DE1958928A1 - Neue Disazofarbstoffpigmente und Verfahren zu deren Herstellung - Google Patents
Neue Disazofarbstoffpigmente und Verfahren zu deren HerstellungInfo
- Publication number
- DE1958928A1 DE1958928A1 DE19691958928 DE1958928A DE1958928A1 DE 1958928 A1 DE1958928 A1 DE 1958928A1 DE 19691958928 DE19691958928 DE 19691958928 DE 1958928 A DE1958928 A DE 1958928A DE 1958928 A1 DE1958928 A1 DE 1958928A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- alkoxy
- group
- alkyl
- radical
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 9
- -1 carboxylic acid halide Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000011368 organic material Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 230000000485 pigmenting effect Effects 0.000 claims 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 33
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 239000000975 dye Substances 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000987 azo dye Substances 0.000 description 6
- 229940044174 4-phenylenediamine Drugs 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NBUUUJWWOARGNW-UHFFFAOYSA-N 2-amino-5-methylbenzoic acid Chemical compound CC1=CC=C(N)C(C(O)=O)=C1 NBUUUJWWOARGNW-UHFFFAOYSA-N 0.000 description 3
- KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 description 3
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- FNJYNTJIZBHPGP-UHFFFAOYSA-N 2,5-dichlorobenzene-1,3-diamine Chemical compound NC1=CC(Cl)=CC(N)=C1Cl FNJYNTJIZBHPGP-UHFFFAOYSA-N 0.000 description 1
- QAYVHDDEMLNVMO-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C=C1Cl QAYVHDDEMLNVMO-UHFFFAOYSA-N 0.000 description 1
- FOVOBTLEKSQTFG-UHFFFAOYSA-N 2,5-dimethoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=C(OC)C=C1N FOVOBTLEKSQTFG-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- IPKHAOJAWZWURX-UHFFFAOYSA-N 2-amino-4,6-dichloro-n-phenylbenzamide Chemical compound NC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=CC=CC=C1 IPKHAOJAWZWURX-UHFFFAOYSA-N 0.000 description 1
- NQTLZJODEOHALT-UHFFFAOYSA-N 2-amino-4-(trifluoromethyl)benzoic acid Chemical compound NC1=CC(C(F)(F)F)=CC=C1C(O)=O NQTLZJODEOHALT-UHFFFAOYSA-N 0.000 description 1
- IWQRPSNYHYDWNI-UHFFFAOYSA-N 2-amino-4-chloro-n-phenylbenzamide Chemical compound NC1=CC(Cl)=CC=C1C(=O)NC1=CC=CC=C1 IWQRPSNYHYDWNI-UHFFFAOYSA-N 0.000 description 1
- QFELSXHMYYOYPG-UHFFFAOYSA-N 2-amino-5-bromo-n-phenylbenzamide Chemical compound NC1=CC=C(Br)C=C1C(=O)NC1=CC=CC=C1 QFELSXHMYYOYPG-UHFFFAOYSA-N 0.000 description 1
- GVKLEKQYSCBIDA-UHFFFAOYSA-N 2-amino-5-chloro-n-phenylbenzamide Chemical compound NC1=CC=C(Cl)C=C1C(=O)NC1=CC=CC=C1 GVKLEKQYSCBIDA-UHFFFAOYSA-N 0.000 description 1
- LHMDVTIZXLLZNN-UHFFFAOYSA-N 2-amino-5-methyl-n-phenylbenzamide Chemical compound CC1=CC=C(N)C(C(=O)NC=2C=CC=CC=2)=C1 LHMDVTIZXLLZNN-UHFFFAOYSA-N 0.000 description 1
- INKGKPCLQCFQKB-UHFFFAOYSA-N 2-amino-5-nitro-n-phenylbenzamide Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)NC1=CC=CC=C1 INKGKPCLQCFQKB-UHFFFAOYSA-N 0.000 description 1
- ORLUQBZQYSXPGK-UHFFFAOYSA-N 2-amino-n,5-dimethylbenzamide Chemical compound CNC(=O)C1=CC(C)=CC=C1N ORLUQBZQYSXPGK-UHFFFAOYSA-N 0.000 description 1
- FDPVTENMNDHFNK-UHFFFAOYSA-N 2-amino-n-phenylbenzamide Chemical compound NC1=CC=CC=C1C(=O)NC1=CC=CC=C1 FDPVTENMNDHFNK-UHFFFAOYSA-N 0.000 description 1
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 description 1
- NGULVTOQNLILMZ-UHFFFAOYSA-N 2-bromobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(Br)=C1 NGULVTOQNLILMZ-UHFFFAOYSA-N 0.000 description 1
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
- LQRIGLBCGDDYDR-UHFFFAOYSA-N 2-chloro-5-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=C(Cl)C=C1N LQRIGLBCGDDYDR-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- SSXPQLXWKPOYLJ-UHFFFAOYSA-N 4,6-dichlorobenzene-1,3-diamine Chemical compound NC1=CC(N)=C(Cl)C=C1Cl SSXPQLXWKPOYLJ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 description 1
- VVYWUQOTMZEJRJ-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1 VVYWUQOTMZEJRJ-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
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- 206010039587 Scarlet Fever Diseases 0.000 description 1
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- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
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- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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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
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
-
- 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
- C09B43/38—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 by reacting two or more ortho-hydroxy naphthoic acid dyes with polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Photoreceptors In Electrophotography (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1785568A CH508018A (de) | 1968-11-30 | 1968-11-30 | Verfahren zur Herstellung neuer Disazofarbstoffpigmente |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1958928A1 true DE1958928A1 (de) | 1970-09-17 |
Family
ID=4428591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691958928 Pending DE1958928A1 (de) | 1968-11-30 | 1969-11-24 | Neue Disazofarbstoffpigmente und Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE742363A (enrdf_load_stackoverflow) |
| CH (1) | CH508018A (enrdf_load_stackoverflow) |
| CS (1) | CS154648B2 (enrdf_load_stackoverflow) |
| DE (1) | DE1958928A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2024963B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1256260A (enrdf_load_stackoverflow) |
| NL (1) | NL6917938A (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1309702A (fr) * | 1961-01-13 | 1962-11-16 | Ciba Geigy | Nouveaux colorants du type carbamido-azoïque et procédé pour les préparer |
| CH488786A (de) * | 1967-07-11 | 1970-04-15 | Geigy Ag J R | Verfahren zur Herstellung von Disazopigmenten |
-
1968
- 1968-11-30 CH CH1785568A patent/CH508018A/de not_active IP Right Cessation
-
1969
- 1969-11-12 FR FR6938655A patent/FR2024963B1/fr not_active Expired
- 1969-11-24 DE DE19691958928 patent/DE1958928A1/de active Pending
- 1969-11-24 CS CS772869A patent/CS154648B2/cs unknown
- 1969-11-26 GB GB5793369A patent/GB1256260A/en not_active Expired
- 1969-11-28 NL NL6917938A patent/NL6917938A/xx unknown
- 1969-11-28 BE BE742363D patent/BE742363A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2024963B1 (enrdf_load_stackoverflow) | 1974-08-09 |
| NL6917938A (enrdf_load_stackoverflow) | 1970-06-02 |
| FR2024963A1 (enrdf_load_stackoverflow) | 1970-09-04 |
| BE742363A (enrdf_load_stackoverflow) | 1970-05-28 |
| CH508018A (de) | 1971-05-31 |
| GB1256260A (en) | 1971-12-08 |
| CS154648B2 (enrdf_load_stackoverflow) | 1974-04-30 |
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