GB2031929A - Monoazo dyestuffs - Google Patents
Monoazo dyestuffs Download PDFInfo
- Publication number
- GB2031929A GB2031929A GB7931103A GB7931103A GB2031929A GB 2031929 A GB2031929 A GB 2031929A GB 7931103 A GB7931103 A GB 7931103A GB 7931103 A GB7931103 A GB 7931103A GB 2031929 A GB2031929 A GB 2031929A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyestuff
- amino
- general formula
- naphthalene
- same meanings
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 6
- 230000008878 coupling Effects 0.000 claims abstract description 15
- 238000010168 coupling process Methods 0.000 claims abstract description 15
- 238000005859 coupling reaction Methods 0.000 claims abstract description 15
- 238000004043 dyeing Methods 0.000 claims abstract description 15
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 6
- 150000002790 naphthalenes Chemical class 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
- 230000001590 oxidative effect Effects 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000009918 complex formation Effects 0.000 claims description 2
- OKJPPOJRBHKUND-UHFFFAOYSA-N n,n-difluorotriazin-4-amine Chemical compound FN(F)C1=CC=NN=N1 OKJPPOJRBHKUND-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 239000004744 fabric Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 239000004627 regenerated cellulose Substances 0.000 abstract description 2
- 239000004753 textile Substances 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 210000002268 wool Anatomy 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 22
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 17
- -1 amino, hydroxyl Chemical group 0.000 description 16
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 14
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 14
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
- 229940075566 naphthalene Drugs 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 7
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 229960002449 glycine Drugs 0.000 description 7
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 7
- 229960003080 taurine Drugs 0.000 description 7
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 5
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- WSYUEVRAMDSJKL-UHFFFAOYSA-N ethanolamine-o-sulfate Chemical compound NCCOS(O)(=O)=O WSYUEVRAMDSJKL-UHFFFAOYSA-N 0.000 description 5
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JSBQMQFABBMNSV-UHFFFAOYSA-N 4-aminonaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 JSBQMQFABBMNSV-UHFFFAOYSA-N 0.000 description 4
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- QUFFRITXLMVPMV-UHFFFAOYSA-N 4-aminonaphthalene-1,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 QUFFRITXLMVPMV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 2
- RKDUVPVDHFMLPC-UHFFFAOYSA-N 4,6-difluorotriazine Chemical class FC1=CC(F)=NN=N1 RKDUVPVDHFMLPC-UHFFFAOYSA-N 0.000 description 2
- NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- HIVUAOXLSJITPA-UHFFFAOYSA-N 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 HIVUAOXLSJITPA-UHFFFAOYSA-N 0.000 description 1
- GOXHTPXOPKICJS-UHFFFAOYSA-N 3-amino-4-hydroxy-7-nitronaphthalene-1,5-disulfonic acid Chemical compound C1=C([N+]([O-])=O)C=C(S(O)(=O)=O)C2=C(O)C(N)=CC(S(O)(=O)=O)=C21 GOXHTPXOPKICJS-UHFFFAOYSA-N 0.000 description 1
- ZDFCTUISEBJBEQ-UHFFFAOYSA-N 3-amino-4-hydroxynaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=C(O)C(N)=CC(S(O)(=O)=O)=C21 ZDFCTUISEBJBEQ-UHFFFAOYSA-N 0.000 description 1
- MTIBLCIOPCKHAL-UHFFFAOYSA-N 3-amino-4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=C(O)C2=C1 MTIBLCIOPCKHAL-UHFFFAOYSA-N 0.000 description 1
- VNWVMZDJPMCAKD-UHFFFAOYSA-N 3-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1O VNWVMZDJPMCAKD-UHFFFAOYSA-N 0.000 description 1
