Ink compositions
Polyurethanes containing at least one bisphosphonate group, as well as related compositions, articles, and methods, are disclosed.
1. A composition, comprising:
a polyurethane;
a pigment; and
a liquid vehicle,
wherein the polyurethane comprises:
a first comonomer repeat unit that comprises a hydrophilic group, and
a functional group different from the hydrophilic group, the functional group comprising (CH 2 ) n C(R)(PO 3 H 2 ) 2 or an ester or salt thereof wherein the functional group is an end group of the polyurethane, and
wherein n is 0-9 and R is H, R a , OR a , SR a , or NR a R b , in which each of R a and R b , independently, being H, C 1 -C 10 alkyl, or aryl.
2. The composition of claim 1 , wherein the pigment comprises carbon black.
3. The composition of claim 1 , wherein the liquid vehicle comprises an aqueous solution.
4. A polyurethane, comprising:
a comonomer repeat unit of formula (IV) or (V):
—N(R 9 )—R 4 —N(R 6 )—R 5 —N(R 10 )— (IV)
or
—N(R 9 )—R 4 —C(R 7 R 8 )—R 5 —N(R 10 )— (V)
wherein
each of R 4 and R 5 , independently, is a bond, C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 heterocycloalkylene, arylene, or heteroarylene, each of which being optionally substituted with C 1 -C 10 alkyl or aryl, provided that at least one of R 4 and R 5 is not a bond;
R 6 is (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;
each of R 7 and R 8 , independently, is H, R c , OR c , SR c , NR c R d , PO 3 H 2 or an ester or salt thereof, or (CH 2 ) m C(R′)(PO 3 H 2 ) 2 or an ester or salt thereof, in which m is 0-9 and R′ is H, R c , OR c , SR c , or NR c R d , each of R c and R d , independently, being H, C 1 -C 10 alkyl, or aryl, provided that, if neither of R 7 and R 8 is (CH 2 ) m C(R′)(PO 3 H 2 ) 2 or an ester or salt thereof, both of R 7 and R 8 are PO 3 H 2 or an ester or salt thereof; and
each of R 9 and R 10 , independently, is H, C 1 -C 10 alkyl, or aryl.
5. A composition, comprising:
the polyurethane of claim 4 ; and
a liquid vehicle.
6. 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.
7. 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 .
8. The composition of claim 1 , wherein n is 1-3 and R is OR a .
9. The composition of claim 1 , wherein n is 3 and R is OH.
10. The composition of claim 1 , wherein the polyurethane comprises two functional groups that comprise (CH 2 ) n C(R)(PO 3 H 2 ) 2 or an ester or salt thereof, each of which is an end group of the polyurethane.
11. The composition of claim 1 , wherein the polyurethane comprises at least about 0.1 wt % phosphorus.
12. 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.
13. 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.
14. The composition of claim 13 , wherein R 1 is C 1 -C 10 alkylene substituted with a carboxylic acid or a salt thereof.
15. The composition of claim 13 , wherein R 1 is CH 2 C(CH 3 )(COOH)CH 2 or a salt thereof.
16. The composition of claim 1 , wherein the first comonomer repeat unit is at least about 1% of the total weight of the polyurethane.
17. 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.
18. The composition of claim 17 , wherein R 2 is C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, arylene, or a combination thereof.
19. The composition of claim 17 , wherein R 2 is hexamethylene, phenylene optionally substituted with methyl, cyclohexylene optionally substituted with methyl,
20. 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.
21. The composition of claim 20 , 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.
22. The composition of claim 1 , wherein the polyurethane has an acid number of at least about 25.
23. The composition of claim 1 , wherein the polyurethane has a weight average molecule weight of at least about 10,000 g/mol.
24. The composition of claim 1 , wherein the polyurethane is from about 0.1% to about 15% of the total weight of the composition.