JP6448367B2 - フッ素化撥水撥油剤 - Google Patents
フッ素化撥水撥油剤 Download PDFInfo
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- JP6448367B2 JP6448367B2 JP2014536175A JP2014536175A JP6448367B2 JP 6448367 B2 JP6448367 B2 JP 6448367B2 JP 2014536175 A JP2014536175 A JP 2014536175A JP 2014536175 A JP2014536175 A JP 2014536175A JP 6448367 B2 JP6448367 B2 JP 6448367B2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 19
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- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 239000002216 antistatic agent Substances 0.000 description 1
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- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 230000001680 brushing effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
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- 239000002537 cosmetic Substances 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000001523 electrospinning Methods 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- AJURYMCOXVKKFB-UHFFFAOYSA-M trimethyl(3-prop-2-enoyloxypropyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCOC(=O)C=C AJURYMCOXVKKFB-UHFFFAOYSA-M 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/147—Polyurethanes; Polyureas
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/2885—Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen atoms
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
- C08G18/5015—Polyethers having heteroatoms other than oxygen having halogens having fluorine atoms
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/68—Unsaturated polyesters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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- Wood Science & Technology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
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- Polyurethanes Or Polyureas (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Description
−(C(=O)CuH2uO)t− 式(1)
を含む部分(a1)であり、式中、uは、2〜5、好ましくは3〜5の整数であり、tは、1〜20、より典型的には1〜10、好ましくは1〜5、最も典型的には1〜3の整数である。部分(a1)は、通常、(ポリ)γ−(ガンマ)ブチロラクトン部分、(ポリ)δ−(デルタ)バレロラクトン部分及び/又は(ポリ)ε−(イプシロン)カプロラクトン部分から選択される。好ましいのは、(ポリ)ε(イプシロン)−カプロラクトン部分であり、より詳細には、ポリε(イプシロン)−カプロラクトン部分である。
−(C(=O)CuH2uO)t− 式(1)
