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Silicone compound having a radical-polymerizable group and a method for the preparation thereof

A technology of siloxane compounds and polymerizable groups, which is applied in the fields of compounds of Group 4/14 elements of the periodic table, chemical instruments and methods, and medical preparations containing active ingredients, etc. Good handling properties, excellent oxygen permeability, and good reactivity

Active Publication Date: 2016-04-27
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, TRIS-A is solid at room temperature (melting point: about 50°C), and has a problem of poor handling

Method used

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  • Silicone compound having a radical-polymerizable group and a method for the preparation thereof
  • Silicone compound having a radical-polymerizable group and a method for the preparation thereof
  • Silicone compound having a radical-polymerizable group and a method for the preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Add 0.1 mol of siloxane-containing amine of the following formula (I), 200 ml of hexane, and 170 g of 10% sodium carbonate water to a flask equipped with a thermometer, a dropping funnel, and a nitrogen gas introduction tube, and stir at 5° C. 1.2 mol of acryloyl chloride was added dropwise.

[0112] [chem 21]

[0113]

[0114] After the dropwise addition, stirring was continued at room temperature for 5 hours, and then the organic layer was washed with pure water. Next, 0.008 g of p-methoxyphenol (polymerization inhibitor) was added to the washed solution, and the volatile components were distilled off under reduced pressure (60°C, 5 torr) to obtain a light yellow transparent liquid at room temperature (25°C). product. use 1 As a result of identification by H-NMR measurement, it was a compound represented by the following formula (II). The yield was 96.9%.

[0115] [chem 22]

[0116]

[0117] Shown below 1 H-NMR spectrum.

[0118] 1 H-NMR (400MHz, CDCl 3 ...

Embodiment 2

[0120] The method of Example 1 was repeated except that the compound represented by the following formula (III) was used instead of the compound represented by the above formula (I), and a light yellow transparent liquid product was obtained at room temperature (25° C.).

[0121] [chem 23]

[0122]

[0123] use 1 As a result of identification by H-NMR measurement, it was a siloxane compound represented by the following formula (IV). The yield was 97.3%.

[0124] [chem 24]

[0125]

[0126] Shown below 1 H-NMR spectrum.

[0127] 1 H-NMR (400MHz, CDCl 3 ): δ0.00(s,6H), 0.07(s,36H), 0.34~0.48(m,4H), 1.49~1.67(m,4H), 3.18~3.39(m,4H), 5.62(dd,1H ), 6.32 (ddd, 1H), 6.53 (dd, 1H).

Embodiment 3

[0129] Except for using 2-acryloyloxyethyl isocyanate instead of acryloyl chloride, the method of Example 1 was repeated to obtain a pale yellow transparent liquid product at room temperature (25° C.). use 1 As a result of H-NMR measurement and identification, it was a siloxane compound represented by the following formula (V). The yield was 95.2%.

[0130] [chem 25]

[0131]

[0132] Shown below 1 H-NMR spectrum.

[0133] 1 H-NMR (400MHz, CDCl 3 ): δ0.07(s,54H), 0.34~0.45(m,4H), 1.49~1.68(m,4H), 3.08~3.20(m,4H), 3.49~3.59(m,2H), 4.18~4.28 (m, 2H), 4.72 (br, 1H), 5.82 (dd, 1H), 6.15 (ddd, 1H), 6.39 (dd, 1H).

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PUM

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Abstract

The present invention provides a radical-polymerizable group-containing silicone compound which is liquid at room temperature and has good handling properties, has excellent reactivity and provides a cured product having an excellent oxygen permeability. Thus, the present invention provides a silicone compound represented by the following formula (1): wherein A is, independently of each other, a substituted or unsubstituted, linear or branched, divalent hydrocarbon group having 1 to 6 carbon atoms; B is, independently of each other, a monovalent organosilicone residue having 2 to 20 silicon atoms; and X is a monovalent radical-polymerizable group or a monovalent group comprising said monovalent radical-polymerizable group. Further, the present invention provides a method for preparing the silicone compound.

Description

technical field [0001] The present invention relates to a siloxane compound having a radical polymerizable group at the end and a method for producing the same. Specifically, it relates to a siloxane compound having excellent oxygen permeability and good handleability at room temperature, and a method for producing the same. Background technique [0002] Silicone hydrogels used as contact lens materials have been developed in the past, and siloxanes with polymerizable groups are used as raw materials for the purpose of improving oxygen permeability, imparting flexibility to lenses, and improving mechanical strength. Compound (polydimethylsiloxane) (Non-Patent Document 1). For example, U.S. Patent No. 3,808,178 (Patent Document 1) describes 3-[tris(trimethylsiloxy)silyl]propylmethacrylic acid as a siloxane monomer used in ophthalmic devices Esters (TRIS). Since a silicone hydrogel is obtained by copolymerizing a hydrophilic monomer and a polymerizable silicone compound, it...

Claims

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Application Information

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IPC IPC(8): C07F7/18C08G77/26
CPCC07F7/1892G02B1/041G02B1/043A61K8/898C08G77/54C09D183/14C08G77/20C08G77/485A61Q19/00A61K2800/10C07F7/0838C07F7/1804C07F7/0889C08F230/085C08L83/04
Inventor 后藤智幸
Owner SHIN ETSU CHEM IND CO LTD
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