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United States Patent Office Patented May 7, 1968 1 3,382,301 United States Patent Office Patented May 7, 1968 1. 2 3,382,301 where R is alkyl, alkenyl, aralkyl or R, R is alkyl, DHYDROXY PHOSEPHONATES alkenyl, aralkyl, aryl, haloaryl or R and R is Ingenuin Hechenbleikner, Kenwood, and Kenneth R. Moit, Cincinnati, Ohio, assignors to Carlisle Chemical Works, R6 R3 R4 Rs Inc., Reading, Ohio, a corporation of Ohio 5 -(CHCHo). (CH)-6-d No Drawing. Continuation-in-part of application Ser. No. 245,976, Dec. 20, 1962. This application Sept. 3, 1964, () ) Ser. No. 394,320 N c^ 5 Claims. (C. 260-953) R? Y, 0 where R1 is hydrogen alkyl, aryl, haloaryl or nitroaryl, R2 is hydrogen, alkyl aryl, haloaryl or nitroaryl; or ABSTRACT OF THE DISCLOSUIRE Dihydroxy phosphonates of the formula RO O Rs R4 Rs is an alicyclic, i.e., a cycloalkyl group, R3 is hydrogen, N b. alkyl or aryl, R4 is hydrogen or alkyl, R is hydrogen or P-(CH-CHO) (CH)-- alkyl, R6 is hydrogen, or lower alkyl, e.g., methyl or RO OB OH ethyl, v is 0 or an integer, e.g., from 1 to 100, n is an 20 integer between 1 and 10, m is 1 or 2; where R1 and R2 are selected from the group consisting of 90-ce CH-O R alkyl, alkenyl, monocyclic carbocyclic aryl, naphthyl, R10 benzyl, alkylbenzyl and halophenyl; / Yr, R8 is selected from the group consisting of hydrogen and lower alkyl; R and R5 are selected from the group consisting of where Rio is alkyl, alkenyl or aralkyl and R1 and R2 are hydrogen and alkyl; as defined above Ra is selected from the group consisting of hydrogen, alkyl and monocyclic carbocyclic aryl; O R O y is an integer of at least Zero; R10- 1–0CH)-o-C-O-CH).o 1-R, m is an integer between 1 and 2 inclusive; and R11- l, () R n is an integer between 1 and 10 inclusive, are prepared by hydrolyzing corresponding 1,3-dioxolanes and 1,3-di III OXalcS. where R11 is alkyl, alkenyl aryl, haloaryl or aralkyl and -a assrs. Scramma R1,R2, and Rio are as defined above This application is a continuation-in-part of application is . 245,976, filed Dec. 20, 1962, now Patent 3,206,474, which in turn is a continuation-in-part of application 214,508, 40 R--OCHCHo)-ochschooooh,dhoolcho.--RsR11-O R2 R11 filed Aug. 3, 1962, now Patent 3,096,345 issued July IV 2, 1963. The present invention relates to novel phosphonates. where R1, R2, R6, R10, R11 are as defined above and x is It is an object of the present invention to prepare phos an integer of at least 1, e.g., from 1 to 100. phonates of polyhydric alcohols having at least three There are also included phosphonates of diacetals and hydroxyl groups. ketals or hexitols such as sorbitol and mannitol. Typical Another object is to prepare novel heterocyclic acetal of such materials are compounds having the formula and ketal phosphonates. A further object is to prepare novel phosphonates by R the hydrolysis of acetal and ketal phosphonates. A still further object is to prepare novel open chain acetal and ketal phosphonates. Still further objects and the entire scope of applicability of the present invention will become apparent from the C--O O. detailed description given hereinafter; it should be under stood, however, that the detailed description and specific CH-O examples, while indicating preferred embodiments of the v invention are given by way of illustration only, since various changes and modifications within the spirit and where R1,R2 and Rio are as defined above. scope of the invention will become apparent to those 60 In Formula V no attempt has been made to show the skilled in the art from this detailed description. position of the hydrogen atoms on the asymmetric car It has now been found that these objects can be attained bon atoms. The position of the acetal and ketal groups by preparing novel acetals and ketals having one of the also can be varied so long as there are two such groups formulae in the molecule. The compounds of the present invention are useful as water dispersible wetting and suspending agents. They can also be employed as fire retardants for cellulose, R7-P-ORg cellulose esters, e.g. cellulose acetate, polyolefin resins, e.g. polyethylene and polypropylene. A particular important use for the acetals and ketals of the present invention is to hydrolyze them to give hy 3,382,301 3 4 droxyl containing phosphonates. Such hydroxyl contain or superatmospheric pressure. The halide remaining after ing phosphonates have the following formulae the reaction can normally be removed by distillation. Among the halides which are employed in the Arbuzov reaction are R-0 R13 5 methyl bromide, methallyl iodide, methyl iodide, crotyl bromide, ethyl bromide, vinyl bromide, wherein R is as defined above, R12 is alkyl, alkenyl, ethyl iodide, oleyl bromide, aralkyl, aryl, haloaryl or R13 and R13 as n-propyl iodide, oleyl iodide, Rs R3 R R5 O isopropyl iodide, benzyl chloride, amyl bromide, benzyl bromide, -(CH&Ho) (CH)-b-cé. amyl chloride, benzyl iodide, ÖH. Ó It amyl iodide, o-dodecylbenzyl chloride, where R3, R4, R5, R6, V, in and m are as defined above; butyl bromide, p-dodecylbenzyl chloride, 5 hexyl iodide, m-dodecylbenzyl chloride, O OCH CH2OH. octyl bromide, p-dodecylbenzyl bromide, R octyl iodide, epichlorhydrin, YoCH/ YoHoH decyl bromide, epibromohydrin, WI decyl iodide, epiiodohydrin, dodecyl iodide, ethylene chlorhydrin, wherein Rio is as defined above; octadecyl bromide, ethylene bromohydrin, HCO octadecyl iodide, ethylene iodohydrin, HO bH allyl bromide, propylene chlorhydrin, CHOH allyl iodide, propylene bromohydrin. Hob O allyl chloride, The compounds of Formulae VI through VIII are pre pared by hydrolysis of the compounds of Formulae I, II, and V. The hydrolysis is carried out with the aid of water, WII 30 preferably with heating, e.g. up to 100° C. The reaction where Rio is as defined above. mixture is usually slightly acidic due to the starting phos The hydrolyzed phosphonates, i.e. the compounds of phonate. After hydrolysis is completed, an alkaline mate Formulae VI, VII, and VIII, have the uses set forth rial, e.g. sodium hydroxide, sodium carbonate, sodium bi Supra and in addition are useful for preparing polyure carbonate or potassium hydroxide is added to neutralize thanes by reaction with organic isocyanates, e.g. toluene 35 the product. diisocyanate and PAP (polyphenylene isocyanate aver Illustrative examples of starting phosphites (which can aging about 3 units in the poymer). The polyurethanes be prepared in the manner set forth in the parent applica can be prepared as foams or as elastomers. The presence of the phosponate group renders the polyurethane flame tion) to prepare the phosphonates of Formula I are resistant. The phosphonate need be used only as a portion 40 phenyl bis (4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) of the polyols employed. Thus, the use of 20% of a methyl) phosphite diphenyl-4-(2-methyl-2-ethyl-1,3- polyhydroxyl containing phosphonate according to the dioxacyclopentyl) methyl phosphite; present and 80% of another polyol, e.g. glycerine pro methyl bis (4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl)- pylene oxide adduct molecular weight 3000 or polypro methyl) phosphite; pylene glycol 2025 will give a polyurethane with im dimethyl 4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl)methyl proved flame resistance. phosphite; The novel compounds of Formulae I through V of the ethyl bis(4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl)- present invention are prepared by Arbuzov rearrange methyl) phosphite, ment of the corresponding phosphite prepared according tris(4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) methyl) to the parent application. The entire disclosure of the parent application is hereby incorporated by reference. phosphite; Thus, there is employed an alkyl halide, alkenyl halide, decyl bis(4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) aralkyl halide, halohydrin or epihalohydrin with a phos methyl) phosphite; phite of the parent application that is isomeric with a octadecyl bis(4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) phosphonate of Formulae I through V above. The iodides methyl) phosphite; and bromides are preferred although there can also be dioctadecyl 4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) employed the chlorides. The halides can be employed in methyl phosphite; catalytic amounts, e.g. 0.5-5 mol precent based on the oleyl-bis (4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) phosphite to be rearranged. If the hydrocarbon group of methyl) phosphite; the halide is the same as one of the esterifying groups of 60 benzyl-bis (4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) the phosphite, then no impurities are introduced into the methyl) phosphite; phosphonate product. By employing a large amount of p-dodecylbenzyl-bis (4-(2-methyl-2-ethyl-1,3-dioxacyclo the halide, e.g. 80 mol percent, or perferably 100 mol pentyl) methyl) phosphite; percent or more, based on the phosphite employed in cyclohexyl-bis-(4-(2-methyl-2-ethyl-1,3-dioxacyclopentyl) the Arbuzov reaction, then the product is one in which 65 methyl) phosphite; one of the esterifying groups on the phosphorus atom is tris (5-(2,5-dimethyl-2-ethyl-1,3-dioxacyclohexyl)methyl) removed and the phosphorous atom is directly attached phosphite; to the hydrocarbon, hydroxyhydrocarbon or epoxyhydro ethyl-bis (5-(2,5-dimethyl-2-ethyl-1,3-dioxacyclohexyl) carbon group of the halide employed. When one of the methyl) phosphite; esterifying groups of the phosphite is aryl or haloaryl, 70 dimethyl-5-(2,5-dimethyl-2-ethyl-1,3-dioxacyclohexyl) sufficient alkyl halide or the like must be used to re methyl phosphite; place the aryl or haloaryl group since aryl halides do lauryl-bis-(5-(2,5-dimethyl-2-ethyl-1,3-dioxacyclohexyl) not normally take part in the Arbuzov reaction.
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