- LYHAPFBXMNSTEZ-UHFFFAOYSA-N 3-amino-8-hydroxynaphthalene-1,5-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 LYHAPFBXMNSTEZ-UHFFFAOYSA-N 0.000 description 1
- YPENQCJGPPXRTD-UHFFFAOYSA-N 4,6-difluoro-n,n-dimethyl-1,3,5-triazin-2-amine Chemical compound CN(C)C1=NC(F)=NC(F)=N1 YPENQCJGPPXRTD-UHFFFAOYSA-N 0.000 description 1
- WLFJHLQHIMSZEI-UHFFFAOYSA-N 4,6-difluoro-n-propyl-1,3,5-triazin-2-amine Chemical compound CCCNC1=NC(F)=NC(F)=N1 WLFJHLQHIMSZEI-UHFFFAOYSA-N 0.000 description 1
- MHTVJXAMWWXQSE-UHFFFAOYSA-N 4-(4,6-difluoro-1,3,5-triazin-2-yl)morpholine Chemical compound FC1=NC(F)=NC(N2CCOCC2)=N1 MHTVJXAMWWXQSE-UHFFFAOYSA-N 0.000 description 1
- BDHMHVFXQQVGII-UHFFFAOYSA-N 4-[(4-aminobenzoyl)amino]-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC(O)=C12 BDHMHVFXQQVGII-UHFFFAOYSA-N 0.000 description 1
- DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 1
- JLMVULREWBLCCD-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 JLMVULREWBLCCD-UHFFFAOYSA-N 0.000 description 1
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
- MIMAWHGPNFLBIA-UHFFFAOYSA-N 4-amino-5-(benzenesulfonyloxy)naphthalene-1,7-disulfonic acid Chemical compound C=12C(N)=CC=C(S(O)(=O)=O)C2=CC(S(O)(=O)=O)=CC=1OS(=O)(=O)C1=CC=CC=C1 MIMAWHGPNFLBIA-UHFFFAOYSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- LOJYZZQPQSCOCH-UHFFFAOYSA-N 6-acetamidonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(NC(=O)C)=CC=C21 LOJYZZQPQSCOCH-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- NMACEEIRVDQGRH-UHFFFAOYSA-N 6-amino-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound NC1=C(C=2C=C(C=C(C2C=C1)S(=O)(=O)O)S(=O)(=O)O)O NMACEEIRVDQGRH-UHFFFAOYSA-N 0.000 description 1
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
- OAEWJWQHOOSVLC-UHFFFAOYSA-N 7-(4-amino-3-sulfoanilino)-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1NC1=CC=C(C(O)=CC(=C2)S(O)(=O)=O)C2=C1 OAEWJWQHOOSVLC-UHFFFAOYSA-N 0.000 description 1
- IQBZRZXJPYXCDP-UHFFFAOYSA-N 7-acetamidonaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(NC(=O)C)=CC=C21 IQBZRZXJPYXCDP-UHFFFAOYSA-N 0.000 description 1
- YXKDOVFPRNRPQU-UHFFFAOYSA-N 7-amino-8-hydroxynaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C(O)C(N)=CC(S(O)(=O)=O)=C21 YXKDOVFPRNRPQU-UHFFFAOYSA-N 0.000 description 1
- WQUVEZKAOVRUBG-UHFFFAOYSA-N 7-amino-8-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C(O)C(N)=CC=C21 WQUVEZKAOVRUBG-UHFFFAOYSA-N 0.000 description 1
- VWDQLJRKTSNXFU-UHFFFAOYSA-N 8-hydroxynaphthalene-1,3,5-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 VWDQLJRKTSNXFU-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100083253 Caenorhabditis elegans pho-1 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical group NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HTQNRRWSDLDDNY-UHFFFAOYSA-N n-butyl-4,6-difluoro-1,3,5-triazin-2-amine Chemical compound CCCCNC1=NC(F)=NC(F)=N1 HTQNRRWSDLDDNY-UHFFFAOYSA-N 0.000 description 1
- LYUYXBAFSMHXEX-UHFFFAOYSA-N n-ethyl-4,6-difluoro-1,3,5-triazin-2-amine Chemical compound CCNC1=NC(F)=NC(F)=N1 LYUYXBAFSMHXEX-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/095—Metal complex azo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Dyestuffs of the formula <IMAGE> wherein B is a direct bond or a bridge member, R is hydrogen or C1-C4-alkyl, R1 and R2 are hydrogen, optionally substituted alkyl or cycloalkyl, or (R1 + R2) form a ring with the N atom and optionally a further hetero atom, n is a 1-6, D is a diazo component of the naphthalene series, K is a coupling component of the naphthalene series, both D and K being free from reactive groups and B being linked to an aromatic carbon atom in K, and their use for dyeing and printing materials containing hydroxyl groups or amide groups, such as textile fibres, filaments and fabrics of wool, silk or synthetic polyamide or polyurethane fibres, and for dyeing and printing natural or regenerated cellulose in dyeings and prints which are fast to washing.
