Back to results
US 7,749,315 B2Granted
Phase change inks containing colorant compounds
AssigneeXerox Corporation
InventorsJeffrey H. Banning, Rina Carlini, James D. Mayo
Life of this patent
Estimating the term…
Abstract
Disclosed is a phase change ink composition comprising a phase change ink carrier and a compound of the formula and dimers thereof, wherein R, R2, X and Z are as described herein.
Claims39
A phase change ink composition comprising a phase change ink carrier and a compound of the formula
- comprising a dianthranilate moiety and an acetoacetamido moiety;
- wherein R is a substituent on the acetoacetamido moiety corresponding to a selected acetoacetamide precursor and wherein R is 2-ethylhexyl, dodecylaniline, Guerbet, or p-hydroxyethylanilino moiety;
- wherein substituent R and R′, if R′ is present, is a substituent on the acetoacetamido moiety corresponding to a selected acetoacetamide precursor on the acetoacetamido moiety and wherein R′, if R′ is present, is 2-ethylhexyl, dodecylaniline, Guerbet, or p-hydroxyethylanilino moiety;
- wherein the number of carbon atoms in R plus R2 is at least about 12;
- wherein R2 is (i) an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an alkylene group, including substituted and unsubstituted alkylene groups, and wherein hetero atoms either may or may not be present in the alkylene group, (iii) an arylene group, including substituted and unsubstituted arylene groups, and wherein hetero atoms either may or may not no be present in the arylene group (iv) an arylalkylene group, including substituted and unsubstituted arylalkylene groups, and wherein hetero atoms either may or may not be present in the arylalkylene group, (v) an alkylarylene group, including substituted and unsubstituted alkylarylene groups, and wherein hetero atoms either may or may not be present in the alkylarylene group, (vi) an alkyleneoxy group, including substituted and unsubstituted alkyleneoxy groups, and wherein hetero atoms either may or may not be present in the alkyleneoxy group, (vii) an aryleneoxy group, including substituted and unsubstituted aryleneoxy groups, and wherein hetero atoms either may or may not be present in the alkyleneoxy group, (viii) an arylalkyleneoxy group, including substituted and unsubstituted arylalkyleneoxy group, and wherein hetero atoms either may or may not be present in the arylalkyleneoxy group, (ix) an alkylaryleneoxy group, including substituted and unsubstituted alkylaryleneoxy groups, and wherein hetero atoms either may or may not be present in the alkylaryleneoxy group, (x) a polyalkyleneoxy group, (xi) a polyaryleneoxy group, (xii) a polyarylalkyleneoxy group, (xiii) polyalkylaryleneoxy group, (xiv) a heterocyclic group, (xv) a silylene group, (xvi) a siloxane group, (xvii) a polysilylene group, or (xviii) a polysiloxane group;
- wherein X and X′, if X′ is present, is a (i) direct bond, (ii) an oxygen atom, (iii) a nitrogen atom, (iv) a sulfur atom, (v) a group of the formula NR40 wherein R40 is a hydrogen atom, an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, an aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, an arylalkyl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atoms either may or may not be present in the arylalkyl group, or an alkylaryl group, including substituted and unsubstituted alkylaryl groups, and wherein hetero atoms either may or may not be present in the alkylaryl group, (vi) or a group of the formula CR50R60—;
- wherein R50 and R60 each, independently of the other, is a hydrogen atom, an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, an aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, an arylalkyl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atoms either may or may not be present in the arylalkyl group, or an alkylaryl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atoms either may or may not be present in the alkylaryl group, wherein two or more substituents can be joined together to for a ring, and wherein X and X′ can be the same as each other or different from each other;
- wherein Z and Z′ are each optionally present and if present are each independently selected from a (i) hydrogen atom, (n) a halogen atom, (iii) a nitro group, (iv) an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (v) aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, (vi) arylalkyl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atom either may or may not be present in the arylalkyl group, (vii) an alkylaryl group, including substituted and unsubstituted alkylaryl groups, and wherein hetero atoms either may or may not be present in the alkylaryl group, (viii) a group of the formula
- wherein R70 is an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, an aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, an arylalkyl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atoms either may or may not be present in the arylalkyl group, an alkylaryl group, including substituted and unsubstituted alkylaryl groups, and wherein hetero atoms either may or may not be present in the alkylaryl group, an alkoxy group, including substituted and unsubstituted arylalkyleneoxy groups, and wherein hetero atoms either may or may not be present in the alkoxy group, an aryloxy group, including substituted and unsubstituted aryloxy group, and wherein hetero atoms either may or may not be present in the aryloxy group, an arylalkyloxy group, including substituted and unsubstituted arylalkyloxy groups, and wherein hetero atoms either may or may not be present in the arylalkyloxy group, an alkylaryloxy group, including substituted and unsubstituted alkylaryloxy groups, and wherein hetero atoms either may or may not be present in the alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a heterocyclic group, as silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, (ix) a sulfonyl group of the formula —SO2R80 wherein R80 is a hydrogen atom, an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, an aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, an arylalkyl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atoms either may or may not be present in the arylalkyl group, an alkylaryl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atoms either may or may not be present in the alkylaryl group, an alkoxy group, including substituted and unsubstituted alkoxy groups, and wherein hetero atoms either may or may not be present in the alkoxy group, an aryloxy group, including substituted and unsubstituted aryloxy groups, and wherein hetero atoms either may or may not be present in the aryloxy group, an arylalkyloxy group, including substituted and unsubstituted arylalkyloxy groups, and wherein hetero atoms either may or may not be present in the arylalkyloxy group, an alkylaryloxy group, including substituted and unsubstituted alkylaryloxy groups, and wherein hetero atoms either may or may not be present in the alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, or (x) a phosphoryl group of the formula PO3R90 wherein R90 is a hydrogen atom, an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, an aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, an arylalkyl group, including substituted and unsubstituted arylalkyl groups, and wherein hetero atoms either may or may nut be present in the arylalkyl group, an alkylaryl group, including substituted and unsubstituted arylalkyl group, and wherein hetero atoms either may or may not be present in the alkylaryl group, an alkoxy group, including substituted and unsubstituted alkoxy groups, and wherein hetero atoms either may or may not be present in the alkoxy group, an alkoxy group including substituted and unsubstituted aryloxy groups, and wherein hetero atoms either may or may not be present in the aryloxy group, an arylalkyloxy group, including substituted and unsubstituted arylalkyloxy groups, and wherein hetero atoms either may or may not be present in the arylalkyloxy group, an alkylaryloxy group, including substituted and unsubstituted alkylaryloxy groups, and wherein hetero atoms either may or may not be present in the alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, wherein in two or more substituents can be joined together to form a ring, and wherein Z and Z′ can be the same as each other or different from each other;
- and wherein Z and X can be joined together to form a ring and wherein Z′ and X′ can be joined together to form a ring.