式中、u及びtは、上で指定された整数である。本発明の全体を通して、特に断らなければ、「イソシアナート基と反応できる反応性基」は、通常、ヒドロキシル基を意味する。別の可能な基は、アミノ又はチオール基である。ヒドロキシル基が好ましい。この部類で好ましいのは、特に、ヒドロキシC1−4アルコキシ(メタ)アクリラート−((ポリ)ラクトン)tに由来する部分(a1’)であり、式中、tは1〜20、好ましくは1〜10、最も好ましくは1〜5の整数である。好ましくは、(ポリ)ラクトンは、(ポリ)カプロラクトンである。
CH2=CH(R)−C(=O)−O−(CnH2n)r−O−(C(=O)−C5H10O)t−H
式中、Rは、−H又は−CH3であり、nは、1〜4の整数であり、rは、1〜4の整数であり、tは、1〜20、好ましくは1〜10、より典型的には1〜5の整数である。部分(a1’)を供給し得る適切な化合物の例については−後述の化合物(iii)を参照されたい。
−(CF2CF2O)p− 式(3)
−(CF2CF(CF3)O)q− 式(4)
−(CF2CF2CF2O)r− 式(5)
−(CF2O)s− 式(6)
−(CkF2k+1)− 式(7)
式中、kは、1〜16の整数であり、
p、q、r及びsの各々は、1〜100、好ましくは1〜80の整数である。p、q、r及びsの各々が、上の範囲内にある時、硬化後のコーティング膜の表面は、撥水及び/又は撥油性に優れ、優れた指紋除去性が、長期に渡って保たれるであろう。上で指定された式(3)〜(6)の1つ又は複数によって表される少なくとも1個の小部分を含む部分(a3)が、より一層好ましい。
−NCO末端(ポリ)ウレタンプレポリマーを形成するための、少なくとも1種のフッ素化アルコール(化合物i)と少なくとも1種のポリイソシアナート(化合物ii)との反応を含む、第1ステップ、及び
−第1ステップの生成物と、少なくとも1個の活性エネルギー線硬化性基及びイソシアナート基と反応できる少なくとも1個(好ましくは、本質的に1種)の反応性基を含有する少なくとも1種の(ポリ)ラクトン−修飾化合物(iii)との反応を含む第2ステップ、を含む方法により得られる。代わりに、第1ステップが、少なくとも1種の化合物(iii)と少なくとも1種の化合物(ii)との反応を含んでいてもよく、この場合、第2ステップは、少なくとも1種の化合物(i)とのさらなる反応を含む。これらの変形形態の各々において、少なくとも1個の活性エネルギー線硬化性基は、通常、(メタ)アクリロイル基である。通常、化合物(iii)は、末端封鎖剤である。任意選択で、少なくとも1種の化合物(iv)が、少なくとも1種の化合物(i)との混合物として使用され得る。
−(CF2CF2O)p− 式(3)
−(CF2CF(CF3)O)q− 式(4)
−(CF2CF2CF2O)r− 式(5)
−(CF2O)s− 式(6)
−(CkF2k+1)− 式(7)
式中、k、p、q、r及びsは、上で定められた通りである。式(3)〜(6)のいずれかによる小部分が好ましい。最も典型的には、これらの化合物(i)は、1〜4の間、より典型的には1〜2の間のヒドロキシル官能基を有する。ジオールが好ましい。
CH2=CH(R)−C(=O)−O−(CnH2n−O)r−(C(=O)−C5H10O)t−H
によって表される化合物(iii)であり、式中、R=−H又は−CH3であり、nは、1〜4の整数であり、rは、1〜4の整数であり、tは、1〜20、好ましくは1〜10、より典型的には1〜5の整数である。それらの例は、Tone M100(Dow Chemical)、及び/又は、Bisomer PEMCURE 12A(Cognis)である。
GPCによる分子量の決定:試料の僅かな部分を、テトラヒドロフラン(THF)に溶かし、4本のPLGel Mixed−A ポリスチレンジビニルベンゼンGPCカラム(300mm×7.5mm×20μm)を装備した、液体クロマトグラフ(Merck−Hitachi L7100)に注入する。通常、ポリスチレン標準(通常、分子量範囲は、200〜7,500,000ダルトン)を、内部標準として添加する。試料の成分は、それらの分子の溶液中の大きさに基づいて、GPCカラムによって分離し、屈折率検出器によって検出する。データは、通常、Polymer Laboratories Cirrus GPCソフトウェアによって集め、処理する。
○:指紋が完全に除去される。
×:指紋は除去されない。
842.3gのFluorolink D10H、0.45gのトリスフェニルホスファイト(TPP)、0.453gのブチル化ヒドロキシトルエン(BHT)、266.3gのイソホロンジイソシアナート、及び0.39gのジブチルスズジラウレート(DBTL)を、撹拌機、液体添加漏斗及び温度計を装備した反応フラスコに入れた。反応混合物を、NCO含有量が約4.85%になるまで、90℃に加熱し、撹拌した。添加漏斗に、405.7gのTone M100及び0.45gのDBTLの混合物を入れ、これを2時間で添加した。残留NCO含量が0.2%未満になるまで、反応混合物を80℃に維持した。4252gのPETIAの追加の後、4677mPa.sの粘度(Hoppler、ISO12058、25℃)を有する組成物の生成物を得た。
