JPS636676B2 - - Google Patents
Info
- Publication number
- JPS636676B2 JPS636676B2 JP55067782A JP6778280A JPS636676B2 JP S636676 B2 JPS636676 B2 JP S636676B2 JP 55067782 A JP55067782 A JP 55067782A JP 6778280 A JP6778280 A JP 6778280A JP S636676 B2 JPS636676 B2 JP S636676B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- parts
- fluoroalkyl group
- oil
- containing compound
- 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.)
- Expired
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000005871 repellent Substances 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 239000004753 textile Substances 0.000 claims description 11
- 230000002940 repellent Effects 0.000 claims description 7
- 238000003672 processing method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 description 12
- 238000005108 dry cleaning Methods 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000012545 processing Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- UUPXKAJPMYOPLF-UHFFFAOYSA-N dimethyl(octadecyl)azanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN(C)C UUPXKAJPMYOPLF-UHFFFAOYSA-N 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- -1 ethylene, propylene, butylene, butadiene Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 150000004812 organic fluorine compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 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
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 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
- YACLCMMBHTUQON-UHFFFAOYSA-N 1-chloro-1-fluoroethane Chemical compound CC(F)Cl YACLCMMBHTUQON-UHFFFAOYSA-N 0.000 description 1
- TXTIIWDWHSZBRK-UHFFFAOYSA-N 2,4-diisocyanato-1-methylbenzene;2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)CO.CC1=CC=C(N=C=O)C=C1N=C=O TXTIIWDWHSZBRK-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 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
- 229920002978 Vinylon Polymers 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WPEOOEIAIFABQP-UHFFFAOYSA-N hexanedioic acid;hexane-1,6-diol Chemical compound OCCCCCCO.OC(=O)CCCCC(O)=O WPEOOEIAIFABQP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000002649 leather substitute Substances 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003607 modifier 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
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
本発明は撥水撥油加工法、とりわけドライクリ
ーニング後および洗濯後の撥水撥油性能の低下を
改善した繊維製品への撥水撥油加工法に関するも
のである。
現在、撥水撥油加工は、独得の低表面エネルギ
ーを有するフルオロアルキル基含有化合物を繊維
製品に付着せしめて水性汚れのみならず油性汚れ
をも反撥させようとする加工法が主流を占めるに
到つている。
このような加工法は、撥水撥油剤となり得るフ
ルオロアルキル基含有化合物の有機溶剤溶液によ
り、あるいは水分散液によりなされることが多い
が、本化合物が処理された繊維製品から洗い落と
されたり、溶かし出された場合には、撥水撥油性
は保持されない。特に繊維製品をドライクリーニ
