JPH0160110B2 - - Google Patents
Info
- Publication number
- JPH0160110B2 JPH0160110B2 JP57079262A JP7926282A JPH0160110B2 JP H0160110 B2 JPH0160110 B2 JP H0160110B2 JP 57079262 A JP57079262 A JP 57079262A JP 7926282 A JP7926282 A JP 7926282A JP H0160110 B2 JPH0160110 B2 JP H0160110B2
- Authority
- JP
- Japan
- Prior art keywords
- component
- post
- dcda
- treatment agent
- formaldehyde
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 92
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 23
- 239000007795 chemical reaction product Substances 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 19
- 229920000742 Cotton Polymers 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000004043 dyeing Methods 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 16
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 13
- 239000004202 carbamide Substances 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 13
- 238000004132 cross linking Methods 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000000982 direct dye Substances 0.000 claims description 7
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 claims description 5
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 5
- 229920000768 polyamine Polymers 0.000 claims description 5
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920001281 polyalkylene Polymers 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 238000013007 heat curing Methods 0.000 claims description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 3
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 3
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 2
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims 1
- 239000012932 acetate dye Substances 0.000 claims 1
- 238000005282 brightening Methods 0.000 claims 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000005406 washing Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 239000000985 reactive dye Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000009967 direct dyeing Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 229920003043 Cellulose fiber Polymers 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000008098 formaldehyde solution Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- -1 urea compound Chemical class 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229960002337 magnesium chloride Drugs 0.000 description 3
- 229940091250 magnesium supplement Drugs 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010016 exhaust dyeing Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- PMZIUAOBHNJYQT-UHFFFAOYSA-N (1-hydroxy-2-methylpropan-2-yl)azanium;chloride Chemical compound Cl.CC(C)(N)CO PMZIUAOBHNJYQT-UHFFFAOYSA-N 0.000 description 1
- IQDKUTQPYBHPJK-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)-1,3-diazinan-2-one Chemical compound OCN1CCCN(CO)C1=O IQDKUTQPYBHPJK-UHFFFAOYSA-N 0.000 description 1
- XKALZGSIEJZJCZ-UHFFFAOYSA-N 1,3-bis(methoxymethyl)urea Chemical compound COCNC(=O)NCOC XKALZGSIEJZJCZ-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- ZVXPZLNAJOMRPK-UHFFFAOYSA-N 2-(hydroxymethyl)prop-1-ene-1,3-diol;urea Chemical compound NC(N)=O.OCC(CO)=CO ZVXPZLNAJOMRPK-UHFFFAOYSA-N 0.000 description 1
- KFVIYKFKUYBKTP-UHFFFAOYSA-N 2-n-(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCNC1=NC(N)=NC(N)=N1 KFVIYKFKUYBKTP-UHFFFAOYSA-N 0.000 description 1
- UWOFGIXNNCPENM-UHFFFAOYSA-N 3,3-difluoropentan-2-one Chemical compound CCC(F)(F)C(C)=O UWOFGIXNNCPENM-UHFFFAOYSA-N 0.000 description 1
- STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- YIQKLZYTHXTDDT-UHFFFAOYSA-H Sirius red F3B Chemical compound C1=CC(=CC=C1N=NC2=CC(=C(C=C2)N=NC3=C(C=C4C=C(C=CC4=C3[O-])NC(=O)NC5=CC6=CC(=C(C(=C6C=C5)[O-])N=NC7=C(C=C(C=C7)N=NC8=CC=C(C=C8)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+] YIQKLZYTHXTDDT-UHFFFAOYSA-H 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000001153 anti-wrinkle effect Effects 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical group CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical class [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- QTTDXDAWQMDLOF-UHFFFAOYSA-J tetrasodium 3-[[4-[[4-[(6-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-6-sulfonatonaphthalen-1-yl]diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].Nc1ccc2c(O)c(N=Nc3ccc(N=Nc4ccc(N=Nc5cc(c6cccc(c6c5)S([O-])(=O)=O)S([O-])(=O)=O)c5ccccc45)c4ccc(cc34)S([O-])(=O)=O)c(cc2c1)S([O-])(=O)=O QTTDXDAWQMDLOF-UHFFFAOYSA-J 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Landscapes
- Coloring (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
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This invention relates to post-treatment methods for improving the fastness properties of dyes and optical brighteners on hydroxy group-containing substrates. The present invention provides a method for improving the fastness properties of dyes or optical brighteners on substrates containing hydroxy group-containing fibers, the method comprising: (A) the reaction product of a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide (DCDA), guanidine or biguanidine, or the reaction product of ammonia with cyanamide or DCDA; , cyanamide, DCDA, reaction products in which up to 50 mol % of guanidine or biguanidine may be replaced by dicarboxylic acids or mono- or diesters thereof, and which contain reactive hydrogen atoms bonded to nitrogen, and (B) epihalohydrins. or a precursor thereof, or (C) formaldehyde or a formaldehyde precursor, or (D) a dihydroxyalkylene urea or its methyl ether, then a precondensate of formaldehyde or a formaldehyde precursor, if desired (F) urea, melamine,
