Dialkenyl arylphosphonates and polymers thereof
Номер патента: GB645222A
Опубликовано: 25-10-1950
Автор(ы):
Принадлежит: Bataafsche Petroleum Maatschappij NV
Опубликовано: 25-10-1950
Автор(ы):
Принадлежит: Bataafsche Petroleum Maatschappij NV
Реферат: Diesters of aryl phosphonic acids with b :g -mono-olefinic monohydric alcohols, e.g. diallyl phenyl phosphonate, are polymerized to fire-resistant resins by means of heat and (or) light, optionally in the presence of a polymerization catalyst, e.g. an organic peroxide such as benzoyl peroxide, a hydroperoxide, e.g. tert.-butyl peroxide, peracetic acid, an inorganic per-salt, ozone or oxygen. The aryl radical in the aryl phosphonic acid is usually phenyl which may be substituted by benzyl or lower alkyl groups, and the olefinic radical in the ester may be methallyl, crotyl, tiglyl, cinnamyl, furfuryl, chloroallyl, bromoallyl, 2-hexenyl, or 2-decenyl. Many such esters are specified. The esters polymerize in stages, from a soluble to an insoluble thermoplastic resin and then to the thermosetting final product. The esters may be polymerized in presence of dyes, pigments or fillers. The esters may be co-polymerized with, for example, styrene, methylstyrene, 1 : 3-butadiene, cyclopentadiene, vinyl or allyl acetate, diallyl phthalate, methyl or ethyl acrylate, diallyl diglycolate, crotyl stearate, methyl vinyl ketone, methyl isopropenyl ketone, acrolein, methacrolein and acrylonitrile. Mixtures of the above p and mixtures of the phosphonates may be used.ALSO:Diesters of aryl phosphonic acids are prepared by reacting b : g -mono-olefinic monohydric alcohols with aryl phosphonyl dihalides, e.g. dichloride, preferably in presence of an acid-binding compound such as an organic amine, e.g. pyridine, or an inorganic base, e.g. sodium hydroxide. The temperature is preferably 0 DEG C. or lower, and an inert solvent, e.g. toluene, is employed. Preferably the aryl part contains no more than 9, and the alcohol no more than 10 carbon atoms. Specified aryl groups are phenyl groups substituted by methyl, ethyl, isopropyl and benzyl groups. Allyl alcohol is preferred but others specified include methallyl, crotyl, tiglyl, cinnamyl, furfuryl, chloroallyl and bromoallyl alcohols, also 2-hexenol, 2-octenol and 2-decenol. The esters may be isolated without distillation by washing with an aqueous base. A polymerization inhibitor, e.g. tannic acid, is preferably present during the reaction. In an example, diallyl phenylphosphonate is prepared by treating allyl alcohol and pyridine with phenyl phosphonyl dichloride in toluene at -35 DEG C. and then at 0 DEG C.
Dialkenyl alkanephosphonates and polymers thereof
Номер патента: US2601520A. Автор: Harman Denham,Alan R Stiles. Владелец: Shell Development Co. Дата публикации: 1952-06-24.