JPS5821659B2 - 非対称型含クロム錯体染料の製造方法 - Google Patents
非対称型含クロム錯体染料の製造方法Info
- Publication number
- JPS5821659B2 JPS5821659B2 JP3776274A JP3776274A JPS5821659B2 JP S5821659 B2 JPS5821659 B2 JP S5821659B2 JP 3776274 A JP3776274 A JP 3776274A JP 3776274 A JP3776274 A JP 3776274A JP S5821659 B2 JPS5821659 B2 JP S5821659B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- chromium
- amino
- containing complex
- acid
- 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 20
- 229910052804 chromium Inorganic materials 0.000 title claims description 20
- 239000011651 chromium Substances 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 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 claims description 11
- -1 alkali metal salt Chemical class 0.000 claims description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 6
- 238000001465 metallisation Methods 0.000 claims description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 3
- 229960003080 taurine Drugs 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 239000000987 azo dye Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BPKYNJCZAGQUBB-UHFFFAOYSA-N 2-acetyl-5-methyl-4h-pyrazol-3-one Chemical compound CC(=O)N1N=C(C)CC1=O BPKYNJCZAGQUBB-UHFFFAOYSA-N 0.000 description 1
- KTHTXLUIEAIGCD-UHFFFAOYSA-N 2-amino-3,5-dichlorobenzoic acid Chemical compound NC1=C(Cl)C=C(Cl)C=C1C(O)=O KTHTXLUIEAIGCD-UHFFFAOYSA-N 0.000 description 1
- HZYQSYSKCJWFTC-UHFFFAOYSA-N 2-amino-3-chloro-5-sulfobenzoic acid Chemical compound ClC=1C(=C(C=C(C1)S(=O)(=O)O)C(=O)O)N HZYQSYSKCJWFTC-UHFFFAOYSA-N 0.000 description 1
- KGHGVBPOWNCREB-UHFFFAOYSA-N 2-amino-4-chloro-5-sulfobenzoic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1C(O)=O KGHGVBPOWNCREB-UHFFFAOYSA-N 0.000 description 1
- IGODHBBPXMXQCE-UHFFFAOYSA-N 2-amino-5-chloro-3-sulfobenzoic acid Chemical compound NC1=C(C(O)=O)C=C(Cl)C=C1S(O)(=O)=O IGODHBBPXMXQCE-UHFFFAOYSA-N 0.000 description 1
- HOHIAEPXOHCCGW-UHFFFAOYSA-N 2-aminoethanesulfonic acid Chemical compound NCCS(O)(=O)=O.NCCS(O)(=O)=O HOHIAEPXOHCCGW-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4h-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 description 1
- XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-amino-2-naphthoic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-M 3-oxo-3-phenylpropionate Chemical compound [O-]C(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-M 0.000 description 1
- GSOHXJQXAKNJES-UHFFFAOYSA-N 5-acetamido-2-aminobenzoic acid Chemical compound CC(=O)NC1=CC=C(N)C(C(O)=O)=C1 GSOHXJQXAKNJES-UHFFFAOYSA-N 0.000 description 1
- KPXVZOAGGSFZEX-UHFFFAOYSA-N 5-methyl-4-phenylpyrazol-3-one Chemical compound O=C1N=NC(C)=C1C1=CC=CC=C1 KPXVZOAGGSFZEX-UHFFFAOYSA-N 0.000 description 1
- NVKJOXRVEKMMHS-UHFFFAOYSA-N 5-nitro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)N=N1 NVKJOXRVEKMMHS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 150000003869 acetamides Chemical class 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical group CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-XPULMUKRSA-N acetyl acetate Chemical compound [14CH3]C(=O)OC([14CH3])=O WFDIJRYMOXRFFG-XPULMUKRSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical class O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7312053 | 1973-04-04 | ||
| FR7312053A FR2224527B1 (enrdf_load_stackoverflow) | 1973-04-04 | 1973-04-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS49130922A JPS49130922A (enrdf_load_stackoverflow) | 1974-12-16 |
| JPS5821659B2 true JPS5821659B2 (ja) | 1983-05-02 |
Family
ID=9117382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3776274A Expired JPS5821659B2 (ja) | 1973-04-04 | 1974-04-03 | 非対称型含クロム錯体染料の製造方法 |
Country Status (10)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2801035C2 (de) * | 1978-01-11 | 1984-08-16 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 1:2-Cr-Komplexfarbstoffen |
| CH642097A5 (de) * | 1979-05-02 | 1984-03-30 | Sandoz Ag | Metallkomplexe von azoverbindungen. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1012007B (de) * | 1953-06-08 | 1957-07-11 | Ciba Geigy | Verfahren zur Herstellung chromhaltiger Azofarbstoffe |
| FR1101955A (fr) * | 1953-06-08 | 1955-10-12 | Ciba Geigy | Colorants azoïques métallifères, leur préparation et leur emploi |
| FR1518833A (fr) * | 1967-02-10 | 1968-03-29 | Ugine Kuhlmann | Nouveaux complexes métallifères mixtes |
-
1973
- 1973-04-04 FR FR7312053A patent/FR2224527B1/fr not_active Expired
-
1974
- 1974-02-25 NL NL7402501A patent/NL176861C/xx not_active IP Right Cessation
- 1974-04-02 CH CH458574A patent/CH589127A5/xx not_active IP Right Cessation
- 1974-04-03 BR BR264674A patent/BR7402646D0/pt unknown
- 1974-04-03 CA CA196,762A patent/CA1022163A/en not_active Expired
- 1974-04-03 JP JP3776274A patent/JPS5821659B2/ja not_active Expired
- 1974-04-03 BE BE142816A patent/BE813258A/xx not_active IP Right Cessation
- 1974-04-03 GB GB1468974A patent/GB1423969A/en not_active Expired
- 1974-04-04 DE DE19742416342 patent/DE2416342C2/de not_active Expired
- 1974-04-04 IT IT6808074A patent/IT1011696B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2416342A1 (de) | 1974-10-24 |
| NL176861C (nl) | 1985-06-17 |
| BR7402646D0 (pt) | 1974-11-05 |
| IT1011696B (it) | 1977-02-10 |
| JPS49130922A (enrdf_load_stackoverflow) | 1974-12-16 |
| NL7402501A (enrdf_load_stackoverflow) | 1974-10-08 |
| FR2224527B1 (enrdf_load_stackoverflow) | 1976-09-10 |
| BE813258A (fr) | 1974-10-03 |
| FR2224527A1 (enrdf_load_stackoverflow) | 1974-10-31 |
| CH589127A5 (enrdf_load_stackoverflow) | 1977-06-30 |
| DE2416342C2 (de) | 1985-08-29 |
| CA1022163A (en) | 1977-12-06 |
| GB1423969A (en) | 1976-02-04 |
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