Polyorganosilsesquioxane, hard coat film, adhesive sheet, and laminate

Inactive Publication Date: 2016-10-13
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0033]The polyorganosilsesquioxane according to the present invention has the configuration. Assume that the polyorganosilsesquioxane is incorporated as an essential component into a curable composition, and the curable composition is cured. The curable composition in this case forms a cured product that offers high surface hardness and good heat resistance, is highly flexible, and has excellent processability. The hard coat film according to the present invention has the configuration, is therefore still flexible and is producible and processable by a r

Problems solved by technology

However, due to its poor flexibility and processability, such glass cannot be subjected to production and processing in a roll

Method used

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  • Polyorganosilsesquioxane, hard coat film, adhesive sheet, and laminate
  • Polyorganosilsesquioxane, hard coat film, adhesive sheet, and laminate
  • Polyorganosilsesquioxane, hard coat film, adhesive sheet, and laminate

Examples

Experimental program
Comparison scheme
Effect test

Example

Example 1

[0192]Materials used were 161.5 mmol (39.79 g) of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (hereinafter also referred to as “EMS”), 9 mmol (1.69 g) of phenyltrimethoxysilane (hereinafter also referred to as “PMS”), and 165.9 g of acetone. In a nitrogen stream, the materials were placed in a 300-ml flask (reactor) equipped with a thermometer, a stirrer, a reflux condenser, and a nitrogen inlet tube, followed by temperature rise to 50° C. to give a mixture. To the prepared mixture, was added dropwise 4.70 g (1.7 mmol in terms of potassium carbonate) of a 5% aqueous solution of potassium carbonate over 5 minutes, followed by 1700 mmol (30.60 g) of water added dropwise over 20 minutes. No significant temperature rise occurred during the dropwise additions. The mixture was then subjected to a polycondensation reaction in a nitrogen stream for 4 hours while keeping the temperature at 50° C.

[0193]A product in the reaction mixture after the polycondensation reaction was analyze...

Example

[0195]Examples 2 to 6 and Comparative Examples 1 and 2 Epoxy-containing polyorganosilsesquioxanes were produced each by a procedure similar to that in Example 1, except for changing the amounts of the starting materials (EMS and PMS), the type and amount of the solvent, the reaction temperature, the amount of the 5% potassium carbonate aqueous solution, the amount of water, and the reaction time as given in Table 1. Table 1 presents the number-average molecular weight (Mn), the molecular-weight dispersity, the T3 to T2 ratio of the T3 unit to the T2 unit, and the Td5 of the epoxy-containing polyorganosilsesquioxanes prepared in the examples and comparative examples. The Td5 in Table 1 is indicated in degree Celsius (° C.).

TABLE 1Example 1Example 2Example 3Example 4Example 5Example 6Com. Ex. 1Com. Ex. 2SilsesquioxaneEMS (g)39.7939.7939.7939.7939.7949.2819.7119.71productionPMS (g)1.691.691.691.691.69023.823.8SolventacetonedioxaneacetoneacetoneacetoneacetonedioxaneacetoneSolvent amount...

Example

Example 7

[0197]A solution mixture was prepared as a hard-coating composition (curable composition) by blending 100 parts by weight of the epoxy-containing polyorganosilsesquioxane (S-1) prepared in Example 1, 20 parts by weight of methyl isobutyl ketone (supplied by Kanto Chemical Co., Inc.), and 1 part by weight of a curing catalyst 1 ([diphenyl[4-(phenylthio)phenyl]sulfonium tris(pentafluoroethyl)trifluorophosphate]).

[0198]The above-prepared hard-coating composition was applied onto a PET film (trade name KEB03 W, supplied by Teijin DuPont Films Japan Limited) by flow casting using a wire bar so as to form a hard coat layer having a thickness after curing of 5 μm. The resulting article was left stand in an oven at 70° C. for 10 minutes (for prebaking) and then irradiated with an ultraviolet ray under irradiation conditions at an irradiance of 312 mJ / cm2 and an irradiation intensity of 80 W / cm2. Lastly, the article was subjected to a heat treatment (aging) at 80° C. for 2 hours to ...

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Abstract

Provided is a polyorganosilsesquioxane capable of forming, when cured, a cured product that offers high surface hardness and good heat resistance, is highly flexible, and has excellent processability. The present invention relates to a polyorganosilsesquioxane including a constitutional unit represented by Formula (1). The polyorganosilsesquioxane includes a constitutional unit represented by Formula (I) and a constitutional unit represented by Formula (II) in a mole ratio of the constitutional unit represented by Formula (I) to the constitutional unit represented by Formula (II) of 5 or more. The polyorganosilsesquioxane has a total proportion of the constitutional unit represented by Formula (1) and a constitutional unit represented by Formula (4) of 55% to 100% by mole based on the total amount (100% by mole) of all siloxane constitutional units. The polyorganosilsesquioxane has a number-average molecular weight of 1000 to 3000 and a molecular-weight dispersity (weight-average molecular weight to number-average molecular weight ratio) of 1.0 to 3.0.
[R1SiO3/2]  (1)
[Chem. 2]
[RaSiO3/2]  (I)
[Chem. 3]
[RbSiO(ORc)]  (II)
[Chem. 4]
[R1SiO(ORc)]  (4)

Description

TECHNICAL FIELD[0001]The present invention relates to a polyorganosilsesquioxane, to a curable composition containing the polyorganosilsesquioxane, and to a cured product of the curable composition. The present invention also relates to a hard coat film including a hard coat layer derived from a hard-coating composition (hard-coating agent) containing the polyorganosilsesquioxane. The present invention further relates to a composition (adhesive composition) containing the polyorganosilsesquioxane and to an adhesive sheet and a laminate each prepared using the composition. This application claims priority to Japanese Patent Application No. 2013-257900 filed Dec. 13, 2013 to Japan; to Japanese Patent Application No. 2014-034689 filed Feb. 25, 2014 to Japan; to Japanese Patent Application No. 2014-084592 filed Apr. 16, 2014 to Japan; and to Japanese Patent Application No. 2014-179898 filed Sep. 4, 2014 to Japan. The entire contents of these applications are incorporated herein by refer...

Claims

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Application Information

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IPC IPC(8): C08G77/14B32B7/12C09J7/02C09D183/06C09J183/06C08J7/043C08J7/048
CPCC08G77/14C09D183/06C09J183/06B32B2255/26B32B7/12C09J2483/00B32B2250/02C09J7/02C08L83/06C08J2483/06C08G59/24C08L63/00B32B9/005B32B9/045B32B15/08B32B21/08B32B27/08B32B27/10B32B27/28B32B27/281B32B27/283B32B27/285B32B27/30B32B27/302B32B27/304B32B27/308B32B27/325B32B27/34B32B27/36B32B27/365B32B27/38B32B27/42B32B29/00B32B2250/03B32B2250/04B32B2250/05B32B2307/306B32B2307/412B32B2307/536B32B2307/546B32B2307/732B32B2405/00B32B2457/208C08K5/5415C09J7/20C08J7/0427C08J7/048C08J7/043C08G59/02C08G59/3281C08G59/4064C08K5/549C09D163/00C09J7/30C09J183/04C08G59/68C08G77/08Y10T428/31504Y10T428/31663
Inventor KUWANA, AKIHIROHARADA, NOBUHIKOMASUI, MAYATAKASE, ICHIROMAETANI, SHINJITSUJI, NAOKO
Owner DAICEL CHEM IND LTD
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