GB842154A - Polyisocyanate compositions - Google Patents

Polyisocyanate compositions

Info

Publication number
GB842154A
GB842154A GB1032657A GB1032657A GB842154A GB 842154 A GB842154 A GB 842154A GB 1032657 A GB1032657 A GB 1032657A GB 1032657 A GB1032657 A GB 1032657A GB 842154 A GB842154 A GB 842154A
Authority
GB
United Kingdom
Prior art keywords
isocyanate
amines
aniline
groups
give
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
GB1032657A
Inventor
Harold France
Arnold Lister
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1032657A priority Critical patent/GB842154A/en
Priority to US724513A priority patent/US3012008A/en
Priority to FR1201544D priority patent/FR1201544A/en
Publication of GB842154A publication Critical patent/GB842154A/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
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The invention comprises the reaction products of a liquid poly isocyanate composition, obtained by phosgenating the polyamine composition obtained by condensing formaldehyde with a mixture of at least two aromatic amines, and less than the stoichiometric equivalent of at least one compound containing a plurality of isocyanate-reactive groups. The amines mentioned include aniline, toluidines, chloroanilines, anisidines, nitroanilines, m-phenylene diamine, m-toluylene diamine and chloro-m-phenylene diamine, preferably 4 to 5 moles of mixed amines per mole of formaldehyde are used to give predominantly a dinuclear product which is phosgenated in the usual manner. Isocyanate-reactive compounds mentioned include trimethylolpropane, hexane-triol, castor oil, ethanolamines, alkylene glycols, polyesters and polyesteramides containing hydroxyl and carboxyl groups as reactive groups and polyethers containing reactive hydroxyl groups; preferably 0,2 to 0,3 isocyanate-reactive groups are used per isocyanate group. This reaction may be carried out in a solvent, for example, a ketone or ester. The liquid polyisocyanates may first be modified by treatment with phenol or an acetoacetic ester to give products containing one or more "masked" isocyanate groups or polymerised e.g. to dimers containing uretedione linkages by treatment with pyridine or to isocyanurate polymers by treatment with a basic organic or inorganic metal compound. In the examples polyisocyanates derived from a) aniline and toluidine and (b) aniline and chloroaniline, are reacted with (a) trimethylolpropane, (b) hexane-triol, (c) triethanolamine, (d) diethylene glycol, (e) castor oil, (f) a polyester derived from adipic acid and glycerol and (g) a polyester derived from adipic acid, glycerol and ethylene glycol. Specification 809,809 is referred to.ALSO:The invention comprises liquid polyisocyanate compositions obtained by phosgenating the polyamine compositions obtained by condensing formaldehyde with a mixture of at least two aromatic amines. The condensation and phosgenation are carried out in the usual manner using 4 to 5 moles of amines per mole of formaldhyde so as to minimise the undesirable production of amines having more than two nuclei and preferably the proportions of amines are chosen so that no more than 80% by molecular proportions of any single amine is converted to the polyamine composition. Amines specified are aniline, toluidine, chloroanilines, anisidines, nitro-anilines, m-phenylene diamine, m-toluylene diamine and chloro-m-phenylene diamine. The polyisocyanates may be polymerised by treatment with, for example, pyridine to give dimers containing uretedione linkages or basic organic or inorganic metal compounds to give isocyanurate polymers. The polyisocyanates may be reacted with up to the theoretical quantity of phenol or an acetoacetic ester to give derivatives containing 1 or more "masked" isocyanate groups. The polyisocyanates may also be reacted with less than the stoichiometric equivalent e.g. 20 - 30% of the equivalent of at least one compound containing a plurality of isocyanate-reactive groups. This reaction may be carried out in a solvent such as ketone or ester using compounds such as trimethylol propane, castor oil, hexane triols, ethanolamines, alkylene glycols, polyesters and polyesteramides containing free hydroxyl or carboxyl groups or polyethers containing free hydroxyl groups. In examples the following amines are condensed with formaldehyde and the condensate phosgenated: (a) aniline and o-toluidine which give the new compound 4,41-di-isocyanate-3-methyl diphenylmethane, (b) aniline and o-chloroaniline, (c) aniline, o-toluidine and m-tolylene diamine. The di-isocyanate obtained in (a) is polymerised by treatment with sodium methoxide and lead 2-ethyl-hexoate. Specification 899,809 is referred to.ALSO:Cellular, rigid or flexible polyurethane products are prepared from high molecular weight polyhydroxy compounds and a polyisocyanate where the polyisocyanate used is a liquid polyisocyanate composition obtained by phosgenating the polyamine composition obtained by condensing formaldehyde with a mixture of at least two aromatic amines. Specification 809,809 is referred to.
GB1032657A 1957-03-29 1957-03-29 Polyisocyanate compositions Expired GB842154A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB1032657A GB842154A (en) 1957-03-29 1957-03-29 Polyisocyanate compositions
US724513A US3012008A (en) 1957-03-29 1958-03-28 Polyisocyanate compositions
FR1201544D FR1201544A (en) 1957-03-29 1958-03-29 Polyisocyanate compositions for use in the manufacture of polyurethanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1032657A GB842154A (en) 1957-03-29 1957-03-29 Polyisocyanate compositions

Publications (1)

Publication Number Publication Date
GB842154A true GB842154A (en) 1960-07-20

Family

ID=9965798

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1032657A Expired GB842154A (en) 1957-03-29 1957-03-29 Polyisocyanate compositions

Country Status (1)

Country Link
GB (1) GB842154A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3459781A (en) * 1965-11-22 1969-08-05 Du Pont Liquid polyisocyanates and their stepwise preparation
WO2013057069A1 (en) 2011-10-21 2013-04-25 Bayer Intellectual Property Gmbh Polycyclic aromatic polyamines and methods for production thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3459781A (en) * 1965-11-22 1969-08-05 Du Pont Liquid polyisocyanates and their stepwise preparation
WO2013057069A1 (en) 2011-10-21 2013-04-25 Bayer Intellectual Property Gmbh Polycyclic aromatic polyamines and methods for production thereof

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