Fluorine-based surfactant, and coating composition and resist composition each using same

A technique for surfactants and compositions, which is applied in the field of coating compositions and resist compositions using the surfactants, can solve problems such as difficulty in maintaining the performance of surfactants, and achieve excellent leveling and excellent reduction , the effect of high surface smoothness

Active Publication Date: 2013-03-13
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as mentioned above, there is a problem that it is difficult to maintain the performance as a surfactant as the chain length becomes shorter.

Method used

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  • Fluorine-based surfactant, and coating composition and resist composition each using same
  • Fluorine-based surfactant, and coating composition and resist composition each using same
  • Fluorine-based surfactant, and coating composition and resist composition each using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0132] Examples and comparative examples are given below to describe the present invention in further detail. In addition, in the following examples, the weight average molecular weight (Mw) and the number average molecular weight (Mn) were calculated|required by GPC measurement under the following conditions.

[0133] [GPC measurement conditions]

[0134] Measuring device: "HLC-8220GPC" manufactured by TOSOH Corporation,

[0135] Column: Guard column "HHR-H" manufactured by TOSOH Corporation (6.0mmI.D.×4cm)

[0136] + "TSK-GEL GMHHR-N" manufactured by TOSOH Corporation (7.8mmI.D.×30cm)

[0137] + "TSK-GEL GMHHR-N" manufactured by TOSOH Corporation (7.8mmI.D.×30cm)

[0138] + "TSK-GEL GMHHR-N" manufactured by TOSOH Corporation (7.8mmI.D.×30cm)

[0139] + "TSK-GEL GMHHR-N" manufactured by TOSOH Corporation (7.8mmI.D.×30cm)

[0140] Detector: ELSD ("ELSD2000" manufactured by Ortec Ltd.)

[0141] Data processing: "GPC-8020Model II data analysis version 4.30" manufactured by...

Synthetic example 1）

[0163] Into a glass flask equipped with a stirring device, a thermometer, a condenser, and a dropping device, add 20 parts by mass of a perfluoropolyether compound having hydroxyl groups at both ends represented by the following formula (a2-1-1), and diisocyanate as a solvent. 20 parts by mass of propyl ether, 0.02 parts by mass of p-methoxyphenol as a polymerization inhibitor, and 3.1 parts by mass of triethylamine as a neutralizing agent. Stirring was started under air flow, and the inside of the flask was kept at 10°C. 2.7 parts by mass of acryloyl chloride were added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred at 10° C. for 1 hour, heated and stirred at 30° C. for 1 hour, then heated to 50° C. and stirred for 10 hours to perform a reaction, and the disappearance of acryloyl chloride was confirmed by gas chromatography. Next, after adding 40 parts by mass of diisopropyl ether as a solvent, washing by mixing and stirring 80 parts ...

Synthetic example 2）

[0170] Add 30 parts by mass of a block copolymer of ethylene oxide and propylene oxide represented by the following formula (B1'-1) and 2.8 parts by mass of acrylic acid into a glass flask equipped with a stirring device, a thermometer, a condenser tube, and a dropping device parts, 64 parts by mass of toluene as a solvent, 0.03 parts by mass of phenothiazine as a polymerization inhibitor, and 0.6 parts by mass of methanesulfonic acid as a catalyst. Stirring was started under air flow, heated to 120° C., and refluxed for dehydration. After confirming that 0.63 parts by mass of dehydration was present, it was cooled to 65°C and neutralized with triethylamine. After neutralization, the temperature was raised to 85°C, 2.3 parts by mass of ion-exchanged water was added, liquid separation was performed, and the lower layer was separated. The washing operation was repeated until the pH of the lower layer was measured to be 7 or higher. After cooling to 30° C., it was diluted with t...

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Abstract

Disclosed is a fluorine-based surfactant which is composed of a copolymer that is obtained by copolymerizing, as essential monomers, (A) a polymerizable monomer that has a poly(perfluoroalkylene ether) chain and a polymerizable unsaturated group at each end of the chain and (B) a polymerizable monomer that has an oxyalkylene group and a polymerizable unsaturated group. Because of the structure thereof, the fluorine-based surfactant does not produce PFOS or PFOA that is highly accumulative in the environment or in a living organism. In addition, the fluorine-based surfactant exhibits more excellent surface tension lowering ability even with a lower fluorine content in comparison to surfactants that have a fluorinated alkyl group with 8 or more carbon atoms. Consequently, the fluorine-based surfactant is suitable for use as a leveling agent for a coating composition, a resist composition and the like.

Description

technical field [0001] The invention relates to a leveling agent that can be used as a leveling agent for various coating materials and anti-corrosion materials in the field of various coatings requiring surface smoothness, or in the field of coatings requiring precision coating, and has low accumulation to the environment and organisms The fluorine-containing surfactant, and further relates to the coating composition and the resist composition using the surfactant. Background technique [0002] Conventionally, in various coating fields, various surfactants called leveling agents such as hydrocarbon-based, silicone-based, and fluorine-based surfactants have been used for the purpose of improving the homogeneity and smoothness of the obtained coating film. Among them, fluorine-based surfactants are widely used because of their high ability to reduce surface tension and less pollution after coating. [0003] As such a fluorine-based surfactant, a method using a polymer having...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K3/00C08F290/06C09D7/12C09D201/00G03F7/004C09D7/47
CPCC09D7/06G03F7/0048C09D11/101C08F222/20G03F7/0046C08F283/065C08F290/04C08F290/062C08F291/04C09D7/47C08F220/288C08F222/1063C08F220/287C08F220/286C08F220/1811C08F222/185C09D7/40C09D201/00G03F7/0045G03F7/032C08F222/205
Inventor 笹本慎铃木秀也
Owner DIC CORP
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