Ink compositions
Polyurethanes containing at least one bisphosphonate group, as well as related compositions, articles, and methods, are disclosed.
1. An inkjet ink composition, comprising:
a polyurethane comprising a first comonomer repeat unit that comprises a hydrophilic group, the polyurethane further comprising a functional group different from the hydrophilic group, wherein the functional group comprises (CH 2 ) n ,C(R)(PO 3 H 2 ) 2 or an ester or salt thereof, in which n is 0-9 and R is H, R a , OR a , SR a , or NR a R b , each of R a and R b , independently, being H, C 1 -C 10 alkyl, or aryl;
a liquid vehicle; and
a pigment.
2. The composition of claim 1 , wherein the functional group comprises a partial salt of (CH 2 ) n ,C(R)(PO 3 H 2 ) 2 , and the partial salt comprises an anion formed from (CH 2 ) n , C(R)(PO 3 H 2 ) 2 and a cation selected from the group consisting of Li + , Na + , K + , Cs + , or N(R c ) 4 + , in which R c is H, C 1 -C 10 alkyl, or aryl.
3. The composition of claim 1 , wherein the functional group comprises a partial salt containing K + and an anion formed from (CH 2 ) n C(R)(PO 3 H 2 ) 2 .
4. The composition of claim 1 , wherein n is 1-3 and R is OR a .
5. The composition of claim 1 , wherein n is 3 and R is OH.
6. The composition of claim 1 , wherein the polyurethane comprises at least about 0.1 wt % phosphorus.
7. The composition of claim 1 , wherein the hydrophilic group comprises a carboxylic acid group, a sulfonic acid group, a phosphonic acid group, a hydroxyl group, a polyether group, or a salt thereof.
8. The composition of claim 1 , wherein the first comonomer repeat unit is of formula (I):
—O—R 1 —O— (I),
in which R 1 is C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 heterocycloalkylene, arylene, heteroarylene, or C 1 -C 20 alkylarylene, each of which is substituted with the hydrophilic group and optionally further substituted with C 1 -C 10 alkyl or aryl.
9. The composition of claim 8 , wherein R 1 is C 1 -C 10 alkylene substituted with a carboxylic acid or a salt thereof.
10. The composition of claim 8 , wherein R 1 is CH 2 C(CH 3 )(COOH)CH 2 or a salt thereof.
11. The composition of claim 1 , wherein the first comonomer repeat unit is at least about 1% of the total weight of the polyurethane.
12. The composition of claim 1 , wherein the polyurethane further comprises a second comonomer repeat unit of formula (II):
—C(O)—NH—R 2 —NH—C(O)— (II),
in which R 2 is C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 heterocycloalkylene, arylene, heteroarylene, or a combination thereof, each of which is optionally substituted with C 1 -C 10 alkyl or aryl.
13. The composition of claim 12 , wherein R 2 is C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, arylene, or a combination thereof.
14. The composition of claim 12 , wherein R 2 is hexamethylene, phenylene optionally substituted with methyl, cyclohexylene optionally substituted with methyl,
15. The composition of claim 1 , wherein the polyurethane further comprises a third comonomer repeat unit of formula (III):
—O——R 3 —O— (III),
wherein R 3 comprises C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 heterocycloalkylene, arylene, heteroarylene, a polyether moiety, a polyester moiety, a polycarbonate moiety, a polyacetal moiety, a polythioether moiety, a polyester amide moiety, a polyacrylate moiety, a polyolefin moiety, a polyalkylsiloxane moiety, or a mixture thereof.
16. The composition of claim 15 , wherein R 3 comprises a polypropylene glycol moiety, a polytetramethyleneoxide moiety, a poly(butylene adipate) moiety, a poly(hexamethylene adipate) moiety, a polycarbonate moiety prepared from 2-butyl-2-ethylpropyl diol, a polycarbonate moiety prepared from a mixture of 1,5-pentanediol and 1,6-hexanediol.
17. The composition of claim 1 , wherein the polyurethane has an acid number of at least about 25.
18. The composition of claim 1 , wherein the polyurethane has a weight average molecule weight of at least about 10,000 g/mol.
19. The composition of claim 1 , wherein the polyurethane is from about 0.1% to about 15% of the total weight of the composition.
20. The composition of claim 1 , wherein the liquid vehicle comprises an aqueous solution.
21. The composition of claim 1 , further comprising at least one additive selected from the group consisting of surfactants, biocides, and humectants.