Dye compound and method of making the compound
A perimidine coupler 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 or 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 and halogens.
1. A perimidine coupler 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 or a solubilizing moiety comprising a substituted or unsubstituted hydrocarbyl group; wherein at least one of R and R′ is not a hydrogen atom or C 1 to C 4 alkyl; and wherein R″ and R′″ can be independently selected from the group consisting of a hydrogen atom, C 1 to C 6 alkyl groups and halogens, and wherein the R and R′ solubilizing moieties comprising the substituted or unsubstituted hydrocarbyl group are selected from the group consisting of C 16 to C 70 linear, branched or cyclic alkyl groups, optionally, containing one or more heteroatoms; an oxyalkyl having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; an ether having a substituted or unsubstituted C 10 to C 70 hydrocarbyl tail; 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 hydrocarbon backbone.
2. The compound of claim 1 , wherein at east one of R and R′ is a substituent of formula 2:
where R 2 is selected from the group consisting of a methylene and an ethyl bridge and R 4 is a C 12 to C 50 alkyl.
3. The compound of claim 2 , wherein R 2 is methylene and R 4 is selected from the group consisting of n-hexadecyl, n-heptadecyl and n-octadecyl.
4. The compound of claim 1 , wherein at least one of R and R′ is a substituent of formula 3:
where R 2 is selected from the group consisting of a methylene and an ethyl bridge and R 5 is a C 12 to C 50 alkyl.
5. The compound of claim 4 , wherein R 2 is methylene and R 5 is selected from the group consisting of n-hexadecyl, n-heptadecyl and n-octadecyl.
6. The compound of claim 1 , wherein both of R and R′ are C 12 to C 50 alkyls.
7. The compound of claim 1 , wherein R and R′ are selected from the group consisting of n-hexadecyl, n-heptadecyl and n-octadecyl.
8. A method of making the perimidine coupler of claim 1 , the method comprising reacting 1,8-diaminonaphthalene and at least one carbonyl functionalized compound comprising a substituted or unsubstituted C 10 to C 70 hydrocarbyl group.
9. The method of claim 8 , wherein the carbonyl functionalized compound is a compound of formula 4:
where R and R′ are independently selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyls or C 10 to C 70 alkyls, wherein at least one of R and R′ is not a hydrogen atom or C 1 to C 4 alkyl.
10. The method of claim 8 , wherein the carbonyl functionalized compound is stearone.
11. A perimidine coupler made by the method of claim 8 , the perimidine coupler comprising at least one substituent selected from the group consisting of linear, branched or cyclic C 10 to C 70 alkyl groups optionally containing one or more heteroatoms.
12. A method of making the perimidine coupler of claim 1 , the method comprising:
reacting 1,8-diaminonaphthalene and a carbonyl functionalized compound to form a substituted intermediate perimidine structure; and
reacting the substituted intermediate perimidine structure with a second compound to form a C 10 to C 70 hydrocarbyl substituted perimidine coupler, the second compound being selected from the group consisting of a C 10 to C 70 hydrocarbyl substituted acid, a C 10 to C 70 hydrocarbyl substituted isocyanate, a C 10 to C 70 hydrocarbyl substituted amine and a C 10 to C 70 hydrocarbyl substituted alcohol.
13. The method of 12 , wherein the carbonyl functionalized compound is a hydroxyalkyl substituted carbonyl compound and the substituted intermediate perimidine structure is a hydroxyalkyl substituted perimidine; and
the second compound is selected from the group consisting of a C 10 to C 70 hydrocarbyl substituted acid and a C 10 to C 70 hydrocarbyl substituted isocyanate.
14. The method of claim 13 , wherein the hydroxyalkyl substituted carbonyl compound is a compound of formula 6:
where R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, C 1 to C 4 alkyl, hydroxymethyl and hydroxyethyl, wherein at least one of R 1 and R 2 is not a hydrogen atom or C 1 to C 4 alkyl.
15. The method of claim 14 , wherein the hydroxyalkyl substituted perimidine is reacted with the hydrocarbyl substituted acid, the acid being a compound of formula 7:
CH 3 (CH 2 ) n —CO 2 H (7)
where n is an integer ranging from 12 to 50.
16. The method of claim 15 , wherein n is in integer ranging from 15 to 25.
17. The method of claim 14 , wherein the hydroxyalkyl substituted perimidine is reacted with the hydrocarbyl substituted isocyanate, the isocyanate being a compound of formula (8):
CH 3 (CH 2 ) n —NCO (8)
where n is an integer ranging from 10 to 50.
18. The method of claim 17 , wherein n is in integer ranging from 12 to 20.
19. A wax soluble perimidine coupler made by the method of claim 12 , the perimidine coupler comprising at least one substituent selected from the group consisting of C 10 to C 70 carbamate esters, C 10 to C 70 carboxylate esters and C 10 to C 70 amides.