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Fluorine-containing polymerizable monomer and polymer compound using same
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A technology of high molecular compounds and polymerizable monomers, which is applied in organic chemistry and other fields, and can solve the problems of unreported use of fluorine-containing polymerizable monomers
Inactive Publication Date: 2014-02-19
CENT GLASS CO LTD
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[0006] However, for fluorine-containing compounds obtained by adding HFIP groups to aromatic polyesters, there are reported examples of phenolic derivatives containing HFIP groups (see Non-Patent Document 2), but the substitution of HFIP groups in the aromatic ring has not been carried out. Detailed analysis such as position identification, etc., did not report polymers obtained by using fluorine-containing phenols as fluorine-containing polymerizable monomers.
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Embodiment 1
[0182] Synthesis of the fluorine-containing polymerizable monomer shown in embodiment 1 (formula (3) )
[0183] As shown in the following reaction formula, the polyhydric phenol represented by the formula (15) is reacted with hexafluoroacetone to synthesize the fluorine-containing polymerizable monomer represented by the formula (3), that is, 2,6-bis(1,1, 1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-1,5-binaphthol.
[0184]
[0185] At room temperature (20°C), 150 g of toluene was added to a stainless steel autoclave, and 25 g (0.54 mol) of 1,5-binaphthol, a polyhydric phenol represented by the general formula (15), was added as a raw material, and 0.25 g of CH 3 SO 3 H. Next, 57 g (0.34 mol) of hexafluoroacetone was added to the autoclave, and then the temperature was raised slowly, and the mixture was reacted for 8 hours while stirring while maintaining the temperature at 100°C.
[0194] In a reaction vessel equipped with a stirring device, 1.97 g (0.004 mol) of a fluorine-containing polymerizable monomer represented by formula (3) was dissolved in 12.9 g of N-methylpyrrolidone and 0.70 g of pyridine purified by dehydration. Next, 1.72 g (0.004 mol) of 2,2-bis(4-carbonylchlorophenyl)-hexafluoropropane was added, stirred at room temperature for 5 hours, and polycondensation reaction was performed.
[0195] After completion of the reaction, a polymer (2.94 g, yield 80%) including a repeating unit of formula (18) was obtained by the same operation as in Example 1.
[0196]
Embodiment 3
[0198] In a reaction vessel equipped with a stirring device, 1.97 g (0.004 mol) of a fluorine-containing polymerizable monomer represented by formula (3) was dissolved in 12.9 g of N-methylpyrrolidone and 0.70 g of pyridine purified by dehydration. Next, 1.18 g (0.004 mol) of 3,3',4,4'-biphenyltetracarboxylic dianhydride was added, stirred at room temperature for 5 hours, and polycondensation reaction was carried out.
[0199] After completion of the reaction, a polymer (2.67 g, yield 85%) including a repeating unit of formula (19) was obtained by the same operation as in Example 1.
[0200]
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Abstract
A fluorine-containing polymerizable compound represented by general formula (1) can be obtained by the present invention. In formula (1), each of a and b independently represents an integer of 0-2, and a + b = 2; c represents an integer of not less than 0; and each of d and e independently represents an integer of 0-2, and 1 = d + e = 4. Also in formula (1), the moiety represented by formula (AA) may contain a nitrogen atom, an oxygen atom or a sulfur atom as a heteroatom by which a carbon atom is substituted. A polymer compound which is obtained using the fluorine-containing polymerizable compound has hydrophilicity and transparency in addition to low water absorption of a fluorine compound.
Description
technical field [0001] The present invention relates to a fluorine-containing polymerizable monomer useful as a material for resist materials used in photolithography in semiconductor manufacturing, coating materials for flat panel displays, protective films for electronic circuit substrates, protective films for semiconductors, etc. and polymer compounds using the same. Background technique [0002] Bisphenol is useful as a raw material for engineering plastics. In addition, polymers using bisphenol are used in electronic components, and are used in a wide range of applications such as water treatment, gas separation, and separation membranes for hemodialysis. However, polyesters containing repeating units formed from bisphenols are difficult to dissolve in organic solvents and difficult to mold. [0003] Therefore, in order to improve the solubility for organic solvents, it is disclosed to use hexafluoroisopropylidene group in the chemical structure, namely -C(CF 3 ) 2...
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