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United States Patent (19) 11) 4,177,300 Walsh Et Al

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United States Patent (19) 11) 4,177,300 Walsh Et Al United States Patent (19) 11) 4,177,300 Walsh et al. 45) Dec. 4, 1979 54 PHOSPHONOXYCARBOXAMIDE FLAME RETARDING COMPOSITIONS OTHER PUBLICATIONS Shiskin et al., "Methylphosphonic Acid Esters Contain 75 Inventors: Edward N. Walsh, New City; Ralph ing the Carbamoyl Group', C.A. 13602v, vol. 81, 1974. B. Fearing, Bardonia, both of N.Y. Shiskin et al., "Dialkyl Methylphosphonates with a Carboximidic Ester Hydrochloride Grouping in One of 73) Assignee: Stauffer Chemical Company, the C-Alkyl Groups', Journal of General Chemistry of Westport, Conn. USSR, vol. 46, No. 10, PL 1, pp. 2143 to 2146 (transla tion) (1976). (21) Appl. No.: 905,307 Primary Examiner-John D. Smith (22 Filed: May 12, 1978 Attorney, Agent, or Firm-William C. Gerstenzang 57 ABSTRACT Related U.S. Application Data Novel phosphonxycarboxamides of the formula: 62 Division of Ser. No. 837,072, Sep. 28, 1977. O O 3 51) Int. Cl?............................ COTF 9/11; CO7F 9/40 Rl-P-O-R-C-NC R ) 52 U.S. C. ................................ 427/390 D; 252/8.1; NR4 260/943; 427/394; 106/18.15 (RO)2- 58 Field of Search ........................... 427/390 D, 394; 260/943; 252/8.1; 106/18 FP wherein R and R2 are selected from the group consist ing of aryl and alkyl having from 1-6 carbon atoms and 56 References Cited may be the same or different; R3 represents hydrogen or U.S. PATENT DOCUMENTS -CH2OH.; R represents hydrogen, -CH3, -CH2OH, or -C2H4OH, R represents an alkyl group having 2,494,283 1/1950 Cassaday et al. .................... 260/943 3,644,140 2/1972 Weisz et al. ..................... 427/390 D from 1-5 carbon atoms; and n represents 1 or 2 are 3,669,725 6/1972 Nachbur et al. ................ 427/390 D useful as flame retardant agents for textile materials. 3,763,283 10/1973 Curgan ................................. 260/938 4,028,053 6/1977 Duke ............................... 427/390 D 7 Claims, No Drawings 4,177,300 1. 2 PHOSPHONOXYCARBOXAMIDE FLAME O O RETARDING COMPOSTIONS R' This is a division of application Ser. No. 837,072 filed 5 R!--O-R-C-N-(RO)2- R n Sept. 28, 1977. This invention relates to new and useful phosphonox wherein R and R2 are selected from the group consist ycarboxamides and their method of preparation. More ing of aryl and alkyl having from 1-6 carbon atoms and particularly, this invention relates to new phosphonox may be the same or different; R represents hydrogen or ycarboxamide compounds which are useful as agents O -CH2OH; R represents hydrogen, -CH3, -CH2OH, for imparting flame retardance to textile materials such or -C2H4OH, R represents an alkyl group having as cotton fabric or yarn. from 1-5 carbon atoms; and n represents 1 r 2; (2) an It has long been known that flame retardant proper aminoplast; and (3) an acid catalyst. In preferred em ties may be incorporated into textile materials such as bodiments, the flame-retardant composition is an aque cotton fabric or yarn by treatment with phosphorus 15 ous formulation wherein the aminoplast is present at a containing compounds. Such compounds are usually in concentration ranging from about 10 to about 600 per the form of organophosphorus compounds which are cent by weight of the phosphonoxycarboxamide com relatively harmless to the material being treated as well pound, the acid catalyst is present at a concentration as resistant to laundering. ranging from about 0.01 to about 5 percent by weight of 20 the phosphonoxycarboxamide, and the total concentra More recently, it has been discovered that organic tion (i.e., the "solids' content) of the phosphonoxycar nitrogen is a synergist for phosphorus-induced flame boxamide, aminoplast, and catalyst is adjusted to pro retardance in cellulosic fabrics, and its presence in the vide a phosphorus uptake of 1 to 5% by weight on the flame-retardant compound permits a reduction in the fabric being treated. amount of flame retardant which is required to achieve 25 In accordance with a further aspect of this invention, an acceptable degree of flame retardance. Exemplary of there is provided a process for imparting flame retard flame-retardant compounds which contain both nitro ance to textile materials comprising the steps of impreg gen and phosphorus are those disclosed in U.S. Pat. nating the textile material with a flame-retardant com Nos. 3,268,292; 3,374,292; 3,556,840; 3,634,422; position comprising: 3,763,283; and 3,835,204. 30 (a) at least one compound represented by the formula: It is an object of this invention to provide a novel class of phosphonoxycarboxamide compounds which are effective in imparting flame retardance to textile materials. It is another object of this invention to pro f R: vide novel compositions which may be used at rela 35 Rl-e-o-R5-3-NC), tively low add-on weights to impart flame retardance to R4 textile compositions. It is a further object of this inven tion to provide a novel process by which flame retard wherein R1 and R2 are selected from the group consist ancy may be imparted to textile materials. ing of aryl and alkyl having from 1-6 carbon atoms and In accordance with one aspect of this invention, there may be the same or different; R3 represents hydrogen or is provided a compound of the formula: -CH2OH.; R represents hydrogen, -CH3, -CH2OH, or -C2H4OH; R represents an alkyl group having O O R3 (1) from 1-5 carbon atoms; and n represents 1 or 2; (b) an I 45 aminoplast; and (c) an acid catalyst and heating the impregnated textile material to a temperature sufficient to cure the flame-retardant composition. (rib- Y. The phosphonoxycarboxamides of this invention may wherein R1 and R2 are selected from the group consist be prepared by a variety of techniques known in the art. ing of aryl and alkyl having from 1-6 carbon atoms and 50 For example, when n=1, they may be prepared by may be the same or different; R3 represents hydrogen or reacting a carbalkoxyalkyl phosphonate such as a carb -CH2OH.; R“represents hydrogen, -CH3, -CH2OH, alkoxy methyl phosphonate, i.e., or -C2H4OH, R5 represents an alkyl group having from 1-5 carbon atoms, provided that only one of R: O O (II); and R may be hydrogen; and n represents 1 or 2. 55 RI-P-O-CH-C-OR6 Within the broad class of compounds encompassed by this invention, a particularly preferred subclass com prises those compounds wherein R represents an alkyl wherein R and R2 are as defined hereinabove, and R6 radical of from 1-4 carbon atoms; R2 represents an alkyl 60 represents an alkyl group having from 1 to 2 carbon radical of from 1-2 carbon atoms; R3 represents hydro atoms; with ammonia, i.e., NH3 to form an N- unsubsti gen or -CH2OH.; R represents hydrogen, -CH3, tuted phosphonoxycarboxamide -CH2OH, or -CH2CH2OH, R5 represents -CH2; and n represents 1 or 2. O O H (III); In accordance with another aspect of this invention, 65 / Rl-P-O-CH2-C-N there is provided a flame-retardant composition com N prising: (1) at least one compound represented by the R2O H formula: 4,177,300 3. 4. or with a primary amine such as, for example, methyl amine, ethanolamine, or the like to form a partially -continued N-substituted phosphonoxycarboxamide, e.g., ch,--och, + 2C1-CH2-C-OC2H5-Ge. 5 O O H (IVA); CH3O / O O I (IIA) R-i-o-CH-C-NR2O CH3 or O O H 10 The N- unsubstituted or partially substituted phos / phonoxycarboxamides which are prepared by reacting R!--o-ch-c-N the precursor phosphonates with either ammonia or a R2O C2H4OH primary amine may then be condensed with an alde hyde to form the alkyloamides. Aldehydes which may This reaction may be conducted in a solvent which is 15 be used for this purpose include, but are not limited to, nonreactive towards either the starting reagents or the formaldehyde, acetaldehyde, and glyoxal. the alkylol resulting phosphonoxycarboxamide. Suitable solvents amides may then be reacted with an aminoplast to form include, but are not limited to water, methanol, ethanol, a water-insoluble resin. Aminoplasts which may be used ethylene glycol, diethyl ether, acetone, toluene, and the for this purpose include, but are not limited to, me like. The reaction is conducted at a temperature ranging 20 thylol- and methoxymethylmelamines, methylolated from about 0° C. to about 40 C. and generally requires ureas, and cyclic ureas such as dimethyloldihydroxye a reaction time ranging from about 2 to 20 hours. thyleneurea. The phosphonoxy-bix-carboxamide compounds (i.e., For example, Compound III may be methylolated by Compound I wherein n=2) of this invention may be reaction with formaldehyde, which can be in gaseous, prepared using the same procedures as described above 25 liquid solution, or solid form, over a period of from except that a bis-carbalkoxyalkyl phosphonate, i.e., about 0.5 to about 2 hours at a temperature ranging from about 55 to about 85°C. while maintaining the O O (IIA) system at an alkaline pH, preferably in the range of I about 7.5 to about 8.5. The product of this reaction 30 using Compound III will be a mixture of the monometh ylol substituted derivative (V) and the dimethylol deriv is used as a starting material instead of a carbalkox ymethyl phosphonate (II). ative (VI): The precursor phosphonates (Compounds II and 35 O O H (V) IIA) used in preparing the novel phosphonoxyaceta | M. RI-P-O-CH-C-N mides of this invention may be prepared by reacting an R2O alkyl, aryl, alkylaryl, or arylalkyl phosphonate with an CH2OH alkyl halo alkanoate at a temperature ranging from and about 125° C.
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