Ultraviolet ray curable ink composition for use in ink jet method and printed object

Patent metadata

Field	Value
Publication number	US-9732204-B2
Application number	US-201314085466-A
Country	US
Kind code	B2
Filing date	Nov 20, 2013
Priority date	Dec 3, 2012
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

An ultraviolet ray curable ink composition adapted to be ejected by using an ink jet method is provided. The ultraviolet ray curable ink composition includes a polymerizable compound, metal powder, and a polyether based solvent. The metal powder is constituted from metal particles subjected to a surface treatment with a fluorine type silane compound and/or a fluorine type phosphoric acid ester as a surface treatment agent. An amount of the polyether based solvent contained in the ultraviolet ray curable ink composition is in the range of 0.05 mass % or more but 7.0 mass % or less. A printed object is also provided. Such a printed object is produced by using the ultraviolet ray curable ink composition.

First claim

What is claimed is:

1. An ultraviolet ray curable ink composition adapted to be ejected by using an ink jet method, comprising:
a polymerizable compound;
metal powder; and
a polyether based solvent;
wherein the metal powder is constituted from metal particles subjected to a surface treatment with a fluorine-containing surface treatment agent;

wherein the amount of the polyether based solvent contained in the ultraviolet ray curable ink composition is in the range of 0.05 mass % or more but 7.0 mass % or less, and
wherein the fluorine-containing surface treatment agent is at least one selected from the following formulas (1) to (4):
P(O)R n (OH) 3   (1)

where in the above formula (1), “R” is CF 3 (CF 2 ) m (CH 2 ) l — or CF 3 (CF 2 ) m O—, “n” is an integral number in the range of 1 or more but 3 or less, “m” is an integral number in the range of 5 or more but 17 or less, and “l” is an integral number in the range of 1 or more but 12 or less;
CF 3 (CF 2 ) 5 (CH 2 ) 2 P(O)(OH)(OCH 2 CH 3 )  (2);

CF 3 (CF 2 ) 4 (CH 2 ) 2 O—P(O)(OH) 2   (3); or

CF 3 (CF 2 ) 5 (CH 2 ) 2 O—P(O)(OH)(OC 2 H 5 )  (4).

2. The ultraviolet ray curable ink composition as claimed in claim 1 , wherein each of the metal particles of the metal powder is constituted from a base A particle and Al constitutes at least a surface of the base particle, and the metal particle is subjected to the surface treatment with the fluorine-containing surface treatment agent.

3. The ultraviolet ray curable ink composition as claimed in claim 1 , wherein each of the metal particles of the metal powder is of a scaly shape.

4. The ultraviolet ray curable ink composition as claimed in claim 1 , wherein the polymerizable compound includes a monomer having an alicyclic structure.

5. The ultraviolet ray curable ink composition as claimed in claim 4 , wherein the amount of the monomer having the alicyclic structure contained in the ultraviolet ray curable ink composition is in the range of 40 mass % or more but 90 mass % or less.

6. The ultraviolet ray curable ink composition as claimed in claim 4 , wherein the monomer having the alicyclic structure includes a monofunctional monomer having a hetero atom in the alicyclic structure.

7. The ultraviolet ray curable ink composition as claimed in claim 6 , wherein the amount of the monofunctional monomer contained in the ultraviolet ray curable ink composition is in the range of 10 mass % or more but 80 mass % or less.

8. The ultraviolet ray curable ink composition as claimed in claim 4 , wherein the monomer having the alicyclic structure includes one or more selected from the group consisting of tris(2-acryloyloxy ethyl) isocyanurate, dicyclopentenyl oxyethyl acrylate, adamantyl acrylate, γ-butyrolactone acrylate, N-vinyl caprolactam, N-vinyl pyrrolidone, pentamethyl piperidyl acrylate, tetramethyl piperidyl acrylate, 2-methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate, mevalonic acid lactone acrylate, dimethylol tricyclodecane diacrylate, dimethylol dicyclopentane diacrylate, dicyclopentenyl acrylate, dicyclopentanyl acrylate, isobornyl acrylate, cyclohexyl acrylate, acryloyl morpholine and tetrahydrofurfuryl acrylate.

9. The ultraviolet ray curable ink composition as claimed in claim 4 , wherein the polymerizable compound includes one or more selected from the group consisting of phenoxy ethyl acrylate, 2-(2-vinyloxy ethoxy) ethyl acrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, 2-hydroxy-3-phenoxy propyl acrylate and 4-hydroxy butyl acrylate in other than the monomer having the alicyclic structure.

