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United States Patent Office Patented Oct 3,346,667 United States Patent Office Patented Oct. 10, 1967 2 standing in humid environments, for example, polyure 3,346,667 thane made using a hydrolysis-prone phosphorous con PRODUCT PRODUCED BY REACTING PHOSPHO taining polyol of the prior art, e.g. one made with phos RUS OXDE OR SULFIDE, ANOXIRANE COM POUND, AND A HYDROXY OR THEOL COM phoric acid rather than POs will adsorb moisture and dis POUND TOGETHER, AND PROCESS integrate with consequent loss of strength, buoyancy and Francis G. Firth, 11580 Belagio Road, usefulness. Los Angeles, Calif. 90049 Accordingly, a principal object of this invention is to No Drawing. Filed Sept. 6, 1963, Ser. No. 307,020 provide new and improved phosphorus-containing com 10 Claims. (C. 260-920) positions, and a method for economically preparing such O useful materials. This invention relates to a new and improved phos A further object of the invention is to provide new and phorus-containing composition and method of preparing it. improved phosphorus-containing reaction products having The use of various phosphorus-containing compositions a high hydroxyl equivalence, an acid number less than is widespread and their utility is as diverse as the nature of 1.0 and a high concentration of chemically combined phos the phosphorus-containing products available. However, 5 phorus. despite wide areas of utility, there has been a continuing A still further object of the invention is the preparation need and interest, particularly in the field of syntheitc of novel chemical products highly resistant to hydrolytic plastics, although also in many other applications as here attack, containing a high percentage of phosphorus, a high inafter discussed, for phosphorus-containing materials em hydroxy equivalence and a low acid number. bodying hydroxyl or similar reactive terminations having 20 These and other objects and advantages of the invention low acid numbers, i.e., 1.0 or less, as well as satisfactory will appear more fully from the following description methods of preparing such compounds. thereof. In general, most commercially available phosphorus In general, this invention comprises the composition ob compounds heretofore used in applications such as plas tained by the reaction of, especially the simultaneous re ticizers, flame retardant additives for polymers, lubricating 25 action of, (1) phosphorus oxide or phosphorus sulfide, oil additives, corrosion inhibitors, detergents, hydraulic preferably phosphorus pentoxide, with (2) an oxyalkylat fluids, and the like, have been either neutral phosphoric ing agent and (3) a compound embodying at least one hy acid esters, such as organic phosphates of the type exem droxyl group or other source of an active hydrogen atom, plified by tributyl phosphate and tricresyl phosphate, or e.g., thiol group. more complex compounds such as trisbetachlorethyl phos 30 The term "phosphorus oxide,' as used in the specifica phate. For example, various neutral and acid esters of tion and claims, is intended to include as the phosphorus ortho and pyrophosphoric acid, e.g., ortho phosphoric pentoxide both POs and P4O10; thus, POs, and P4O10 acids of the structure: of the following structure are included: 35 have been long known and are now commercially avail able. However, esters of these types are generally non acidic and can be considered as chemically non-functional 40 because no chemically reactive groups are provided, such as by hydroxyl termination and none are available for Further, PO in the form described and claimed in U.S. further chemical reaction. Patent No. 3,077,382, Klein et al., also can be used. In ad Other prior forms of phosphorus-containing materials 45 dition, the term "phosphorus oxide” also is intended to in include alkyl acid phosphates which usually are mixtures clude phosphorus trioxide (PAOs) and phosphorus tetrox of partially-esterified phosphoric acids containing small ide (PO4). Similarly, the term "phosphorus sulfide,' as amounts of monohydric alcohols as well as free meta used in the specification and claims, is intended to include phosphoric acid and pyrophosphoric acid. For example, the pentasulfide (PS), the trisulfide (PAS), the sesqui commercial n-butyl acid phosphate generally contains 50 sulfide (PS3), and the heptasulfide (PAS). At present, about 39 percent of phosphorus and has an acid number phosphorus pentoxide and phosphorus pentasulfide are (expressed as milligrams of potassium hydroxide per gram more readily available and are preferred. Phosphorus of product) of 450. A commercial grade of dibutylpyro pentoxide is an especially preferred oxide and for that phosphate, exemplifying a complex mixture of various reason particular reference thereto is made throughout ortho, pyro and partially esterfied phosphates, typically 55 the specification. has a phosphorus content of about 22 percent and an The expression "oxyalkylating agent,” as used in the acid number of approximately 400. It is to be noted that specification and claims, is intended to refer to a com such acid phosphates, when considered chemically reac pound containing at least one reactive oxirane ring, i.e., tive at all, are found to have reactivity primarily due to their acidity and are used in applications where this feature 60 -C-in-C- is significant. Because of the ability to impart flame retardancy to compositions containing them, and other advantageous Illustrative examples of suitable oxyalkylating agents are properties of phosphorus compounds, it is highly desir styrene oxide, benzylethylene oxide, phenylglycidyl ether, able to provide, and there has been a continuing need for, 65 and allyl glycidyl ether. In addition, the term "oxyalkylat relatively low cost polyfunctional phosphorus-containing ing agent' also is intended to include compounds such materials embodying different chemical substituents such as epichlorohydrin, glycerol monoglycidyl ether, glycerol as alkyl, aromatic, alicyclic, and the like. diglycidyl ether, glycerol triglycidyl ether, 1-heptylene In addition, a significant problem heretofore encoun oxide, alkylene oxides, such as ethylene oxide, propylene tered in the use of prior phosphorus-containing com oxide, butylene oxide, diisobutylene oxide, glycidyl acryl positions in diverse applications has been a susceptibil 70 ate, vinyl cyclohexene dioxide, and the like. ity to hydrolysis with subsequent loss of effectiveness. On Illustrative of suitable compounds containing an active. 3,346,667 3 4. hydrogen atom, especially a hydrogen atom from an at oxyalkylating agent and hydroxyl-containing compound tached hydroxyl or thiol group, are hydroxyl-containing (or other compound containing an active hydrogen atom) compounds, including monoalcohols or alkanols, such as are generally charged into the reaction vessel first, in a ethyl alcohol, butyl alcohol, allyl alcohol, n-butyl alcohol, manner Such that substantially no reaction occurs in the isobutyl alcohol, sec. butanol, tertiary butanol, hexyl al absence of externally-applied heat, and with agitation of cohol, cyclohexanol, capryl alcohol, cetyl alcohol, Stearyl the contents of the reaction vessel the phosphorus oxide, alcohol, benzyl alcohol, as well as corresponding alkenols, phosphorus sulfide, or mixture thereof, is added thereto cycloalkanols, and the like; illustrative polyalcohols are slowly either as a dry powder, or, preferably, in the form glycerol, trimethylolpropane, propylene glycol, ethylene of a fine suspension or slurry in an inert liquid medium, glycol, 1,4-butanediol, 1,3-butylene glycol, triethylene 10 Such as one of the chlorinated hydrocarbons previously glycol, hexamethylene glycol, pentaerythritol, arabitol, disclosed, in order to effect the desired simultaneous re mannitol, monosaccharides, polysaccharides, inositol, action. sorbitol, sucrose, methyl glucoside, polyoxyalkylene gly When oxyalkylating agents which are gases at room cols, hydroxyl-bearing polyesters, polyvinyl alcohols, temperature are used, the reaction system can be pres cyclohexane diols, cyclopentane diols, natural, Synthetic 15 surized to maintain a liquid phase in the reaction vessel and modified hydroxyl-bearing oils, cottonseed oil, corn and the phosphorus pentoxide or phosphorus pentasulfide oil, lard oil, soybean oil, castor oil, rapeseed oil, inseed introduced under pressure, e.g., as a slurry. On the other oil and peanut oil; suitable mono and polyhydric amino hand, if the oxyalkylating agent is normally a liquid at alcohols are primary, secondary and tertiary, dimethyl room temperature, the phosphorus pentoxide or phos aminoethanol, triethanolamine, diethylaminopropylamine, 20 phorus pentasulfide may be introduced simply by sifting n-hydroxyethylpentamethylene diamine, tris (hydroxy it slowly into the agitated reaction mixture, with due pre ethyl)triethylenetetramine, polytetramethylene glycols, cautions against the phosphorus pentoxide or phosphorus polyalkyleneether thioglycols and thiols generally, specifi pentasulfide absorbing moisture from the atmosphere. cally including thiols corresponding to the foregoing. In any event, the resulting simultaneous reaction is Other illustrative compounds also include mono or poly 25 exothermic and fast; in some instances, the energy re nuclear phenols with hydroxyl or thiol groups present leased has been measured to be in excess of 1200 B.tu.'s such as phenol, catechol, resorcinol, hydroquinone, pyro per pound of phosphorus pentoxide used, while a much gallol, phloroglucinol, cresols, xylenols, naphthols, hal slower reaction occurs using phosphorus pentasulfide;
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