JPH0512474B2 - - Google Patents
Info
- Publication number
- JPH0512474B2 JPH0512474B2 JP11870284A JP11870284A JPH0512474B2 JP H0512474 B2 JPH0512474 B2 JP H0512474B2 JP 11870284 A JP11870284 A JP 11870284A JP 11870284 A JP11870284 A JP 11870284A JP H0512474 B2 JPH0512474 B2 JP H0512474B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- treatment
- parts
- fibers
- epoxy 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 - Lifetime
Links
- 239000000835 fiber Substances 0.000 claims description 43
- 102000004169 proteins and genes Human genes 0.000 claims description 32
- 108090000623 proteins and genes Proteins 0.000 claims description 32
- 239000004593 Epoxy Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000004088 foaming agent Substances 0.000 claims description 19
- 239000006260 foam Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000012545 processing Methods 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000004744 fabric Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- -1 yarns Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 230000037303 wrinkles Effects 0.000 description 6
- RTLULCVBFCRQKI-UHFFFAOYSA-N 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC1=NC(Cl)=NC(Cl)=N1 RTLULCVBFCRQKI-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 210000004209 hair Anatomy 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl 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
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229940046413 calcium iodide Drugs 0.000 description 2
- 229910001640 calcium iodide Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000000051 modifying effect Effects 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ALWXETURCOIGIZ-UHFFFAOYSA-N 1-nitropropylbenzene Chemical compound CCC([N+]([O-])=O)C1=CC=CC=C1 ALWXETURCOIGIZ-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- PIKOWWRXMZFLLH-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CC1OC1 PIKOWWRXMZFLLH-UHFFFAOYSA-N 0.000 description 1
- AGXAFZNONAXBOS-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethyl)phenyl]methyl]oxirane Chemical compound C=1C=CC(CC2OC2)=CC=1CC1CO1 AGXAFZNONAXBOS-UHFFFAOYSA-N 0.000 description 1
- ZSBIECRLTCKCHE-UHFFFAOYSA-N 2-chloro-2-(chloromethyl)oxirane Chemical compound ClCC1(Cl)CO1 ZSBIECRLTCKCHE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IWYRWIUNAVNFPE-UHFFFAOYSA-N Glycidaldehyde Chemical compound O=CC1CO1 IWYRWIUNAVNFPE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- 235000016976 Quercus macrolepis Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- LKZCRGABYQYUFX-UHFFFAOYSA-L barium(2+);dithiocyanate Chemical compound [Ba+2].[S-]C#N.[S-]C#N LKZCRGABYQYUFX-UHFFFAOYSA-L 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- CCOPUGSPAPWFFC-UHFFFAOYSA-L disodium 4-hydroxy-3-[[4-[4-[(2-hydroxynaphthalen-1-yl)diazenyl]-2-methylphenyl]-3-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Cc1cc(ccc1-c1ccc(cc1C)N=Nc1c(O)ccc2ccccc12)N=Nc1c(O)c2ccc(cc2cc1S([O-])(=O)=O)S([O-])(=O)=O CCOPUGSPAPWFFC-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VKMUVHUFUIYSMS-UHFFFAOYSA-N ethyl 9-(oxiran-2-yl)nonanoate Chemical compound CCOC(=O)CCCCCCCCC1CO1 VKMUVHUFUIYSMS-UHFFFAOYSA-N 0.000 description 1
- OXVXWUDYARFPLN-UHFFFAOYSA-N ethylazanium;hydron;sulfate Chemical compound CC[NH3+].OS([O-])(=O)=O OXVXWUDYARFPLN-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- VAUOPRZOGIRSMI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CNC1=CC=CC=C1 VAUOPRZOGIRSMI-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- NCGARFWFKHNMJK-UHFFFAOYSA-N oxiran-2-ylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1CO1 NCGARFWFKHNMJK-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