488gのFluorolink D10H、162gのε(イプシロン)−カプロラクトン、0.65gのジブチルスズジラウレート(DBTL)を、撹拌機、液体添加漏斗及び温度計を装備した反応フラスコに入れた。反応混合物を、ε(イプシロン)−カプロラクトンが1%未満になるまで、120℃に加熱し、撹拌した。反応生成物を、30℃まで冷却し、154.3gのイソホロンジイソシアナートを加えた。反応混合物を、NCO含有量が約4.0%になるまで、90℃に加熱し、撹拌した。添加漏斗に、81gのヒドロキシエチルアクリラート及び0.27gのDBTLの混合物を入れ、これを2時間で加えた。反応混合物を、残留NCO含有量が0.2%未満になるまで、80℃に保った。2656gのPETIAを追加後、8075mPa.sの粘度(Hoppler、ISO12058、25℃)を有する組成物の生成物を得た。
606.3gのFluorolink E10H、0.38gのトリスフェニルホスファイト(TPP)、0.11gのブチル化ヒドロキシトルエン(BHT)、179.3gのイソホロンジイソシアナート、及び0.3gのジブチルスズジラウレート(DBTL)を、撹拌機、液体添加漏斗及び温度計を装備した反応フラスコに入れた。反応混合物を、NCO含有量が約4.81%になるまで、90℃に加熱し、撹拌した。添加漏斗に、94gの2−ヒドロキシルエチルアクリラート、及び0.3gのDBTLの混合物を入れ、これを、2時間で添加した。反応混合物を、残留NCO含有量が0.1%未満になるまで、75℃に保った。2639gのPETIAの添加後に、2465mPa.sの粘度(Hoppler、ISO12058、25℃)を有する白濁した生成物を得た。
例1〜3及び比較例1R〜7R
合成例1及び2R−3Rに従って調製されたオリゴマーを、ベースコーティングの配合において、3つの異なる濃度で試験した。配合物は、これらの例の生成物を、ウレタンアクリラート:EBECRYL(登録商標)1290(Cytecから入手可能)、アクリル化モノマー:EBECRYL(登録商標)145(Cytecから入手可能)、EBECRYL(登録商標)160(Cytecから入手可能)、及びペンタエリトリトールトリ/テトラアクリラート(PETIA)(Cytecから入手可能);並びに開始剤のAdditol CPK(Cytecから入手可能)と混合することによって製造した。試験したベース配合物の組成についての情報及びそれらの特性は、下で表1に記載されている。標準的なハードコート配合物である例1Rとの比較も行った。
UV配合物を、10μmバーコーターによって、厚さ0.2mmのポリカーボナート樹脂製透明シート上に塗布し、120W/cmの無焦点中圧水銀蒸気ランプ(non focalized medium pressure mercury vapor lamp)からのUV放射に、10m/minで2回曝した。
本発明に包含され得る諸態様は、以下のとおり要約される。
[態様1]
−少なくとも1個の活性エネルギー線硬化性基、
−少なくとも1個の小部分:
−(C(=O)C u H 2u O) t − 式(1)
(式中、uは2〜5の整数であり、tは、1〜20の整数である)
を含む少なくとも1個の部分(a1)、
−少なくとも1個のフッ素含有部分(a3)、及び
−部分(a1)と(a3)の間に存在する、少なくとも1個のさらなる部分(a2)
を含み、
部分(a1)と(a3)の間に少なくとも1個のウレタン結合が存在するような仕方で、部分(a1)、(a2)及び(a3)が互いに連結されている、
活性エネルギー線硬化性化合物(A)。
[態様2]
部分(a2)が、ウレタン結合により部分(a1)及び(a3)に接続するポリイソシアナート部分である、上記態様1に記載の化合物。
[態様3]
部分(a3)が、フッ素化アルコールに由来する部分であり、フッ素化アルコールが、好ましくは、フッ素化オキセタンアルコール、ヒドロキシル官能性フルオロエチレン−アルキルビニルエーテル、フルオロアルキルアルコール及び/又はフッ素化(ポリ)エーテルアルコールから選択される、上記態様1又は2に記載の化合物。
[態様4]
部分(a3)が、式(3)〜(7):
−(CF 2 CF 2 O) p − 式(3)
−(CF 2 CF(CF 3 )O) q − 式(4)
−(CF 2 CF 2 CF 2 O) r − 式(5)
−(CF 2 O) s − 式(6)
−(C k F 2k+1 )− 式(7)
(式中、kは、1〜16の整数であり、p、q、r及びsの各々は、1〜100の整数である)の1つ又は複数によって表される少なくとも1個の小部分を含む、上記態様1から3までのいずれか一項に記載の化合物。
[態様5]
活性エネルギー線硬化性官能基が、(メタ)アクリロイル基、ビニル基、アリル基、チオール基及び/又はエポキシ基から選択される、上記態様1から4までのいずれか一項に記載の化合物。
[態様6]
−少なくとも1種のフッ素化アルコール(i)、
−少なくとも1種のポリイソシアナート(ii)、及び
−少なくとも1個の活性エネルギー線硬化性基と、イソシアナート基と反応できる本質的に1個の反応性基とを含有する、少なくとも1種の(ポリ)ラクトン−修飾化合物(iii)、
の反応により得られる、上記態様1から5までのいずれか一項に記載の化合物。
[態様7]
化合物(iii)が、式(2):
CH 2 =CH(R)−C(=O)−O−(C n H 2n −O) r −(C(=O)−C 5 H 10 O) t −H
