CH618723A5 - - Google Patents

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Info

Publication number: CH618723A5
Authority: CH; Switzerland
Prior art keywords: pink; cha; dye; amino; fibers
Prior art date: 1974-11-15

Application number

CH1458175A

Other languages

German (de)

English (en)

Inventor

Friedrich Wilhelm Kroeck

Rudolf Braden

Ruetger Neeff

Volker Hederich

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1974-11-15

Filing date

1975-11-11

Publication date

1980-08-15

1975-11-11 Application filed by Bayer Ag filed Critical Bayer Ag

1980-08-15 Publication of CH618723A5 publication Critical patent/CH618723A5/de

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
239000000975 dye Substances 0.000 description 56
125000004093 cyano group Chemical group *C#N 0.000 description 48
239000000835 fiber Substances 0.000 description 29
239000000203 mixture Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
-1 pyrrolidone- (2) Chemical compound 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
239000013078 crystal Substances 0.000 description 14
238000004043 dyeing Methods 0.000 description 14
229920000139 polyethylene terephthalate Polymers 0.000 description 14
239000005020 polyethylene terephthalate Substances 0.000 description 14
238000000034 method Methods 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000004744 fabric Substances 0.000 description 12
229920000728 polyester Polymers 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
239000004952 Polyamide Substances 0.000 description 11
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 11
229920002647 polyamide Polymers 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000004040 coloring Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 5
229920002284 Cellulose triacetate Polymers 0.000 description 5
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 5
150000007514 bases Chemical class 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
238000000859 sublimation Methods 0.000 description 5
230000008022 sublimation Effects 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
GRPCILYSCDCPJA-UHFFFAOYSA-N 4-(hydroxymethyl)cyclohexane-1-carbonitrile Chemical compound OCC1CCC(C#N)CC1 GRPCILYSCDCPJA-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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 description 4
238000009826 distribution Methods 0.000 description 4
238000007037 hydroformylation reaction Methods 0.000 description 4
229920006306 polyurethane fiber Polymers 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
MLVHSWTXNJFUPW-UHFFFAOYSA-N 4-(2-cyanoethyl)-5-(hydroxymethyl)bicyclo[2.2.1]heptane-3-carbonitrile Chemical compound C1C(C#N)C2(CCC#N)C(CO)CC1C2 MLVHSWTXNJFUPW-UHFFFAOYSA-N 0.000 description 3
GFACODIELBOEKD-UHFFFAOYSA-N 5-(hydroxymethyl)bicyclo[2.2.1]heptane-3-carbonitrile Chemical compound C1C(C#N)C2C(CO)CC1C2 GFACODIELBOEKD-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
229920000098 polyolefin Polymers 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
235000011449 Rosa Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000001000 anthraquinone dye Substances 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
239000000292 calcium oxide Substances 0.000 description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000003599 detergent Substances 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000002657 fibrous material Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
238000009998 heat setting Methods 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
SUHLUMKZPUMAFP-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1O SUHLUMKZPUMAFP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
125000005717 substituted cycloalkylene group Chemical group 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
NLVZWCVHFAZLLL-UHFFFAOYSA-N 1-amino-2-(4-chlorophenoxy)-4-hydroxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=C(Cl)C=C1 NLVZWCVHFAZLLL-UHFFFAOYSA-N 0.000 description 1
MSSQDESMUMSQEN-UHFFFAOYSA-N 1-amino-2-bromo-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Br)=C2N MSSQDESMUMSQEN-UHFFFAOYSA-N 0.000 description 1
MFAVJLWGAQYYNX-UHFFFAOYSA-N 1-amino-2-chloro-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Cl)=C2N MFAVJLWGAQYYNX-UHFFFAOYSA-N 0.000 description 1
WSPPHHAIMCTKNN-UHFFFAOYSA-N 1-amino-4-hydroxy-2-methoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(O)=C3C(=O)C2=C1 WSPPHHAIMCTKNN-UHFFFAOYSA-N 0.000 description 1
ZGDOXWZYKDETSP-UHFFFAOYSA-N 1-amino-4-hydroxy-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(S(O)(=O)=O)=C2N ZGDOXWZYKDETSP-UHFFFAOYSA-N 0.000 description 1
XZWIYSPVASNDHN-UHFFFAOYSA-N 1-hydroxy-4-phenoxyanthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=C1OC1=CC=CC=C1 XZWIYSPVASNDHN-UHFFFAOYSA-N 0.000 description 1
ZYJSCLFZVYYHFF-UHFFFAOYSA-N 4-(2-cyanoethyl)-5-formylbicyclo[2.2.1]heptane-3-carbonitrile Chemical compound C1C(C#N)C2(CCC#N)C(C=O)CC1C2 ZYJSCLFZVYYHFF-UHFFFAOYSA-N 0.000 description 1
ZZJVCWHVKHHLHA-UHFFFAOYSA-N 4-(2-cyanoethyl)bicyclo[2.2.1]hept-2-ene-5-carbonitrile Chemical compound C1C2CC(C#N)C1(CCC#N)C=C2 ZZJVCWHVKHHLHA-UHFFFAOYSA-N 0.000 description 1
MXLMQSVWZCSRMN-UHFFFAOYSA-N 4-(2-cyanoethyl)bicyclo[2.2.1]hept-5-ene-2-carbonitrile Chemical compound C1C2C=CC1(CCC#N)CC2C#N MXLMQSVWZCSRMN-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
STBQONQRIDTODI-UHFFFAOYSA-N 5-amino-2,3,3-trifluoro-8-hydroxy-6-phenoxy-2H-anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC(F)C(F)(F)C=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 STBQONQRIDTODI-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
101100041822 Schizosaccharomyces pombe (strain 972 / ATCC 24843) sce3 gene Proteins 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
229920006221 acetate fiber Polymers 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
BMAXQTDMWYDIJX-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carbonitrile Chemical compound C1C2C(C#N)CC1C=C2 BMAXQTDMWYDIJX-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
GYBNBQFUPDFFQX-UHFFFAOYSA-N cyclohex-3-ene-1-carbonitrile Chemical compound N#CC1CCC=CC1 GYBNBQFUPDFFQX-UHFFFAOYSA-N 0.000 description 1
VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 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
238000009987 spinning Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 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
- 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
- D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/922—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
- D06P1/924—Halogenated hydrocarbons
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/20—Anthraquinone dyes
- 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
- Y10S8/921—Cellulose ester or ether
- 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
- Y10S8/922—Polyester fiber
- 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
- 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
- Y10S8/926—Polyurethane fiber

