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(12) Patent Application Publication (10) Pub. No.: US 2016/0281001 A1 BUTZ (43) Pub

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(12) Patent Application Publication (10) Pub. No.: US 2016/0281001 A1 BUTZ (43) Pub US 20160281 001A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0281001 A1 BUTZ (43) Pub. Date: Sep. 29, 2016 (54) FLAME RETARDANT COMPOSITION (52) U.S. Cl. CPC ............. C09K 21/12 (2013.01); C07F 9/4068 (71) Applicant: THOR GMBH, Speyer (DE) (2013.01); C07D 251/54 (2013.01); C08K 5/5317 (2013.01); C08K 5/34922 (2013.01); (72) Inventor: Volker BUTZ, Neustadt/Weinstrasse C08K 5/34928 (2013.01); C08J 5/18 (DE) (2013.01); C08J 9/40 (2013.01); C08J 2323/06 (2013.01) (21) Appl. No.: 15/022,715 (57) ABSTRACT (22) PCT Filed: Sep. 10, 2014 The invention relates to a flame retardant composition comprising a salt of components (A) and (B), wherein (A) (86). PCT No.: PCT/EP2014/OO2445 is at least one pyrophosphonic acid derivative of the general formula (I): S 371 (c)(1), (2) Date: Mar. 17, 2016 I (30) Foreign Application Priority Data (I) Sep. 17, 2013 (EP) .................................. 13OO4537.O o--0--0 R1 R2 Publication Classification where R' and Rare each independently a substituted or unsubstituted, straight-chain or branched alkyl group (51) Int. Cl. having 1 to 4 carbonatoms, Substituted or unsubstituted C09K 2L/2 (2006.01) benzyl or substituted or unsubstituted phenyl, and (B) C07D 251/54 (2006.01) is selected from the group consisting of melamine, C89/40 (2006.01) melam, melem, melon, ammeline, ammelide, 2-urei CSK 5/3492 (2006.01) domelamine, Substituted or unsubstituted heptazine, COSW 5/8 (2006.01) guanylurea, acetoguanamine, benzoguanamine and C07F 9/40 (2006.01) diaminophenyltriazine or two or more of these com CSK 5/537 (2006.01) pounds. US 2016/0281 001 A1 Sep. 29, 2016 FLAME RETARDANT COMPOSITION nylon-6,6. These flame retardants too may still have almost satisfactory flame retardancy in polyamides, but still do not 0001. The invention relates to a flame retardant compo exhibit satisfactory efficacy in polyolefins in particular. sition comprising a salt of components (A) and (B), wherein 0007 Document EP 0363 321 A1 describes melamine (A) is at least one pyrophosphonic acid derivative of the salts of methylphosphonic acid as flame retardants. The general formula I: melamine salts can be prepared by reaction of methylphos phonic acid or the monomethyl ester thereof with melamine. The disadvantage of these salts is that they are compara (I) O O tively hygroscopic, and still do not have satisfactory thermal stability. 0008 Proceeding from the prior art, it is an object of the o--0--0 invention to provide a flame retardant based on melamine derivatives and a phosphorus-containing compound, which can be produced in an economically viable manner. It is a I0002 where R' and R are each independently a substi particular object of the invention to provide a flame retardant tuted or unsubstituted, straight-chain or branched alkyl which has high thermal stability and is hygroscopic only to group having 1 to 4 carbon atoms, Substituted or unsubsti a small degree. It is a further object of the invention to tuted benzyl or substituted or unsubstituted phenyl, and (B) provide a flame retardant which has high efficacy in the is selected from the group consisting of melamine, melam, polymer, especially in polyolefins, and can therefore be melem, melon, ammeline, ammelide, 2-ureidomelamine, incorporated in Smaller amounts, as a result of which the Substituted or unsubstituted heptazine, guanylurea, properties of the polymer are affected to a smaller degree. acetoguanamine, benzoguanamine and diaminophenyltriaz 0009. This object is achieved by a flame retardant com ine or two or more of these compounds. position comprising a salt of components (A) and (B), 0003. The use of the combination of melamine conden wherein: sation products and phosphorus compounds in flame retar 0010 (A) is at least one alkylpyrophosphonic acid dant compositions is known, for example, from DE 601 11 derivative of the general formula (I): 720 T2. This reference describes, for example, salts of melamine condensation products with a phosphorus-con taining acid, the phosphorus-containing acid being an acid (I) having just one acid equivalent, and the melamine conden O O sation product being melam, for example. However, a dis O-P-O-P-O advantage with regard to these combinations is that they have a tendency to side reactions, for example at elevated R1 R2 temperatures. In particular, the phosphorus esters can lead to alkylation of the nitrogen component. 