(式中、Rは、−H又は−CH 3 、nは1〜4の整数であり、rは1〜4の整数であり、tは1〜10の整数である)
によって表される、上記態様6に記載の化合物。
[態様8]
組成物の不揮発性部分の全重量に対して、上記態様1から7までのいずれか一項に記載の少なくとも1種の化合物(A)を0.5〜100重量%、及び少なくとも1種の活性エネルギー線硬化性化合物(B)を0〜99.5重量%含む活性エネルギー線硬化性組成物。
[態様9]
3〜100重量%の化合物(A)及び0〜97重量%の化合物(B)を含む、上記態様8に記載の組成物。
[態様10]
10〜100重量%の化合物(A)、及び0〜90重量%の化合物(B)を含む、上記態様8又は9に記載の組成物。
[態様11]
化合物(B)が、(ポリ)ウレタン(メタ)アクリラート、(ポリ)エステル(メタ)アクリラート、(ポリ)エーテル(メタ)アクリラート、エポキシ(メタ)アクリラート及び/又は(メタ)アクリル(メタ)アクリラートから選択される、上記態様8から10までのいずれか一項に記載の組成物。
[態様12]
シリコーン化合物、及び/又は、(A)とは異なるフッ素化化合物から選択される少なくとも1種の化合物(C)をさらに含む、上記態様8から11までのいずれか一項に記載の組成物。
[態様13]
物品又は基材の少なくとも1つの表面に、上記態様9から12までのいずれか一項に記載の組成物を塗布するステップ、その後の硬化するステップを含む、物品又は基材のコーティング方法。
[態様14]
前記コーティングの硬化後のヘーズが、最大でも1.0%であり、前記コーティングの硬化後の厚さが、5〜25μmの範囲にある、上記態様13に記載の方法。
[態様15]
組成物が、コーティング表面にミクロ−ナノ構造を付与する塗布技術により塗布される、上記態様13又は14に記載の方法。
[態様16]
−コーティング表面に置かれた水に対する、少なくとも95°、好ましくは少なくとも100°の接触角、
−コーティング表面に置かれたn−ヘキサデカンに対する、少なくとも60°、より好ましくは少なくとも62°、最も好ましくは少なくとも65°の接触角
の1つ又は複数によって特徴付けられる、上記態様13から15までのいずれか一項に記載の方法に従ってコーティングされた物品。
Claims (13)
- −(メタ)アクリロイル基、ビニル基及び/又はアリル基から選択される、少なくとも1個の活性エネルギー線硬化性基、
−少なくとも1個の小部分:
−(C(=O)CuH2uO)t− 式(1)
(式中、uは2〜5の整数であり、tは、1〜20の整数である)
を含む少なくとも1個の部分(a1)、
−少なくとも1個のフッ素含有部分(a3)、及び
−部分(a1)と(a3)の間に存在する、少なくとも1個のさらなる部分(a2)
を含み、
部分(a1)と(a3)の間に少なくとも1個のウレタン結合が存在するような仕方で、部分(a1)、(a2)及び(a3)が互いに連結されており、
部分(a2)が、ウレタン結合により部分(a1)及び(a3)に接続するポリイソシアナート部分であり、
部分(a3)が、式(3)〜(6):
−(CF 2 CF 2 O) p − 式(3)
−(CF 2 CF(CF 3 )O) q − 式(4)
−(CF 2 CF 2 CF 2 O) r − 式(5)
−(CF 2 O) s − 式(6)
(式中、p、q、r及びsの各々は、1〜100の整数である)の1つ又は複数によって表される少なくとも1個の小部分を含む、フッ素化ジオールに由来する部分である、
活性エネルギー線硬化性化合物(A)。 - フッ素化ジオールが、フッ素化オキセタンアルコール、ヒドロキシル官能性フルオロエチレン−アルキルビニルエーテル、フルオロアルキルアルコール及び/又はフッ素化(ポリ)エーテルアルコールから選択されるジオールである、請求項1に記載の化合物。
- −前記にて特定されたとおりの少なくとも1種のフッ素化ジオール(i)、
−少なくとも1種のポリイソシアナート(ii)、及び
−少なくとも1個の活性エネルギー線硬化性基と、イソシアナート基と反応できる本質的に1個の反応性基とを含有する、少なくとも1種の(ポリ)ラクトン−修飾化合物(iii)、
の反応により得られる、請求項1又は2に記載の化合物。 - 化合物(iii)が、式(2):
CH2=C(R)−C(=O)−O−(CnH2n−O)r−(C(=O)−C5H10O)t−H
(式中、Rは、−H又は−CH3、nは1〜4の整数であり、rは1〜4の整数であり、tは1〜10の整数である)
によって表される、請求項3に記載の化合物。 - 組成物の不揮発性部分の全重量に対して、請求項1から4までのいずれか一項に記載の少なくとも1種の化合物(A)を0.5〜100重量%、及び少なくとも1種の活性エネルギー線硬化性化合物(B)を0〜99.5重量%含む活性エネルギー線硬化性組成物。
- 3〜100重量%の化合物(A)及び0〜97重量%の化合物(B)を含む、請求項5に記載の組成物。
- 10〜100重量%の化合物(A)、及び0〜90重量%の化合物(B)を含む、請求項5又は6に記載の組成物。
- 化合物(B)が、(ポリ)ウレタン(メタ)アクリラート、(ポリ)エステル(メタ)アクリラート、(ポリ)エーテル(メタ)アクリラート、エポキシ(メタ)アクリラート及び/又は(メタ)アクリル(メタ)アクリラートから選択される、請求項5から7までのいずれか一項に記載の組成物。
- シリコーン化合物、及び/又は、(A)とは異なるフッ素化化合物から選択される少なくとも1種の化合物(C)をさらに含む、請求項5から8までのいずれか一項に記載の組成物。
- 物品又は基材の少なくとも1つの表面に、請求項6から9までのいずれか一項に記載の組成物を塗布するステップ、その後の硬化するステップを含む、物品又は基材のコーティング方法。
- コーティングの硬化後のヘーズが、最大でも1.0%であり、前記コーティングの硬化後の厚さが、5〜25μmの範囲にある、請求項10に記載の方法。
- 組成物が、コーティング表面にミクロ−ナノ構造を付与する塗布技術により塗布される、請求項10又は11に記載の方法。
- 請求項5から9までのいずれか一項に記載の組成物の硬化物であるコーティング及び物品を含む、コーティングされた物品であって、
−コーティング表面に置かれた水に対する、少なくとも95°の接触角、
−コーティング表面に置かれたn−ヘキサデカンに対する、少なくとも60°の接触角
の1つ又は複数によって特徴付けられる、コーティングされた物品。
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EP2583986A1 (en) * | 2011-10-17 | 2013-04-24 | Cytec Surface Specialties, S.A. | Fluorinated water-oil repellency agents |
TW201817825A (zh) * | 2016-09-21 | 2018-05-16 | 日商日產化學工業股份有限公司 | 耐劃傷性硬塗材料 |
JP6874828B2 (ja) * | 2017-03-31 | 2021-05-19 | ダイキン工業株式会社 | 硬化性組成物、その製造方法、及びそれを用いた物品 |
JP7041405B2 (ja) * | 2017-09-01 | 2022-03-24 | 日産化学株式会社 | 延伸性耐擦傷性コーティング用硬化性組成物 |
KR102013860B1 (ko) | 2017-11-24 | 2019-08-23 | 한국생산기술연구원 | 불소그룹이 도입된 불소 폴리실라잔 소재 및 이의 제조방법 |
CN113423513B (zh) * | 2019-02-06 | 2023-08-15 | 日产化学株式会社 | 耐光性硬涂用固化性组合物 |
Family Cites Families (19)
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JP2631501B2 (ja) * | 1988-03-23 | 1997-07-16 | 日本化薬株式会社 | 樹脂組成物及び光ファイバのクラッド材 |
JPH01308420A (ja) * | 1988-06-07 | 1989-12-13 | Nippon Kayaku Co Ltd | ウレタン(メタ)アクリレート混合物、これを用いた樹脂組成物及び光ファイバ用コーティング剤 |
JP2657415B2 (ja) * | 1989-03-30 | 1997-09-24 | 日本化薬株式会社 | 樹脂組成物及び光ファイバー用コーティング剤 |
US6673889B1 (en) | 1999-06-28 | 2004-01-06 | Omnova Solutions Inc. | Radiation curable coating containing polyfuorooxetane |
KR100487025B1 (ko) * | 2002-02-28 | 2005-05-11 | 주식회사 루밴틱스 | 광도파로용 광경화성 수지 조성물 및 이로부터 제조된광도파로 |
WO2004024822A1 (en) | 2002-09-11 | 2004-03-25 | Henkel Loctite Corporation | High-gloss room temperature curable water-based mold release agent |
JP2004176054A (ja) * | 2002-11-13 | 2004-06-24 | Asahi Glass Co Ltd | 活性エネルギー線硬化型被覆用組成物及びプラスチック成形品 |
KR101014582B1 (ko) | 2002-11-13 | 2011-02-16 | 아사히 가라스 가부시키가이샤 | 활성 에너지선 경화형 피복용 조성물 및 그 조성물의경화물로 이루어지는 피막을 갖는 성형품 |
JP4779293B2 (ja) | 2003-10-21 | 2011-09-28 | Tdk株式会社 | ハードコート剤組成物及びこれを用いた光情報媒体 |
EP1923041A1 (de) | 2006-10-20 | 2008-05-21 | Symrise GmbH & Co. KG | Verwendung von C10-C14-Alkandiolen zur Herstellung eines Mittels zur Prophylaxe und/oder Behandlung von Malassezia-induzierter Schuppenbildung, sowie Zubereitungen enthaltend C10-C14-Alkandiole |