産業上の利用分野
本発明は、タンパク繊維やタンパク繊維を含む
糸、織布、不織布のような製品の処理方法、さら
に詳しくいえば、防しわ性、防縮性、耐光性、耐
薬品性、防かび性などの性質を恒久的に改善する
ための処理方法に関するものである。
従来の技術
従来、タンパク質製品にエポキシ化合物を反応
させて防しわ性、防縮性、耐光性、耐薬品性など
を向上させることは知られている。
しかしながら、このような改質に際しては、水
酸化アルカリ、炭酸アルカリなどの強アルカリ
や、四塩化スズ、三フツ化ホウ素のような強酸性
物質を触媒として用いなければならないため、繊
維が劣化するのを免れない。このような欠点を改
良するものとして、有機アミンを用いる方法も提
案されているが(特開昭38−25198号公報)、この
方法では十分な改質効果が得られない。
発明が解決しようとする課題
本発明者らは、このような従来のエポキシ化合
物によるタンパク繊維の改質方法における欠点を
克服するために種々研究を重ね、先に中性塩触媒
の存在下でタンパク繊維のエポキシ化を行う方法
を提案した(特公昭47−24199号公報、特公昭52
−38131号公報)。
しかしながら、この方法ではタンパク繊維に対
し、10倍以上という大量の処理液を必要とするた
め、エポキシ化合物の使用量はタンパク繊維と同
量もしくはそれ以上になり、また加熱処理する際
に多量のエネルギーと時間を要するという欠点が
ある。
本発明の目的は、処理液の量をできるだけ少な
くし、少ないエネルギー消費で、かつ短時間で効
率よくタンパク繊維のエポキシ化を行い得る方法
を提供するものである。
課題を解決するための手段
本発明者らは、タンパク繊維のエポキシ化を少
ない処理液により迅速かつ効果的に行う方法を開
発するために、鋭意研究を重ねた結果、高濃度で
エポキシ化合物を含む処理液を泡状で含浸させ、
そのまま予備乾燥することなしにマイクロ波照射
処理することによりその目的を達成しうることを
見出し、この知見に基づいて本発明をなすに至つ
た。
すなわち、本発明に従えば、タンパク繊維又は
その製品に、アルカリ金属又はアルカリ土類金属
の中から選ばれた金属の中性塩又は弱塩基性塩と
エポキシ化合物と起泡剤及び場合によりさらに染
料を含む泡状組成物を含浸させ、そのままマイク
ロ波照射処理することにより、タンパク繊維又は
その製品の長所をそこなうことなく効率よく改質
を行うことができる。
本発明方法においては、エポキシ化触媒とし
て、アルカリ金属又はアルカリ土類金属の中性塩
又は弱塩基性塩を用いる必要かあるが、このよう
なものとしては、リチウム、ナトリウム、カリウ
ム、ルビジウム、オスミウムのようなアルカリ金
属やベリリウム、マグネシウム、カルシウム、ス
トロンチウム、バリウムのようなアルカリ土類金
属の水溶性中性塩ないしは弱塩基性塩で、1規定
水溶液のPHが5.5〜9.0の範囲内にあるものが望ま
しい。このアルカリ金属の塩としては、例えばフ
ツ化ナトリウム、塩化ナトリウム、臭化ナトリウ
ム、硝酸ナトリウム、硫酸ナトリウム、酢酸ナト
リウム、亜硝酸ナトリウム、チオシアン酸ナトリ
ウム、チオ硫酸ナトリウム及び相当するリチウム
塩、カリウム塩、オスミウム塩、ルビジウム塩
を、また、アルカリ土類金属の塩としては、チオ
シアン酸バリウム、チオシアン酸カルシウム、ヨ
ウ化カルシウム、塩化バリウム、塩化カルシウ
ム、ヨウ化カルシウム、塩化ストロンチウム、塩
化マグネシウムなどがある。
これらの塩は、通常0.1〜3規定の濃度で用い
られる。これよりも低い濃度では、反応促進効果
が不十分であるし、またこれよりも高い濃度で
は、マイクロ波照射、繊維の処理条件によつて繊
維が部分的に溶解する危険がある。
一般に、羊毛や兎毛など獣毛繊維の場合で0.1
〜0.5規定、絹繊維の場合で0.1〜1.5規定の範囲が
望ましい。
次に本発明方法で用いるエポキシ化合物として
は、これまでタンパク繊維のエポキシ化に通常使
用されているものの中から任意に選ぶことができ
る。このような化合物としては、例えば一般式
(ただし、R1、R2、R3およびR4は水素原子また
は式化合物を安定に存在せしめ、かつタンパク繊
維との反応を妨げない任意の有機残基で、相互に
連結して環を形成することもできる基で、それら
の有機残基としては、ニトロ基、シアノ基、ハロ
ゲン基、カルボキシル基、カルボニル基、ヒドロ
キシル基、アミノ基、アルコキシル基、エポキシ
基や、それらの基を置換したあるいは置換しない
アルキル、アルケニル、アルキニル、アラリキ
ル、アリール、アルコキシ、アリールオキシ、ア
リルなどの基である)
で表わされる化合物を挙げることができる。これ
らの化合物には、例えばプロピレンオキシド、ブ
タジエンモノオキシド、スチレンオキシド、ビニ
ルシクロヘキサンオキシドのようなアルキレンオ
キシド類、フエニルグリシジルエーテル、ブチル
グリシジルエーテル、ビスフエノールAのジグリ
シジルエーテル、グリセリンのトリグリシジルエ
ーテルなどのグリシジルエーテル類、安息香酸グ
リシジル、グリシジルメタクリレートのようなグ
リシジルエステル類、10,11−エポキシウンデカ
ン酸エチルのようなエポキシ酸のエステルやアミ
ド類、アルキルグリシジルウレタン類、グリシジ
ルメチルスルホネートやジメチルアルキル2、3
−エポキシアルキルオキシシランのようなスルホ
ン酸グリシジルエステル類やエポキシシラン類、
グリシドールのようなエポキシアルコール類、グ
リシジルアニリンのようなエポキシアミン類、グ
リシジル安息香酸のようなエポキシ酸類、エピク
ロルヒドリンやエピブロモヒドリンなどのハロゲ
ン化エポキシド類、グリシジルアルデヒドのよう
なカルボニルエポキシド類などが包含される。
これらのエポキシ化合物は1種又は2種以上混
合して使用することができるが、エポキシ化合物
分子中のエポキシ基の数、反応性、エポキシ化合
物の相互作用を考慮し、かつ加工タンパク繊維の
種類と使途に適応するごとく選択して、適宜反応
する処理条件を決定することが肝要である。
かかるエポキシ化合物はそのまま使用できる
が、適当な溶媒に溶解してもよい。すなわち水溶
性の場合は、そのまま水溶液として使用される
が、水不溶性のものは、メタノール、エタノー
ル、イソプロパノール、アセトン、ジオキサンな
どの水溶性溶剤と水との混合溶媒に溶解するか、
又は適当な方法で乳化分散液として、適当な非水
溶媒に溶解して使用できる。使用するエポキシ化
合物の量は、タンパク繊維の種類、組織などの
他、エポキシ化合物の種類によつても異なるが、
タンパク繊維の重量に対して2〜30%、好ましく
は6〜20%である。
なお、本発明における処理工程は、タンパク繊
維に塩とエポキシ化合物とを含む泡状組成物を泡
含させて圧搾消泡し、マイクロ波照射処理後洗浄
するものであるが、マイクロ波照射時間は、タン
パク繊維の種類や組織、使途及びエポキシ化合物
の反応性、加工処理液に含まれる非水溶媒や添加
物の種類や量によつても異なる。また、当然のこ
とながら、マイクロ波の出力(通常使用できるの
では、2450MHz〜25kw及び900MHz〜25kwであ
る)や加熱方式の差異(箱型オーブンや導波管オ
ーブンなど)によつても異なるが、10秒〜10分、
好ましくは30秒〜5分である。このような条件で
の処理では触媒が中性塩もしくは弱塩基性塩であ
り、かつ単時間での処理のためタンパク繊維の黄
変は起らない。
本発明で採用した泡加工法、すなわち、泡を形
成しうる少量の処理液に繊維状及び他の多孔性基
質を接触させて均一な仕上品を得る方法は公知で
あるが、起泡剤の存在下0.25:1〜5:(重量)
の処理液の材料に対する比率で繊維材料に触媒と
エポキシ化合物とを接触させ、触媒とエポキシ化
合物とが繊維材料全体に均一に分配されるような
工程である。処理液の材料に対する比率は好まし
