DE2447229A1 - Styrylfarbstoffe - Google Patents
StyrylfarbstoffeInfo
- Publication number
- DE2447229A1 DE2447229A1 DE19742447229 DE2447229A DE2447229A1 DE 2447229 A1 DE2447229 A1 DE 2447229A1 DE 19742447229 DE19742447229 DE 19742447229 DE 2447229 A DE2447229 A DE 2447229A DE 2447229 A1 DE2447229 A1 DE 2447229A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- methyl
- alkyl
- formula
- chlorine
- 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- Withdrawn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 53
- -1 methoxy- Chemical class 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 238000004043 dyeing Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000005504 styryl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical group N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 239000012209 synthetic fiber Substances 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001299 aldehydes Chemical class 0.000 description 17
- 239000002585 base Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 229920000728 polyester Polymers 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920002284 Cellulose triacetate Polymers 0.000 description 6
- 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 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 description 3
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 239000000986 disperse dye Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OUDNYQQUONSKLK-UHFFFAOYSA-N 3-(5,7-dichloro-1,3-benzoxazol-2-yl)phenol Chemical compound OC1=CC=CC(C=2OC3=C(Cl)C=C(Cl)C=C3N=2)=C1 OUDNYQQUONSKLK-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- MVDWJSYJWKQJEA-UHFFFAOYSA-N (4-chlorophenyl)methyl 2-cyanoacetate Chemical compound ClC1=CC=C(COC(=O)CC#N)C=C1 MVDWJSYJWKQJEA-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- SGKKITHZCABJJW-UHFFFAOYSA-N 2,3,3,7-tetramethyl-1,2-dihydroindole Chemical compound CC1(C)C(C)NC2=C1C=CC=C2C SGKKITHZCABJJW-UHFFFAOYSA-N 0.000 description 1
- NFACTFFHALHFAT-UHFFFAOYSA-N 2,5-diethoxy-n-methylaniline Chemical compound CCOC1=CC=C(OCC)C(NC)=C1 NFACTFFHALHFAT-UHFFFAOYSA-N 0.000 description 1
- GHGZVWOTJDLREY-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC2=CC=CC=C2O1 GHGZVWOTJDLREY-UHFFFAOYSA-N 0.000 description 1
- WKZRPPBUMLPCRF-UHFFFAOYSA-N 2-(1h-indol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC2=CC=CC=C2N1 WKZRPPBUMLPCRF-UHFFFAOYSA-N 0.000 description 1
- TUCSLJFYSQXGEV-UHFFFAOYSA-N 2-Butylbenzothiazole Chemical compound C1=CC=C2SC(CCCC)=NC2=C1 TUCSLJFYSQXGEV-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- GKNAVHDPXXWEME-UHFFFAOYSA-N 2-cyanoethyl 2-cyanoacetate Chemical compound N#CCC(=O)OCCC#N GKNAVHDPXXWEME-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical group CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- CCYRVFJDASAJTG-UHFFFAOYSA-N 2-ethyl-n-methylaniline Chemical compound CCC1=CC=CC=C1NC CCYRVFJDASAJTG-UHFFFAOYSA-N 0.000 description 1
- CMOQNSVFSKVGJA-UHFFFAOYSA-N 2-methoxy-n,5-dimethylaniline Chemical compound CNC1=CC(C)=CC=C1OC CMOQNSVFSKVGJA-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QHUYLIOMTFQOSN-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)phenol Chemical compound OC1=CC=CC(C=2OC3=CC=CC=C3N=2)=C1 QHUYLIOMTFQOSN-UHFFFAOYSA-N 0.000 description 1
- VUUHXRVVDUAGOL-UHFFFAOYSA-N 3-(3-methylanilino)propanenitrile Chemical compound CC1=CC=CC(NCCC#N)=C1 VUUHXRVVDUAGOL-UHFFFAOYSA-N 0.000 description 1
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 1
- KBCJPWUCWTXJEW-UHFFFAOYSA-N 3-bromo-n-ethylaniline Chemical compound CCNC1=CC=CC(Br)=C1 KBCJPWUCWTXJEW-UHFFFAOYSA-N 0.000 description 1