with N-methylol derivatives of guanamine, triazinones, uron, carbamates or acid amides, and when (A) is used in conjunction with (C) or (D) or when (E) is present, (F) ) is characterized in that it is applied together with a catalyst for crosslinking of N-methylol compounds of the type and then carrying out the crosslinking step. In the process of the invention, the presence of N-methylol compounds (E) which provide an additional anti-wrinkle finish is optional. However, the presence of catalyst (F) causes components (A) and (B) to
is required except when the precondensation product of (E) is used without the intervention of (E). The term "precondensate" refers to a reaction product that is water-soluble, ungelled, and capable of further crosslinking. The present invention further provides a post-treatment agent for substrates containing dyed, printed or brightened hydroxy group-containing fibers, which agent comprises component (A) and component (B), (C) or ( D) together with catalyst (F) and optionally component (E). The catalyst is preferably added to the precondensate already formed, or the condensation reaction may optionally be carried out in the presence of a catalyst. If the N-methylol compound (E) is present, it can be combined with (A) already formed with the catalyst (F), (B), (C) or
(D) may be mixed with the initial condensate, or
The mixtures of (A) and (B), (C) or (D) and (E) may be reacted together and the catalyst added before, during or after this reaction. The reaction products of (A) and (B) or (C) and (E) also form part of the invention. For use with components (B) and (C), component (A) is preferably the reaction product of a polyalkylene polyamine with cyanamide, dicyanamide (DCDA) or guanidine, more preferably DCDA. The polyamine preferably has the following formula. RRN ( -- Z-- , n represents a number from 0 to 100, and Z
each independently represents C 2-4 alkylene or hydroxyalkylene, and each X independently represents -O
--, --S-, or --NR- (where R represents the same thing as in the above definition). However, the amine of this formula has at least one reactive -NH-
or - shall contain NH 2 groups. More preferably each R is hydrogen, n is 0-4, X is -NH- or -NCH3- , and each Z is C2-4 alkylene. Particularly preferred compounds are diethylenetriamine, triethylenetetramine, tetraethylenepentamine,
2-aminoethyl-3-aminopropylamine,
Dipropylenetriamine and N,N-bis-(3
-aminopropyl) methylamine. For use with component (D), the same type of preferred component (A) is used. But other types are cyanamide, DCDA or guanidine, preferably
It is a reaction product of DCDA and an amine of the following formula. RRNH In the above formula, R represents the same thing as defined above. Component (A) is known, for example British patent 657753,
US Patent 2649354 and UK Patent Application Publication 2070006A
It can be prepared by the method described in .
The amine, in dilute base or salt form, is suitably reacted with other starting materials without the intervention of water, at elevated temperature, optionally in the presence of a non-aqueous solvent. Preferably the reaction is carried out without solvent intervention.
It is carried out at temperatures of 140-160°C and ammonia is liberated for most combinations of reagents. The reagent preferably contains 0.1 to 1 mole of cyanamide per mole of reactive -NH- or -NH2 groups,
The molar ratio of the reagents is more preferably from 2:1 to 1:2, especially about 1:1 when DCDA is reacted with a polyalkylene polyamine. The product (A) is basic, water-soluble in free base or salt form, and is an almost colorless viscous liquid or solid containing a reactive hydrogen atom bonded to a nitrogen atom. Up to 50 mol%, preferably up to 20 mol%, of the DCDA or other reagent to be reacted with the amine may be replaced by dicarboxylic acid or itself or diester. Suitable acids include adipic acid, oxalic acid and terephthalic acid, for example in the form of dimethyl ester. Component (A) and epihalohydrin or its precursor (B)
The reaction with is preferably carried out in an aqueous solution or dispersion at a temperature of room temperature to 100°C, preferably 40 to 80°C. Preferred reagents are epichlorohydrin and dichlorohydrin, ClCH2 .
CHOH·CH 2 Cl, more preferably epichlorohydrin. The molar ratio of component (A) to epihalohydrin is preferably such that the molar ratio of component (A) to epihalohydrin is
or based on the number of moles of similar compounds, 1:
The ratio is 0.3 to 2, more preferably 1:0.5 to 1.5. The reaction should not proceed to the point where gel formation begins. Preferably, the initial PH of the reaction mixture is adjusted to between 6 and 9 by addition of acid, and the reaction products of (A) and (B) under these PH conditions are novel and form part of the present invention. do. The reaction between component (A) and formaldehyde or its precursor (e.g. paraformaldehyde) (C) is preferably carried out in an aqueous medium at 20-60°C, preferably at 40-50°C.