くは0.5:1〜3:1(重量)であり、さらに好ま
しくは1:1〜1.5:1(重量)である。本工程は
パツテイング又は浸漬加工し得るすべての種類の
多孔性、特に繊維状、織物状材料例えばバラ毛フ
イラメント、篠、糸、編物、織物またはタフテツ
ド製品、不織布、ビロアド、カーペツト及びフエ
ルトなどに適用できる。起泡剤は公知のもの、す
なわちアニオン性、カチオン性、両性又は非イン
オ性剤が用いられるが、本発明で使用するエポキ
シ化合物と相容性を有するものでなけれはならな
いが、処理工程中不活性でなくてはならないの
で、一般には非イオン性起泡剤が好ましい。使用
する起泡剤の種類は処理液のPH、用いる触媒、エ
ポキシ化合物の他に、後述のような染料を併用す
る場合には、染料又は他の添加剤との相容性や相
互作用の有無によつて選択される。
起泡剤としては、部分カルボキシメチル化アル
キル−、アリール−、アルキルアリール−又はア
リールアルキル−ポリグリコールエーテル、アル
カン−、アルキルベンゼン−及びアルキルナフタ
リンスルホネート、第一又は第二アルキルサルフ
エート、アルキルポリグリコール−、アルキル−
フエニルポリグリコール−及びジアルキルフエニ
ルポリグリコールエーテルサルフエート、スルホ
ン化又は硫酸化油、脂肪酸タウリド、及び脂肪酸
サルフエートエチルアミドなどのアニオン性剤が
ある。適当な非イオン性起泡剤としてはエチレン
オキシド8〜50モルと脂肪酸アルコール、脂肪
酸、脂肪酸アミド、アルキルメルカプタン又はア
ルキルフエノールとを反応させた水溶性付加物が
ある。エチレンオキシド8〜100モルと脂肪族ア
ルキルアミン又は脂肪族アルキルポリアミドとの
反応により得られる付加物及びそれら四級化誘導
体などのカチオン性起泡剤や、脂肪酸サルフエー
ト−エチルアミノエチルアミド、脂肪酸γ−スル
ホ−β−ヒドロキシ−プロピルアミノエチルアミ
ドなどの両性起泡剤がある。
本発明に用いる泡状組成物は、上記触媒塩、エ
ポキシ化合物、起泡剤及び水や有機溶媒の他に、
必要ならば加工助剤例えば乳化剤、のり剤、他の
塩類、キヤリヤーなどを加えてもよい。泡状組成
物は通常市販の発泡装置によつて、空気もしくは
任意の不活性ガスを使用して得られる。すなわち
一般的に計量された量の不活性ガスと、繊維に塗
布すべき処理剤を含有する処理液とを混合し、該
混合物を泡に変えることのできる機器ならすべて
用いることができる。
泡を製造するのに用いられる組成物は起泡剤を
0.2〜5重量%、好ましくは0.4〜2重量%の濃度
で、濃度にして0.1〜3規定の触媒塩と、エポキ
シ化合物を5〜80重量%、好ましくは10〜60重量
%、有機溶剤1〜5重量%を含有し、水が全組成
の残余重量を補充している。随意成分として
0.001〜2重量%、好ましくは0.01〜1.0重量%の
湿潤剤を加えることもできるが、発泡剤が十分に
湿潤作用を提供する場合には全く加える必要はな
い。起泡性のあるエポキシ化合物を用いる場合に
は起泡剤の量を減らすか、全く添加する必要のな
い場合もある。泡の密度は1c.c.当り0.005〜0.3
g、好ましくは1c.c.当り0.01〜0.2gにわたつて
変動することができるし、泡の平均径は0.05〜
0.5mm、好ましくは0.08〜0.45mmである。
このようにしてエポキシ化合物と反応させた、
タンパク繊維は常法に従つてソーピング、水洗し
たのち乾燥させる。本発明方法により処理された
タンパク繊維は耐アルカリ性、耐酸性、耐変色
性、防しわ性、防縮性が著しく改善されている。
なお、塩類と同時に、タンパク繊維を染色し得る
染料を同時に添加したエポキシド含有処理用泡組
成物をタンパク繊維に包含させた後、マイクロ波
照射処理をすれば、前記タンパク繊維の恒久的改
質の他に染色をも同時に実施することができる。
使用できる染料としてはプロシオンスカーレツ
トHR、プロシオンブルーH5RS、プロシオンブ
リリアントオレンジGSなどプロシオン系、ミカ
シオンスカーレツト2G、ミカシオンレツドBな
どミカシオン系レマゾールゴールデンエローGな
どレマゾール系、ダイヤミラブリリアントレツド
BB、ダイヤミラブリリアントオレンジGGDなど
ダイヤミラ系などを挙げることができる。
発明の効果
本発明に従えば、タンパク繊維に反応触媒及び
エポキシ化合物を含む処理液を泡状で含浸させた
のち、そのまま予備乾燥せずにマイクロ波照射処
理を行うことにより、少ない量の処理液及びエポ
キシ化合物で効率よく改質処理を行うことができ
るので原料ロスを大巾に防ぐことができる上、時
間面、エネルギー面でも従来の方法よりもはるか
に節約をはかることができる。
実施例
次に実施例によつて本発明を詳しく説明する。
実施例 1
ビニルシクロヘキセンジオキシド10重量部、二
量化リノール酸ジグリシジエステル20重量部、フ
エニルグリシジルエーテル10重量部、酸素数11〜
15の鎖状第二アルコールのエチレンオキシド20モ
ル付加物からなる起泡剤1.3重量部、n−オクタ
ン5重量部、炭素数11〜15の鎖状第二アルコール
のエチレンオキシド9モル付加物からなる安定剤
0.5重量部、低分子量ポリエチレンと非イオン性
界面活性剤とを含む乳濁液15重量部、シリコーン
系湿潤剤0.2重量部に、濃度が1Nになるように
Na2S2O3水溶液を加えた処理液を市販のオークス
型混合機中で発泡させた。該泡状組成物を、精練
漂白した16匁付絹羽二重にアプリケーターを用い
て塗布含浸させ150%に圧搾含浸させた。該処理
液含浸繊維を予備乾燥することなくそのままガラ
ス容器内に密閉し、2450MHz箱型オーブンに入
れ、600Wで3分マイクロ波処理した。処理液洗
剤を含む80℃の熱水で洗浄、水洗して乾燥した。
処理織物の重量増加率は13%、モンサント法によ
る防しわ度(たて方向)は乾燥時で71%、湿潤時
69%であり、未処理織物のそれぞれ59%、55%に
比して大巾に増加していた。また1規定の
NaOH溶液による65℃、1時間のアルカリ溶解
度試験の結果は未処理試料57%に対して11%、3
規定HCl溶液による65℃、1時間の酸溶解度試験
の結果は、未処理試料の48%に対して6.4%で大
巾な耐薬品性の向上が得られた。収縮率は未処理
の2.5%に対して1.4%であつた。
実施例 2〜13
実施例1のNa2S2O3の代りに種々の塩(濃度
0.8N)を触媒として添加した、実施例1と同様
の組成からなる泡状組成物を用いて、実施例1と
同様に処理した絹織物の重量増加率と耐アルカリ
性とを使用した塩の種類、マイクロ波処理条件に
対して示すと第1表のようになる。これらはいず
れも未処理のものと白度、風合は変らず、アルカ
リ溶解度はもとより、酸溶解度、防しわ性共に未
処理織物よりもすぐれていた。
INDUSTRIAL APPLICATION FIELD The present invention relates to a method for treating protein fibers and products containing protein fibers, such as yarns, woven fabrics, and non-woven fabrics, and more specifically, to provide wrinkle resistance, shrink resistance, light resistance, chemical resistance, and It relates to a treatment method for permanently improving properties such as moldiness. BACKGROUND ART Conventionally, it has been known to improve wrinkle resistance, shrink resistance, light resistance, chemical resistance, etc. by reacting protein products with epoxy compounds. However, such modification requires the use of strong alkalis such as alkali hydroxide and alkali carbonate, and strong acids such as tin tetrachloride and boron trifluoride as catalysts, which can lead to fiber deterioration. I can't escape it. A method using an organic amine has been proposed as a method for improving these drawbacks (Japanese Patent Application Laid-open No. 38-25198), but this method does not provide a sufficient modifying effect. Problems to be Solved by the Invention The present inventors have conducted various studies in order to overcome the drawbacks of such conventional methods for modifying protein fibers using epoxy compounds. proposed a method for epoxidizing fibers (Japanese Patent Publication No. 47-24199, Japanese Patent Publication No. 52
-38131). However, this method requires a large amount of treatment solution, more than 10 times the amount of protein fiber, so the amount of epoxy compound used is the same or more than the amount of protein fiber, and a large amount of energy is required during heat treatment. The disadvantage is that it takes time. An object of the present invention is to provide a method that can efficiently epoxidize protein fibers in a short period of time while minimizing the amount of processing liquid and consuming less energy. Means for Solving the Problems In order to develop a method for quickly and effectively epoxidizing protein fibers using a small amount of treatment liquid, the present inventors have conducted extensive research and found that Impregnated with processing liquid in the form of foam,
It was discovered that the object could be achieved by applying microwave irradiation treatment without pre-drying, and based on this knowledge, the present invention was accomplished. That is, according to the present invention, a neutral salt or a weakly basic salt of a metal selected from alkali metals or alkaline earth metals, an epoxy compound, a foaming agent, and optionally a dye are added to the protein fiber or its product. By impregnating the protein fiber with a foamy composition containing the protein fiber and directly subjecting it to microwave irradiation treatment, it is possible to efficiently modify the protein fiber or its products without sacrificing their advantages. In the method of the present invention, it is necessary to use neutral or weakly basic salts of alkali metals or alkaline earth metals as epoxidation catalysts, such as lithium, sodium, potassium, rubidium, and osmium. Water-soluble neutral salts or weak basic salts of alkali metals such as beryllium, magnesium, calcium, strontium, and alkaline earth metals such as barium, which have a pH of 1N aqueous solution within the range of 5.5 to 9.0. is desirable. Examples of the alkali metal salts include sodium fluoride, sodium chloride, sodium bromide, sodium nitrate, sodium sulfate, sodium acetate, sodium nitrite, sodium thiocyanate, sodium thiosulfate, and corresponding lithium salts, potassium salts, and osmium salts. Examples of salts of alkaline earth metals include barium thiocyanate, calcium thiocyanate, calcium iodide, barium chloride, calcium chloride, calcium iodide, strontium chloride, and magnesium chloride. These salts are usually used at a concentration of 0.1 to 3N. If the concentration is lower than this, the reaction promoting effect will be insufficient, and if the concentration is higher than this, there is a risk that the fibers will be partially dissolved due to microwave irradiation and fiber processing conditions. Generally, 0.1 for animal hair fibers such as wool and rabbit hair.
