CA1037969A - Process for the manufacture of cyano-substituted bis-styryl compounds - Google Patents
Process for the manufacture of cyano-substituted bis-styryl compoundsInfo
- Publication number
- CA1037969A CA1037969A CA213,866A CA213866A CA1037969A CA 1037969 A CA1037969 A CA 1037969A CA 213866 A CA213866 A CA 213866A CA 1037969 A CA1037969 A CA 1037969A
- Authority
- CA
- Canada
- Prior art keywords
- chlorine
- formula
- hydrogen
- bis
- styryl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 11
- 239000011368 organic material Substances 0.000 claims abstract description 6
- 238000005282 brightening Methods 0.000 claims abstract description 3
- 239000000460 chlorine Chemical group 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000003613 toluenes Chemical class 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000009987 spinning Methods 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052731 fluorine Chemical group 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- -1 styryl compound Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZMLPKJYZRQZLDA-PHEQNACWSA-N 1-[(e)-2-phenylethenyl]-4-[4-[(e)-2-phenylethenyl]phenyl]benzene Chemical group C=1C=CC=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C1=CC=CC=C1 ZMLPKJYZRQZLDA-PHEQNACWSA-N 0.000 description 1
- TUQJLZUOJJDRAH-UHFFFAOYSA-N 2-[2-[4-[4-[2-(2-cyanophenyl)ethenyl]phenyl]phenyl]ethenyl]benzonitrile Chemical group N#CC1=CC=CC=C1C=CC1=CC=C(C=2C=CC(C=CC=3C(=CC=CC=3)C#N)=CC=2)C=C1 TUQJLZUOJJDRAH-UHFFFAOYSA-N 0.000 description 1
- YFQRXTMSTDQFBM-UHFFFAOYSA-N 2-chloro-6-[2-[4-[2-(3-chloro-2-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile Chemical compound ClC1=CC=CC(C=CC=2C=CC(C=CC=3C(=C(Cl)C=CC=3)C#N)=CC=2)=C1C#N YFQRXTMSTDQFBM-UHFFFAOYSA-N 0.000 description 1
- VSHLVYUQNUQHTH-UHFFFAOYSA-N 2-chloro-6-[2-[4-[4-[2-(3-chloro-2-cyanophenyl)ethenyl]phenyl]phenyl]ethenyl]benzonitrile Chemical group ClC1=CC=CC(C=CC=2C=CC(=CC=2)C=2C=CC(C=CC=3C(=C(Cl)C=CC=3)C#N)=CC=2)=C1C#N VSHLVYUQNUQHTH-UHFFFAOYSA-N 0.000 description 1
- ILEOSJJHNCIZER-UHFFFAOYSA-N 2-chloro-6-[2-[6-[2-(3-chloro-2-cyanophenyl)ethenyl]naphthalen-2-yl]ethenyl]benzonitrile Chemical compound ClC1=CC=CC(C=CC=2C=C3C=CC(C=CC=4C(=C(Cl)C=CC=4)C#N)=CC3=CC=2)=C1C#N ILEOSJJHNCIZER-UHFFFAOYSA-N 0.000 description 1
- SDHVCWIOERLKNR-UHFFFAOYSA-N 3-chloro-4-[2-[4-[2-(2-chloro-4-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(C#N)C=C1Cl SDHVCWIOERLKNR-UHFFFAOYSA-N 0.000 description 1
- BYFJPPOHEHDYBK-UHFFFAOYSA-N 3-chloro-4-[2-[4-[4-[2-(2-chloro-4-cyanophenyl)ethenyl]phenyl]phenyl]ethenyl]benzonitrile Chemical group ClC1=CC(C#N)=CC=C1C=CC1=CC=C(C=2C=CC(C=CC=3C(=CC(=CC=3)C#N)Cl)=CC=2)C=C1 BYFJPPOHEHDYBK-UHFFFAOYSA-N 0.000 description 1
- DKTAXQSJXKZOPK-UHFFFAOYSA-N 3-chloro-4-[2-[5-[2-(2-chloro-4-cyanophenyl)ethenyl]naphthalen-2-yl]ethenyl]benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1C=CC1=CC=C(C(C=CC=2C(=CC(=CC=2)C#N)Cl)=CC=C2)C2=C1 DKTAXQSJXKZOPK-UHFFFAOYSA-N 0.000 description 1
- INEMHABDFCKBID-UHFFFAOYSA-N 3-chloro-4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1Cl INEMHABDFCKBID-UHFFFAOYSA-N 0.000 description 1
- BJYDRRRBTVFBON-UHFFFAOYSA-N 4-[2-[4-[4-[2-(4-cyano-3-methoxyphenyl)ethenyl]phenyl]phenyl]ethenyl]-2-methoxybenzonitrile Chemical group C1=C(C#N)C(OC)=CC(C=CC=2C=CC(=CC=2)C=2C=CC(C=CC=3C=C(OC)C(C#N)=CC=3)=CC=2)=C1 BJYDRRRBTVFBON-UHFFFAOYSA-N 0.000 description 1
- UFHZJCRRBDACOT-UHFFFAOYSA-N 4-chloro-2-[2-[4-[2-(5-chloro-2-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile Chemical compound ClC1=CC=C(C#N)C(C=CC=2C=CC(C=CC=3C(=CC=C(Cl)C=3)C#N)=CC=2)=C1 UFHZJCRRBDACOT-UHFFFAOYSA-N 0.000 description 1
- COIWWJAVEAOHTB-UHFFFAOYSA-N 4-chloro-2-[2-[4-[4-[2-(5-chloro-2-cyanophenyl)ethenyl]phenyl]phenyl]ethenyl]benzonitrile Chemical group ClC1=CC=C(C#N)C(C=CC=2C=CC(=CC=2)C=2C=CC(C=CC=3C(=CC=C(Cl)C=3)C#N)=CC=2)=C1 COIWWJAVEAOHTB-UHFFFAOYSA-N 0.000 description 1
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 description 1
- XKAOIBJLDDCCKS-UHFFFAOYSA-N 5-chloro-2-[2-[4-[4-[2-(4-chloro-2-cyanophenyl)ethenyl]phenyl]phenyl]ethenyl]benzonitrile Chemical group N#CC1=CC(Cl)=CC=C1C=CC1=CC=C(C=2C=CC(C=CC=3C(=CC(Cl)=CC=3)C#N)=CC=2)C=C1 XKAOIBJLDDCCKS-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101710190411 Chalcone synthase A Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1624673A CH582134A5 (enrdf_load_stackoverflow) | 1973-11-19 | 1973-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037969A true CA1037969A (en) | 1978-09-05 |
Family
ID=4415656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA213,866A Expired CA1037969A (en) | 1973-11-19 | 1974-11-15 | Process for the manufacture of cyano-substituted bis-styryl compounds |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5084631A (enrdf_load_stackoverflow) |
| BE (1) | BE822271A (enrdf_load_stackoverflow) |
| CA (1) | CA1037969A (enrdf_load_stackoverflow) |
| CH (1) | CH582134A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2453357A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2251549B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1470461A (enrdf_load_stackoverflow) |
| IT (1) | IT1023275B (enrdf_load_stackoverflow) |
| NL (1) | NL7414619A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3339383A1 (de) * | 1983-10-29 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Distyrylverbindungen |
| DE3347576A1 (de) * | 1983-12-30 | 1985-07-11 | Bayer Ag, 5090 Leverkusen | 1,4-bis-(styryl)-benzole und deren verwendung als optische aufheller |
| KR100274871B1 (ko) * | 1998-11-12 | 2000-12-15 | 김순택 | 발광 화합물 및 이를 발색 재료로서 채용하고 있는 표시소자2 |
| EP1153011A1 (en) * | 1999-02-11 | 2001-11-14 | Ciba SC Holding AG | Bis-styrylbiphenyl compounds |
-
1973
- 1973-11-19 CH CH1624673A patent/CH582134A5/xx not_active IP Right Cessation
-
1974
- 1974-11-08 NL NL7414619A patent/NL7414619A/xx not_active Application Discontinuation
- 1974-11-11 DE DE19742453357 patent/DE2453357A1/de active Pending
- 1974-11-12 GB GB4897574A patent/GB1470461A/en not_active Expired
- 1974-11-14 FR FR7437561A patent/FR2251549B1/fr not_active Expired
- 1974-11-15 CA CA213,866A patent/CA1037969A/en not_active Expired
- 1974-11-15 IT IT54070/74A patent/IT1023275B/it active
- 1974-11-18 JP JP49132605A patent/JPS5084631A/ja active Pending
- 1974-11-18 BE BE150571A patent/BE822271A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7414619A (nl) | 1975-05-21 |
| DE2453357A1 (de) | 1975-05-22 |
| IT1023275B (it) | 1978-05-10 |
| CH582134A5 (enrdf_load_stackoverflow) | 1976-11-30 |
| FR2251549B1 (enrdf_load_stackoverflow) | 1979-02-23 |
| JPS5084631A (enrdf_load_stackoverflow) | 1975-07-08 |
| GB1470461A (en) | 1977-04-14 |
| FR2251549A1 (enrdf_load_stackoverflow) | 1975-06-13 |
| BE822271A (fr) | 1975-05-20 |
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