GB842154A - Polyisocyanate compositions - Google Patents
Polyisocyanate compositionsInfo
- 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
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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates 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.
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)
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 |
-
1957
- 1957-03-29 GB GB1032657A patent/GB842154A/en not_active Expired
Cited By (2)
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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