temperature in °C and PH greater than 4, preferably 7-11
It will be carried out at the PH of Formaldehyde may be added in the form of a concentrated (eg 37%) aqueous solution. The preferred molar ratio of component (A) to formaldehyde is in the range 1:2 to 1:6 relative to the number of moles of amine originally present. The reaction of component (A) with dihydroxyalkylene urea and subsequently with formaldehyde (D) can also be carried out in an aqueous medium, for example by preparing a concentrated aqueous solution of dihydroxyalkylene urea in a greenhouse or at a temperature of 80°C, preferably 60-75°C. It is suitably carried out by adding it to an aqueous solution of A). A preferred reagent is dihydroxyethylene urea or its methyl ether. The reaction of this intermediate with formaldehyde is carried out under acidic conditions, it being advantageous to acidify the reaction mixture even before carrying out the reaction of (A) with the hydroxyalkylene urea compound. Component (A) dihydroxyalkylene urea (DH)
and formaldehyde (FM)) is preferably in the range of 5 to 40 parts of (A), 25 to 110 parts of DH, and 1 to 60 parts of FM, which is (A):DH:FM
= corresponds to a weight ratio in the range of 1:0.625 to 22:0.025 to 12. The preferred ratio is (A) 10-20 parts, DH20-25
part, FM5-30 part, or A:DH:FM=1:1
~2.5: 0.25~3. All these calculations are based on the dry weight of the active ingredient. 1 to 10% (wt% based on the sum of (A) + (D)) cyanamide or dicyandiamide (DCDA),
It has been found that a more stable product is obtained if DCDA is preferably added to the reaction mixture, preferably before the reaction takes place. Suitable catalysts (F) include nitrates, sulfates, chlorides, tetrafluoroborates and dihydrogen orthophosphates of aluminum, magnesium and zinc, as well as aluminum oxychloride, zirconyl oxychloride and mixtures of any of these. These catalysts may also be used in the form of mixtures with water-soluble inorganic salts, in particular alkali metal sulfates or alkaline earth metal salts, preferably chlorides. Particularly preferred are sodium or potassium sulfate and calcium chloride. These may also be used in mixtures with organic acids such as citric acid. Other suitable catalysts are (a) bisulfites of alkali metals, (b) hydrochlorides of amines, such as 2-amino-2-methylpropanol hydrochloride, (c) organic acids, such as citric acid, oxalic acid, maleic acid. acids, glycolic acid and trichloroacetic acid, (d) inorganic acids such as phosphoric acid and hydrochloric acid, alone or with salts such as ammonium chloride or calcium chloride, and (e) ammonium salts of inorganic acids such as nitric acid, chloride, sulfuric acid and ammonium oxalate, and mono- and diammonium orthophosphates. Mixtures of any of these catalysts can also be used. Preferred catalysts are nitrates, sulphates, chlorides and dihydrogen orthophosphates of aluminum, magnesium or zinc, more preferably magnesium, especially magnesium chloride, optionally used with alkali metal sulphates, especially sodium sulphate. It is. When an N-methylol compound (E) is present, suitable compounds are N-methylol compounds, such as those commonly known as crosslinking agents for cellulose fibers and used to impart wrinkle-resistant finishes to cellulose fibers. These compounds may contain free N-methylol groups, N-CH 2 OH, or they may be etherified. Preferred ether radicals are lower alkyl ethers having 1 to 4 carbon atoms in the alkyl group. Examples of suitable N-methylol compounds are N,Nâ²-
Dimethylol urea, N,N'-dimethylol urea dimethyl ether, N,N'-tetramethylol acetylene diurea, N,N'-dimethylol propylene urea, 4,5-dihydroxy-N,N'-
Dimethylolethylene urea, 4,5-dihydroxy-N,N'-dimethylolethyleneurea dimethyl ether, N,N'-dimethylol-5-hydroxypropylene urea, N,N'-dimethylol-4-methoxy-5,5- Dimethylpropylene urea, N,N'-dimethylolethylene urea, methoxymethylmelamine, dimethylolalkanediol diurethane, N,N'-dimethylol-5-
They are alkylhexahydro-1,3,5-triazin-2one, N,N'-dimethyloluron and dimethylol carbamate. These compounds may be used alone or as a mixture. Particularly suitable are hydrolysis-resistant reactive resin precursors, such as N,N'-dimethylol-4,5-
Dihydroxy- or -4,5-dimethoxy-
ethylene urea, N,N'-dimethylol-4-dimethoxy-5,5-dimethylpropylene urea and N,N'-dimethylol carbamate (optionally in etherified form). Preferred ether forms are methyl and ethyl ether derivatives. If the N-methylol compound (E) is present, it is the precondensate of (A) with (B), (C) or (D) and the catalyst (F).