10011 where R' and R are each independently a substi 0004 WO 00/02869 A1 discloses polyphosphate salts of tuted or unsubstituted, straight-chain or branched alkyl 1.3.5-triazine compounds having a mean degree of conden group having 1 to 4 carbon atoms, Substituted or unsubsti sation (number-average) greater than 20 and a molar ratio of tuted benzyl or substituted or unsubstituted phenyl, and triazine compound, Such as of melamine, to phosphorus 0012 (B) is selected from the group consisting of (M/P) >1.1. This document additionally also describes a melamine, melam, melem, melon, ammeline, ammelide, two-stage process for preparing these salts by conversion of 2-ureidomelamine, Substituted or unsubstituted heptazine, a 1,3,5-triazine compound with orthophosphoric acid to the guanylurea, acetoguanamine, benZoguanamine and corresponding orthophosphate salt, and thermal treatment diaminophenyltriazine or two or more of these compounds. for conversion of the orthophosphate salt to a polyphosphate 0013. It is a feature of the above-defined flame retardant of the 1,3,5-triazine compound. In addition to the orthophos composition that the salt of components (A) and (B) present phates, it is also possible to use pyrophosphates. The poly therein has a high thermal stability up to 290° C., as a result phosphate salts described in this publication are appropri of which the flame retardant composition of the present ately to be used as flame retardants. However, phosphates or invention can be incorporated at high temperatures into polyphosphate are comparatively weak flame retardants and polymers such as polyamide, polybutyl terephthalate (PBT), are still unable to develop their flame retardancy particularly polystyrene (PS), high-impact polystyrene (HIPS) and acry at relatively low temperatures. lonitrile-butadiene-styrene (ABS) without breaking down. 0005 WO 96/09344 describes the use of melamine- or Further advantages are that the salt of components (A) and melem-phosphoric acid reaction products as flame retar (B) is hygroscopic only to a small degree, if at all. A further dants in glass fiber-reinforced polyamide molding com advantage lies in the processibility of the flame retardant pounds. Co-flame retardants used are Zinc borate, Zinc composition of the invention, for example with respect to the phosphate, etc. These flame retardants may still have almost compositions described in EP 0363 321 A1, since compo satisfactory flame retardancy in polyamides, but still do not sitions of this kind can release water and/or alcohols, for exhibit satisfactory efficacy in polyolefins in particular. example, on incorporation into the polymer and, in the case 0006 EP 1544206A1 describes dialkylphosphinic acids of use of an extruder in the incorporation into a polymer or and salts thereof, which are used together with further the processing of a polymer modified with the flame retar selected components as flame retardants in thermoplastic dant composition of the invention, leads to a relatively low polymers. According to this prior art, a particularly suitable level of deposits on the extruder screw. The monoesters combination is one of aluminum trisdiethylphosphinate, described in EP 0363 321 A1 can lead, for example, to melamine polyphosphate, Zinc oxide and glass fibers in alkylation reactions, which gives rise to odorous and in some US 2016/0281 001 A1 Sep. 29, 2016 cases toxic compounds. The components of the flame retar guanylurea, acetoguanamine, benZoguanamine and dant composition of the invention additionally have low diaminophenyltriazine or two or more thereof. water solubility, which means that they are leached out of 0021. In one embodiment of the invention, component the polymer to a Smaller degree on contact with water or (B) is a substituted or unsubstituted heptazine derivative of moisture. The polymers modified with the flame retardant the general formula (III): composition of the invention are therefore particularly suit able for agricultural films and moldings, housings or cables for moisture-prone rooms, washing machines and motor (III) vehicles. 0014. In a further embodiment of the invention, the above-defined flame retardant composition comprises, as a further component, component (C), one or more component (s) that act(s) synergistically with components (A) and (B). In this embodiment of the invention, this component (C) is a hindered amine compound sold under the FLAMESTABR) NOR 116 brand name by BASF SE. This flame retardant is disclosed in EP 0 889 085, the disclosure of which is included in the present application by reference. Alterna 0022. In this formula, Rare, for example, independently tively or additionally, component (C) is a polyI2,4-(piper H, or NH. Compounds of this kind are known to those azin-1,4-yl)-6-(morpholin-4-yl)-1,3,5-triazine, which is skilled in the art, for example from WO 2006/034784 A1 or also commercially available under the ppmTriazinr brand EP 2 256 122 A1, the disclosure of which is incorporated aC. here in full by reference. 0015 The proportion of this component (C), based on the 0023 Component (B), in a preferred embodiment of the Sum total of all components of the flame retardant compo invention, is melamine. sition, is generally in the range from 1% to 30% by weight, 0024 Salts preferred in accordance with the invention are preferably in the range from 5% to 25% by weight, more the melamine salt of pyromethylphosphonic acid or the preferably in the range from 10% to 20% by weight.
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