WO1991016329A1 - Composes organo silicies materiaux et dispositifs electrooptiques les contenant - Google Patents
Composes organo silicies materiaux et dispositifs electrooptiques les contenant Download PDFInfo
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- WO1991016329A1 WO1991016329A1 PCT/FR1991/000338 FR9100338W WO9116329A1 WO 1991016329 A1 WO1991016329 A1 WO 1991016329A1 FR 9100338 W FR9100338 W FR 9100338W WO 9116329 A1 WO9116329 A1 WO 9116329A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 11
- 239000000463 material Substances 0.000 title claims description 4
- -1 C1-8alkyl radical Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 abstract description 14
- 150000005840 aryl radicals Chemical class 0.000 abstract description 6
- 239000001257 hydrogen Chemical group 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000011777 magnesium Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 13
- 239000011630 iodine Substances 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 230000003595 spectral effect Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XYZWMVYYUIMRIZ-UHFFFAOYSA-N 4-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Br)C=C1 XYZWMVYYUIMRIZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- VIPCDVWYAADTGR-UHFFFAOYSA-N trimethyl(methylsilyl)silane Chemical compound C[SiH2][Si](C)(C)C VIPCDVWYAADTGR-UHFFFAOYSA-N 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HHMAUSAHIFZCAJ-UHFFFAOYSA-N 2-[(4-trimethylsilylphenyl)methylidene]propanedinitrile Chemical compound C[Si](C)(C)C1=CC=C(C=C(C#N)C#N)C=C1 HHMAUSAHIFZCAJ-UHFFFAOYSA-N 0.000 description 1
- XEMWZSDUSRVJTQ-UHFFFAOYSA-N 2-[[4-[[4-(dimethylamino)phenyl]-methylsilyl]phenyl]methylidene]propanedinitrile Chemical compound C(#N)C(=CC1=CC=C(C=C1)[SiH](C)C1=CC=C(C=C1)N(C)C)C#N XEMWZSDUSRVJTQ-UHFFFAOYSA-N 0.000 description 1
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
- ZTIDAQCZRVLOFN-UHFFFAOYSA-N 4-[(4-bromophenyl)-[4-(dimethylamino)phenyl]-methylsilyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1[Si](C)(C=1C=CC(=CC=1)N(C)C)C1=CC=C(Br)C=C1 ZTIDAQCZRVLOFN-UHFFFAOYSA-N 0.000 description 1
- NNOSURKRJUIVRT-UHFFFAOYSA-N 4-[bis[4-(dimethylamino)phenyl]-methylsilyl]benzaldehyde Chemical compound C1=CC(N(C)C)=CC=C1[Si](C)(C=1C=CC(=CC=1)N(C)C)C1=CC=C(C=O)C=C1 NNOSURKRJUIVRT-UHFFFAOYSA-N 0.000 description 1
- BPCNVZGALJUWSO-UHFFFAOYSA-N 4-trimethylsilylbenzaldehyde Chemical compound C[Si](C)(C)C1=CC=C(C=O)C=C1 BPCNVZGALJUWSO-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 150000001787 chalcogens Chemical class 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005672 electromagnetic field Effects 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
- G02F1/3619—Organometallic compounds
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
Definitions
- the present invention relates to new organosilicon compounds, their manufacturing process and their use in non-linear optics. It particularly relates to a subfamily of organosilicon compounds which are the subject of the French patent application filed under the number
- - n is an integer between 1 and 20,
- R 3 represents an alkyl radical comprising from 1 to 8 carbon atoms, hydrogen, an aryl radical, an R 1 or R 2 radical;
- R 4 represents an alkyl radical comprising from 1 to 8 carbon atoms, hydrogen, an aryl radical, a radical R 1 when R 3 does not represent a radical R 2 , or a radical R 2 when R 3 does not represent a radical R 1 .
- R 5 represents an arylene radical
- - D identical or different represents hydrogen or an electron donor radical chosen if in the group comprising the amino, al kyl amino, di al kyl amino, aryl amino, hydroxyl, thiol o, al kyl thio, al radicals koxy, aryloxy, haloal kyl, oxy,
- n is an integer equal to 1,2 or 3
- D does not represent hydrogen when the group R 4 is an aryl radical unsubstituted by one or more electron accepting groups.
- the term “donor group” should be understood to mean either any group whose Hammett constant ⁇ p defined by J. March, p. 242-244 in "Advanced Organic Chemistry” (John WILEY and Son, 3rd edition) is negative, preferably less than -0.20, that is to say any aromatic group substituted by at least one of these donor groups.
- the acceptor groups are deemed to be either those characterized by a positive Hammett constant ⁇ p , preferably ⁇ p greater than 0.40, or any aromatic group substituted by at least one of these acceptor groups, directly or indirectly through bonds at least double.
- the aryls are advantageously heterocyles, preferably with 5 links.
