GB906523A - Compounds of the 1,4-divinylbenzene series and their production - Google Patents
Compounds of the 1,4-divinylbenzene series and their productionInfo
- Publication number
- GB906523A GB906523A GB1691660A GB1691660A GB906523A GB 906523 A GB906523 A GB 906523A GB 1691660 A GB1691660 A GB 1691660A GB 1691660 A GB1691660 A GB 1691660A GB 906523 A GB906523 A GB 906523A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- benzene
- xylylene
- styryl
- preparation
- 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
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical class C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 6
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical compound [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000002430 hydrocarbons Chemical group 0.000 abstract 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 3
- -1 sulphonic acid nitro Chemical group 0.000 abstract 3
- IJAAWBHHXIWAHM-PHEQNACWSA-N 1,4-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C(C=C1)=CC=C1\C=C\C1=CC=CC=C1 IJAAWBHHXIWAHM-PHEQNACWSA-N 0.000 abstract 2
- QEMXVOZFCBVEDQ-UHFFFAOYSA-N 1,4-dichloro-2,5-bis(2-phenylethenyl)benzene Chemical compound ClC=1C=C(C=CC=2C=CC=CC=2)C(Cl)=CC=1C=CC1=CC=CC=C1 QEMXVOZFCBVEDQ-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 125000006839 xylylene group Chemical group 0.000 abstract 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 abstract 1
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 abstract 1
- XHONDXMIWPFPLA-UHFFFAOYSA-N 1,4-bis[2-(4-nitrophenyl)ethenyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C([N+]([O-])=O)C=C1 XHONDXMIWPFPLA-UHFFFAOYSA-N 0.000 abstract 1
- PMORXEIGELBSFG-UHFFFAOYSA-N 1,4-bis[2-(4-phenylphenyl)ethenyl]benzene Chemical compound C1(=CC=CC=C1)C1=CC=C(C=CC2=CC=C(C=C2)C=CC2=CC=C(C=C2)C2=CC=CC=C2)C=C1 PMORXEIGELBSFG-UHFFFAOYSA-N 0.000 abstract 1
- RTELVSLOASMARY-UHFFFAOYSA-N 1,4-dimethoxy-2,5-bis(2-phenylethenyl)benzene Chemical compound COC=1C=C(C=CC=2C=CC=CC=2)C(OC)=CC=1C=CC1=CC=CC=C1 RTELVSLOASMARY-UHFFFAOYSA-N 0.000 abstract 1
- AXKXCFVOHOECFI-UHFFFAOYSA-N 1-[2-[4-[2-(9,10-dioxoanthracen-1-yl)-2-phenylethenyl]phenyl]-1-phenylethenyl]anthracene-9,10-dione Chemical compound C1(=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=CC1=CC=C(C=C1)C=C(C1=CC=CC=C1)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C1=CC=CC=C1 AXKXCFVOHOECFI-UHFFFAOYSA-N 0.000 abstract 1
- YPDMBLQOYRZPJJ-UHFFFAOYSA-N 2-[4-(1-cyano-2-phenylethenyl)phenyl]-3-phenylprop-2-enenitrile Chemical class C=1C=C(C(=CC=2C=CC=CC=2)C#N)C=CC=1C(C#N)=CC1=CC=CC=C1 YPDMBLQOYRZPJJ-UHFFFAOYSA-N 0.000 abstract 1
- DLYAKFIGWLYUSU-UHFFFAOYSA-N 3-[2-[4-[2-(3-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile Chemical compound N#CC1=CC=CC(C=CC=2C=CC(C=CC=3C=C(C=CC=3)C#N)=CC=2)=C1 DLYAKFIGWLYUSU-UHFFFAOYSA-N 0.000 abstract 1
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 abstract 1
- WVDVJQSVTBHGQL-UHFFFAOYSA-N 4-(morpholine-4-carbonyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C(=O)N1CCOCC1 WVDVJQSVTBHGQL-UHFFFAOYSA-N 0.000 abstract 1
- FQSHCTXVYDFFOB-UHFFFAOYSA-N 4-[2-[4-[2-[4-(dimethylamino)phenyl]ethenyl]phenyl]ethenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(N(C)C)C=C1 FQSHCTXVYDFFOB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- RVDJLKVICMLVJQ-UHFFFAOYSA-N diethoxy(phenyl)phosphane Chemical compound CCOP(OCC)C1=CC=CC=C1 RVDJLKVICMLVJQ-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- PKAQDUGAIWAFJZ-UHFFFAOYSA-N methyl 4-[2-[4-[2-(4-methoxycarbonylphenyl)ethenyl]phenyl]ethenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(C(=O)OC)C=C1 PKAQDUGAIWAFJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
- C07C1/324—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a phosphorus atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of the 1,4-divinylbenzene series such as 1,4-distyrylbenzene, 1,4-bis-(cyanostyryl)-benzenes, 1,4-bis-(dialkoxystyryl)-benzenes, 1,4-bis-styryl-2,5-dialkoxybenzenes, and 1,4-bis-styryl-2,5-dichlorobenzene, are made by reacting a mono- or di-aldehyde, which may have cyano, alkoxy, nitro, dialkylamino, chloro, or alkoxycarbonyl substituents, with a xylylene, diphosphonate or diphosphinate of the formula <FORM:0906523/IV (b)/1> wherein R1 is a hydrocarbon, alkoxy, or aryloxy group, and R2 is hydrocarbon group, R3, R4, R5 and R6 are hydrogen or halogen atoms or alkyl, alkoxy, sulphonic acid nitro, or mercapto groups, or taken in pairs they may represent a carbocyclic ring or a dioxymethylene chain, and R7 and R8 are hydrogen atoms or cyano or carboalkoxy groups in the presence of a proton acceptor such as a hydroxide, alcoholate or amide or an alkali or alkaline-earth metal. In Example 1, benzaldehyde is mixed with a solution of p-xylylene-tetraethyl phosphonate in dimethylformamide; and then, while stirring vigorously, a methanolic solution of sodium methylate is added. 1,4-Distyrylbenzene is precipitated as yellowish fluorescent leaflets. Example 20 relates to the preparation of distyrylbenzene by reacting benzaldehyde with the ethyl ester of p - xylylene - bis - phenylphosphinic acid. Examples 5, 15, 22 and 28 relate to the preparation of the following hydrocarbons:-1,4 - dinaphthostyryl-benzene, 1,4-bis-(omega-phenyl-butadienyl)-benzene and 1,4-bis-(p-phenyl-styryl)-benzene. Example 7 describes the preparation of 1,4-bis-(m-cyanostyryl)-benzene by reacting m-cyanobenzaldehyde with p - xylylene - tetraethyl diphosphonate. Examples 16 and 24 relate to the preparation of the corresponding para- and ortho-cyano compounds. Example 8 describes the preparation of 1,4-distyryl-2,5-dimethoxybenzene by reacting benzaldehyde with 2,5-dimethoxy-1,4-xylylene-tetraethyl diphosphonate. Example 12 describes the preparation of 1,4-bis-(21,41-dimethoxystyryl)-benzene. In Example 11, vanillin-tetrahydrofuranyl ether is reacted with p-xylylene-tetraethyl diphosphonate to give 1,4 - bis - (41 - alpha - tetrahydrofuranyloxy - 31 - methoxy-styryl)-benzene, and the latter is then treated with boiling glacial acetic acid whereby 1,4 - bis - (31 - methoxy - 41 - hydroxystyryl)-benzene is obtained. Examples 6 and 19 relate to the preparation of 1,4-bis-(31,41-dioxymethylene-styryl)-benzene. Examples 2, 3, 4, 10, and 17 relate to the preparation of 1,4-bis-(beta-anthraquinonyl-styryl) - benzene, 1,4 - bis - (p-nitrostyryl)-benzene, 1,4-bis-(p-dimethylaminostyryl)-benzene, 1,4-distyryl-2,5-dichlorobenzene and 1,4 - bis - (p-carbmethoxy-styryl)-benzene. Example 26 describes the reaction of p-xylylene-tetraethyl diphosphonate with 4-formyl-benzoic acid morpholide to yield 1,4-bis-(p-carbmorpholido-styryl)-benzene. The required xylylene diphosphonates or diphosphinates are made by reacting p-xylylene dichloride, or a nuclear substituted derivative thereof, with a trialkyl phosphite (see Examples 1, 8, 10, 21 and 23) or with phenyl diethoxy phosphine (Example 19). The 1,4-divinylbenzene compounds have use as optical brighteners.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB53252A DE1108219B (en) | 1959-05-15 | 1959-05-15 | Process for the preparation of compounds of the 1,4-divinyl-benzene series |
| DEB57066A DE1122065B (en) | 1960-03-15 | 1960-03-15 | Process for the preparation of compounds of the 1,4-divinylbenzene series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB906523A true GB906523A (en) | 1962-09-26 |
Family
ID=25965385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1691660A Expired GB906523A (en) | 1959-05-15 | 1960-05-13 | Compounds of the 1,4-divinylbenzene series and their production |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH388929A (en) |
| GB (1) | GB906523A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163621A (en) * | 1960-10-26 | 1964-12-29 | Basf Ag | Polyamides stabilized with styryl benzenes or stilbenes |
| FR2193816A1 (en) * | 1972-07-26 | 1974-02-22 | Hickson & Welch Ltd |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030917B2 (en) * | 1979-12-13 | 1991-03-20 | Ciba-Geigy Ag | Optical brighteners from bistyryl benzene, process for their preparation and their use |
-
1960
- 1960-04-29 CH CH494960A patent/CH388929A/en unknown
- 1960-05-13 GB GB1691660A patent/GB906523A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163621A (en) * | 1960-10-26 | 1964-12-29 | Basf Ag | Polyamides stabilized with styryl benzenes or stilbenes |
| FR2193816A1 (en) * | 1972-07-26 | 1974-02-22 | Hickson & Welch Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| CH388929A (en) | 1965-03-15 |
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