Granted Patent B2

US 9,067,878 · App. 13/327,655 · Granted Jun 30, 2015

Abstract

Claims (158)

1. 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 R 1 , R 2 , R 3 , R 4 , and R 5 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 R 1 , R 2 , R 3 , R 4 , and R 5 is —X—R c , wherein:

(F) —X— is a linking group between R c and the aromatic group, wherein —X— is selected from the group consisting of

(i) —O—;

(ii) —S—;

(iii) —SO—;

(iv) —SO 2 —;

(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) R c 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 R 1 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 R 1 is not —COOH or R c is not

wherein n is 8 to 10; and

(4) when the compound is of the formula

either R 1 is not —COOH or R c 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.

2. 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.

3. 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.

4. A composition according to claim 1 wherein the organic liquid solvent is 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.

5. A composition according to claim 1 wherein the organic liquid solvent is:

(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.

6. A composition according to claim 1 wherein exactly one of R 1 , R 2 , R 3 , R 4 , and R 5 is —X—R c .

7. A composition according to claim 1 wherein exactly two of R 1 , R 2 , R 3 , R 4 , and R 5 are each, independently of the other, an —X—R c group.

8. A composition according to claim 1 wherein exactly one of R 1 , R 2 , R 3 , R 4 , and R 5 is —X—R c and exactly one of R 1 , R 2 , R 3 , R 4 , and R 5 is —COOH.

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

or mixtures thereof, R 1 , R 3 , and R 5 are each hydrogen atoms, R 2 is —X 1 —R c1 , and R 4 is —COOH or —X 2 —R c2 , wherein X 1 and X 2 have the same definition as X and can be either the same as or different from each other and R c1 and R c2 have the same definition as R c and can be either the same as or different from each other.

10. A composition according to claim 1 wherein R c is:

(a) a linear unsubstituted alkyl group of the formula —(CH 2 ) n CH 3 , 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; or

(e) a multi-branched unsubstituted alkyl group of the formula

wherein q is an integer and r is an integer.

11. A composition according to claim 1 wherein the alkylated aromatic acid is

12. 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.

13. A composition according to claim 12 wherein the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 1% by weight.

14. 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 R 1 , R 2 , R 3 , R 4 , and R 5 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 R 1 , R 2 , R 3 , R 1 , and R 5 is —X—R c , wherein:

(F) —X— is a linking group between R c and the aromatic group, wherein —X— is selected from the group consisting of

(i) —O—;

(ii) —S—;

(iii) —SO—;

(iv) —SO 2 —;

(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) R c 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 R 1 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 R 1 is not —COOH or R c is not

wherein n is 8 to 10; and

(4) when the compound is of the formula

either R 1 is not —COOH or R c 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.

15. 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 R c is:

(i) a linear unsubstituted alkyl group of the formula —(CH 2 ) n CH 3 , 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 R c is a linear unsubstituted alkyl group of the formula —(CH 2 ) n CH 3 , n is not 9, 10, or 11, wherein the organogel exhibits a gel-to-sol transition temperature of from about 65° C. to about 110° C.

16. A composition according to claim 15 wherein:

(a) the alkylated aromatic acid compound is present in the organic liquid in an amount of no more than about 5% by weight.

Assignments (8)