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GB769091A - Production of condensation products, resinous foams and polymeric materials of high molecular weight - Google Patents

Production of condensation products, resinous foams and polymeric materials of high molecular weight

Info

Publication number
GB769091A
GB769091A GB20644/53A GB2064453A GB769091A GB 769091 A GB769091 A GB 769091A GB 20644/53 A GB20644/53 A GB 20644/53A GB 2064453 A GB2064453 A GB 2064453A GB 769091 A GB769091 A GB 769091A
Authority
GB
United Kingdom
Prior art keywords
glycol
polyurethanes
polyurethane
reacted
ncx
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.)
Expired
Application number
GB20644/53A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto 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 Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB769091A publication Critical patent/GB769091A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4825Polyethers containing two hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4833Polyethers containing oxyethylene units
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/307Other macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2101/00Manufacture of cellular products
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2170/00Compositions for adhesives
    • C08G2170/60Compositions for foaming; Foamed or intumescent adhesives
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2350/00Acoustic or vibration damping material

Landscapes

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

Abstract

A polyurethane is made by reacting in the liquid state and under anhydrous conditions an organic isocyanate or isothiocyanate of the formula R(NCX)n, where R is an organic group, X is oxygen or sulphur and n is at least 2, with a polyalkylene glycol having a molecular weight of at least 200 in amount such that the ratio of -(NCX) groups to the OH groups contained therein is greater than 1 : 1. The reactants are merely mixed together, or where solid at room temperature they are melted before mixing. The reaction may also be effected in a solvent, e.g. benzene, toluene, xylene, naphtha, gasoline, carbon tetrachloride, ethyl acetate or amyl acetate, and may be accelerated by the addition of up to 5 per cent of sodium or potassium hydroxide or a tertiary amine, e.g. N-methylmorpholine, triethylamine, tripropylamine, tributylamine, pyridine or quinoline. Many isocyanates and isothiocyanates are specified. The polyalkylene glycols, e.g. tetraethylene glycerol, polyethylene glycols having average molecular weights of 200, 400 and 600, polypropylene glycols having average molecular weights of 400, 750, 1200 and 2000 and carbowaxes having average molecular weights of 500 to 600 and 1000, may be used alone or in conjunction with polyols, e.g. pentaerythritol, sorbitol, sucrose, glycerine, glycerine-ethylene oxide condensate and triethanolamine-ethylene oxide condensate, or with monomeric diols, e.g. ethylene-, propylene- or butylene-glycol, 2-methyl pentane diol, 2-ethylhexane diol, styrene glycol, glycol-a -isopropyl ether or glycerol-a -phenyl ether. Polyurethanes or mixtures of polyurethanes and isocyanates or isothiocyanates result respectively where the ratio (NCX : OH) falls short of or exceeds n : 1. The polyurethanes so produced contain iso- or isothio-cyanate groups and may be reacted further either per se or with water or other compounds containing a plurality of active hydrogen atoms, e.g. hydrogen sulphide, carboxylic acids or esters or polyesters thereof, preferably in the presence of an emulsifying agent, to yield resinous foams or bubblefree resins, and find use in the production of adhesives, coating compositions, electrical-, heat- and sound-insulation materials, plastic articles, laminated products, radomes, abrasive articles and internal coatings for metallic receptacles. In examples (1, 3, 6 to 11 and 17)-m-tolylene diisocyanate is reacted with polyethylene glycol (200 or 400) in the presence or absence of dry benzene and in the presence or absence of various polyols to give liquids which may be further reacted in the presence of a tertiary amine to yield tough films; (12 to 16) the same reactants as used to make polyurethanes which are reacted further with water and ethylene glycol in the presence of emulsifying agents and tertiary amines to yield foamed products; (2, 4, 5) the isocyanate used is p.p1-diisocyanatodiphenylmethane; (18 to 21) particular applications are described in detail. Films of the polyurethanes are made by applying a volatile solvent, e.g. acetone, to a non-adhesive surface such as mercury and then casting a film of the polyurethane upon the surface of the mercury, with subsequent evaporation of the solvent and gradual reaction with atmospheric moisture or other active hydrogen-containing compound. The hardened film may then be removed from the non-adhesive surface.ALSO:In example (18) samples of aluminium and cold rolled steel were cleaned and coated with a benzene solution of a polymethane (see Group IV(a)) and then allowed to dry at room temperature and then at elevated temperatures. Corrosion resistant sheet metal objects such as autobodies, airplanes and air-conditioning conduits may be coated with resinous foams by depositing the polyurethane on the surface of the selected base and exposing the coating to atmospheric moisture to cause foam formation of the polyurethane.
GB20644/53A 1952-07-25 1953-07-24 Production of condensation products, resinous foams and polymeric materials of high molecular weight Expired GB769091A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US769091XA 1952-07-25 1952-07-25

Publications (1)

Publication Number Publication Date
GB769091A true GB769091A (en) 1957-02-27

Family

ID=22134916

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20644/53A Expired GB769091A (en) 1952-07-25 1953-07-24 Production of condensation products, resinous foams and polymeric materials of high molecular weight

Country Status (2)

Country Link
DE (1) DE1302619B (en)
GB (1) GB769091A (en)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1098708B (en) * 1957-07-17 1961-02-02 Bayer Ag Process for the production of foams containing urethane groups
DE1099726B (en) * 1957-11-09 1961-02-16 Bayer Ag Process for the production of foams containing urethane groups
DE1105158B (en) * 1958-04-03 1961-04-20 Bataafsche Petroleum Process for the production of homogeneous or foamed polymerization products containing urethane groups
US2990376A (en) * 1959-01-29 1961-06-27 Dow Chemical Co Cross-linking agent and method for making same
DE1113083B (en) * 1958-08-15 1961-08-24 Ici Ltd Process for the production of optionally foamed polyurethanes
US3012993A (en) * 1958-04-21 1961-12-12 Du Pont Branched chain polyurethane polymers
DE1119506B (en) * 1958-11-20 1961-12-14 Union Carbide Corp Process for the production of foams based on polyether urethanes
DE1127082B (en) * 1959-02-26 1962-04-05 Hoechst Ag Process for the production of high molecular weight water-soluble or water-swellable polyaether urethanes
US3049513A (en) * 1959-03-26 1962-08-14 Wyandotte Chemicals Corp Ordered isocyanate-terminated polyether-based urethane compositions
US3049516A (en) * 1959-03-26 1962-08-14 Wyandotte Chemicals Corp Ordered hydroxy-terminated polyether-based urethane compositions
DE1144002B (en) * 1958-12-22 1963-02-21 Dow Chemical Co Process for the production of cellular molding compositions containing urethane groups
US3098658A (en) * 1958-11-12 1963-07-23 Goodrich Co B F Golf ball having a polyetherurethane core
DE1151929B (en) * 1960-06-02 1963-07-25 Dow Chemical Co Process for the production of polyurethane foams
DE1179660B (en) * 1961-04-19 1964-10-15 Henkel & Cie Gmbh Coating compositions which form highly elastic films, in particular rubber lacquers based on sulfur-containing polyurethanes
DE1194136B (en) * 1960-02-15 1965-06-03 Monsanto Co Process for the production of polyurethane foams
DE1225381B (en) * 1964-12-12 1966-09-22 Bayer Ag Process for the production of molded bodies, including flat structures, based on urethane prepolymers
DE1241974B (en) * 1963-10-23 1967-06-08 Kurashiki Rayon Company Ltd Stabilizers for Polyurethanes
DE1247629B (en) * 1964-01-02 1967-08-17 Elekal Fa Process for the production of polyurethane foams
FR2215445A1 (en) * 1973-01-29 1974-08-23 Ici Ltd
US4558073A (en) * 1981-06-09 1985-12-10 Henkel Kommanditgesellschaft Auf Aktien Composition for the production of polyurethane foam materials having improved form stability
CN115434073A (en) * 2022-09-13 2022-12-06 上海迅江科技有限公司 Polyurethane nanofiber waterproof moisture-permeable film and preparation method and application thereof

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1098708B (en) * 1957-07-17 1961-02-02 Bayer Ag Process for the production of foams containing urethane groups
DE1099726B (en) * 1957-11-09 1961-02-16 Bayer Ag Process for the production of foams containing urethane groups
DE1105158B (en) * 1958-04-03 1961-04-20 Bataafsche Petroleum Process for the production of homogeneous or foamed polymerization products containing urethane groups
US3012993A (en) * 1958-04-21 1961-12-12 Du Pont Branched chain polyurethane polymers
DE1113083B (en) * 1958-08-15 1961-08-24 Ici Ltd Process for the production of optionally foamed polyurethanes
DE1125647B (en) * 1958-08-15 1962-03-15 Ici Ltd Process for the production of optionally foamed polyurethanes
US3098658A (en) * 1958-11-12 1963-07-23 Goodrich Co B F Golf ball having a polyetherurethane core
DE1119506B (en) * 1958-11-20 1961-12-14 Union Carbide Corp Process for the production of foams based on polyether urethanes
DE1144002B (en) * 1958-12-22 1963-02-21 Dow Chemical Co Process for the production of cellular molding compositions containing urethane groups
US2990376A (en) * 1959-01-29 1961-06-27 Dow Chemical Co Cross-linking agent and method for making same
DE1127082B (en) * 1959-02-26 1962-04-05 Hoechst Ag Process for the production of high molecular weight water-soluble or water-swellable polyaether urethanes
US3049516A (en) * 1959-03-26 1962-08-14 Wyandotte Chemicals Corp Ordered hydroxy-terminated polyether-based urethane compositions
US3049513A (en) * 1959-03-26 1962-08-14 Wyandotte Chemicals Corp Ordered isocyanate-terminated polyether-based urethane compositions
DE1194136B (en) * 1960-02-15 1965-06-03 Monsanto Co Process for the production of polyurethane foams
DE1151929B (en) * 1960-06-02 1963-07-25 Dow Chemical Co Process for the production of polyurethane foams
DE1179660B (en) * 1961-04-19 1964-10-15 Henkel & Cie Gmbh Coating compositions which form highly elastic films, in particular rubber lacquers based on sulfur-containing polyurethanes
DE1241974B (en) * 1963-10-23 1967-06-08 Kurashiki Rayon Company Ltd Stabilizers for Polyurethanes
DE1247629B (en) * 1964-01-02 1967-08-17 Elekal Fa Process for the production of polyurethane foams
DE1225381B (en) * 1964-12-12 1966-09-22 Bayer Ag Process for the production of molded bodies, including flat structures, based on urethane prepolymers
FR2215445A1 (en) * 1973-01-29 1974-08-23 Ici Ltd
US4558073A (en) * 1981-06-09 1985-12-10 Henkel Kommanditgesellschaft Auf Aktien Composition for the production of polyurethane foam materials having improved form stability
CN115434073A (en) * 2022-09-13 2022-12-06 上海迅江科技有限公司 Polyurethane nanofiber waterproof moisture-permeable film and preparation method and application thereof

Also Published As

Publication number Publication date
DE1302619B (en) 1970-12-17

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