ングする場合、ドライクリーニング溶剤が最近ケ
ロシンから溶解力の強いパークロルエチレン、さ
らにフレオン(クロロフルオロエタン類)へと改
良されるに到り、洗い落とすべき汚れと同時に撥
水撥油剤も溶かし出されるので、ドライクリーニ
ング後はもはや撥水撥油性がほとんどなく、汚れ
反撥性がなくなるという欠点があつた。
本発明者はこの欠点を改良すべく鋭意研究した
結果、撥水撥油剤となりうるフルオロアルキル基
含有化合物に多官能イソシアネートを配合し処理
した繊維製品が、本欠点を大幅に改良し同時に本
化合物による処理の諸特徴を何ら損なわないこと
を見出し、本発明を完成した。
即ち、本発明は撥水撥油性を有するフルオロア
ルキル基含有化合物で繊維製品の撥水撥油加工を
行なうに際し、前記フルオロアルキル基含有化合
物100重量部(以下、単に部という)に対し多官
能イソシアネートを5〜300部配合することを特
徴とする繊維製品の撥水撥油加工法に関する。
本発明で使用される撥水撥油性能を有するフル
オロアルキル基含有化合物とは、3〜20個好まし
くは6〜12個の炭素原子を有するフルオロアルキ
ル基を有し、水不溶性(25℃で1重量%以下)で
主要転移温度即ち融点、ガラス転移点あるいは軟
化点が20℃以上で分子量が約700〜約200000の非
粘着性化合物である。
このような有機フツ素化合物の例を挙げれば次
のとおりである。
(1) 炭素数3〜20のフルオロアルキル基を有する
ビニル単量体の単独重合体またはフツ素を含ま
ないビニル単量体との共重合体。
フルオロアルキル基を有するビニル単量体の
例としては次のものが挙げられる。
C7F15CH2OCOCH=CH2
C8F17SO2N(C3H7)CH2CH2OCOCH=CH2
C8F17SO2N(CH3)CH2CH2OCOC(CH3)=CH2
C7F15CON(C2H5)CH2CH2OCOC(CH3)=CH2
CF3(CF2)5CH2CH2OCOCH=CH2
CF3(CF2)9CH2CH2OCH=CH2
C8F17(CH2)11OCOC(CH3)=CH2
(CF3)2CFO(CH2)5OCOCH=CH2
C8F17SO2N(CH2CH2OCOCH=CH2)2
C8F17SO2N(CH3)(CH2)10COOCH2CH=CH2
C8F17SO2N(C2H5)CH2CH2OCOCH=CHCOOC4H9
C6F13SO2N(CH3)CH2CH2OCOCH=CH2
C8F17SO2NHCH2CH2SO2CH=CH2
フツ素を含まないビニル単量体の例として
は、エチレン、プロピレン、ブチレン、ブタジ
エン、イソプレン、クロロプレン、塩化ビニ
ル、塩化ビニリデン、スチレン、(メタ)アク
リル酸のアルコールまたはアルキルアミン(い
ずれも炭素数20以下)とのエステルまたはアミ
ド、ジアセトンアクリルアミド、N―メチロー
ルアクリルアミド、アクリロニトリル、アクリ
ルアミド、ビニルアセテート、シロキサン結合
を有するビニル化合物などがあげられる。いず
れの単量体も混合して使用することもできる。
これらの単独重合体あるいは共重合体はビニ
ル重合の公知の方法によつて行なうことができ
るが、例えばラジカル開始剤を使用した溶液重
合、エマルジヨン重合が一般的である。重合体
の分子量は開始剤濃度、連鎖移動剤の種類と濃
度によつて好ましい範囲に調整できるが、一般
に3000以上が好ましい。
(2) 炭素数3〜20のフルオロアルキル基含有の一
価もしくは多価アルコールとフツ素化されてい
てもよい一価もしくは多価カルボン酸との(ポ
リ)エステル。フツ素化されていてもよい一価
もしくは多価アルコールと炭素数3〜20のフル
オロアルキル基を有する一価もしくは多価カル
ボン酸との(ポリ)エステル。
この場合使用される成分の例を次に挙げる。
C9F19CH2CH2OH
C8F17SO2N(C3H7)CH2CH2OH
C8F17SO2N(CH2CH2OH)2
C8F17SO2N(C2H5)CH2CH(OH)CH2OH
C7F15COOH
C8F17SO2N(C3H7)CH2COOH
安息香酸、アジピン酸、セバシン酸、フタル
酸、マレイン酸、トリメリツト酸エチレングリ
コールモノメチルエーテル、エチレングリコー
ル、プロピレングリコール、ジエチレングリコ
ール、グリセリン、ポリプロピレングリコー
ル、2―エチルヘキサノール、ステアリルアル
コール、該(ポリ)エステルは分子量が1000以
上が好ましい。
(3) 炭素数3〜20のフルオロアルキル基を有する
一価または多価アルコール(場合によつてはフ
ツ素を含まない一価または多価アルコールを混
ぜても良い)と一価または多価イソシアネー
ト、例えばフエニルイソシアネート、トリレン
ジイソシアネート、ジフエニルメタンジイソシ
アネート、ヘキサメチレンジイソシアネート、
ポリメチレンポリフエニルイソシアネートとの
(ポリ)ウレタン。
該(ポリ)ウレタンは分子量が700以上のも
のが好ましい。
(4) 炭素数3〜20のフルオロアルキル基を有する
エポキシ化合物、例えば
の単独重合体および好ましくはプロピレンオキ
サイド、エピクロルヒドリンなどのフツ素不含
エポキシ化合物との共重合体。
このような重合体の分子量は3000以上が好ま
しい。
しかして本発明で使用されるフルオロアルキル
基含有化合物は、濃度0.5重量%の希釈液(溶液
または分散液)を作り、これにポリエステル100
加工糸織物を浸し、ウエツトピツクアツプ100%
(織物と等重量の希釈液が付着した)まで絞り、
170℃で3分間乾燥させた後、処理織物を
AATCC Test Method 118―1966法で測定した
とき、3以上即ちn―ヘキサデカンが織物に浸透
しないような撥油性を有するべきであり、また当
該有機フツ素化合物は、前記と同様の処理織物を
AATCC Test Method 22―1971スプレー法で
測定したとき50以上即ち水が織物の裏面へにじみ
出ないような撥水性を示すべきである。
次に本発明で使用される多官能イソシアネート
とは、分子中に2個以上のイソシアネート官能基
を含む有機化合物ならいずれでも良く、その一例
としては2,4―、2,6―トリレンジイソシア