~0.5 normal, preferably in the range of 0.1 to 1.5 normal for silk fibers. Next, the epoxy compound used in the method of the present invention can be arbitrarily selected from those conventionally used for epoxidizing protein fibers. Such compounds include, for example, the general formula (However, R 1 , R 2 , R 3 and R 4 are hydrogen atoms or any organic residues that allow the compound of the formula to exist stably and do not interfere with the reaction with protein fibers, and are interconnected to form a ring. These organic residues include nitro groups, cyano groups, halogen groups, carboxyl groups, carbonyl groups, hydroxyl groups, amino groups, alkoxyl groups, epoxy groups, and substituted or Examples thereof include unsubstituted alkyl, alkenyl, alkynyl, aralkyl, aryl, alkoxy, aryloxy, allyl, and other groups. These compounds include, for example, propylene oxide, butadiene monoxide, styrene oxide, alkylene oxides such as vinylcyclohexane oxide, phenyl glycidyl ether, butyl glycidyl ether, diglycidyl ether of bisphenol A, triglycidyl ether of glycerin, etc. glycidyl ethers, glycidyl benzoate, glycidyl esters such as glycidyl methacrylate, esters and amides of epoxy acids such as ethyl 10,11-epoxyundecanoate, alkyl glycidyl urethanes, glycidyl methyl sulfonate and dimethyl alkyl 2, 3
- Sulfonic acid glycidyl esters and epoxysilanes such as epoxyalkyloxysilanes,
Includes epoxy alcohols such as glycidol, epoxy amines such as glycidylaniline, epoxy acids such as glycidylbenzoic acid, halogenated epoxides such as epichlorohydrin and epibromohydrin, and carbonyl epoxides such as glycidyl aldehyde. be done. These epoxy compounds can be used alone or in a mixture of two or more, but the number of epoxy groups in the epoxy compound molecule, reactivity, and interaction of the epoxy compounds should be taken into consideration, and the type of processed protein fiber and the type of processed protein fiber should be taken into consideration. It is important to select appropriate treatment conditions to suit the intended use and to determine appropriate reaction conditions. Such epoxy compounds can be used as they are, or may be dissolved in a suitable solvent. In other words, if it is water-soluble, it can be used as it is as an aqueous solution, but if it is water-insoluble, it can be dissolved in a mixed solvent of water and a water-soluble solvent such as methanol, ethanol, isopropanol, acetone, or dioxane.
Alternatively, it can be used by dissolving it in an appropriate non-aqueous solvent as an emulsified dispersion using an appropriate method. The amount of epoxy compound used varies depending on the type of protein fiber, tissue, etc., as well as the type of epoxy compound.
The amount is 2 to 30%, preferably 6 to 20%, based on the weight of the protein fiber. In addition, the treatment step in the present invention involves impregnating protein fibers with a foamy composition containing salt and an epoxy compound, compressing and defoaming, and washing after microwave irradiation treatment, but the microwave irradiation time is It also varies depending on the type and structure of the protein fiber, the intended use, the reactivity of the epoxy compound, and the type and amount of non-aqueous solvents and additives contained in the processing solution. Naturally, it also varies depending on the microwave output (normally usable ranges are 2450MHz to 25kw and 900MHz to 25kw) and heating methods (box oven, waveguide oven, etc.). , 10 seconds to 10 minutes,
Preferably it is 30 seconds to 5 minutes. In the treatment under such conditions, the catalyst is a neutral salt or a weakly basic salt, and the treatment is carried out for a single time, so that yellowing of the protein fibers does not occur. The foam processing method employed in the present invention, in which fibrous and other porous substrates are brought into contact with a small amount of foam-forming treatment liquid to obtain a uniform finished product, is well known; Presence 0.25:1-5: (weight)
This is a process in which the catalyst and epoxy compound are brought into contact with the fiber material at a treatment liquid to material ratio of , and the catalyst and epoxy compound are uniformly distributed throughout the fiber material. The ratio of treatment liquid to material is preferably 0.5:1 to 3:1 (by weight), more preferably 1:1 to 1.5:1 (by weight). The process is applicable to all types of porous, especially fibrous, woven materials that can be putted or dipped, such as loose filaments, yarns, knits, woven or tufted products, nonwovens, velvets, carpets and felts. . Foaming agents may be of the known type, i.e. anionic, cationic, amphoteric or non-ionic agents, but must be compatible with the epoxy compound used in the present invention, but should not be present during the process. Nonionic foaming agents are generally preferred since they must be active. The type of foaming agent used depends on the PH of the processing solution, the catalyst used, the epoxy compound, and if a dye is used in combination with the dye described below, whether there is compatibility or interaction with the dye or other additives. selected by. Foaming agents include partially carboxymethylated alkyl, aryl, alkylaryl or arylalkyl polyglycol ethers, alkanes, alkylbenzenes and alkylnaphthalene sulfonates, primary or secondary alkyl sulfates, alkyl polyglycols. , alkyl-
Anionic agents include phenyl polyglycol- and dialkyl phenyl polyglycol ether sulfates, sulfonated or sulfated oils, fatty acid taurides, and fatty acid sulfate ethylamide. Suitable nonionic foaming agents include water-soluble adducts prepared by reacting 8 to 50 moles of ethylene oxide with fatty alcohols, fatty acids, fatty acid amides, alkyl mercaptans or alkyl phenols. Cationic foaming agents such as adducts obtained by the reaction of 8 to 100 moles of ethylene oxide with aliphatic alkyl amines or aliphatic alkyl polyamides and their quaternized derivatives, fatty acid sulfate-ethylaminoethylamide, fatty acid γ-sulfonate There are amphoteric foaming agents such as -β-hydroxy-propylaminoethylamide. The foam composition used in the present invention contains, in addition to the catalyst salt, epoxy compound, foaming agent, water, and organic solvent,
If necessary, processing aids such as emulsifiers, glues, other salts, carriers, etc. may be added. Foamed compositions are usually obtained by commercially available foaming equipment using air or any inert gas. In other words, any device capable of mixing a generally metered amount of inert gas with a treatment liquid containing the treatment agent to be applied to the fibers and converting the mixture into a foam can be used. The composition used to produce the foam contains a foaming agent.
