Phase change inks
View Patent ↗Disclosed is a phase change ink comprising a phase change ink carrier and a colorant compound of the formula wherein X 1 , X 2 , and X 3 each, independently of the others, is —O—, —S—, —SO—, or —SO 2 —; R 1 , R 2 , and R 3 each, independently of the others, is alkyl, aryl, arylalkyl, or alkylaryl as further defined herein; and Z is halogen, —OR 4 , wherein R 4 is alkyl, aryl, arylalkyl, or alkylaryl as further defined herein, wherein R 5 is alkyl, aryl, arylalkyl, or alkylaryl as further defined herein, or wherein R 6 is alkyl, aryl, arylalkyl, or alkylaryl as further defined herein.
1. A phase change ink comprising:
(I) a phase change ink carrier; and
(II) a colorant compound of the formula
wherein:
(a) X 1 , X 2 , and X 3 each, independently of the others, is —O—, —S—, —SO—, or —SO 2 —;
(b) R 1 , R 2 , and R 3 each, independently of the others, is:
(1) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(2) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(3) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(4) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl; and
(c) Z is:
(1) halogen;
(2) —OR 4 , wherein R 4 is:
(A) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(B) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(C) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(D) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl;
(3)
wherein R 5 is:
(A) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(B) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(C) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(D) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl; or
(4)
wherein R 6 is:
(A) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(B) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(C) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(D) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl.
2. An ink according to claim 1 wherein the colorant compound is present in the ink in an amount of at least about 0.1% by weight of the ink.
3. An ink according to claim 1 wherein the colorant compound is present in the ink in an amount of no more than about 20% by weight of the ink.
4. An ink according to claim 1 wherein the carrier comprises a branched triamide.
5. An ink according to claim 4 wherein the branched triamide is of the formula
wherein x, y, and z each independently represent the number of propyleneoxy repeat units and x+y+z is from about 5 to about 6, and wherein p, q, and r are integers representing the number of repeat —(CH 2 )— units, wherein p, q, and r each, independently of the others, are from about 34 to about 40.
6. An ink according to claim 1 wherein the carrier comprises an amorphous component and a crystalline component.
7. An ink according to claim 1 wherein —X 1 —R 1 , —X 2 —R 2 , and —X 3 —R 3 are:
(a)
wherein m is an integer representing the number of repeat CH 2 units;
(b)
wherein q is an integer representing the number of repeat CH 2 units;
(c)
wherein p is an integer representing the number of repeat CH 2 units;
(d)
wherein n is an integer representing the number of repeat CH 2 units; or
(e) combinations thereof.
8. An ink according to claim 1 wherein —X 1 —R 1 , —X 2 —R 2 , and —X 3 —R 3 are each
or
9. An ink according to claim 1 wherein —X 1 —R 1 , —X 2 —R 2 , and —X 3 —R 3 are each
wherein n is an integer of from about 8 to about 50.
10. An ink according to claim 1 wherein Z is
or mixtures thereof.
11. An ink according to claim 1 wherein the colorant is of the formula
or mixtures thereof.
12. An ink according to claim 1 wherein the colorant has a L* value of at least about 40, and wherein the colorant has a L* value of no more than about 60.
13. An ink according to claim 1 wherein the colorant has a a* value of at least about 35, and wherein the colorant has a a* value of no more than about 53.
14. An ink according to claim 1 wherein the colorant has a b* value of at least about −24, and wherein the colorant has a b* value of no more than about −40.
15. An ink according to claim 1 wherein the colorant has a c* value of at least about 49, and wherein the colorant has a c* value of no more than about 60.
16. An ink according to claim 1 wherein the colorant has a solubility in the ink carrier of at least about 0.1 g/100 g at a temperature of from about 25° C. to about 130° C.
17. A phase change ink comprising:
(I) a phase change ink carrier; and
(II) a colorant compound of the formula
wherein:
(a) X 1 , X 2 , and X 3 each, independently of the others, is —O—, —S—, —SO—, or —SO 2 —;
(b) R 1 , R 2 , and R 3 each, independently of the others, is:
(1) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(2) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(3) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(4) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl; and
(c) Z is:
(1) halogen;
(2) —OR 4 , wherein R 4 is:
(A) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(B) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(C) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(D) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl;
(3)
wherein R 5 is:
(A) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(B) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(C) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(D) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl; or
(4)
wherein R 6 is:
(A) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(B) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(C) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(D) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl;
wherein the colorant has:
(i) a L* value of from about 40 to about 60;
(ii) a a* value of from about 35 to about 53;
(iii) a b* value of from about −24 to about −40; and
(iv) a c* value of from about 49 to about 60.
18. An ink according to claim 17 wherein —X 1 —R 1 , —X 2 —R 2 , and —X 3 —R 3 are:
(a)
wherein m is an integer representing the number of repeat CH 2 units;
(b)
wherein q is an integer representing the number of repeat CH 2 units;
(c)
wherein p is an integer representing the number of repeat CH 2 units;
(d)
wherein n is an integer representing the number of repeat CH 2 units; or
(e) combinations thereof.
19. An ink according to claim 17 wherein Z is
or mixtures thereof.
20. A phase change ink comprising:
(I) a phase change ink carrier comprising an amide compound; and
(II) a colorant compound, present in the ink in amount of from about 0.1% to about 20% by weight of the ink, of the formula
wherein:
(a) X 1 , X 2 , and X 3 each, independently of the others, is —O—, —S—, —SO—, or —SO 2 —;
(b) R 1 , R 2 , and R 3 each, independently of the others, is:
(1) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(2) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(3) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(4) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl; and
(c) Z is:
(1) halogen;
(2) —OR 4 , wherein R 4 is:
(A) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
(B) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;
(C) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or
(D) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl;
(3)
wherein R 5 is: alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl; or
(4)
wherein R 6 is: alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;
said ink having:
(i) a peak melting point of from about 50° C. to about 160° C.;
(ii) an onset melting point of from about 50° C. to about 75° C.;
(iii) a melt viscosity at the jetting temperature of from about 2 cps to about 30 cps.