JP2009102463A - 撥水撥油剤 - Google Patents
撥水撥油剤 Download PDFInfo
- Publication number
- JP2009102463A JP2009102463A JP2007273280A JP2007273280A JP2009102463A JP 2009102463 A JP2009102463 A JP 2009102463A JP 2007273280 A JP2007273280 A JP 2007273280A JP 2007273280 A JP2007273280 A JP 2007273280A JP 2009102463 A JP2009102463 A JP 2009102463A
- Authority
- JP
- Japan
- Prior art keywords
- water
- oil
- weight
- meth
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000005871 repellent Substances 0.000 title claims abstract description 56
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 76
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 229920001577 copolymer Polymers 0.000 claims abstract description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 26
- 239000012948 isocyanate Substances 0.000 claims abstract description 23
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 22
- 239000011737 fluorine Substances 0.000 claims abstract description 21
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000006185 dispersion Substances 0.000 claims abstract description 20
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 230000002940 repellent Effects 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 10
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical group O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 abstract description 18
- 239000000835 fiber Substances 0.000 abstract description 12
- 229920002994 synthetic fiber Polymers 0.000 abstract description 4
- 239000012209 synthetic fiber Substances 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 3
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 50
- -1 carbon atoms Hydroxyalkyl vinyl ethers Chemical class 0.000 description 25
- 239000004744 fabric Substances 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 238000007334 copolymerization reaction Methods 0.000 description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 9
- 238000004945 emulsification Methods 0.000 description 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 8
- 239000003093 cationic surfactant Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical class O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 231100000693 bioaccumulation Toxicity 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 239000004811 fluoropolymer Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CDXFIRXEAJABAZ-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDXFIRXEAJABAZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229940051250 hexylene glycol Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 2
- CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical compound NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-UHFFFAOYSA-N 0.000 description 2
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- NTNWOCRCBQPEKQ-UHFFFAOYSA-N NG-mono-methyl-L-arginine Natural products CN=C(N)NCCCC(N)C(O)=O NTNWOCRCBQPEKQ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000004148 curcumin Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- VPKQPPJQTZJZDB-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C VPKQPPJQTZJZDB-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- KEZMBAQUUXDDDQ-UHFFFAOYSA-N CCC.N=C=O.N=C=O Chemical compound CCC.N=C=O.N=C=O KEZMBAQUUXDDDQ-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
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- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- QBDADGJLZNIRFQ-UHFFFAOYSA-N ethenyl octanoate Chemical compound CCCCCCCC(=O)OC=C QBDADGJLZNIRFQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WHIVNJATOVLWBW-SNAWJCMRSA-N methylethyl ketone oxime Chemical compound CC\C(C)=N\O WHIVNJATOVLWBW-SNAWJCMRSA-N 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- BNMCQIRVFUGISV-UHFFFAOYSA-N propan-2-one;prop-2-enamide Chemical compound CC(C)=O.NC(=O)C=C BNMCQIRVFUGISV-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
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Abstract
【解決手段】(a)一般式 CnF2n+1CmH2mOCOCR=CH2(ここで、Rは水素原子またはメチル基であり、nは4、5または6であり、mは1、2、3または4である)で表わされるパーフルオロアルキルアルキル(メタ)アクリレート、(b)ベンジル(メタ)アクリレート、(c)ベンジル(メタ)アクリレート以外の非フッ素系重合性単量体および(d)架橋性基含有重合性単量体を共重合単位として含有する含フッ素共重合体の水性分散液に、該水性分散液中の固形分重量に対して重量比で0.05〜3.0となる量のブロックドイソシアネートが添加された撥水撥油剤。
【選択図】 なし
Description
接着 第50巻 第5号 第16〜22頁 (2006)
Rf-Y-O-CO-CX=CH2
X:F,Cl,Br,I,CFX1X2,CN,炭素数1〜20のフルオロアルキル基、ベンジル 基、フェニル基
Y:炭素数1〜10の脂肪族基,炭素数6〜10の芳香族基または環状脂肪族基、
CH2CH2NR1SO2基,CH2CH(OY1)CH2基
Rf:炭素数1〜6のフルオロアルキル基
で表わされる含フッ素単量体化合物であって、X=Hであるアクリル酸誘導体は比較製造例とされ、X=CH3であるメタクリル酸誘導体も意識的に除外されている。
CnF2n+1CmH2mOCOCR=CH2
(ここで、Rは水素原子またはメチル基であり、nは4、5または6であり、mは1、2、3または4である)で表わされるパーフルオロアルキルアルキル(メタ)アクリレート、(b)ベンジル(メタ)アクリレート、(c)ベンジル(メタ)アクリレート以外の非フッ素系重合性単量体および(d)架橋性基含有重合性単量体を共重合単位として含有する含フッ素共重合体の水性分散液に、該水性分散液中の固形分重量に対して重量比で0.05〜3.0となる量のブロックドイソシアネートが添加された撥水撥油剤によって達成される。
CnF2n+1CmH2mOCOCR=CH2
R:水素原子,メチル基
n:4、5または6
m:1、2、3または4
で表わされるパーフルオロアルキルアルキル(メタ)アクリレートとしては、好ましくは次のような化合物が挙げられる。
C4F9CH2CH2OCOCH=CH2
C4F9CH2CH2OCOC(CH3)=CH2
C6F13CH2CH2OCOCH=CH2
C6F13CH2CH2OCOC(CH3)=CH2
CH2=C(CH3)CON--N+(CH3)2CH2CH(OH)CH3
CH2=C(CH3)CON--N+(CH3)3
で表わされる化合物等のアミド基含有単量体、アジリジニルエチル(メタ)アクリレート等のアジリジニル基含有単量体、エチレングリコールジ(メタ)アクリレート、ポリオキシエチレンジ(メタ)アクリレート、ポリオキシプロピルグリコールジ(メタ)アクリレート等のポリオールポリ(メタ)アクリレート等が挙げられ、好ましくは親水性単量体が用いられる。
H(OCH2CH2)xNRCH2CH2CH2N〔(CH2CH2O)yH〕(CH2CH2O)zH
で表わされるポリオキシエチレンアルキルジアミン(ライオン製品エソデュオミンT/25等)、ポリオキシエチレンドデシルアミン(日本油脂製品ナイミーンL-207等)を酢酸等の有機酸で中和処理したものを用いることもできる。
2-(n-パーフルオロヘキシル)エチルメタクリレート 58.3g (45.6%)
ベンジルメタクリレート 29.2g (22.8%)
2-ヒドロキシエチルメタクリレート 5.6g ( 4.4%)
ポリエチレングリコール(n=4)モノメタクリレート 11.7g ( 9.1%)
(日本油脂製品PE-200)
ラウリルメルカプタン 0.5g
ポリオキシエチレン多環フェニルエーテル 7.0g
(日本乳化剤製品ニューコール-740)
ヘキシレングリコール 35.0g
イオン交換水 267.1g
塩化ビニリデン 17.5g (13.7%)
N-メチロールアクリルイミド(イオン交換水29.3gに溶解) 5.6g ( 4.4%)
2,2′-アゾビス(2-アミジノプロパン)・2塩酸塩 2.8g
(イオン交換水30.4gに溶解)
を投入し(イオン交換水全体量326.8gを含む合計量500.0g)、さらに内温を徐々に70℃迄上げ、その温度で4時間反応させた。反応終了後冷却し、固形分濃度25.0重量%の水性分散液Aを得た。なお、水性分散液から分離して得られた共重合体の融点(DSC法)は45℃であった。
参考例1において、共単量体(a)〜(d)の種類および使用量、ならびにイオン交換水全体量が次の表1に示されるように変更され、固形分濃度25.0重量%(ただし、参考例2は25.3重量%)の水性分散液B〜Dを得た。なお、表1中には、水性分散液から分離して得られた共重合体の融点(DSC法)も併記されている。
表1
参考例2 参考例3 参考例4
共単量体 g % g % g %
(a)成分
FAMAC-6 78.5 61.5 100.6 79.1 62.8 49.2
FAAC-6 15.7 12.3
(b)成分
BzMA 22.4 17.6 7.4 5.8 22.4 17.6
(c)成分
PEGM 4.2 3.3 4.2 3.3 4.2 3.3
VDC 11.2 8.8 3.8 3.0 11.2 8.8
(d)成分
HEA 5.6 4.4 5.6 4.4 5.6 4.4
NMAM 5.6 4.4 5.6 4.4
NMMA 5.6 4.4
水全体量 (g) 323.5 327.5 327.2
水性分散液 B C D
共重合体融点(℃) 44 46 44
注) FAMAC-6:2-(パーフルオロヘキシル)エチルメタクリレート
FAAC-6:2-(パーフルオロヘキシル)エチルアクリレート
BzMA:ベンジルメタクリレート
PEGM:ポリエチレングリコール(n=4)モノメタクリレート(PE-200)
VDC:塩化ビニリデン
HEA:2-ヒドロキシエチルアクリレート
NMAM:N-メチロールアクリルアミド
NMMA:N-メチロールメタクリルアミド
参考例1で得られた水性分散液A 2.0重量部(固形分として0.5重量部に相当)に、ブロックドイソシアネートとして2-ブタノン-o,o′〔メチレンビス(4,1-フェニレンアミノカルボキシ)〕ジオキシム〔MDI-BTO〕の水性エマルジョン0.375重量部(固形分として0.15重量部に相当)を加えた後、イオン交換水97.625重量部で希釈して、撥水撥油剤Aを得た。
実施例1において、それぞれ参考例2〜4で得られた水性分散液B〜Dの同量を用い、撥水撥油剤B〜Dを得た。
実施例1において、ブロックドイソシアネートとしてのMDI-BTO水性エマルジョンの使用量が1.25重量部に、またイオン交換水量が96.75重量部にそれぞれ変更され、撥水撥油剤Eを得た。
実施例1において、ブロックドイソシアネートとしてのMDI-BTO水性エマルジョンの使用量が0.125重量部に、またイオン交換水量が97.875重量部にそれぞれ変更され、撥水撥油剤Fを得た。
参考例1で得られた水性分散液A 2.0重量部をイオン交換水98.0重量部で希釈して、撥水撥油剤Gを得た。
比較例1において、それぞれ参考例2〜4で得られた水性分散液B〜Dの同量を用い、撥水撥油剤H〜Jを得た。
撥水度 状態
100 表面に湿潤や水滴の付着のないもの
90 表面にわずかに水滴付着を示すもの
80 表面に個々の部分的湿潤を示すもの
70 表面の半分に湿潤を示すもの
50 表面全体に湿潤を示すもの
0 表裏両面が完全に湿潤を示すもの
表面張力
撥油性No. 試験溶液 (mN/m,25℃)
8 n-ヘプタン 20.0
7 n-オクタン 21.8
6 n-デカン 23.5
5 n-ドデカン 25.0
4 n-テトラデカン 26.7
3 n-ヘキサデカン 27.3
2 ヌジョール-n-ヘキサデカン 29.6
(容積比65%:35%)
1 ヌジョール 31.2
それぞれ撥水撥油剤A〜Jを用いて、綿布、綿-ポリエステル混紡布、ポリエステル布またはナイロン布を前記の如くにして撥水撥油処理した後、JIS L0217別表103の水洗い法に準拠し、洗濯を5回または10回くり返した後、風乾したものについて、撥水性および撥油性の評価を行った。得られた評価結果は、撥水性評価/撥油性評価という形で次の表2に示される。
表2
撥水 撥水性評価/撥油性評価
例 撥油剤 綿布 混紡布 ポリエステル布 ナイロン布
〔洗濯回数:0回〕
実施例1 A 100/1 100/4 100/4 100/5
〃 2 B 100/4 100/5 100/5 100/6
〃 3 C 100/5 100/5 100/6 100/6
〃 4 D 100/5 100/5 100/6 100/6
〃 5 E 100/4 100/5 100/5 100/6
〃 6 F 100/4 100/5 100/5 100/6
比較例1 G 100/1 100/4 100/4 100/5
〃 2 H 100/3 100/5 100/5 100/6
〃 3 I 100/5 100/5 100/6 100/6
〃 4 J 100/5 100/5 100/6 100/6
〔洗濯回数:5回〕
実施例1 A 100/1 100/4 100/4 100/6
〃 2 B 100/4 100/5 100/5 100/6
〃 3 C 100/5 100/5 100/6 100/6
〃 4 D 100/4 100/5 100/6 100/6
〃 5 E 100/4 100/4 100/4 100/6
〃 6 F 100/3 100/5 100/5 100/6
比較例1 G 70/0 80/1 100/4 100/5
〃 2 H 70/2 100/4 100/5 100/6
〃 3 I 70/3 100/4 100/6 100/6
〃 4 J 70/3 100/4 100/6 100/6
〔洗濯回数:10回〕
実施例1 A 70/1 100/3 100/4 100/5
〃 2 B 90/3 100/4 100/5 100/5
〃 3 C 90/3 100/4 100/6 100/6
〃 4 D 90/4 100/5 100/5 100/6
〃 5 E 90/3 100/4 100/5 100/5
〃 6 F 90/3 100/4 100/5 100/5
比較例1 G 50/0 70/0 100/4 100/4
〃 2 H 70/1 80/4 100/5 100/5
〃 3 I 70/1 80/4 100/5 100/5
〃 4 J 70/1 80/4 100/5 100/5
Claims (4)
- (a)一般式
CnF2n+1CmH2mOCOCR=CH2
(ここで、Rは水素原子またはメチル基であり、nは4、5または6であり、mは1、2、3または4である)で表わされるパーフルオロアルキルアルキル(メタ)アクリレート、(b)ベンジル(メタ)アクリレート、(c)ベンジル(メタ)アクリレート以外の非フッ素系重合性単量体および(d)架橋性基含有重合性単量体を共重合単位として含有する含フッ素共重合体の水性分散液に、該水性分散液中の固形分重量に対して重量比で0.05〜3.0となる量のブロックドイソシアネートが添加された撥水撥油剤。 - (c)成分非フッ素系重合性単量体が塩化ビニリデンである含フッ素共重合体が用いられた請求項1記載の撥水撥油剤。。
- (d)成分架橋性基含有重合性単量体が親水性単量体である含フッ素共重合体が用いられた請求項1記載の撥水撥油剤。
- (a)成分が10〜80重量%、(b)成分が5〜80重量%、(c)成分が5〜80重量%、(d)成分が0.5〜40重量%の共重合組成を有する含フッ素共重合体が用いられた請求項1記載の撥水撥油剤。
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KR101649572B1 (ko) | 2011-12-12 | 2016-08-19 | 유니마테크 가부시키가이샤 | 함불소 공중합체 및 그것을 유효 성분으로 하는 발수발유제 |
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KR20140101784A (ko) * | 2011-12-12 | 2014-08-20 | 유니마테크 가부시키가이샤 | 함불소 공중합체 및 그것을 유효 성분으로 하는 발수발유제 |
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CN110761074A (zh) * | 2018-07-26 | 2020-02-07 | 乳源东阳光氟有限公司 | 一种环保低温型拒水拒油组合物 |
CN110761074B (zh) * | 2018-07-26 | 2023-08-08 | 乳源东阳光氟有限公司 | 一种环保低温型拒水拒油组合物 |
WO2021060237A1 (ja) * | 2019-09-26 | 2021-04-01 | 第一工業製薬株式会社 | 樹脂用添加剤 |
JP2021050300A (ja) * | 2019-09-26 | 2021-04-01 | 第一工業製薬株式会社 | 樹脂用添加剤 |
JP2021127548A (ja) * | 2020-02-17 | 2021-09-02 | 明成化学工業株式会社 | 吸水性及び撥水性を併せ持つ繊維製品 |
JP7422972B2 (ja) | 2020-02-17 | 2024-01-29 | 明成化学工業株式会社 | 吸水性及び撥水性を併せ持つ繊維製品 |
WO2021200646A1 (ja) * | 2020-03-31 | 2021-10-07 | 東レ株式会社 | フッ素含有重合体粒子およびそれを含む分散液 |
WO2023286402A1 (ja) * | 2021-07-12 | 2023-01-19 | ユニマテック株式会社 | 含フッ素共重合体およびこれを用いた表面改質基材 |
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WO2009054176A1 (ja) | 2009-04-30 |
CA2702687A1 (en) | 2009-04-30 |
EP2208770B1 (en) | 2012-08-01 |
EP2208770A1 (en) | 2010-07-21 |
KR20100084175A (ko) | 2010-07-23 |
CN101835868A (zh) | 2010-09-15 |
EP2208770A4 (en) | 2011-06-01 |
EP2208770B9 (en) | 2012-10-31 |
CA2702687C (en) | 2014-07-15 |
US8796368B2 (en) | 2014-08-05 |
JP5315663B2 (ja) | 2013-10-16 |
US20100249312A1 (en) | 2010-09-30 |
KR101456864B1 (ko) | 2014-11-03 |
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