ネート、トリメチロールプロパントリレンジイソ
シアネートアダクト、トリメチロールエタントリ
レンジイソシアネートアダクト、グリセリントリ
レンジイソシアネートアダクト、トリフエニルメ
タントリイソシアネート、4,4′―ジフエニルメ
タンジイソシアネート、ヘキサメチレンジイソシ
アネート、キシレンジイソシアネート、4,4′―
ジシクロヘキシルメタンジイソシアネートおよび
それらの混合物などがある。さらにポリオールと
過剰のポリイソシアネートであらかじめポリマー
化したイソシアネート官能基末端プレポリマーも
好ましく使用される。該化合物のイソシアネート
官能基はそのままでもあるいは安定化されていて
も良い。安定化剤としては、加熱時に解離して活
性なイソシアネート基が再生する程度に安定化す
るフエノール類、ε―カプロラクタム、マロン酸
ジエチルエステル、メチルエチルケトキシム、重
亜硫酸ソーダ、イミダゾール類などがある。
多官能イソシアネートは有機溶剤溶液あるいは
水分散液の形で配合することが多い。
撥水撥油性を有するフルオロアルキル基含有化
合物と多官能イソシアネートの配合比は、前者
100部に対して後者5〜300部が適当である。何故
ならば300部より多い場合は撥水撥油性が不足す
るし、5部より少ない場合はその耐ドライクリー
ニング性が劣るからである。多官能イソシアネー
トはあらかじめ撥水撥油剤に配合しておいても良
く、加工時に加工浴中に配合しても良い。
また多官能イソシアネートのほかに、柔軟にし
たり、帯電を防止したり、撥水撥油性を改良した
り、家庭洗濯に対する耐久性を改善したりする目
的で、帯電防止剤、アミノプラスト樹脂、アクリ
ルポリマー、天然ワツクス、シリコーン樹脂等を
本発明の効果が阻害されない程度に配合すること
もさしつかえない。
本発明の撥水撥油加工は、浸漬法のほかにスプ
レー、コーテイング法などでも実施できる。
対象となる繊維製品としては、例えば綿、絹、
羊毛、麻、レーヨンなどの天然繊維織物、又ナイ
ロン、ビニロン、ポリエステル、アクリルなどの
合成繊維織物、布、布製品、編物、不織布、衣
料、皮、合成皮革、皮製品、紙、紙製品などが挙
げられる。
本方法により処理された繊維製品は、ドライク
リーニング後の耐久性が改良されているが、それ
のみにとどまらず、家庭での水による洗濯後の耐
久性も改良されるとか加工後の風合がしつかりし
たものになるとか、意外な効果も見られる。
本発明をより詳述するために実施例及び比較例
をあげる。
実施例1〜4、比較例1
撥水撥油性能を有するフルオロアルキル基含有
化合物としてC8F17SO2N(CH3)CH2CH2OCOC
(CH3)=CH270部と、ステアリルメタクリレート
30部とを1,1,1―トリクロルエタン896部に
溶解し、重合開始剤としてアゾビスイソブチロニ
トリル1部及び重合調整剤としてラウリルメルカ
プタン3部を加え、80℃で4時間撹拌し、分子量
約20000の共重合体溶液(ポリマー濃度10%、F
―1と称す)を得た。本薬剤、多官能イソシアネ
ート及び1,1,1―トリクロルエタンで表―1
の如き加工浴を調合し、ナイロンタフタへ加工し
た結果を表―1に示す。この結果からもポリイソ
シアネートを併用した耐ドライクリーニング性能
は明白である。
試験方法
加工方法:浸漬絞り
絞り率 :90%(表―1)、100(表―2)
乾燥条件:(表―1)160℃×1分
(表―2)100℃×2分(予備乾燥)
160℃×2分(キユアリング)
撥水性 :AATCC Test :Method 22―1971
スプレーレイテイング法
撥油性 :AATCC Test Method 118―1966
ハイドロカーボンレジスタンス法
ドライクリーニング条件:加工布をその30重量倍
のパークレンと混合し、ラウンダメータ
ー中で室温下30分撹拌。風乾後140℃で
20秒間アイロンがけする。3回ドライク
リーニングとは以上の操作を3回繰返し
たことを言う。
The present invention relates to a water- and oil-repellent finishing method, particularly to a water- and oil-repellent finishing method for textile products that improves the deterioration of water- and oil-repellent performance after dry cleaning and washing. Currently, the mainstream of water and oil repellent finishing is a processing method in which a fluoroalkyl group-containing compound with a unique low surface energy is attached to textile products to repel not only water-based stains but also oil-based stains. It's on. Such processing methods are often carried out using an organic solvent solution or an aqueous dispersion of a fluoroalkyl group-containing compound that can serve as a water and oil repellent, but this compound may be washed off from the treated textile product, or If it is dissolved out, water and oil repellency will not be maintained. Particularly when dry cleaning textile products, dry cleaning solvents have recently been improved from kerosene to perchloroethylene, which has a strong dissolving power, and then to Freon (chlorofluoroethane), which is a water- and oil-repellent agent that can be used at the same time as cleaning dirt. Also, after dry cleaning, there is almost no water or oil repellency, and there is no dirt repellency. As a result of intensive research in order to improve this drawback, the present inventor has found that a textile product treated by blending a polyfunctional isocyanate with a fluoroalkyl group-containing compound that can be used as a water and oil repellent has significantly improved this drawback, and at the same time The present invention was completed based on the discovery that the various characteristics of the process were not impaired in any way. That is, the present invention provides water- and oil-repellent treatment of textile products with a fluoroalkyl group-containing compound having water and oil repellency, in which a polyfunctional isocyanate is added to 100 parts by weight (hereinafter simply referred to as "parts") of the fluoroalkyl group-containing compound. It relates to a water- and oil-repellent processing method for textile products, characterized by blending 5 to 300 parts of. The fluoroalkyl group-containing compound having water and oil repellency used in the present invention has a fluoroalkyl group having 3 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and is water-insoluble (1 at 25°C). It is a non-adhesive compound having a main transition temperature, that is, a melting point, a glass transition point, or a softening point of 20° C. or higher, and a molecular weight of about 700 to about 200,000. Examples of such organic fluorine compounds are as follows. (1) A homopolymer of a vinyl monomer having a fluoroalkyl group having 3 to 20 carbon atoms or a copolymer with a vinyl monomer that does not contain fluorine. Examples of vinyl monomers having a fluoroalkyl group include the following. C 7 F 15 CH 2 OCOCH=CH 2 C 8 F 17 SO 2 N (C 3 H 7 ) CH 2 CH 2 OCOCH=CH 2 C 8 F 17 SO 2 N (CH 3 ) CH 2 CH 2 OCOC (CH 3 )= CH2 C 7 F 15 CON (C 2 H 5 ) CH 2 CH 2 OCOC (CH 3 ) = CH 2 CF 3 (CF 2 ) 5 CH 2 CH 2 OCOCH = CH 2 CF 3 (CF 2 ) 9 CH 2 CH 2 OCH = CH 2 C 8 F 17 (CH 2 ) 11 OCOC (CH 3 ) = CH 2 (CF 3 ) 2 CFO (CH 2 ) 5 OCOCH=CH 2 C 8 F 17 SO 2 N (CH 2 CH 2 OCOCH=CH 2 ) 2 C 8 F 17 SO 2 N (CH 3 ) (CH 2 ) 10 COOCH 2 CH=CH 2 C 8 F 17 SO 2 N (C 2 H 5 ) CH 2 CH 2 OCOCH=CHCOOC 4 H 9 C 6 F 13 SO 2 N(CH 3 )CH 2 CH 2 OCOCH=CH 2 C 8 F 17 SO 2 NHCH 2 CH 2 SO 2 CH=CH 2 Fluorine Examples of vinyl monomers that do not include ethylene, propylene, butylene, butadiene, isoprene, chloroprene, vinyl chloride, vinylidene chloride, styrene, alcohols or alkyl amines of (meth)acrylic acid (all have 20 carbon atoms or less) Examples include esters or amides of , diacetone acrylamide, N-methylol acrylamide, acrylonitrile, acrylamide, vinyl acetate, and vinyl compounds having a siloxane bond. Any of the monomers can also be used in combination. These homopolymers or copolymers can be produced by known methods of vinyl polymerization, and for example, solution polymerization and emulsion polymerization using a radical initiator are common. The molecular weight of the polymer can be adjusted within a preferred range by adjusting the concentration of the initiator and the type and concentration of the chain transfer agent, but is generally preferably 3000 or more. (2) A (poly)ester of a monohydric or polyhydric alcohol containing a fluoroalkyl group having 3 to 20 carbon atoms and an optionally fluorinated monohydric or polyhydric carboxylic acid. A (poly)ester of an optionally fluorinated monohydric or polyhydric alcohol and a monohydric or polyhydric carboxylic acid having a fluoroalkyl group having 3 to 20 carbon atoms. Examples of components used in this case are listed below. C 9 F 19 CH 2 CH 2 OH C 8 F 17 SO 2 N (C 3 H 7 ) CH 2 CH 2 OH C 8 F 17 SO 2 N (CH 2 CH 2 OH) 2 C 8 F 17 SO 2 N( C 2 H 5 )CH 2 CH(OH)CH 2 OH C 7 F 15 COOH C 8 F 17 SO 2 N(C 3 H 7 )CH 2 COOH Benzoic acid, adipic acid, sebacic acid, phthalic acid, maleic acid, trimellitic acid ethylene glycol monomethyl ether, ethylene glycol, propylene glycol, diethylene glycol, glycerin, polypropylene glycol, 2-ethylhexanol, stearyl alcohol, the (poly)ester has a molecular weight is preferably 1000 or more. (3) Monohydric or polyhydric alcohol having a fluoroalkyl group having 3 to 20 carbon atoms (in some cases, fluorine-free monohydric or polyhydric alcohol may be mixed) and monohydric or polyhydric isocyanate. , such as phenyl isocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate,
(Poly)urethane with polymethylene polyphenyl isocyanate. The (poly)urethane preferably has a molecular weight of 700 or more. (4) Epoxy compounds having a fluoroalkyl group having 3 to 20 carbon atoms, e.g. Homopolymers of and preferably copolymers with fluorine-free epoxy compounds such as propylene oxide and epichlorohydrin. The molecular weight of such a polymer is preferably 3000 or more. Therefore, the fluoroalkyl group-containing compound used in the present invention is prepared by making a diluted solution (solution or dispersion) with a concentration of 0.5% by weight, and adding 100% of polyester
Soak processed yarn fabric and wet pick up 100%
Squeeze until the diluent has adhered to the same weight as the fabric.
