US 9,067,878 B2Granted

Organogel compositions comprising alkylated aromatic acids

AssigneeXerox Corporation

InventorsDarren A. Makeiff, Rina Carlini

Life of this patent

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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.

Claims16

Dependent claims

A composition comprising an organogel consisting of a) an alkylated aromatic acid and b) an organic liquid solvent entrapped within the organogel wherein the liquid is rigidified:

wherein the alkylated aromatic acid compound is of the formula
or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, is:
(A) hydrogen atoms;
—COOH;
(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, wherein —X— is selected from the group consisting of
(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—;
(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—;
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
wherein alkylated aromatic acid compounds self-assemble in the presence of the organic solvent to form the organogel, wherein the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.

53 more elements

A composition comprising an organogel consisting of a) an alkylated aromatic acid and b) an organic liquid solvent entrapped within the organogel wherein the liquid is rigidified:

wherein the alkylated aromatic acid compound is of the formula
or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, is:
(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, R1, and R5 is —X—Rc, wherein:
(F) —X— is a linking group between Rc and the aromatic group, wherein —X— is selected from the group consisting of
(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—;
(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—;
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, 0, 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;
wherein the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 5% by weight;
wherein the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.;
and
wherein alkylated aromatic acid compounds self-assemble in the presence of the organic solvent to form the organogel.

54 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/327,655Filed 15 Dec 2011
Published: US 2013/0158135 A120 Jun 2013
Granted: 30 Jun 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07C 63/04
Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings: monocyclic monocarboxylic acids
C07C 63/15
Monocyclic dicarboxylic acids: all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
C07C 233/54
With the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring:…
C07C 275/42
Having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton: being further substituted by…

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US 2013/0158135 A1Pre-grant publication · published 20 Jun 2013
US 9,067,878 B2This patent

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Abstract

A composition comprising an organogel consisting of a) an alkylated aromatic acid and b) an organic liquid solvent entrapped within the organogel wherein the liquid is rigidified:

wherein the alkylated aromatic acid compound is of the formula
or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, is:
(A) hydrogen atoms;
—COOH;
(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, wherein —X— is selected from the group consisting of
(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—;
(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—;
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
wherein alkylated aromatic acid compounds self-assemble in the presence of the organic solvent to form the organogel, wherein the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.

53 more elements

Facts

Application

13/327,655Filed 15 Dec 2011

Published

US 2013/0158135 A120 Jun 2013

Granted

30 Jun 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07C 63/04
Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings: monocyclic monocarboxylic acids
C07C 63/15
Monocyclic dicarboxylic acids: all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
C07C 233/54
With the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring:…
C07C 275/42
Having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton: being further substituted by…