GB888691A - Polyurethane products - Google Patents

Polyurethane products

Info

Publication number
GB888691A
GB888691A GB39032/58A GB3903258A GB888691A GB 888691 A GB888691 A GB 888691A GB 39032/58 A GB39032/58 A GB 39032/58A GB 3903258 A GB3903258 A GB 3903258A GB 888691 A GB888691 A GB 888691A
Authority
GB
United Kingdom
Prior art keywords
alkylene
nco
stage
ether
ratio
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
GB39032/58A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB888691A publication Critical patent/GB888691A/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
    • C08G18/28Polymeric 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
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0008Foam properties flexible
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0016Foam properties semi-rigid
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0025Foam properties rigid
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0083Foam properties prepared using water as the sole blowing agent

Landscapes

  • 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

A process for the production of foamable fluid polyurethane prepolymers containing unreacted NCO groups comprises reacting a polyalkylene ether, a polyalkylene ether prepared by the addition of an alkylene oxide to one or more organic polyfunctional compounds, or a mixture of one or more polyalkylene ethers with one or more organic polyfunctional compounds, with an organic polyisocyanate in an NCO:OH ratio less than 1 to produce a polyalkylene ether urethane and reacting the latter with a further quantity of an organic polyisocyanate in an NCO:OH ratio of greater than 1, said process being effected under anhydrous conditions. The products are foamable fluid prepolymers which have a stable viscosity (e.g. 5,000 to 10,000 cP at 25 DEG C.) even on prolonged heating. Preferably an NCO:OH ratio between 0,1 and 0,95, especially between 0,3 and 0,8, is employed in the first stage. As catalysts tripropylamine, triethylamine, ethyl morpholine, caprolactam, a -pyrrolidone or iron acetylacetonate are specified. Acids, acid chlorides or anhydrides may also be present. These catalysts or those disclosed in Specifications 769,680 and 769,682 are also useful in the second stage of prepolymer preparation. Additional polyisocyanate may be added to the prepolymer before the foaming step, as may accelerators and emulsifiers. The polyethers to be employed may be of the formula HO(RO)nX where R is an alkylene radical, X may be hydrogen or an alkylene amine, alkylene N-alkylamine, alkylene hydroxyamine or an alkylene N-aryl amine and n is an integer. Addition products of alkylene oxides with polyfunctional alcohols, amino alcohols or amines such as aniline, ethylene diamine, tetramethylene diamine are also suitable. In the first or second stage of the process there can also be mixed with the polyalkylene ether minor amounts of, e.g. 1,4-butylene glycol, trimethylol propane, pentaerythritol, hydroxyethylaniline, ethanolamine, N-ethylethanolamine or ethylene tetramethylene or hexamethylene diamine. Di- and tri-isocyanates are listed. In Example (1) a linear polypropylene ether is reacted in the presence of benzoyl chloride and iron acetylacetonate with toluylene 2:4- and 2:6-diisocyanates at an NCO:OH ratio of 0,6. The product is reacted with further diisocyanate to give a prepolymer containing 8,18% -NCO. This is converted to a foam by adding water, dimethyl-(3-ethoxypropyl) amine and a methylpolysiloxane. In generally similar processes (2) a mixture of the polypropylene ether and a glycerol/propylene oxide reaction product is used; (5) trimethylol propane is added at the second stage; (6) polyethylene ether glycol is used as starting material; (7) polyepichlorhydrin is used as starting material. Uses: crash pads, insulation, sponges, scrubbing pads, paint rollers, polishing pads, underlays.ALSO:A process for the production of foamable fluid polyurethane prepolymers containing unreacted NCO groups comprises reacting a polyalkylene ether, a modified polyalkylene ether prepared by the addition of an alkylene oxide to one or more organic polyfunctional compounds or a mixture of one or more polyalkylene ethers with one or more organic polyfunctional compounds, with an organic polyisocyanate in an NCO:OH ratio less than 1 to produce a polyalkylene ether urethane and reacting the latter with a further quantity of an organic polyisocyanate in an NCO:OH ratio of greater than 1, said process being effected under anhydrous conditions. The products are foamable fluid prepolymers which have a stable viscosity (e.g. 5000 to 10000 cp at 25 DEG C.) even on prolonged heating. Preferably an jNCO:OH ratio between 0,1 and 0,95, especially between 0,3 and 0,8, is employed in the first stage. As catalysts tripropylamine, triethylamine, ethymorpholine, coprolactam, a -pyrrolidone and iron acetylacetonate are specified. Acids, acid chlorides or anhydrides may also be present. These catalysts or those disclosed in Specification 769,680 and 769,682 are also useful in the second stage. Additional polyisocyanate, and accelerators and emulsifiers may be added to the prepolymer before the foaming step. The polyethers to be employed may be of the formula HO(RO)nX where R is an alkylene radical, X may be hydrogen or an alkylene amine, alkylene N-alkylamine, alkylene hydroxy-amine, or an alkylene N-aryl amine and n is an integer. Addition products of an alkylene oxide with polyfunctional alcohols, amino alcohols or amines such as aniline, ethylene diamine, tetramethylene diamine are also suitable. In the first or second stage of the process there can also be mixed with the polyalkylene ether minor amounts of e.g. 1,4-butylene glycol, trimethylolpropane, pentaerythritol, hydroxyethylaniline, ethanolamine, N-ethylethanolamine or ethylene, tetramethylene or hexamethylene diamines. Di-and triisocyanates are listed. In Example (1) a linear polypropylene glycol ether is reacted in the presence of benzoyl chloride and iron acetylacetonate in benzene with toluylene 2:4- and 2:6-diisocyanates in an NCO:OH ratio of 0,6. The product is reacted with further diisocyanate to give a prepolymer containing 8,18% NCO. This is converted to a foam by adding water, dimethy-(3-ethoxy propyl)-amine and a methylpolysiloxane. In generally similar processes (2) a mixture of the polypropylene ether glycol and a glycerine/propylene oxide addition product is used; (5) trimethylol propane is added at the second stage; (6) and (7) polyethylene ether glycol and polyepichlorhydrin, respectively, are used as starting material. Uses. Crush pads, insulation, sponges, scrubbing pads, paint rollers, polishing pads, underlays.
GB39032/58A 1957-12-03 1958-12-03 Polyurethane products Expired GB888691A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF24540A DE1096030B (en) 1957-12-03 1957-12-03 Process for the production of foams containing urethane groups

Publications (1)

Publication Number Publication Date
GB888691A true GB888691A (en) 1962-01-31

Family

ID=7091270

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39032/58A Expired GB888691A (en) 1957-12-03 1958-12-03 Polyurethane products

Country Status (4)

Country Link
BE (1) BE573498A (en)
DE (1) DE1096030B (en)
FR (1) FR1217737A (en)
GB (1) GB888691A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2139238A (en) * 1983-05-05 1984-11-07 Mobay Chemical Corp Flexible polyurethane foams

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1171152B (en) * 1962-03-20 1964-05-27 Schickedanz Ver Papierwerk Process for the production of foams containing urethane groups

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE961573C (en) * 1954-11-16 1957-04-11 Bayer Ag Process for the production of foams from linear or branched polyethers or polythioethers and polyisocyanates containing hydroxyl groups

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2139238A (en) * 1983-05-05 1984-11-07 Mobay Chemical Corp Flexible polyurethane foams

Also Published As

Publication number Publication date
BE573498A (en)
DE1096030B (en) 1960-12-29
FR1217737A (en) 1960-05-05

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