Amphoteric polymers and use in inkjet ink compositions

Patent metadata

Field	Value
Publication number	US-10414865-B2
Application number	US-201615573309-A
Country	US
Kind code	B2
Filing date	May 13, 2016
Priority date	May 15, 2015
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

Disclosed herein are inkjet ink compositions comprising a polymer comprising the repeat units (A), (B), and (C), wherein: (A) is selected from —N + (R 1 )(R 2 )— and —N(R 1 )—; (B) is selected from C 1 -C 10 alkylene; C 3 -C 20 cycloalkylene; C 3 -C 20 heterocycloalkylene; arylene; heteroarylene; C 2 -C 20 ether; C 2 -C 20 thioether; C 2 -C 20 ester; C 2 -C 20 acetal; C 2 -C 20 amide; bisphenols; and oligomer and polymer moieties selected from polyether, polyester, polyamines, polycarbonate, polyacetal, polythioether, polyester amide, polyurethane, polyacrylate, polyolefin, and polyalkylsiloxane, and (C) comprises at least one group selected from: (i) —C(R 3 ) (R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 ))m-, (ii) —C(R 3 )(R 4 )—C(R 5 )(H)—C(O)—, and (iii) —C(R 3 )(R 4 )—C(R 5 )(H)—S(O)(O); and (A) is bonded to the —C(R 3 )(R 4 )— group of (C), and (B) is bonded to (C).

First claim

The invention claimed is:

1. A polymer comprising the repeat units (A), (B), and (C), wherein:
(A) is selected from N(R 1 ) and —N + (R 1 )(R 2 )—;
(B) is selected from C 1 -C 10 alkylene; C 3 -C 20 cycloalkylene; C 3 -C 20 heterocycloalkylene; arylene; heteroarylene; C 2 -C 20 ether; C 2 -C 20 thioether; C 2 -C 20 ester; C 2 -C 20 acetal; C 2 -C 20 amide; bisphenols; and oligomer and polymer moieties selected from polyether, polyester, polyamines, polycarbonate, polyacetal, polythioether, polyester amide, polyurethane, polyacrylate, polyolefin, and polyalkylsiloxane,
(C) comprises at least one group selected from:
(i) —C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m —,
(ii) —C(R 3 )(R 4 )—C(R 5 )(H)—C(O)—, and
(iii) —C(R 3 )(R 4 )—C(R 5 )(H)—S(O)(O)—; and

(A) is bonded to the —C(R 3 )(R 4 )— group of (C),
(B) is bonded to (C),
R 1 is selected from C 1 -C 10 alkyl, C 4 -C 18 aryl, C 4 -C 18 heteroaryl, and C 3 -C 20 heterocycloalkyl, each being substituted with at least one functional group; R 2 is selected from H, C 1 -C 10 alkyl, C 4 -C 18 aryl, C 1 -C 10 alkyl substituted with at least one functional group, and C 4 -C 18 aryl substituted with at least one functional group, wherein R 1 , or R 1 and R 2 together, has a calcium index value greater than or equal to a calcium index value of phenylphosphonic acid,
m is an integer ranging from 0-10, and
R 3 -R 7 are each independently selected from H; C 1 -C 10 alkyl; and C 4 -C 18 aryl.

2. The polymer of claim 1 , wherein (B) is bonded to (C) via linker group X, wherein X is selected from O, N(R 8 ), C(R 9 )(R 10 ), and O—C(R 9 )(R 10 ), and R 8 -R 10 are each independently selected from H; C 1 -C 10 alkyl; and C 4 -C 18 aryl.

3. The polymer of claim 2 , wherein (B) is bonded to two (C) repeat units via respective X groups, X 1 and X 2 , such that the polymer comprises the repeat unit:
C-X 1 -B-X 2 -C
wherein X 1 and X 2 are independently selected from O, N(R 8 ), C(R 9 )(R 10 ), and O—C(R 9 )(R 10 ).

4. The polymer of claim 1 , wherein (B) is bonded to two different (C) repeat units, such that the polymer comprises the repeat unit C 1 -B-C 2 .

5. The polymer of claim 2 , wherein the polymer comprises at least one repeat unit selected from:
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -B-X-(C(R 11 )(R 12 )) m —C(R 13 )(OH)—C(R 14 )(R 15 )—,
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -X-B-(C(R 11 )(R 12 )) m —C(R 13 )(OH)—C(R 14 )(R 15 )—,
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -X 1 -B-X 2 -(C(R 11 )(R 12 )) m —C(R 13 )(OH)—C(R 14 )(R 15 )—,
—C(R 3 )(R 4 )—C(R 5 )(H)—C(O)-B-X-C(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )—(H)—C(O)-X-B-C(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(H)—C(O)-X 1 -B-X 2 -C(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(H)—S(O)(O)-B-X-S(O)(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(H)—S(O)(O)-X-B-S(O)(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(H)—S(O)(O)-X 1 -B-X 2 -S(O)(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -B-X-C(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -X-B-C(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -X 1 -B-X 2 -C(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -B-X-S(O)(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -X-B-S(O)(O)—C(R 11 )(H)—C(R 12 )(R 13 )—, and
—C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m -X 1 -B-X 2 -S(O)(O)—C(R 11 )(H)—C(R 12 )(R 13 )—,
wherein R 11 -R 15 are each independently selected from H; C 1 -C 10 alkyl; and C 4 -C 18 aryl; wherein X 1 and X 2 are independently selected from O, N(R 8 ), C(R 9 )(R 10 ), and O—C(R 9 )(R 10 ).

