Colorant compositions
View Patent ↗Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R′ is an aromatic- or heteroaromatic-containing group, each R a , independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
1. A compound comprising two or more moieties of the formula
wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R′ is an aromatic- or heteroaromatic-containing group, each R a , independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units and is at least about 2, wherein said moieties each contain no —OH groups, —SH groups, or primary or secondary amino groups, said moieties being linked by a central atom or group of atoms.
2. A compound according to claim 1 wherein R is an alkyl group with at least one carbon atom and with no more than about 50 carbon atoms, an aryl group with at least about 5 carbon atoms and with no more than about 50 carbon atoms, an arylalkyl group with at least about 6 carbon atoms and with no more than about 50 carbon atoms, or an alkylaryl group with at least about 6 carbon atoms and with no more than about 50 carbon atoms.
3. A compound according to claim 1 wherein R is ethyl.
4. A compound according to claim 1 wherein R′ is an aryl group, an arylalkyl group, an alkylaryl group.
5. A compound according to claim 1 wherein R′ is an aryl group with at least about 2 carbon atoms and with no more than about 60 carbon atoms, an arylalkyl group with at least about 3 carbon atoms and with no more than about 60 carbon atoms, or an alkylaryl group with at least about 3 carbon atoms and with no more than about 60 carbon atoms.
6. A compound according to claim 1 wherein R′ is selected from the group consisting of (1) thiophene derivatives of the formula
(2) benzothiazole derivatives of the formula
(3) benzoisothiazole derivatives of the formulae
(4) thiadiazole derivatives of the formulae
(5) benzene derivatives of the formula
and (6) imidazole derivatives of the formula
wherein R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 each, independently of the other, is a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a sulfonamidoalkyl group, a sulfonamidoaryl group, a sulfonamidoarylalkyl group, a sulfonamidoalkylaryl, group, a sulfonamidodialkyl group, a sulfonamidodiaryl group, a sulfonamidodiarylalkyl group, a sulfonamidodialkylaryl group, an amidoalkyl group, an amidoaryl group, an amidoarylalkyl group, an amidoalkylaryl group, an amidodialkyl group, an amidodiaryl group, an amidodiarylalkyl group, an amidodialkylaryl group, an amidodiarylalkyl group, a thioalkyl group, a thioaryl group, a thioarylalkyl group, a thioalkylaryl group, an ester group of the formula
wherein R″ is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, a ketone group of the formula
wherein R′″ is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, a sulfone group of the formula —SO 2 R″″ wherein R″″ is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group.
7. A compound according to claim 1 wherein R′ is (a) of the formula
wherein A, G, and J each, independently of the others, is a carbon atom or a hetero atom, R 1 , R 2 , and R 3 each, independently of the other, is a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a sulfonamidoalkyl group, a sulfonamidoaryl group, a sulfonamidoarylalkyl group, a sulfonamidoalkylaryl, group a sulfonamidodialkyl group, a sulfonamidodiaryl group, a sulfonamidodiarylalkyl group, a sulfonamidodialkylaryl group, an amidoalkyl group, an amidoaryl group, an amidoarylalkyl group, an amidoalkylaryl group, an amidodialkyl group, an amidodiaryl group, an amidodiarylalkyl group, an amidodialkylaryl group, an amidodiarylalkyl group, a thioalkyl group, a thioaryl group, a thioarylalkyl group, a thioalkylaryl group, an ester group of the formula
wherein R″ is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, a ketone group of the formula
wherein R′″ is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, a sulfone group of the formula —SO 2 R″″ wherein R″″ is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group; (b) of the formula
wherein R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 each, independently of the others, can be selected from the same groups as R 1 , R 2 , and R 3 ; or (c) those of the formula
wherein R 10 , R 11 , R 12 , R 13 , and R 14 each, independently of the others, can be selected from the same groups as R 1 , R 2 , and R 3 .
8. A compound according to claim 1 wherein R′ is
9. A compound according to claim 1 wherein R′ is
10. A compound according to claim 1 wherein n is at least about 2 and wherein n is no more than about 18.
11. A compound according to claim 1 wherein n is no more than about 4.
12. A compound according to claim 1 wherein x is at least about 2 and wherein x is no more than about 100.
13. A compound according to claim 1 wherein x is at least about 5 and wherein x is no more than about 20.
14. A compound according to claim 1 wherein each R a , independently of the others, is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group with at least one carbon atom and with no more than about 25 carbon atoms, an alkoxy group with at least one carbon atom and with no more than about 25 carbon atoms, a nitrile group, a nitro group, an amide group of the formula
wherein R m is a hydrogen atom, an alkyl group with at least 1 carbon atom and with no more than about 50 carbon atoms, an aryl group with at least 5 carbon atoms and with no more than about 50 carbon atoms, an arylalkyl group with at least about 6 carbon atoms and with no more than about 50 carbon atoms, or an alkylaryl group with at least about 6 carbon atoms and with no more than about 50 carbon atoms, or a sulfonamide group of the formula
wherein R p is a hydrogen atom, an alkyl group with at least 1 carbon atom and with no more than about 50 carbon atoms, an aryl group with at least 5 carbon atoms and with no more than about 50 carbon atoms, an arylalkyl group with at least about 6 carbon atoms and with no more than about 50 carbon atoms, or an alkylaryl group with at least about 6 carbon atoms and with no more than about 50 carbon atoms.
15. A compound according to claim 1 wherein the moieties are linked by a group of atoms which is derived from an isocyanate.
16. A compound according to claim 15 wherein the isocyanate is a diisocyanate.
17. A compound according to claim 16 wherein the diisocyanate is isophorone diisocyanate; toluene diisocyanate; diphenylmethane-4,4′-diisocyanate; hydrogenated diphenylmethane-4,4′-diisocyanate; tetra-methyl xylene diisocyanate; hexamethylene-1,6-diisocyanate; napthylene-1,5-diisocyanate; 3,3′-dimethoxy-4,4′-biphenyldiisocyanate; 3,3′-dimethyl-4,4′-bimethyl-4,4′-biphenyldiisocyanate; phenylene diisocyanate; 4,4′-biphenyldiisocyanate; trimethylhexamethylene diisocyanate; tetramethylene xylene diisocyanate; 4,4′-methylenebis(2,6-diethylphenyl isocyanate); 1,12-d isocyanatododecane; 1,5-diisocyanato-2-methylpentane; 1,4-diisocyanatobutane; cyclohexylene diisocyanate; a uretidione dimer of hexamethylene-1,6-diisocyanate; or mixtures thereof.
18. A compound according to claim 15 wherein the isocyanate is a triisocyanate.
19. A compound according to claim 1 wherein the moieties are linked by a group of atoms which is a urethane.
20. A compound comprising two or more moieties of the formula
wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R′ is an aromatic- or heteroaromatic-containing group, each R a , independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said moieties each contain no —OH groups, —SH groups, or primary or secondary amino groups, said moieties being linked by a group of atoms which is an anhydride.
21. A compound according to claim 20 wherein the anhydride is a cyclic anhydride.
22. A compound according to claim 20 wherein the anhydride is 3,3′,4,4′-benzophenone tetracarboxylic dianhydride, 4,4′-(hexafluoroisopropylidine)-diphthalic anhydride, 1,2,4,5-benzenetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylicdianhydride, bicyclo[2,2,2]octo-7-ene-2,3,5,6-tetracarboxylicdianhydride, ethylenediaminetetraacetic dianhydride, diethylenetriaminepentaacetic dianhydride, or mixtures thereof.