Hot melt ink composition comprising a copolyester and process for preparing a copolyester

Patent metadata

Field	Value
Publication number	US-9340691-B2
Application number	US-201314142550-A
Country	US
Kind code	B2
Filing date	Dec 27, 2013
Priority date	Jun 30, 2011
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

A hot melt ink composition includes a copolyester, the copolyester consisting essentially of a condensation product of a first type of monomer, a second type of monomer and a third type of monomer, wherein the first type of monomer comprises at least one monomer A selected from the group of polyhydroxyl alcohols comprising X hydroxyl functional groups, wherein X≧3, wherein the second type of monomer comprises at least one monomer B selected from the group of monomers being able to form an ester linkage with an alcohol and wherein the third type of monomer comprises at least one monomer C selected from the group of aromatic monocarboxylic acids. A method for preparing such copolyesters and a hot melt ink composition includes a mixture of such copolyesters.

First claim

What is claimed is:

1. A hot melt ink composition comprising:
a copolyester, the copolyester consisting essentially of a condensation product of a first type of monomer, a second type of monomer, and a third type of monomer,
wherein the first type of monomer comprises at least one monomer A, said monomer A being a polyhydroxyl alcohol comprising X hydroxyl functional groups, wherein X≧3,
wherein the second type of monomer comprises at least one monomer B, said monomer B being a monomer able to form an ester linkage with an alcohol, and
wherein the third type of monomer comprises at least one monomer C, said monomer C being an aromatic monocarboxylic acid.

2. The hot melt ink composition according to claim 1 , wherein the viscosity η of the copolyester at a temperature of 150° C. is less than 400 mPa·s.

3. The hot melt ink composition according to claim 1 , wherein the weight averaged molecular weight M w of the copolyester is 4000 gram/mole or less.

4. The hot melt ink composition according to claim 1 , wherein the at least one monomer A is selected from at least one of the group consisting of glycerol, pentaerythritol, 2-(hydroxymethyl)-2-methylpropane-1,3-diol, 2-ethyl-2-(hydroxymethyl)propane-1,3-diol, dipentaerythritol, trimethylolethane, trimethylolpropane, trimethylolbutane and trimethylolpentane.

5. The hot melt ink composition according to claim 1 , wherein the at least one monomer C is selected from at least one of the group consisting of benzoic acid, 2-methylbenzoic acid, 3-methylbenzoic acid, 4-methylbenzoic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid and 4-methoxybenzoic acid.

6. The hot melt ink composition according to claim 1 , wherein the hot melt ink composition further comprises a copolyester, the copolyester consisting essentially of a condensation product of the first type of monomer and the third type of monomer, wherein the first type of monomer comprises at least one monomer A′, said monomer A′ being a polyhydroxyl alcohol comprising X hydroxyl functional groups, wherein X≧3, and wherein the third type of monomer comprises at least one monomer C′, said monomer C being an aromatic carboxylic acid, and wherein, if X≧4, the third type of monomer comprises at least two monomers C 1 ′ and C 2 ′, said monomers C 1 ′ and C 2 ′ being aromatic carboxylic acids, wherein C 1 ′ is different from and C 2 ′.

7. The hot melt ink composition according to claim 1 , wherein the monomer B is selected from at least one of the group consisting of a dicarboxylic acid and an anhydride of a dicarboxylic acid.

8. The hot melt ink composition according to claim 7 , wherein the first type of monomer is present in a first molar amount n A , the second type of monomer is present in a second molar amount n B and the third type of monomer is present in a third molar amount n C , and wherein the following formula is satisfied:

0.75
<

X
*

n
A

2
⁢

n
B

+

n
C

<

1.25
.

9. The hot melt ink composition according to claim 1 , wherein the monomer B is selected from at least one of the group consisting of a lactone and a hydroxyl carboxylic acid.

10. The hot melt ink composition according to claim 9 , wherein the first type of monomer is present in a first molar amount n A , the second type of monomer is present in a second molar amount n B , n B >0 mole and the third type of monomer is present in a third molar amount n C , and wherein the following formula is satisfied:

0.75
<

X
*

n
A

n
C

<

1.25
.

11. A hot melt ink composition, comprising a copolyester mixture, the copolyester mixture comprising 2 or more of the copolyesters according to claim 8 .

12. A hot melt ink composition, comprising a copolyester mixture, the copolyester mixture comprising 2 or more of the copolyesters according to claim 10 .

13. The hot melt ink composition according to claim 1 , wherein the hot melt ink further comprises a colorant and a high melting crystalline material.

14. A process for preparing a copolyester, the copolyester consisting essentially of a condensation product of a first type of monomer, a second type of monomer and a third type of monomer, wherein the first type of monomer comprises at least one monomer A, said monomer A being a polyhydroxyl alcohol comprising X hydroxyl functional groups, wherein X≧3, wherein the second type of monomer comprises at least one monomer B, said monomer B being selected from the group consisting of a dicarboxylic acid and an anhydride of a dicarboxylic acid, and wherein the third type of monomer comprises at least one monomer C, said monomer C being an aromatic monocarboxylic acids, the process comprising the steps of:
bringing a first molar amount n A of the first type of monomer, a second molar amount n B of the second type of monomer and a third molar amount n C of the third type of monomer under an inert atmosphere in a reactor, provided with a Dean Stark unit, in a ratio Q, wherein Q is defined as:

X
*

n
A

2
⁢

n
B

+

n
C

,

wherein 0.75<Q<1.25;
heating the mixture to 150° C.-250° C., such that the water formed by the condensation reaction is removed from the reaction mixture; and
after the reaction has completed, removing the solvent by distillation.

15. A process for preparing a copolyester, the copolyester consisting essentially of a condensation product of a first type of monomer, a second type of monomer and a third type of monomer, wherein the first type of monomer comprises at least one monomer A, said monomer A being a polyhydroxyl alcohol comprising X hydroxyl functional groups, wherein X≧3, wherein the second type of monomer comprises at least one monomer B, said monomer B being selected from the group consisting of a lactone and a hydroxyl carboxylic acid, and wherein the third type of monomer comprises at least one monomer C, said monomer C being an aromatic monocarboxylic acid, the process comprising the steps of:
bringing a fi

Assignees

• Oce Tech Bv

Inventors

• Groothuijse Ronald
• Van Hameren Richard
• Markies Peter R
• Janssen Marjon M H
• Snijders Emile A

Classifications

• C08G63/80

  Solid-state polycondensation · CPC title

• C08G63/12

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title

• C08L67/00

  Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title

• C09D11/34 Primary

  Hot-melt inks · CPC title