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United States Patent Office Patiented Oct 3,281,502 United States Patent Office Patiented Oct. 25, 1966 2 acid (about 6 mols per mol of acid) to produce a neu PHOSPHORUS AC DiAEOFYDRIN3,281,502 COMPOUNDS tral product sufficiently reactable with polyisocyanates taud E. Peietier, Elmwood Park, and Floy Pelletier, for polyurethane foam production, the foam product is Lockport, E., assignors, by mesne assignments, to Wy not Self-extinguishing or non-inflammable. Using epi andotte Chemicals Corporation, a corporation of Michi chlorohydrin in accordance with the invention to provide gara a halohydrin compound containing both hydroxyl groups No Drawing. Filled May 22, 1959, Ser. No. 814,967 and chlorine Substitutents enables the provision of at 5 Claims. (C. 260-920) least Substantially neutral products which are reactive with polyisocyanates to form non-inflammable and self The present invention relates to halohydrin compounds 10 extinguishing polyurethane foams. produced by reaction of a phosphorus acid with a halogen At least 1 mol of halogen-substituted monoepoxide is substituted aliphatic monoepoxide, these halohydrin com reacted with each mol of phosphorous acid and, in ac pounds possessing various utility, particularly as inter cordance with the preferred practice of the invention, mediates for the production of synthetic resins possess Sufficient total aliphatic monoepoxide (halogen-substitut ing improved resistance to burning and flame propaga 15 ed or not) is reacted with the phosphorus acid to pro tion. The halohydrin compounds of the invention are vide an at least substantially neutral halohydrin com of outstanding utility when reacted with polyisocyanates pound. Thus, and using orthophosphoric acid as illus to produce polyurethane resins, especially when the re trative, the reaction of about 5 or more mols of epi action takes place in the presence of water or other blow chlorohydrin with orthophosphoric acid produces a neu ing agent to produce polyurethane foams characterized 20 tral halohydrin compound reactable with polyisocyanates by non-inflammability and the capacity to self-extinguish to provide a satisfactory self-extinguishing polyurethane fires. The halohydrin compounds are also of value when foam. When from 1 to about 4 mols of epichlorohy reacted with polycarboxylic acids to form polyesters and drin is reacted, the polyurethane foam does not possess these halohydrin compounds also provide a source of the Superior physical characteristics provided when about new epoxy resins. 5 or more mols of epichlorohydrin are used, but the In accordance with the invention, a phosphorus acid, foam product is self-extinguishing. However, reacting such as orthophosphoric acid, is reacted with a halogen 3 mols of epichlorohydrin with 1 mol of orthophosphoric substituted aliphatic monoepoxide, such as epichlorohy acid followed by reacting 3 mols of an olefin oxide such drin, to provide halohydrin compounds and preferably at as ethylene oxide, propylene oxide, 1,2-butylene oxide least substantially neutral halohydrin compounds. 30 or any monoepoxide compound having the 1,2 oxirane Various phosphorus acids may be used, orthophos group, such as styrene oxide, with the initial acidic epi phoric acid being preferred. Pyrophosphoric acid and chlorohydrin-phosphoric acid reaction product provides phosphorous acid also produce good results. Metaphos a chlorohydrin compound which will yield a satisfactory phoric acid as well as partial esters of the polyhydroxy self-extinguishing polyurethane foam of superior physical phosphorus acids such as the mono- and di-esters of or characteristics. thophosphoric acid, the mono-esters of phosphorous acid, The chlorohydrin compounds of the invention may be and the mono-, di- and tri-esters of pyrophosphoric acid, used alone for reaction with polyisocyanates or in ad such as dimethyl acid pyrophosphate and ethyl acid phos mixture with other compounds reactable therewith such phate, are also usable in the invention. as hydroxyl-containing polyesters and polyethers. What It is preferred to employ the selected phosphorus acid 40 ever proportions of the chlorohydrin compounds of the or mixture of acids in the absence of free water since invention are used in the mixture provides an improve water is independently reactive with the halogen-substi ment in fire resistance, and it is preferred to use enough tuted monoepoxide so long as the reaction mixture is suf to provide self-extinguishing character to the foam ficiently acidic. However, the invention includes the pres product. ence of water in the reaction mixture as well as the The halohydrin compounds of the invention are adapted presence of water or water-epoxide reaction product in to diverse other utility in addition to the utility illus the final product which is produced. trated above with reference to production of polyure The halogen-substituted aliphatic monoepoxides which thane foam products of improved flame resistance. Thus, are preferred in accordance with the invention have the the polyurethane product need not be foamed provid formula: 50 ing various rubbers, coatings and textile treating agents as is known to the art. Also the halohydrin compounds may be used as a source of organic polyhydroxy com pound for reaction with polycarboxylic acids such as maleic or fumaric acids or anhydrides to provide poly in which X is selected from the group consisting of hy esters. Further, the halohydrin compounds of the in drogen, halogen and organic hydrocarbon radicals, Y is vention may be partially or completely dehydrohalo a halogen and R is selected from the group consisting genated to produce epoxy resins. A number of alkaline of hydrogen and organic hydrocarbon radicals. materials may be used for the dehydrohalogenating treat The preferred epoxide is epichlorohydrin. Other epox ment with varying degrees of efficiency. Various suit ides which may be used are illustrated by trichloromethyl 60 able dehydrohalogenating agents include sodium hydrox ethylene oxide, c-methyl epichlorohydrin, epiiodohydrin, ide and basic reacting metal salts of strong bases and epifluorohydrin, epibromohydrin, 3-heptylepichlorohy Weak acids such as the hydroxides and oxides of mag drin, ox-cyclohexylepichlorohydrin, {3-phenylepibromo nesium, zinc, lead, iron and aluminum as well as var hydrin, and cy-allylepichlorohydrin. ious aluminates, silicates and zincates, as disclosed in It is known as taught, for example, in United States United States Patent 2,581,464 may be used to effect Patent 2,372,244, to react phosphoric or phosphorous the desired dehydrohalogenation. Representative dehy acids with olefin oxides to produce reaction products drohalogenation agents which are preferred are alumi possessing primary hydroxyl groups as indicated by the nates of alkali metals, such as NaAlO3, NaAlO, reaction equations set forth in said patent. Na2Al2O.xH2O (where x represents the quantity of asso The products of the invention are very different from 70 ciated water), K2Al2O4; Zincates of alkali metals, prin those of Patent 2,372,244 since when sufficient propylene cipally sodium and potassium, and silicates of alkali met oxide is reacted with phosphoric acid or phosphorous als, either anhydrous or hydrated orthosilicates, metasili 8,281,502 3. 4. cates, disilicates, trisilicates, sesquisilicates, etc. Typical EXAMPLE III of such materials are Na2SiO3.5H2O, 3Na2.2SiO2.5H2O, To the product of Example II, 450 grams of ethylene NaSiO4 and Na2SiO3. oxide were added under a pressure of 10-30 centimeters Dehydrohalogenation can be effected in either aqueous of mercury, and the reaction temperature was maintained or non-aqueous medium, temperatures in the range of 70– 5 at 90-120 F. by means of water cooling. After addi 105° C. being particularly preferred for the dehydrohalo tion of ethylene oxide, the reaction temperature was in genation reaction. creased slowly to 170 F., and this reaction temperature Thus, the various halohydrin compounds which may be was maintained for 1% hours. Vacuum was then ap produced in accordance with the invention may be de plied to remove free oxide. The final yield was 1425 hydrohalogenated to form epoxy resins which may be O grams of a clear, faintly yellow colored liquid product used as such, or upgraded by reaction with a dihydric which was free of acid and possessed a hydroxyl number organic compound such as bisphenol A, or employed in of 290 (acetylation method). admixture with conventional epoxy resins such as those produced by reaction of epichlorohydrin with polyhydric EXAMPLE IV organic compounds, notably bisphenol A, followed by A typical foaming composition was prepared using the dehydrohalogenation of the polyhalohydrin ethers so pro halohydrin compound obtained in Example I as follows: duced to form polyglycidyl ethers. The epoxy resins Quasi prepolymer composition which can be formed from the phosphorus-containing Parts halohydrin compounds of the invention are curable to Halohydrin compound of Example I ----------- 14.5 form films, coatings, molded products, etc., by employing 20 Tolylene diisocyanate (80/20 mixture of the 2,4 conventional epoxy resin curing agents known to the art. and 2.6 isomers) ------------------------- 58.00 These are illustrated by basic curing agents which are (React at 200 F. for 1 hour-Cool to 70° F. and preferably polyamines, e.g., triethylene tetramine, or acid cap in moisture free container-Viscosity at 80 curing agents such as phthalic acid, or Friedel-Crafts F.-cps. Analyzed NCO-32.) catalysts which are preferably illustrated by boron tri 25
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