7 more elements
A process which comprises (I) incorporating into an ink jet printing apparatus a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula
- comprising a dianthranilate moiety and an acetoacetamido moiety and;
- wherein R is a substituent on the acetoacetamido moiety corresponding to a selected acetoacetamide precursor and wherein R is 2-ethylhexyl, dodecylaniline, Guerbet, or p-hydroxyethylanilino moiety;
- wherein R and R′, if R′ is present, is a substituent on the acetoacetamido moiety corresponding to a selected acetoacetamide precursor on the acetoacetamido moiety and wherein R′, if R′ is present, is 2-ethylhexyl, dodecylaniline, Guerbet, or p-hydroxyethylanilino moiety;
- wherein the number of carbon atoms in R plus R2 is at least about 12;
- wherein R2 is (i) an alkyl group, including substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an alkylene group, including substituted and unsubstituted alkylene groups, and wherein hetero atoms either may or may not be present in the alkylene group, (iii) an arylene group, including substituted and unsubstituted arylene groups, and wherein hetero atoms either may or may not be present in the arylene group (iv) an arylalkylene group, including substituted and unsubstituted arylalkylene groups, and wherein hetero atoms either may or may not be present in the arylalkylene group, (v) an alkylarylene group, including substituted and unsubstituted alkylarylene groups, and wherein hetero atoms either may or may not be present in the alkylarylene group, (vi) an alkyleneoxy group, including substituted and unsubstituted alkyleneoxy groups, and wherein hetero atoms either may or may not be present in the alkyleneoxy group, (vii) an aryleneoxy group, including substituted and unsubstituted aryleneoxy groups, and wherein hetero atoms either may or may not be present in the aryleneoxy group, (viii) an arylalkyleneoxy group, including substituted and unsubstituted arylalkyleneoxy groups, and wherein hetero atoms either may or may not be present in the arylalkyleneoxy group, (ix) an alkylaryleneoxy group, including substituted and unsubstituted alkylaryleneoxy groups, and wherein hetero atoms either may or may not be present in the alkylaryleneoxy group, (x) a polyalkyleneoxy group, (xi) a polyaryleneoxy group, (xii) a polyarylalkyleneoxy group, (xiii) a polyalkylaryleneoxy group, (xiv) a heterocyclic group, (xv) a silylene group, (xvi) a siloxane group, (xvii) a polysilylene group, or (xviii) a polysiloxane group;
- wherein X and X′, if X′ is present, is a (i) direct bond, (ii) an oxygen atom, (iii) a nitrogen atom, (iv) a sulfur atom, (v) a group of the formula —NR40— wherein R40 is a hydrogen atom, an alkyl group, an aryl group, arm arylalkyl group, or an alkylaryl group, (vi) or a group of the formula —CR50R60—;
- wherein R50 and R60 each, independently of the other, is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, wherein two or more substituents can be joined together to form ring, and wherein X and X′ can be the same as each other or different from each other;
- wherein Z and Z′ are each optionally present and if present are each independently selected from a (i) hydrogen atom, (ii) a halogen atom, (iii) a nitro group, (iv) an alkyl group, (v) an aryl group, (vi) an arylalkyl group, (vii) an alkylaryl group, (viii) a group of the formula
- wherein R70 is 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 polyalkyleneoxy group, a polyaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, (ix) a sulfonyl group of the formula —SO2R80 wherein R80 is a hydrogen atom, 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 polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, polysilylene group, or a polysiloxane group, or (x) a phosphoryl group or the formula —PO3R90 wherein R90 is a hydrogen atom, 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 polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, wherein two or more substituents can be joined together to form a ring, and wherein Z and Z′ can be the same as each other or different from each other;
- and
- wherein Z and X can be joined together to form a ring and wherein Z′ and X′ can be joined together to form a ring;
- (2) melting the ink;
- and
- (3) causing droplets of the melted ink to be ejected in an imagewise pattern onto a substrate.
11 more elements
Dependencies are inferred from the claim text.