DE2626836A1 - Reaktiv-gefaerbte polymere substrate, besonders textilsubstrate, verfahren zu deren bildung und reaktivfarbstoffe bzw. -farbstoffsysteme hierfuer - Google Patents
Reaktiv-gefaerbte polymere substrate, besonders textilsubstrate, verfahren zu deren bildung und reaktivfarbstoffe bzw. -farbstoffsysteme hierfuerInfo
- Publication number
- DE2626836A1 DE2626836A1 DE19762626836 DE2626836A DE2626836A1 DE 2626836 A1 DE2626836 A1 DE 2626836A1 DE 19762626836 DE19762626836 DE 19762626836 DE 2626836 A DE2626836 A DE 2626836A DE 2626836 A1 DE2626836 A1 DE 2626836A1
- Authority
- DE
- Germany
- Prior art keywords
- dye
- group
- formula
- cyanamide
- substrate
- 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 title claims description 202
- 239000000758 substrate Substances 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 48
- 239000004753 textile Substances 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 13
- 229920000642 polymer Polymers 0.000 title claims description 12
- 230000015572 biosynthetic process Effects 0.000 title claims description 8
- 239000000985 reactive dye Substances 0.000 title description 22
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 35
- 239000007864 aqueous solution Substances 0.000 claims description 34
- -1 cyanamide compound Chemical class 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000000835 fiber Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229920002678 cellulose Polymers 0.000 claims description 9
- 239000001913 cellulose Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 2
- 238000004045 reactive dyeing Methods 0.000 claims description 2
- 150000002791 naphthoquinones Chemical class 0.000 claims 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229920000307 polymer substrate Polymers 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 58
- 239000000243 solution Substances 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 229920000742 Cotton Polymers 0.000 description 25
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 23
- 238000004043 dyeing Methods 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 15
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
- 230000004048 modification Effects 0.000 description 14
- 238000012986 modification Methods 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 229960004050 aminobenzoic acid Drugs 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 230000008878 coupling Effects 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- HTPJPKXFBLUBPI-UHFFFAOYSA-I pentasodium 5-[[4-[[4-anilino-6-[[8-hydroxy-7-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]diazenyl]-3,6-disulfonatonaphthalen-1-yl]amino]-1,3,5-triazin-2-yl]amino]phenyl]diazenyl]-2-hydroxybenzoate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].COc1cc(N=Nc2cc(cc3cc(cc(O)c23)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2c(Nc3nc(Nc4ccccc4)nc(Nc4ccc(cc4)N=Nc4ccc(O)c(c4)C([O-])=O)n3)cc(cc2cc1S([O-])(=O)=O)S([O-])(=O)=O HTPJPKXFBLUBPI-UHFFFAOYSA-I 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- RTBLVNSNIFUUFC-UHFFFAOYSA-L disodium;2-[[3-methyl-5-oxo-1-(4-sulfonatophenyl)-4h-pyrazol-4-yl]diazenyl]benzoate Chemical compound [Na+].[Na+].CC1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=CC=C1C([O-])=O RTBLVNSNIFUUFC-UHFFFAOYSA-L 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000001044 red dye Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000000987 azo dye Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001912 cyanamides Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000001043 yellow dye Substances 0.000 description 4
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 2
- DACUJXBUANTBKE-UHFFFAOYSA-N 4-acetamido-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(NC(=O)C)=CC(S(O)(=O)=O)=CC2=C1 DACUJXBUANTBKE-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ZWONWYNZSWOYQC-UHFFFAOYSA-N 5-benzamido-3-[[5-[[4-chloro-6-(4-sulfoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OC1=C(N=NC2=CC(NC3=NC(NC4=CC=C(C=C4)S(O)(=O)=O)=NC(Cl)=N3)=CC=C2S(O)(=O)=O)C(=CC2=C1C(NC(=O)C1=CC=CC=C1)=CC(=C2)S(O)(=O)=O)S(O)(=O)=O ZWONWYNZSWOYQC-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000001000 anthraquinone dye Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 235000019646 color tone Nutrition 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- PBOIUUROGJVVNC-UHFFFAOYSA-L disodium 2-hydroxy-5-[[4-[[2-methoxy-4-[(3-sulfonatophenyl)diazenyl]phenyl]carbamoylamino]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].COc1cc(ccc1NC(=O)Nc1ccc(cc1)N=Nc1ccc(O)c(c1)C([O-])=O)N=Nc1cccc(c1)S([O-])(=O)=O PBOIUUROGJVVNC-UHFFFAOYSA-L 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 150000002895 organic esters Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- GTYIXXVMPDCSMV-UHFFFAOYSA-M sodium 5-[(4-acetamidophenyl)diazenyl]-2-hydroxybenzoate Chemical compound C(C)(=O)NC1=CC=C(C=C1)N=NC=1C=CC(=C(C(=O)[O-])C=1)O.[Na+] GTYIXXVMPDCSMV-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- OAOBMEMWHJWPNA-UHFFFAOYSA-N (4-aminophenyl)phosphonic acid Chemical compound NC1=CC=C(P(O)(O)=O)C=C1 OAOBMEMWHJWPNA-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- SWHUGXBRBHHKFB-UHFFFAOYSA-N 1-(3-aminophenyl)-5-oxo-4h-pyrazole-3-carboxylic acid Chemical compound NC1=CC=CC(N2C(CC(=N2)C(O)=O)=O)=C1 SWHUGXBRBHHKFB-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- CGCWRLDEYHZQCW-UHFFFAOYSA-N 2-nitrophenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1[N+]([O-])=O CGCWRLDEYHZQCW-UHFFFAOYSA-N 0.000 description 1
- QBEKPTZMBQXQQH-UHFFFAOYSA-N 3-[n-(2-carboxyethyl)-3-methylanilino]propanoic acid Chemical compound CC1=CC=CC(N(CCC(O)=O)CCC(O)=O)=C1 QBEKPTZMBQXQQH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- BTCCOOALVRZZGD-UHFFFAOYSA-N 4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC(Br)=C3C(=O)C2=C1 BTCCOOALVRZZGD-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- UEALKTCRMBVTFN-UHFFFAOYSA-N 4-nitroanthranilic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1C(O)=O UEALKTCRMBVTFN-UHFFFAOYSA-N 0.000 description 1
- SLBQXWXKPNIVSQ-UHFFFAOYSA-N 4-nitrophthalic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1C(O)=O SLBQXWXKPNIVSQ-UHFFFAOYSA-N 0.000 description 1
- GVCFFVPEOLCYNN-UHFFFAOYSA-N 5-amino-2-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C(C(O)=O)=C1 GVCFFVPEOLCYNN-UHFFFAOYSA-N 0.000 description 1
- QRRSIFNWHCKMSW-UHFFFAOYSA-N 5-methyl-2-nitrobenzoic acid Chemical compound CC1=CC=C([N+]([O-])=O)C(C(O)=O)=C1 QRRSIFNWHCKMSW-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 235000003913 Coccoloba uvifera Nutrition 0.000 description 1
- 241000592774 Coolia Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 240000008976 Pterocarpus marsupium Species 0.000 description 1
- 241000567363 Puccinellia maritima Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- DBDVUUCUDYNZHB-UHFFFAOYSA-K azocard green g Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=C(C(O)=CC=3)C([O-])=O)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 DBDVUUCUDYNZHB-UHFFFAOYSA-K 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- PQZVCRPSQXDXJL-UHFFFAOYSA-N butylcyanamide Chemical compound CCCCNC#N PQZVCRPSQXDXJL-UHFFFAOYSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- SOGFATPCYLMCMQ-UHFFFAOYSA-N dibutylcyanamide Chemical compound CCCCN(C#N)CCCC SOGFATPCYLMCMQ-UHFFFAOYSA-N 0.000 description 1
- ZZTSQZQUWBFTAT-UHFFFAOYSA-N diethylcyanamide Chemical compound CCN(CC)C#N ZZTSQZQUWBFTAT-UHFFFAOYSA-N 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- RBOUZBUAZMPIJV-UHFFFAOYSA-L disodium 5-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-2-hydroxybenzoate Chemical compound [Na+].[Na+].Nc1c(cc(c2ccccc12)S([O-])(=O)=O)N=Nc1ccc(cc1)-c1ccc(cc1)N=Nc1ccc(O)c(c1)C([O-])=O RBOUZBUAZMPIJV-UHFFFAOYSA-L 0.000 description 1
- FAQUHXBTAIFQMH-UHFFFAOYSA-L disodium 5-[[4-[4-[[2,6-diamino-3-methyl-5-[(4-sulfonatophenyl)diazenyl]phenyl]diazenyl]phenyl]phenyl]diazenyl]-2-hydroxy-3-methylbenzoate Chemical compound [Na+].[Na+].Cc1cc(N=Nc2ccc(cc2)S([O-])(=O)=O)c(N)c(N=Nc2ccc(cc2)-c2ccc(cc2)N=Nc2cc(C)c(O)c(c2)C([O-])=O)c1N FAQUHXBTAIFQMH-UHFFFAOYSA-L 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- MCLITRXWHZUNCQ-UHFFFAOYSA-N methylcyanamide Chemical compound CNC#N MCLITRXWHZUNCQ-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/68—Preparing azo dyes on the material
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
- C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58884075A | 1975-06-20 | 1975-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2626836A1 true DE2626836A1 (de) | 1976-12-30 |
Family
