GB961624A - Improvements in or relating to isocyanurate compounds - Google Patents
Improvements in or relating to isocyanurate compoundsInfo
- Publication number
- GB961624A GB961624A GB17256/62A GB1725662A GB961624A GB 961624 A GB961624 A GB 961624A GB 17256/62 A GB17256/62 A GB 17256/62A GB 1725662 A GB1725662 A GB 1725662A GB 961624 A GB961624 A GB 961624A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyethyl
- isocyanurate
- tri
- acid
- reaction
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
N-(b -hydroxyethyl), N, N1-di(b -hydroxyethyl) and N, N1, N11-tri (b -hydroxyethyl) derivatives of isocyanuric acid are prepared by treating a salt of cyanuric acid, e.g. an alkali-metal cyanurate, with an ethylene halohydrin in water or in an organic solvent. The preferred solvents are liquid aliphatic acid dialkylamides, e.g. dimethyl- or diethyl-formamide or dimethylacetamide, or dialkyl sulphoxides, e.g. dimethyl sulphoxide. Other solvents are also specified. Alternatively, the reaction may be effected by passing a solution of a cyanurate through a column of an anion-exchange resin, e.g. a polystyrene quaternary-amine type resin, and then passing a solution of an ethylene halohydrin through the column. When only one or two b -hydroxyethyl groups are introduced into the isocyanurate ring, the remaining nitrogen atom or atoms may be alkylated or aralkylated, e.g. by treatment with methyl iodide, allyl or methallyl chloride, chloromethyl-alkyl ethers in which the alkyl group has 1-20 carbon atoms, alkyl chloracetates or benzyl chloride. This reaction is preferably effected simultaneously with the hydroxyethylation. Examples are given of the preparation of mono-, di- and tri-(b -hydroxyethyl) isocyanurate, monoallyl-di-(b -hydroxyethyl) isocyanurate and diallyl-mono-(b -hydroxyethyl) isocyanurate. The products containing two or three b -hydroxyethyl groups, e.g. di- or tri-(b -hydroxyethyl) isocyanurate or monoallyl-di-(b -hydroxyethyl) isocyanurate, yield polyester condensation products by reaction with dicarboxylic acids, e.g. succinic, adipic, phthalic, terephthalic, sebacic, 1,4-naphthalene dicarboxylic, azelaic, glutaric or 3-ethylsebacic acid (see Division C3).ALSO:N-(b -hydroxyethyl), N,N1-di(b -hydroxyethyl) and N,N1,N11-tri(b -hydroxyethyl) derivatives of isocyanuric acid are prepared by treating a salt of cyanuric acid, e.g. an alkali-metal cyanurate, with an ethylene halohydrin in water or in an organic solvent (see Division C2). When only one or two b -hydroxyethyl groups are introduced into the isocyanurate ring, the remaining nitrogen atom or atoms may be alkylated or aralkylated, e.g. by treatment with methyl iodide, allyl or methallyl chloride, chloromethyl-alkyl ethers in which the alkyl group has 1-20 carbon atoms, alkyl chloracetates or benzyl chloride. This reaction is preferably effected simultaneously with the hydroxyethylation. Examples are given of the preparation of mono-, di- and tri-(b -hydroxyethyl) isocyanurate, monoallyl-di-(b -hydroxyethyl) isocyanurate and diallyl-mono-(b -hydroxyethyl) isocyanurate. The products containing two or three b -hydroxyethyl groups, e.g. di- or tri-(b -hydroxyethyl) isocyanurate, or monoallyl-di-(b -hdroxyethyl) isocyanurate, yield polyester condensation products by reaction with dicarboxylic acids, e.g. succinic adipic, phthalic, terephthalic, sebacic, 1,4-naphthalene dicarboxylic, azelaic, glutaric or 3-ethylsebacic acid. Polyester resins are also obtainable from mixtures of di- or tri-(b -hydroxyethyl) isocyanurate and other diols, e.g. ethylene glycol, propylene glycol, hexamethylene glycol, neopentyl glycol, diethylene glycol, decamethylene glycol or 2,2-dimethyl-1, 3-propane diol. Such of the products as contain allyl groups may be condensed to form thermoset polymers, optionally with the addition of another monomer, e.g. styrene or triallyl isocyanurate. Diallylmono-(b -hydroxyethyl) isocyanurate is useful as a chain-length regulator when used in varying amounts in a polyester-forming reaction. Examples are given of the preparation of resins from (a) tri-(b -hydroxyethyl) isocyanurate and phthalic anhydride and (b) monoallyl-di-(b -hydroxyethyl) isocyanurate and adipic acid; the latter resin can be cured after admixture with styrene and a minor proportion of tert.-butyl perbenzoate.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10901761A | 1961-05-10 | 1961-05-10 | |
US109018A US3200119A (en) | 1961-05-10 | 1961-05-10 | Isocyanurate compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB961624A true GB961624A (en) | 1964-06-24 |
Family
ID=26806542
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB17256/62A Expired GB961624A (en) | 1961-05-10 | 1962-05-04 | Improvements in or relating to isocyanurate compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB961624A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1645435A1 (en) * | 1965-05-20 | 1970-06-18 | Schenectady Chemical | Process for the production of a heat-resistant polyester-polyimide plastic |
JP2013049657A (en) * | 2011-08-03 | 2013-03-14 | Shikoku Chem Corp | Isocyanurate compound |
CN110845712A (en) * | 2019-11-23 | 2020-02-28 | 李丹丹 | Novel polyester and preparation method thereof |
-
1962
- 1962-05-04 GB GB17256/62A patent/GB961624A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1645435A1 (en) * | 1965-05-20 | 1970-06-18 | Schenectady Chemical | Process for the production of a heat-resistant polyester-polyimide plastic |
JP2013049657A (en) * | 2011-08-03 | 2013-03-14 | Shikoku Chem Corp | Isocyanurate compound |
CN110845712A (en) * | 2019-11-23 | 2020-02-28 | 李丹丹 | Novel polyester and preparation method thereof |
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