10. The ultraviolet ray curable ink composition as claimed in claim 1 further comprising a substance A having a partial structure represented by the following formula (5),

where in the formula (5), “R 1 ” is an oxygen atom, a hydrogen atom, a hydrocarbon group or an alkoxyl group, and each of “R 2 ”, “R 3 ”, “R 4 ” and “R 5 ” is independently a hydrogen atom or a hydrocarbon group.

11. The ultraviolet ray curable ink composition as claimed in claim 1 , wherein the amount of the polyether based solvent contained in the ultraviolet ray curable ink composition is in the range of 0.06 mass % or more but 6.2 mass % or less.

12. The ultraviolet ray curable ink composition as claimed in claim 1 , wherein the polyether based solvent includes one or more selected from the group consisting of diethylene glycol diethylether, triethylene glycol diethylether, tetraethylene glycol diethylether, triethylene glycol dimethylether, diethylene glycol dipropylether and diethylene glycol methylpropylether,
wherein the polymerizable compound includes one or more selected from the group consisting of γ-butyrolactone acrylate, γ-butyrolactone methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, N-vinyl caprolactam, N-vinyl pyrrolidone, acryloyl morpholine, tris(2-acryloyloxy ethyl) isocyanurate, dicyclopentenyl oxyethyl acrylate, dicyclopentenyl oxyethyl methacrylate, adamantyl acrylate, adamantyl methacrylate, pentamethyl piperidyl methacrylate, tetramethyl piperidyl methacrylate, 2-methyl-2-adamantyl methacrylate, 2-ethyl-2-adamantyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, mevalonic acid lactone methacrylate, dimethylol tricyclodecane diacrylate, dicyclopentanyl acrylate, dicyclopentanyl methacrylate, isobornyl acrylate, isobornyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, dimethylol dicyclopentane diacrylate, phenoxy ethyl acrylate, 2-(2-hydroxy ethoxy) ethyl acrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, 2-hydroxy-3-phenoxy propyl acrylate and 4-hydroxy butyl acrylate,
wherein each of the metal particles of the metal powder is constituted from a base particle and Al constitutes at least a surface of the base particle, and
wherein the fluorine-containing surface treatment agent includes one or more selected from CF 3 (CF 2 ) 5 (CH 2 ) 2 P(O)(OH) 2 , CF 3 (CF 2 ) 5 (CH 2 ) 2 P(O)(OH)(OCH 2 CH 3 ), CF 3 (CF 2 ) 4 (CH 2 ) 2 O—P(O)(OH) 2 or CF 3 (CF 2 ) 5 (CH 2 ) 2 O—P(O)(OH)(OC 2 H 5 ).

13. The ultraviolet ray curable ink composition as claimed in claim 1 , wherein the polyether based solvent includes a compound represented by the following formula (10):
R 1 —O—(CH 2 CH 2 O) n —R 2   (10)

where in the above formula (10), each of “R 1 ” and “R 2 ” independently represents an alkyl group including a carbon number in the range of 1 or more but 4 or less or a hydrogen atom, and “n” is an integral number in the range of 1 or more but 4 or less, wherein in a case where one of the “R 1 ” and “R 2 ” is the hydrogen atom, “n” is an integral number in the range of 2 or more but 4 or less, and wherein in a case where both the “R 1 ” and “R 2” are the hydrogen atom, “n” is 3 or 4.

14. An ultraviolet ray curable ink composition adapted to be ejected by using an ink jet method, comprising:
a polymerizable compound;
metal powder; and
a polyether based solvent;
wherein the metal powder is constituted from metal particles subjected to a surface treatment with a fluorine-containing surface treatment agent represented by CF 3 (CF 2 ) 5 (CH 2 ) 2 P(O)(OH) 2 and/or CF 3 (CF 2 ) 5 (CH 2 ) 2 P(O)(OH)(OCH 2 CH 3 );
wherein the amount of the polyether based solvent contained in the ultraviolet ray curable ink composition is in the range of 0.05 mass % or more but 7.0 mass % or less.

15. An ultraviolet ray curable ink composition adapted to be ejected by using an ink jet method, comprising:
a polymerizable

Assignees

• Seiko Epson Corp

Inventors

• Toyoda Naoyuki
• Hirata Koki
• Ogawa Tomohiro
• Shibatani Masaya
• Terada Masaru
• Takiguchi Hiroshi

Classifications

• C08K5/3435

  Piperidines · CPC title

• C09D11/322

  Pigment inks · CPC title

• Y10T428/24909

  Free metal or mineral containing · CPC title

• C08K5/06 Primary

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• C08K5/56 Primary

  Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond · CPC title