Process for preparing polymers, polymers, dispersions, inks and uses

• US 9,434,808 B2
• Filed: 07/02/2012
• Issued: 09/06/2016
• Est. Priority Date: 07/07/2011
• Status: Active Grant

• Current Assignee: FUJIFILM Imaging Colorants Limited (Fujifilm Holdings Corporation)
• Original Assignee: FUJIFILM Imaging Colorants Limited (Fujifilm Holdings Corporation)
• Inventors: Wright, Gavin
• Primary Examiner(s): NILAND, PATRICK DENNIS
• Application Number:
  US14/130,948
• Publication Number:
  US 20140309364A1
• Time in Patent Office: 1,527 Days
• US Class Current: 1/1
• CPC Class Codes: C08G 18/0819 containing anionic or anionogenic groups
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/3808 having chlorine atoms
• CPC Class Codes: C08G 18/3851 containing three nitrogen atoms in the ring
• CPC Class Codes: C08G 18/3853 containing cyanurate and/or isocyanurate groups
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C09D 11/102 containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C09D 11/30 Inkjet printing inks
• CPC Class Codes: C09D 11/326 characterised by the pigment dispersant
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

A process for preparing a polymer comprising reacting at least the components i), ii) and optionally iii) to form a pre-polymer: i) a compound of the Formula (1); wherein: T¹ and T² are each independently HO—, HS— or HNR¹—; Q¹ and Q² independently are —NR²—; A¹ and A² independently are an optionally substituted divalent organic linking group; Z is a halogen; R¹ when present is H or an optionally substituted alkyl, aryl or heterocyclyl group; R² is H or an optionally substituted alkyl, aryl or heterocyclyl group; ii) a diisocyanate; iii) optionally an isocyanate reactive compound; and then reacting the pre-polymer with at least component iv): iv) one or more compounds selected from an organic amine, alcohol or thiol provided that at least one of the organic compounds in component iv) has at least one ionic group.

Claims

1. A process for preparing a polymer comprising reacting at least the components i), ii) and optionally iii) to form a pre-polymer:

i) a compound of the Formula (1);

2. The process according to claim 1 wherein at least one of the compounds in component iv) is a compound of the Formula (2) or (3):

L-X 

 

Formula (2)

wherein;

L is H₂N—

, HO—

or HS—

;

X is an optionally substituted organic group having at least one ionic group;

3. The process according to claim 1 wherein T¹ and T² are HO—

and/or A¹ and A² are independently selected from —

(CH₂)_1-20—

groups.

4. The process according to claim 1 resulting in a polymer having a weight averaged molecular weight of from 1,000 to 500,000 as measured by gel permeation chromatography.

5. The process according to claim 1 wherein the resulting polymer has 0.5 to 8 mmoles of ionic groups per g of polymer.

6. The process according to claim 1 wherein the compounds in component iv) are added in a molar amount corresponding to less than 80 mole % relative to the moles of Z groups in the pre-polymer.

7. The process according to claim 1 wherein the remaining un-reacted Z groups are subsequently hydrolysed to OH groups.

8. The process according to claim 1 wherein component iii) is present.

9. The process according to claim 1 wherein the isocyanate reactive compound has only two groups selected from hydroxyl, thiol, amino and hydrazo groups and the isocyanate reactive compound has no ionic groups.

10. The process according to claim 1 wherein at least some of the ionic groups are selected from carboxylic acid, sulfonic acid and phosphorus containing acid groups and at least some of the ionic groups present in the compounds in component iv) are carboxylic acid or phosphorus containing acid groups.

11. The process according to claim 2 wherein T¹ and T² are HO—

, A¹ and A² are independently selected from —

(CH₂)_1-20—

groups, the polymer has a weight averaged molecular weight of from 1,000 to 500,000 as measured by gel permeation chromatography, the polymer has 0.5 to 8 mmoles of ionic groups per g of polymer, the compounds in component iv) are added in a molar amount corresponding to less than 80 mole % relative to the moles of Z groups in the pre-polymer.

12. A polymer obtained by the process according to claim 1.

13. A dispersion comprising a polymer according to claim 12, a particulate solid and a liquid vehicle.

14. A dispersion according to claim 13 wherein the polymer has been cross-linked in the presence of the particulate solid and the liquid vehicle thereby encapsulating the solid particles.

15. An ink comprising a dispersion according to claim 13 wherein the particulate solid is a pigment.

16. The process according to claim 11 wherein the remaining un-reacted Z groups are subsequently hydrolysed to OH groups.

17. The process according to claim 11 wherein component iii) is present.

18. A polymer obtained by the process according to claim 11.

19. A dispersion comprising a polymer according to claim 18, a particulate solid and a liquid vehicle.

20. The dispersion according to claim 19 wherein the polymer has been cross-linked in the presence of the particulate solid and the liquid vehicle thereby encapsulating the solid particles.

21. An ink comprising a dispersion according to 19 wherein the particulate solid is a pigment.