Description
SPECIFICATION
Monoazo Dyestuffs
The present invention relates to azo dyestuffs of the formula
wherein
B = a direct bond or a bridge member,
R = hydrogen or C1-C4-alkyl, R1 and R2 = hydrogen, optionally substituted alkyl
or cycloalkyl, or
R1 and R2 form a ring with the nitrogen atom,
optionally including a further hetero-atom,
n 6 an integer from 1 to 6,
D = the radical of a diazo component of the naphtha
lene series and
K = the radical of a coupling component of the
naphthalene series, both D and K being free from
reactive groups.
The bridge member B is linked to an aromatic-carbocyclic C atom of K.
The radicals D and K can carry the substituents customary for azo dyestuffs, for example: halogen atoms, such as fluorine, chlorine or bromine, C1-C4-alkyl, C1-C4-alkoxy or carboxyl, amino, hydroxyl, nitro, sulphonamide or acetylamino groups.
The following are examples of bridge members B:
and
B is preferably a direct bond.
Examples of suitable optionally substituted alkyl radicals R1 and R2 are: methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-pentyl, n-hexyl, ss-hydroxyethyl, ss-methoxyethyl, P-ethoxyethyl, carboxymethyl, e-sulphoethyl, phenylmethyl, ss-phenylethyl and cyclohexyl.
Preferred alkyl radicals R1 and R2 are C1-C4-alkyl radicals. The following are examples of cyclic radicals of the formula
Examples of the aminohydroxynaphthalenes
on which the dyestuffs (I) are based (after oxidative coppering if appropriate) are 1-amino-2,8-dihydroxynaphthalene-3,6- or -4,6-disulphonic acid, 2-amino-1 -hydroxynaphthalene-4,8-disulphonic acid, 2-amino-1 -hydroxynaphthalene-4,6,8-trisulphonic acid, 2-amino-1 -hydroxynaphthalene-3,6-disulphonic acid, 2-amino-1 -hydroxynaphthalene-5,7-disulphonic acid, 2-amino-1 -hydroxynaphthalene-6,8-disulphonic acid, 2-amino-1 -hydroxynaphthalene-3,6,8.
trisulphonic acid, 1-amino-2-hydroxynaphthalene-4-sulphonic acid, 1-amino-2-hydroxynaphthalene-4,6- disulphonic acid, 1-amino-2-hydroxynaphthalene-4,7-disulphonic acid, 1-amino-2-hydroxy-6- nitronaphthalene-4-sulphonic acid and 2-amino-i -hydroxy-6-nitronaphthalene-4,8-disulphonic acid.
Examples which may be mentioned of aminonaphthols
on which the dyestuffs I are based are the following: 2-amino-5-hydroxynaphthalene-7-sulphonic acid, 2-methyl- or -ethyl-amino-5-hydroxynaphthalene-7-sulphonic acid, 2-amino-5-hydroxynaphthalene-1 ,7- disulphonic acid, 2-amino-8-hydroxynaphthalene-6-sulphonic acid, 2-methyl- or -ethyl-amino-8hydroxynaphthalene-6-sulphonic acid, 2-amino-8-hydroxynaphthalene-3,6-disulphonic acid, 1-amino-S- hydroxy-naphthalene-7-sulphonic acid, 1 -amino-8-hydroxynaphthalene-3,6- or 4,6-disulphonic acid, 1-(4'aminobenzoylamino)-8-hydroxynaphthalene-3,6- or -4,6-disulphonic acid, 1 -(3'-aminobenzoylamino)-8- hydroxynaphthalene-3,6- or -4,6-disulphonic acid, 2-(4'-amino-3'-sulphophenylamino)-5-hydroxynaphthalene-7-sulphonic acid and 2-amino-5-hydroxy-naphthalene-4,8-disulphonic acid.
The dyestuffs (I) can be obtained by various processes:
1) Dyestuffs oftheformula
are reacted with amines of the formula
wherein R1 and R2 have the meaning indicated above, hydrofluoric acid being split off. This condensation reaction is preferably carried out in aqueous solution or suspension, at low temperatures and at a weakly acid, neutral to weakly alkaline pH value. The hydrogen fluoride liberated during the condensation reaction is advantageously continuously neutralised by adding aqueous alkali metal hydroxides, carbonates or bicarbonates. The neutralisation can also advantageously be effected with a second equivalent of amine (V), in particular with ammonia.
2) Dyestuffs oftheformula
are treated with agents which donate copper. Examples of agents which donate copper which can be used are salts which contain copper as a cation, such as, for example, copper sulphate or copper acetate.
The dyestuffs are coppered by methods which are known per se, for example at room temperature and in a neutral to weakly acid range.
3) Dyestuffs of the formula
are subjected to the oxidative coppering process, the hydroxyl group necessary for complex formation only being introduced into the radical D, in the o-position relative to the azo bridge, during the coppering reaction by the simultaneous action of an oxidising agent. (Angew. Chem. 70, 232 (1958)).
4) Dyestuffs of the formula
are reacted with difluoroaminotriazines of the formula
hydrofluoric acid being split off. This condensation reaction is preferably carried out in aqueous solution or suspension, at low temperature and at a weakly acid, neutral to weakly alkaline pH value. The hydrogen fluoride liberated during the condensation reaction is advantageously continuously neutralised by adding aqueous alkali metal hydroxides, carbonates or bicarbonates.
The following are examples of amines (V): ammonia, methylamine, ethylamine, n-propylamine, iso-propylamine, n-butylamine, iso-butylamine, t-butylamine, n-pentylamine, n-hexylamine, cyclohexylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, methylethylamine, ethanolamine, diethanolamine, frmethoxyethylamine, (3-ethoxy-ethylamine, aminoacetic acid, N-methylaminoacetic acid, taurine, N-methyltaurine, benzylamine, (3-phenylethylamine, N-methylbenzylamine, pyrrolidine, piperidine and morpholine.
The following compounds may be mentioned as examples of difluorotriazine compounds (IX): 2,4-difluoro-6-amino-1 3,5-triazine, 2,4-difl uoro-6-methylamino-1 ,3,5-triazine, 2,4-difluoro-6-dimethylamino1 ,3,5-triazine, 2,4-difluoro-6-n-propylam ino-1 3,5-triazi ne, 2,4-difluoro-6-n-propylamino-1 ,3,5-triazine, 2,4 difluoro-6-ethylamino-1 ,3,5-triazine, 2,4-difl uoro-6-diethylamino-1 ,3,5-triazine, 2,4-difluoro-6-n-butylamino 1 ,3,5-triazine, 2,4-difl uoro-6-cyclohexyl-amino-1 ,3,5-triazine and 2,4-difluoro-6-morpholino-1,3,5-triazine.
The new dyestuffs are suitable for dyeing and printing materials containing hydroxyl groups or amide groups, such as textile fibres, filaments and fabrics of wool, silk or synthetic polyamide or polyurethane fibres, and for dyeing and printing natural or regenerated cellulose in dyeings and prints which are fast to washing, the treatment of cellulose materials appropriately being carried out by the processes disclosed for reactive dyestuffs, in the presence of acid-binding agents and if appropriate by the action of heat.
The formulae indicated for the dyestuffs are those of the corresponding free acids. The dyestuffs were generally isolated and used for dyeing in the form of alkali metal salts, in particular the Na salts.
