IP Library Granted Patent US 9,371,465
Granted Patent B2
US 9,371,465 · App. 14/371,913 · Granted Jun 21, 2016

Silver ink composition

Inventors: Kumi Hirose (Tokyo, JP); Marina Imai (Tokyo, JP)
Assignee: Toppan Forms Co., Ltd.
C09D11/52C09D11/30C08K5/01C08K5/05C08K5/098C08K5/17
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Quick Facts
Patent No.
US 9,371,465
App. No.
14/371,913
Granted
Jun 21, 2016
Kind
B2
Abstract

A silver ink composition Which includes a silver carboxylate having a group represented by a formula iCOOAg, an aliphatic primary amine or secondary amine having 2 to 10 carbon atoms, an acetylene alcohol represented by a general formula (2) shown below, and a hydrocarbon having 6 to 20 carbon atoms, and has a viscosity at 27° C. of 40 mPa-s or less, in the formula, each of R′ and R″ independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group in which one or more hydrogen atoms may be substituted with a substituent.

Claims (40)

1. A silver ink composition comprising:

a silver carboxylate having a group represented by a formula —COOAg;

an aliphatic primary amine or secondary amine having 2 to 10 carbon atoms;

an acetylene alcohol represented by a general formula (2) shown below; and

a hydrocarbon having 6 to 20 carbon atoms which is at least one selected from the group consisting of a linear or branched saturated hydrocarbon having 10 to 20 carbon atoms, a cyclic saturated hydrocarbon having 6 to 20 carbon atoms, an alkene having 6 to 20 carbon atoms and an alkyne having 6 to 20 carbon atoms;

wherein a viscosity at 27° C. of the composition is 40 mPa·s or less,

wherein each of R′ and R″ independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group in which one or more hydrogen atoms may be substituted with a substituent.

2. The silver ink composition according to claim 1 , wherein the linear or branched saturated hydrocarbon having 10 to 20 carbon atoms is at least one selected from the group consisting of decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane and eicosane.

3. The silver ink composition according to claim 1 , wherein the cyclic saturated hydrocarbon having 6 to 20 carbon atoms is at least one selected from the group consisting of cyclohexane, cycloheptane and cyclooctane.

4. The silver ink composition according to claim 1 , wherein the alkene having 6 to 20 carbon atoms is at least one selected from the group consisting of 1-octene, trans-4-octene and cis-4-octene.

5. The silver ink composition according to claim 1 , wherein the alkene having 6 to 20 carbon atoms is 4-octyne.

6. The silver ink composition according to claim 1 , wherein the linear or branched saturated hydrocarbon having 10 to 20 carbon atoms is at least one selected from the group consisting of decane, dodecane, tetradecane, hexadecane and eicosane.

7. The silver ink composition according to claim 1 , wherein the cyclic saturated having 6 to 20 carbon atoms is one of or both of cyclohexane and cyclooctane.

8. The silver ink composition according to claim 1 , wherein a dynamic surface tension at 27° C. thereof is 56 mN/m or less.

9. The silver ink composition according to claim 1 ,

wherein said silver carboxylate is a silver β-ketocarboxylate represented by the following general formula (1),

wherein R represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more hydrogen atoms may be substituted with a substituent, a phenyl group, a hydroxyl group, an amino group, or a group represented by general formula R 1 —CY 2 —, CY 3 —, R 1 —CHY—, R 2 O—, R 5 R 4 N—, (R 3 O) 2 CY—, or R 6 —C(═O)—CY 2 —;

each Y independently represents a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom; le represents an aliphatic hydrocarbon group having 1 to 19 carbon atoms or a phenyl group; R 2 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms; R 3 represents an aliphatic hydrocarbon group having 1 to 16 carbon atoms; each of R 4 and R 5 independently represents an aliphatic hydrocarbon group having 1 to 18 carbon atoms; and R 6 represents an aliphatic hydrocarbon group having 1 to 19 carbon atoms, a hydroxyl group or a group represented by a formula AgO—;

each X independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, a phenyl group or benzyl group in which one or more hydrogen atoms may be substituted with a substituent, a cyano group, an N-phthaloyl-3-aminopropyl group, a 2-ethoxyvinyl group, or a group represented by general formula R 7 O—, R 7 S—, R 7 —C(═O)— or R 7 —C(═O)—O—; and

R 7 represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a thienyl group, or a phenyl group or diphenyl group in which one or more hydrogen atoms may be substituted with a substituent.

