DE3017935C2 - 1,1'-Binaphthyl-4,4',5,5',8,8'-hexacarbonsäurederivate - Google Patents
1,1'-Binaphthyl-4,4',5,5',8,8'-hexacarbonsäurederivateInfo
- Publication number
- DE3017935C2 DE3017935C2 DE3017935A DE3017935A DE3017935C2 DE 3017935 C2 DE3017935 C2 DE 3017935C2 DE 3017935 A DE3017935 A DE 3017935A DE 3017935 A DE3017935 A DE 3017935A DE 3017935 C2 DE3017935 C2 DE 3017935C2
- Authority
- DE
- Germany
- Prior art keywords
- binaphthyl
- deep
- hexacarboxylic acid
- acid
- hexacarboxylic
- 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.)
- Expired
Links
- IJFYKLVYKPCCLM-UHFFFAOYSA-N 8-(4,5,8-tricarboxynaphthalen-1-yl)naphthalene-1,4,5-tricarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C3=C4C(C(O)=O)=CC=C(C4=C(C(O)=O)C=C3)C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O IJFYKLVYKPCCLM-UHFFFAOYSA-N 0.000 title abstract description 6
- -1 2,4-dimethylphenyl Chemical group 0.000 claims description 10
- 150000003949 imides Chemical class 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 239000004753 textile Substances 0.000 abstract description 16
- 238000004043 dyeing Methods 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical class C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052736 halogen Inorganic materials 0.000 abstract description 7
- 150000002367 halogens Chemical class 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HCBLQWRZGRKVFU-UHFFFAOYSA-N 1h-benzimidazole;8-(4,5,8-tricarboxynaphthalen-1-yl)naphthalene-1,4,5-tricarboxylic acid Chemical compound C1=CC=C2NC=NC2=C1.C1=CC(C(O)=O)=C2C(C3=C4C(C(O)=O)=CC=C(C4=C(C(O)=O)C=C3)C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O HCBLQWRZGRKVFU-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000984 vat dye Substances 0.000 description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 244000172533 Viola sororia Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- WIHHVKUARKTSBU-UHFFFAOYSA-N 4-bromobenzene-1,2-diamine Chemical compound NC1=CC=C(Br)C=C1N WIHHVKUARKTSBU-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- ROJMDQBRKBPHIU-UHFFFAOYSA-N 4-ethylbenzene-1,2-diamine Chemical compound CCC1=CC=C(N)C(N)=C1 ROJMDQBRKBPHIU-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- XUSDWZAXWXOCCJ-UHFFFAOYSA-N 9-bromononacyclo[18.10.2.22,5.03,16.04,13.06,11.017,31.021,26.028,32]tetratriaconta-1(30),2,4,6(11),7,9,13,15,17(31),18,20(32),21,23,25,28,33-hexadecaene-12,27-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=C(Br)C=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 XUSDWZAXWXOCCJ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino 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
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002395 hexacarboxylic acids Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- KOTVVDDZWMCZBT-UHFFFAOYSA-N vat violet 1 Chemical compound C1=CC=C[C]2C(=O)C(C=CC3=C4C=C(C=5C=6C(C([C]7C=CC=CC7=5)=O)=CC=C5C4=6)Cl)=C4C3=C5C=C(Cl)C4=C21 KOTVVDDZWMCZBT-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
-
- 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
- D06P1/0048—Converting dyes in situ in a non-appropriate form by hydrolysis, saponification, reduction with split-off of a substituent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU792763662A SU1038342A1 (ru) | 1979-05-10 | 1979-05-10 | Ангидриды монобензимидазольных производных 1,1-бинафтил-4,4,5,5,8,8-гексакарбоновых кислот как промежуточные продукты дл синтеза красителей |
| SU792769537A SU919342A1 (ru) | 1979-05-18 | 1979-05-18 | Производные 1,1-бинафтил-4,4,5,5,8,8-гексакарбоновой кислоты в качестве красителей дл хлопчатобумажных,льн ных и вискозных материалов и способ их получени |
| SU792850601A SU1036731A1 (ru) | 1979-12-24 | 1979-12-24 | Производные 3,4,9,10-перилентетракарбоновой кислоты дл крашени целлюлозных волокон |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3017935A1 DE3017935A1 (de) | 1980-11-20 |
| DE3017935C2 true DE3017935C2 (de) | 1986-11-27 |
Family
ID=27356354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3017935A Expired DE3017935C2 (de) | 1979-05-10 | 1980-05-09 | 1,1'-Binaphthyl-4,4',5,5',8,8'-hexacarbonsäurederivate |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH655824GA3 (en, 2012) |
| DE (1) | DE3017935C2 (en, 2012) |
| FR (1) | FR2456102A1 (en, 2012) |
| GB (1) | GB2051110B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3309060A1 (de) * | 1983-03-14 | 1984-09-20 | Hoechst Ag, 6230 Frankfurt | Perylen-3,4,9,10-tetracarbonsaeure-monoanhydrid-monoimid- und -monoimidazolid-verbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DE59407520D1 (de) * | 1993-08-13 | 1999-02-04 | Ciba Geigy Ag | Perylenamidinimid-Farbstoffe, ein Verfahren zu deren Herstellung und deren Verwendung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH363151A (de) * | 1957-10-29 | 1962-07-15 | Sandoz Ag | Verwendung von Perylenpigmentfarbstoffen zum Färben |
| SU366705A1 (ru) * | 1971-04-28 | 1974-01-05 | Способ получения производных 1,1'-динафтил-4,4', 5,5', 8,8' - гексакарбоновой кислоты12 | |
| US3920387A (en) * | 1972-04-24 | 1975-11-18 | Nikolai Stepanovich Dokunikhin | Dinaphthyl derivatives, method of producing same and application thereof |
| US3922142A (en) * | 1972-04-24 | 1975-11-25 | Nikolai Stepanovich Dokunikhin | Method of printing textiles with derivatives of 1,1{40 -dinaphthyl-4,4{40 ,5,5{40 ,8,8{40 -hexacarboxylic acid |
-
1980
- 1980-05-08 FR FR8010240A patent/FR2456102A1/fr active Granted
- 1980-05-09 CH CH364480A patent/CH655824GA3/de unknown
- 1980-05-09 DE DE3017935A patent/DE3017935C2/de not_active Expired
- 1980-05-12 GB GB8015596A patent/GB2051110B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH655824GA3 (en, 2012) | 1986-05-30 |
| GB2051110B (en) | 1983-08-03 |
| FR2456102A1 (fr) | 1980-12-05 |
| GB2051110A (en) | 1981-01-14 |
| FR2456102B1 (en, 2012) | 1983-08-12 |
| DE3017935A1 (de) | 1980-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE939044C (de) | Verfahren zur Herstellung von 1, 4-Diamino-2, 3-anthrachinon-dicarbonsaeureimiden | |
| DE2040872C3 (de) | Hydrazonfarbstoffe | |
| CH661275A5 (de) | Methin-azo-verbindungen. | |
| DE1150652B (de) | Faerben von Polyacrylnitrilfasern | |
| US4336383A (en) | 1-1-Binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid compounds, method of preparation and use thereof for the synthesis of asymmetric derivatives of 3,4,9,10-perylenetetracarboxylic acid, and for dyeing and printing of textile materials | |
| DE3017935C2 (de) | 1,1'-Binaphthyl-4,4',5,5',8,8'-hexacarbonsäurederivate | |
| DE1156527B (de) | Verfahren zur Herstellung von Anthrachinonkuepenfarbstoffen | |
| DE2351296C3 (de) | Kationische Farbstoffe, deren Herstellung und deren Verwendung | |
| EP0065743B1 (de) | Neue Cumarinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe | |
| DE2220744C3 (de) | Derivate der l,l'-Dinaphthyl-4,4', 5,5',8,8'-hexacarbonsäure, Verfahren zu deren Herstellung und ihre Verwendung | |
| DE2029793C3 (de) | Anthrachinondispersionsfarbstoffe und Verfahren zu deren Herstellung | |
| DE2241259C3 (de) | 1,2,4-Benzotriazinuin-Farbstoffe, Verfahren zu ihrer Herstellung und Verfahren zum Färben und Bedrucken | |
| DE3051031C2 (de) | Verfahren zum faerben und bedrucken von textilien | |
| DE652773C (de) | Verfahren zur Herstellung von Kuepenfarbstoffen der Anthrachinonacridonreihe | |
| US2412817A (en) | Aminophthalimides | |
| DE1170569B (de) | Verfahren zur Herstellung von Farbstoffen | |
| DE836689C (de) | Verfahren zur Herstellung von Kuepenfarbstoffen | |
| DE931845C (de) | Verfahren zur Herstellung von Kuepenfarbstoffen | |
| DE2607869A1 (de) | Verfahren zum faerben von hydrophoben textilfasern, hierfuer geeignete neue farbstoffe und verfahren zu deren herstellung | |
| CH624980A5 (en, 2012) | ||
| DE1644252C (de) | In Wasser schwerlösliche Farbstoffe der Anthrachinon Azoreihe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1569606A1 (de) | Basische Farbstoffe | |
| DE1569713C (de) | Kationische Farbstoffe und ihre Herstellung | |
| DE1569775B1 (de) | Verfahren zur Herstellung von Nitrofarbstoffen der Acridonreihe | |
| DE2040653C3 (de) | Methinfarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben von bestimmten Polymerisaten, Mischpolymerisaten, Leder, tannierter Baumwolle, Druckpasten und ligninhaltigen Fasern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAR | Request for search filed | ||
| OC | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS |
|
| 8172 | Supplementary division/partition in: |
Ref country code: DE Ref document number: 3051031 Format of ref document f/p: P |
|
| Q171 | Divided out to: |
Ref country code: DE Ref document number: 3051031 |
|
| D2 | Grant after examination | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: VOROSCOV, GEORGIJ NIKOLAEVIC MASANOVA, NATALIJA NI |
|
| 8381 | Inventor (new situation) |
Free format text: VOROSCOV, GEORGIJ NIKOLAEVIC MASANOVA, NATALIJA NIKOLAEVNA FELDBLJUM, NIKOLAJ BORISOVIC, MOSKAU/MOSKVA, SU ALEKSEEV, VASILIJ IVANOVIC SIGALEVSKIJ, VADIM ALEKSEEVIC SOLOMATIN, GEORGIJ GEORGIEVIC SULEPOVA, OL GA IGOREVNA, RUBEZNOE, SU CHAITUN, GEB. ZEZIKOVA, GALINA GEORGIEVNA, MOSKAU/MOSKVA, (VERSTORBEN), SU GORDEEVA, GEB. CERNJAVAJA, NADEZDA VLADIMIROVNA, MOSKAU/MOSKVA, SU |
|
| 8364 | No opposition during term of opposition | ||
| AH | Division in |
Ref country code: DE Ref document number: 3051031 Format of ref document f/p: P |
|
| 8339 | Ceased/non-payment of the annual fee |