Ultraviolet curable silicone composition and cured product of same

Patent metadata

Field	Value
Publication number	US-11827799-B2
Application number	US-202117566260-A
Country	US
Kind code	B2
Filing date	Dec 30, 2021
Priority date	Jun 30, 2016
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

Provided is an ultraviolet curable silicone composition capable of being ejected via inkjet ejection. The composition of the invention is an ultraviolet curable silicone composition comprising:(A) an organopolysiloxane represented by the following general formula (1)wherein each R1 independently represents a group selected from a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, an acryloyl group, a methacryloyl group, an alkyl acrylate group and an alkyl methacrylate group, while the component (A) has per molecule at least two groups selected from an acryloyl group, a methacryloyl group, an alkyl acrylate group and an alkyl methacrylate group; n represents a number satisfying 10≤n≤1,000;(B) a monofunctional (meth)acrylate compound having no siloxane structure; and/or (C) a multifunctional (meth)acrylate compound having no siloxane structure; and(D) a photopolymerization initiator.

First claim

The invention claimed is:

1. A method for ink-jet printing using an ink-jet 3D printer to produce a three-dimensional object of stereolithography, comprising:
ejecting an ultraviolet curable silicone composition via ink-jet ejection using the ink-jet 3D printer;
wherein the ultraviolet curable silicone composition comprises:
(A) 100 parts by mass of an organopolysiloxane represented by the following general formula (1)

wherein each R 1 independently represents a group selected from a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, an acryloyl group, a methacryloyl group, an alkyl acrylate group and an alkyl methacrylate group,
wherein the component (A) has per molecule at least two groups selected from an acryloyl group, a methacryloyl group, an alkyl acrylate group and an alkyl methacrylate group; and wherein n represents a number satisfying 10≤n≤1,000;
(B) a monofunctional (meth)acrylate compound having no siloxane structure,
(C) a multifunctional (meth)acrylate compound having no siloxane structure,
the component (B) and the component (C) being in a total amount of 1 to 500 parts by mass per 100 parts by mass of the component (A), and
(D) a photopolymerization initiator in an amount of 0.1 to 20 parts by mass per 100 parts by mass of the component (A),
and wherein the organopolysiloxane as the component (A) is contained in the composition in an amount of 15 to 80% by mass.

2. The method according to claim 1 , wherein in the general formula (1), n represents a number satisfying 60≤n≤1,000.

3. The method according to claim 1 , wherein in the general formula (1), n represents a number satisfying 20≤n≤500.

4. The method according to claim 1 , wherein in the general formula (1), when R 1 is a monovalent aliphatic hydrocarbon group, it is independently a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.

5. The method according to claim 1 , wherein in the general formula (1), when R 1 is a monovalent aliphatic hydrocarbon group, it is independently a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms.

6. The method according to claim 1 , wherein in the general formula (1), when R 1 is a monovalent aliphatic hydrocarbon group, it is independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and an octyl group.

7. The method according to claim 1 , wherein in the general formula (1), 80% or more of all the R 1 groups are methyl groups.

8. The method according to claim 1 , wherein in the general formula (1), there is a methacrylic acid propyl group or an acrylic acid propyl group at each of the two ends of the molecule.

9. The method according to claim 1 , wherein the component (B) is selected from the group consisting of isoamylacrylate, lauryl acrylate, stearyl acrylate, ethoxy-diethylene glycol acrylate, methoxy-triethylene glycol acrylate, 2-ethylhexyl-diglycol acrylate, phenoxy ethyl acrylate, phenoxydiethylene glycol acrylate, tetrahydrofurfuryl acrylate, isobornyl acrylate, and mixtures thereof.

10. The method according to claim 1 , wherein the component (C) is selected from the group triethylene glycol diacrylate, polytetramethylene glycol diacrylate, neopentyl glycol diacrylate, 1,6-hexanediol diacrylate, dimethylol-tricyclodecane diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, and mixtures thereof.

11. The method according to claim 1 , wherein the component (B) and the component (C) are added in a total amount of 10 to 400 parts by mass, per 100 parts by mass of the component (A).

12. The method according to claim 1 , wherein the ultraviolet curable silicone composition further comprises:
(E) an organopolysiloxane being in an amount of 0.1 to 1,000 parts by mass per 100 parts by mass of the component (A), and represented by the following general formula (2)

wherein each R 2 independently represents a group selected from a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, an acryloyl group, a methacryloyl group, an alkyl acrylate group and an alkyl methacrylate group, while the component (E) has per molecule one group selected from an acryloyl group, a methacryloyl group, an alkyl acrylate group and an alkyl methacrylate group; m represents a number satisfying 10≤m≤1,000.

13. The method according to claim 1 , wherein the component (E) is in an amount of 1 to 100 parts by mass, per 100 parts by mass of the component (A).

14. The method according to claim 1 , wherein the ultraviolet curable silicone composition has a viscosity of not higher than 2,000 mPa·s at 23° C. and has a surface tension of not smaller than 21 mN/m.

15. The method according to claim 1 , wherein the ultraviolet curable silicone composition has a viscosity of not higher than 1,000 mPa·s at 23° C.

16. The method according to claim 1 , wherein the ultraviolet curable silicone composition has a surface tension of not larger than 36 mN/m.

17. The method according to claim 1 , further comprising curing the ultraviolet curable silicone composition to form a cured product.

18. The method according to claim 17 , wherein the curing comprises irradiating with a UVLED lamp, a high-pressure mercury lamp, a super-high pressure mercury lamp, a metal halide lamp, a carbon-arc lamp or a xenon lamp.

Assignees

• Shinetsu Chemical Co

Inventors

• Matsumoto Nobuaki
• Kitagawa Taichi
• Yaginuma Atsushi
• Shirota Masaaki

Classifications

• C09D11/38 Primary

  characterised by non-macromolecular additives other than solvents, pigments or dyes · CPC title

• B29C64/112

  using individual droplets, e.g. from jetting heads · CPC title

• B33Y70/00

  Materials specially adapted for additive manufacturing · CPC title

• B41M5/00

  Duplicating or marking methods; Sheet materials for use therein (by using light-sensitive materials G03; electrography, magnetography G03G {; repeatedly usable boards or tablets for writing or drawing B43L1/00}) · CPC title

• C08F290/06

  Polymers provided for in subclass C08G · CPC title