IP Library Granted Patent US 10,513,622
Granted Patent B2
US 10,513,622 · App. 15/729,736 · Granted Dec 24, 2019

Aqueous inkjet ink compositions and ink sets

Inventors: Catherine A. Falkner (Rochester, NY); John Leonard Muehlbauer (Stafford, NY); Peter John Ghyzel (Rochester, NY); Valerie Lynn Kuykendall (Penfield, NY); Thomas B. Brust (Webster, NY)
C09D11/30C09D11/40
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,513,622
App. No.
15/729,736
Granted
Dec 24, 2019
Kind
B2
Abstract

Individual aqueous inks or inks in ink sets haves a non-crosslinked, crosslinkable polyurethane having an acid number of 20-40 and is derived from an aromatic diisocyanate; and a diol mixture of D 1 and D 2 diols, and optionally including D 3 diol, D 4 diol, or both D 3 and D 4 diols. D 1 has a C 3 to C 7 aliphatic group and a pendant carboxy group or neutralized carboxy group. D 2 has a chain of repeating C 2 to C 6 alkylene oxide groups. D 3 is an alkoxylated bisphenol A or an aliphatic cyclic diol, present at least 5 mol %. D 4 is a hydroxy-terminated polybutadiene having a molecular weight of at least 1000 and is present in an amount of 0.1-5 mol %. The ink also contains a dispersed pigment colorant; a humectant or organic co-solvent, and optionally, a crosslinking agent.

Claims (46)

1. An aqueous inkjet ink composition having a viscosity of at least 1 centipoise and up to and including 100 centipoise at 25° C., and comprising:

(a) an aqueous solvent medium,

(b) a non-crosslinked, crosslinkable polyurethane having an acid number of at least 20 and up to and including 40, and a glass transition temperature (T g ) of up to and including 40° C.,

the non-crosslinked, crosslinkable polyurethane derived from:

1) an aromatic diisocyanate; and

2) a diol mixture of D 1 , D 2 , and D 3 diols, and optionally including a D 4 diol,

wherein:

the D 1 diol comprises a C 3 to C 7 aliphatic group between two hydroxy groups, and at least one pendant carboxy group or pendant neutralized carboxy group,

the D 2 diol comprises a chain of one or more repeating C 2 to C 6 alkylene oxide groups and has a weight average molecular weight of at least 250 and up to and including 3,000,

the D 3 diol is an alkoxylated bisphenol A or an aliphatic cyclic diol that is present in an amount of at least 5 mol %, based on the total molar amount of the D 1 through D 4 diols in the diol mixture, and

the D 4 diol is a hydroxy-terminated polybutadiene having a weight average molecular weight of at least 1000, and when present, is present in an amount of at least 0.1 mol % and up to and including 5 mol %, based on the total molar amount of the D 1 through D 4 diols in the diol mixture;

(c) a dispersed pigment colorant;

(d) a humectant or organic co-solvent; and

(e) optionally, a crosslinking agent.

2. The aqueous inkjet ink composition of claim 1 , wherein the dispersed pigment colorant is dispersed using an anionic surfactant having a molecular weight of less than 500.

3. The aqueous inkjet ink composition of claim 1 , further comprising the crosslinking agent that is a melamine formaldehyde resin, carbodiimide, glyoxal, urea resin, or phenolic resin.

4. The aqueous inkjet ink composition of claim 1 , wherein the non-crosslinked, crosslinkable polyurethane is present in an amount of at least 2 weight % and up to and including 15 weight %, based on the total wet weight of the inkjet ink composition.

5. The aqueous inkjet ink composition of claim 1 , wherein the humectant or organic co-solvent is present in an amount of at least 0.5 weight % and up to and including 35 weight %, based on the total weight of the aqueous inkjet ink composition.

6. The aqueous inkjet ink composition of claim 1 , having a viscosity of at least 1 and up to and including 30 centipoise, at 25° C.

7. The aqueous inkjet ink composition of claim 1 , wherein the diol mixture further comprises the D 4 diol.

8. The aqueous inkjet ink composition of claim 1 , wherein the non-crosslinked, crosslinkable polyurethane has an acid number of at least 20 and up to and including 35.

9. The aqueous inkjet ink composition of claim 1 , wherein the non-crosslinked, crosslinkable polyurethane has a weight average molecular weight (M w ) of at least 20,000 and up to and including 150,000.

10. The aqueous inkjet ink composition of claim 1 , wherein the D 1 dial comprises a C 3 to C 5 aliphatic group between the two hydroxy groups.

11. The aqueous inkjet ink composition of claim 1 , wherein the D 2 diol comprises a chain of repeating C 3 or C 4 alkylene oxide groups and has a weight average molecular weight of at least 250 and up to and including 1,000.

12. The aqueous inkjet ink composition of claim 1 , wherein the D 3 diol is an alkoxylated bisphenol A.

13. The aqueous inkjet ink composition of claim 1 , wherein the D 3 diol is present in an amount of at least 5 mol % and up to and including 30 mol %, based on the total molar amount of the D 1 through D 4 diols in the diol mixture.

14. The aqueous inkjet ink composition of claim 1 , wherein the D 3 diol is present in an amount of at least 8 mol % and up to and including 25 mol %, based on the total molar amount of the D 1 through D 4 diols in the diol mixture.

15. The aqueous inkjet ink composition of claim 7 , wherein the D 4 diol has a weight average molecular weight of at least 1,000 and up to and including 7,000.

16. The aqueous inkjet ink composition of claim 7 , wherein the D 4 diol is present in the diol mixture in an amount of at least 0.1 mol % and up to and including 5 mol %, based on the total molar amount of the D 1 through D 4 diols in the diol mixture.

17. An inkjet ink set, comprising:

two or more aqueous color inkjet ink compositions, at least one of which is an aqueous inkjet ink composition having a viscosity of at least 1 centipoise and up to and including 100 centipoise at 25° C., and comprising:

(a) an aqueous solvent medium,

(b) a non-crosslinked, crosslinkable polyurethane having an acid number of at least 20 and up to and including 40, and a glass transition temperature (Tg) of up to and including 40° C.,

the non-crosslinked, crosslinkable polyurethane derived from:

1) an aromatic diisocyanate; and

2) a diol mixture of D 1 , D 2 , and D 3 diols, and optionally including a D 4 diol,

wherein:

the D 1 diol comprises a C 3 to C 7 aliphatic group between two hydroxy groups, and at least one pendant carboxy group or pendant neutralized carboxy group,

the D 2 diol comprises a chain of one or more repeating C 2 to C 6 alkylene oxide groups and has a weight average molecular weight of at least 250 and up to and including 3,000,

the D 3 diol is an alkoxylated bisphenol A or an aliphatic cyclic diol that is present in an amount of at least 5 mol %, based on the total molar amount of the D 1 through D 4 diols in the diol mixture, and

the D 4 diol is a hydroxy-terminated polybutadiene having a weight average molecular weight of at least 1000, and when present, is present in an amount of at least 0.1 mol % and up to and including 5 mol %, based on the total molar amount of the D 1 through D 4 diols in the diol mixture;

(c) a dispersed pigment colorant that is stabilized with an anionic surfactant having a molecular weight of less than 500;

(d) a humectant or organic co-solvent; and

(e) optionally, a crosslinking agent.

18. The inkjet ink set of claim 17 , comprising at least one each of an aqueous cyan inkjet ink composition, an aqueous magenta inkjet ink composition, and a yellow inkjet ink composition, and optionally, an aqueous black inkjet ink composition.

19. The inkjet ink composition of claim 18 , wherein the non-crosslinked, crosslinkable polyurethane is present in at least one of the aqueous cyan inkjet ink composition, the aqueous magenta inkjet ink composition, and the yellow inkjet ink composition, and the optional aqueous black inkjet ink composition.

Assignments (9)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
NOTICE OF SECURITY INTERESTS Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 056984/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0233 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 30, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; PFC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 049901/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 22, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
SECURITY INTEREST Recorded Nov 13, 2017
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BANK OF AMERICA N.A.
Reel/Frame 044100/0585 →
SECURITY INTEREST Recorded Nov 13, 2017
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: JP MORGAN CHASE BANK, N.A.
Reel/Frame 044099/0729 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2017
From: FALKNER, CATHERINE A.; MUEHLBAUER, JOHN LEONARD; GHYZEL, PETER JOHN; KUYKENDALL, VALERIE LYNN; BRUST, THOMAS B.
To: EASTMAN KODAK COMPANY
Reel/Frame 043834/0090 →
Continuity (1)
Related Publication 20190106586A1 · Apr 11, 2019
Cited By (2)
US 12,617,956 US 12,617,958