It may be added to a post-treatment agent containing. Although the initial condensate of (A) and epihalohydrin (B) may be used as a post-treatment agent without a catalyst, N-methylol compounds
When (E) is added, the presence of a catalyst is required. Alternatively, the N-methylol compound (E), especially together with components (B) and (C), may be added to the mixture of (A) and (B) or (C) before the reaction takes place. In this case it is preferred that the catalyst (F) is also present in the reaction mixture. This forms an initial condensate of (A), (B) and (E) or (A), (C) and (E). The reaction conditions when (E) is present are the same as those when (E) is absent. The amount of (E) used is preferably 0 to 500% of the weight of (A) plus (B), (C) or (D), more preferably 0 or 50 to 200% of this weight. When (E) is present, the amount of catalyst (F) used is generally about 7.5-12.5% by weight of the dry weight of (E). The hydroxy group-containing substrate is preferably a cellulosic fiber substrate comprising natural or regenerated cellulose, especially cotton and viscose rayon, alone or mixed with synthetic fibers. The substrate may be dyed, printed or whitened in the usual manner, for example dyeing or whitening by exhaustion or by padding followed by heat fixation or cold hold fixation or, in the case of reactive dyes, by alkaline dyeing. It may also be implemented by fixation. The process according to the invention is particularly suitable for reactive and direct dyes, of which metal complex direct dyes, especially copper complex dyes, are preferred. The process according to the invention is carried out on a substrate that has undergone a dyeing or printing process including the necessary fixing steps. The substrate may be dry or wet as long as it is not so wet that it cannot be further picked up. Post-treatment agents can be applied in long or short bath exhaustion processes or by soaking, spraying,
It is applied to the substrate in an aqueous solution by foam application, padding or other conventional application techniques. The preferred method of application is padding at room temperature. In the exhaustion process, long bath ratio (10:1 or more)
is used, the concentration of the post-treatment agent (including compound (E) if present) in the bath is preferably between 1 and
10 g/, more preferably 2 to 5 g/, whereas if short baths are used amounts of up to 20 g/ or even up to 100 g/ are required.
(All weights are based on dry weight of active ingredient) Application by exhaustion does not contain ingredients (E) and (F) (A) and (B)
preferred for the initial condensate of In the case of application by padding, the amount of product according to the invention applied to the substrate depends largely on the concentration of the dye to be fixed. For 1/1 standard strength direct dyeings on cotton, the usage amounts are 30 to 200 g per padding solution when applied in a pick-up of 70 to 100% of the dry weight of the product.
Preferably, this amount is between 70 and 140 g/ for cotton and between 100 and 200 g for regenerated cellulose in order to improve wash resistance in wet fastness and obtain sufficient wrinkle resistance. / is.
In the case of application to mixtures of cellulose and synthetic fibers, the amount to be applied is calculated based on the cellulose content of the substrate. The padding fluid may further contain auxiliary agents such as stiffening agents, softeners, friction or cut strength improving agents, antifouling agents, hydrophobizing agents, etc., which when mixed with the product according to the invention form a stable aqueous solution. may be included as long as it can form. If the post-treatment agent contains N-methylol groups, as is the case for precondensates of (A) with (C) or (D), or in systems where (E) is present, the crosslinking is catalyzed by F) is carried out by a heat curing process in the presence of F). System (A)
For +(B), epoxy or chlorohydrin groups are present and crosslinking occurs under alkaline conditions and at lower temperatures. For the first type of system, the substrate is subjected to a heat curing process as usual for resin treatments based on compounds of type (E). For example, the base material is 70~
Dry at 120°C, then 2 times at a temperature of 130-180°C
Crosslinked for ~8 minutes. or at 100-200°C, preferably 140-180°C for 5 seconds to 8 seconds depending on this temperature.
Simultaneous drying and crosslinking may be carried out by heat treatment for minutes. A preferred process involves heating the padded substrate to 170-180°C for 30 seconds to 1 minute. For systems of the second type, crosslinking takes place during exhaustion application from an alkaline bath, for example at temperatures from room temperature to 100°C, preferably from 40 to 60°C. Particularly suitable direct dyes for use in the process of the invention are as follows. CI Direct Red 80, 83, 84, 92, 95, 207,
211, 218 CI Direct Yellow 39, 50, 98, 106, 129, CI Direct Violet 47, 66, 95, CI Direct Blue 71, 77, 79, 80, 85, 90,
94, 98, 217, 251, CI Direct Green 27, 31, 65, 67, CI Direct Brown 103, 111, 113, 116,
220, and CI Direct Black 62, 117, 118. Also particularly suitable reactive dyes are: CI Reactive Violet 23, CI Reactive Blue 23, and CI Reactive Blue 79. Dyeings and prints with direct dyes often exhibit insufficient washing fastness. Dyes adhering to the surface of cellulosic fibers may be shed in large quantities from the fibers by repeated washing, and dye leaching into the washing liquor may be partially readsorbed onto the undyed cellulosic material. In order to overcome these disadvantages, it is possible, for example, to complex the fibers with metal salts, to form dyes on the fibers, to treat the dyes and/or the fibers with formaldehyde, to impregnate them with synthetic resins, and to form dyes with cationic auxiliaries. Many attempts have been made to perform processing by post-processing. It is particularly effective to use cationic post-treatment aids. However, the drawback of all these conventional methods is that, although improvements in fastness are indeed obtained, their results are only temporary. Even in the case of cationic post-treatment agents, the auxiliaries are shed from the fibers, especially after repeated washing under alkaline conditions and at high temperatures such as 50-100°C. Shedding of the cationic auxiliaries means that the dyeings again lose their improved wet fastness properties. It was desired to overcome the wet fastness problem through the use of reactive dyes that form chemical bonds to the fibers. However, the disadvantage of using reactive dyes is that although dyes that are chemically bound to the fibers have excellent wash fastness, the product retains residual unfixed dyes after washing which makes wash fastness inadequate. This means that it must be thoroughly cleaned to remove it. The treatment of dyed cellulose substrates according to the present invention provides improved wet fastness properties, especially from 40 to 90°C.
