IP Library Granted Patent US 10,822,298
Granted Patent B2
US 10,822,298 · App. 16/339,584 · Granted Nov 3, 2020

(Meth)acrylic monomer and method for producing same

Inventors: Naoko Tanikawa (Hakusan, JP); Toru Sugiue (Hakusan, JP); Naoki Shima (Hakusan, JP)
Assignee: OSAKA ORGANIC CHEMICAL INDUSTRY LTD.
C07C69/54C07C43/13C07C43/135C07C67/14C07C2601/08
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Quick Facts
Patent No.
US 10,822,298
App. No.
16/339,584
Granted
Nov 3, 2020
Kind
B2
Abstract

A (meth)acrylic monomer is represented by general formula (1) (wherein R 1 represents a hydrogen atom or a methyl group; R 2 to R 4 independently represent —CH 3 or —CH 2 —O—R 5 , wherein at least one of R 2 to R 4 represents —CH 2 —O—R 5 ; R 5 represents an alkyl group having 1 to 4 carbon atoms; and Z represents multiple atoms necessary for the formation of an alicyclic hydrocarbon group having 3 to 10 carbon atoms in conjunction with a carbon atom). The (meth)acrylic monomer has a property of high acid degradability and can be removed by the action of an acid.

Claims (12)

1. A (meth)acrylic monomer represented by general formula (1):

wherein R 1 represents a hydrogen atom or a methyl group; R 2 to R 4 independently represent —CH 3 or —CH 2 —O—R 5 , wherein at least one of R 2 to R 4 represents —CH 2 —O—R 5 ; R 5 represents an alkyl group having 1 to 4 carbon atoms; and Z represents multiple atoms necessary for the formation of an alicyclic hydrocarbon group having 3 to 10 carbon atoms in conjunction with a carbon atom.

2. The (meth)acrylic monomer according to claim 1 , wherein the alicyclic hydrocarbon group is a monocyclic alicyclic hydrocarbon group or monocyclic alicyclic hydrocarbon group having a substituent, a condensed alicyclic hydrocarbon group or condensed alicyclic hydrocarbon group having a substituent, an adamantyl group or adamantyl group having a substituent, a dicyclopentanyl group or dicyclopentanyl group having a substituent, or an isobornyl group or isobornyl group having a substituent.

3. The (meth)acrylic monomer according to claim 2 , wherein the monocyclic alicyclic hydrocarbon group is cyclopentane, cyclohexane, cycloheptane, or cyclooctane.

4. A compound represented by general formula (2):

wherein R 2 to R 4 independently represent —CH 3 or —CH 2 —O—R 5 , wherein at least one of R 2 to R 4 represents —CH 2 —O—R 5 ; R 5 represents an alkyl group having 1 to 4 carbon atoms; and Z represents multiple atoms necessary for the formation of an alicyclic hydrocarbon group having 3 to 10 carbon atoms in conjunction with a carbon atom.

5. A method for producing the (meth)acrylic monomer recited in claim 1 , comprising a step of causing (meth)acrylic acid chloride to react with a compound represented by general formula (2):

wherein R 2 to R 4 independently represent —CH 3 or —CH 2 —O—R 5 , wherein at least one of R 2 to R 4 represents —CH 2 —O—R 5 ; R 5 represents an alkyl group having 1 to 4 carbon atoms; and Z represents multiple atoms necessary for the formation of an alicyclic hydrocarbon group having 3 to 10 carbon atoms in conjunction with a carbon atom.

6. A method for producing the (meth)acrylic monomer recited in claim 2 , comprising a step of causing (meth)acrylic acid chloride to react with a compound represented by general formula (2):

wherein R 2 to R 4 independently represent —CH 3 or —CH 2 —O—R 5 , wherein at least one of R 2 to R 4 represents —CH 2 —O—R 5 ; R 5 represents an alkyl group having 1 to 4 carbon atoms; and Z represents multiple atoms necessary for the formation of an alicyclic hydrocarbon group having 3 to 10 carbon atoms in conjunction with a carbon atom.

7. A method for producing the (meth)acrylic monomer recited in claim 3 , comprising a step of causing (meth)acrylic acid chloride to react with a compound represented by general formula (2):

wherein R 2 to R 4 independently represent —CH 3 or —CH 2 —O—R 5 , wherein at least one of R 2 to R 4 represents —CH 2 —O—R 5 ; R 5 represents an alkyl group having 1 to 4 carbon atoms; and Z represents multiple atoms necessary for the formation of an alicyclic hydrocarbon group having 3 to 10 carbon atoms in conjunction with a carbon atom.

Assignments (2)
CHANGE OF ADDRESS Recorded Apr 15, 2022
From: OSAKA ORGANIC CHEMICAL INDUSTRY LTD.
To: OSAKA ORGANIC CHEMICAL INDUSTRY LTD.
Reel/Frame 059721/0809 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2020
From: TANIKAWA, NAOKO; SUGIUE, TORU; SHIMA, NAOKI
To: OSAKA ORGANIC CHEMICAL INDUSTRY LTD.
Reel/Frame 053257/0923 →