A catalyst salt having a concentration of 0.1 to 3N at a concentration of 0.2 to 5% by weight, preferably 0.4 to 2% by weight, an epoxy compound of 5 to 80% by weight, preferably 10 to 60% by weight, and an organic solvent of 1 to 3% by weight. 5% by weight, with water making up the remaining weight of the total composition. as an optional ingredient
A wetting agent of 0.001 to 2% by weight, preferably 0.01 to 1.0% by weight, can also be added, but if the blowing agent provides sufficient wetting action it is not necessary to add it at all. When using a foaming epoxy compound, the amount of foaming agent may be reduced or may not be added at all. Foam density is 0.005 to 0.3 per c.c.
g, preferably ranging from 0.01 to 0.2 g per c.c., and the average diameter of the bubbles from 0.05 to 0.2 g per c.c.
0.5 mm, preferably 0.08-0.45 mm. In this way, reacted with an epoxy compound,
The protein fibers are soaped, washed with water, and then dried according to conventional methods. Protein fibers treated by the method of the present invention have significantly improved alkali resistance, acid resistance, discoloration resistance, wrinkle resistance, and shrink resistance.
Furthermore, if the protein fibers are coated with an epoxide-containing treatment foam composition in which a dye capable of dyeing protein fibers is added at the same time as salts, and then subjected to microwave irradiation treatment, permanent modification of the protein fibers can be achieved. Other staining can also be carried out at the same time. Dyes that can be used include Procion-based dyes such as Procion Scarlet HR, Procion Blue H5RS, and Procion Brilliant Orange GS; Mikasion-based dyes such as Mikasion Scarlet 2G and Mikasion Red B; Remazol-based dyes such as Remazol Golden Yellow G; and Dia Mira Brilliant Red.
Examples include BB, Diamond Mira Brilliant Orange GGD, and other Diamond Mira products. Effects of the Invention According to the present invention, protein fibers are impregnated with a treatment liquid containing a reaction catalyst and an epoxy compound in the form of foam, and then subjected to microwave irradiation treatment without pre-drying, thereby reducing the amount of treatment liquid in a small amount. Since the modification process can be carried out efficiently using epoxy compounds and epoxy compounds, it is possible to largely prevent raw material loss, and it is also possible to save much more time and energy than conventional methods. EXAMPLES Next, the present invention will be explained in detail using examples. Example 1 10 parts by weight of vinyl cyclohexene dioxide, 20 parts by weight of dimerized linoleic acid diglycidylester, 10 parts by weight of phenyl glycidyl ether, 11 to 100 parts by weight of oxygen
1.3 parts by weight of a foaming agent consisting of a 20 mole adduct of ethylene oxide of a linear secondary alcohol having 15 carbon atoms, 5 parts by weight of n-octane, and a stabilizer consisting of a 9 mole adduct of ethylene oxide of a linear secondary alcohol having 11 to 15 carbon atoms.
0.5 parts by weight, 15 parts by weight of an emulsion containing low molecular weight polyethylene and a nonionic surfactant, and 0.2 parts by weight of a silicone wetting agent, so that the concentration was 1N.
The treatment solution to which the Na 2 S 2 O 3 aqueous solution was added was foamed in a commercially available Oakes type mixer. The foam composition was applied and impregnated using an applicator onto a scouring and bleached 16-momme silk habutae, and compressed to 150% impregnation. The treatment solution-impregnated fibers were sealed in a glass container without pre-drying, placed in a 2450MHz box oven, and subjected to microwave treatment at 600W for 3 minutes. It was washed with 80°C hot water containing a processing liquid detergent, rinsed with water, and dried.
The weight increase rate of the treated fabric is 13%, and the wrinkle resistance (in the warp direction) according to the Monsanto method is 71% when dry and when wet.
69%, which was a large increase compared to 59% and 55%, respectively, for untreated fabrics. In addition, one provision
The results of the alkaline solubility test with NaOH solution at 65℃ for 1 hour were 11% and 3% compared to 57% of the untreated sample.
The result of an acid solubility test using a normal HCl solution at 65°C for 1 hour was 6.4% compared to 48% for the untreated sample, which showed a significant improvement in chemical resistance. The shrinkage rate was 1.4% compared to 2.5% for untreated. Examples 2 to 13 Various salts (concentrations) were used instead of Na 2 S 2 O 3 in Example 1.
Types of salt used based on the weight increase rate and alkali resistance of silk fabrics treated in the same manner as in Example 1 using a foam composition having the same composition as in Example 1, in which 0.8N) was added as a catalyst. , Table 1 shows the results for the microwave processing conditions. All of these fabrics had the same whiteness and texture as the untreated fabrics, and were superior to the untreated fabrics in terms of not only alkali solubility but also acid solubility and wrinkle resistance.