It provides fastness to washing, including washing under alkaline conditions, especially at temperatures of 60° C. and above. For example, it easily withstands repeated washing at 60° C. for 30 minutes in a 1:50 bath ratio with a washing liquid containing 5 g/ml soap and 2 g/soda. In the case of dyeings with reactive dyes, the wash fastness of the unfixed dyes is improved to a level that is approximately the same as that of the fixed dyes, thereby eliminating the need for removal of the unfixed dyes. At the same time, the cellulose fibers are given a resin finish, which reduces their swellability in aqueous or alkaline media, thereby allowing faster drying,
It also provides improved dimensional stability and higher wrinkle resistance. The following examples are provided to further illustrate the invention, in which all "parts" and "%" are given by weight, and all temperatures are given in degrees Celsius. Example 1 103 parts of diethylenetriamine and 84 parts of
DCDA was heated to 110°. At this temperature an exothermic reaction started and ammonia was evolved. temperature
The reaction was completed by ramping to 150° and then holding at 160° for 6 hours. Finally, the reaction mixture was cooled to 90° and treated with 193 parts of water. The resulting suspension was cooled to room temperature, and the pH was adjusted to 7.5 by adding 59 parts of 96% sulfuric acid while cooling. 100 parts of this solution was further diluted with 425 parts of water, and 15.5 parts of epichlorohydrin were slowly added while cooling at room temperature. The reaction mixture was then heated to 50°,
Stirred at this temperature for 1 hour. The solution was cooled to room temperature and neutralized with 1 volume part of 30% caustic soda.
A clear, bright yellow solution was obtained, which could be used as a post-treatment agent for direct dyeings on cotton. Examples 2-7 Example 1 was repeated using the amounts of reagents (parts by weight) shown in Table 1.
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DCDA and 9.7 parts of dimethyl terephthalate were heated to 110°C and then slowly heated to 160°. 2.6 parts of methanol and 28.9 parts of ammonia were liberated within 3 hours. When the reaction is complete,
Cool the mixture to 90° and add 121.6 parts of 30% hydrochloric acid and 8.2 parts of
of water was added. A white suspension was obtained, which was cooled to room temperature. Dilute 65.9 parts of this suspension with 197.7 parts of water, add 17.3 parts of epichlorohydrin to 25 parts of
Added dropwise at ~30°. Warm the mixture to 65-70°,
Stir for hours. The resulting solution has a pH of 5.2,
Neutralized to pH 7 with 4.5 parts of 30% caustic soda. Example 9 189 parts of tetraethylenepentamine is mixed with 84 parts of
It was reacted with DCDA at 150° for 5 hours. When no more ammonia evolved, a bright yellow condensation product was obtained, which solidified on cooling and was ground to a powder. 25 parts of this powdered condensation product were dissolved in 200 parts of water and added with 35% hydrochloric acid under cooling.
Adjusted to PH9. 8 parts of epichlorohydrin were added slowly at room temperature and the mixture was stirred at 70° for 3 hours. This was cooled to give a clear yellow solution. Example 10 Add 51.5 parts of diethylenetriamine to 90 parts of guanidine carbonate until no more gas is evolved.
The reaction was carried out at 160° for 6 hours. An orange-beige product was obtained, which was powdered at room temperature. Reaction with 7.5 parts of epichlorohydrin as described in Example 9 gave a clear yellow solution. Example 11 175.5 parts of 2-aminoethyl-3-aminopropylamine were reacted with 84 parts of DCDA at 120° for 6 hours. The condensation product obtained was diluted with 227 parts of water, and 50 parts of the resulting suspension were neutralized with 11.5 parts of 96% sulfuric acid and then reacted according to Example 1 with 10 parts of epichlorohydrin. Example 12 120 parts of ethylenediamine and 84 parts of DCDA
Condensation was carried out at 125° for 6 hours. The resulting condensation product
Dilute with 170 parts of water and add 50 parts of the resulting suspension to 14.8
1 part 96% sulfuric acid and then reacted according to Example 1 with 8 parts epichlorohydrin. Example 13 Application by exhaustion Exhaust dyeing with dye CI Direct Black 117 on cotton (1/1 standard concentration) was washed with water. Next, add 2 ml of 36° BeⲠcaustic soda and 2 g of dyed product.
