# US 2013/0158135 A1 · Organogel Compositions Comprising Alkylated Aromatic Acids

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- Number: US 2013/0158135 A1
- Document ID: US20130158135A1
- Status: Published application
- Kind: A1
- Application number: 13/327,655
- Filed: 2011-12-15
- Published: 2013-06-20
- Earliest claimed: 2011-12-15
- Assignees: National Research Council of Canada; Xerox Corporation
- Inventors: Darren A. Makeiff; Rina Carlini
- Web page: https://patentgrep.com/patent/US20130158135A1

## CPC

- C07C 63/04: Monocyclic monocarboxylic acids
- C07C 63/15: all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
- C07C 233/54: having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
- C07C 275/42: being further substituted by carboxyl groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Disclosed is a composition comprising an organogel which comprises: (a) an alkylated aromatic acid compound of the formula or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, are hydrogen, alkyl, aryl, arylalkyl, or alkyl, provided that at least one of R1, R2, R3, R4, and R5 is —X—Rc, wherein —X— is a linking group between Rc and the aromatic group and Rc is alkyl; and (b) an organic liquid.

## Claims

### Claim 1

A composition comprising an organogel which comprises:
(a) an alkylated aromatic acid compound of the formula
or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, are:
(A) hydrogen atoms;
(B) alkyl groups, including substituted and unsubstituted alkyl groups, wherein hetero atoms either may or may not be present in the alkyl group;
(C) aryl groups, including substituted and unsubstituted aryl groups, wherein hetero atoms either may or may not be present in the aryl group;
(D) arylalkyl groups, including substituted and unsubstituted arylalkyl groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the arylalkyl group; or
(E) alkylaryl groups, including substituted and unsubstituted alkylaryl groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the alkylaryl group;
provided that at least one of R1, R2, R3, R4, and R5 is —X—Rc, wherein:
(F) —X— is a linking group between Rc and the aromatic group; and
(G) Rc is an alkyl group, including substituted and unsubstituted alkyl groups, wherein hetero atoms either may or may not be present in the alkyl group;
with the provisos that:
(1) when the compound is of the formula
either R1 is not
or n is not 9, 10, or 11;
(2) when the compound is of the formula
n is not 9, 10, or 11;
(3) when the compound is of the formula
either R1 is not —COOH or Rc is not
wherein n is 8 to 10; and
(4) when the compound is of the formula
either R1 is not —COOH or Rc is not
wherein n is from 8 to 10; and
(b) an organic liquid.

### Claim 2 (depends on 1)

A composition according to claim 1 wherein the alkylated aromatic acid compound is present in the organic liquid in an amount of at least about 0.05% by weight.

### Claim 3 (depends on 1)

A composition according to claim 1 wherein the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 20% by weight.

### Claim 4 (depends on 1)

A composition according to claim 1 wherein the organic liquid comprises a hydrocarbon, an alcohol, an amine, an ester, an ether, a mercaptan, an acid, a sulfone, an anhydride, a siloxane, a polymeric liquid, or a mixture thereof.

### Claim 5 (depends on 1)

A composition according to claim 1 wherein the organic liquid comprises:
(a) a linear, branched, or cyclic unsubstituted aliphatic hydrocarbon;
(b) a linear, branched, or cyclic substituted aliphatic hydrocarbon;
(c) an unsubstituted aromatic or heteroaromatic hydrocarbon;
(d) a substituted aromatic or heteroaromatic hydrocarbon;
(e) a linear, branched, or cyclic unsubstituted aliphatic alcohol;
(e) an aliphatic amine;
(f) an aromatic amine;
(g) an aliphatic ester;
(h) an aromatic ester;
(i) an aliphatic ether;
(j) an aromatic ether; or
(k) a mixture thereof.

### Claim 6 (depends on 1)

A composition according to claim 1 wherein exactly one of R1, R2, R3, R4, and R5 is —X—Rc.

### Claim 7 (depends on 1)

A composition according to claim 1 wherein exactly two of R1, R2, R3, R4, and R5 are each, independently of the other, an —X—Rc group.

### Claim 8 (depends on 1)

A composition according to claim 1 wherein exactly one of R1, R2, R3, R4, and R5 is —X—Rc and exactly one of R1, R2, R3, R4, and R5 is —COOH or —CONH2.

### Claim 9 (depends on 1)

A composition according to claim 1 wherein the alkylated aromatic acid is of the formula
or mixtures thereof, R1, R3, and R5 are each hydrogen atoms, R2 is —X1—Rc1, and R4 is —COOH or —X2—Rc2, wherein X1 and X2 have the same definition as X and can be either the same as or different from each other and Rc1 and Rc2 have the same definition as Rc and can be either the same as or different from each other.

### Claim 10 (depends on 1)

A composition according to claim 1 wherein Rc is:
(a) a linear unsubstituted alkyl group of the formula —(CH2)nCH3, wherein n is an integer;
(b) a branched unsubstituted alkyl group of the formula
wherein m is an integer and p is an integer;
(c) a branched unsubstituted alkyl group of the formula
wherein s is an integer and t is an integer;
(d) a branched unsubstituted alkyl group of the formula
wherein u is an integer and v is an integer;
(e) a multi-branched unsubstituted alkyl group of the formula
wherein q is an integer and r is an integer;
or mixtures thereof.

### Claim 11 (depends on 1)

A composition according to claim 1 wherein —X— is:
(i) —O—;
(ii) —S—;
(iii) —SO—;
(iv) —SO2—;
(v) —NH—(C═O)—;
(vi) —(C═O)—NH—;
(vii) —NH—(C═S)—;
(viii) —(C═S)—NH—;
(ix) —NH—;
(x) —NH—(C═O)—NH—;
(xi) —NH—(C═S)—NH—;
(xii) —NH—(C═O)—O—;
(xiii) —O—(C═O)—NH—;
(xiv) —NH—(C═S)—O—;
(xv) —S—(C═O)—NH—;
(xvi) —NH—(C═S)—O—;
(xvii) —NH—(C═S)—S—;
(xviii) —O—(C═S)—NH—;
(xix) —S—(C═S)—NH—;
(xx) —(C═O)—O—;
(xxi) —(C═O)—S—;
(xxii) —O—(C═O)—;
(xxiii) —S—(C═O)—;
(xxiv) —(C═S)—O—;
(xxv) —(C═S)—S—;
(xxvi) —O—(C═S)—;
(xxvii) —S—(C═S)—;
(xxviii) —O—(C═O)—O—;
(xxix) —O—(C═S)—O—; or
(xxx) a combination thereof.

### Claim 12 (depends on 1)

A composition according to claim 1 wherein the alkylated aromatic acid is of the formula
wherein R1′ has the same definition as R1 and can be either the same as or different from R1, R2′ has the same definition as R2 and can be either the same as or different from R2, and Rd is a difunctional moiety that bridges the aromatic acid groups.

### Claim 13 (depends on 1)

A composition according to claim 1 wherein the alkylated aromatic acid is of the formula

### Claim 14 (depends on 1)

A composition according to claim 1 wherein the alkylated aromatic acid is
or mixtures thereof.

### Claim 15 (depends on 1)

A composition according to claim 1 wherein the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.

### Claim 16 (depends on 1)

A composition according to claim 1 wherein:
(a) the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 5% by weight; and
(b) the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.

### Claim 17 (depends on 16)

A composition according to claim 16 wherein the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 1% by weight.

### Claim 18

A composition comprising an organogel which comprises:
(a) an alkylated aromatic acid compound of the formula
or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, are:
(A) hydrogen atoms;
(B) alkyl groups, including substituted and unsubstituted alkyl groups, wherein hetero atoms either may or may not be present in the alkyl group;
(C) aryl groups, including substituted and unsubstituted aryl groups, wherein hetero atoms either may or may not be present in the aryl group;
(D) arylalkyl groups, including substituted and unsubstituted arylalkyl groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the arylalkyl group; or
(E) alkylaryl groups, including substituted and unsubstituted alkylaryl groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the alkylaryl group;
provided that at least one of R1, R2, R3, R4, and R5 is —X—Rc, wherein:
(F) —X— is a linking group between Rc and the aromatic group; and
(G) Rc is an alkyl group, including substituted and unsubstituted alkyl groups, wherein hetero atoms either may or may not be present in the alkyl group;
with the provisos that:
(1) when the compound is of the formula
either R1 is not
or n is not 9, 10, or 11;
(2) when the compound is of the formula
n is not 9, 10, or 11;
(3) when the compound is of the formula
either R1 is not —COOH or Rc is not
wherein n is 8 to 10; and
(4) when the compound is of the formula
either R1 is not —COOH or Rc is not
wherein n is from 8 to 10; and
(b) an organic liquid;
wherein the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 5% by weight; and
wherein the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.

### Claim 19

A composition comprising an organogel which comprises:
(a) an alkylated aromatic acid compound of the formula
or mixtures thereof, wherein Rc is:
(i) a linear unsubstituted alkyl group of the formula —(CH2)nCH3, wherein n is an integer;
(ii) a branched unsubstituted alkyl group of the formula
wherein m is an integer and p is an integer;
(iii) a branched unsubstituted alkyl group of the formula
wherein s is an integer and t is an integer;
(iv) a branched unsubstituted alkyl group of the formula
wherein u is an integer and v is an integer;
(v) a multi-branched unsubstituted alkyl group of the
formula
wherein q is an integer and r is an integer;
or mixtures thereof; with the proviso that when the compound is of the formula
and Rc is a linear unsubstituted alkyl group of the formula —(CH2)nCH3, n is not 9, 10, or 11; and
(b) an organic liquid.

### Claim 20 (depends on 19)

A composition according to claim 19 wherein:
(a) the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 5% by weight; and
(b) the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.