【表】
実施例 14
2,2−ビス〔4−(2,3−エポキシプロポ
キシ)フエニル〕プロパン10重量部、レゾルシン
ジグリシジルエーテル30重量部、パークレン3重
量部、脂肪酸アミド系起泡剤1.5重量部、炭素数
11〜15の鎖状第二アルコールノエチレンオキシド
7モル付加物からなる湿潤安定剤0.6重量部の他
実施例1と同様な乳濁液、界面活性剤とからなる
処理液に、濃度0.4NになるようにKCl水溶液を添
加した組成物を実施例1と同様な市販の発泡機で
発泡させた。該泡状組成物を精練した羊毛フラン
ネルに塗布180%に圧搾含浸させ、予備乾燥する
ことなく、そのままガラス容器内に密閉、2450M
Hz導波管オーブンに入れ400Wで2分マイクロ波
処理した。処理後洗剤を含む60℃の熱水で洗浄、
水洗して乾燥した。処理布の風合、色調は未処理
布とほとんど変らず、重量増加は10%であつた。
処理布を0.1N NaOH水溶液65℃1時間処理した
時の重量減少率及び1N HCl溶液に1時間浸漬し
た時の重量減少率は共に0%であつた。また処理
布を石鹸による繰返し10回の洗濯後もその風合は
変化しなかつた。
実施例 15
エチレングリコールジグリシジルエーテル20重
量部、グリセリントリグリシジルエーテル10重量
部、トルエン3重量部の他に、実施例1と同様な
起泡剤、乳濁液、湿潤剤、安定剤を含む組成物に
0.3NになるようにNaSCN水溶液を添加した処理
液を実施例1と同様に発泡させた。該泡状組成物
を精練した兎毛に塗布150%に圧搾含浸させ、予
備乾燥することなくそのままガラス容器内に入れ
密閉、2450MHz導波管オーブンに入れ600Wで80
秒マイクロ波処理をした。処理後洗剤を含む60℃
の熱水で洗浄、水洗して乾燥した。処理繊維の風
合、色調は未処理布とほとんど変わらず重量増加
は11%であつた。処理繊維を0.1N NaOH水溶液
に65℃で1時間処理した時の重量減少率及び1N
HCl水溶液に1時間浸漬した時の重量減少率は共
に0%であつた。
実施例 16
エピクロルヒドリン5重量部、グリシドール5
重量部、フエニルグリシジルエーテル10重量部、
グリセリントリグリシジルエーテル10重量部、ト
ルエン2重量部、イプロパノール1重量部、
Mikacion Brilliant Blue RS1重量部の他に実施
例1と同様な起泡剤、安定剤、乳濁液とからなる
組成物に0.5NになるようにNaHCO3水溶液を加
えた処理液を実施例1と同様に発泡させた該泡状
組成物を精練した羊毛フランネルに塗布し160%
に圧搾含浸、そのまま密閉容器に入れ2450MHz導
波管オーブンに入れた。800Wで55秒マイクロ波
処理をした。処理後洗剤を含む60℃の熱水で洗
浄、水洗して乾燥した。処理織物は鮮明な青色に
染色されフエルト化は全く起らなかつた。処理繊
維の重量増加率は約8.3%であり、耐アルカリ、
耐酸性共に顕著に向上した。洗濯堅ろう度、変退
色ともに5級であり、未処理布に比較して非常に
すぐれていた。
実施例 17
ジグリシジルテレフタレート10重量部、フエニ
ルグリシジンエーテル20重量部、キシレン2重量
部ミツイブリリアントミリングレツドBL0.6重量
部の他に、実施例15と同様の起泡剤、実施例1と
同様の安定剤、乳濁剤、湿潤剤とからなる組成物
に0.3規定になるようにK2S2O3水溶液を加えた処
理液を発泡させて、精練した兎毛布に塗布、150
%に圧搾含浸した。予備乾燥せずそのまま2450M
Hz箱型オーブンに入れ、600Wで150秒マイクロ波
処理した。処理後沸騰アセトンで洗浄、石鹸水と
水でさらに洗浄後乾燥した。重量増加率9%、濃
色に均染された処理布が得られたが、洗濯堅ろう
度、変退色ともに5級で非常にすぐれた結果を示
した。
実施例 18〜24
エチレングリコールジグリシジルエーテル20重
量部、1,2−エポキシ−2,3−ジクロロプロ
パン5重量部、ビニルシクロヘキセンジオキシド
5重量部、イソプロパノール2重量部、0.7重量
部の種々染料を含む他、実施例1と同様な起泡
剤、安定剤、湿潤剤、0.3N KSCN水溶液とから
なる処理液を発泡させて、精練したタンパク繊維
に塗布150%に圧搾含浸させた。次いでそのまま
2450MHz導波管オーブンに入れ、600Wで90秒マ
イクロ波処理した。処理後実施例16と同様に処理
し乾燥した。結果を第2表にまとめた。処理絹繊
維の場合、モンサントしわ回復角は130〜140度、
収縮率1.5〜1.9%、アルカリ溶解度14〜19%、酸
溶解度10〜15%と未処理布のおのおの122度、2.5
%、53%、20%の値を比較して性質が著しく改善
された。また、処理羊毛布の耐アルカリ溶解度は
10〜12%と未処理布の29%と比較して著しく向上
した。[Table] Example 14 10 parts by weight of 2,2-bis[4-(2,3-epoxypropoxy)phenyl]propane, 30 parts by weight of resorcin diglycidyl ether, 3 parts by weight of percrene, 1.5 parts by weight of fatty acid amide foaming agent part, number of carbons
In addition to 0.6 parts by weight of a wetting stabilizer consisting of a 7-mol adduct of linear secondary alcohol noethylene oxide of 11 to 15, a treatment liquid consisting of the same emulsion and surfactant as in Example 1 was added to a treatment solution having a concentration of 0.4N. The composition to which the KCl aqueous solution was added was foamed using a commercially available foaming machine similar to that used in Example 1. The foam composition was applied to refined wool flannel and compressed to 180% impregnation, and sealed in a glass container as it was without pre-drying, 2450M
It was placed in a Hz waveguide oven and subjected to microwave treatment at 400W for 2 minutes. After treatment, wash with 60℃ hot water containing detergent.
Washed with water and dried. The texture and color tone of the treated fabric were almost the same as those of the untreated fabric, and the weight increase was 10%.
The weight loss rate when the treated cloth was treated with a 0.1N NaOH aqueous solution at 65° C. for 1 hour and the weight loss rate when it was immersed in a 1N HCl solution for 1 hour were both 0%. Furthermore, the texture of the treated fabric did not change even after repeated washing with soap 10 times. Example 15 Composition containing 20 parts by weight of ethylene glycol diglycidyl ether, 10 parts by weight of glycerin triglycidyl ether, 3 parts by weight of toluene, and the same foaming agent, emulsion, wetting agent, and stabilizer as in Example 1. to things
A treatment liquid to which an aqueous NaSCN solution was added to give a concentration of 0.3N was foamed in the same manner as in Example 1. The foam composition was applied to refined rabbit hair and compressed to 150% impregnation, placed in a glass container without pre-drying, sealed, and placed in a 2450 MHz waveguide oven at 600 W for 80 min.