In the liquid containing the post-treatment agent of Example 1 (based on total weight),
Processed for 1 hour at 40-50° at a bath ratio of 20:1. After a final wash in cold water and drying, the dyeing obtained had good wash fastness. Example 14 Application by padding A sample dyed with the dye CI Direct Violet 66 in an exhaust bath is padded with a solution containing 40 g/(based on dry weight) of example 1 aftertreatment agent and 5 g/soda, approx. I narrowed it down to 80% pick-up. The fabric was then dried on a tenter with hot air at 150° for 4 minutes, and then washed with water. The dyeing obtained had good washing fastness. Example 15 Application by padding with components (E) and (F) 1/1 standard density dyeing of CI Direct Blue 90 on cotton, 100 g of the after-treatment agent of Example 1, 50 g of dimethylol dihydroxyethylene urea and 7.5 g
was padded with a solution containing magnesium chloride hexahydrate and reduced to about 80% pick-up. The fabric is then brought to a temperature of 175-180° such that the condensation time of the dry fabric at this temperature is about 30-45 seconds.
Shock dried on a tenter. The treated dyeings had a high washing fastness, which was retained even after repeated washing at 60°. At the same time, there was a clear improvement in wrinkle resistance, and the swelling properties of cellulose fibers were reduced. Good results were obtained by applying the post-treatment agents of Examples 2-12 in the same manner as described in Examples 13-15. Example 16 103 parts of diethylenetriamine and 84 parts of
DCDA was reacted as described in Example 1. Although the reaction product was not treated with water and acid,
It was solidified by cooling. The resulting solid was then finely ground. 156 parts of this powder were suspended in 400 parts by volume of water and the mixture was heated to 80-90°, the powder gradually dissolved to give a solution with a pH of about 11. After cooling to 50°, 343 parts of a 35% aqueous formaldehyde solution were added dropwise. The reaction mixture was stirred for a further 2 hours at 50°, then cooled to room temperature and neutralized with hydrochloric acid to give 930 parts of a clear yellow solution containing about 30% by dry weight of the precondensate of diethylenetriamine/DCDA and formaldehyde. This could be used as a post-treatment agent for direct dyeings on cotton after addition of magnesium chloride. Example 17 Amine/DCDA before addition of formaldehyde
Example 16 was repeated except that the PH of the condensate solution was adjusted to PH 8 by dropwise addition of concentrated sulfuric acid. The precondensate obtained gave a post-treatment agent which, after addition of magnesium chloride, gave excellent washfastness properties to direct dyeings on cotton. Examples 18 and 19 PH from 6 to 6 respectively before addition of formaldehyde
Example 17 was repeated, but adjusted to 4. Examples 20 and 21 103 parts of diethylenetriamine are mixed with 105 parts of
It was reacted with DCDA under the conditions of Example 1. The reaction product was cooled and finely ground to give a yellow-beige powder (170 parts). Two lots of 90 parts each of this powder, one of 227 parts
35% formaldehyde solution and 340 parts of the other 35
% formaldehyde solution as described in Example 17. Finally, 10% of the obtained initial condensate
Diluted to the concentration of active material. Examples 22 to 33 Samples of cotton fabric were dyed with the dyes shown in Table 2.
1 standard concentration, washed with water, and dried. The dried sample was padded in an 80% pick-up with a solution containing xg/ml of the precondensate of Example 17, 50g/ml dimethylolhydroxyethylene urea and 15g/ml MgCl 2 6H 2 O and brought to pH 4 with acetic acid. It was adjusted. The padded substrate was shot dried on a tenter at 180°. The condensation time of the dried fabric was about 30-45 seconds. All fixed dyes had good wash fastness properties.
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䟡ãããçµæãäžèšã«ç€ºããTable Example 34 A 1/1 standard density dyeing on cotton with the reactive dye CI Reactive Violet 23 was produced according to the standard method without final washing. Rinse the dyed item briefly with cold water, dry and then add 70g/Example 17
(based on dry weight) and 15 g/
of MgCl 2 .6H 2 O in an 80% pick-up. The fabric was then dried to a residual moisture content of 2-4% and cured at 180° for 60 seconds. The dyeings obtained had good washfastness properties, even when the usual washing at the boil after dyeing was deliberately omitted. Example 35 19.4 parts of ammonium chloride were suspended in 19 parts of water and treated with 32 parts of DCDA. The mixture was heated to 70° and 15.2 parts of 30% hydrochloric acid was vaporized. The reaction mixture was warmed to 60° and stirred at this temperature for 45 minutes.
An initially clear solution was obtained, which then became cloudy. The mixture is then cooled to 60° and at this temperature 56.5
of dihydroxyethylene urea. The resulting suspension was stirred at 60° for 45 minutes,
Then, at the same temperature, 137.5 parts of a 37% aqueous formaldehyde solution were added dropwise. The resulting solution was cooled to 30° and adjusted to pH by adding about 12 parts of sodium acetate.
was adjusted to 3-3.5. Finally, 33.4 parts of MgCl2 .