Example 1
71 g of the copper complex dyestuff obtained from 1-hydroxy-4,6,8-trisulphonaphthalene < 2 azo 2 > 1-hydroxy-3-sulpho-6-aminonaphthalene are stirred in 11 of ice-water. 13.5 g of trifluorotriazine are added dropwise in the course of 15 minutes, the pH value being kept between 3.5 and 4.5 by simultaneously adding 20% strength sodium carbonate solution. When the condensation reaction has ended, 12% strength ammonia solution is added until the pH value is 8-5-9. The temperature is allowed to rise to 5-1 00C and the pH value is kept at 8-5 - 9 until the second fluorine atom has been replaced by ammonia.After salting out, filtering off, drying and grinding the product, a red dyestuff powder which readily dissolves in water giving a violet-coloured solution is obtained.
The dyestuff corresponds to the formula
Using this dyestuff, violet dyeings are obtained on cotton by one of the dyeing processes customary for reactive dyestuffs.
The dyestuff can also be isolated by evaporating the reaction mixture or by spray-drying instead of by salting out.
If methylamine, dimethylamine, ethylamine, N-methyl-ethylamine, diethylamine, iso-propylamine, nbutylamine, N-methylethanolamine, ethanolamine, diethanolamine, sulphuric acid mono-(2-aminoethyl) ester, cyclohexylamine, aminoacetic acid, taurine, N-methyltaurine, benzylamine or morpholine is used in this example instead of ammonia, dyestuffs with similar dyeing properties result.
The aminoazo dyestuff used as the starting material in this example is obtained by diazotising 2-amino-4,6,8-trisulpho-naphthalene, coupling the diazotisation product with acetyl-l-acid, subjecting the product to oxidative coppering and then saponifying the acetyl group.
If the procedure followed is as according to the statements of this example, but compounds which are obtainable by diazotising the diazo components listed in column 1, coupling the diazotisation product with the coupling components given in column 2 and subjecting the product to oxidative coppering and then to saponification, are used instead of the aminoazo dyestuff used in this example and ammonia, methylamine, dimethylamine, ethylamine, diethylamine, iso-propylamine, n-butylamine, N-methylethylamine, ethanolamine, diethanolamine, sulphuric acid mono-(2-amino-ethyl) ester, cyclohexylamine, aminoacetic acid, taurine, N-methyltaurine, benzylamine or morpholine is used as the amine for replacing the second fluorine atom, further valuable dyestuffs which dye cotton in the shade indicated likewise result.
Example Diazo component Coupling component Colour
shade
on cotton 2 2-amino-4,8-disulphonaphthalene 1-hydroxy-6- bluish
acetylamino- tinged 4,8-disul;to- violet naphthal ,ne 3 2-amino-4,6,8-trisulphonaphthalene ,, n 4 1-amino-4,6-disulphonaphthalene * reddish
tinged
blue 5 1-amino-4,7-disulphonaphthalene 6 1-amino-8-benzenesulphonyloxy- " greenish
3,6-disulpho-naphthalene tinged
(after oxidative coppering, blue
O-benzenesulphonyl saponified) 7 1-amino-8-benzenesulphonyl-oxy- 4,6-disulpho-naphthalene
(after oxidative coppering,
O-benzenesul phonyl saponified) 8 2-amino-4,8-disulpho-naphthalene 1-hydroxy-3- claret
sulpho-6
acetylamino
naphthalene 9 2-amino-6,8-disulpho-naphthalene 10 2-amino-6-nitro-4,8-disulpho- " violet
naphthalene 11 1-amino-4,6-disulpho-naphthalene 12 1-amino-4,7-disulpho-naphthalene 13 2-amino-4,8-disulpho-naphthalene 1-hydroxy-3 " sulpho-7
acetylamino
naphthalene 14 2-amino-6,8-disulpho-naphthalene " " 15 1-amino-4,7-disulpho-naphthalene 16 1-amino-4,6-disulpho-naphthalene
Example 17
74.5 g of the dyestuff 4,8-disulpho-naphthalene < 2 azo 2 > 1 -hydroxy-3,6-disulpho-8-(2'-fluoro-4'-amino- triazin-6'-yl-amino)-naphthalene are stirred in 1 litre of water, and 28 g of CuS04. 5H2O and 42 g of NaAc.
