EP0000917A1 - L'utilisation du 1,1,1,-trifluoro-2-chloréthane comme agent gonflant dans la préparation de mousses plastiques - Google Patents

L'utilisation du 1,1,1,-trifluoro-2-chloréthane comme agent gonflant dans la préparation de mousses plastiques Download PDF

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Publication number
EP0000917A1
EP0000917A1 EP78100668A EP78100668A EP0000917A1 EP 0000917 A1 EP0000917 A1 EP 0000917A1 EP 78100668 A EP78100668 A EP 78100668A EP 78100668 A EP78100668 A EP 78100668A EP 0000917 A1 EP0000917 A1 EP 0000917A1
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Prior art keywords
blowing agent
foams
production
groups
chloroethane
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EP78100668A
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German (de)
English (en)
Inventor
Karl-Heinz Dr. Mitschke
Hans Dr. Niederprüm
Manfred Dr. Kapps
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only

Definitions

  • the present invention relates to a process for the production of foamed plastics, preferably based on polyisocyanate, in particular polyurethane foams, using 1,1,1-trifluoro-2-chloroethane, optionally in a mixture with 1,1-difluoro-1,2-dichloroethane.
  • foamed plastics e.g. of polyurethanes with the aid of blowing agents based on chlorofluorocarbons is known per se (cf. e.g. DT-PS 1 045 644).
  • Chlorofluorocarbon blowing agents especially trichlorofluoromethane (R11) and, to a lesser extent, dichlorodifluoromethane (R12) and 1,1,2-trichlorotrifluoroethane (R113), are of great technical importance because they allow, for example, hard polyurethane foams with 90 to 95% closed cells to manufacture.
  • the R 11 enclosed in the cells remains essentially therein and, because of the favorable physical properties, results in a foam with very little heat conductivity (see O. Scherer, technical organic fluorine compounds, Progress Chem.Forsch., vol. 14/2, p. 147 (1968)).
  • Such hard polyurethane foams are used primarily as heat-cold insulation agents in refrigeration units, cold rooms, pipelines, containers and components, as well as packaging material and as surface protection. In particular, the trend towards energy-saving construction through better insulation allows this area to expand further.
  • Halogen alkanes suitable as propellants must have certain properties such as a suitable boiling point or vapor pressure, solubility or dispersibility in one of the reaction components, for example the polyester or polyether, low thermal conductivity, toxicological harmlessness, chemical inertness, non-flammability, low diffusion rate and prevention of the shrinkage of the foam or avoid swelling of the cell walls.
  • the fluorochloroalkanes mentioned also produce polyolefin, polystyrene and phenolic resin-based foams, using a wide variety of techniques, e.g. Direct foaming, pre-foaming (Frothing method), direct gas injection process in the extruder (see e.g. company publication "Kaltron, the blowing agent for foams", Kali-Chemie AG, Hanover (1976)).
  • a process has now been found for the production of foamed plastics, in particular polyurethane foams, which completely satisfies the need mentioned, in which the propellant is 1,1,1-trifluoro-2-chloroethane, optionally in a mixture with 1.1 -Difluoro-1,2-dichloroethane can be used.
  • the present invention relates to a process for the production of foamed plastics by reacting starting materials which react to form high molecular weight plastics in the sense of a polymerization, polycondensation or polyaddition reaction in the presence of blowing agents or foaming of a non-foamed, thermoplastic material known per se with the aid of a blowing agent , characterized in that the propellant used is 1,1,1-trifluoro-2-chloroethane, optionally in a mixture with 1,1-difluoro-1,2-dichloroethane.
  • 1,1,1-trifluoro-2-chloroethane (R 133a), optionally in a mixture with 1,1-difluoro-1,2-dichloroethane (R 132), is very good as a blowing agent for the Production of foamed plastics, especially for those based on polyurethane, is suitable.
  • the quality of the foams produced with it essentially corresponds to the products conventionally produced, for example with CFC1 3 (R 11).
  • R 133a and R 132 are non-flammable and physiologically harmless according to all previous investigations (cf. e.g., bark Chemie undtechnik 24, 1976, p. 307 and Aerosol Age, January 1977, p. 9). Both substances are under the one flow of light is easily degradable.
  • the tropospheric lifespan of 133a is only 6.1 years (von Schweinichen, Aerosol Report, April 1977, pp. 172-180). It should also be taken into account here that R 133a has only one chlorine atom, but the conventionally most commonly used R 11 has three chlorine atoms.
  • CFCl 3 decomposes at 0.04% (from the resulting Cl- ) after 24 hours of irradiation (Osram Ultra Vitalux lamps) with a radiation mixture that roughly corresponds to natural sunlight at a height of several thousand meters. Ion quantities determined) or 0.13% (determined from resulting F ion quantities). In contrast, the degree of decomposition for CF3CH2Cl is 53% and 46%.
  • R 133a is easy to produce in high yields and in excellent purity (greater than 99.99%) by catalytic liquid phase fluorination of unstabilized trichlorethylene, a cheap mass product, just like the preliminary product R 132 (DT-OS 2 719 021).
  • R 133a has high thermal and chemical stability, for example against hydrolytic influences and nucleophilic attacks (for example of OH ions or amines).
  • a specially stabilized quality as is required when using R 11 in the context of polyurethane foaming, in cases where premixed systems of polyols, amine-based catalysts, silicone stabilizers and blowing agents are stored for a long time before the actual foaming the use of R 133a (or R 132) is not necessary (see LM Zwolinski, Rubber Age, July 1975, p. 54).
  • Amine-based polyols can also be processed with the help of the new blowing agents.
  • the foams are produced in a manner known per se (cf. Houben-Weyl, Methods of Organic Chemistry, Vol. XIV / 2, p. 88 (1963); High Polymers, Vol. XVI "Polyurethanes Chemistry and Technology, written by Saunders - Fresh, Interscince Publishers, New York / London, 1962/1964; Plastics Handbook, Volume VII, Vieweg-Höchtlen, Carl-Hanser-Verlag Kunststoff, 1966).
  • the process according to the invention is suitable for producing a wide variety of cellular and porous materials, in particular for producing foams from plastics.
  • the plastics can be produced by polymerization, polyaddition or else by polycondensation.
  • plastics which may be mentioned are: polyolefins, such as, for example, polyethylene or polypropylene, polystyrene, polyethylene styrene, polyamide, polycarbonate, polysulfone, Polyethylene terephthalate, polybutylene terephthalate, polyphenyllenoxide, polymethacrylate, polymethacrylonitrile, polyacrylonitrile, polyethylene, polyvinyl chloride, plastic based on cellulose esters, copolymers from the components listed above, acrylonitrile-butadiene-styrene polymers (ABS), mixtures of polysulphonitrile and styrene-polysulphonitrile and styrene-ABS Polymers, mixtures
  • foams can also be produced from inorganic-organic plastics, such as, for example, in FR-PS 1 419 552, FR-PS 1 362 003, DT-OS 1 770 384, DT-OS 2 227 147, DT-OS 2 310 559 , DT-OS 2 325 090, DT-OS 2 359 610, DT-OS 2 359 607, DT-OS 2 359 606, DT-OS 2 359 608, DT-OS 2 359 609 and DT-OS 2 359 612 become.
  • inorganic-organic plastics such as, for example, in FR-PS 1 419 552, FR-PS 1 362 003, DT-OS 1 770 384, DT-OS 2 227 147, DT-OS 2 310 559 , DT-OS 2 325 090, DT-OS 2 359 610, DT-OS 2 359 607, DT-OS 2 359 606, DT-OS 2 3
  • the blowing agent according to the invention is preferably added in amounts of from 0.01 to 40, particularly preferably from 0.1 to 30,% by weight, based on the plastic, or based on the reaction mixture reacting to the plastic.
  • any other amount familiar to the person skilled in the art can also be added. The particular addition depends in each case on the requirements which the person skilled in the art places on the object to be foamed.
  • the blowing agent according to the invention can also be used in combination with known auxiliaries such as nucleating agents or nucleating agents (for example talc, MgC0 3 , CaCO 3 , ZnC0 3 , CaS0 4 , NaHC0 3 , polytetrafluoroethylene powder, polyhexafluoropropylene powder), fillers (for example glass fibers, CaC0 3 , MgC0 3 , chalk, kaolin, Ti0 2 ), lubricants (e.g. waxes, paraffins, fatty acid esters), stabilizers (e.g. UV absorbers, light and heat stabilizers), adhesion promoters (e.g.
  • nucleating agents or nucleating agents for example talc, MgC0 3 , CaCO 3 , ZnC0 3 , CaS0 4 , NaHC0 3 , polytetrafluoroethylene powder, polyhexafluoropropylene powder
  • fillers for example glass fibers
  • paraffin oil paraffin oil, plasticizers, butyl stearate, resin solutions
  • vehicle materials e.g. Si0 28 MgO, ZnO, ZnC03
  • peroxides pigments, dyes, antioxidants and / or antiozonants are used.
  • the process according to the invention is therefore suitable for the production of any foams in which "physical blowing agents" have hitherto been used, ie in which the effect of the blowing agent is due to the evaporation of a volatile inert liquid
  • the known foams based on polyisocyanate are particularly accessible, and the known polyurethane foams are particularly preferred.
  • the foams based on polyisocyanate include, in particular, foams containing isocyanurate groups, which are produced by known trimerization of organic Polyisocyanates are obtained during the reaction leading to the foam, foams containing carbodiimide groups, such as are produced in a manner known per se by condensation of isocyanate groups with formation of carbodiimide during the display m-leading reaction are obtained, mixed types (isocyanurate and carbodiimide groups and optionally containing urethane groups) such as those obtained by reacting polyisocyanates with inadequate amounts of polyhydroxy compounds with simultaneous use of trimerization catalysts and / or carbodiimidization catalysts, and organo-inorganic foams such as those obtained by reaction polyisocyanates with alkali silicate solutions and / or dispersions, optionally with the use of additives, can be obtained from the publications already mentioned.
  • examples of these are 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, mixtures consisting of these isomers, 4,4 1- diisocyanatodiphenylmethane, 2,4 1- diisocyanatodiphenylmethane, these isomers and higher homologs of these diisocyanates-containing polyisocyanate mixtures of the diphenylmethane series, as described in are accessible in a manner known per se by phosgenation of aniline / formaldehyde condensates, and diphenylmethane diisocyanates containing carbodiimide and / or urethonimine groups, as are accessible according to German Patent 1,092,007 (US Pat.
  • Polyisocyanates such as are obtainable by reacting 1 mol of 4,4-diisocyanatodiphenylmethane with 0.05 to 0.3 mol of low molecular weight diols or triols, preferably polypropylene glycols with a molecular weight below 700. Mixtures of the latter preferred polyisocyanates are also preferably used.
  • Starting components to be used according to the invention are furthermore, where appropriate, compounds having at least two hydrogen atoms which are reactive toward isocyanates and have a molecular weight as a rule from 62 to 10,000.
  • These include, in addition to compounds containing amino groups, thiol groups or carboxyl groups, are preferred wise polyhydroxyl compounds, in particular compounds having 2 to 8 hydroxyl groups, especially those having a molecular weight of 200 to 10,000, preferably 1000 to 6000, for example at least 2, usually 2 to 8, but preferably 2 to 4, hydroxyl groups-containing polyesters, polyethers, polythioethers, polyacetals , Polyester amides as are known per se for the production of homogeneous and cellular polyurethanes.
  • the higher molecular weight polyhydroxyl compounds mentioned are often advantageously used in the process according to the invention in a mixture with up to 95, preferably up to 50% by weight, based on the total amount of polyhydroxyl compounds, of low molecular weight polyols of the molecular weight range 62 to 200.
  • Such low molecular weight polyols are, for example, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, 1,6-hexanediol, 1,10-decanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol , Tripropylene glycol, glycerin, trimethylolpropane and the like.
  • the polyethers which come into question according to the invention and have at least 2, generally 2 to 8, preferably 2 to 3, hydroxyl groups are those of the type known per se and are obtained, for example, by polymerizing epoxides, such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin with itself, for example in Presence of BF 3 , or by addition of these epoxides, optionally in a mixture or in succession, to starting components with reactive hydrogen atoms, such as alcohols or amines, e.g. B.
  • epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin
  • reactive hydrogen atoms such as alcohols or amines, e.g. B.
  • sucrose polyether such as z. B. are described in German interpretations 1 176 358 and 1064 938, come into question according to the invention. In many cases, those polyethers are preferred which predominantly (up to 90% by weight, based on all OH groups present in the polyether) have primary OH groups. Also modified by vinyl polymers polyethers such as z. B. by polymerization of styrene, acrylonitrile in the presence of polyethers (US Pat. Nos. 3,383,351, 3,340,273, 3,523,093, 3,110,695, German Patent 1,152,536) are also suitable, as are OH groups-containing polybutadienes .
  • polythioethers the condensation products of thiodiglycol with themselves and / or with other glycols, dicarboxylic acids, formaldehyde, aminocarboxylic acids or amino alcohols are mentioned in particular.
  • the products are polythio ether, polythio ether ester, polythio ether ester amide.
  • polyacetals such. B. from glycols, such as diethylene glycol, triethylene glycol, 4,4'-dioxethoxy-diphenyldimethyltethane, hexanediol and formaldehyde compounds in question.
  • glycols such as diethylene glycol, triethylene glycol, 4,4'-dioxethoxy-diphenyldimethyltethane, hexanediol and formaldehyde compounds in question.
  • Polyacetals suitable according to the invention can also be prepared by polymerizing cyclic acetals.
  • Suitable polycarbonates containing hydroxyl groups are those of the type known per se, which, for. B. by reacting diols, such as propanediol (1,3), butanediol (1,4) and / or hexanediol (1,6), diethylene glycol, triethylene glycol, tetraethylene glycol with diaryl carbonates, e.g. B. diphenyl carbonate or phosgene can be produced.
  • diols such as propanediol (1,3), butanediol (1,4) and / or hexanediol (1,6)
  • the polyester amides and polyamides include e.g. B. the predominantly linear condensates obtained from polyvalent saturated and unsaturated carboxylic acids or their anhydrides and polyvalent saturated and unsaturated amino alcohols, diamines, polyamines and their mixtures.
  • Polyhydroxyl compounds that already contain urethane or urea groups and optionally modified natural polyols, such as castor oil, carbohydrates, starch, can also be used.
  • Addition products of alkylene oxides on fhenol-formaldehyde resins or also on urea-formaldehyde resins can also be used according to the invention.
  • the reactants are preferably used in proportions which correspond to an NCO index of 70 to 800, preferably 90 to 130.
  • the NCO index 100 means the presence of equivalent amounts of isocyanate groups and active hydrogen atoms which react with these isocyanate groups in the reaction mixture).
  • organic blowing agents come e.g. Acetone, ethyl acetate, halogen-substituted alkanes degradable in the stratosphere, such as methylene chloride, chloroform, ethylidene chloride, vinylidene chloride, butane, hexane, heptane or diethylate also come into question.
  • organic blowing agents come e.g. Acetone, ethyl acetate, halogen-substituted alkanes degradable in the stratosphere, such as methylene chloride, chloroform, ethylidene chloride, vinylidene chloride, butane, hexane, heptane or diethylate also come into question.
  • azeotropic mixtures of the blowing agents essential to the invention with other environmentally friendly blowing agents of the type mentioned by way of example are used as blowing agents, so as to adapt the boiling point of the blowing agent to the particular intended use.
  • organic metal compounds especially organic tin compounds such as e.g. Tin (II) acetate, Tin (II) octoate, Tin (II) ethylhexoate and Tin (II) laurate and the dialkyltin salts of carboxylic acids such as e.g. Dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate or dioctyltin diacetate.
  • organic tin compounds such as e.g. Tin (II) acetate, Tin (II) octoate, Tin (II) ethylhexoate and Tin (II) laurate and the dialkyltin salts of carboxylic acids such as e.g. Dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate or dioctyltin diacetate.
  • the method according to the invention can be used with the known compounds which catalyze the trimerization of isocyanates can also be modified in such a way that polyurethane foams containing isocyanurate groups are formed.
  • NCO key figures are used which are substantially above 100, since free isocyanate groups must not only be available here for reaction with the active hydrogen atoms but also for trimerization. Any compounds that initiate a polymerization reaction of the NCO group at room temperature are used as trimerization catalysts. Such compounds are described, for example, in French patent specification 1,441,565, Belgian patent specifications 723,153 and 723,152 or in German laid-open specification 2,301,408.
  • basic salts such as sodium acetate, potassium acetate or mononuclear or polynuclear Mannich bases composed of condensable phenols, oxo compounds and secondary amines optionally substituted by alkyl, aryl or aralkyl radicals, especially those in which formaldehyde is used as the oxo compound and secondary amine dimethylamine have been used.
  • blowing agents essential to the invention are also outstandingly suitable for the production of such polyisocyanate-based foams. Further details can be found, for example, in "Polyurethanes, Chemistry and Technology", Vol. I and II, Saunders-Frisc, Interscience Publishers, 1962 and 1964.
  • the amount of polymerization catalyst is essentially determined by the type and, if appropriate, the basicity of the catalyst; in general, if simultaneous isocyanurate formation is desired in the process according to the invention, 0.1 to 10, preferably 0.2 to 5% by weight of the trimerization catalysts, based on polyisocyanate component used.
  • the catalysts which accelerate the formation of polyurethane are generally used in an amount of between about 0.001 and 10 percent by weight, based on the amount of compounds having at least two isocyanate-reactive hydrogen atoms with a molecular weight of from 62 to 100,000.
  • surface-active additives esulsifiers and foam stabilizers
  • emulsifiers such.
  • Alkali metal or ammonium salts of sulfonic acids, such as dodecylbenzenesulfonic acid or dinaphthylmethane disulfonic acid, or else of fatty acids, such as ricinoleic acid or of polymeric fatty acids, can also be used as surface-active additives.
  • Water-soluble polyether siloxanes are particularly suitable as foam stabilizers. These compounds are generally designed so that a copolymer of ethylene oxide and propylene oxide is linked to a polydimethylsiloxane residue. Such foam stabilizers are such. B. described in US Patent 2764565.
  • reaction retarders for. B. acidic substances such as hydrochloric acid or organic acid halides, further cell regulators of the known type, such as paraffins or fatty alcohols or dimethylpolysiloxanes, and pigments or dyes and flame retardants of the known type, for. Also be used as tris-chloroethyl phosphate or ammonium phosphate and polyphosphate, also stabilizers against A ltêts- and weathering, softeners and fungistatic and bacteriostatic substances, fillers, such as barium sulphate, kieselguhr, carbon black or whiting.
  • acidic substances such as hydrochloric acid or organic acid halides
  • cell regulators of the known type such as paraffins or fatty alcohols or dimethylpolysiloxanes
  • pigments or dyes and flame retardants of the known type, for.
  • tris-chloroethyl phosphate or ammonium phosphate and polyphosphate also stabilizers against A
  • surface-active additives and foam stabilizers to be used according to the invention, as well as cell regulators, reaction retarders, stabilizers, flame-retardant substances, plasticizers, dyes and fillers, as well as fungistatically and bactericstatically active substances, and details on the use and action of these additives are given in the Plastics Manual, Volume VII by Vieweg and Höchtlen, Carl-Hanser-Verlag, Kunststoff 1966, z. B. described on pages 1 03 to 113.
  • the process according to the invention can be used both for the production of freely foamed foams and for the production of molded foams, in particular those with a closed outer skin.
  • the reaction mixture is introduced into a mold.
  • Metal for example aluminum or plastic, for example epoxy resin, can be used as the molding material.
  • the foamable reaction mixture foams in the mold and forms the shaped body.
  • the foaming of the mold can be carried out in such a way that the molded part has a cell structure on its surface, but it can also be carried out in such a way that the molded part has a compact skin and a cellular core.
  • Cold-curing foams can also be produced according to the invention (cf. British patent specification 1 162 517, German patent application specification 2 153 086).
  • reaction components are preferably reacted according to the known one-step process, machine equipment often being used, e.g. B. those described in U.S. Patent 2,764,565. Details about processing devices, which are also suitable according to the invention, are in the plastics manual, volume VII, edited by Vieweg and Höchtlen, Carl-Hanser-Verlag, Kunststoff 1966, z. B. described on pages 121 to 2 05 .
  • the process products can be used in a hard setting for the manufacture of furniture parts, body parts of vehicles, technical devices and components, as well as in a semi-hard to soft setting for the production of safety upholstery in automobile construction, elastic shoe soles, bumpers, etc.
  • the polyols were mixed in a paper cup with the additives and the blowing agents by stirring, the amount of blowing agent volatilized by the mixing process was added, the isocyanate was added and the mixture was stirred vigorously (all components had been heated to 20 ° C. before mixing).
  • blowing agent B the polyol additive component was first cooled to about 5 ° C. and the blowing agent was stirred in at this temperature. The mixture was then carefully warmed to 20 ° C. The reaction mixture was poured into a form of packaging paper (base area 20 ⁇ 20 cm square, height 14 cm) immediately after preparation. The start time and the setting time were measured during the foaming process.
  • the measurement data for the different formulations or different blowing agents are shown in the following table.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
EP78100668A 1977-08-27 1978-08-16 L'utilisation du 1,1,1,-trifluoro-2-chloréthane comme agent gonflant dans la préparation de mousses plastiques Withdrawn EP0000917A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2738719 1977-08-27
DE19772738719 DE2738719A1 (de) 1977-08-27 1977-08-27 Verfahren zur herstellung von geschaeumten kunststoffen

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EP0000917A1 true EP0000917A1 (fr) 1979-03-07

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US (1) US4177332A (fr)
EP (1) EP0000917A1 (fr)
JP (1) JPS5446267A (fr)
DE (1) DE2738719A1 (fr)
DK (1) DK377978A (fr)
ES (1) ES472837A1 (fr)
IT (1) IT7850857A0 (fr)

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US4624970A (en) * 1985-05-16 1986-11-25 Allied Corporation Foaming system for rigid urethane and isocyanurate foams based on polyethers and aromatic polyester polyols
DE3824354A1 (de) * 1988-07-19 1990-01-25 Basf Ag, 67063 Ludwigshafen Verfahren zur herstellung von zellhaltigen kunststoffen nach dem polyisocyanat-polyadditionsverfahren mittels lagerstabiler, treibmittelhaltiger emulsionen und diese emulsionen
US5001164A (en) * 1988-08-19 1991-03-19 The Dow Chemical Company Polyurethane foam prepared with reduced levels of hard halocarbon blowing agents
DE3903336A1 (de) * 1989-02-04 1990-08-09 Bayer Ag Verwendung von c(pfeil abwaerts)3(pfeil abwaerts)- bis c(pfeil abwaerts)5(pfeil abwaerts)-polyfluoralkanen als treibgase
US4945119A (en) * 1989-05-10 1990-07-31 The Dow Chemical Company Foaming system for rigid urethane and isocyanurate foams
DE59109031D1 (de) * 1990-06-07 1998-09-03 Ciba Geigy Ag Verfahren zur Herstellung von Polyurethanstoffen unter Verwendung von spezifischen Stabilisatorsystemen
US5130345A (en) * 1990-06-29 1992-07-14 Allied-Signal Inc. Method of preparing foam using a partially fluorinated alkane having a tertiary structure as a blowing agent
US5162123A (en) * 1991-05-10 1992-11-10 Dolco Packaging Corp. Spring-oriented rotary shear key for use in a mold
US7722951B2 (en) * 2004-10-15 2010-05-25 Georgia Tech Research Corporation Insulator coating and method for forming same

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FR2337743A1 (fr) * 1976-01-08 1977-08-05 Du Pont Procede perfectionne de preparation de mousses de polyurethanne

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US3062729A (en) * 1961-04-10 1962-11-06 Dow Chemical Co Foamed articles of ethylene-propylene copolymers and method of making
FR1457732A (fr) * 1964-09-30 1966-01-24 Allied Chem Mousses de chlorure de polyvinyle chloré et leur procédé d'obtention
US3640916A (en) * 1968-12-16 1972-02-08 Johnson & Son Inc S C Foam producing compositions
FR2205553A1 (en) * 1972-11-07 1974-05-31 Poudres & Explosifs Ste Nale Phenolic resin foam formation - using mixt. of blowing agents having different gas evolution temperatures
US3983080A (en) * 1974-09-20 1976-09-28 The Dow Chemical Company Extrusion foaming of normally crystalline vinylidene chloride polymers
FR2337743A1 (fr) * 1976-01-08 1977-08-05 Du Pont Procede perfectionne de preparation de mousses de polyurethanne
DE2704278A1 (de) * 1976-02-03 1977-08-04 Dow Chemical Co Styrol-polymerschaum und verfahren zu seiner herstellung

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JPS5446267A (en) 1979-04-12
IT7850857A0 (it) 1978-08-25
DE2738719A1 (de) 1979-03-08
US4177332A (en) 1979-12-04
DK377978A (da) 1979-02-28
ES472837A1 (es) 1979-03-16

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