EP0365599A1 - Prepolymeres de polyisocyanate prepares a partir de materiaux precurseurs polyaromatiques rigides, et polyurethanes prepares a partir de ces prepolymeres - Google Patents

Prepolymeres de polyisocyanate prepares a partir de materiaux precurseurs polyaromatiques rigides, et polyurethanes prepares a partir de ces prepolymeres

Info

Publication number
EP0365599A1
EP0365599A1 EP88906734A EP88906734A EP0365599A1 EP 0365599 A1 EP0365599 A1 EP 0365599A1 EP 88906734 A EP88906734 A EP 88906734A EP 88906734 A EP88906734 A EP 88906734A EP 0365599 A1 EP0365599 A1 EP 0365599A1
Authority
EP
European Patent Office
Prior art keywords
polyisocyanate
active hydrogen
polyaromatic
containing compound
prepolymer composition
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.)
Ceased
Application number
EP88906734A
Other languages
German (de)
English (en)
Other versions
EP0365599A4 (en
Inventor
Oomman P. Thomas
Earl E. Burt, Iii
Richard D. Peffley
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.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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 Dow Chemical Co filed Critical Dow Chemical Co
Publication of EP0365599A1 publication Critical patent/EP0365599A1/fr
Publication of EP0365599A4 publication Critical patent/EP0365599A4/en
Ceased 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • 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
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8191—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with acetylenic compounds having 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/487—Polyethers containing cyclic groups
    • C08G18/4879—Polyethers containing cyclic groups containing aromatic groups
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8038—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3225
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8054—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38
    • C08G18/8058—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38 with compounds of C08G18/3819
    • 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
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen

Definitions

  • This invention relates to polyisocyanate prepolymers or quasi-prepolymers, and to polyurethane and/or polyurea polymers made therefrom.
  • polymers having widely varying properties can be prepared.
  • polymers having widely varying properties can be prepared.
  • rigid polyurethanes are prepared.
  • flexible polyurethanes are prepared by using relatively high equivalent weight, low functionality precursor materials.
  • blowing agents By using or omitting blowing agents, cellular or noncellular polyurethanes are prepared.
  • polyurethanes can be prepared which are useful in a wide variety of applications. It is common practice to reinforce the polyurethane to give it better properties. For example, in preparing flexible polyurethane foams, it is known to employ dispersions of reinforcing polymer particles in a polyether polyol in order to obtain higher load-bearing and good cell opening. Similarly, the use of reinforcing fibers and fillers is common in noncellular polyurethanes as well.
  • this invention is a liquid prepolymer composition containing free isocyanate groups and which is the reaction product of a stoichioraetric excess of a polyisocyanate and an active hydrogen-containing compound which contains an internal rigid polyaromatic grouping.
  • this invention is a polyurethane and/or polyurea polymer prepared in the reaction of an active hyrogen-containing composition with a liquid prepolymer composition containing free isocyanate groups and which comprises the reaction product of a stoichiometric excess of a polyisocyanate with an polyaromatic active hydrogen-containing compound which contains an internal rigid polyaromatic grouping.
  • a prepolymer composition of this invention to prepare a polyurethane or polyurea provides substantially improved physical properties, particularly load-bearing and/or tensile properties in flexible polyurethane foam.
  • a polyisocyanate-terminated prepolymer composition is used to prepare a polyurethane or polyurea polymer.
  • the prepolymer composition is the reaction product of a stoichiometric excess of a polyisocyanate and an active hydrogen- containing compound which contains an internal rigid polyaromatic grouping (hereinafter "rigid precursor").
  • the internal rigid polyaromatic grouping advantageously has an aspect ratio of at least 2.4.
  • the internal rigid polyaromatic grouping has an aspect ratio of at least 6.4 or can aggregate with other like groups to form a nematic, twisted nematic (cholesteric), or smectic ordering (i.e., liquid crystalline).
  • the rigid precursor compounds used herein are polyphenylene compounds which are soluble in a polyisocyanate. These polyphenylene compounds are advantageously as represented by the structure 1
  • each D is independently an inert substituent group which, when ortho to the -A- linkage, can form a cyclic structure with the -A- linkage and the aromatic rings
  • b is a number from 1 to 10, preferably 1 to 3, more preferably 1 to 2
  • each Z is independently an active hydrogen-containing group, preferably hydroxyl, primary amine or secondary amine
  • each R is independently a divalent radical which is inert to the reaction of the isocyanate-reactive polyphenylene compound with a polyisocyanate
  • A is a covalent bond, a cycloaliphatic diradical, -CH 2 CH 2 - or a rigid linking group, or forms a cyclic structure with the aromatic rings and the groups D ortho to the -A- linkage.
  • each R is an oxyalkylene or polyoxyalkylene diradical. More preferably, each R is an oxypropylene polyoxypropylene, oxyethylene or polyoxyethylene diradical. Most preferably, each R is an oxyalkylene polyoxyalkylene group containing from 1 to 4 repeating oxyethylene or oxypropylene units.
  • the groups D do not undesirably react with the polyisocyanate, undesirably interfere with the reaction of the polyisocyanate with an active hydrogen-containing compound, or destroy the rigid character of the rigid precursor compound.
  • exemplary such groups D include hydrogen, inertly substituted lower alkyl or halogen.
  • the groups D are selected such that the rigid precursor compound is symmetrical.
  • the groups D which are ortho to the -A- linkage can form, together with the -A- linkage, a cyclic structure, particularly a C 5 -C 5 cycloaliphatic structure.
  • rigid precursor compounds examples include adducts of bisphenol with from 2 to 10 moles of pyropylene oxide and/or ethylene oxide, adducts of 3,5,3',5'-tetraraethylbiphenol with from 2 to 10 moles of propylene oxide and/or ethylene oxide and adducts of 3,5,3',5'-tetrahalobiphenol with from 2 to 10 moles of propylene oxide and/or ethylene oxide.
  • the rigid precursor compound can be reacted with a polyisocyanate to form an isocyanate-terminated prepolymer containing an internal rigid moiety.
  • This is advantageously accomplished by combining a stoichiometric excess of the polyisocyanate with the rigid precursor compound.
  • Advantageously from 1 to 50, preferrably from 5 to 40, more preferably from 5 to 25 parts by weight of the rigid precursor compound are combined with 100 parts by weight of the polyisocyanate and caused to react until all of the active hydrogen- containing groups in the rigid precursor compound have reacted.
  • the resulting prepolymer product is a solution or colloidal dispersion of the prepolymer in the polyisocyanate.
  • it is preferred to use a substantially difunctional polyisocyanate, although higher functionality polyisocyanates may also be used.
  • Suitable catalysts include the usual urethane catalysts, including tertiary amine and organometallic catalysts described below.
  • the polyisocyanate used herein is any which has properties suitable for preparing the desired polyurethane.
  • These polyisocyanates include those having aromatically bound isocyanate groups as well as those which contain isocyanate groups bound to aliphatic carbon atoms.
  • aromatic polyisocyanates are preferred over the aliphatic polyisocyanates, as the rigid precursor materials and reaction products thereof with the polyisocyanate are generally more soluble in the aromatic polyisocyanates.
  • Particularly useful aliphatic polyisocyanates include, for example, the hydrogenated derivatives of the foregoing aromatic polyisocyanates, as well as hexamethylene diisocyanate, isophoronediisocyanate and 1,4-cyclohexane diisocyanate.
  • prepolymers and quasi-prepolymers of the foregoing polyisocyanates having an -NCO content of 0.5 to 30 percent by weight are useful herein.
  • a polyurethane is prepared from the polyisocyanate composition of this invention by reacting it with at least one active hydrogen- containing compound.
  • the polyisocyanate is advantageously present in an amount sufficient to provide in the reaction mixture from 70 to 500, preferably from 80 to 150, and more preferably from 95 to 120 isocyanate groups per 100 active hydrogen- containing groups. Higher amounts of the polyisocyanate can be used when the formation of an isocyanurate-containing polymer is desired.
  • noncellular polyurethane and/or polyurea elastomers are prepared by reacting a relatively high equivalent weight active hydrogen- containing compound (preferably 800 to 3000 molecular weight) and a chain extender compound with a polyisocyanate.
  • the chain extender compound advantageously has an equivalent weight of from 31 to 250 and a functionality of form 2 to 4, preferably 2.
  • the chain extender is preferably a glycol or a diamine, with C 2 -C 5 alkylene glycols and stearically hindered aromatic diamines being preferred.
  • a conventional casting process particularly a solventless casting process, or a reaction injection molding process can be employed.
  • Suitable casting techniques are described, for example, in U.S. Patent No. 4,556,703.
  • Reaction injection molding techniques are described, for example, in Sweeney, F. M., Introduction to Reaction Injection Molding, Technomics, Inc., 1979.
  • Suitable formulations/ for use in RIM processes are described, for example in U.S. Patent Nos. 4,269,945, 4,218,610, 4,297,444 and 4,530,941. In these formulations substitution of all or a portion of one or more of the active hydrogen-containing compounds with a liquid crystalline polyol or a liquid crystal dispersion having a similar equivalent weight functionality and reactivity is made.
  • either a one-shot or two-shot (i.e. prepolymer) process can be employed.
  • the two-shot process all or most of the relatively high equivalent weight active hydrogen-containing compound is reacted with an excess of a polyisocyanate to form an isocyanate-terminated prepolymer, which is then reacted with the chain extender and any remaining high equivalent weight material.
  • the one-shot process most or all of the relatively high equivalent weight material is mixed with the chain extender and the mixture is reacted with the polyisocyanate.
  • certain prepolymers and quasi-prepolymers may be employed as the polyisocyanate component even in a one- shot process.
  • the polyurethane and/or polyurea polymer is cellular, i.e. has an unfilled density of less than 0.8 g/cc. More preferably, the polyurethane and/or polyurea is a flexible polyurethane foam.
  • Such flexible polyurethane foam is advantageously prepared by reacting a relatively high equivalent weight polyol with the polyisocyanate composition of this invention in the presence of a blowing agent.
  • a surfactant to stabilize the foaming reaction mass and to compatibilize the various components of the reaction mixture, and to employ various catalysts for both the urethane forming and blowing reactions.
  • a crosslinker such as diethanolamine is often employed to promote rapid initial curing.
  • the major component of the active hydrogen-containing compound(s) used advantageously has an equivalent weight of from 800 to 3000 and an average functionality (defined herein as the number of active hydrogen- containing groups per molecule) of from 2 to 4, more preferably from to 2 to 3.
  • Suitable blowing agent for preparing foams include, for example, water, low boiling halogenated alkanes such as methylene chloride; monochlorodifluoromethane, dichlorodifluoromethane and dichloromonofluoromethane, the so-called "azo" blowing agents, finely divided solids, as well as other materials which generate a gas under the conditions of the foaming reaction.
  • Water, the halogenated methanes or mixtures thereof are preferred.
  • water 0.5 to 10, preferably from 1 to 5 parts by weight are used per 100 parts of active hydrogen-containing compound(s).
  • halogenated alkanes are typically used in an amount of from 5 to 75 parts per 100 parts by weight of active hydrogen- containing compound(s).
  • blowing agents to achieve a desired density is well known in the art, and it may in some instances b e advantageous to use amount of blowing agents outside of the ranges mentioned before.
  • Suitable surfactants include the diverse silicone surfactants, preferably those which are block copolymers of a polysiloxane and a poly(alkylene oxide). Suitable such surfactants include, for example, Y-10184 surfactant, available from Union Carbide Corporation. Surfactants are used in an amount sufficient to stabilize the foaming reaction mixture against collapse until the foam is cured, and to promote the formation of a somewhat uniform cell structure. Typically, from 0.1 to 5, preferably from 0.3 to 3 parts by weight of surfactant are employed per 100 parts of active hydrogen-containing compound( s ) .
  • Crosslinkers which are commonly employed in preparing flexible polyurethane foams include, for example, low equivalent weight alkanolamines such as ethanolamine, diethanolamine, triethanolamine, propanolamine, dipropanolamine, tripropanolamine, methyldiethanol amine and methyl dripopanol amine. Also useful are the alkylene glycols and low equivalent weight hydroxyl-terminated polyols such as glycerine and trimethylol propane. Such crosslinkers are generally used in minor amounts, preferably from 0.2 to 10, more preferably from 0.5 to 5 parts per 100 parts of relatively high equivalent weight active hydrogen- containing compounds.
  • Catalysts for prepared polyurethane and/or polyurea foams include organo- metallic catalysts and tertiary amine compounds.
  • organometallic catalysts organotin catalysts are generally preferred. Suitable catalysts are described, for example, in U.S. Patent No. 4,495,081.
  • an amount sufficient to increase the rate of the urethane-forming (and foaming reactions, when a cellular polymer is formed) is used.
  • an amount sufficient to increase the rate of the urethane-forming (and foaming reactions, when a cellular polymer is formed is used.
  • from 0.001 to 0.5 part of an organometallic catalyst is used per 100 parts of active hydrogen-containing compound( s ) .
  • Tertiary amine-containing compounds are used in an amount ranging from 0.1 to 3 parts per 100 parts of active hydrogen-containing material.
  • alkali metal compounds are useful trimerization catalysts.
  • the foam can be prepared in any convenient manner.
  • the foam can be prepared by reacting the components in a closed mold, or by permitting the reacting components to freely rise. Processes for preparing polyurethane foams are described, for example, in U.S. Patent No. 4,451,588.
  • the polyisocyanate composition of this invention is useful in preparing rigid cellular and noncellular polyurethane and/or polyurea polymers methods for making such materials are described, for example, in U.S. Patent Nos. 4,579,844 and 4,569,951.
  • Rigid polyurethane foams are advantageously prepared using active hydrogen-containing compounds having an equivalent weight of from 31 to 400 and an average functionality of from 3 to 16, preferably from 3 to 8.
  • the polyurethane and/or polyurea polymers of this invention are useful, for example, as seating, cushioning, industrial elastomers, automobile fascia and burners and thermal insulation.
  • a TDI prepolymer was prepared by adding to 100 parts TDI 10 parts of a rigid monomer having the structure
  • the resulting foam Sample No. 1 a contained 3.27 weight percent of the rigid monomer and had properties as indicated in Table 2 following.
  • TDI polymers Three TDI polymers (sample Nos. 3 to 5) were prepared according to the procedure described in
  • Example 1 by reacting 100 parts by weight TDI with 10 parts of rigid monomers represented by the structures:
  • Sample No. 5 Polyurethane foams were prepared each of these prepolymers according to the procedure described in Example 1. The foams had properties as indicated in Table 3 following. For comparison, a foam was prepared using unmodified TDI as the polyisocyanate (comparative Sample B). Its properties are indicated in Table 3. Substantial improvement in load bearing, tear strength and tensile strength are seen with this invention.
  • a TDI prepolymer Sample No. 6 was prepared according to the procedure described in Example 1 by reacting 100 parts by weight TDI with 10 parts of a rigid monomer represented by the structures
  • the prepolymer was used to prepare a polyurethane foam according to the procedure described in Example 1.
  • the foam had properties as indicated in Table 4 following.
  • a foam was prepared using unmodified TDI as the polyisocyante (Comparative Sample C). Its properties are indicated in Table 4. Substantial improvement in load bearing and tensile strength are seen with this invention.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Cette invention concerne une composition prépolymère liquide qui contient des groupes d'isocyanate libres et qui est le produit de réaction d'une quantité stoïchiométrique excessive d'un polyisocyanate et d'un composé contenant de l'hydrogène actif qui contient un groupement polyaromatique interne rigide. Cette invention concerne également des polymères de polyuréthane et/ou de polyurée obtenus à partir de ces compositions prépolymères.
EP19880906734 1987-07-14 1988-07-07 Polyisocyanate prepolymers prepared from rigid polyaromatic precursor materials, and polyurethanes prepared therefrom Ceased EP0365599A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7304687A 1987-07-14 1987-07-14
US73046 1987-07-14

Publications (2)

Publication Number Publication Date
EP0365599A1 true EP0365599A1 (fr) 1990-05-02
EP0365599A4 EP0365599A4 (en) 1990-09-12

Family

ID=22111386

Family Applications (2)

Application Number Title Priority Date Filing Date
EP19880906734 Ceased EP0365599A4 (en) 1987-07-14 1988-07-07 Polyisocyanate prepolymers prepared from rigid polyaromatic precursor materials, and polyurethanes prepared therefrom
EP88111235A Withdrawn EP0299462A3 (fr) 1987-07-14 1988-07-13 Prépolymères de polyisocyanate préparés à partir de matériaux-précurseurs rigides polyaromatiques et polyuréthanes préparés à partir de ceux-ci

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP88111235A Withdrawn EP0299462A3 (fr) 1987-07-14 1988-07-13 Prépolymères de polyisocyanate préparés à partir de matériaux-précurseurs rigides polyaromatiques et polyuréthanes préparés à partir de ceux-ci

Country Status (6)

Country Link
EP (2) EP0365599A4 (fr)
JP (1) JPH02502384A (fr)
KR (1) KR890701657A (fr)
AU (1) AU606737B2 (fr)
BR (1) BR8807617A (fr)
WO (1) WO1989000588A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX163878B (es) * 1988-11-16 1992-06-29 Mobay Corp Procedimiento para la preparacion de prepolimeros de isocianato,liquidos,estables en almacenamiento
JP6138523B2 (ja) * 2013-03-07 2017-05-31 東洋ゴム工業株式会社 液晶ポリウレタンエラストマー及びその製造方法
JP6407580B2 (ja) * 2014-06-20 2018-10-17 旭化成株式会社 エポキシ樹脂及びその組成物、並びに化合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3078257A (en) * 1957-07-06 1963-02-19 Bayer Ag Polyurethane bristles and process for their manufacture
US3330781A (en) * 1962-05-07 1967-07-11 Mobay Chemical Corp Polyurethane plastics prepared from alkylene oxide adducts of compositions comprising a major portion of trihydroxydiphenyl
US4071484A (en) * 1973-10-23 1978-01-31 Kohkoku Chemical Industry Co., Ltd. Process for preparing flexible flame retarding polyurethane foams
GB2100276A (en) * 1981-06-11 1982-12-22 Goldschmidt Ag Th Curable adhesive

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925296A (en) * 1971-10-26 1975-12-09 Hooker Chemicals Plastics Corp Foundry aggregate binders
US3795636A (en) * 1972-01-12 1974-03-05 Quaker Oats Co Process for the preparation of polyurethane foams and microcellular elastomers with integral skins and polyol extender system for the preparation thereof
SU523643A3 (ru) * 1973-03-09 1976-07-30 Байер Аг, (Фирма) Способ получени полиуретанмочевины в высокодисперсном виде
JPS5216596A (en) * 1975-07-31 1977-02-07 Kao Corp Process for preparing amphoteric polyurethane emulsions
DE2811148A1 (de) * 1978-03-15 1979-09-20 Bayer Ag Verfahren zur herstellung von waessrigen polyurethan-dispersionen und -loesungen
US4238580A (en) * 1978-05-19 1980-12-09 General Electric Company Process of forming urethane-coupled polymers of quinone-coupled polyphenylene oxides
DE2843790A1 (de) * 1978-10-06 1980-04-17 Bayer Ag Verfahren zur herstellung von waessrigen dispersionen oder loesungen von polyurethan-polyharnstoffen, die nach diesem verfahren erhaeltlichen dispersionen oder loesungen, sowie ihre verwendung
JPS5645965A (en) * 1979-09-25 1981-04-25 Asahi Denka Kogyo Kk Heat-curing composition for coat
JPS5674144A (en) * 1979-11-21 1981-06-19 Takeda Chem Ind Ltd Preparation of polyurethane emulsion
JPS56112976A (en) * 1980-02-08 1981-09-05 Takara Kenzai Seisakusho:Goushi Flexible floor coating material comprising room temp. curable antistaining polyurethane resin
US4366193A (en) * 1981-04-10 1982-12-28 Ashland Oil, Inc. Catechol-based vapor permeation curable coating compositions
JPS591521A (ja) * 1982-06-25 1984-01-06 Sanyo Chem Ind Ltd プライマ−組成物
JPS5980426A (ja) * 1982-10-29 1984-05-09 Asahi Glass Co Ltd ポリウレタン系エラストマ−の製造方法
JPS59179573A (ja) * 1983-03-30 1984-10-12 Nippon Urethane Service:Kk 熱硬化性接着剤用樹脂組成物
JPS59215310A (ja) * 1983-05-23 1984-12-05 Sanyo Chem Ind Ltd 湿気硬化型ウレタン組成物の製造法
DE3401166A1 (de) * 1984-01-14 1985-07-18 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von urethanmodifizierten polyisocyanat-zubereitungen und ihre verwendung bei der herstellung von polyurethankunststoffen
US4522979A (en) * 1984-02-17 1985-06-11 Mobay Chemical Corporation Molding compositions having an enhanced resistance to gasoline
JPS60173010A (ja) * 1984-02-17 1985-09-06 Toyo Tire & Rubber Co Ltd 耐熱、耐摩擦、耐摩耗性ポリウレタン樹脂組成物
US4569951A (en) * 1985-01-18 1986-02-11 The Dow Chemical Company Polymers prepared by reaction of a polyisocyanate with a secondary amine terminated adduct of a primary amine compound and a polyepoxide
US4645816A (en) * 1985-06-28 1987-02-24 Union Carbide Corporation Novel vulcanizable silane-terminated polyurethane polymers
JPH0686113B2 (ja) * 1985-11-27 1994-11-02 凸版印刷株式会社 レーザ製版装置
US4745137A (en) * 1986-06-25 1988-05-17 The Dow Chemical Company Polyurethanes prepared from solutions or dispersions of polymers of rigid polyaromatic monomers in polyols
US4745135A (en) * 1986-06-25 1988-05-17 The Dow Chemical Company Polyurethanes prepared from liquid crystal-containing polyols
US4701475A (en) * 1986-06-25 1987-10-20 The Dow Chemical Company Polyurethanes reinforced with rigid rod micro fillers
US4745136A (en) * 1986-06-25 1988-05-17 The Dow Chemical Company Polyurethanes prepared from dispersions or solutions of cholesterol or cholestanol-containing polymers in a polyol
SE460958B (sv) * 1986-10-02 1989-12-11 Kh Gol Sp Proizvodstvennogkhar Verktyg foer skaerning av yttergaengor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3078257A (en) * 1957-07-06 1963-02-19 Bayer Ag Polyurethane bristles and process for their manufacture
US3330781A (en) * 1962-05-07 1967-07-11 Mobay Chemical Corp Polyurethane plastics prepared from alkylene oxide adducts of compositions comprising a major portion of trihydroxydiphenyl
US4071484A (en) * 1973-10-23 1978-01-31 Kohkoku Chemical Industry Co., Ltd. Process for preparing flexible flame retarding polyurethane foams
GB2100276A (en) * 1981-06-11 1982-12-22 Goldschmidt Ag Th Curable adhesive

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO8900588A1 *

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WO1989000588A1 (fr) 1989-01-26
EP0299462A2 (fr) 1989-01-18
AU606737B2 (en) 1991-02-14
AU2139088A (en) 1989-02-13
EP0365599A4 (en) 1990-09-12
EP0299462A3 (fr) 1989-01-25
JPH02502384A (ja) 1990-08-02
BR8807617A (pt) 1990-06-12
KR890701657A (ko) 1989-12-21

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