3H20 are added. A 3% strength H202 solution is then added dropwise until the oxidative coppering has ended. The dyestuff is salted out, filtered off, dried and ground. A black-blue powder which readily dissolves in water giving a blue-coloured solution is obtained. The dyestuff corresponds to the formula
and dyes cotton blue by one of the dyeing processes customary for reactive dyestuffs.
The metal-free azo dyestuff used in this example can be prepared by diazotising 2-amino4,8-disulphonaphthalene, coupling the diazotisation product with the condensation product of 1-amino-8-hydroxy-3,6- disulpho-naphthalene and 2,4,6-trifuoro-1 3,5-triazine and then replacing one fluorine atom by ammonia.
If methylamine, dimethylamine, ethylamine, diethylamine, iso-propylamine, n-butylamine, Nmethylethanolamine, ethanolamine, diethanolamine, sulphuric acid mono-(2-amino-ethyl) ester, cyclohexylamine, aminoacetic acid, taurine, N-methylamine, benzylamine or morpholine is used in this example instead of ammonia, dyestuffs with similar dyeing properies result.
If the procedure followed is as according to the statements of this example, but compounds which are obtainable by diazotising the diazo components listed in column 1, coupling the diazotisation product with the coupling components given in column 2 and replacing the second fluorine atom by ammonia, methylamine, dimethylamine, ethylamine, diethylamine, iso-propylamine, n-butylamine, Nmethylethylamine, ethanolamine, diethanolamine, sulphuric acid mono-(2-amino-ethyl) ester, cyclohexylamine, amino-acetic acid, taurine, N-methylamine, benzylamine or morpholine are used instead of the copper-free dyestuff used in this example, further valuable dyestuffs which dye cotton in the shade indicated likewise result.
Examples Diazo component Coupling component Colour
shade
on cotton 18 2-amino-4,8-disulpho- 1-hydroxy-8-(2',4'-difluoro- blue
naphthalene triazin-6'-yl-amino)-3,6
disulpho-naphthalene 19 2-amino-4,6,8-trisulpho- naphthalene 20 2-amino-3,6-disulpho
naphthalene 21 2-amino-6,8-disulpho
naphthalene 22 2-amino-5,7-disulpho- I, naphthalene 23 1-amino-4,6-disulpho- " tt naphthalene 24 1-amino-4,7-disulpho- " " naphthalene 25 1-amino-3,6-disulpho- naphthalene 26 2-am ino-4,8-disul pho- 1 -hydroxy-8-(2',4'-difluoro- naphthalene triazin-6'-yl-amino)-4,6
disulpho-naphthalene 27 2-amino-6,8-disulpho- naphthalene 28 2-amino-4,6,8-trisulpho
naphthalene 29 1-amino-4,6-disulpho- " " naphthalene 30 l-amino-4,7-disulpho- naphthalene
Example 31 86.4 g of the dyestuff 4,8-disulpho-naphthalene < 2 azo 2 > 1 -hydroxy-3,6-disulpho-8-(4'-(2"-fluoro-4"- amino-triazin-6"-yl-amino)-benzoylamino)-naphthalene are stirred in 1 litre of water, and 28 g of CuS04.
5H2O and 42 g of NaAc. 3H2O are added. A 3% strength H202 solution is then added dropwise until the oxidative coppering has ended. The dyestuff is salted out, filtered off, dried and ground. A black-blue powder which readily dissolves in water giving a blue-coloured solution is obtained. The dyestuff corresponds to the formula
It dyes cotton blue by one of the dyeing processes customary for reactive dyestuffs.
The metal-free azo dyestuff used for this example can be prepared by diazotising 2-amino-4,8-disulphonaphthalene, coupling the diazotisation product with 1 -hydroxy-3,6-disulpho-8-(4'-amino-benzoylamino) naphthalene, acylating the product with 2,4,6-trifluoro-1 3,5-triazine and then replacing a fluorine atom by ammonia.
If methylamine, dimethylamine, ethylamine, diethylamine, iso-propylamine, n-butylamine, Nmethylethanolamine, ethanolamine, diethanolamine, sulphuric acid mono-(2-aminoethyi) ester, cyclollexy- lamine, aminoacetic acid, taurine, N-methylamine, benzylamine or morpholine is used in this example instead of ammonia, dyestuffs with similar dyeing properties result.
If the procedure followed is as according to the statements of this example, but compounds which are obtainable by diazotising the diazo components listed in column 1, coupling the diazotisation product with the coupling components given in column 2, acylating the product with trifluorotriazine and replacing the second fluorine atom by ammonia, methylamine, dimethylamine, ethylamine, diethylamine, isopropylamine, n-butylamine, N-methylethylamine, ethanolamine, diethanolamine, sulphuric acid mono-(2amino-ethyl) ester, cyclohexylamine, aminoacetic acid, taurine, N-methylamine, benzylamine or morpholine are used instead of the copper-free dyestuff used in this example, further valuable dyestuffs which dye cotton in the shade indicated likewise result.
Example Diazo component Coupling component Colour
shade
on cotton 32 2-amino-4,6,8-trisu Ipho- 1 -hydroxy-8-(4'-amino- blue
naphthalene benzoylamino)-3,6- disulpho-naphthalene 33 2-amino-4,6,8-trisulpho- 1-hydroxy-8-(3'-amino- N naphthalene benzoylamino)-3,6
disulpho-naphthalene 34 2-amino-3,6-disulpho
naphthalene 35 2-amino-6,8-disulpho
naphthalene 36 2-amino-5,7-disulpho
naphthalene 37 1-amino-4,6-disulpho- naphthalene 38 1-amino-4,7-disuipho- D 11 naphthalene 39 1-amino-3,6-disulpho- naphthalene 40 2.amino-6-nitro-4,8- " t disulpho-naphthalene
Claims (11)
1. A monoazo dyestuff of the general formula
in which
B denotes a direct bond or a bridge member linked
to an aromatic carbocyclic carbon atom or radical
K,
R denotes a hydrogen atom or a C1 to C4 alkyl group,
R1 and B2 independently denote a hydrogen atom or an
optionally substituted alkyl or cycloalkyl group, or,
R1 and R2 form a ring with the nitrogen atom,
optionally including a further hetero-atom,
n is 1,2,3,4,5 or 6, K denotes a radical of a coupling component of the
naphthalene series and
D denotes a radical of a diazo component of the naphtha
lene series, both K and D being free from reactive groups.
2. A monoazo dyestuff according to claim 1 in which B denotes a direct bond.
3. A monoazo dyestuff according to claim 1 as hereinbefore specifically identified
4. A process for the production of a dyestuff as claimed in claim 1 in which a dyestuff of the general formula
in which B, R, n K and D have the same meanings as in claim 1, is reacted with an amine of the general formula
in which R1 and R2 have the same meanings as in claim 1, hydrofluoric acid being split off.
5. A process for the production of a dyestuff as claimed in claim 1 in which a dyestuff of the general formula
in which B, R, R1, R2, n, K and D have the same meanings as in claim 1, is treated with an agent which donates copper.
6. A process for the production of a dyestuff as claimed in claim 1 in which a dyestuff of the general formula
in which B, R, R1, R2, n, K and D have the same meanings as in claim 1, is subjected to oxidative coppering, the hydroxyl group necessary for complex formation only being introduced into the radical D, in the o-position relative to the azo bridge, during the coppering reaction by the simultaneous action of an oxidising agent.
7. A process for the production of a dyestuff as claimed in claim 1 in which a dyestuff of the general formula
in which B, R, n, K and D have the same meanings as in claim 1, is reacted with a difluoroaminotriazine of the general formula
in which R1 and R2 have the same meanings as in claim 1, hydrofluoric acid being split off.
8. A process for the production of a dyestuff as claimed in claim 1 when carried out substantialiy as described in any one of the Examples.
9. A dyestuff as claimed in claim 1 when produced by the process of any of claims 4 to 8.
10. A process for dyeing or printing a material containing hydroxyl groups or amide groups comprising treating the material with a monoazo dyestuff as claimed in any of claims 1 to 3 and 9.
11. A material containing hydroxyl groups or amide group when dyed or printed by the process of claim 10.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782839562 DE2839562A1 (en) | 1978-09-12 | 1978-09-12 | FIBER REACTIVE AZO DYES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2031929A true GB2031929A (en) | 1980-04-30 |
| GB2031929B GB2031929B (en) | 1982-11-24 |
Family
ID=6049208
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7931103A Expired GB2031929B (en) | 1978-09-12 | 1979-09-07 | Monoazo dyestuffs |
| GB7931104A Expired GB2031930B (en) | 1978-09-12 | 1979-09-07 | Monoazo dyestuffs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7931104A Expired GB2031930B (en) | 1978-09-12 | 1979-09-07 | Monoazo dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| JP (3) | JPS5538894A (en) |
| DE (1) | DE2839562A1 (en) |
| FR (2) | FR2436167A1 (en) |
| GB (2) | GB2031929B (en) |
| IT (2) | IT7925579A0 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3116296A1 (en) * | 1981-04-24 | 1982-11-11 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING COPPER COMPLEX AZO DYES |
| MXPA03002684A (en) | 2000-10-10 | 2003-10-15 | Clariant Finance Bvi Ltd | Fiber-reactive copper complexes of monoazo dyes. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627749A (en) * | 1963-07-10 | 1971-12-14 | Geigy Ag J R | Mono-and disazo dyestuffs containing triazinylureylene groups |
| CH438533A (en) * | 1963-07-10 | 1967-06-30 | Geigy Ag J R | Process for the preparation of reactive azo dyes |
| DE1644208C3 (en) * | 1967-04-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Reactive dyes |
| CH626650A5 (en) * | 1974-12-18 | 1981-11-30 | Ciba Geigy Ag | |
| LU75328A1 (en) * | 1976-07-08 | 1978-02-08 | ||
| CH629839A5 (en) * | 1976-07-12 | 1982-05-14 | Ciba Geigy Ag | Process for preparing fibre-reactive azo dyes |
| DE2634497C2 (en) * | 1976-07-31 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | Reactive dyes and their use |
| DE2655625C2 (en) * | 1976-12-08 | 1986-04-10 | Bayer Ag, 5090 Leverkusen | Metal complex dyes |
| DE2753695A1 (en) * | 1977-12-02 | 1979-06-07 | Basf Ag | Mixts. of copper complex reactive azo dyes - for use on cellulose and polyamide fibres and leather |
-
1978
- 1978-09-12 DE DE19782839562 patent/DE2839562A1/en not_active Withdrawn
-
1979
- 1979-09-07 GB GB7931103A patent/GB2031929B/en not_active Expired
- 1979-09-07 GB GB7931104A patent/GB2031930B/en not_active Expired
- 1979-09-10 IT IT7925579A patent/IT7925579A0/en unknown
- 1979-09-10 IT IT7925581A patent/IT7925581A0/en unknown
- 1979-09-11 JP JP11578679A patent/JPS5538894A/en active Pending
- 1979-09-11 JP JP11578879A patent/JPS5538896A/en active Pending
- 1979-09-11 FR FR7922704A patent/FR2436167A1/en active Granted
- 1979-09-11 JP JP11578779A patent/JPS5538895A/en active Pending
- 1979-09-12 FR FR7922789A patent/FR2436165A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2436165A1 (en) | 1980-04-11 |
| GB2031930A (en) | 1980-04-30 |
| IT7925581A0 (en) | 1979-09-10 |
| DE2839562A1 (en) | 1980-03-27 |
| JPS5538896A (en) | 1980-03-18 |
| FR2436165B1 (en) | 1983-12-02 |
| JPS5538894A (en) | 1980-03-18 |
| FR2436167A1 (en) | 1980-04-11 |
| JPS5538895A (en) | 1980-03-18 |
| FR2436167B1 (en) | 1984-03-23 |
| GB2031929B (en) | 1982-11-24 |
| GB2031930B (en) | 1982-11-24 |
| IT7925579A0 (en) | 1979-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |