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EP0667876A1 - Polymeres anisotropes et procede permettant de les produire - Google Patents

Polymeres anisotropes et procede permettant de les produire

Info

Publication number
EP0667876A1
EP0667876A1 EP94927574A EP94927574A EP0667876A1 EP 0667876 A1 EP0667876 A1 EP 0667876A1 EP 94927574 A EP94927574 A EP 94927574A EP 94927574 A EP94927574 A EP 94927574A EP 0667876 A1 EP0667876 A1 EP 0667876A1
Authority
EP
European Patent Office
Prior art keywords
diisocyanate
diepoxide
hydrogen
anisotropic
formula
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Withdrawn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
EP94927574A
Other languages
German (de)
English (en)
Inventor
Werner Mormann
Christoph Irle
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.)
Europaische Wirtschaftsgemeinschaft (ewg)
Original Assignee
Europaische Wirtschaftsgemeinschaft (ewg)
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 Europaische Wirtschaftsgemeinschaft (ewg) filed Critical Europaische Wirtschaftsgemeinschaft (ewg)
Publication of EP0667876A1 publication Critical patent/EP0667876A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/771—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8125—Unsaturated isocyanates or isothiocyanates having two or more isocyanate or isothiocyanate groups
    • 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
    • C09K19/38—Polymers
    • C09K19/3804—Polymers with mesogenic groups in the main chain
    • 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
    • C09K19/38—Polymers
    • C09K19/3804—Polymers with mesogenic groups in the main chain
    • C09K19/3823—Polymers with mesogenic groups in the main chain containing heterocycles having at least one nitrogen as ring hetero atom

Definitions

  • Anisotropic polymers and a process for their production
  • the invention relates to anisotropic polymers of liquid-crystalline diepoxide and liquid-crystalline diisocyanate and a process for the preparation of these anisotropic polymers, optionally in the presence of catalysts, further comonomers and other customary additives.
  • poly (isocyanurate oxazolidinones) These are usually referred to as poly (isocyanurate oxazolidinones). It is also known that cyclotrimerization of the isocyanates initially results in isocyanurate units which react only at elevated temperature with epoxy groups to form the 5-membered oxazolidinone heterocycle.
  • EP-A-0 252 359 describes the reaction of 4,4'-diisocyanatophenyl benzoate with the 4'-epoxypropoxybenzoic acid 4'-epoxypropoxyphenyl ester.
  • the reaction product is opaque. It has no textures of liquid crystalline phases and only contains reaction products that have crystallized out.
  • EP-A-0 252 359 describes the reaction of 4,4'-diisocyanatophenyl benzoate with the 4'-epoxypropoxybenzoic acid 4'-epoxypropoxyphenyl ester.
  • the reaction product is opaque. It has no textures of liquid crystalline phases and only contains reaction products that have crystallized out.
  • anisotropic polymers are formed by the reaction of different monomers only if the reaction temperature is within the liquid-crystalline range of the starting materials.
  • the object of the invention is to propose a combination of diisocyanates and diepoxides, the implementation of which always provides an anisotropic polymer, and a method which is particularly suitable for producing these anisotropic polymers.
  • R 1 to Rs independently of one another, are hydrogen, halogen, a methyl, ethyl, propyl or butyl radical or R 2 , R 3 , R 4 or R5 is a benzene radical,
  • R 2 to R5 are hydrogen if Ri is not hydrogen
  • R l is hydrogen if R 2 to R5 are not hydrogen, and n 1 to 3, the middle group Z also being a heteroaromatic ring with one or two hetero nitrogen atoms or a cycloaliphatic f ⁇ -ns-l, 4-cyclohexylene
  • Y is a CC single bond, CH 2 or C 2 H 47
  • R l to R5 are the atoms or compounds specified in connection with the formula (I)
  • R (CH 2 ) 6 -NCO where the middle group Z can also be a cycloaliphatic frtms-1,4-cyclohexylene radical.
  • MDI hexamethylene diisocyanate
  • HDI hexamethylene diisocyanate
  • HDI biuret bis- (6-isocyanatohexylaminocarbonyl) - (6-isocyanatohexyl) amine
  • 6-isocyanatohexyl) isocyanurate (l, 3, 5-tris (6-isocyanatohexyl) -2,4,6-trioxo-hexahydro-l, 3,5-triazine).
  • the other monomers represented above in terms of formulas and also their preparation are, inter alia, described in: Mormann, W., Brahm, M., Polymer 43, 187-
  • anisotropic polymers according to the invention have halogen substituents, these are preferably fluorine, chlorine and bromine.
  • the mentioned molar ratio of diepoxide A to diisocyanate B in the anisotropic polymer according to the invention is essential for the desired success. If the ratio falls below 2: 1, this can lead to an unfavorably low crosslinking density. If the value of about 1: 4 is exceeded, this means that the disadvantageous properties of the isocyanurate structures predominate (crystallization, loss of the lc properties). It is particularly advantageous if the molar ratio of diepoxide A to diisocyanate B is about 1: 1 to 1: 1.5.
  • the optimum value n in the formulas (I) and (II), in each case independently of one another, is 1.
  • Z in the formula (I) is a heteroaromatic ring having 1 or 2 hetero nitrogen atoms in the form of a pyridine or pyrimidine Radical or a cycloaliphatic frflns-1,4-cyclohexylene radical in the form of an f ⁇ .. ⁇ s-1,4-cyclohexanedicarboxylic acid radical.
  • the invention also relates to a process for the preparation of the anisotropic polymers of the type described above, optionally in the presence of Catalysts, other comonomers and other conventional additives, which is characterized in that the liquid-crystalline diepoxide A of the formula (I) and the liquid-crystalline diisocyanate B, selected from the group consisting of the diisocyanates (II) to (VII), at a temperature of about 100 to 300 ° C in a molar ratio of about 2: 1 to 1: 4 are implemented.
  • the liquid-crystalline diepoxide A of the formula (I) and the liquid-crystalline diisocyanate B selected from the group consisting of the diisocyanates (II) to (VII)
  • Molar ratio of about 2: 1 to 1: 4 has already been explained above.
  • the temperature range of approximately 100 to 300 ° C should be maintained for the following reasons.
  • the lower temperature limit is determined by the fact that the monomers melt homogeneously. Temperatures that are too low undesirably prevent the formation of the oxazolidinone ring. Exceeding the maximum temperature of 300 ° C would bring no advantage.
  • the temperature range from approximately 150 to 220 ° C. is preferred
  • the preferred catalysts are: tertiary amines (D.
  • Lewis acid-base complexes e.g. B. K. Ashida, Eur. J. Cell.
  • the amount of catalyst is not critical.
  • the catalyst is expediently added in an amount of approximately
  • the anisotropic polymer obtained can be advantageous to subject the anisotropic polymer obtained to post-curing.
  • the procedure is expediently such that curing is carried out, for example, at 150 ° C. for two hours, at 200 ° C. for one hour and at 250 ° C. for one hour.
  • Y and Z each independently of one another, NCO, OCN or O
  • Z additionally an alkyl, alkyloxy, alkyloxycarbonyl or acyloxy radical with a chain length of 1 to 20 carbon atoms, optionally branched,
  • Rl to R5 are the atoms or radicals specified in connection with the formula (I). It is preferred that about 0.1 to 2 moles of comonomer C are used per mole of liquid-crystalline diisocyanate B.
  • reaction conditions of the process according to the invention in particular the temperature control and catalysis, have a significant influence on the properties of the desired anisotropic polymer. Conditions which suppress the formation of isocyanurate groups are preferred.
  • the cyclotrimers of mesogenic diisocyanates formed primarily at low temperatures and unsuitable catalysts are crystalline solids which result from the Precipitate the reaction mixture and continue to react slowly. This
  • the polymers according to the invention have optical anisotropy (a frozen mesophase) if at least one of the two monomers A and B has liquid-crystalline properties. If you prepare a mixture of at least one of the two types of monomer and the catalyst, this mixture melts and initiates the polymerization. Depending on the structure of the monomers, the monomer mixture can be in the optically anisotropic state at the start of the reaction, which state is maintained during the polymerization and after the end of the reaction up to the thermal stability limit (decomposition). Another procedure within the scope of the invention is to carry out the curing at a temperature at which the mixture is isotropic and the anisotropic phase only arises in the course of the polymerization.
  • the catalysts mentioned are known in principle.
  • anisotropic polymers according to the invention have many advantages, such as low thermal expansion and tensile strength in the orientation direction. Because of these advantageous properties, they can be used according to the usual
  • Processing methods are used as construction materials in the production of insulating materials, laminates, composites, coatings and coatings.
  • Example 4 (Anisotropic Network of a Liquid-Crystalline (Diaromatic) Diisocyanate and a Liquid-Crystalline (Triaromatic) Diepoxide)
  • Example 2 a mixture of 5.073 g of methyl hydroquinone bis (4-epoxypropoxybenzoate), 2.985 g of 4,4'-diisocyanatophenyl benzoate and 0.11 g of aluminum trichloride / triphenylphosphine oxide catalyst is prepared. About 0.5 mg of the mixture so represented are below the
  • Example 1 prepared and cured at suitable temperatures:
  • Example 2 a mixture of 5.347 g of hydroquinone-bis- (4- epoxypropoxybenzoate), 1.921 g -Ttms-l, 4-diisocyanatocyclohexane and 0.11 g
  • Aluminum trichloride / triphenylphosphine oxide catalyst produced. About 0.5 mg of the mixture so represented are examined under the polarizing microscope. If the mixture is melted at a temperature of 190 ° C and further treated, it is initially isotropic
  • Example 1 prepared and cured at suitable temperatures:
  • Example 13 (Anisotropic network of mesogenic (triaromatic) bisazomethine diepoxide and non-mesogenic (aromatic-aliphatic) diisocyanate)
  • Example 2 an equimolar mixture of 2.731 l, 4-bis (4-epoxypropoxy-phenylamine) dibenzylidene, 1.597 g of methylene bis (4-isocyanatobenzene) and 0.03 g of aluminum trichloride / triphenylphosphine oxide catalyst is prepared.
  • Example 14 (Anisotropic network of mesogenic (triaromatic) diester diepoxide and non-mesogenic (aromatic-aliphatic) diisocyanate)
  • Example 2 a mixture of 5.63 g of hydroquinone bis (4-epoxypropoxybenzoate), 3.05 g of methylene bis (4-isocyanatobenzene) and 0.11 g of aluminum trichloride / triphenylphosphine oxide catalyst is prepared. About 0.5 mg of the mixture so represented are examined under the polarizing microscope. If the mixture is melted at a temperature of 240 ° C and cooled directly at a heating rate of 20 K / min, the mixture becomes optically anisotropic when a temperature of 220 ° C is reached.
  • Example 15 (Anisotropic network of a diaromatic diisocyanate, a triaromatic diepoxide and a triaromatic dicyanate)
  • Example 1 a mixture of 2.734 g of 4,4'- Diisocyanatobiphenyl, 5.513 g of methyl hydroquinone bis (4-epoxypropoxybenzoate) and 0.480 g of hydroquinone bis (4-cyanatobenzoate) and 0.2 g of aluminum trichloride / triphenylphosphine oxide catalyst.
  • Comparative Example 1 (according to EP 0252 359 A2 (Bayer AG. Det .: Dhein.R .. Müller. H.P ..

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Emergency Medicine (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Materials For Medical Uses (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

L'invention concerne des polymères anisotropes produits à partir d'un diépoxyde (A) de formule (I), dans laquelle: Y désigne O-CH2, CH2 ou une liaison simple C-C; X désigne les éléments structuraux (a), (b), (c), (d), (e) ou (f); R1 à R5 désignent, indépendamment les uns des autres, hydrogène, halogène, un reste méthyle, éthyle, propyle ou butyle; ou bien R2, R3, R4 ou R5 désignent un reste benzène; R2 à R5 désignent hydrogène, si R1 ne représente pas hydrogène; R1 désigne hydrogène, si R2 à R5 sont différents d'hydrogène et n vaut entre 1 et 3; le groupe Z situé au milieu peut être un composé cyclique hétéroaromatique ayant un ou deux atomes d'azote ou bien également un reste trans-1,4-cyclohexylène cycloaliphatique, et d'un diisocyanate B d'une des formules (II) à (VII) où Y désigne O-CH2, CH2 ou une liaison simple C-C; X désigne les éléments structuraux (a), (b), (c) ou (f); n vaut 0 ou 1; R1 à R5 désignent les atomes ou les restes mentionnés dans la définition de la formule (I); le groupe Z situé au milieu peut être un reste trans-1,4-cyclohexylène cycloaliphatique, et R désigne (CH2)6-NCO, le rapport molaire du diépoxyde A au diisocyanate B étant compris approximativement entre 2:1 et 1:4. L'invention concerne en outre un procédé de production de ces polymères anisotropes, procédé selon lequel on fait réagir le diépoxyde A et le diisocyanate B à une température comprise entre environ 100 et 300 DEG C, dans un rapport molaire compris entre environ 2:1 et 1:4. Ces polymères anisotropes présentent une dilatation thermique réduite dans le sens d'orientation et s'utilisent dans la production de matières isolantes, de stratifiés et de revêtements.
EP94927574A 1993-09-08 1994-09-07 Polymeres anisotropes et procede permettant de les produire Withdrawn EP0667876A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
LU88405 1993-09-08
LU88405A LU88405A1 (de) 1993-09-08 1993-09-08 Anisotrope Polymere sowie ein Verfahren zu deren Herstellung
PCT/EP1994/002979 WO1995007308A1 (fr) 1993-09-08 1994-09-07 Polymeres anisotropes et procede permettant de les produire

Publications (1)

Publication Number Publication Date
EP0667876A1 true EP0667876A1 (fr) 1995-08-23

Family

ID=19731440

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94927574A Withdrawn EP0667876A1 (fr) 1993-09-08 1994-09-07 Polymeres anisotropes et procede permettant de les produire

Country Status (8)

Country Link
US (1) US5569727A (fr)
EP (1) EP0667876A1 (fr)
JP (1) JPH07508797A (fr)
CA (1) CA2148936C (fr)
ES (1) ES2079335T1 (fr)
GR (1) GR960300004T1 (fr)
LU (1) LU88405A1 (fr)
WO (1) WO1995007308A1 (fr)

Families Citing this family (15)

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Publication number Priority date Publication date Assignee Title
US5904984A (en) * 1996-10-17 1999-05-18 Siemens Westinghouse Power Corporation Electrical insulation using liquid crystal thermoset epoxy resins
US6657031B1 (en) * 2000-08-02 2003-12-02 Loctite Corporation Reworkable thermosetting resin compositions
JP4745625B2 (ja) * 2003-06-19 2011-08-10 住友化学株式会社 エポキシ化合物およびエポキシ樹脂硬化物
KR101117063B1 (ko) * 2003-06-19 2012-04-16 가부시끼가이샤 히다치 세이사꾸쇼 에폭시 화합물 및 경화 에폭시 수지 제품
JP2005139298A (ja) * 2003-11-06 2005-06-02 Polymatech Co Ltd 異方性エポキシ樹脂硬化物及びその製造方法
JP4619770B2 (ja) * 2003-12-24 2011-01-26 住友化学株式会社 エポキシ化合物および該エポキシ化合物を硬化せしめてなるエポキシ樹脂硬化物
TWI354002B (en) 2003-12-24 2011-12-11 Sumitomo Chemical Co Epoxy compounds and cured epoxy resin obtained by
JP4617838B2 (ja) * 2003-12-25 2011-01-26 チッソ株式会社 液晶性（メタ）アクリレート誘導体およびそれらを含む組成物
US7527746B2 (en) 2005-01-28 2009-05-05 Chisso Corporation Liquid crystal polyfunctional acrylate derivative and polymer thereof
WO2007105808A1 (fr) * 2006-03-15 2007-09-20 Sumitomo Chemical Company, Limited Procédé de cristallisation d'un composé époxy
WO2008065732A1 (fr) * 2006-11-27 2008-06-05 Nippon Polyurethane Industry Co., Ltd. Procédé de production d'un mélange à base d'isocyanate modifié contenant une liaison allophanate et une liaison isocyanurate
JP2008239679A (ja) * 2007-03-26 2008-10-09 Sumitomo Chemical Co Ltd エポキシ樹脂組成物
JP2008266594A (ja) * 2007-03-26 2008-11-06 Sumitomo Chemical Co Ltd エポキシ樹脂組成物
WO2011034114A1 (fr) * 2009-09-17 2011-03-24 住友化学株式会社 Composé diépoxy, procédé de production de celui-ci et composition contenant ledit composé diépoxy
CN115704647B (zh) * 2021-08-10 2024-12-03 爱彼爱和新材料有限公司 一种超临界二氧化碳干燥装置及其应用和超临界二氧化碳干燥方法

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US4377646A (en) * 1975-04-14 1983-03-22 Blount David H Process for the production of foamed poly(epoxy-polyisocyanate)silicate polymers
DE3622613A1 (de) * 1986-07-05 1988-01-14 Bayer Ag Verfahren zur herstellung von polymeren netzwerken mit ueberstrukturen, entsprechende polymere netzwerke und ihre verwendung
DE3628141A1 (de) * 1986-08-19 1988-02-25 Bayer Ag Lineare polyurethan-elastomere und verfahren zu ihrer herstellung
US5189117A (en) * 1990-08-03 1993-02-23 The Dow Chemical Company Polyurethane from epoxy compound adduct
US5314983A (en) * 1992-11-09 1994-05-24 Enichem S.P.A. Process for curing polymerizable liquid compositions based on polyisocyanates and epoxides

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Also Published As

Publication number Publication date
JPH07508797A (ja) 1995-09-28
CA2148936C (fr) 1999-03-16
LU88405A1 (de) 1995-04-05
CA2148936A1 (fr) 1995-03-16
GR960300004T1 (en) 1996-02-29
US5569727A (en) 1996-10-29
WO1995007308A1 (fr) 1995-03-16
ES2079335T1 (es) 1996-01-16

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