DD260077A5 - Neue farbsalze, verfahren zu ihrer herstellung und ihre verwendung - Google Patents

Neue farbsalze, verfahren zu ihrer herstellung und ihre verwendung Download PDF

Info

Publication number: DD260077A5
Authority: DD; German Democratic Republic
Prior art keywords: cation; scn; compound; formula; divalent
Prior art date: 1985-12-28

Application number

DD86298296A

Other languages

German (de)

English (en)

Inventor

Kurt Hohmann

Peter Mischke

Wolfgang Teige

Original Assignee

��@��k��

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.)

1985-12-28

Filing date

1986-12-23

Publication date

1988-09-14

1986-12-23 Application filed by ��@��k�� filed Critical ��@��k��

1988-09-14 Publication of DD260077A5 publication Critical patent/DD260077A5/de

Links

150000003839 salts Chemical class 0.000 title claims abstract description 70
238000000034 method Methods 0.000 title claims abstract description 34
238000004519 manufacturing process Methods 0.000 title description 2
-1 iron cation Chemical class 0.000 claims abstract description 84
239000000975 dye Substances 0.000 claims abstract description 81
150000001450 anions Chemical class 0.000 claims abstract description 19
150000001768 cations Chemical class 0.000 claims abstract description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052751 metal Inorganic materials 0.000 claims abstract description 11
239000002184 metal Substances 0.000 claims abstract description 11
229910052742 iron Inorganic materials 0.000 claims abstract description 10
229910052717 sulfur Chemical group 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract description 3
YWMAPNNZOCSAPF-UHFFFAOYSA-N Nickel(1+) Chemical compound [Ni+] YWMAPNNZOCSAPF-UHFFFAOYSA-N 0.000 claims abstract description 3
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims abstract description 3
229940006444 nickel cation Drugs 0.000 claims abstract description 3
125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
229940006486 zinc cation Drugs 0.000 claims abstract description 3
239000011701 zinc Substances 0.000 claims description 65
150000001875 compounds Chemical class 0.000 claims description 34
125000002091 cationic group Chemical group 0.000 claims description 24
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 15
239000007864 aqueous solution Substances 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
150000001342 alkaline earth metals Chemical class 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
239000007900 aqueous suspension Substances 0.000 claims description 3
QYTOONVFPBUIJG-UHFFFAOYSA-N azane;cyanic acid Chemical compound [NH4+].[O-]C#N QYTOONVFPBUIJG-UHFFFAOYSA-N 0.000 claims description 3
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 3
238000011084 recovery Methods 0.000 claims description 3
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical group [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 2
150000001341 alkaline earth metal compounds Chemical class 0.000 claims 1
229910017052 cobalt Inorganic materials 0.000 abstract description 3
239000010941 cobalt Substances 0.000 abstract description 3
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 56
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
238000004043 dyeing Methods 0.000 description 37
239000000243 solution Substances 0.000 description 33
125000000217 alkyl group Chemical group 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
239000000460 chlorine Substances 0.000 description 17
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
125000003545 alkoxy group Chemical group 0.000 description 13
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 13
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
238000009987 spinning Methods 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 11
229920000642 polymer Polymers 0.000 description 10
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
125000004093 cyano group Chemical group *C#N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 8
229920001577 copolymer Polymers 0.000 description 8
239000000203 mixture Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 7
125000002947 alkylene group Chemical group 0.000 description 7
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
239000004246 zinc acetate Substances 0.000 description 7
150000005840 aryl radicals Chemical class 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000011787 zinc oxide Substances 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
0 CCOc(cc(cc1)N*2ccc(*)cc2)c1N*C Chemical compound CCOc(cc(cc1)N*2ccc(*)cc2)c1N*C 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
125000005236 alkanoylamino group Chemical group 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical group 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
229920002239 polyacrylonitrile Polymers 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
125000000547 substituted alkyl group Chemical group 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
239000003086 colorant Substances 0.000 description 4
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000000395 magnesium oxide Substances 0.000 description 4
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000049 pigment Substances 0.000 description 4
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
150000001555 benzenes Chemical class 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000005345 coagulation Methods 0.000 description 3
230000015271 coagulation Effects 0.000 description 3
239000000835 fiber Substances 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
150000002790 naphthalenes Chemical class 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
239000011550 stock solution Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000001302 tertiary amino group Chemical group 0.000 description 3
238000002166 wet spinning Methods 0.000 description 3
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
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 2
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 2
NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
206010039587 Scarlet Fever Diseases 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
238000013459 approach Methods 0.000 description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000010949 copper Substances 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
125000003010 ionic group Chemical group 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910052596 spinel Inorganic materials 0.000 description 2
239000011029 spinel Substances 0.000 description 2
238000010186 staining Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
125000001425 triazolyl group Chemical group 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
229910000368 zinc sulfate Inorganic materials 0.000 description 2
229960001763 zinc sulfate Drugs 0.000 description 2
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical group C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
LJJPQCFMNPGTLQ-UHFFFAOYSA-M 2-(n-ethylanilino)ethyl-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCN(CC)C1=CC=CC=C1 LJJPQCFMNPGTLQ-UHFFFAOYSA-M 0.000 description 1
MAAWLGRQUWBBPZ-UHFFFAOYSA-N 2-[diethylamino(methyl)amino]-N,N-dimethylaniline Chemical compound CN(C)C1=C(N(C)N(CC)CC)C=CC=C1 MAAWLGRQUWBBPZ-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
SPWPAFQLIZTXFN-UHFFFAOYSA-M 4-methoxy-n-methyl-n-[(1,3,3-trimethylindol-1-ium-2-yl)methylideneamino]aniline;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(OC)=CC=C1N(C)\N=C\C1=[N+](C)C2=CC=CC=C2C1(C)C SPWPAFQLIZTXFN-UHFFFAOYSA-M 0.000 description 1
KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
RQDXZPRTXAJTPZ-MQEUWQHPSA-N CC(C)=C(/C=C\C=C)/C(/N)=C(\C=C)/O Chemical compound CC(C)=C(/C=C\C=C)/C(/N)=C(\C=C)/O RQDXZPRTXAJTPZ-MQEUWQHPSA-N 0.000 description 1
AWMBNZCKZOIBMA-UHFFFAOYSA-N CC1(C=CC(c2nc(ccc(C)c3)c3[s]2)=CC1)N Chemical compound CC1(C=CC(c2nc(ccc(C)c3)c3[s]2)=CC1)N AWMBNZCKZOIBMA-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000099774 Cuscuta salina Species 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
239000005083 Zinc sulfide Substances 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000006356 alkylene carbonyl group Chemical group 0.000 description 1
125000005529 alkyleneoxy group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
239000001000 anthraquinone dye Substances 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000001691 aryl alkyl amino group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
239000002585 base Substances 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
WIVXEZIMDUGYRW-UHFFFAOYSA-L copper(i) sulfate Chemical compound [Cu+].[Cu+].[O-]S([O-])(=O)=O WIVXEZIMDUGYRW-UHFFFAOYSA-L 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000008021 deposition Effects 0.000 description 1
239000001002 diarylmethane dye Substances 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000000578 dry spinning Methods 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
229960002089 ferrous chloride Drugs 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000009434 installation Methods 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006224 matting agent Substances 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
125000005528 methosulfate group Chemical group 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000000178 monomer Substances 0.000 description 1
GTIKMPFJLWCUCO-UHFFFAOYSA-N n,n'-diethyl-n,n'-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1N(CC)CCN(CC)C1=CC=CC=C1 GTIKMPFJLWCUCO-UHFFFAOYSA-N 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
ZYWBYRRGYPCDEY-UHFFFAOYSA-N n-(2-chlorophenyl)-n'-ethyl-n'-phenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1N(CC)CCNC1=CC=CC=C1Cl ZYWBYRRGYPCDEY-UHFFFAOYSA-N 0.000 description 1
MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
RRIWRJBSCGCBID-UHFFFAOYSA-L nickel sulfate hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-]S([O-])(=O)=O RRIWRJBSCGCBID-UHFFFAOYSA-L 0.000 description 1
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical compound C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
125000000286 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
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
239000001016 thiazine dye Substances 0.000 description 1
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
239000001003 triarylmethane dye Substances 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1
239000001018 xanthene dye Substances 0.000 description 1
229910052984 zinc sulfide Inorganic materials 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
125000005853 β-dimethylaminoethyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
- 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
- Y10S8/927—Polyacrylonitrile fiber

Landscapes

Chemical & Material Sciences (AREA)
Inorganic Chemistry (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

DD86298296A 1985-12-28 1986-12-23 Neue farbsalze, verfahren zu ihrer herstellung und ihre verwendung DD260077A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853546294 DE3546294A1 (de)	1985-12-28	1985-12-28	Neue farbsalze, verfahren zu ihrer herstellung und ihre verwendung

Publications (1)

Publication Number	Publication Date
DD260077A5 true DD260077A5 (de)	1988-09-14

Family

ID=6289667

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86298296A DD260077A5 (de)	1985-12-28	1986-12-23	Neue farbsalze, verfahren zu ihrer herstellung und ihre verwendung

Country Status (5)

Country	Link
US (1)	US4732573A (fr)
EP (1)	EP0228043A3 (fr)
JP (1)	JPS62158765A (fr)
DD (1)	DD260077A5 (fr)
DE (1)	DE3546294A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5376151A (en) *	1993-04-16	1994-12-27	North Carolina State University	Environmentally friendly method for producing lightfast black shades on natural and synthetic substrates
US7179530B2 (en) *	2001-12-03	2007-02-20	Rebac Gmbh	Antimicrobial composite material
EP1342411A1 (fr) *	2002-03-05	2003-09-10	Luisi & Clement GmbH	Matériau composite antibactérien
ATE331437T1 (de) *	2001-12-03	2006-07-15	Luisi & Clement Gmbh	Antimikrobielles verbundmaterial
WO2007131875A1 (fr) *	2006-05-11	2007-11-22	Ciba Holding Inc.	Supports de stockage optiques haute capacité comprenant des paires d'ions métallisés hétérocycliques

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3271383A (en) *	1963-06-11	1966-09-06	Mitsubishi Chem Ind	Disazo dyes containing an nu-substituted benzothiazolyl group
US3291788A (en) *	1965-09-27	1966-12-13	Mitsubishi Chem Ind	Cationic triazole disazo dyestuffs
BE754714A (fr) *	1969-08-28	1971-01-18	Du Pont	Procede pour teindre des fibres de polyamides avec des colorants cationiques
FR2260659B1 (fr) *	1974-02-08	1976-11-26	Ugine Kuhlmann
DE2433233C3 (de) *	1974-07-11	1980-03-06	Hoechst Ag, 6000 Frankfurt	Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitril
US4607071A (en) *	1978-05-26	1986-08-19	Hoechst Aktiengesellschaft	Process for spin-dyeing of acid-modified polymers of copolymers of acrylonitrile using rapid-fixing di-quaternary cationic dyes
DE2822913C2 (de) *	1978-05-26	1982-08-19	Hoechst Ag, 6000 Frankfurt	Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitrils
DE2945028A1 (de) *	1979-11-08	1981-05-21	Hoechst Ag, 6000 Frankfurt	Quartaere und basische azamethinverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel
EP0055221A3 (fr) *	1980-12-24	1983-06-15	Ciba-Geigy Ag	Sels de colorants monocationiques
US4367334A (en) *	1980-12-24	1983-01-04	Ciba-Geigy Corporation	Borontetrafluoride salts of basic oxazine dyes
US4382801A (en) *	1980-12-24	1983-05-10	Ciba-Geigy Corporation	Process for spin dyeing polymers or copolymers of acrylonitrile with quaternized heterocyclic diazo dye and tetrafluoro-borate anion
DD207226A5 (de) *	1980-12-24	1984-02-22	Ciba Geigy	Verfahren zum spinnfaerben von polymeren des acrylnitrils

1985
- 1985-12-28 DE DE19853546294 patent/DE3546294A1/de not_active Withdrawn
1986
- 1986-12-19 EP EP86117722A patent/EP0228043A3/fr not_active Withdrawn
- 1986-12-23 DD DD86298296A patent/DD260077A5/de not_active IP Right Cessation
- 1986-12-23 US US06/945,761 patent/US4732573A/en not_active Expired - Fee Related
- 1986-12-25 JP JP61308073A patent/JPS62158765A/ja active Pending

Also Published As

Publication number	Publication date
DE3546294A1 (de)	1987-07-02
JPS62158765A (ja)	1987-07-14
EP0228043A2 (fr)	1987-07-08
US4732573A (en)	1988-03-22
EP0228043A3 (fr)	1990-06-06

Legal Events

Date	Code	Title	Description
1994-06-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE4128490A1 (de)	1993-03-04	Neue kationische thiazolazofarbstoffe
EP0044059B1 (fr)	1986-03-12	Procédé de teinture à l'état de gel d'articles fibreux en polymères d'acrylonitrile filés au mouillé
DE2945028A1 (de)	1981-05-21	Quartaere und basische azamethinverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel
DD260077A5 (de)	1988-09-14	Neue farbsalze, verfahren zu ihrer herstellung und ihre verwendung
DE2531445C3 (de)	1978-05-11	Sulfogruppenfreie wasserlösliche Azofarbstoffe und deren Verwendung zum Färben und/oder Bedrucken von synthetischen Textilfasern
DE2022624C3 (de)	1974-05-02	Basischer Disazofarbstoff, Verfahren zu dessen Herstellung und dessen Verwendung
EP0265828B1 (fr)	1990-08-08	Composés disazoiques solubles dans l'eau, leur procédé de préparation et leur utilisation comme colorants
EP0258806A1 (fr)	1988-03-09	Composés disazoiques solubles dans l'eau, leur procédé de préparation et leur emploi comme colorants
DE2039492A1 (de)	1972-02-10	Kationische Farbstoffe
DE1233520B (de)	1967-02-02	Verfahren zur Herstellung von basischen Hydrazonfarbstoffen
DE2013791B2 (de)	1977-08-25	Basische farbstoffe, verfahren zu deren herstellung und ihre verwendung zum faerben und bedrucken von textilmaterialien und leder, sowie zur herstellung von druckpasten und schreibfluessigkeiten
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DE1444715C (fr)
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DE1444728C (de)	1971-10-07	Disazodispersionsfarbstoffe und Ver fahren zur Herstellung von Disazodisper sionsfarbstoffen
DE1444728A1 (de)	1968-10-24	Disazo-Dispersionsfarbstoffe
DE1544600C (de)	1973-06-14	Monoazofarbstoffe sowie Ver fahren zu ihrer Herstellung und Verwendung
DE2159574A1 (de)	1972-06-15	Wasserunlösliche Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von hydrophoben Fasern
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DE2059096A1 (de)	1972-01-27	Neue kationische Farbstoffe und Verfahren zu deren Herstellung
DE2509095A1 (de)	1975-09-18	Azoverbindungen
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DE2441411A1 (de)	1975-03-06	Wasserloesliche kationische monoazofarbstoffe