CA1133473A - Organic compounds - Google Patents
Organic compoundsInfo
- Publication number
- CA1133473A CA1133473A CA344,554A CA344554A CA1133473A CA 1133473 A CA1133473 A CA 1133473A CA 344554 A CA344554 A CA 344554A CA 1133473 A CA1133473 A CA 1133473A
- Authority
- CA
- Canada
- Prior art keywords
- alkoxy
- alkyl
- chlorine
- bromine
- phenyl
- 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
- 150000002894 organic compounds Chemical class 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims abstract description 51
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 30
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005394 methallyl group Chemical group 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006515 benzyloxy alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 abstract description 2
- 239000000986 disperse dye Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- PJQFZPWSFDVYIF-UHFFFAOYSA-N 5-amino-3-methyl-1,2-thiazole-4-carbonitrile Chemical compound CC1=NSC(N)=C1C#N PJQFZPWSFDVYIF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
-
- 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
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH88879A CH638549A5 (de) | 1979-01-30 | 1979-01-30 | Azoverbindungen. |
| CH888/79 | 1979-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1133473A true CA1133473A (en) | 1982-10-12 |
Family
ID=4197515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA344,554A Expired CA1133473A (en) | 1979-01-30 | 1980-01-28 | Organic compounds |
Country Status (10)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3016301A1 (de) * | 1980-04-28 | 1981-10-29 | Cassella Ag, 6000 Frankfurt | Wasserunloesliche azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| DE3036576A1 (de) | 1980-09-27 | 1982-05-19 | Cassella Ag, 6000 Frankfurt | Wasserunloeslicher azofarbstoff, verfahren zu seiner herstellung und seine verwendung |
| DE3205435A1 (de) * | 1982-02-16 | 1983-08-25 | Basf Ag, 6700 Ludwigshafen | Isothiazolazofarbstoffe |
| DE3207209A1 (de) * | 1982-02-27 | 1983-09-08 | Basf Ag, 6700 Ludwigshafen | Isothiazolazofarbstoffe |
| DE3400364A1 (de) * | 1984-01-07 | 1985-07-18 | Basf Ag, 6700 Ludwigshafen | Isothiazolazofarbstoffe |
| JPS60155269A (ja) * | 1984-01-24 | 1985-08-15 | Sumitomo Chem Co Ltd | イソチアゾ−ルアゾ染料 |
| DE3409243A1 (de) * | 1984-03-14 | 1985-09-19 | Basf Ag, 6700 Ludwigshafen | Isothiazolazofarbstoffe |
| DE3816698A1 (de) * | 1988-05-17 | 1989-11-30 | Basf Ag | Azofarbstoffe der 5-aminoisothiazolreihe |
| KR100711762B1 (ko) * | 2005-07-15 | 2007-04-30 | 주식회사 포스코 | 미분 원료 조립용 펠렛타이저 |
-
1979
- 1979-01-30 CH CH88879A patent/CH638549A5/de not_active IP Right Cessation
-
1980
- 1980-01-21 DE DE19803001945 patent/DE3001945A1/de not_active Withdrawn
- 1980-01-25 GB GB8002572A patent/GB2041391B/en not_active Expired
- 1980-01-28 IT IT8047723A patent/IT8047723A0/it unknown
- 1980-01-28 CA CA344,554A patent/CA1133473A/en not_active Expired
- 1980-01-29 FR FR8001849A patent/FR2447954A1/fr active Granted
- 1980-01-29 JP JP841980A patent/JPS55102655A/ja active Pending
- 1980-01-29 KR KR1019800000319A patent/KR830001915A/ko not_active Ceased
- 1980-01-29 BR BR8000554A patent/BR8000554A/pt unknown
- 1980-01-30 ES ES488376A patent/ES8101637A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55102655A (en) | 1980-08-06 |
| GB2041391B (en) | 1982-11-17 |
| ES488376A0 (es) | 1980-12-16 |
| BR8000554A (pt) | 1980-10-21 |
| GB2041391A (en) | 1980-09-10 |
| KR830001915A (ko) | 1983-05-19 |
| DE3001945A1 (de) | 1980-08-07 |
| IT8047723A0 (it) | 1980-01-28 |
| CH638549A5 (de) | 1983-09-30 |
| ES8101637A1 (es) | 1980-12-16 |
| FR2447954B1 (enrdf_load_stackoverflow) | 1983-11-25 |
| FR2447954A1 (fr) | 1980-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |