GB858810A - Process for manufacturing cyanuric and isocyanuric acid derivatives - Google Patents

Process for manufacturing cyanuric and isocyanuric acid derivatives

Info

Publication number
GB858810A
GB858810A GB14791/58A GB1479158A GB858810A GB 858810 A GB858810 A GB 858810A GB 14791/58 A GB14791/58 A GB 14791/58A GB 1479158 A GB1479158 A GB 1479158A GB 858810 A GB858810 A GB 858810A
Authority
GB
United Kingdom
Prior art keywords
tris
alkyl
sulphone
cyanurate
sulphoxide
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
GB14791/58A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB858810A publication Critical patent/GB858810A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12Heterocyclic 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
    • C07D251/26Heterocyclic 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
    • C07D251/30Only oxygen atoms
    • C07D251/34Cyanuric or isocyanuric esters

Abstract

Polymeric cyanuric and/or isocyanuric acid esters are prepared by reacting at least one organic halogen-containing compound having at least two halogenomethylene or halogenomethylgroups, as hereinafter defined, in the molecule and no acidic or basic group, with an alkali cyanate, as hereinafter defined, in the presence of solvent quantities of a dialkyl sulphoxide, alkylene sulphoxide, dialkyl sulphone, alkylene sulphone or compound of the formula R1 NYZ wherein R1 is alkyl, Y is alkyl, R1CO, aryl or together with R1 forms a heterocyclic ring which may contain a further hereto atom, Z is R1CO or R11 SO2 where R1 is hydrogen, an aliphatic or an aromatic radical and R11 is an aliphatic or aromatic radical. The products may contain rings having a mixed cyanurate/isocyanurate structure. The halogenomethyl or halogenomethylene groups must contain chlorine, bromine or iodine; if fluorine is also present it does not take part in the reaction. The alkali cyanates are defined as lithium, sodium, potassium and ammonium cyanates or their mixtures. The organic halogencontaining compound(s) may be saturated or unsaturated. Inorganic iodides act as promoters. Temperatures of 30 to 300 DEG C. are mentioned. The products may be stabilized by treatment with substances having active hydrogen to react with end groups. e.g. water, alcohols, glycols, phenols, aldehydes, organic or inorganic acids, metal hydroxides, organo silanols, ammonia, amines, inorganic bases, mercaptans or polymers; specified are diethylamine, water, aqueous NaOH, and a two stage use of water and acetic anhydride. Polymers are prepared in examples from 1, 4-dichlorobutane, 1, 2-dibromoethane, trimethylene chlorobromide, propylene dichloride, bis-(b -chlorethyl) ether, bis-(4-chlorobutyl) ether, bis-(b -chlorethyl) sulphone, chlorinated kerosene, chlorinated pentane, polychlorinated xylene (mainly m-and p-chloromethylbenzyl chlorides), tris-(4-chlorobutyl)-iso-cyanurate, tris-(5-chloropentyl)-isocyanurate, tris-(b chloroethyl)- cyanurate and a mixture of tris(4-chlorobutyl)-isocyanurate and tris-(5-chloropentyl)-isocyanurate: solvents used are dimethyl formamide and sulphoxide. In examples (20) a porous resin is obtained, mainly poly (butylenediisocyanurate) in the pores of which styrene is polymerized in the presence of 2% peroxide, and cured at 60 DEG C. for several days. In example (29) polystyrene, polyvinyl acetate or polyacrylonitrile powder is added to a poly-kerosene cyanurate for moulding. In Example (32) tricresyl phosphate is added to a polycyanurate. An optional additive mentioned is glass fibres. Uses. Lubricants: plasticizers: pastes: paints: fillers: packing; sponges: films: synthetic rubber: laminates; porous insulation.ALSO:Cyanuric and isocyanuric acid esters are prepared by reacting at least one organic halogen-containing compound having at least one halogenomethylene or halogenomethyl group, as hereinafter defined, in the molecule and no acidic or basic group, with an alkali cyanate, as hereinafter defined, in the presence of solvent quantities of a dialkyl sulphoxide, alkylene sulphoxide, dialkyl sulphone, alkylene sulphone or compound of the formula R1 NYZ wherein R1 is alkyl, Y is alkyl, R1CO, aryl or together with R1 forms a heterocyclic ring which may contain a further hetero atom, Z is R1CO or R11SO2 where R1 is hydrogen, an aliphatic or an aromatic radical and R11 is an aliphatic or aromatic radical, The products may contain rings having a mixed cyanurate/isocyanurate structure. The halogenomethyl or halogenomethylene group must contain chlorine, bromine or iodine ; if fluorine is also present it does not take part in the reaction. The alkali cyanates are defined as lithium, sodium, potassium and ammonium cyanates or their mixtures. The organic halogen-containing compound(s) may be saturated or unsaturated. Inorganic iodides act as promoters. Temperatures of 30 to 300 DEG C. are mentioned. Esters containing 3 alkyl groups of 3 or more carbon atoms each are useful as plasticisers. Esters prepared in examples include trimethyl-, triethyl-, tri-isobutyl-, triallyl-, tribenzyl-, tris-(4-chlorobutyl)-, tris-(5-chloropentyl)- and tris-(4-fluorobutyl) isocyanurates, mixed allyl/butyl cyanurates and cyanuric esters from the alkyl chlorides derived from palm oil alcohol.ALSO:A spongy resin, mainly poly (butylene-diisocyanurate), is obtained by reacting potassium cyanate and 1, 4-dichlorobutane in dimethylformamide solution, filtering, distilling the filtrate, and blending the residue, after solvent removal, in air, and leaving it in a mould at room temperature for several days, during which it expands to a spongy cake-suitable for building materials.
GB14791/58A 1957-09-09 1958-05-08 Process for manufacturing cyanuric and isocyanuric acid derivatives Expired GB858810A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP858810X 1957-09-09

Publications (1)

Publication Number Publication Date
GB858810A true GB858810A (en) 1961-01-18

Family

ID=13871230

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14791/58A Expired GB858810A (en) 1957-09-09 1958-05-08 Process for manufacturing cyanuric and isocyanuric acid derivatives

Country Status (1)

Country Link
GB (1) GB858810A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259626A (en) * 1962-07-05 1966-07-05 Bayer Ag Isocyanurate process
EP0078567A1 (en) * 1981-11-04 1983-05-11 Akzo N.V. Preparation of isocyanuric esters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259626A (en) * 1962-07-05 1966-07-05 Bayer Ag Isocyanurate process
EP0078567A1 (en) * 1981-11-04 1983-05-11 Akzo N.V. Preparation of isocyanuric esters
US4451651A (en) * 1981-11-04 1984-05-29 Akzo Nv Preparation of isocyanuric esters

Similar Documents

Publication Publication Date Title
US3492301A (en) 2,4,6-trisubstituted sulfonylhydrazido-s-triazines
GB819689A (en) Thiophosphoric acid esters
GB858810A (en) Process for manufacturing cyanuric and isocyanuric acid derivatives
GB1357852A (en) Process for the preparation of 1,2,4-triazin-5-ones
US4127718A (en) Tris-tetrazoles as chemical blowing agents
US2542417A (en) Hexamethyl benzene compounds
US2375628A (en) Method of preparing derivatives of morpholine and thiamorpholine
US3107229A (en) Process for stabilizing polyolefins
US3225041A (en) Process for producing 2,6-diamino pyridines
US3130197A (en) Production of azamonomethinecyanines of the benzothiazole series
JPS5855979B2 (en) Vulcanizable rubber mixture with increased processing safety
US3732291A (en) Preparation of fluoroammonium salts and their applications
GB1009965A (en) Process for the production of polyurethane foam
GB956221A (en) Tertiary phosphines and methods of preparing same
US3106555A (en) Novel amino chlorosulfenyl-s-triazines, their hydrochlorides and process for their production
GB1032370A (en) Polyisonitriles and a process for their production
US2915525A (en) Preparation of arylenebenzoxazolols and arylenebenzothiazolols
GB912112A (en) Haloalkyl triazines
US3592811A (en) 2-hexafluoroisopropylidene-1,3-thiazetidines and the preparation thereof
US3317529A (en) N-halomethyl s-triazines
US2626950A (en) 2-haloimino-4-thiazolines
GB808259A (en) Thiophosphoric acid esters
IL43143A (en) Process for the preparation of alpha-oximinonitriles
US2543341A (en) Aroylacetamidine
US3455947A (en) Production of 4-formylmethylene-oxazolidinones-(2)