Active-energy-ray-curable composition, active-energy-ray-curable ink composition, composition stored container, two-dimensional or three-dimensional image forming apparatus, method for forming two-dimensional or three-dimensional image, cured product, and laminated cured product

Patent metadata

Field	Value
Publication number	US-10995226-B2
Application number	US-201615184477-A
Country	US
Kind code	B2
Filing date	Jun 16, 2016
Priority date	Jun 22, 2015
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

An active-energy-ray-curable composition including at least one monofunctional (meth)acrylate, at least one multifunctional (meth)acrylate, and at least one chlorinated-olefin-structure-containing polymer.

First claim

What is claimed is:

1. An active-energy-ray-curable composition comprising:
at least one monofunctional (meth)acrylate selected from the group consisting of t-butyl acrylate, t-butyl methacrylate, n-pentyl methacrylate, and n-hexyl methacrylate;
at least one multifunctional (meth)acrylate selected from the group consisting of ethyleneoxide-modified trimethylolpropane trimethacrylate, ethyleneoxide-modified trimethylolpropane triacrylate, caprolactone-modified dipentaerythritolhexaacrylate, and tricyclodecane dimethanol diacrylate;
at least one chlorinated-olefin-structure-containing polymer having a weight average molecular weight of 40,000 or less; and
at least one polymerization initiator,
wherein the at least one monofunctional (meth)acrylate is included in an amount of from 50 to 85 parts by mass, the at least one multifunctional (meth)acrylate is included in an amount of from 15 to 50 parts by mass, and the at least one chlorinated-olefin-structure-containing polymer is included in an amount of from 0.05 to 10 parts by mass, relative to 100 parts by mass of total monomer components,
the at least one multifunctional (meth)acrylate does not comprise glycerol dimethacrylate, and
the at least one polymerization initiator is included in an amount of from 8.26 to 8.3 wt % based on 100 wt % of the active-energy-ray-curable composition.

2. The active-energy-ray-curable composition according to claim 1 ,
wherein the at least one chlorinated-olefin-structure-containing polymer has a rate of chlorination of 10% by mass to 50% by mass.

3. A composition stored container comprising:
the active-energy-ray-curable composition according to claim 1 ; and
a container storing the active-energy-ray-curable composition.

4. A two-dimensional or three-dimensional image forming apparatus comprising:
a storing part storing the active-energy-ray-curable composition of claim 1 ; and
an irradiating unit configured to irradiate the active-energy-ray-curable composition with active energy rays.

5. A method for forming a two-dimensional or three-dimensional image, the method comprising
irradiating the active-energy-ray-curable composition according to claim 1 with active energy rays.

6. The method for forming a two-dimensional or three-dimensional image according to claim 5 ,
wherein the two-dimensional or three-dimensional image is formed on a polypropyrene substrate that is not surface-treated.

7. A cured product, which is obtained by irradiating the active-energy-ray-curable composition according to claim 1 with active energy rays to cure the active-energy-ray-curable composition.

8. The cured product according to claim 7 ,
wherein the cured product has close adhesiveness of 1 kPa or more to a polypropyrene substrate that is not surface-treated.

9. A laminated cured product comprising:
a first layer; and
a second layer disposed on the first layer,
wherein the first layer is made of the active-energy-ray-curable composition of claim 1 , and the second layer is made of a composition comprising diethylene glycol dimethacrylate.

10. The laminated cured product according to claim 9 ,
wherein an average thickness of the first layer is 3 μm or more, an average thickness of the second layer is 10 μm or more, and a ratio of the average thickness of the first layer to a total average thickness of the first layer and the second layer is 15% or more.

11. The laminated cured product according to claim 9 ,
wherein the laminated cured product is formed on a polypropyrene substrate that is not surface-treated.

12. The laminated cured product according to claim 9 ,
wherein the laminated cured product has close adhesiveness of 10 kPa or more to a polypropyrene substrate, and the laminated cured product has higher surface intensity than a polypropyrene substrate that is not coated with the laminated cured product.

13. A method for forming a laminated cured product, the method comprising:
applying the active-energy-ray-curable composition of claim 1 onto a substrate;
irradiating the active-energy-ray-curable composition with active energy rays such that the active-energy-ray-curable composition is cured and a first layer is formed on the substrate; and
applying a composition comprising diethylene glycol dimethacrylate on the first layer such that a second layer disposed on the first layer is formed,
wherein the substrate is a polypropyrene substrate that is not surface-treated.

14. The method according to claim 13 ,
wherein an average thickness of the first layer is 5 μm to 13 μm, an average thickness of the second layer is 10 μm to 25 μm, and a ratio of the average thickness of the first layer to a total average thickness of the first layer and the second layer is 28.6% to 34.7%.

15. An active-energy-ray-curable composition comprising:
at least one monofunctional (meth)acrylate;
at least one multifunctional (meth)acrylate;
at least one chlorinated-olefin-structure-containing polymer having a weight average molecular weight of 40,000 or less; and
at least one polymerization initiator,
wherein the at least one polymerization initiator is included in an amount of from 5 to 10 parts by mass, relative to 100 parts by mass of total monomer components, and in an amount of from 8.26 to 8.3 wt % based on 100 wt % of the active-energy-ray-curable composition, and
the active-energy-ray-curable composition does not comprise glycerol dimethacrylate.

16. The active-energy-ray-curable composition according to claim 15 ,
wherein the at least one monofunctional (meth)acrylate and the at least one multifunctional (meth)acrylate are negative in skin sensitization.

17. The active-energy-ray-curable composition according to claim 16 ,
wherein the at least one monofunctional (meth)acrylate, the at least one multifunctional (meth)acrylate, or both, has a Stimulation Index (SI value) of less than 3, where the Stimulation Index indicates a degree of skin sensitization measured by a skin sensitization test (LLNA method) on the at least one monofunctional (meth)acrylate, the at least one multifunctional (meth)acrylate, or both.

18. The active-energy-ray-curable composition according to claim 15 ,
wherein the at least one chlorinated-olefin-structure-containing polymer has a chlorination rate of from 10% by mass to 50% by mass.

19. An active-energy-ray-curable ink composition comprising
the active-energy-ray-curable composition according to claim 1 .

20. The active-energy-ray-curable ink composition according to claim 19 ,
wherein a viscosity of the active-energy-ray-curable ink composition at 25° C. is 5 mPa·s or more but 18 mPa·s or less.

21. The active-energy-ray-curable ink composition according to claim 19 , consisting of:
the at least one monofunctional (meth)acrylate;
the at least one multifunctional (meth)acrylate;
the at least one chlorinated-olefin-structure-containing polymer;
the at least one polymerization initiator;
optionally at least one organic solvent; and
optionally at least one other component selected from the group consisting of surfactants, polymerization inhibitors, leveling agents, defoaming agents, fluorescent brighteners, permeation enhancing agents, wetting agents (humectants), fixing agents, viscosity stabilizers, fungicides, preservatives, antioxidants, ultraviolet absorbents, chelate agents, pH adjusters (regulators), and thickeners.

Assignees

• Iio Masato
• Hiraoka Takao
• Ricoh Co Ltd

Inventors

• Iio Masato
• Hiraoka Takao

Classifications

• C08F220/1806

  C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate · CPC title

• C08F220/1805

  C5-(meth)acrylate, e.g. pentyl (meth)acrylate · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C09D11/10

  based on artificial resins · CPC title

• B33Y10/00

  Processes of additive manufacturing · CPC title