After drying at 170℃ for 3 minutes, the treated fabric was
When measured by AATCC Test Method 118-1966 method, it should have an oil repellency of 3 or more, that is, n-hexadecane does not penetrate into the fabric, and the organic fluorine compound should
It should exhibit water repellency of 50 or higher when measured using the AATCC Test Method 22-1971 spray method, meaning that water does not bleed onto the back side of the fabric. Next, the polyfunctional isocyanate used in the present invention may be any organic compound containing two or more isocyanate functional groups in the molecule, examples of which include 2,4-, 2,6-tolylene diisocyanate, Trimethylolpropane tolylene diisocyanate adduct, trimethylolethane tolylene diisocyanate adduct, glycerin tolylene diisocyanate adduct, triphenylmethane triisocyanate, 4,4'-diphenylmethane diisocyanate, hexamethylene diisocyanate, xylene diisocyanate, 4,4'-
These include dicyclohexylmethane diisocyanate and mixtures thereof. Furthermore, isocyanate-functional group-terminated prepolymers which have been prepolymerized with a polyol and an excess of polyisocyanate are also preferably used. The isocyanate functionality of the compound may be intact or stabilized. Stabilizers include phenols, ε-caprolactam, malonic acid diethyl ester, methyl ethyl ketoxime, sodium bisulfite, and imidazoles, which are stabilized to the extent that they dissociate upon heating and regenerate active isocyanate groups. Polyfunctional isocyanates are often blended in the form of organic solvent solutions or aqueous dispersions. The blending ratio of the fluoroalkyl group-containing compound having water and oil repellency and the polyfunctional isocyanate is
The latter 5 to 300 copies per 100 copies is appropriate. This is because if the amount is more than 300 parts, the water and oil repellency will be insufficient, and if it is less than 5 parts, the dry cleaning resistance will be poor. The polyfunctional isocyanate may be added to the water and oil repellent in advance, or may be added to the processing bath during processing. In addition to polyfunctional isocyanates, antistatic agents, aminoplast resins, and acrylic polymers are used to soften, prevent static, improve water and oil repellency, and improve durability against home washing. , natural wax, silicone resin, etc. may be added to the extent that the effects of the present invention are not impaired. The water and oil repellent finishing of the present invention can be carried out by spraying, coating, etc. in addition to the dipping method. Target textile products include cotton, silk,
Natural fiber fabrics such as wool, linen, rayon, synthetic fiber fabrics such as nylon, vinylon, polyester, acrylic, cloth, cloth products, knitted fabrics, non-woven fabrics, clothing, leather, synthetic leather, leather products, paper, paper products, etc. Can be mentioned. Textile products treated with this method have improved durability after dry cleaning, but not only that, but also improved durability after washing with water at home and improved texture after processing. There are also some surprising effects, such as making it more firm. Examples and comparative examples will be given to explain the present invention in more detail. Examples 1 to 4, Comparative Example 1 C8F17SO2N ( CH3 ) CH2CH2OCOC as a fluoroalkyl group-containing compound having water and oil repellency
(CH 3 ) = 70 parts of CH 2 and stearyl methacrylate
30 parts of 1,1,1-trichloroethane was dissolved in 896 parts of 1,1,1-trichloroethane, 1 part of azobisisobutyronitrile as a polymerization initiator and 3 parts of lauryl mercaptan as a polymerization modifier were added, and the mixture was stirred at 80°C for 4 hours. Copolymer solution with a molecular weight of approximately 20,000 (polymer concentration 10%, F
-1) was obtained. Table 1 for this drug, polyfunctional isocyanate and 1,1,1-trichloroethane
Table 1 shows the results of preparing a processing bath and processing it into nylon taffeta. From this result as well, the dry cleaning resistance performance of using polyisocyanate in combination is clear. Test method Processing method: Immersion squeezing Squeezing ratio: 90% (Table-1), 100 (Table-2) Drying conditions: (Table-1) 160℃ x 1 minute (Table-2) 100℃ x 2 minutes (pre-drying ) 160℃ x 2 minutes (curing) Water repellency: AATCC Test: Method 22-1971
Spray rating method oil repellency: AATCC Test Method 118-1966
Hydrocarbon resistance method dry cleaning conditions: Mix the processed fabric with 30 times its weight of perchloren and stir in a rounder meter at room temperature for 30 minutes. After air drying at 140℃
Iron for 20 seconds. 3-time dry cleaning means that the above operation is repeated three times.
