CH470410A - Verfahren zur Herstellung von Benzoxazolderivaten und Verwendung derselben - Google Patents
Verfahren zur Herstellung von Benzoxazolderivaten und Verwendung derselbenInfo
- Publication number
- CH470410A CH470410A CH1616865A CH1616865A CH470410A CH 470410 A CH470410 A CH 470410A CH 1616865 A CH1616865 A CH 1616865A CH 1616865 A CH1616865 A CH 1616865A CH 470410 A CH470410 A CH 470410A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- compounds
- cyanstyryl
- amino
- benzoxazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- JEWPACUDYNBTSN-ZETCQYMHSA-N (2s)-2-hydroxyheptanenitrile Chemical compound CCCCC[C@H](O)C#N JEWPACUDYNBTSN-ZETCQYMHSA-N 0.000 claims description 2
- 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 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- MWFMCZWMLLCBJH-UHFFFAOYSA-N o-naphthalen-1-ylhydroxylamine Chemical compound C1=CC=C2C(ON)=CC=CC2=C1 MWFMCZWMLLCBJH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- DAYPQGQLFQVFPV-UHFFFAOYSA-N 3-(2-fluorophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid Chemical compound O1C(C(=O)O)CC(C=2C(=CC=CC=2)F)=N1 DAYPQGQLFQVFPV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 methoxy, ethoxy Chemical group 0.000 description 10
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VIRORPOMNGCYLX-UHFFFAOYSA-N 3-(4-cyanophenyl)prop-2-enamide Chemical compound NC(=O)C=CC1=CC=C(C#N)C=C1 VIRORPOMNGCYLX-UHFFFAOYSA-N 0.000 description 3
- XQJQKADNDFGUPY-UHFFFAOYSA-N 5,7-dimethyl-1,3-benzoxazole Chemical compound CC1=CC(C)=C2OC=NC2=C1 XQJQKADNDFGUPY-UHFFFAOYSA-N 0.000 description 3
- CWNRDOFXKWOGKW-UHFFFAOYSA-N 5-chloro-6-methyl-1,3-benzoxazole Chemical compound C1=C(Cl)C(C)=CC2=C1N=CO2 CWNRDOFXKWOGKW-UHFFFAOYSA-N 0.000 description 3
- NIFNXGHHDAXUGO-UHFFFAOYSA-N 5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC=NC2=CC=1C1=CC=CC=C1 NIFNXGHHDAXUGO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 2
- VWMQXAYLHOSRKA-UHFFFAOYSA-N 5-chloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC=NC2=C1 VWMQXAYLHOSRKA-UHFFFAOYSA-N 0.000 description 2
- UBIAVBGIRDRQLD-UHFFFAOYSA-N 5-methyl-1,3-benzoxazole Chemical compound CC1=CC=C2OC=NC2=C1 UBIAVBGIRDRQLD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HQVOPXGNHGTKOD-AATRIKPKSA-N (e)-3-(2-cyanophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1C#N HQVOPXGNHGTKOD-AATRIKPKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- WOGITNXCNOTRLK-UHFFFAOYSA-N 3-phenylprop-2-enoyl chloride Chemical class ClC(=O)C=CC1=CC=CC=C1 WOGITNXCNOTRLK-UHFFFAOYSA-N 0.000 description 1
- RWNMLYACWNIEIG-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzoxazole Chemical compound C1=C(C)C(C)=CC2=C1OC=N2 RWNMLYACWNIEIG-UHFFFAOYSA-N 0.000 description 1
- MXJGWNPVKBVVTM-UHFFFAOYSA-N 5-tert-butyl-1,3-benzoxazole Chemical compound CC(C)(C)C1=CC=C2OC=NC2=C1 MXJGWNPVKBVVTM-UHFFFAOYSA-N 0.000 description 1
- JEMHCGAIQBUYDF-UHFFFAOYSA-N 7-methyl-1,3-benzoxazole Chemical compound CC1=CC=CC2=C1OC=N2 JEMHCGAIQBUYDF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 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
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/614—Optical bleaching or brightening in aqueous solvents
- D06L4/636—Optical bleaching or brightening in aqueous solvents with disperse brighteners
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0037032 | 1962-06-09 | ||
| CH718763A CH441213A (de) | 1962-06-09 | 1963-06-07 | Verwendung von Benzoxazolverbindungen als optische Aufhellungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH470410A true CH470410A (de) | 1969-03-31 |
Family
ID=7096710
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1616865A CH470410A (de) | 1962-06-09 | 1963-06-07 | Verfahren zur Herstellung von Benzoxazolderivaten und Verwendung derselben |
| CH718763A CH441213A (de) | 1962-06-09 | 1963-06-07 | Verwendung von Benzoxazolverbindungen als optische Aufhellungsmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH718763A CH441213A (de) | 1962-06-09 | 1963-06-07 | Verwendung von Benzoxazolverbindungen als optische Aufhellungsmittel |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US3530119A (en:Method) |
| BE (1) | BE633434A (en:Method) |
| CH (2) | CH470410A (en:Method) |
| DE (1) | DE1419330A1 (en:Method) |
| DK (1) | DK103507C (en:Method) |
| GB (2) | GB1055184A (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1419330A1 (de) * | 1962-06-09 | 1970-02-19 | Hoechst Ag | Optische Aufhellungsmittel |
| CH514616A (de) * | 1968-10-07 | 1971-10-31 | Ciba Geigy Ag | Verfahren zur Herstellung von Arylenoxazolen |
| DE2349480A1 (de) * | 1973-10-02 | 1975-04-10 | Bayer Ag | Optische aufhellungsmittel |
| US3873531A (en) * | 1974-03-29 | 1975-03-25 | Eastman Kodak Co | 2{55 P-{8 2-(2-benzoxazolyl)vinyl{9 phenyl{56 oxazolo{8 5,4-b{9 pyridine fluorescent whitening agents |
| CA1075701A (en) * | 1975-08-28 | 1980-04-15 | Harold M. Pitt | Production of n-substituted oxazolidines |
| TW470818B (en) * | 2000-05-18 | 2002-01-01 | Thk Co Ltd | Spherical bearing and method for manufacturing the same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2842545A (en) * | 1958-07-08 | Process for the manufacture of | ||
| CA578303A (en) * | 1959-06-23 | Ackermann Franz | Process for the optical brightening of polyacrylonitrile fibers | |
| US3118883A (en) * | 1964-01-21 | Chi-chj | ||
| CH348967A (de) * | 1956-12-21 | 1960-09-30 | Geigy Ag J R | Verfahren zur Herstellung von Benzimidazolen |
| DE1088456B (de) * | 1959-02-03 | 1960-09-08 | Glanzstoff Ag | Verfahren zur Erzielung eines dauerhaften, licht- und wasch-bestaendigen Aufhellungseffektes bei Textilien aus Polyamid, das aus Caprolactam erzeugt wurde |
| GB967483A (en:Method) * | 1961-09-12 | |||
| DE1419330A1 (de) * | 1962-06-09 | 1970-02-19 | Hoechst Ag | Optische Aufhellungsmittel |
| US3158610A (en) * | 1964-01-03 | 1964-11-24 | American Cyanamid Co | 2-styrylbenzoxazole brighteners |
-
1962
- 1962-06-09 DE DE19621419330 patent/DE1419330A1/de not_active Withdrawn
-
1963
- 1963-06-06 GB GB25024/66A patent/GB1055184A/en not_active Expired
- 1963-06-06 GB GB22571/63A patent/GB1055183A/en not_active Expired
- 1963-06-07 CH CH1616865A patent/CH470410A/de not_active IP Right Cessation
- 1963-06-07 CH CH718763A patent/CH441213A/de unknown
- 1963-06-07 DK DK271563AA patent/DK103507C/da active
- 1963-06-07 US US286164A patent/US3530119A/en not_active Expired - Lifetime
- 1963-06-10 BE BE633434A patent/BE633434A/fr unknown
-
1965
- 1965-10-13 US US495703A patent/US3427307A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK103507C (da) | 1966-01-17 |
| GB1055183A (en) | 1967-01-18 |
| BE633434A (fr) | 1963-12-10 |
| US3427307A (en) | 1969-02-11 |
| DE1419330A1 (de) | 1970-02-19 |
| US3530119A (en) | 1970-09-22 |
| CH718763A4 (en:Method) | 1967-04-29 |
| CH441213A (de) | 1968-01-15 |
| GB1055184A (en) | 1967-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |