WO1995020182A1 - Utilisation d'azoanilines d'aryle ou d'heteroaryle en optique non lineraire - Google Patents

Utilisation d'azoanilines d'aryle ou d'heteroaryle en optique non lineraire Download PDF

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Publication number
WO1995020182A1
WO1995020182A1 PCT/EP1995/000129 EP9500129W WO9520182A1 WO 1995020182 A1 WO1995020182 A1 WO 1995020182A1 EP 9500129 W EP9500129 W EP 9500129W WO 9520182 A1 WO9520182 A1 WO 9520182A1
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WIPO (PCT)
Prior art keywords
formula
hydrogen
alkyl
azo dyes
derived
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PCT/EP1995/000129
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German (de)
English (en)
Inventor
Stefan Beckmann
Karlz-Heinz Etzbach
Rüdiger Sens
Gerhard Wagenblast
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Basf Aktiengesellschaft
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Publication of WO1995020182A1 publication Critical patent/WO1995020182A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • 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
    • G02F1/3611—Organic materials containing Nitrogen
    • 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
    • G02F1/3611—Organic materials containing Nitrogen
    • G02F1/3612—Heterocycles having N as heteroatom
    • 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
    • G02F1/3613—Organic materials containing Sulfur
    • G02F1/3614—Heterocycles having S as heteroatom

Definitions

  • the present invention relates to the use of azo dyes with a diazo component which is derived from an .aniline or from a five-membered aromatic heterocyclic amine which has one to three heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, has in the heterocyclic ring and can be fused by a benzene, thiophene, pyridine or pyrimidine ring, and a coupling component from the aniline series in the nonlinear optics, polymers derived from the azo dyes mentioned, and their use in the nonlinear Optics.
  • a diazo component which is derived from an .aniline or from a five-membered aromatic heterocyclic amine which has one to three heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, has in the heterocyclic ring and can be fused by a benzene, thiophene, pyridine or pyrimidine ring, and a coupling component from the aniline series in the nonlinear optics
  • nonlinear optical properties of organic compounds are used in many areas of optoelectronics. Examples of this are applications in frequency doubling, in phase modulators, optical amplifiers, interferometers, optical switches or in communications technology.
  • organic materials in particular polymers with special chromophores, can have nonlinear optical properties, some of which are larger than those of comparable inorganic materials.
  • the currently most commonly used materials are inorganic crystals, e.g. from potassium dihydrogen phosphate or lithium niobate. These crystals are complex and expensive to manufacture and, because of their rigid structure, are difficult to use in optical devices. Another disadvantage is their low non-linear effects.
  • a particular advantage of suitable organic chromophores and their use in polymeric materials is their simple manufacture and processing.
  • the chromophores used in nonlinear optics are usually used either in crystalline or polymer-bound form.
  • R 1 and R 2 are each independently of one another hydrogen, C 1 -C 6 -alkyl or C 5 -C 7 -cycloalkyl and
  • R 3 and R 4 independently of one another each represent hydrogen or Ci-C ⁇ -alkyl, which can be substituted by hydroxy, acryloyloxy or methacryloyloxy,
  • azo dyes of the formula I in which D represents the remainder of a diazo component which is derived from an aniline or from a heterocyclic amine from the pyrrole, furan, thiophene, pyrazole, imidazole, oxazole , Isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, benzofuran, benzothiophene, benzimidazole, benzoxazole, benzothiazole, benzisothiazole, pyridothiophene, pyrimidothiophene or thienothiazole series.
  • azo dyes of the formula I in which D represents the remainder of a diazo component which is derived from an aniline or from a heterocyclic amine from pyrrole, thiophene, pyrazole or thiazole , Isothiazole, triazole, thiadiazole, benzthiophene, benzthiazole, benzisothiazole, pyridothiophene, pyrimidothiophene or thienothiazole series.
  • L 2 hydrogen, -CC 6 alkyl, halogen, hydroxy, mercapto, optionally substituted by phenyl or C ⁇ -C alkoxy
  • Ci-C ⁇ -alkoxy optionally substituted phenoxy, optionally substituted by phenyl Ci-C ⁇ -alkylthio, optionally substituted phenylthio, Ci-C ⁇ -alkylsulfonyl or optionally substituted phenylsulfonyl,
  • L 4 is hydrogen, Ci-C ⁇ -alkyl or phenyl
  • L 6 is hydrogen, cyano, -CC alkoxycarbonyl, Ci-C ⁇ -alkanoyl, thiocyanato or halogen,
  • L 8 hydrogen, Ci-C ⁇ -alkyl, cyano, halogen, Ci-C ⁇ -alkoxy optionally substituted by phenyl or -CC alkoxy, optionally substituted by phenyl Ci-Ce-alkylthio, optionally substituted phenylthio, Ci C ⁇ -alkylsulfonyl, phenylsulfonyl or substituted gege ⁇ appropriate, C ⁇ -C ⁇ Alkoxycar- carbonyl,
  • L 9 cyano, optionally substituted by phenyl Ci-C ⁇ -alkyl, optionally substituted by phenyl Ci-C ⁇ - alkylthio, optionally substituted phenyl, thienyl, C 1 -C 4 alkyl thienyl, pyridyl or C 1 -C 4 alkyl pyridyl,
  • L 11 trifluoromethyl, nitro, Ci-Cö-alkyl, phenyl, optionally substituted by phenyl Ci-C ⁇ -alkylthio or Ci-C ⁇ -dialkylamino, L 12 -C 6 alkyl, phenyl, 2-cyanoethylthio or 2- (C 4 alkoxycarbonyl) ethylthio,
  • L 14 is hydrogen, cyano, -CC alkoxycarbonyl, nitro or halogen and
  • L 15 , L 16 and L 17 are the same or different and, independently of one another, are each hydrogen, Ci-C ⁇ -alkyl, Ci-C ⁇ alkoxy, halogen, nitro, formyl, cyano, C 1 -C 4 -alkoxycarbonyl, Ci -C ⁇ - alkyl sulfonyl or optionally substituted phenylsulfonyl or L 16 is also optionally substituted by nitro-substituted phenylazo.
  • substituents can be e.g. C 1 -C 6 alkyl, chlorine, bromine, nitro or C 1 -C 4 alkoxy come into consideration.
  • the phenyl radicals generally have 1 to 3 substituents.
  • Radicals L 2 , L 4 , *, L-8, L 9 , L ", L * 2 , L * 5 ,”, L 17 , Rl f R 2 , R 3 and R 4 are, for example, methyl, ethyl, propyl, Isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
  • R 1 and R 2 are, for example, cyclopentyl, cyclohexyl or cycloheptyl.
  • R 3 and R 4 are furthermore, for example, 2-hydroxyethyl, 2- or 3-hydroxypropyl, 2- or 4-hydroxybutyl, 5-hydroxypentyl, 6-hydroxyhexyl, 2-aminoethyl, 2- or 3-aminopropyl, 2- or 4 -Aminobutyl, 5-aminopentyl, 6-aminohexyl, 2-acryloyloxyethyl, 2-methacryloyloxyethyl, 2- or 3-acryloyloxypropyl, 2- or 3-methacryloyloxypropyl, 2- or 4-acryloyloxybutyl, 2- or 4-methacryloyloxybutyl, 5-acryloyloxypentyl , 5-methacryloyloxypentyl, 6-acryloyloxyhexyl or 6-methacryloyloxyhexyl.
  • L 9 radicals are also, for example, benzyl or 1- or 2-phenylethyl.
  • L 2 , L 8 , L 9 and 11 are, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, hexylthio, benzylthio or 1- or 2-phenylethylthio.
  • L 2 and L 8 are, for example, phenylthio, 2-methylphenylthio, 2-methoxyphenylthio or 2-chlorophenylthio.
  • L 2 , L 8 , L 15 , L 16 and L 17 are, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy or 2-methylpentyloxy.
  • L 6 like L 2 , L 8 , 13 , L 14 , L 15 , L 16 and L 17 , are, for example, fluorine, chlorine or bromine.
  • L 7 like L 1 , L 2 , L 8 , L 15 , L 16 and L 17 , are, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl sec-butylsulfonyl, pentylsulfonyl, isopentylsulfone , Neopentylsulfonyl, hexylsulfonyl, phenylsulfonyl, 2-methylphenylsulfonyl, 2-methoxyphenylsulfonyl or 2-chlorophenylsulfonyl.
  • L 3 radicals as are also 6 , L 7 , L 8 , L 14 , L 15 , 16 and L 17 radicals, are, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl or sec-butoxycarbonyl.
  • L 2 and L 8 are furthermore, for example, 2-methoxyethoxy, 2-ethoxyethoxy, 2- or 3-methoxypropoxy, 2- or 3-ethoxypropoxy, 2- or 4-methoxybutoxy, 2- or 4-ethoxybutoxy, 5-Met oxypentyl-oxy, 5-ethoxypentyloxy, 6-methoxyhexyloxy, 6-ethoxyhexyloxy, benzyloxy or 1- or 2-phenylet oxy.
  • L 11 radicals are also, for example, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, dipentylamino, dihexylamino or N-methyl-N-ethylamino.
  • L 12 radicals are furthermore, for example, 2-methoxycarbonylethylthio or 2-ethoxycarbonylethylthio.
  • L 9 radicals are furthermore, for example, phenyl, 2-, 3- or 4-methylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-methoxyphenyl, 2- or 3-methylthienyl or 2-, 3- or 4-methylpyridyl.
  • L 1 , L 6 and L 7 are furthermore, for example, formyl, acetyl, propionyl, butyryl, pentanoyl or hexanoyl.
  • Z 1 cyano, nitro, C ⁇ -C -alkanoyl, optionally substituted benzoyl, -C-C 4 -alkylsulfonyl, optionally substituted phenylsulfonyl, carboxyl, C ⁇ -C -alkoxycarbonyl, C 3 -C -alkenyloxycarbonyl, phenoxycarbonyl, carbamoyl, C ⁇ ⁇ C -mono- or dialkylcarbamoyl, optionally substituted phenylcarbamoyl, optionally substituted phenyl, benzthiazol-2-yl, benzimidazol-2-yl, 5-phenyl-l, 3, -thiadiazol-2-yl or 2-hydroxyquinoxaline 3-yl,
  • Z 5 is hydrogen, -CC 6 ⁇ alkyl, -C-C 4 -alkanoylamino, benzoylamino or N- (C ⁇ -C -alkanoyl) -N-benzoylamino,
  • Z 6 is hydrogen, C 1 -C 4 -alkyl or phenyl
  • Z 7 oxygen or sulfur and Z 8 is C 1 -C 4 alkyl.
  • the radical derived from compounds of formula IIIa, IIIb or HLC, wherein Z 1 is cyano, C 4 alkanoyl, C ⁇ -C alkoxycarbonyl, or C 3 -C 4 alkenyloxycarbonyl, Z 2 C ⁇ -C alkyl , -CC 4 -alkoxy or C -C -alkenyloxy, Z 3 -CC 4 -alkoxycarbonyl or C -C 4 -alkenyloxycarbonyl and Z 4 cyano mean to emphasize.
  • Z 1 is cyano, C 1 -C 4 -alkoxycarbonyl or C 3 -C 4 -alkenyloxycarbonyl, Z 2 C 1 -C 4 -alkoxy or C 2 -C 4 alkenyloxy, Z 3 -C-C 4 alkoxycarbonyl or C 3 -C 4 alkenyl oxycarbonyl and Z 4 mean cyano.
  • azo dyes of the formula I in which R 1 is hydrogen and R 2 is C 3 -C 4 alkyl, in particular isopropyl, sec-butyl or tert-butyl.
  • L 16 is nitro, cyano or -CC 4 alkoxycarbonyl and L 17 is hydrogen or nitro.
  • the azo dyes of the formula I are known per se and are described, for example, in US Pat. No. 5,283,326, DE-A-3 108 077, US-A-4 843 153 or GB-A-1 546 803 or can be described there mentioned methods can be obtained.
  • the azo dyes of the formula I have particularly large molecular hyperpolarizability values ( ⁇ ).
  • the present invention further relates to azo-containing polymers which, as characteristic monomer units, contain a divalent radical which is derived from an azo dye of the formula I, and radicals of the formulas IV, V and VI
  • Q 2 is hydrogen or methyl
  • W is C -C-alkylene
  • the proportion of the monomer units of the bivalent radicals derived from formula I is 1 to 100 mol%, that of formula IV 0 to 99 mol%, that of formula V 0 to 99 mol% and that Formula VI 0 to 75 mol%, based in each case on the polymer, and the average molecular weight of the polymer being 1,000 to 500,000.
  • a divalent radical derived from an azo dye of the formula I obeys the formula VII
  • the preparation of the new polymers can be carried out according to methods known per se, such as e.g. in J. Polymer Sei., Part A, Polymer Chem., Volume 28, pages 1 to 13, 1990.
  • Q 2 and W each have the abovementioned meaning, in the above molar ratio in an inert solvent (for example toluene or xylene) in the presence of a radical initiator (for example azo-bis-isobutyronitrile).
  • an inert solvent for example toluene or xylene
  • a radical initiator for example azo-bis-isobutyronitrile
  • the polymers containing azo dyes of the formula I are also advantageously suitable for use in nonlinear optics.
  • the polymers according to the invention are thermally stable and have particularly large molecular hyperpolarizability values ( ⁇ ).
  • the molecular hyperpolarizability can be determined, for example, by the solvatochromism measurement method (see, for example, Z. Natur ⁇ aba, volume 20a, pages 1441 to 1471, 1965, or J. Org. Chem., Volume 54, pages 3775 to 3778, 1989).
  • the position of the absorption band of a compound in various solvents is determined.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Nonlinear Science (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne l'utilisation en optique non linéaire de colorants azoïques de la formule (I) et de polymérisats contenant des colorants azoïques, qui renferment comme unités monomères caractéristiques un reste bivalent dérivé d'un colorant azoïque de la formule (I), dans laquelle D désigne le reste d'un constituant diazoïque, dérivé d'une aniline ou d'une amine aromatique hétérocyclique à cinq chaînons qui présente dans le noyau hétérocyclique un à trois hétéroatomes choisis dans le groupe composé de l'azote, de l'oxygène et du soufre, et qui peut être anellée par un noyau benzène, thiophène, pyridine ou pyrimidine, R1 et R2 désignent indépendamment l'un de l'autre hydrogène, alkyle C¿1?-C6 ou cycloalkyle C5-C7, et R?3 et R4¿ désignent indépendamment l'un de l'autre hydrogène ou alkyle C¿1?-C6 pouvant être substitué par hydroxy, acryloyloxy ou méthacryloyloxy, à condition qu'au moins un des deux restes R?1 et R2¿ ne soit pas hydrogène.
PCT/EP1995/000129 1994-01-24 1995-01-13 Utilisation d'azoanilines d'aryle ou d'heteroaryle en optique non lineraire WO1995020182A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944401911 DE4401911A1 (de) 1994-01-24 1994-01-24 Verwendung von Aryl- oder Heteroarylazoanilinen in der nichtlinearen Optik
DEP4401911.4 1994-01-24

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WO1995020182A1 true WO1995020182A1 (fr) 1995-07-27

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7055151B1 (en) 1998-04-03 2006-05-30 Applied Micro Circuits Corporation Systems and methods for multi-tasking, resource sharing and execution of computer instructions
US8129541B2 (en) 2002-02-28 2012-03-06 Novartis Ag 5-phenylthiazole derivatives and use as PI3 kinase inhibitors

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1760080A1 (fr) * 2000-08-17 2007-03-07 Lumera Corporation Conception et synthèse de matériaux optiques non linéaires dérivés du thiophène, destinés à des applications électro-optiques
US6750603B2 (en) 2000-08-17 2004-06-15 Lumera Corporation Second order nonlinear optical chromophores and electro-optic devices therefrom
US7019453B2 (en) 2000-08-17 2006-03-28 Lumera Corporation Polymers having pendant nonlinear optical chromophores and electro-optic devices therefrom
CN1466583A (zh) 2000-08-17 2004-01-07 �¬ 用于电光应用场合的高级nlo物质的设计和合成
US7109355B2 (en) 2000-08-17 2006-09-19 Lumera Corporation Fluorinated π-bridge second order nonlinear optical chromophores and electro-optic devices therefrom
US7161726B2 (en) 2004-11-05 2007-01-09 Lumera Corporation Linear optical modulators and method of linear optical modulation

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991009842A1 (fr) * 1989-12-26 1991-07-11 Allied-Signal Inc. Materiaux electro-optiques et modulateurs de lumiere contenant ces derniers
GB2255336A (en) * 1991-04-29 1992-11-04 Sandoz Ltd Compounds having non - linear optical properties
EP0535490A2 (fr) * 1991-10-01 1993-04-07 BASF Aktiengesellschaft Polymères contenant des colorants azoiques
WO1995002848A1 (fr) * 1993-07-12 1995-01-26 Minnesota Mining And Manufacturing Company Composes azoiques multifonctionnels et polymeres derives de ceux-ci pour l'optique non lineaire

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991009842A1 (fr) * 1989-12-26 1991-07-11 Allied-Signal Inc. Materiaux electro-optiques et modulateurs de lumiere contenant ces derniers
GB2255336A (en) * 1991-04-29 1992-11-04 Sandoz Ltd Compounds having non - linear optical properties
EP0535490A2 (fr) * 1991-10-01 1993-04-07 BASF Aktiengesellschaft Polymères contenant des colorants azoiques
WO1995002848A1 (fr) * 1993-07-12 1995-01-26 Minnesota Mining And Manufacturing Company Composes azoiques multifonctionnels et polymeres derives de ceux-ci pour l'optique non lineaire

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7055151B1 (en) 1998-04-03 2006-05-30 Applied Micro Circuits Corporation Systems and methods for multi-tasking, resource sharing and execution of computer instructions
US8129541B2 (en) 2002-02-28 2012-03-06 Novartis Ag 5-phenylthiazole derivatives and use as PI3 kinase inhibitors

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