GB808635A - Improvements in or relating to elastomeric polymers and their production - Google Patents
Improvements in or relating to elastomeric polymers and their productionInfo
- Publication number
- GB808635A GB808635A GB22784/56A GB2278456A GB808635A GB 808635 A GB808635 A GB 808635A GB 22784/56 A GB22784/56 A GB 22784/56A GB 2278456 A GB2278456 A GB 2278456A GB 808635 A GB808635 A GB 808635A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- chloroformates
- diamine
- glycol
- ether
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
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
The invention comprises polymeric polyurethanes consisting essentially of substantially equimolecular amounts of (1) radicals obtainable by removing the terminal chlorine atoms from bis-chloroformates alternating with (2) radicals obtainable by removing one hydrogen atom from each of the nitrogens of a diamine, said diamine having at least one primary amine group, at least 60 per cent of the total weight of the polymer being the polymeric radicals obtainable by removing the terminal chlorine atoms from bis-chloroformates having molecular weights of at least 875 and consisting of polyalkylene-ether bis-chloroformates, polyalkyleneether - thioether bis - chloroformates, polyalkylenearylene-ether bis-chloroformates, polyurethane bis-chloroformates or polyaliphatic hydrocarbon bis-chloroformates (i.e. bis-chloroformates in which the chain carrying the chloroformate groups is obtained by polymerization of an unsaturated aliphatic hydrocarbon); the polymeric polyurethanes having attached to at least one of the radicals obtained from the diamine a side chain containing a primary hydroxyl group, the said chain occurring at least once for every 8000 molecular weight units of the polymeric polyurethanes. Such polymers are obtained by reaction of the appropriate chloroformate and the hydroxyl-containing diamine. There may be used in addition a further diamine or a bis-chloroformate of a low molecular weight non-polymeric glycol (i.e. M.Wt. below about 200). The preferred polyalkyleneether glycol is polytetramethylene-ether glycol. Others specified are polyethylene-ether, polypropylene - ether 1,2 - polydimethylethyleneether and polydecamethylene-ether glycols. Suitable polyurethane glycol bis-chloroformates are prepared by reacting a molar excess of a polymeric glycol, such as a polyalkylene-ether glycol, with an organic diisocyanate and treating the product with phosgene. Specified diisocyanates are toluene, m-phenylene, 4-chloro-1,3-phenylene, 4,41-biphenylene, 1,5-naphthylene, 1,4-tetramethylene, 1,6-hexamethylene, 1,10-decamethylene, 1,4-cyclohexylene, and 1,5-tetrahydronaphthylene diisocyanates and 4,41-methylene - bis - (cyclohexyl isocyanate). Suitable diamines are N-b -aminoethylethanolamine, 1,5-diamino-naphthalene, m-tolylene diamine, hexamethylene diamine, 1,4-cyclohexyl diamine, ethylene diamine and N-(b -hydroxyethyl) - p - phenylene diamine. Suitable low molecular weight glycols (the bis-chloroformates of which are optionally also employed), are ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,5-pentanediol, and p-phenylene dicarbinol. The hydroxyl groups in the polymeric polyurethane act as curing sites, the diisocyanates referred to above being suitable curing agents, being milled in before moulding under heat and pressure. In examples: (1) polytetramethylene-ether glycol of molecular weight 955 (in excess) is heated with toluene-2,4-diisocyanate and the polyurethane glycol obtained is reacted with phosgene. The resulting polyurethane bis-chloroformate is reacted with N-b -aminoethylethanolamine to give a polymer which is compounded with channel black and 3,31-dimethyl-4,41-biphenyl diisocyanate and cured under heat and pressure; (2) a polytetramethylene-ether bis-chloroformate (prepared by reacting phosgene with a polytetramethylene-ether glycol of molecular weight 3010) is reacted with a mixture of 1,5-diaminonaphthalene and aminoethylethanolamine. The resulting polymer is compounded with carbon black and 3,31-dimethyl-4,41-biphenyl diisocyanate and cured. The products can be used in tyres, inner tubes, belts, hose and tubing, wire and cable jackets, footwear, sponges and coated fabrics. Other compounding agents specified are clay, silica, esterified silica particles, talc, zinc and magnesium oxides, calcium and magnesium carbonates, titanium dioxide, plasticisers and inorganic and organic colouring agents.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US808635XA | 1955-08-04 | 1955-08-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB808635A true GB808635A (en) | 1959-02-11 |
Family
ID=22160125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22784/56A Expired GB808635A (en) | 1955-08-04 | 1956-07-23 | Improvements in or relating to elastomeric polymers and their production |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB808635A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111556881A (en) * | 2018-01-09 | 2020-08-18 | Ppg工业俄亥俄公司 | Hydroxy-functional alkyl carbamate cross-linking agents |
-
1956
- 1956-07-23 GB GB22784/56A patent/GB808635A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111556881A (en) * | 2018-01-09 | 2020-08-18 | Ppg工业俄亥俄公司 | Hydroxy-functional alkyl carbamate cross-linking agents |
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