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Curable composition containing fluorine-containing hyperbranched polymer and siloxane oligomer

一种固化性组合物、硅氧烷低聚物的技术，应用在硬涂层的叠层体,硅氧烷低聚物及其制造领域，能够解决固化收缩大、玻璃表面没有密合性、不形成化学键等问题

Active Publication Date: 2015-07-01
NISSAN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the active energy ray-curable composition has a large cure shrinkage and does not form a chemical bond with the glass surface, so it has no adhesion to the glass surface.

Method used

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  • Curable composition containing fluorine-containing hyperbranched polymer and siloxane oligomer
  • Curable composition containing fluorine-containing hyperbranched polymer and siloxane oligomer
  • Curable composition containing fluorine-containing hyperbranched polymer and siloxane oligomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0215] Hereinafter, examples will be given to explain the present invention more specifically, but the present invention is not limited to the following examples.

[0216] In addition, in the examples, the equipment and conditions used for sample preparation and physical property analysis are as follows.

[0217] (1) 13 C NMR spectrum

[0218] Device: JNM-ECA700 manufactured by Nippon Electronics Data Corporation

[0219] Solvent: CDCl 3

[0220] Benchmark: CDCl 3 (77.0ppm)

[0221] (2) Gel Permeation Chromatography (GPC)

[0222] Device: HLC-8220GPC manufactured by Tosei Co., Ltd.

[0223] Column: Showa Denko Co., Ltd. Shodex (registered trademark) GPC KF-804L, GPC KF-805L

[0224] Column temperature: 40℃

[0225] Solvent: Tetrahydrofuran

[0226] Detector: RI

[0227] (3) Determination of glass transition temperature (Tg)

[0228] Installation: Photo-DSC 204 F1 Phoenix (registered trademark) manufactured by NETZSCH

[0229] Measurement conditions: under nitrogen atmosphere

[0230] Heating rate...

Synthetic example 1

[0272] [Synthesis Example 1] Production of fluorine-containing hyperbranched polymer (F-HBP)

[0273] MIBK54g was put into a 300 mL reaction flask, nitrogen was injected for 5 minutes while stirring, and heating was performed until the inner liquid refluxed (about 116°C).

[0274] In another 100 mL reaction flask, 9.0 g (20 mmol) of IPDUA as monomer A, 5.9 g (14 mmol) of C6FA as monomer B, 2.3 g (10 mmol) of MAIB as polymerization initiator C and 54 g of MIBK were added. While stirring, nitrogen was injected for 5 minutes to perform nitrogen replacement, and then cooled to 0°C with an ice bath.

[0275] To the refluxing MIBK in the above 300 mL reaction flask, the contents were dripped over 30 minutes from the above 100 mL reaction flask containing IPDUA, C6FA, and MAIB using a drip pump. After the dropwise addition, it was further stirred for 1 hour.

[0276] Next, after 35 g of MIBK was distilled off from the reaction liquid using a rotary evaporator, it was added to 450 g of hexan...

Synthetic example 2

[0278] [Synthesis Example 2] Production of siloxane oligomer (Si-OLG-1)

[0279] In a 100 mL reaction flask, 11.6 g of MPTES and 7.4 g of ethanol were added and stirred for 5 minutes. In this solution, a mixed solution of 0.04 g of oxalic acid [manufactured by Kanto Chemical Co., Ltd.], 3.2 g of water, and 7.4 g of ethanol separately prepared was added dropwise over 30 minutes. After the solution was stirred for 5 minutes, it was heated until the inner liquid refluxed (approximately 80°C) and stirred for 1 hour. The reaction mixture was cooled to 30°C, and an ethanol solution of Si-OLG-1 was obtained.

[0280] The weight average molecular weight Mw of Si-OLG-1 measured by GPC in terms of polystyrene was 1,200, and the degree of dispersion: Mw / Mn was 1.1.

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Abstract

A curable composition which contains: (a) 100 parts by mass of a siloxane oligomer that has at least one radically polymerizable double bond; (b) 0.001-1 part by mass of a fluorine-containing hyperbranched polymer; (c) 0.01-40 parts by mass of a surface modifying agent that is composed of a perfluoropolyether compound; and (d) 0.1-25 parts by mass of a polymerization initiator that generates radicals by the action of an active energy ray. The fluorine-containing hyperbranched polymer (b) is obtained by polymerizing a monomer (A) that has two or more radically polymerizable double bonds in each molecule and a monomer (B) that has a fluoroalkyl group and at least one radically polymerizable double bond in each molecule in the presence of a polymerization initiator (C) that is in an amount of 5-200 mol% relative to the number of moles of the monomer (A). A cured film which is obtained from this curable composition; and a laminate which has a hard coat layer that is obtained using this curable composition.

Description

Technical field [0001] The present invention relates to a curable composition comprising a fluorine-containing hyperbranched polymer and a siloxane oligomer, and a cured film obtained from the curable composition, and a hard coat layer obtained from the curable composition Laminate, and the siloxane oligomer and its manufacturing method. Background technique [0002] Polymer (polymer) materials have been increasingly used in many fields in recent years. Along with this, corresponding to various fields, the properties of the polymer as a matrix and the characteristics of its surface and interface become important. For example, by using fluorine-based compounds with low surface energy as surface modifiers, water and oil repellency, antifouling properties, non-adhesive properties, releasability, release properties, sliding properties, abrasion resistance, anti-reflection properties, Various proposals have been made to improve the characteristics related to surface and interface co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F30/08B32B27/30C08F2/46C08F290/06C08F299/08C08G77/04C09D4/00C09D7/12C09D183/07
CPCC09D183/04C08F299/08C09D4/00C09D4/06C09D183/10C08G77/20C08F290/06C09D183/02B32B27/30C08G77/442C08F230/08C08F30/08C09D7/12Y10T428/264Y10T428/31612C08F259/08C03C17/30C03C2217/76C03C2217/78C08L83/04C09D151/003
Inventor 原口将幸田村浩康
Owner NISSAN CHEM CORP
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