ID=24355512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762626836 Withdrawn DE2626836A1 (de) | 1975-06-20 | 1976-06-15 | Reaktiv-gefaerbte polymere substrate, besonders textilsubstrate, verfahren zu deren bildung und reaktivfarbstoffe bzw. -farbstoffsysteme hierfuer |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4111648A (enExample) |
| JP (1) | JPS521188A (enExample) |
| AR (1) | AR208956A1 (enExample) |
| AU (1) | AU503798B2 (enExample) |
| BE (1) | BE843133A (enExample) |
| BR (1) | BR7603954A (enExample) |
| CA (1) | CA1078555A (enExample) |
| CH (1) | CH630769GA3 (enExample) |
| DE (1) | DE2626836A1 (enExample) |
| FR (1) | FR2316374A1 (enExample) |
| GB (1) | GB1514395A (enExample) |
| IT (1) | IT1065639B (enExample) |
| MX (1) | MX143090A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4171954A (en) * | 1975-06-20 | 1979-10-23 | Burlington Industries, Inc. | Reactive dyeing systems using dyes with carboxylic acid groups on polyvinyl alcohol |
| JPS562679Y2 (enExample) * | 1977-04-09 | 1981-01-21 | ||
| DE2809675C3 (de) * | 1978-03-07 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Färbeverfahren |
| US4340386A (en) * | 1978-05-04 | 1982-07-20 | Scott Paper Company | Cationic dyestuff printing inks |
| US4221562A (en) * | 1978-05-04 | 1980-09-09 | Scott Paper Company | Bleed-fast cationic dyestuffs |
| US4351638A (en) * | 1981-09-21 | 1982-09-28 | Burlington Industries, Inc. | Process of reactively dyeing and printing toweling |
| US8129193B2 (en) * | 2009-07-30 | 2012-03-06 | Anaspec Incorporated | Thiol quantitation assays and related methods |
| CN114032215B (zh) * | 2021-12-28 | 2022-05-17 | 江南大学 | 一种分泌红2g单克隆抗体的杂交瘤细胞株及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB486010A (en) * | 1936-11-03 | 1938-05-20 | Ig Farbenindustrie Ag | Improvements in dyeing textile fibres |
| GB571056A (en) * | 1943-08-26 | 1945-08-03 | Henry Dreyfus | Colouration of textile materials |
| DE1087673B (de) | 1958-06-03 | 1960-08-25 | Licentia Gmbh | Verriegelungsschaltung gegen vorzeitiges Wiedereinschalten fuer ein Verzoegerungsrelais mit Bi-Metallkontakt und Heizwiderstand |
| DE1280807B (de) | 1961-04-20 | 1968-10-24 | Sandoz Ag | Verfahren zum Fixieren von Farbstoffen |
| DE1230393B (de) * | 1962-02-08 | 1966-12-15 | Vondelingen Plaat Bv | Verfahren zum Faerben von Protein- oder Polyamidfasermaterialien |
| CH400995A (de) * | 1963-01-25 | 1965-05-31 | Ciba Geigy | Verfahren zum Färben und Bedrucken nach dem Vigoureuxdruckverfahren von natürlichen, stickstoffhaltigen textilen Materialien |
| CH398499A (de) * | 1963-08-29 | 1966-03-15 | Ciba Geigy | Verfahren zum Färben oder Bedrucken von Textilfasern aus natürlichem, stickstoffhaltigem Material faseriger Struktur |
| DE1644074C3 (de) * | 1967-12-01 | 1974-12-12 | Basf Ag, 6700 Ludwigshafen | Sulfonsäuregruppenhaltige Monoazofarbstoffe, Verfahren zu deren Herstellung und Farbstoffzubereitungen |
| US3535308A (en) * | 1968-01-15 | 1970-10-20 | American Cyanamid Co | Process for the preparation of partially esterified polyhydroxylic polymers |
-
1976
- 1976-06-10 MX MX165073A patent/MX143090A/es unknown
- 1976-06-15 DE DE19762626836 patent/DE2626836A1/de not_active Withdrawn
- 1976-06-17 AU AU15016/76A patent/AU503798B2/en not_active Expired
- 1976-06-18 BR BR7603954A patent/BR7603954A/pt unknown
- 1976-06-18 JP JP51071256A patent/JPS521188A/ja active Pending
- 1976-06-18 AR AR263661A patent/AR208956A1/es active
- 1976-06-18 CA CA255,198A patent/CA1078555A/en not_active Expired
- 1976-06-18 IT IT49994/76A patent/IT1065639B/it active
- 1976-06-18 GB GB25453/76A patent/GB1514395A/en not_active Expired
- 1976-06-18 FR FR7618721A patent/FR2316374A1/fr active Granted
- 1976-06-18 BE BE168080A patent/BE843133A/xx unknown
- 1976-06-19 CH CH782976A patent/CH630769GA3/de unknown
-
1977
- 1977-02-28 US US05/772,738 patent/US4111648A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AR208956A1 (es) | 1977-03-15 |
| GB1514395A (en) | 1978-06-14 |
| JPS521188A (en) | 1977-01-06 |
| AU1501676A (en) | 1977-12-22 |
| US4111648A (en) | 1978-09-05 |
| FR2316374A1 (fr) | 1977-01-28 |
| CA1078555A (en) | 1980-06-03 |
| IT1065639B (it) | 1985-03-04 |
| CH630769GA3 (enExample) | 1982-07-15 |
| BR7603954A (pt) | 1977-03-22 |
| AU503798B2 (en) | 1979-09-20 |
| MX143090A (es) | 1981-03-13 |
| BE843133A (fr) | 1976-12-20 |
| FR2316374B1 (enExample) | 1980-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: BERENDT, T., DIPL.-CHEM. DR., PAT.-ANW., 8000 MUEN |
|
| 8139 | Disposal/non-payment of the annual fee |