6H 2 O was added dropwise and the mixture was stirred for 30 minutes at room temperature, yielding 235 parts of a clear yellow solution, which could be used as a post-treatment agent for direct dyeings on cotton. Example 36 DCDA and triethylenetetramine 1:1
60 parts of the condensation product in a molar ratio of was suspended in 40 parts of water, the pH was adjusted to 4 with 50 parts by volume of 35% hydrochloric acid, and the mixture was heated to 70°. At this temperature, 66 parts of dihydroxyethyleneurea were added in portions and the mixture was stirred for 1 hour. Furthermore, at the same temperature, 92 parts of
A 37% formaldehyde solution was added dropwise and the mixture was stirred for an additional hour. The product was cooled to room temperature and heated to approx.
of sodium acetate was added to adjust the pH to 3.0-3.5. Dissolving 30 parts of MgCl 2 6H 2 O in this solution gives 352 parts of a clear light brown solution,
It could be used as a post-treatment agent for direct dye dyeings on cotton. Examples 37 and 38 Example 15 was repeated using the products of Examples 35 and 36 in place of the product of Example 1. Good washing fastness properties were obtained. Example 39 Comparative Test The following products were used. (α) Reaction product of dicyandiamide (DCDA) and diethylenetriamine as described in the first paragraph of Example 1. (β) A reaction product of the product (α) above described in Example 1 and epichlorohydrin. The dyeing obtained by exhaust dyeing cotton jersey at 2.5% with CI Direct Blue 251 or CI Direct Red 261 was post-treated as described in Example 13 to improve the wash fastness and alkaline sweat fastness of the dyeing. The strength was tested as follows. Washing fastness: According to Swiss standard SNV195813 (60â, 30 minutes)
Cotton was used as the attached material. Alkaline sweat fastness Tested according to Swiss standard SNV195824 using cotton as the attachment material. Contamination of attached materials was evaluated using gray scale. The results are shown below.
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æäžã®æ±æãè©äŸ¡ãããçµæãäžèšã«ç€ºãã[Table] As is clear from the above, the fastness of the dyed articles post-treated with the product (β) was significantly improved. Example 40 Comparative Test The following products were used. (γ) Dimethyloldihydroxyethyleneurea. (ÎŽ) Reaction product of DCDA, diethylenetriamine and formaldehyde as described in Example 17. Using the product of
It was applied to a cotton fabric pre-dyed with Direct Yellow 98. Next, a washing fastness test was conducted according to Swiss standard SNV195814 (95°C, 30 minutes) using cotton as the attached material. Gray scale was used to assess contamination on attached materials. The results are shown below.
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ãããšããããã[Table] From the above, dyed products post-treated with product (ÎŽ) with or without product (γ) are different from dyed products post-treated with product (γ). It can be seen that the comparison shows significantly improved fastness.
Claims (1)
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ãããã«èšèŒã®åŸåŠçå€ã[Scope of Claims] 1. A method for improving the fastness properties of dyes or optical brighteners on substrates containing hydroxy group-containing fibers, which method comprises: dyeing, printing or brightening the substrate; (A) A reaction product of a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide (DCDA), guanidine or biguanidine, or a reaction product of ammonia with cyanamide or DCDA, wherein cyanamide, up to 50 mol% of the DCDA, guanidine or biguanidine may be replaced by a dicarboxylic acid or its mono- or diester, and (B) an epihalohydrin or its precursor, or (C) formaldehyde or formaldehyde precursor, or (D) dihydroxyalkylene urea or its methyl ether, and then formaldehyde or formaldehyde precursor, if desired, with (E) urea, melamine, with N-methylol derivatives of guanamine, triazinones, uron, carbamates or acid amides, and when (A) is used in conjunction with (C) or (D) or when (E) is present, (F) ) type N-methylol compounds together with a catalyst for crosslinking, and then carrying out a crosslinking step. 2. The method according to claim 1, wherein component (A) is a reaction product of DCDA with a mono- or polyfunctional primary or secondary amine or ammonia. 3. The method according to claim 1 or 2, wherein the amine in component (A) is a polyalkylene polyamine. 4. The method according to any one of claims 1 to 3, wherein component (A) is a reaction product of DCDA and a polyalkylene polyamine represented by the following formula. RRN ( -- Z-- , n represents a number from 0 to 100, Z each independently represents C 2-4 alkylene or hydroxyalkylene, and X each independently represents -O-, -
S- or -NR- (where R represents the same thing as defined above). However, the amine of this formula has at least one reactive -NH- or -
It shall contain NH 2 group. 5 Component (A) is diethylenetriamine, triethylenetetramine, tetraethylenepentamine, 2-
Aminoethyl-3-aminopropylamine, dipropylenetriamine or N,N-bis(3-
aminopropyl) methylamine and DCDA,
5. A process according to claim 4, wherein the reaction product is in a molar ratio of 2:1 to 1:2. 6. The method according to any one of claims 1 to 5, wherein the initial condensate of component (A) and component (B) is applied to the substrate. 7. The method according to claim 6, wherein component (B) is epichlorohydrin. 8 Components (A) and (B) are 1:0.3 to 2 based on the number of moles of DCDA or a similar compound in (A)
Claim 6 reacted in a molar ratio of
or the method described in paragraph 7. 9 Component (A) and component (B) in an aqueous solution, initial stage of 6 to 9
9. A method according to any of claims 6 to 8, wherein the reaction is performed at PH. 10 Claims 1 to 9 in which the base material is cotton
The method described in any of the paragraphs. 11. The method according to any one of claims 1 to 10, wherein the substrate is dyed or printed with a direct dye. 12. The method of claim 11, wherein the direct dye is a copper acetate dye. 13. Process according to any one of claims 1 to 11, in which the catalyst (F) is present and the precondensate is applied by padding. 14. Claim 13, wherein the crosslinking step is carried out by heat curing at 170 to 180°C for 30 seconds to 1 minute.
The method described in section. Claim 6, in which the precondensates of 15 (A) and (B) are used, the application is carried out by exhaustion, and the crosslinking step is carried out under alkaline conditions in an exhaustion bath.
9. The method according to any one of items 9 to 9. 16(A) Reaction products of mono- or polyfunctional primary or secondary amines with cyanamide, dicyandiamide (DCDA), guanidine or biguanidine, or reaction products of ammonia with cyanamide or DCDA, wherein cyanamide , DCDA, up to 50 mol % of the guanidine or biguanidine may be replaced by a dicarboxylic acid or its mono- or diester, and with a reaction product containing a reactive hydrogen atom bonded to nitrogen, and (B) an epihalohydrin or (C) formaldehyde or formaldehyde precursor, or (D) dihydroxyalkylene urea or its methyl ether, and then formaldehyde or formaldehyde precursor, or (E) urea, melamine, guanamine, A post-treatment agent for dyed, printed or whitened substrates containing hydroxy group-containing fibers, comprising a catalyst for the crosslinking of N-methylol derivatives of triazinones, urons, carbamates or acid amides. 17. The post-treatment agent according to claim 16, wherein the catalyst (F) is magnesium chloride. 18. The post-treatment agent according to claim 16 or 17, which contains an initial condensate of component (A) and formaldehyde or its precursor (C) together with catalyst (F). 19 Components (A) and (C) are mixed in a ratio of 1:2 to 1, based on the number of moles of amine used to form component (A).
19. The post-treatment agent according to claim 18, which is reacted in a molar ratio of 6 to 6. 20 The initial condensate of component (A) and component (D) is
together with claim 16 or 17.
Post-treatment agent as described in section. 21. The post-treatment agent according to claim 20, wherein the amine in component (A) is represented by the following formula. RRNH In the above formula, R represents the same thing as defined in claim 4. 22 Claim 20, wherein component (D) is dihydroxyethylene urea and then formaldehyde.
The post-treatment agent according to item 21 or item 21. 23 Components (A) and (D) are 1 part of (A) to 0.625 to 22 parts of dihydroxyalkylene urea to 0.025 parts of formaldehyde.
23. Post-treatment agent according to any of claims 20 to 22, which is reacted in a weight ratio of ~12 parts (based on the dry weight of the active ingredient). 24 1-10% based on the total weight of (A) + (D)
The post-treatment agent according to any one of claims 22 to 23, which contains DCDA. 25 Claims 16 to 24 including component (E)
The post-treatment agent according to any one of paragraphs. 26 50 to 200 of the total weight of (A) + (B), (C) or (D)
26. The post-treatment agent according to claim 25, comprising component (E) in an amount of %. 27 Component (E) is N,N'-dimethylol-4,5
- dihydroxyethylene urea or its methyl ether Claim 25 or 26
Post-treatment agent as described in section. 28 The amount of catalyst (F) is 7.5 to 7.5 of the dry weight of component (E)
The post-treatment agent according to any one of claims 25 to 27, which has a content of 12.5%.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3119115 | 1981-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57193584A JPS57193584A (en) | 1982-11-27 |
| JPH0160110B2 true JPH0160110B2 (en) | 1989-12-21 |
Family
ID=6132255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57079262A Granted JPS57193584A (en) | 1981-05-14 | 1982-05-13 | Post-treatment for improving dyeing fastness |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57193584A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2557603B1 (en) * | 1984-01-03 | 1988-02-19 | Sandoz Sa | PROCESS FOR DYEING AND AFTER-TREATING TEXTILE SUBSTRATES |
| JPS6144925A (en) * | 1984-07-21 | 1986-03-04 | ãµã³ããã¢ã¯ããšã³ã²ãŒã«ã·ã€ãã | Cationic polycondensate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5571884A (en) * | 1978-11-27 | 1980-05-30 | Nippon Senka Kogyo Kk | Enhancing of dye fastness |
| JPS5643483A (en) * | 1979-09-18 | 1981-04-22 | Sanyo Chemical Ind Ltd | Dyestuff fixing agent |
-
1982
- 1982-05-13 JP JP57079262A patent/JPS57193584A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5571884A (en) * | 1978-11-27 | 1980-05-30 | Nippon Senka Kogyo Kk | Enhancing of dye fastness |
| JPS5643483A (en) * | 1979-09-18 | 1981-04-22 | Sanyo Chemical Ind Ltd | Dyestuff fixing agent |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57193584A (en) | 1982-11-27 |
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