【表】【table】
【表】
実施例5〜7、比較例3、4
撥水撥油性を有するフルオロアルキル基含有化
合物としてC8F17SO2N(CH3)CH2CH2OCOCH
=CH2 85部、2―エチルヘキシルメタクリレー
ト10部、N―メチロールアクリルアミド5部を、
オクタデシルジメチルアミン・酢酸塩2部、およ
びポリエチレンオキシドノニルフエニルエーテル
〔HLB20〕5部で乳化重合した分散液(ポリマー
濃度20%、F―2と称す)を使用した。
多官能イソシアネートとして、1,6―ヘキサ
ンジオール・アジペート(数平均分子量3000)・
トリレンジイソシアネートアダクト(イソシアネ
ート基はメチルエチルケトキシムでブロツク)な
るイソシアネート官能基末端プレポリマー100部
をオクタデシルジメチルアミン・酢酸塩5部で乳
化した分散液(有効成分濃度20%、P―1と称
す)を使用した。両者を併用してポリエステル/
綿(65/35)混紡(ポプリン)へ加工した結果を
表―2に示す。[Table] Examples 5 to 7, Comparative Examples 3 and 4 C 8 F 17 SO 2 N (CH 3 ) CH 2 CH 2 OCOCH as a fluoroalkyl group-containing compound having water and oil repellency
= 85 parts of CH 2 , 10 parts of 2-ethylhexyl methacrylate, 5 parts of N-methylolacrylamide,
A dispersion (polymer concentration 20%, referred to as F-2) obtained by emulsion polymerization with 2 parts of octadecyldimethylamine acetate and 5 parts of polyethylene oxide nonyl phenyl ether [HLB20] was used. As a polyfunctional isocyanate, 1,6-hexanediol adipate (number average molecular weight 3000)
A dispersion (active ingredient concentration 20%, referred to as P-1) in which 100 parts of an isocyanate functional group-terminated prepolymer called tolylene diisocyanate adduct (isocyanate groups are blocked with methyl ethyl ketoxime) is emulsified with 5 parts of octadecyldimethylamine acetate is prepared. used. Using both together, polyester/
Table 2 shows the results of processing into a cotton (65/35) blend (poplin).
【表】
実施例 8
C8F17SO2N(CH3)CH2CH2OCOCH=CH2の
70部とステアリルアクリレートの30部とを1,
1,1―トリクロルエタンの900部に溶解してか
ら、アゾビスイソブチロニトリルの1.0部および
ラウリルメルカプタンの3部を加えて80℃で4時
間撹拌下に重合反応を行なつて分子量が約20000
なる共重合体の溶液(ポリマー濃度10%;F―3
と称す)を得た。
次いで、表―3に示される如き配合組成にて加
工浴を調合し、実施例1〜4と同様にしてナイロ
ン・タフタへ加工した結果を同表にまとめて示
す。
なお、各種の性能評価試験は次のような要領で
行なつたものである。
試験方法
乾燥条件としては160℃に1分間なる条件を採
用し、それ以外の撥水性、撥油性およびドライク
リーニング条件はすべて実施例1〜4の場合と同
様とし、耐洗濯性の試験だけは次のような方法に
よつた。
洗濯条件:0.1%の中性洗剤を含有する40℃の浴
25に対して試験片を浴比が1:30となるよう
に入れ、5分間に亘つて洗濯し、次いで4分間
かけて脱水をして乾燥させたのち140℃の温度
で20秒間アイロンがけを行なつて、これを1回
洗濯とし、かかるサイクルを都合5回行なつて
耐洗濯性の試験とした。[Table] Example 8 C 8 F 17 SO 2 N (CH 3 ) CH 2 CH 2 OCOCH=CH 2
70 parts and 30 parts of stearyl acrylate in 1,
After dissolving in 900 parts of 1,1-trichloroethane, 1.0 part of azobisisobutyronitrile and 3 parts of lauryl mercaptan were added, and a polymerization reaction was carried out with stirring at 80°C for 4 hours to obtain a molecular weight of approximately 20000
A solution of copolymer (polymer concentration 10%; F-3
) was obtained. Next, a processing bath was prepared with the composition shown in Table 3, and processed into nylon taffeta in the same manner as in Examples 1 to 4. The results are summarized in the same table. The various performance evaluation tests were conducted in the following manner. Test method The drying conditions were 160℃ for 1 minute, and all other water repellency, oil repellency, and dry cleaning conditions were the same as in Examples 1 to 4. Only the washing resistance test was performed as follows. I used a method like this. Washing conditions: 40℃ bath containing 0.1% neutral detergent
The test piece was placed in a bath with a bath ratio of 1:30 and washed for 5 minutes, then dehydrated for 4 minutes, dried, and then ironed at 140℃ for 20 seconds. The washing resistance was tested by repeating this cycle 5 times in total.
【表】【table】
【表】【table】
【表】
この結果からも明らかなように、本発明の方法
に従つて得られる加工繊維製品は耐久性にすぐれ
るものであり、耐ドライクリーニング性ばかりで
はなく、耐洗濯性も改善されるものであることが
知れる。[Table] As is clear from the results, the processed fiber products obtained according to the method of the present invention have excellent durability, and have improved not only dry cleaning resistance but also washing resistance. It is known that
Claims (1)
化合物で繊維製品の撥水撥油加工を行なうに際
し、前記フルオロアルキル基含有化合物100重量
部に対し多官能イソシアネートを5〜300重量部
配合することを特徴とする繊維製品の撥水撥油加
工法。1. When performing water and oil repellent treatment on textile products with a fluoroalkyl group-containing compound having water and oil repellency, 5 to 300 parts by weight of a polyfunctional isocyanate is blended to 100 parts by weight of the fluoroalkyl group-containing compound. Water and oil repellent processing method for textile products.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6778280A JPS56165072A (en) | 1980-05-23 | 1980-05-23 | Water and oil repellent process |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6778280A JPS56165072A (en) | 1980-05-23 | 1980-05-23 | Water and oil repellent process |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS56165072A JPS56165072A (en) | 1981-12-18 |
JPS636676B2 true JPS636676B2 (en) | 1988-02-10 |
Family
ID=13354866
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP6778280A Granted JPS56165072A (en) | 1980-05-23 | 1980-05-23 | Water and oil repellent process |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS56165072A (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59111121U (en) * | 1983-01-14 | 1984-07-26 | グンゼ株式会社 | sanitary shorts |
JPS60194182A (en) * | 1984-03-12 | 1985-10-02 | ユニチカユ−エムグラス株式会社 | Treatment of glass cloth |
JPS6119684A (en) * | 1984-07-06 | 1986-01-28 | Meisei Kagaku Kogyo Kk | Water-and oil-repellent agent having improved durability |
JPS6216454A (en) * | 1985-07-15 | 1987-01-24 | Dainippon Ink & Chem Inc | Blocked polyisocyanate compound, water and oil-repellent agent and treatment therewith |
US6309752B1 (en) * | 1991-04-02 | 2001-10-30 | 3M Innovative Properties Company | Substrate having high initial water repellency and a laundry durable water repellency |
US6586522B1 (en) | 2000-06-12 | 2003-07-01 | 3M Innovative Properties Company | Water- and oil-repellent composition |
JP2003171880A (en) * | 2001-12-07 | 2003-06-20 | Nicca Chemical Co Ltd | Method for producing water and oil repellent fibrous product |
JP5789090B2 (en) | 2010-07-30 | 2015-10-07 | 日華化学株式会社 | Water / oil repellent composition, functional fiber product and method for producing functional fiber product |
JP2017040026A (en) * | 2015-08-21 | 2017-02-23 | 株式会社Toscom | Method for producing water-repellent clothing, and water-repellent clothing |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4843096A (en) * | 1971-09-27 | 1973-06-22 | ||
JPS48103900A (en) * | 1972-03-06 | 1973-12-26 | ||
JPS54133486A (en) * | 1978-04-07 | 1979-10-17 | Asahi Glass Co Ltd | Water and oil repellent composition with improved durability |
JPS5518246A (en) * | 1978-07-27 | 1980-02-08 | Gadelius Kk | Gas absorption unit |
JPS5580583A (en) * | 1978-12-06 | 1980-06-17 | Daiichi Lace Kk | Production of coating cloth |
JPS636676A (en) * | 1986-06-27 | 1988-01-12 | Fujitsu Ltd | Stroke instructing system |
-
1980
- 1980-05-23 JP JP6778280A patent/JPS56165072A/en active Granted
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4843096A (en) * | 1971-09-27 | 1973-06-22 | ||
JPS48103900A (en) * | 1972-03-06 | 1973-12-26 | ||
JPS54133486A (en) * | 1978-04-07 | 1979-10-17 | Asahi Glass Co Ltd | Water and oil repellent composition with improved durability |
JPS5518246A (en) * | 1978-07-27 | 1980-02-08 | Gadelius Kk | Gas absorption unit |
JPS5580583A (en) * | 1978-12-06 | 1980-06-17 | Daiichi Lace Kk | Production of coating cloth |
JPS636676A (en) * | 1986-06-27 | 1988-01-12 | Fujitsu Ltd | Stroke instructing system |
Also Published As
Publication number | Publication date |
---|---|
JPS56165072A (en) | 1981-12-18 |
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