 20 alkene group, or C 2 -C 20 heteroalkene group.

21 . The elastomer of claim 13 , wherein the ether solvent is selected from the group consisting of dicaprylyl ether, didecyl ether, panthenyl ethyl ether, dicetyl ether, dimyristyl ether, distearyl ether, distearyl ether, dilauryl ether, and combinations thereof.

22 . The elastomer of claim 13 , wherein the carbonate solvent is a compound of formula (XV)

wherein

R 25 and R 26 are independently H, C 2 -C 20 alkyl group, C 2 -C 20 heteroalkyl group, C 2 -C 20 alkene group, or C 2 -C 20 heteroalkene group.

23 . The elastomer of claim 13 , wherein the hydrocarbon solvent is selected from the group consisting of farnesene, hydrogenated farnesene, coconut alkanes, coconut/palm kernel alkanes, C 9 -C 12 alkane, C 10 -C 13 alkane, alkane, C 12 -C 17 alkane, C 13 -C 15 alkane, C 14 -C 17 alkane, C 14 -C 19 alkane, C 14 -C 20 alkane, C 14 -C 22 alkane, C 15 -C 19 alkane, C 21 -C 28 alkane, C 17 -C 23 alkane, C 9 -C 12 isoalkane, C 9 -C 13 isoalkane, C 9 -C 14 isoalkane, C 9 -C 16 isoalkane, C 10 -C 11 isoalkane, C 10 -C 12 isoalkane, C 10 -C 13 isoalkane, isoalkane, C 11 -C 13 isoalkane, C 11 -C 14 isoalkane, C 12 -C 14 isoalkane, Cu-Cis isoalkane, C 12 -C 20 isoalkane, C 13 -C 14 isoalkane, C 13 -C 16 isoalkane, C 14 -C 16 isoalkane, C 15 -C 19 isoalkane, diethylhexylcyclohexane, undecane, tridecane, tetradecane, pentadecane, hexadecane, octadecane, docosane, squalane, hydrogenated polyisobutene, polybutene, hydrogenated polydecene, hydrogenated didecene, mineral oil, liquidum, petrolatum, dodecane, isohexadecane, isododecane, isoeicosane, and combinations thereof.

24 . A composition comprising the elastomer of claim 1 .

25 . The composition of claim 24 , wherein the composition is a gel.

26 . A gel produced by combining an elastomer of claim 1 with one or more solvents and processed by homogenization.

27 . A personal care formulation comprising the gel of claim 26 .

28 . The personal care formulation of claim 27 , wherein the personal care formulation is a personal care application selected from the group consisting of a deodorant, an antiperspirant, a skin cream, a facial cream, a hair shampoo, a hair conditioner, a mousse, a hair styling gel, a hair spray, a protective cream, a lipstick, a facial foundations, blushes, makeup, and mascara, a skin care lotion, a moisturizer, a facial treatment, a personal cleanser, a facial cleanser, a bath oil, a perfume, a shaving cream, a pre-shave lotion, an after-shave lotion, a cologne, a sachet, and a sunscreen.

29 . A method of preparing an elastomer of claim 1 comprising reacting at least one epoxidized molecule and at least one crosslinker in the presence of a first solvent thereby forming a crosslinking polymer structure.

30 . The method of claim 29 , wherein the method further comprises:

i. combining the crosslinking polymer structure in a second solvent thereby forming a swollen crosslinking polymer structure; and

ii. subjecting the swollen crosslinking polymer structure to shear force thereby forming the gel.

Assignments (5)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 14, 2022
From: QIN, XU; FALK, BENJAMIN; TAMAMI, MANA; GALABURA, YURIY; PAWAR, AMAR; WAGNER, ROLAND
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 061096/0210 →