6. The polymer of claim 1 , wherein the polymer comprises both —N(R 1 )— and —N + (R 1 )(R 2 )— as repeat unit (A).

7. The polymer of claim 1 , wherein (C) is derived from: diglycidyl ethers of repeat unit (B), from α,β-unsaturated carbonyl derivatives of repeat unit (B), or α,β-unsaturated sulfonyl derivatives of repeat unit (B).

8. The polymer of claim 1 , wherein the at least one functional group comprises at least one ionic group, at least one ionizable group, or mixtures thereof.

9. The polymer of claim 1 , wherein the at least one functional group is selected from at least one phosphonic acid group, partial esters thereof, and salts thereof.

10. The polymer of claim 1 , wherein the at least one functional group is selected from at least two phosphonic acid groups, partial esters thereof, and salts thereof.

11. The polymer of claim 1 , wherein the at least one functional group is selected from at one geminal bisphosphonic acid group, partial esters thereof, and salts thereof.

12. The polymer of claim 1 , wherein the at least one functional group is selected from —C(OH)(PO 3 H 2 ) 2 , —CH 2 C(OH)(PO 3 H 2 ) 2 , —CH 2 CH 2 C(OH)(PO 3 H 2 ) 2 , —CH 2 CH 2 CH 2 C(OH)(PO 3 H 2 ) 2 , —CH(PO 3 H 2 ) 2 , —CH 2 CH(PO 3 H 2 ) 2 , partial esters thereof, and salts thereof.

13. The polymer of claim 1 , wherein the at least one functional group comprises an acid.

14. The polymer of claim 13 , wherein the acid comprises at least one group selected from —COOH, SO 3 H, —OSO 3 H, —HPO 3 H, —OPO 3 H, and —PO 3 H.

15. The polymer of claim 1 , wherein the polymer has an acid number of at least 30, wherein acid number is defined as:
AN=(moles of acid-containing monomer)×56.1 mg KOH/mol× n ×1000/(the total mass (g) of polymer sample), where n =number of moles of ionizable protons per moles of acid-containing monomer.

16. The polymer of claim 15 , wherein the number of (A) repeat units in the polymer is indicated by an amine number defined as:
AmineNum=moles of amino-containing monomer×56.1 mg KOH/mol× n ×1000/(the total mass (g) of polymer sample), where n =number of moles of basic nitrogens per moles of monomer,

and wherein the amine number is at least 25.

17. The polymer of claim 16 , wherein acid number is greater than amine number.

18. The polymer of claim 1 , wherein the polymer further comprises a repeat unit having the formula:
D-C-B-C
wherein repeat unit (D) is bonded to the —C(R 3 )(R 4 )— group of (C), and wherein (D) is selected from amines, polyamines, thioethers, and polythioethers.

19. The polymer of of claim 18 , wherein repeat unit (D) does not contain a functional group having a calcium index value greater than or equal to a calcium index value of phenylphosphonic acid.

20. The polymer of claim 1 , wherein the polymer is crosslinked.

21. A dispersion comprising the polymer of claim 1 , wherein the dispersion further comprises a pigment and a liquid vehicle.

22. An inkjet ink composition comprising:
a pigment;
a liquid vehicle; and
polymer comprising the repeat units (A), (B), and (C), wherein:
(A) is selected from —N(R 1 )— and —N + (R 1 )(R 2 )—;
(B) is selected from C 1 -C 10 alkylene; C 3 -C 20 cycloalkylene; C 3 -C 20 heterocycloalkylene; arylene; heteroarylene; C 2 -C 20 ether; C 2 -C 20 thioether; C 2 -C 20 ester; C 2 -C 20 acetal; C 2 -C 20 amide; bisphenols; and oligomer and polymer moieties selected from polyether, polyester, polyamines, polycarbonate, polyacetal, polythioether, polyester amide, polyurethane, polyacrylate, polyolefin, and polyalkylsiloxane,
(C) comprises at least one group selected from:
(i) —C(R 3 )(R 4 )—C(R 5 )(OH)—(C(R 6 )(R 7 )) m —,
(ii) —C(R 3 )(R 4 )—C(R 5 )(H)—C(O)—, and

Assignees

• Cabot Corp

Inventors

• Palumbo Paul S
• Xu Jinqi

Classifications

• C09B67/00

  Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents {grinding or grinding assistants, coating of pigments or dyes}; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films · CPC title

• C08G73/0633

  with only two nitrogen atoms in the ring · CPC title

• C09D11/326

  characterised by the pigment dispersant · CPC title

• C09D11/10

  based on artificial resins · CPC title

• C08G73/0253

  Polyamines containing sulfur in the main chain · CPC title