US20080124555A1 (en) * | 2006-11-29 | 2008-05-29 | 3M Innovative Properties Company | Polymerizable composition comprising perfluoropolyether urethane having ethylene oxide repeat units |
DE102007007914A1 (de) * | 2007-02-14 | 2008-08-21 | Giesecke & Devrient Gmbh | Prägelack für mikrooptische Sicherheitselemente |
EP1962110A1 (en) * | 2007-02-14 | 2008-08-27 | Sony Corporation | Anti-glare film, method for manufacturing the same, and display device using the same |
CN101903483B (zh) | 2007-12-18 | 2014-09-10 | 陶氏环球技术公司 | 对玻璃粘合剂具有增强的粘合性的窗玻璃用保护涂层 |
EP2105453A1 (en) * | 2008-03-25 | 2009-09-30 | Siegwerk Benelux SA | Acid modified polyurethane acrylate |
JP5914907B2 (ja) | 2008-08-11 | 2016-05-11 | 株式会社オートネットワーク技術研究所 | 防錆剤および表面処理金属材 |
US8299170B2 (en) | 2008-10-08 | 2012-10-30 | Toyota Motor Engineering & Manufacturing North America, Inc. | Self-stratifying coating |
JPWO2011001846A1 (ja) * | 2009-06-30 | 2012-12-13 | 旭硝子株式会社 | 表面処理剤、物品および含フッ素エーテル化合物 |
CA2770212C (en) | 2009-08-28 | 2017-03-28 | Hercules Incorporated | Film coating composition from solid powder compounds |
-
2012
- 2012-02-27 EP EP12157162.4A patent/EP2631254A1/en not_active Withdrawn
- 2012-10-04 KR KR1020147010171A patent/KR20140082706A/ko not_active Application Discontinuation
- 2012-10-04 CN CN201280050946.8A patent/CN103906780B/zh active Active
- 2012-10-04 JP JP2014536175A patent/JP6448367B2/ja active Active
- 2012-10-04 WO PCT/EP2012/069648 patent/WO2013056982A1/en active Application Filing
- 2012-10-04 EP EP12767016.4A patent/EP2768879A1/en not_active Withdrawn
- 2012-10-04 US US14/350,651 patent/US20140256854A1/en not_active Abandoned
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2017
- 2017-05-24 JP JP2017102648A patent/JP2017149985A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
EP2631254A1 (en) | 2013-08-28 |
JP2017149985A (ja) | 2017-08-31 |
WO2013056982A1 (en) | 2013-04-25 |
CN103906780A (zh) | 2014-07-02 |
EP2768879A1 (en) | 2014-08-27 |
US20140256854A1 (en) | 2014-09-11 |
KR20140082706A (ko) | 2014-07-02 |
JP2015502985A (ja) | 2015-01-29 |
CN103906780B (zh) | 2015-12-09 |
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