CN1057757C - 基于1,2－二苯乙烯的光学增亮剂的制备 - Google Patents

基于1,2－二苯乙烯的光学增亮剂的制备 Download PDF

Info

Publication number: CN1057757C
Authority: CN; China
Prior art keywords: water; phase; formula; thinner; transfer catalyst
Prior art date: 1994-05-02
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 - Fee Related

Application number

CN95106518A

Other languages

English (en)

Chinese (zh)

Other versions

CN1122799A (zh

Inventor

G·塞波尔德

H·施密特

G·舍弗

H·莱赫尔特

M·豪特赖夫

P·拉茨

P·迪拉维埃

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1994-05-02

Filing date

1995-05-02

Publication date

2000-10-25

1995-05-02 Application filed by BASF SE filed Critical BASF SE

1996-05-22 Publication of CN1122799A publication Critical patent/CN1122799A/zh

2000-10-25 Application granted granted Critical

2000-10-25 Publication of CN1057757C publication Critical patent/CN1057757C/zh

2015-05-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 10
235000021286 stilbenes Nutrition 0.000 title abstract description 9
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 title description 8
230000003287 optical effect Effects 0.000 title description 4
238000000034 method Methods 0.000 claims abstract description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims abstract description 14
239000003444 phase transfer catalyst Substances 0.000 claims abstract description 13
239000003960 organic solvent Substances 0.000 claims abstract description 9
239000003513 alkali Substances 0.000 claims description 11
-1 aromatic series hydrocarbons Chemical class 0.000 claims description 6
150000003008 phosphonic acid esters Chemical class 0.000 claims description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
229910052728 basic metal Inorganic materials 0.000 claims description 2
150000003818 basic metals Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 7
150000002148 esters Chemical class 0.000 abstract description 2
239000003085 diluting agent Substances 0.000 abstract 2
ZWTSHXKQOKSKMB-UHFFFAOYSA-N 2-[2-(1-cyano-2-phenylethenyl)phenyl]-3-phenylprop-2-enenitrile Chemical class C=1C=CC=C(C(=CC=2C=CC=CC=2)C#N)C=1C(C#N)=CC1=CC=CC=C1 ZWTSHXKQOKSKMB-UHFFFAOYSA-N 0.000 abstract 1
FNALVIXJDGVMKX-UHFFFAOYSA-N [cyano(phenyl)methyl]phosphonic acid Chemical compound OP(O)(=O)C(C#N)C1=CC=CC=C1 FNALVIXJDGVMKX-UHFFFAOYSA-N 0.000 abstract 1
150000001629 stilbenes Chemical class 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
KIRAMNJDRSUHPJ-UHFFFAOYSA-N benzonitrile styrene Chemical compound C=CC1=CC=CC=C1.C(#N)C1=CC=CC=C1 KIRAMNJDRSUHPJ-UHFFFAOYSA-N 0.000 description 4
206010013786 Dry skin Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
238000005406 washing Methods 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
UCAHIIZBPCASHX-UHFFFAOYSA-N CC[N+](CC)(CC)CC1=CC=CC=C1.N Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1.N UCAHIIZBPCASHX-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
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 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000005600 alkyl phosphonate group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000002946 cyanobenzyl group Chemical group 0.000 description 1
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
230000006837 decompression Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CN95106518A 1994-05-02 1995-05-02 基于1,2－二苯乙烯的光学增亮剂的制备 Expired - Fee Related CN1057757C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP4415351.1		1994-05-02
DE4415351A DE4415351A1 (de)	1994-05-02	1994-05-02	Verfahren zur Herstellung von optischen Aufhellern auf Stilbenbasis

Publications (2)

Publication Number	Publication Date
CN1122799A CN1122799A (zh)	1996-05-22
CN1057757C true CN1057757C (zh)	2000-10-25

Family

ID=6517025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN95106518A Expired - Fee Related CN1057757C (zh)	1994-05-02	1995-05-02	基于1,2－二苯乙烯的光学增亮剂的制备

Country Status (5)

Country	Link
EP (1)	EP0680947B1 (2)
JP (1)	JPH07300449A (2)
CN (1)	CN1057757C (2)
DE (2)	DE4415351A1 (2)
TW (1)	TW379213B (2)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4380514A (en) *	1980-01-12	1983-04-19	Basf Aktiengesellschaft	Preparation of optical brighteners
US4778623A (en) *	1979-12-13	1988-10-18	Ciba-Geigy Corporation	Fluorescent brighteners consisting of bis-styrylbenzene compounds, a process for their preparation and their use

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1112072B (de) *	1959-08-12	1961-08-03	Basf Ag	Verfahren zur Herstellung von Verbindungen der 1, 4-Bis-(styryl)-benzolreihe

1994
- 1994-05-02 DE DE4415351A patent/DE4415351A1/de not_active Withdrawn
1995
- 1995-04-20 TW TW084103904A patent/TW379213B/zh not_active IP Right Cessation
- 1995-04-24 DE DE59503489T patent/DE59503489D1/de not_active Expired - Fee Related
- 1995-04-24 EP EP95106068A patent/EP0680947B1/de not_active Expired - Lifetime
- 1995-04-26 JP JP7102555A patent/JPH07300449A/ja not_active Withdrawn
- 1995-05-02 CN CN95106518A patent/CN1057757C/zh not_active Expired - Fee Related

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4778623A (en) *	1979-12-13	1988-10-18	Ciba-Geigy Corporation	Fluorescent brighteners consisting of bis-styrylbenzene compounds, a process for their preparation and their use
US4380514A (en) *	1980-01-12	1983-04-19	Basf Aktiengesellschaft	Preparation of optical brighteners

Also Published As

Publication number	Publication date
DE4415351A1 (de)	1995-11-09
DE59503489D1 (de)	1998-10-15
EP0680947A2 (de)	1995-11-08
EP0680947B1 (de)	1998-09-09
TW379213B (en)	2000-01-11
CN1122799A (zh)	1996-05-22
JPH07300449A (ja)	1995-11-14
EP0680947A3 (2)	1995-11-29

Legal Events

Date	Code	Title
1996-05-22	C06	Publication
1996-05-22	PB01	Publication
1997-05-14	C10	Entry into substantive examination
1997-05-14	SE01	Entry into force of request for substantive examination
2000-10-25	C14	Grant of patent or utility model
2000-10-25	GR01	Patent grant
2009-07-08	C19	Lapse of patent right due to non-payment of the annual fee
2009-07-08	CF01	Termination of patent right due to non-payment of annual fee

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EP0041043B1 (de)	1983-11-09	Verfahren zur Herstellung von Alkenylbenzol- oder -naphthalin-derivaten
US20040006235A1 (en)	2004-01-08	Process for the preparation of ring compounds
KR100535166B1 (ko)	2005-12-09	중합 가능한 비아릴, 이의 제조방법 및 이의 용도
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DE3130628A1 (de)	1983-02-17	Substituierte 1-phenyl-vinyl-1-phosphonsaeuren und ihre verwendung
US2572845A (en)	1951-10-30	Alkylthiosulfenyl dithiocarbamates and preparation thereof
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US4794205A (en)	1988-12-27	Method for producing alkenylthiophenols and their esters
CA2205671A1 (en)	1997-11-20	Process for the preparation of esters of aromatic carboxylic acid
US4120868A (en)	1978-10-17	Cyclic 2-methyl-2,4-dialkoxy-3-buten-1-al-acetals, their preparation and use
CN1276905C (zh)	2006-09-27	用二氯代酚与氯代烷合成二氯代芳醚的方法
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DE2103244A1 (de)	1971-08-05	Ultraviolettlicht Stabilisatoren
EP0150169A2 (en)	1985-07-31	A process for preparing substituted benzotrichloride compounds