GB1122545A - Polyurethane plastics - Google Patents

Polyurethane plastics

Info

Publication number
GB1122545A
GB1122545A GB33146/66A GB3314666A GB1122545A GB 1122545 A GB1122545 A GB 1122545A GB 33146/66 A GB33146/66 A GB 33146/66A GB 3314666 A GB3314666 A GB 3314666A GB 1122545 A GB1122545 A GB 1122545A
Authority
GB
United Kingdom
Prior art keywords
polyhydroxyl
prepared
compounds
reacting
groups
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
GB33146/66A
Inventor
Gunter Oertel
Hans-Georg Schmelzer
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 GB1122545A publication Critical patent/GB1122545A/en
Expired 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
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
    • C08G18/388—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to 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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4684—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing phosphorus
    • 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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
    • C08G18/5078—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to 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
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6461—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having phosphorus
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/68—Unsaturated polyesters
    • 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
    • C08G18/83—Chemically modified polymers
    • C08G18/833—Chemically modified polymers by nitrogen containing compounds

Landscapes

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

Abstract

Polyurethanes prepared by reacting polyhydroxyl compounds with polyisocyanates and which contain incorporated in the molecule two or more groups of the formula <FORM:1122545/C3/1> in which the phosphorus atom is linked to a carbon atom directly or through an oxygen or nitrogen atom are cross-linked by reacting them at - 20 DEG to 250 DEG C. with a compound which may be resinous and which contains at least two azomethine groups in the molecule. The polyurethanes are suitably prepared by reacting an organic polyisocyanate with a polyhydroxyl containing compound having a M.W. greater than 1000 and/or a polyhydroxyl compound having a M.W. less than 1000 either or both of the polyhydroxyl containing compounds containing at least one of the above specified phosphorus containing groups. Suitable polyhydroxyl containing compounds having a M.W. greater than 1000 and containing the above specified phosphorus containing groups are condensation products of lower dialkylphosphites or diphenylphosphite with polyesteramides, polyacetals, polyesters, polyethers, polythioethers or low M.W. polyhydroxyl containing compounds. The corresponding compounds having a M.W. less than 1000 may be prepared by reacting lower dialkylphosphites and low M.W. polyhydroxyl containing compounds, by reacting phosphorous acid and alkylene oxides and by reacting esters, amides or chlorides of trivalent phosphorus with aminoalcohols or polyamines. Conventional polymeric and monomeric polyhydroxyl-containing compounds may also be included in the reaction system. The one-shot or prepolymer techniques may be employed to form the polyurethanes, using conventional polyisocyanates. Suitable compounds containing at least two azomethine groups are reaction products of monoaldehydes or ketones with polyamines or of polyaldehydes with primary alkyl- and hydroxyalkyl amines. The azomethine group containing compounds may be prepared in the cross-linking reaction mixture, and the reaction may be carried out in the presence of a solvent. Polyesters may be prepared by reacting di-(b -chloroethyl)-phosphite with (a) 1,6-hexane diol, (b) diphenylolpropane - di - (b - hydroxyethyl-ether) or (c) N,N-di-(b -hydroxyethyl)-aminomethyl-phosphonic acid diethyl ester.ALSO:Glass and copper plates may be coated with a composition comprising (i) a polyurethane which has been prepared from polyhydroxyl compounds and polyisocyanates and which contains in the molecule two or more groups of the formula: <FORM:1122545/B1-B2/1> in which the phosphorus atom is linked to a carbon atom either directly or through an oxygen or nitrogen atom (ii) a compound which may be resinous and which contains at least two azomethine groups in the molecule and (iii) optionally an inert organic solvent. The solvent may be removed and the composition cured by heating. Numerous Examples are given wherein the polyurethane is prepared from conventional polyisocyanates and high and/or low molecular weight polyols, either or both of said polyols containing the necessary phosphorous atom containing groupings and the azomethine group containing compounds are those prepared from aldehydes or ketones and polyamines or from polyaldehydes and mono- or polyamines. Such azomethine group containing compounds may be prepared in situ in the coating compositions.
GB33146/66A 1965-07-22 1966-07-22 Polyurethane plastics Expired GB1122545A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0046677 1965-07-22

Publications (1)

Publication Number Publication Date
GB1122545A true GB1122545A (en) 1968-08-07

Family

ID=7101179

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33146/66A Expired GB1122545A (en) 1965-07-22 1966-07-22 Polyurethane plastics

Country Status (3)

Country Link
DE (1) DE1570590C3 (en)
FR (1) FR1487619A (en)
GB (1) GB1122545A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1394189A1 (en) * 2002-08-21 2004-03-03 Bayer MaterialScience AG Thermoplastic polyurethanes having selfextinguishing properties, a process for their preparation and use.
CN114805748A (en) * 2022-05-27 2022-07-29 杨骏 Sustainable and high-modulus Schiff base functional polyurethane prepolymer and preparation method thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1394189A1 (en) * 2002-08-21 2004-03-03 Bayer MaterialScience AG Thermoplastic polyurethanes having selfextinguishing properties, a process for their preparation and use.
US7160974B2 (en) 2002-08-21 2007-01-09 Bayer Materialscience Ag Thermoplastically processable polyurethanes (TPU) with self-extinguishing properties, a process for their preparation and their use
CN1294175C (en) * 2002-08-21 2007-01-10 拜尔公司 Thermophastic workable polyurethane with self-extinguishability, its preparation method and application
CN114805748A (en) * 2022-05-27 2022-07-29 杨骏 Sustainable and high-modulus Schiff base functional polyurethane prepolymer and preparation method thereof
CN114805748B (en) * 2022-05-27 2024-02-27 宁波微循科技有限公司 Sustainable and high-modulus Schiff base functional polyurethane prepolymer and preparation method thereof

Also Published As

Publication number Publication date
DE1570590A1 (en) 1969-08-28
FR1487619A (en) 1967-07-07
DE1570590B2 (en) 1974-10-17
DE1570590C3 (en) 1975-06-05

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