- LUNFYXBUYWMPBY-UHFFFAOYSA-N 3-chloro-n-ethylaniline Chemical compound CCNC1=CC=CC(Cl)=C1 LUNFYXBUYWMPBY-UHFFFAOYSA-N 0.000 description 1
- IPYRMSULEHPLDI-UHFFFAOYSA-N 3-ethoxy-n-methylaniline Chemical compound CCOC1=CC=CC(NC)=C1 IPYRMSULEHPLDI-UHFFFAOYSA-N 0.000 description 1
- ZFMZSZMUFWRAOG-UHFFFAOYSA-N 3-methoxy-n-methylaniline Chemical compound CNC1=CC=CC(OC)=C1 ZFMZSZMUFWRAOG-UHFFFAOYSA-N 0.000 description 1
- IUNVPXVTJRNCEK-UHFFFAOYSA-N 3-methyl-n-propylaniline Chemical compound CCCNC1=CC=CC(C)=C1 IUNVPXVTJRNCEK-UHFFFAOYSA-N 0.000 description 1
- JSZPVLCUIXSKOW-UHFFFAOYSA-N 3-phenylpropyl 2-cyanoacetate Chemical compound N#CCC(=O)OCCCC1=CC=CC=C1 JSZPVLCUIXSKOW-UHFFFAOYSA-N 0.000 description 1
- YRPIXORGESANFA-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)phenol Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(O)C=C1 YRPIXORGESANFA-UHFFFAOYSA-N 0.000 description 1
- DHMLUYFYGCILBZ-UHFFFAOYSA-N 7-methyl-2-propyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=C(C)C=C2NC(CCC)CCC2=C1 DHMLUYFYGCILBZ-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- BJUKZTWBBSZYKK-UHFFFAOYSA-N [Cl].C1=CC=C2NCCC2=C1 Chemical compound [Cl].C1=CC=C2NCCC2=C1 BJUKZTWBBSZYKK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000004705 aldimines Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- RCUIWQWWDLZNMS-UHFFFAOYSA-N benzyl 2-cyanoacetate Chemical compound N#CCC(=O)OCC1=CC=CC=C1 RCUIWQWWDLZNMS-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- RKGLUDFWIKNKMX-UHFFFAOYSA-L dilithium;sulfate;hydrate Chemical compound [Li+].[Li+].O.[O-]S([O-])(=O)=O RKGLUDFWIKNKMX-UHFFFAOYSA-L 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- FLLXIDNFXBLBMT-UHFFFAOYSA-N n,2,5-trimethylaniline Chemical compound CNC1=CC(C)=CC=C1C FLLXIDNFXBLBMT-UHFFFAOYSA-N 0.000 description 1
- FBGJJTQNZVNEQU-UHFFFAOYSA-N n,3-dimethylaniline Chemical compound CNC1=CC=CC(C)=C1 FBGJJTQNZVNEQU-UHFFFAOYSA-N 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- OGXBDPVULQEBSG-UHFFFAOYSA-N n-(2-methoxyethyl)-3-methylaniline Chemical compound COCCNC1=CC=CC(C)=C1 OGXBDPVULQEBSG-UHFFFAOYSA-N 0.000 description 1
- REUFZACIJMPYOK-UHFFFAOYSA-N n-(2-phenylethyl)aniline Chemical compound C=1C=CC=CC=1NCCC1=CC=CC=C1 REUFZACIJMPYOK-UHFFFAOYSA-N 0.000 description 1
- QVXMQKVVQBXQPK-UHFFFAOYSA-N n-[3-(ethylamino)phenyl]acetamide Chemical compound CCNC1=CC=CC(NC(C)=O)=C1 QVXMQKVVQBXQPK-UHFFFAOYSA-N 0.000 description 1
- IMIKXWKMQJWNPM-UHFFFAOYSA-N n-[3-(methylamino)phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(NC)=C1 IMIKXWKMQJWNPM-UHFFFAOYSA-N 0.000 description 1
- IWXYQQZZRQBFKF-UHFFFAOYSA-N n-benzyl-3-methoxyaniline Chemical compound COC1=CC=CC(NCC=2C=CC=CC=2)=C1 IWXYQQZZRQBFKF-UHFFFAOYSA-N 0.000 description 1
- HHZDSDSOSVITOZ-UHFFFAOYSA-N n-benzyl-3-methylaniline Chemical compound CC1=CC=CC(NCC=2C=CC=CC=2)=C1 HHZDSDSOSVITOZ-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- ODQBTYAYKGLSCH-UHFFFAOYSA-N n-butyl-3-chloroaniline Chemical compound CCCCNC1=CC=CC(Cl)=C1 ODQBTYAYKGLSCH-UHFFFAOYSA-N 0.000 description 1
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 1
- SVXBISMQGDORIF-UHFFFAOYSA-N n-cyclopentyl-3-methylaniline Chemical compound CC1=CC=CC(NC2CCCC2)=C1 SVXBISMQGDORIF-UHFFFAOYSA-N 0.000 description 1
- MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
- AFQXCZCRJSGHPB-UHFFFAOYSA-N n-ethyl-3-methoxyaniline Chemical compound CCNC1=CC=CC(OC)=C1 AFQXCZCRJSGHPB-UHFFFAOYSA-N 0.000 description 1
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
- ZOFYRRQYYKRASX-UHFFFAOYSA-N n-ethyl-3-phenoxyaniline Chemical compound CCNC1=CC=CC(OC=2C=CC=CC=2)=C1 ZOFYRRQYYKRASX-UHFFFAOYSA-N 0.000 description 1
- SRDCXRIXVSRXMS-UHFFFAOYSA-N n-methyl-2-propan-2-ylaniline Chemical compound CNC1=CC=CC=C1C(C)C SRDCXRIXVSRXMS-UHFFFAOYSA-N 0.000 description 1
- QBTKCLQCPGRXNQ-UHFFFAOYSA-N n-propyl-3-(trifluoromethyl)aniline Chemical compound CCCNC1=CC=CC(C(F)(F)F)=C1 QBTKCLQCPGRXNQ-UHFFFAOYSA-N 0.000 description 1
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NLFIMXLLXGTDME-UHFFFAOYSA-N propyl 2-cyanoacetate Chemical compound CCCOC(=O)CC#N NLFIMXLLXGTDME-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 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
- D06P1/16—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
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742447229 DE2447229A1 (de) | 1974-10-03 | 1974-10-03 | Styrylfarbstoffe |
| US05/617,142 US4046771A (en) | 1974-10-03 | 1975-09-26 | Styryl dyestuffs |
| CH1260275A CH594027A5 (en:Method) | 1974-10-03 | 1975-09-29 | |
| GB4014475A GB1466207A (en) | 1974-10-03 | 1975-10-01 | Styryl dyestuffs |
| JP50117781A JPS5161532A (en:Method) | 1974-10-03 | 1975-10-01 | |
| FR7530383A FR2286862A1 (fr) | 1974-10-03 | 1975-10-03 | Colorants styryliques, leur obtention et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742447229 DE2447229A1 (de) | 1974-10-03 | 1974-10-03 | Styrylfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2447229A1 true DE2447229A1 (de) | 1976-04-15 |
Family
ID=5927450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742447229 Withdrawn DE2447229A1 (de) | 1974-10-03 | 1974-10-03 | Styrylfarbstoffe |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4046771A (en:Method) |
| JP (1) | JPS5161532A (en:Method) |
| CH (1) | CH594027A5 (en:Method) |
| DE (1) | DE2447229A1 (en:Method) |
| FR (1) | FR2286862A1 (en:Method) |
| GB (1) | GB1466207A (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1130052A3 (de) * | 2000-02-29 | 2003-11-12 | Bayer Ag | Verfahren zum Massefärben von Kunststoffen |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861897A (en) * | 1987-06-22 | 1989-08-29 | Ortho Pharmaceutical Corporation | 2-Aryloxyalkylaminobenzoxazoles and 2-aryloxyalkylaminobenzothiazoles |
| US6372770B1 (en) * | 1994-10-12 | 2002-04-16 | Euro-Celtique, S.A. | Benzoxazoles |
| US20070190325A1 (en) * | 2003-12-04 | 2007-08-16 | Katja Berg-Schultz | Microcapsules with uv filter activity and process for producing them |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH505875A (de) * | 1966-08-29 | 1971-04-15 | Ciba Geigy Ag | Verfahren zur Herstellung von wasserunlöslichen Styrylfarbstoffen |
| DD111920A5 (en:Method) * | 1973-04-04 | 1975-03-12 |
-
1974
- 1974-10-03 DE DE19742447229 patent/DE2447229A1/de not_active Withdrawn
-
1975
- 1975-09-26 US US05/617,142 patent/US4046771A/en not_active Expired - Lifetime
- 1975-09-29 CH CH1260275A patent/CH594027A5/xx not_active IP Right Cessation
- 1975-10-01 GB GB4014475A patent/GB1466207A/en not_active Expired
- 1975-10-01 JP JP50117781A patent/JPS5161532A/ja active Pending
- 1975-10-03 FR FR7530383A patent/FR2286862A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1130052A3 (de) * | 2000-02-29 | 2003-11-12 | Bayer Ag | Verfahren zum Massefärben von Kunststoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1466207A (en) | 1977-03-02 |
| FR2286862B1 (en:Method) | 1980-07-25 |
| FR2286862A1 (fr) | 1976-04-30 |
| CH594027A5 (en:Method) | 1977-12-30 |
| US4046771A (en) | 1977-09-06 |
| JPS5161532A (en:Method) | 1976-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |