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Ooo-CH-CO-NH-CH-O-R

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Ooo-CH-CO-NH-CH-O-R 3,639,532 tented Feb. 1, 1972 Aal formula ROCHNHCO-, wherein R is alkyl. Therefore, ESTERS AND/OR AMiffs3,639,532 oF ACIDs oF PHos. this invention contemplates compounds having the for PHORUS CONTAINING A GROUP HAVING THE mula (ROCH2NHCO)R’, wherein R is alkyl, R' is ob FORMULA ROCHNHCO tained by removing all or part of the Zerewitinoff active Gunter Oertel, Cologne-Flittard, Hans Holtschmidt, hydrogen from a sulfur free ester or amide of an acid Leverkusen-Steinbuechel, and Wolfgang Carl, Dorma of phosphorus and n is a positive integer, preferably 1-6 gen, Germany, assignors to Farbenfabriken Bayer Ak which corresponds to the number of active hydrogens re tiengesellschaft, Leverkusen, Germany moved from said sulfur free ester or amide of an acid No Drawing. Filed Apr. 23, 1968, Ser. No. 723,584 of phosphorus. In the foregoing formula R is preferably Claims priority, application Germany, Apr. 25, 1967, 10 F 52,234 lower alkyl having 1-6 carbon atoms such as methyl, Int. C. C07f 9/24, C07d 105/02; C08f 45/85 ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert U.S. C. 260-923 4 Claims butyl, n-amyl, isoamyl, n-hexyl, 2-hexyl, 3-hexyl and the like. R' preferably represents the radical obtained by re moving one hydrogen atom which is reactive with an ABSTRACT OF THE DISCLOSURE 5 -NCO group (i.e., active as determined by the Zerewi tinoff method) from a sulfur free ester or amide of an Sulfur free esters and/or amides of acids of phosphorus acid of phosphorus having a molecular weight below 600. which contain at least one group having the formula When the molecular weight is above 600 the products ROCH2NHCO-, wherein R is alkyl, useful as additives are somewhat difficult to use as fire-resistant additives. for resins to impart flame-resistance. 20 The alkoxymethyl amide group, ROCH-NH-CO may be linked to the phosphorus acid moiety by a di This invention relates to phosphorus esters and/or rect bond to the phosphorus atom or through a linkage amides and more particularly to derivatives which have as illustrated in the equations below. improved ability to impart flame-resistance to resins and The compounds of the invention can be prepared, for the like. example, by the reaction between a Zerewitinoff active Phosphorus compounds are known to have flame-re hydrogen atom on an ester and/or amide of a sulfur free sistant properties. Many of them can therefore be used acid of phosphorus and an alkoxymethyl isocyanate ac to impart flame-resistance to resins including synthetic cording to the following equation resins and fibers. Thus, it has been known heretofore to use trichloroethyl or dibutyl phosphate as flame-resistant 30 R-H-I-OCN-CH-O-R-> additives for plastics, but these additives diffuse out and '-CO-NH-CH-O-R thus their effect is lost. In addition, some compounds where R and R' have the meanings set forth above. This which may have other utility, as the compounds of Ger leads to the phosphorylated N-alkoxymethylamide of the man Pat. 1,138,977 decompose in a flame or under high type characterized above, in which R" denotes the radi heat to produce noxious fumes and poisonous gases. cal of an ester or amide of an acid of phosphorus and R Others, even if they produce no undesirable by-products, denotes an alkyl radical regardless of which of the dif are themselves poisonous and cannot be used for textiles, ferent types of Zerewitinoff active hydrogen atoms de coatings, foamed plastics and the like for home use. Even scribed below is involved in the reaction. Examples of if all of these disadvantages are overcome, one must de 40 functional groups in esters or amides of acids of phos termine what effect the additive to impart flame-resistance phorus, and their conversion according to the invention will have on the other physical properties of the mate into N-alkoxymethylamide derivatives, are illustrated rial to be made flame-resistant. Many heretofore known schematically in the following equations. phosphorus additives only improve the flame-resistance of a substance at the expense of some other physical prop 45 erty such as color, tensile strength or the like. This is par ticularly true for textiles where one must pay attention -H -- OCN-CH-O-R - –co-NH-CH-O-R to hand, drape, absorbency, dyeing and dye-fastness, strength, durability, washfastness and cost. The hereto -NH2 - OCN-CH-O-R - H-NH-CO-NFH-CH-O-R fore known phosphorus compounds have suffered from 50 HCO-NH -- OCN-CH-O-R - one or more of the foregoing disadvantages. - CO-NH-CO-NH-CH-O-R It is therefore an object of this invention to provide new compositions of matter which do not have the forego -NH-NH -- OCN-CHNO-R - ing disadvantages and can, therefore, be used in the pro -NH-NH-CO-NH-CH-O-R duction of improved fire-resistant materials. Another ob 55 ject of this invention is to provide an improved process H-CO-NH-NH2 - OCN-CH-O-R --> of preparing addition products of esters and/or amides -CO-NH-NH-CO-NH-CH-O-R of acids of phosphorus which are free from sulfur. An O CO-CH other object of this invention is to provide improved fire -ob-bit, - OCN-CH-O-R --> resistant fibers, foils, textiles and the like. Still a further 60 object of this invention is to provide new compositions CO-CH of matter which will impart fire-resistance to plastic prod ucts without affecting their other properties. Still another -ooo-CH-CO-NH-CH-O-R object of this invention is to provide an improved way H-OH -- OCN-CH-O-R - HO-CO-NH-CH-O-R of rendering materials flame proof and/or flame-resistant. Another object of this invention is to provide a fire-resist HCOOH + OCN-CH-O-R -CO HCO-NH-CH-O-R ant polyurethane, polycarbonate, polystyrene and the like. The foregoing objects and other which will become ap H-NH-OH -- OCN-CH-O-R -) parent from the following description are accomplished -NH-O-CO-NH-CH-O-R in accordance with the invention, generally speaking, by providing sulfur free esters and/or amides of acids of 70 phosphorus which contain at least one group having the p-H -- OCN-CH-O-R - p-co-NH-CH-O-R 38.35 s 3,639,532 3 The functional groups in the above scheme can be C3 --- W N N / linked to the phosphorus atom of the ester or amide of - P-NH2, N-- - EP-NH-CH phosphorus through carbon, oxygen, nitrogen or direct w 2 / ly. One example of a direct link between the Zerewitinoff C H3 2 active hydrogen atom and the phosphorus atom is found 5. O O in the reaction, formulated in the last of the above equa tions, between a PH acid compound, e.g., a phosphorus acid diester, -diamide or -ester amide, and an alkoxymeth ylisocyanate. Esters and amides of acids of phosphorus which may O Yao be used as starting in the process according to the inven O O tion may contain one or more Zerewitinoff active hydro d HCH3OHE. : ICH2OH./ gen atoms which may be of the same type or different; for example, OH groups may be present together with NH groups, or PH groups may be present in the same molecule. C6H5 O CEI C2H5 O Furthermore, not all the Zerewitinoff active hydrogen / V atoms present in an ester or amide of an acid of phoS P--NH. P-CH OFI phorus need be reacted with alkoxymethylisocyanates. CHO CH3 C2H5O They may, in fact, react selectively and partially, espe 20 CH 9 / cially if they have different reactivities. P-CH-NH-... Cls The sulfur free esters or amides of acids of phosphorus Cl5O C.H. that may be used as starting materials for the reaction according to the invention are mainly esters and amides CHO / of phosphinous, phosphinic, phosphonous, phosphonic, F--CH2-CH2. OI phosphorous and phosporic acids. Any of these phosphorus / compounds may be used for the reaction with alkoxy CHO methylisocyanates, provided they have Zerewitinoff active / o hydrogen atoms in the molecule, e.g., in the form of the (NH-CH-CH-CH2-), P-N (-CH3)2 substituents mentioned by way of example in the above 30 scheme. It is essential, however, that the compounds be y free of sulfur because sulfur not only makes the com C.H.--O-(CHCH-0)-H, C.H.--0 CH3 pounds toxic and unsuitable for many uses, for example, H where they are used to flameproof substances that come W in contact with food, but also where the substance may be 35 y subjected to a fire. The sulfur-containing compounds react CEI -- (--OCEI-CH-CH2--CI-NH2) O with oxygen in a fire to produce noxious gases that are / | almost as harmful as the fire itself NH-CO-CH-P (-O C.IIs), Table I lists examples of sulfur-free esters of phos O O O CH phorous acids, wherein it will be noted that the compounds 40 I / / / (CH3O-)2P-CHCH-COOH, FFO-C-P have a total of 4 to 18 carbon atoms as benzene rings, 4 N.Y. straight or branched chain hydrocarbon groups of from CH3 CH3 OH 1 to 6 carbon atoms, and such hydrocarbon groups (1) O O CHs interrupted with a nitrogen or oxygen atom, or (2) sub M stituted with a hydroxy, amino, chloro or bromo group.
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