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Fluoroacrylic compound, fluorine-containing actinic-ray-curable composition, and article

A technology of acrylic acid and compound, applied in the direction of coating, etc., can solve the problems of surface consumption of hard coating, decrease of antifouling property, etc.

Pending Publication Date: 2022-02-01
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, in recent years, the use of hard coats containing fluorine-containing compounds tends to increase for touch panels and other articles that are easily touched by human fingers. When the existing fluorine-containing compounds are used for this application, the surface of the hard coat It is worn out due to the abrasion of human fingers, and the stain resistance is reduced, so it does not have the abrasion resistance that is practically satisfactory.

Method used

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  • Fluoroacrylic compound, fluorine-containing actinic-ray-curable composition, and article
  • Fluoroacrylic compound, fluorine-containing actinic-ray-curable composition, and article
  • Fluoroacrylic compound, fluorine-containing actinic-ray-curable composition, and article

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0273] Synthesis examples, examples, and comparative examples are shown below to specifically describe the present invention, but the present invention is not limited by the following examples.

Synthetic example 1

[0274] [Synthesis Example 1] Synthesis of Fluorine-Containing Acrylic Compound (A)

[0275] Under a dry nitrogen atmosphere, put into a 2000mL three-necked flask equipped with a reflux device and a stirring device by the following formula

[0276] CH 2 =CH-CH 2 -O-CH 2 -Rf'-CH 2 -O-CH 2 -CH=CH 2

[0277] Rf': -CF 2 O(CF 2 O) p1 (CF 2 CF 2 O) q1 CF 2 -

[0278] (q1 / p1=0.9, p1+q1≒45, by 19 Number average molecular weight calculated by F-NMR≒4300)

[0279] 500 g (0.12 mol) of the indicated perfluoropolyether, 700 g of hexafluoro-m-xylene, and 361 g (1.50 mol) of tetramethylcyclotetrasiloxane were heated to 90° C. while stirring. 0.442 g of a toluene solution of platinum / 1,3-divinyl-tetramethyldisiloxane complex (in terms of Pt, containing 1.1×10 -6 mol), stirring was continued for 4 hours while maintaining the internal temperature above 90°C. use 1 After confirming the disappearance of the allyl group of the raw material by H-NMR, the solvent and excess tetrame...

Synthetic example 2

[0289] [Synthesis Example 2] Synthesis of Fluorine-Containing Acrylic Compound (B)

[0290] Under a dry nitrogen atmosphere, put in a 1000mL three-necked flask equipped with a reflux device and a stirring device

[0291] CH 2 =CH-CH 2 -O-CH 2 -Rf"-CH 2 -O-CH 2 -CH=CH 2

[0292] Rf": -CF 2 O(CF 2 O) p2 (CF 2 CF 2 O) q2 CF 2 -

[0293] (q2 / p2=1.3, p2+q2≒16, by 19 Number average molecular weight calculated by F-NMR≒1800)

[0294] 188 g (0.10 mol) of the indicated perfluoropolyether, 188 g of hexafluoro-m-xylene, and 361 g (1.50 mol) of tetramethylcyclotetrasiloxane were heated to 90°C while stirring. 0.442 g of a toluene solution of platinum / 1,3-divinyl-tetramethyldisiloxane complex (in terms of Pt, containing 1.1×10 -6mol), stirring was continued for 4 hours while maintaining the internal temperature at 90°C or higher. use 1 After confirming the disappearance of the allyl group of the raw material by H-NMR, the solvent and excess tetramethylcyclotetrasiloxane ...

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Abstract

A fluoroacrylic compound of formula (1) which, when added to an actinic-ray-curable composition, can impart excellent liquid repellency, antifouling properties, and wear resistance. (1) Y-Rf1-Z1-Q1-[Z2-X]a [Rf1 is a divalent perfluoropolyether group. Z1 is a divalent hydrocarbon group optionally containing O, N, or Si. Q1 is an (a+1)-valent linking group including a+1 or more Si atoms. Z2 is a divalent alkylene ether group. X is H or a monovalent organic group having an (alpha-substituted) acryl group, and at least one of the X moieties is a monovalent organic group having an (alpha-substituted) acryl group. Symbol a is 1-10. Y is F or -Z1-Q1-[Z2-X]a. All of the Z1 moiety and the a Z2 moieties within the [ ] have been bonded to the Si atoms contained in the Q1 and the molecule has no urethane bond therein.].

Description

technical field [0001] The present invention relates to a fluorine-containing acrylic compound capable of imparting excellent liquid repellency, stain resistance, and abrasion resistance by adding it to an active energy ray-curable composition such as ultraviolet rays and electron beams, and to a fluorine-containing acrylic compound having the same The fluorine-containing active energy ray-curable composition and an article having a cured product layer of the composition on the surface of the substrate. Background technique [0002] Conventionally, as a means to protect the surface of a resin molded body or the like, hard coat treatment has generally been widely used. This is to form a hard cured resin layer (hard coat layer) on the surface of the molded body so that it is hard to be damaged. As the material constituting the hard coat layer, curable compositions using active energy rays, such as thermosetting resins, ultraviolet-ray or electron beam-curable resins, are wide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/332C08G65/336C09D7/65
CPCC08G65/3322C08G65/336C09D7/65C08G2650/04C09D201/04C09D5/1637C08F290/062C09D4/06C08J7/0427C08J7/046C08J2369/00C08J2433/04C08J2471/00C08F2/50C08F222/104C08F220/24C08F2/48C08G65/007C09D133/14C09D133/16
Inventor 森圣矢坂野安则
Owner SHIN ETSU CHEM IND CO LTD