- the preferred heterocycles according to the present invention have as paradigm the bi- and the monopyrroles, thiophenes, furans.
- the attachment point to the sillicium advantageously being in the vicinal position of the heteroatom. If said heteroatom is trivalent, the point of attachment may also be said heteroatom.
- heterocycles comprising 2 heteroatoms.
- the donor aryl radicals are those for which the measurement of the Hammett constant leads to a negative value, or which carries a grouping to a negative value.
- preferred radicals are of course those which carry both a silyl and an aryl as defined above.
- the radical R 1 is either an alkyl of 1 to 8 carbon atoms, preferably from 1 to 4, or a silyl of a silicon atom and from 3 to 20 carbon atoms, preferably from 5 to 9 atoms of carbon.
- silyl radicals consisting of a silicon atom surrounded by 3 alkyl groups, preferably identical, such as for example the trimethyl silyl or triethylsilyl radicals.
- ⁇ 0 limit value of the hyperpolarisibility of extrapolated for a zero frequency of the electromagnetic fields
- p DMA is the paradimethyl aniline group, or paradimethylaminophenylene
- the pMP group is the paramethoxyphenylene group
- R 4 represents the
- R 4 CH - C (CN) 2
- a solution of 4-bromodimethyl aniline (50 g, 0.25 mole) in THF (50 ml) is added to a suspension of magnesium (6.1 g, 0.25 mole) in THF, an iodine crystal, and gently (30 minutes) ).
- the mixture was heated at reflux for 6 hours and was then added slowly (30 min) to a solution of 2.1 (97.6 g, 0.25 mole with a purity of 94%) in 50 ml of THF.
- the temperature was maintained at around 40o C.
- the mixture was refluxed for 16 hours.
- the solvent is stirred and 200 ml of ether is added to it. After filtration, the organic layer is poured into 60 ml of water and the solvent is displaced.
- the residue was chromatographed on a column filled with silica gel (silica gel) with ether-hexane (1/1 by volume) to give 90 g of 2.2 of a yellow oil.
- ethyl / hexane 50/50; V / V); 0.62 g of a red solid is recovered which is recrystallized from hexane.
- RMNCl3 (CDCl3): ⁇ -4.1, -2.6 (-Si (CH 3 ) 2 ), 137.3-135.4-130.9-123, 4 ( C6 H 4 Br),
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Inorganic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9005256A FR2661412B2 (fr) | 1988-04-20 | 1990-04-25 | Composes organo silicies materiaux et dispositifs electrooptiques les contenant. |
FR90/05256 | 1990-04-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1991016329A1 true WO1991016329A1 (fr) | 1991-10-31 |
Family
ID=9396064
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1991/000338 WO1991016329A1 (fr) | 1990-04-25 | 1991-04-24 | Composes organo silicies materiaux et dispositifs electrooptiques les contenant |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0480011A1 (fr) |
JP (1) | JPH05501884A (fr) |
WO (1) | WO1991016329A1 (fr) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2630442A1 (fr) * | 1988-04-20 | 1989-10-27 | Rhone Poulenc Chimie | Composes organosilicies, materiaux et dispositifs electrooptiques les contenant |
-
1991
- 1991-04-24 EP EP91908935A patent/EP0480011A1/fr not_active Withdrawn
- 1991-04-24 JP JP3508759A patent/JPH05501884A/ja active Pending
- 1991-04-24 WO PCT/FR1991/000338 patent/WO1991016329A1/fr not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2630442A1 (fr) * | 1988-04-20 | 1989-10-27 | Rhone Poulenc Chimie | Composes organosilicies, materiaux et dispositifs electrooptiques les contenant |
Non-Patent Citations (4)
Title |
---|
Applied Physics Letters, volume 53, no. 13, 26 septembre 1988, (New York, NY, US) J.-C. Baumert et al.: "Temperature dependence of the third-order nonlinear optical susceptibilities in polysilanes and polygermanes", pages 1147-1149 * |
Chemical Abstracts, volume 13, 1990, (Columbus, OH, US), G. Mignani et al.: "A new class of silicon compounds with interesting nonlinear optical effects", voir page 796, abrégé 152564b & Organometallics, 1990, 9(10), 2640-3 * |
Journal General Chemistry of the USSR, volume 46, no. 11, partie 2, novembre 1976, I.P. Gol'dshtein et al.: "Dipole moments and molecular refractions of aryl derivatives of mono-, di-, and trisilanes and silacyclobutanes", pages 2429-2433 * |
Journal of Organometallic Chemistry, volume 225, no. 1, 1 février 1982, Elsevier Sequoia S.A., (NL), H. Sakurai et al.: "Preparation and UV spectra of nitrophenylpolysilanes", pages 163-170 * |
Also Published As
Publication number | Publication date |
---|---|
JPH05501884A (ja) | 1993-04-08 |
EP0480011A1 (fr) | 1992-04-15 |
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