CH523958A - Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen - Google Patents
Verfahren zur Herstellung in Wasser schwer löslicher AzoverbindungenInfo
- Publication number
- CH523958A CH523958A CH635370A CH635370A CH523958A CH 523958 A CH523958 A CH 523958A CH 635370 A CH635370 A CH 635370A CH 635370 A CH635370 A CH 635370A CH 523958 A CH523958 A CH 523958A
- Authority
- CH
- Switzerland
- Prior art keywords
- red
- formula
- oco
- dyes
- alkyl
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title abstract 2
- 239000000463 material Substances 0.000 title description 4
- 230000002209 hydrophobic effect Effects 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 32
- -1 aryloxy radical Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 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
- 238000004519 manufacturing process Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- VHPMGVXTLGJECO-UHFFFAOYSA-N [Rh]C#N Chemical compound [Rh]C#N VHPMGVXTLGJECO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 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
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH635370A CH523958A (de) | 1969-04-02 | 1969-04-02 | Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH635370A CH523958A (de) | 1969-04-02 | 1969-04-02 | Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen |
| CH504369A CH523949A (de) | 1969-04-02 | 1969-04-02 | Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH523958A true CH523958A (de) | 1972-06-15 |
Family
ID=4286981
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH635370A CH523958A (de) | 1969-04-02 | 1969-04-02 | Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen |
| CH504369A CH523949A (de) | 1969-04-02 | 1969-04-02 | Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH504369A CH523949A (de) | 1969-04-02 | 1969-04-02 | Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63128945U (enrdf_load_html_response) * | 1987-02-16 | 1988-08-23 | ||
| US5550218A (en) * | 1990-07-11 | 1996-08-27 | Sandoz Ltd. | Azo compounds having unsubstituted or substituted 2-phenoxycarbonylethyl groups |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE636010A (enrdf_load_html_response) * | 1963-08-09 | |||
| BE636011A (enrdf_load_html_response) * | 1963-08-09 | |||
| DE1644369A1 (de) * | 1966-03-11 | 1971-03-25 | Sandoz Ag | Verfahren zur Herstellung von Monoazofarbstoffen |
| FR1539436A (fr) * | 1966-10-06 | 1968-09-13 | Sandoz Sa | Colorants mono-azoïques, leur procédé de fabrication et leurs applications |
-
1969
- 1969-04-02 CH CH635370A patent/CH523958A/de not_active IP Right Cessation
- 1969-04-02 CH CH504369A patent/CH523949A/de not_active IP Right Cessation
-
1970
- 1970-02-12 CY CY84270A patent/CY842A/xx unknown
- 1970-02-12 GB GB687070A patent/GB1298765A/en not_active Expired
- 1970-02-12 GB GB1294978D patent/GB1294978A/en not_active Expired
- 1970-03-24 NL NL7004216A patent/NL162953C/xx not_active IP Right Cessation
- 1970-03-24 NL NL7004158A patent/NL7004158A/xx unknown
- 1970-03-30 JP JP2605270A patent/JPS5234649B1/ja active Pending
- 1970-03-30 JP JP2605370A patent/JPS5249015B1/ja active Pending
- 1970-03-31 BE BE748269D patent/BE748269A/xx unknown
- 1970-03-31 DE DE19702015350 patent/DE2015350C3/de not_active Expired
- 1970-03-31 ES ES378074A patent/ES378074A1/es not_active Expired
- 1970-03-31 ES ES378073A patent/ES378073A1/es not_active Expired
- 1970-03-31 BE BE748268D patent/BE748268A/xx not_active IP Right Cessation
- 1970-04-01 BR BR21789670A patent/BR7017896D0/pt unknown
- 1970-04-01 BR BR21789770A patent/BR7017897D0/pt unknown
- 1970-04-01 FR FR7011693A patent/FR2038164A1/fr not_active Withdrawn
- 1970-04-01 FR FR7011694A patent/FR2038165B1/fr not_active Expired
- 1970-06-04 ES ES380399A patent/ES380399A1/es not_active Expired
-
1976
- 1976-02-13 KE KE260176A patent/KE2601A/xx unknown
- 1976-05-13 HK HK28376A patent/HK28376A/xx unknown
- 1976-12-30 MY MY7600103A patent/MY7600103A/xx unknown
-
1977
- 1977-08-09 JP JP9548077A patent/JPS5429534B1/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |