EP0303644A1 - Composition de formation de liaisons hydrogene - Google Patents

Composition de formation de liaisons hydrogene

Info

Publication number
EP0303644A1
EP0303644A1 EP88901585A EP88901585A EP0303644A1 EP 0303644 A1 EP0303644 A1 EP 0303644A1 EP 88901585 A EP88901585 A EP 88901585A EP 88901585 A EP88901585 A EP 88901585A EP 0303644 A1 EP0303644 A1 EP 0303644A1
Authority
EP
European Patent Office
Prior art keywords
nonlinear optical
order
materials
polymer
hydrogen bonds
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.)
Withdrawn
Application number
EP88901585A
Other languages
German (de)
English (en)
Inventor
Dieter Dorsch
Rudolf Eidenschink
Bernhard Rieger
Gerd Marowsky
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP0303644A1 publication Critical patent/EP0303644A1/fr
Withdrawn legal-status Critical Current

Links

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
    • G02F1/37—Non-linear optics for second-harmonic generation
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph

Definitions

  • the invention relates to nonlinear optical materials in which a component with a layer 5 containing second order hyperpolarizability other than zero is bonded to a substrate via hydrogen bonds.
  • Nonlinear optics deals with the interaction of electromagnetic fields in different media and the associated creation of new fields with changed properties. Materials with non-linear
  • Electro-optical switches, frequency and intensity control in laser technology, holography and the areas of information processing and integrated optics represent areas of application for materials with non-linear optical properties of the second order.
  • Materials with 3rd order electrical susceptibility functions are suitable for the production of purely optical switches and thus as waveguides for the construction of purely optical computers.
  • Crystal requires technical usability values as high as possible for the dielectric susceptibility X (2) '.
  • inorganic substances such as Potassium dihydrogen phosphate or lithium niobate shows non-linear optical properties.
  • all of these connections have various disadvantages.
  • inorganic compounds In addition to inadequate values for the dielectric susceptibility of the second order, inorganic compounds often lack sufficient photostability when treated with high light intensities, or they are difficult to manufacture and process.
  • Organic compounds of the nitroaniline type are known from Garito et al., Laser Focus 18_ (1982) and EP-0091 838.
  • their relatively good values for the photochemical stability and the dielectric susceptibility of the second order go hand in hand with poor crystallizability and poor mechanical stability.
  • the production of thin layers, as required by the integrated optics does not succeed with these materials.
  • Polymers are characterized by high mechanical resistance and good chemical stability. Molecules with non-linear optical properties attached to the polymer structure or dissolved in polymers should therefore have advantageous values for the dielectric susceptibility in the non-centrosymmetric environment.
  • Polymers with second-order nonlinearities can be produced by applying an external field to films heated to above the glass temperature and doped with statistically oriented molecules. This leads to polarity of the embedded molecules, which gives the polymer medium an anisotropy after it solidifies.
  • Polymers produced in this way with nonlinear optical properties, in which p, p'-dimethylaminonitrostilbene is used as the host molecule, have been described by Meredith et al., Macromolecules 1J5 (1982) 1385.
  • US Pat. No. 4,412,059 discloses a polymer material with cholesteric mesophases which are accessible for controlled alignment by means of electrical or magnetic fields.
  • EP-0172012 discloses fully aromatic, thermotropic, liquid-crystalline polymers, the nonlinear optical properties of which can also be caused by external fields.
  • Another method for producing polymer materials with nonlinear optical properties consists in the polymerization of monomers which have already been ordered and have a noncentrosymmetric orientation, where the orderly state of the system is largely preserved during the polymerization.
  • Monomers suitable for this technique can be found, for example, in EP-0021695.
  • DE-Al-36 24858 describes polymer materials with nonlinear optical properties which consist of polar monomer units and whose main polymer chains have an orientation perpendicular to the substrate surface.
  • the production of such polymer materials requires chemical anchoring on the substrate surface either of the initiator which triggers the polymerization or of the polymerized monomers, which necessitates an additional process step.
  • the invention therefore relates to a hyperpolarizability which is applied to a surface and consists of at least one component with a non-zero polarizability 2nd order existing, nonlinear optical material, characterized in that the components with a non-zero hyperpolarizability of 2nd order are bound to the substrate surface via hydrogen bonds and one or more subsequent layers lying over the substrate cover layer are also connected to one another via hydrogen bonds are bound.
  • the invention also relates to the use of these materials as nonlinear optical media.
  • Suitable compounds according to the invention which form hydrogen bonds are, for example, the compounds listed in Hamilton, Ibers, loc. Cit. They are preferably dipolar substituted, in particular donor substituents, such as, for example, hydroxy, alkoxy, amino, mono- and dialkylamino, and acceptor substituents, such as, for example, cyano, nitro, carboxyl, alkoxycarbonyl and nitrogen in aromatic systems, being suitable.
  • donor substituents such as, for example, hydroxy, alkoxy, amino, mono- and dialkylamino
  • acceptor substituents such as, for example, cyano, nitro, carboxyl, alkoxycarbonyl and nitrogen in aromatic systems, being suitable.
  • the nitrogen-containing six-ring compounds described in DE-Al-36 41 024 are particularly suitable components for the production of the nonlinear optical materials according to the invention.
  • Suitable substrates for the formation of hydrogen bonds are e.g. Glass, quartz, plastics, in particular those with polar end groups such as polyvinyl alcohol or modified metal surfaces. These substrates can also be functionalized, e.g. in the by Deschler et al., Angew. Chem. 98_ (1986) 237, described using reactive silanes.
  • Substrates coated in this way with materials with a non-zero hyperpolarization have a preferably dipolar orientation of the layer components.
  • the subsequent layers therefore preferably experience the same dipolar orientation as the substrate cover layer.
  • liquid-crystalline substances Because of their ability to be able to form ordered phases in the liquid state, liquid-crystalline substances have also proven to be suitable for producing the nonlinear optical materials according to the invention. Such liquid-crystal compounds with one or more of the above-mentioned donor and / or acceptor substituents are particularly suitable for this purpose.
  • polymers capable of forming hydrogen bonds with a non-zero hyperpolarizability are also suitable for producing the nonlinear optical materials according to the invention.
  • the polymer dressing may already be present on the substrate prior to application, or a material provided with groups capable of polymerization is first applied to the substrate and then polymerized while maintaining the nonlinear optical properties.
  • the polymerization can in both cases, for example, according to that in CM. Paleos et al., J. Poly. Be. Polym. Chem. Ed., 19_ (1981) 1427, or Ocian: Principles of Polymerization, McGraw-Hill, New York.
  • compositions forming hydrogen bridges according to the invention are outstandingly suitable as nonlinear optical media. They are manufactured e.g. by applying the above-mentioned compounds to a substrate in dissolved or liquid form, for example by brushing, printing, dipping or spin coating. In this way, nonlinear optical arrangements are obtained which, because of their advantageous properties, open up a wide field of application. In particular, they are suitable for doubling the frequency of laser light and for producing switching elements, waveguides and phase modulators in the field of integrated optics.
  • a glass layer is coated with a thin layer of this compound by immersion in a concentrated solution of 4- ⁇ 2- [4 * - (6-hydroxyhexyloxy) biphenyl-4 l -yl] ethenyl ⁇ pyridine in dichloromethane.
  • the layer obtained shows good nonlinear optical properties.
  • N-methylpyrrolidone is kept at 60 ° C. for 20 hours.
  • the polymer is reprecipitated twice from ethanol.
  • a yellow powdery polymer is obtained.
  • the polymer is dissolved in N-methylpyrrolidone and applied to a glass substrate by spin coating.
  • a transparent, yellowish polymer film is obtained which has waveguide properties and non-linear optical properties of the second order. The frequency of light that is guided in this polymer film is thus partially doubled in frequency.
  • a glass plate is coated with a layer of the monomer and photoinitiator by immersion in a solution of the monomer prepared according to Example 4 and a photoinitiator (e.g. 2-hydroxy-2-methyl-l-phenylbutan-l-one). At a temperature of 100 ° C this layer is irradiated with UV light. The result is a transparent yellow polymer film with non-linear optical properties.
  • a photoinitiator e.g. 2-hydroxy-2-methyl-l-phenylbutan-l-one

Landscapes

  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

Des compositions de formation de liaisons hydrogène conviennent à la fabrication de matériaux optiques non-linéaires.
EP88901585A 1987-02-17 1988-02-08 Composition de formation de liaisons hydrogene Withdrawn EP0303644A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19873704878 DE3704878A1 (de) 1987-02-17 1987-02-17 Wasserstoffbruecken ausbildende zusammensetzungen
DE3704878 1987-02-17

Publications (1)

Publication Number Publication Date
EP0303644A1 true EP0303644A1 (fr) 1989-02-22

Family

ID=6321099

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88901585A Withdrawn EP0303644A1 (fr) 1987-02-17 1988-02-08 Composition de formation de liaisons hydrogene

Country Status (6)

Country Link
US (1) US5035839A (fr)
EP (1) EP0303644A1 (fr)
JP (1) JPH01502539A (fr)
KR (1) KR890700851A (fr)
DE (1) DE3704878A1 (fr)
WO (1) WO1988006304A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE68928746T2 (de) * 1988-09-08 1999-03-11 Akzo Nobel N.V., Arnheim/Arnhem Integrierte optische Bauteile
FR2653908A1 (fr) * 1989-10-26 1991-05-03 Alsthom Cge Alcatel Materiau organique pour l'optique non lineaire et les dispositifs electro-optiques.
FR2671553B1 (fr) * 1991-01-10 1993-04-30 Hoechst France Nouvelles molecules metallo-organiques non-centrosymetriques, procede de preparation et application en optique non-lineaire et des intermediaires.
US8383565B2 (en) 2005-11-17 2013-02-26 Sunnyside Corporation Color changing paint and varnish remover

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199698A (en) * 1978-12-08 1980-04-22 Bell Telephone Laboratories, Incorporated 2-Methyl-4-nitro-aniline nonlinear optical devices
US4431263A (en) * 1979-06-25 1984-02-14 University Patents, Inc. Novel nonlinear optical materials and processes employing diacetylenes
FR2520360A1 (fr) * 1982-01-26 1983-07-29 Nicoud Jean Nouveaux derives de la paranitroaniline utilisables en optique non lineaire et en electro-optique et leur procede de preparation
US4610681A (en) 1985-05-31 1986-09-09 Kimberly-Clark Corporation Disposable underpants having discrete outer seals
US4774025A (en) * 1985-06-25 1988-09-27 Hoechst Celanese Corporation Nonlinear optical medium of a naphthoquinodimethane compound
US4868250A (en) * 1986-01-24 1989-09-19 Hoechst Celanese Corp. Polysiloxane polymers exhibiting nonlinear optical response
GB8602708D0 (en) * 1986-02-04 1986-03-12 Ici Plc Non-linear optics
GB8602705D0 (en) * 1986-02-04 1986-03-12 Ici Plc Non-linear optical device
US4719281A (en) * 1986-04-21 1988-01-12 Hoechst Celanese Corporation Pendant quinodimethane-containing polymer
US4775215A (en) * 1986-10-31 1988-10-04 Hoechst Celanese Corporation Nonlinear optical devices
US4940464A (en) 1987-12-16 1990-07-10 Kimberly-Clark Corporation Disposable incontinence garment or training pant
US5171239A (en) 1989-08-10 1992-12-15 Uni-Charm Corporation Disposable garments
US5167897A (en) 1991-02-28 1992-12-01 The Procter & Gamble Company Method for incrementally stretching a zero strain stretch laminate web to impart elasticity thereto
US5246433A (en) 1991-11-21 1993-09-21 The Procter & Gamble Company Elasticized disposable training pant and method of making the same
SE508409C2 (sv) 1992-03-04 1998-10-05 Sca Hygiene Prod Ab Absorberande blöjbyxor
US5569234A (en) 1995-04-03 1996-10-29 The Procter & Gamble Company Disposable pull-on pant
WO1998005895A1 (fr) 1996-08-05 1998-02-12 Abey Australia Pty. Ltd. Organes de soutien reglables

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8806304A1 *

Also Published As

Publication number Publication date
KR890700851A (ko) 1989-04-27
WO1988006304A1 (fr) 1988-08-25
US5035839A (en) 1991-07-30
DE3704878A1 (de) 1988-08-25
JPH01502539A (ja) 1989-08-31

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