Dye compounds, method of making the compounds and ink composition employing the compounds
View Patent ↗A dye compound of formula 1: where R and R′ are substituents independently selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyl and a solubilizing moiety comprising a substituted or unsubstituted C 10 to C 70 hydrocarbyl group. At least one of R and R′ is not a hydrogen atom or C 1 to C 4 alkyl. R″ and R′″ can be independently selected from the group consisting of a hydrogen atom, C 1 to C 6 alkyl groups or halogens; and X is a squaric acid moiety. A property of the dye compound is that it absorbs radiation having a wavelength in the range of about 700 nm to about 1400 nm.
1. A dye compound of formula 1:
where:
R and R′ are substituents independently selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyl, C 16 to C 70 linear alkyl groups optionally containing one or more heteroatoms; a carbamate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amide having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amine having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; a carboxylate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; and polymers that include a C 10 to C 70 long chain hydrocarbon backbone, wherein at least one of R and R′ is not a hydrogen atom or C 1 to C 4 alkyl;
R″ and R′″ can be independently selected from the group consisting of a hydrogen atom, C 1 to C 6 alkyl groups or halogens; and
X is a squaric acid moiety,
wherein a property of the dye compound is that it absorbs radiation having a wavelength in the range of about 700 nm to about 1400 nm.
2. The compound of claim 1 , wherein at least one of R and R′ are selected from the group consisting of a carbamate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amide having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amine having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; a carboxylate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; and polymers that include a C 10 to C 70 long chain hydrocarbon backbone.
3. The compound of claim 2 , wherein at least one of R and R′ is a substituent of formula 2:
where R 2 is a C 1 to C 4 alkyl bridge and R 4 is a C 15 to C 22 alkyl.
4. The compound of claim 2 , wherein at least one of R and R′ is a substituent of formula 3:
where R 2 is a C 1 to C 4 alkyl bridge and R 5 is a C 15 to C 22 alkyl.
5. The compound of claim 1 , wherein at least one of R and R′ is a C 16 to C 20 alkyl.
6. The compound of claim 1 , wherein R and R′ are selected from the group consisting of n-heptadecyl and n-octadecyl.
7. A phase change ink composition, comprising:
a wax;
a resin; and
a dye compound of formula 1:
where:
R and R′ are substituents independently selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyl, C 10 to C 70 linear, branched or cyclic alkyl groups optionally containing one or more heteroatoms; a carbamate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amide having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amine having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; a carboxylate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; and polymers that include a C 10 to C 70 long chain hydrocarbon backbone, wherein at least one of R and R′ is not a hydrogen atom or C 1 to C 4 alkyl;
R″ and R′″ can be independently selected from the group consisting of a hydrogen atom, C 1 to C 6 alkyl groups or halogens, and
X is a squaric acid moiety,
wherein a property of the dye compound is that it absorbs radiation having a wavelength in the range of about 700 nm to about 1400 nm, and further wherein the dye compound is soluble in the wax.
8. The composition of claim 7 , wherein at least one of R and R′ are selected from the group consisting of C 16 to C 70 linear alkyl groups containing one or more heteroatoms; a carbamate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amide having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amine having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; a carboxylate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; and polymers that include a C 10 to C 70 long chain hydrocarbon backbone.
9. The composition of claim 7 , wherein at least one of R and R′ is a substituent of formula 2:
where R 2 is selected from the group consisting of a C 1 to C 4 alkyl bridge and R 4 is a C 15 to C 22 alkyl.
10. The composition of claim 7 , wherein at least one of R and R′ is a substituent of formula 3:
where R 2 is a C 1 to C 4 alkyl bridge and R 5 is a C 15 to C 22 alkyl.
11. The composition of claim 7 , wherein at least one of R and R′ is a C 15 to C 22 alkyl.
12. A method of making a phase change ink compound, the method comprising:
reacting squaric acid and a second compound of formula 4:
where R and R′ are substituents independently selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyl, C 16 to C 70 linear alkyl groups optionally containing one or more heteroatoms; a carbamate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amide having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amine having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; a carboxylate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; and polymers that include a C 10 to C 70 long chain hydrocarbon backbone, wherein at least one of R and R′ is not a hydrogen atom or C 1 to C 4 alkyl; and
R″ and R′″ are independently selected from the group consisting of a hydrogen atom, C 1 to C 6 alkyl groups and halogens.
13. The method of claim 12 , wherein at least one of R and R′ is a C 16 to C 20 alkyl.
14. The method of claim 12 , wherein the compound of formula 4 is formed by reacting 1,8-diaminonaphthalene and stearone.
15. The method of claim 12 , wherein the compound of formula 4 is formed by reacting an isocyanate with a compound of formula 5:
where R 3 is selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyls and a hydroxyl group; R 2 is chosen from a C 1 to C 4 alkyl bridge; and R″ and R′″ are as defined in claim 12 .
16. The method of claim 15 , wherein the isocyanate is OCNR 8 , where R 8 is a linear C 16 to C 19 alkyl.
17. The method of claim 12 , wherein the compound of formula 4 is formed by reacting a carboxylic acid with a compound of formula 5:
where R 3 is selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyls and a hydroxyl group; R 2 is chosen from a C 1 to C 4 alkyl bridge; and R″ and R′″ are as defined in claim 12 .
18. The method of claim 17 , wherein the carboxylic acid is R 10 COOH, where R 10 is a linear C 15 to C 17 alkyl.
19. The method of claim 12 , wherein at least one of R and R′ are selected from the group consisting of a carbamate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amide having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amine having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; a carboxylate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; and polymers that include a C 10 to C 70 long chain hydrocarbon backbone.
20. The composition of claim 7 , wherein at least one of R and R′ are selected from the group consisting of a carbamate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amide having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an amine having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; a carboxylate having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; and polymers that include a C 10 to C 70 long chain hydrocarbon backbone.