10. The silver ink composition according to claim 9 , wherein said R represents a linear or branched alkyl group, a phenyl group, or a group represented by the general formula R 6 —C(═O)—CY 2 —, and the X represents a hydrogen atom, a linear or branched alkyl group, or a benzyl group.

11. The silver ink composition according to claim 9 , wherein said silver β-ketocarboxylate is at least one selected from the group consisting of silver 2-methylacetoacetate, silver acetoacetate, silver 2-ethylacetoacetate, silver propionylacetate, silver isobutyrylacetate, silver pivaloylacetate, silver 2-n-butylacetoacetate, silver 2-benzylacetoacetate, silver benzoylacetate, silver pivaloylacetoacetate, silver isobutyrylacetoacetate and silver acetonedicarboxylate.

12. The silver ink composition according to claim 1 , wherein an aliphatic hydrocarbon group bonded to a nitrogen atom of said primary amine or secondary amine is a linear or branched alkyl group.

13. The silver ink composition according to claim 1 , wherein said primary amine or secondary amine is at least one selected from the group consisting of 2-ethylhexylamine, n-propylamine, n-butylamine, n-pentyl amine, n-hexylamine, n-heptylamine, n-octylamine, N-methylhexylamine and N-ethylhexylamine.

14. The silver ink composition according to claim 1 , wherein said R′ and R″ are linear or branched alkyl groups having 1 to 10 carbon atoms.

15. The silver ink composition according to claim 1 , wherein said acetylene alcohol is at least one selected from the group consisting of 3,5-dimethyl-1-hexyn-3-ol, 3-methyl-1-butyn-3-ol and 3-methyl-1-pentyn-3-ol.

16. A silver ink composition comprising:

a silver carboxylate having a group represented by a formula —COOAg;

an aliphatic primary amine or secondary amine having 2 to 10 carbon atoms;

an acetylene alcohol represented by a general formula (2) shown below; and

a hydrocarbon having 6 to 20 carbon atoms which is selected from the group consisting of an unsaturated hydrocarbon having a double bond, a linear or branched saturated hydrocarbon having 10 to 20 carbon atoms, and a cyclic saturated hydrocarbon having 6 to 20 carbon atoms;

wherein a viscosity at 27° C. of the composition is 40 mPa·s or less,

wherein each of R′ and R″ independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group in which one or more hydrogen atoms may be substituted with a substituent.

17. A silver ink composition comprising:

a silver carboxylate having a group represented by a formula —COOAg;

an aliphatic primary amine or secondary amine having 2 to 10 carbon atoms;

an acetylene alcohol represented by a general formula (2) shown below; and

a hydrocarbon having 6 to 20 carbon atoms wherein the hydrocarbon is an unsaturated hydrocarbon having a double bond;

wherein a viscosity at 27° C. of the composition is 40 mPa·s or less,

wherein each of R′ and R″ independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group in which one or more hydrogen atoms may be substituted with a substituent.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2024
From: TOPPAN EDGE INC.
To: TOPPAN HOLDINGS INC.
Reel/Frame 067089/0524 →
CHANGE OF NAME Recorded Jun 13, 2023
From: TOPPAN FORMS CO., LTD.
To: TOPPAN EDGE INC.
Reel/Frame 063989/0345 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2014
From: HIROSE, KUMI; IMAI, MARINA
To: TOPPAN FORMS CO., LTD.
Reel/Frame 033298/0174 →
Priority Claims (4)
JP 2012-015581 · Jan 27, 2012 · national
JP 2012-015582 · Jan 27, 2012 · national
JP 2012-284711 · Dec 27, 2012 · national
JP 2012-284712 · Dec 27, 2012 · national
Continuity (1)
Related Publication 20150008376A1 · Jan 8, 2015