Triacrylate compounds and methods for producing the same, and compositions

Patent metadata

Field	Value
Publication number	US-10294319-B2
Application number	US-201515521142-A
Country	US
Kind code	B2
Filing date	Oct 21, 2015
Priority date	Oct 22, 2014
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

The invention provides a triacrylate compound represented by the following formula (1). In the formula, each R is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen atom, R1 and R2 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms, and R3 is a linear or branched alkyl group having 1 to 6 carbon atoms or a hydroxymethyl group.

First claim

The invention claimed is:

1. A triacrylate compound represented by formula (1):

wherein each R is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen atom, R 1 and R 2 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms, and R 3 is a linear or branched alkyl group having 1 to 6 carbon atoms or a hydroxymethyl group.

2. A composition comprising the triacrylate compound of claim 1 , and a radical polymerization initiator.

3. The composition of claim 2 , wherein the radical polymerization initiator is a radical photopolymerization initiator.

4. The composition of claim 2 , further comprising at least one member selected from the group consisting of a polymerizable monomer other than the triacrylate compound, and a polymerizable oligomer.

5. The composition of claim 4 , comprising at least one polymerizable oligomer selected from the group consisting of a urethane acrylate oligomer and a urethane methacrylate oligomer.

6. A polymer comprising a structural unit represented by formula (5):

wherein R 1 and R 2 are each independently a linear or branched alkyl group having 1 to 6carbon atoms, R 3 is a linear or branched alkyl group having 1 to 6 carbon atoms or a hydroxymethyl group, each R is independently a hydrogen atom, an alkyl group having 1 to 6carbon atoms or a halogen atom, and each * indicates a binding site of the structural unit in the polymer.

7. A cured product of the composition of claim 2 .

8. An ink comprising the composition of claim 2 .

9. A coating agent comprising the composition of claim 2 .

10. A film comprising a cured product of the composition of claim 2 .

11. An adhesive comprising the composition of claim 2 .

12. A method for producing a triacrylate compound represented by the formula (1), comprising subjecting a polyol compound represented by formula (2) to a dehydration condensation reaction with an unsaturated carboxylic acid compound represented by formula (3 a ),

wherein each R is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen atom, R 1 and R 2 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms, and R 3 is a linear or branched alkyl group having 1 to 6 carbon atoms or a hydroxymethyl group.

13. A method for producing a triacrylate compound represented by formula (1), comprising subjecting a polyol compound represented by formula (2) to a transesterification reaction with an unsaturated carboxylate ester compound represented by formula (3 b ),

wherein each R is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen atom, R 1 and R 2 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms, R 3 is a linear or branched alkyl group having 1 to 6 carbon atoms or a hydroxymethyl group, and Z is an alkyl group having 1 to 6 carbon atoms).

14. The triacrylate compound of claim 1 ,
wherein each R is independently the hydrogen atom or the alkyl group having 1 to 3carbon atoms.

15. The triacrylate compound of claim 1 ,
wherein each R is independently the hydrogen atom or a methyl group.

16. The triacrylate compound of claim 1 ,
wherein R 1 and R 2 are each independently a linear alkyl group having 1 to 4 carbon atoms.

17. The triacrylate compound of claim 1 ,
wherein R 1 and R 2 are each independently a methyl group.

18. The triacrylate compound of claim 1 ,
wherein R 3 is a linear alkyl group having 1 to 6 carbon atoms.

19. The triacrylate compound of claim 1 ,
wherein R 3 is a linear alkyl group having 1 or 2 carbon atoms.

20. The triacrylate compound of claim 1 ,
wherein each R is a hydrogen atom or a methyl group, R 1 and R 2 are each a methyl group, and R 3 is an alkyl group having 1 to 2 carbon atoms.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Yokobori Umi
• Ikeno Taketo
• Sato Hideyuki
• Hasemi Ryuji

Classifications

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• G01R33/46

  NMR spectroscopy · CPC title

• C08F10/00

  Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond · CPC title

• C08F290/067

  Polyurethanes; Polyureas · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title