Second microwave treatment. 60℃ including detergent after treatment
Washed with hot water, rinsed with water and dried. The texture and color tone of the treated fibers were almost the same as those of untreated fabrics, and the weight increase was 11%. Weight loss rate and 1N when treated fibers were treated with 0.1N NaOH aqueous solution at 65℃ for 1 hour
The weight loss rate when immersed in an HCl aqueous solution for 1 hour was 0% in both cases. Example 16 5 parts by weight of epichlorohydrin, 5 parts by weight of glycidol
parts by weight, phenyl glycidyl ether 10 parts by weight,
10 parts by weight of glycerin triglycidyl ether, 2 parts by weight of toluene, 1 part by weight of ipropanol,
In addition to 1 part by weight of Mikacion Brilliant Blue RS, a treatment solution in Example 1 was prepared by adding an aqueous solution of NaHCO 3 to 0.5N to a composition consisting of the same foaming agent, stabilizer, and emulsion as in Example 1. The same foamed composition was applied to scoured wool flannel to give a 160%
The sample was compressed and impregnated, then placed in a sealed container and placed in a 2450MHz waveguide oven. Microwave treatment was performed at 800W for 55 seconds. After treatment, it was washed with 60°C hot water containing detergent, rinsed with water, and dried. The treated fabric was dyed a bright blue color and no felting occurred. The weight increase rate of treated fibers is approximately 8.3%, and the alkali resistance and
Both acid resistance was significantly improved. The washing fastness and color change and fading were both grade 5, which was extremely superior to untreated fabric. Example 17 In addition to 10 parts by weight of diglycidyl terephthalate, 20 parts by weight of phenylglycidine ether, 2 parts by weight of xylene and 0.6 parts by weight of Mitsui Brilliant Milling Red BL, the same foaming agent as in Example 15, and Example 1 A treatment solution made by adding a K 2 S 2 O 3 aqueous solution to a composition of 0.3 normal to a composition consisting of a stabilizer, an emulsifying agent, and a wetting agent similar to the above was foamed and applied to a scoured rabbit blanket, 150
It was compressed and impregnated to %. 2450M without pre-drying
It was placed in a Hz box oven and microwaved at 600W for 150 seconds. After treatment, it was washed with boiling acetone, further washed with soapy water and water, and then dried. A treated cloth with a weight increase rate of 9% and a dark level dyeing was obtained, and both washing fastness and discoloration and fading showed very excellent results of grade 5. Examples 18-24 20 parts by weight of ethylene glycol diglycidyl ether, 5 parts by weight of 1,2-epoxy-2,3-dichloropropane, 5 parts by weight of vinylcyclohexene dioxide, 2 parts by weight of isopropanol, and 0.7 parts by weight of various dyes. In addition, a treatment liquid consisting of the same foaming agent, stabilizer, wetting agent, and 0.3N KSCN aqueous solution as in Example 1 was foamed, and the refined protein fiber was compressed and impregnated to 150% coverage. then continue as is
It was placed in a 2450MHz waveguide oven and subjected to microwave treatment at 600W for 90 seconds. After treatment, it was treated and dried in the same manner as in Example 16. The results are summarized in Table 2. For treated silk fibers, the Monsanto wrinkle recovery angle is 130-140 degrees;
Shrinkage rate 1.5~1.9%, alkaline solubility 14~19%, acid solubility 10~15% and 122 degrees, 2.5 respectively for untreated fabric.
%, 53%, and 20%, the properties were significantly improved. In addition, the alkali solubility resistance of treated wool fabric is
10-12%, a marked improvement compared to 29% for untreated fabric.
Claims (1)
又はアルカリ土類金属の中から選ばれた金属の中
性塩又は弱塩基性塩とエポキシ化合物と起泡剤と
を含む泡状組成物を含浸させ、そのままマイクロ
波照射処理することを特徴とするタンパク繊維又
はその製品の処理方法。 2 タンパク繊維又はその製品に、アルカリ金属
又はアルカリ土類金属の中から選ばれた金属の中
性塩又は弱塩基性塩と染料とエポキシ化合物と起
泡剤とを含む泡状組成物を含浸させ、そのままマ
イクロ波照射処理することを特徴とするタンパク
繊維又はその製品の処理方法。[Claims] 1. A foam composition containing a protein fiber or a product thereof, a neutral salt or a weakly basic salt of a metal selected from alkali metals or alkaline earth metals, an epoxy compound, and a foaming agent. A method for processing protein fibers or products thereof, which comprises impregnating the material and directly subjecting it to microwave irradiation treatment. 2. Impregnating protein fibers or products thereof with a foam composition containing a neutral salt or weakly basic salt of a metal selected from alkali metals or alkaline earth metals, a dye, an epoxy compound, and a foaming agent. , a method for processing protein fibers or products thereof, characterized by subjecting them to microwave irradiation treatment as they are.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11870284A JPS61682A (en) | 1984-06-08 | 1984-06-08 | Protein fiber and treatment of structure containing protein fiber |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11870284A JPS61682A (en) | 1984-06-08 | 1984-06-08 | Protein fiber and treatment of structure containing protein fiber |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61682A JPS61682A (en) | 1986-01-06 |
JPH0512474B2 true JPH0512474B2 (en) | 1993-02-18 |
Family
ID=14743023
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11870284A Granted JPS61682A (en) | 1984-06-08 | 1984-06-08 | Protein fiber and treatment of structure containing protein fiber |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61682A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63105177A (en) * | 1986-10-20 | 1988-05-10 | 万栄織物株式会社 | Method for processing silk fiber fabric |
JPS6420380A (en) * | 1987-07-14 | 1989-01-24 | Minoru Ban | Chemical processing of silk knitted fabric |
JPS6420379A (en) * | 1987-07-14 | 1989-01-24 | Minoru Ban | Chemical modification of silk fiber product |
DE19648855A1 (en) * | 1996-11-26 | 1998-05-28 | Alchimea Naturwaren Gmbh | Process for finishing keratin fibers and cellulose |
CN102293453B (en) * | 2011-08-05 | 2013-08-14 | 赤峰昭乌达羊绒制品有限责任公司 | Processing method for original cashmere sweater |
-
1984
- 1984-06-08 JP JP11870284A patent/JPS61682A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS61682A (en) | 1986-01-06 |
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