DE2059677C3 - Azopigmente der beta-Hydroxynaphthoesäurereihe, Verfahren zu deren Herstellung und ihre Verwendung - Google Patents
Azopigmente der beta-Hydroxynaphthoesäurereihe, Verfahren zu deren Herstellung und ihre VerwendungInfo
- Publication number
- DE2059677C3 DE2059677C3 DE2059677A DE2059677A DE2059677C3 DE 2059677 C3 DE2059677 C3 DE 2059677C3 DE 2059677 A DE2059677 A DE 2059677A DE 2059677 A DE2059677 A DE 2059677A DE 2059677 C3 DE2059677 C3 DE 2059677C3
- Authority
- DE
- Germany
- Prior art keywords
- nhoc
- methyl
- chlorine
- methoxy
- formula
- 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
- 239000000049 pigment Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- -1 Methoxy, cyano, carbomethoxy Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000005521 carbonamide group Chemical group 0.000 claims description 8
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims description 2
- JVRHADZWRWBICE-UHFFFAOYSA-N O=S(=O)NC1=CC=CC=C1 Chemical compound O=S(=O)NC1=CC=CC=C1 JVRHADZWRWBICE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 13
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000007639 printing Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000008096 xylene Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 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 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- NOWRLNPOENZFHP-ARHDFHRDSA-N 1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hexan-2-yl]thymine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H]2C[C@@]2(CO)[C@@H](O)C1 NOWRLNPOENZFHP-ARHDFHRDSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- RLCZBUOZNFAZLK-UHFFFAOYSA-N 3-hydroxynaphthalene-2-carbonyl chloride Chemical compound C1=CC=C2C=C(C(Cl)=O)C(O)=CC2=C1 RLCZBUOZNFAZLK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical group O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2059677A DE2059677C3 (de) | 1970-12-04 | 1970-12-04 | Azopigmente der beta-Hydroxynaphthoesäurereihe, Verfahren zu deren Herstellung und ihre Verwendung |
| CH1735171A CH574482A5 (enExample) | 1970-12-04 | 1971-11-29 | |
| CH151675A CH584740A5 (enExample) | 1970-12-04 | 1971-11-29 | |
| IT54432/71A IT945205B (it) | 1970-12-04 | 1971-11-30 | Pigmenti azoici della serie dell acido beta idrossi naftoico |
| FR7142920A FR2116434B1 (enExample) | 1970-12-04 | 1971-11-30 | |
| NL7116527A NL7116527A (enExample) | 1970-12-04 | 1971-12-01 | |
| US00204310A US3821191A (en) | 1970-12-04 | 1971-12-02 | Azo pigments of the aminoanthraquinonylazo-hydroxynaphthoic acid series |
| BR8047/71A BR7108047D0 (pt) | 1970-12-04 | 1971-12-03 | Processo para a fabricacao de corantes pigmentares azoicos da serie do acido beta-hidroxinaftoico |
| GB5617671A GB1362809A (en) | 1970-12-04 | 1971-12-03 | Azo pigments of the beta-hydroxynaphthoic acid arylamide series |
| BE776214A BE776214A (fr) | 1970-12-04 | 1971-12-03 | Pigments azoiques derives de l'acide 3-hydroxy-2-naphtoique |
| JP46097610A JPS5021493B1 (enExample) | 1970-12-04 | 1971-12-04 | |
| JP49139664A JPS5088126A (enExample) | 1970-12-04 | 1974-12-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2059677A DE2059677C3 (de) | 1970-12-04 | 1970-12-04 | Azopigmente der beta-Hydroxynaphthoesäurereihe, Verfahren zu deren Herstellung und ihre Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2059677A1 DE2059677A1 (de) | 1972-06-08 |
| DE2059677B2 DE2059677B2 (de) | 1975-03-06 |
| DE2059677C3 true DE2059677C3 (de) | 1975-10-16 |
Family
ID=5789968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2059677A Expired DE2059677C3 (de) | 1970-12-04 | 1970-12-04 | Azopigmente der beta-Hydroxynaphthoesäurereihe, Verfahren zu deren Herstellung und ihre Verwendung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3821191A (enExample) |
| JP (2) | JPS5021493B1 (enExample) |
| BE (1) | BE776214A (enExample) |
| BR (1) | BR7108047D0 (enExample) |
| CH (2) | CH574482A5 (enExample) |
| DE (1) | DE2059677C3 (enExample) |
| FR (1) | FR2116434B1 (enExample) |
| GB (1) | GB1362809A (enExample) |
| IT (1) | IT945205B (enExample) |
| NL (1) | NL7116527A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0881267B1 (en) * | 1996-10-11 | 2004-04-28 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Azo compounds and process for preparing the same |
| ATE328965T1 (de) * | 1998-10-16 | 2006-06-15 | Ueno Seiyaku Oyo Kenkyujo Kk | Azoverbindungen sowie verfahren zur herstellung derselben |
-
1970
- 1970-12-04 DE DE2059677A patent/DE2059677C3/de not_active Expired
-
1971
- 1971-11-29 CH CH1735171A patent/CH574482A5/xx not_active IP Right Cessation
- 1971-11-29 CH CH151675A patent/CH584740A5/xx not_active IP Right Cessation
- 1971-11-30 FR FR7142920A patent/FR2116434B1/fr not_active Expired
- 1971-11-30 IT IT54432/71A patent/IT945205B/it active
- 1971-12-01 NL NL7116527A patent/NL7116527A/xx unknown
- 1971-12-02 US US00204310A patent/US3821191A/en not_active Expired - Lifetime
- 1971-12-03 GB GB5617671A patent/GB1362809A/en not_active Expired
- 1971-12-03 BE BE776214A patent/BE776214A/xx unknown
- 1971-12-03 BR BR8047/71A patent/BR7108047D0/pt unknown
- 1971-12-04 JP JP46097610A patent/JPS5021493B1/ja active Pending
-
1974
- 1974-12-06 JP JP49139664A patent/JPS5088126A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2059677B2 (de) | 1975-03-06 |
| BR7108047D0 (pt) | 1973-05-03 |
| GB1362809A (en) | 1974-08-07 |
| DE2059677A1 (de) | 1972-06-08 |
| FR2116434A1 (enExample) | 1972-07-13 |
| FR2116434B1 (enExample) | 1975-12-26 |
| JPS5021493B1 (enExample) | 1975-07-23 |
| CH574482A5 (enExample) | 1976-04-15 |
| US3821191A (en) | 1974-06-28 |
| NL7116527A (enExample) | 1972-06-06 |
| JPS5088126A (enExample) | 1975-07-15 |
| IT945205B (it) | 1973-05-10 |
| BE776214A (fr) | 1972-06-05 |
| CH584740A5 (enExample) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8330 | Complete renunciation |