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Dispersion Chemistry (AREA)
Coloring (AREA)

CH1458175A 1974-11-15 1975-11-11 CH618723A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742454327 DE2454327A1 (de)	1974-11-15	1974-11-15	Anthrachinonfarbstoffe

Publications (1)

Publication Number	Publication Date
CH618723A5 true CH618723A5 (fr)	1980-08-15

Family

ID=5930974

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1458175A CH618723A5 (fr)	1974-11-15	1975-11-11

Country Status (9)

Country	Link
US (1)	US4035398A (fr)
JP (1)	JPS51132220A (fr)
BE (1)	BE835537A (fr)
BR (1)	BR7507503A (fr)
CH (1)	CH618723A5 (fr)
DE (1)	DE2454327A1 (fr)
ES (1)	ES442640A1 (fr)
FR (1)	FR2291255A1 (fr)
GB (1)	GB1474303A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5641177Y2 (fr) *	1976-11-30	1981-09-26
DE3216455A1 (de) *	1982-05-03	1983-11-17	Bayer Ag, 5090 Leverkusen	Anthrachinonfarbstoffe, ihre herstellung und verwendung sowie dichtroitisches material enthaltend diese anthrachinonfarbstoffe
FR2613947A1 (fr) *	1987-04-17	1988-10-21	Promorep Sarl	Conception d'un tapis de judo

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3329692A (en) *	1962-07-09	1967-07-04	Ciba Ltd	1-amino-4-hydroxy-2-(cyano- and cyanoalkyl-phenoxy)-anthraquinones
GB1145904A (en) *	1965-04-17	1969-03-19	Mitsubishi Chem Ind	Disperse anthraquinone dyestuffs
US3264325A (en) *	1965-05-11	1966-08-02	American Cyanamid Co	1-amino-2-[2-(2-cyanoethoxy) ethoxy]-4-hydroxyanthraquinone
DE2316294A1 (de) *	1973-03-31	1974-10-10	Basf Ag	Anthrachinoide dispersionsfarbstoffe

1974
- 1974-11-15 DE DE19742454327 patent/DE2454327A1/de not_active Withdrawn
1975
- 1975-10-15 GB GB4226075A patent/GB1474303A/en not_active Expired
- 1975-11-11 CH CH1458175A patent/CH618723A5/de not_active IP Right Cessation
- 1975-11-11 US US05/630,778 patent/US4035398A/en not_active Expired - Lifetime
- 1975-11-13 BR BR7507503*A patent/BR7507503A/pt unknown
- 1975-11-13 JP JP50135737A patent/JPS51132220A/ja active Pending
- 1975-11-13 BE BE161838A patent/BE835537A/fr unknown
- 1975-11-14 FR FR7534832A patent/FR2291255A1/fr active Granted
- 1975-11-14 ES ES442640A patent/ES442640A1/es not_active Expired

Also Published As

Publication number	Publication date
FR2291255B1 (fr)	1979-07-13
JPS51132220A (en)	1976-11-17
GB1474303A (en)	1977-05-25
US4035398A (en)	1977-07-12
BR7507503A (pt)	1976-08-10
FR2291255A1 (fr)	1976-06-11
ES442640A1 (es)	1977-04-16
BE835537A (fr)	1976-05-13
DE2454327A1 (de)	1976-05-20

Legal Events

Date	Code	Title	Description
1982-07-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2926183A1 (de)	1980-01-03	Kationische farbstoffe
DE2510045A1 (de)	1975-09-11	Marineblaue monoazo-dispersionsfarbstoffe
DE2850994C2 (fr)	1988-12-22
DE2237289C3 (de)	1975-03-06	Verwendung von 5,8-disubstituierten 1-Nitrobenzoylaminoanthrachinonverbindungen als wasserunlösliche, nicht verküpbare Anthrachinonfarbstoffe zum Färben von Cellulosefasern und Kunstfasern, insbesondere in Wasser quellbaren Cellulosefasern
DE2405152C3 (de)	1978-12-14	Sulfongruppenhaltige Anthrachinonverbindungen, ihre Herstellung und ihre Verwendung
DE1793172C3 (de)	1974-05-16	Anthrachinonfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2454327A1 (de)	1976-05-20	Anthrachinonfarbstoffe
DE1644653A1 (de)	1970-09-17	Farbstoffe der Anthrachinonreihe,ihre Herstellung und Verwendung
DE2447878C3 (de)	1979-02-08	Cumarinverbindungen, ihre Herstellung und ihre Verwendung
EP0341206A1 (fr)	1989-11-08	Colorants formazane réactifs avec les fibres
DE2460668C2 (de)	1984-07-12	Monoazofarbstoffe, ihre Herstellung und Verwendung
DE1807492A1 (de)	1969-06-19	Dispersionsfarbstoffe der Anthrachinonreihe,ihre Herstellung und Verwendung
DE1644663C3 (de)	1975-02-20	Anthrachinon-Reaktlvfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
AT221511B (de)	1962-06-12	Verfahren zur Herstellung von N-substituierten β-Hydroxypropionsäureamid-Derivaten
AT233134B (de)	1964-04-25	Verfahren zur Herstellung von neuen Farbstoffen der Azo-, Anthrachinon- und Tetrazaporphinreihe
DE2319230A1 (de)	1973-10-25	Neue farbstoffe, ihre herstellung und ihre verwendung
DE2331056C2 (de)	1982-12-09	Anthrachinonfarbstoffe sowie deren Herstellung und Verwendung zum Färben von Fasermaterialien
EP0027930A2 (fr)	1981-05-06	Colorants azlactones insolubles dans l'eau, procédé pour leur préparation et leur utilisation pour la teinture ou l'impression de matières fibreuses synthétiques
DE2304320B2 (de)	1981-09-10	Nitroanthrachinone
DE2301892A1 (de)	1974-07-18	Anthrachinonfarbstoffe
DE1810156A1 (de)	1970-03-12	Verfahren zur Herstellung von sauren Anthrachinonfarbstoffen
DE2531557A1 (de)	1977-02-03	Anthrachinonfarbstoffe
DE2307591A1 (de)	1974-08-29	Anthrachinonverbindungen
DE1137155B (de)	1962-09-27	Verfahren zur Herstellung wasserloeslicher Tetrazaporphinfarbstoffe
DE1917024A1 (de)	1969-10-09	Verfahren zur Herstellung von in Wasser schwerloeslichen Anthrachinonfarbstoffen