Compounds, polymers, compositions and uses thereof, methods for preparing the compounds, the polymers, and molding compounds, and molding compounds obtainable by the methods

Abstract

Disclosed are compounds, polymers, compositions and uses thereof, methods for preparing the compounds, the polymers, and molding compounds, and molding compounds obtainable by the methods.

Description

COMPOUNDS, POLYMERS, COMPOSITIONS AND USES THEREOF, METHODS FOR PREPARING THE COMPOUNDS, THE POLYMERS, AND MOLDING COMPOUNDS, AND MOLDING COMPOUNDS OBTAINABLE BY THE METHODSTECHNICAL FIELD

[0001] The present invention relates to flame retardant compounds and polymers. In particular, the invention concerns PNS compounds and polymers that can be used as flame retardants. Further, the invention relates to compositions comprising the compound and / or the polymer, flame-retardant plastics material compositions and molded parts produced therefrom.BACKGROUND

[0002] One topic that warrants attention is the hazards associated with plastic additives such as flame retardants within micro(nano)plastic as they can be persistent and can be biologically activated after entering the environment (J. Haz. Mat. 344 (2018) 179- 199).

[0003] In recent years, several plastic additives have been under scrutiny due to their potential ecotoxicity, bioaccumulation and tendency to act as endocrine disruptors. Concerns have been raised in the public domain on various flame retardants (The Danish Environmental Protection Agency. 2016:1-259). Toxicological and epidemiological studies have shown that several man-made brominated as well as aryl-, and halogenated organophosphorus flame retardants found in human blood serum, breastmilk and food may induce cytotoxic effects. Therefore, several brominated flame retardants have been or are being phased-out or have been added to the list of chemicals of high concern.

[0004] It must be underlined that plastic additives are intentionally added into the polymer and therefore we need to rethink and thoroughly assess what type of plastic additives can be introduced without an ecological risk. Conscientious producers of flame retarded plastic products have made major efforts to find alternative flame retardant solutions. Their aim is better overall environmental profiles and additives that exhibit higher efficacies at already low loadings of < 5%. This has stimulated the development of next generation flame retardants that can enhance the flame retardancy of polymers byscavenging free radicals mainly in the condensed phase by starving the flame zone of fuel and / or alternatively by enhancing the yield of polymer residue by crosslinking. In theory, radical generators may also exhibit gas-phase activity by scavenging the most active propagating free radicals (e.g., H , HO, etc.) that are responsible for the rapid reaction rates observed in flames (Polymer Green Flame Retardants 2014:267-288).

[0005] Already in the 1960's, radical generators were observed to boost the activity of brominated flame retardants by catalysing the formation of bromine radicals which then reacted with the hydrocarbon polymer to form HBr. The formed HBr molecule effectively interfered with the radical chain mechanism taking place in the gas phase whereby the flame is extinguished. Interest in organic radicals grew following Gomberg’s groundbreaking discovery in 1900 of the triphenylmethyl radical, the first stable carbonbased radical. Another clean way of generating carbon-centered radicals is by thermal decomposition of diazene compounds. The class of diazene and related compounds have proven to be effective as standalone flame retardants for polypropylene films at low loadings of 0.5-2 wt% (Macromolecular Rapid Communications 27(12), (2006), 976-981). Today, carbon-based radical generators such as dicumyl derivatives are typically used as synergists with brominated polymeric flame retardants for flame retarded expanded polystyrene (EPS) and / or extruded polystyrene (XPS). Recently, several other radical generator families have been successfully applied as flame retardants either alone or in combination with conventional flame retardants in various polymer types. For instance, N- alkoxyamine (WO 99 / 00450, WO 2008101845, WO2011086114) and sulfenamide (US 11 292968 B2) type of radical generators have been used as flame retardant synergists (WO2015 / 067736 Al). Alkoxyamines are known to thermally decompose to give aminyl / alkoxy and nitroxide / alkyl radicals pairs that exhibit fire proofing effect specially in thin section polypropylene films (EP 1379584). Oxyimides (US 10 913743) is another group of precursors of nitroxide and carbonyl radicals that has been found to exhibit fire proofing properties in thin polypropylene sections alone or in combination with phosphorous flame retardants in thick sections. Moreover, compounds containing sulfur such as sulfide and disulfides in various forms have also been used as adjuvants to promote the activity of phosphorous based flame retardants (Polym. Degrad. Stab. 110, (2014), 447- 456, Polym. Degrad. Stab. 129 (2016) 63-76).

[0006] Today, the styrene family of plastics encompasses a wide variety materials ranging from general purpose polystyrene (GPPS), to polystyrene foams through styrenecopolymers such as high impact polystyrene (HIPS), to various grades of styrene-butadiene (SB), styrene-acrylonitrile (SAN) to grades of acrylonitrile-butadiene-styrene (ABS) copolymers and all the way to blends of HIPS-polyphenylene oxide (PPO) and ABS with polycarbonates (PC). There are two main types of polystyrene insulating foams, i.e. EPS has a cellular structure containing voids or spacing in-between the cells and it may consist of up to 98% of air, whereas XPS is considered to have a closed-cell structure wherein the cells are packed together tightly and have no voids or spacing between them. EPS foam is widely used in building and construction materials, packing materials, medical appliances and automobile applications. The EPS is made by suspension polymerization of styrene in water in the presence of initiators, various suspension and blowing agents (e.g. pentane) to give polystyrene beads (Wunsch J. R. Polystyrene-Synthesis, Production and Applications, 1sted; Rapra Technology Limited: UK, 2000, and Brooks, B.W. Suspension polymerization processes. Chemical Engineering and Technology, 2010, 33, (11), 1737- 1744). In a subsequent process, the manufactured impregnated small polystyrene beads of ca. 1 mm in diameter are first pre-expanded at approximately 120 °C with steam and molded again with steam to produce large blocks that are cut into desired dimensions (Wypych, G. Handbook of Polymers, 2nd ed.; Chemical Technology Publishing: Canada, 2016). The production of XPS foam is carried out at approximately 180 - 200 °C on an extruding machine. In XPS, polystyrene is melted and after addition of e.g., carbon dioxide as foaming agent, the melt is extruded through a nozzle with a wide slit to obtain foamed insulation boards. Apart from the great deal of indisputable beneficial properties of foamed polystyrene such as high mechanical compression strength and dimensional stability, low thermal conductivity, lightweight, heat and cold resistance, water repellency, bacterial growth prevention and low thermal conductivity, EPS and XPS also has one major drawback of high flammability and its volatiles bum with massive soot formation with significant flaming dripping.

[0007] Hitherto, a series of strategies have been developed to decrease the flammability of foamed polystyrene. Aliphatic and cycloaliphatic brominated flame retardants releasing HBr into the vapor phase at moderate temperatures have been the predominating flame retardant grades of choice for both EPS and XPS. A brominated flame retardant may exhibit a dual flame retardant mechanism in polystyrene foams by rapid depolymerization of polystyrene by formed Br radicals. As of 1970s hexabromocyclododecane (HBCD) has been used as highly effective brominated flameretardant for both EPS and XPS. However, recent studies have shown that HBCD has a high tendency for bioaccumulation in the environment and therefore, as of 2015 the use of HBCD has been discontinued by European Chemical Agency (ECHA). Nowadays, the technical solution of replacing HBCD is to utilize polymeric brominated flame retardant such as brominated styrene-butadiene polymers with an improved environmental profile. The efficacy of the polymeric brominated flame retardant has further been enhanced by using synergists based on radical generators such as dicumyl peroxide or non-peroxides like dicumene, azo derivatives or 2,3-dimethyl-2,3-diphenyl butane. Furthermore, brominated flame retardants have successfully been used in combination with phosphorous based flame retardants such as triphenyl phosphate and different phosphates, phosphonates, phosphinates, phosphorous-nitrogen and phosphine sulfide compounds as well as expandable graphite in an effort to further reduce the bromine content.

[0008] Several attempts have been made to fully replace brominated flame retardants, however, developing such halogen-free flame retardants for polystyrene foam has failed. This is because alternative flame retardants need to meet several prerequisites besides high flame retardant efficacy, sustainability and low price, i.e., the requirements also extend to the type of polystyrene foam and at what stage the flame retardant can successfully be added. For EPS the most convenient and industrially viable method is to introduce the flame retardant before the start or in the early stages of suspension polymerization of styrene. However, many flame retardants may adversely impact the suspension polymerization process by causing suspension failure, by altering bead size distribution and subsequent expandability. In addition, flame retardants have a high tendency to decrease the molecular weight via chain transfer or termination reactions and increase the amount of residual monomer and thereby increase the concentration of volatile organic compounds (VOCs). Therefore, prior art examples of successful in-situ polymerization of halogen free flame retardants are very limited or prior art solutions would not be industrially viable.

[0009] The aforementioned flame retardants, known in the state of the art do not fulfill all / many requirements set forth for today's flame retardants. Thus, many of the flame retardants are polymer specific and they do not effectively flameproof different families of polymeric materials. Flame retardants based on radical generators mainly function only in thin films or fibers as standalone flame retardants and not in thick polymer sections, and relative high concentrations (10-60 %) are needed to meet different flameretardant standards, whereby e.g., mechanical properties of the plastic materials decrease significantly. Recyclability of polymeric materials containing the state of art flame retardants are in many cases problematic and they may form toxic gases in the case of fire and / or they may bioaccumulate in nature or otherwise having unfavorable tox profiles.

[0010] It is one of the aims of the present invention to eliminate at least a part of the problems relating to the art by providing new flame retardants.SUMMARY

[0011] This Summary is provided to introduce a selection of concepts in a simplified form that are further described below in the Detailed Description. This Summary is not intended to identify key features or essential features of the claimed subject matter, nor is it intended to be used to limit the scope of the claimed subject matter.

[0012] The invention is defined by the features of the independent claims. Some specific embodiments are defined in the dependent claims.

[0013] An object of the present invention is to provide a compound eliminating at least a part of the problems relating to the art.

[0014] The invention is based on the realization that compounds and polymers disclosed in the present disclosure may be used as flame retardants or as synergists with other conventional flame retardants. These new flame retardants that can flameproof a number of different polymeric materials and even flameproof thin, thick, and foamed polymeric materials. “Thin polymeric material” may be coatings and films that are 15-200 micrometer thick, whereas “thick polymeric material” may be thick sections that are 1 mm -25 cm thick. Furthermore, the new flame retardants can be used as standalone flame retardants at low loadings and as synergistic flame retardants components whereby the amount of conventional flame retardants may be significantly reduced. They can also provide a halogen free solution for flame retardancy.

[0015] According to a first aspect of the present invention, there is provided a compound of formula (I):formula (I), whereinR is selected from the group consisting of a Ci-20-alkyl, C2-2o-alkenyl, (CH2)m-Ce-2o- aryl, and a (CH2)m-Ci-2o-heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein m is an integer selected from 0- 2 and optionally the Ce-20-aryl and the Ci-20-heterocycle is substituted with 1-5 substituents each independently selected from R1; each R’ is independently selected from the group consisting of Ci-20-alkyl, C2-20- alkenyl, (CH2)n-Ce-20-aryl, SR, (CH2)n-C6-2o-arylene-C2-io-alkenyl, and a (CH2)n-Ci-2o- heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein n is an integer selected from 0-2 and optionally the Ce- 20-aryl and the (CH2)n-Ci-2o-heterocycle is substituted with 1-5 substituents each independently selected from R2;X is selected from the group consisting of a bond, NR’, N(R’)(R10), O, OR10, and R10, each optionally substituted with 1-5 substituents each independently selected from R3;X’ is selected from the group consisting of a bond, NR’, N(R’)(R10), O, OR10, and R10, each optionally substituted with 1-5 substituents each independently selected from R4;R” is selected from the group consisting of Ci-20-alkyl, (CH2)o-Ce-20-aryl, and SR, wherein o is an integer selected from 0-2 and optionally the Ci-20-alkyl and the (CH2)0-Ce- 20-aryl is substituted with 1-5 substituents each independently selected from R5;R’” is selected from the group consisting of Ci-20-alkyl, (CH2)P-Ce-2o-aryl, and SR, wherein p is an integer selected from 0-2 and optionally the Ci-20-alkyl and the (CH2)P-Ce- 20-aryl is substituted with 1-5 substituents each independently selected from R6; orR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle optionally substituted with 1-5 substituents each independently selected from R1; and each R1, R2, R3, R4, R5, and R6is independently selected from the group consisting of Ci-10-alkyl, C2-io-alkenyl, (CH2)q-02C-C2-io-alkenyl, oxiran-2-yl, (CH2)q-SR7, (CH2)q- OR7, (CH2)q-N(R7)2, OP(O)(OR8)2 and -PO(R8)2, wherein q is an integer selected from 0-2, each R7is independently selected from the group consisting of H, Ci-10-alkyl, and C2-10- alkenyl, and each R8is independently selected from the group consisting of Cuio-alkyl,C2-io-alkenyl, Ce-20-aryl, and OR9, wherein R9is selected from the group consisting of Ci-io-alkyl, C2-io-alkenyl, and Ce-20-aryl; and each R10is independently selected from the group consisting of a linear or branched Ci-6-alkylene, cyclic C3-io-alkylene, Ce-20-arylene, C?-24-alkarylene, and C?-24-arylalkylene.

[0016] According to a second aspect of the present invention, there is provided a polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in the present disclosure, wherein the moiety is included in a main chain of the polymer, in a pendant group of the polymer or is part of a crosslink of the polymer.

[0017] According to a third aspect of the present invention, there is provided a composition comprising a compound of formula (I) and / or a polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in the present disclosure.

[0018] According to a fourth aspect of the present invention, there is provided a use of a compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in the present disclosure as a flame retardant or as a synergist with one or more flame retardants.

[0019] According to a fifth aspect of the present invention, there is provided a method for producing molding compounds, wherein the method comprises: a) providing a melt composition comprising a polymer melt comprising at least one compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in the present disclosure, preferably the melt composition further comprises an organic blowing agent, wherein the temperature of the melt composition is at least 120 °C; b) discharging the melt composition through a nozzle plate having one or more holes; and c) granulating the discharged melt composition.

[0020] According to a sixth aspect of the present invention, there is provided a method for producing molding compounds, wherein the method comprises: a) polymerizing a first composition comprising a compound of formula (I) or a polymer comprising one or more repeating units and a moiety of a compound offormula (I) as defined in the present disclosure, optionally in the presence of one or more vinylic monomers, to form a first polymer; b) optionally adding before, during, and / or after the polymerizing in a) one or more of an organic blowing agent, suspension agent, and nucleating agent, or a combination thereof to the first composition or to the formed first polymer; and c) separating the formed first polymer.

[0021] According to a seventh aspect of the present invention, there is provided a molding compound obtainable by a method as defined in the present disclosure.

[0022] According to an eight aspect of the present invention, there is provided a use of compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in the present disclosure as an individual component or co-component of insulating material for buildings or as a part and / or component in electrical devices, or in polymer extrusion or in polymerization processes.

[0023] According to an eight aspect of the present invention, there is provided a method for the preparation of a compound of formula (I) as defined in the present disclosure, wherein the method comprises i) providing a reaction composition comprising a compound of formula (X):formula (X), whereinX, X’, R’, R”, and R’” are as defined in the present disclosure; and a base, thereby deprotonating the nitrogen of the compound of formula (X); ii) optionally heating the reaction composition; iii) adding to the reaction composition a compound of formula (XII):R-S-X’” formula (XII), whereinR is as defined in the present disclosure; andX’” is a leaving group, thereby forming a compound of formula (I):formula (I), whereinX, X’, R, R’, R”, and R”’ are as defined in the present disclosure.

[0024] According to a ninth aspect of the present invention, there is provided a method for the preparation of a polymer comprising one or more repeating units and a moiety of a compound of formula (I), as defined in the present disclosure, wherein the method comprises: i) providing a reaction composition comprising a compound of formula (I):formula (I), whereinX, X’, R, R’, R”, and R”’ are as defined in the present disclosure; and optionally one or more monomers; ii) optionally heating the reaction composition, thereby forming the polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in the present disclosure.DETAILED DESCRIPTION

[0025] The following explanations of terms and methods are provided to better describe the present compounds, compositions, polymers and methods, and to guide those of ordinary skill in the art in the practice of the present disclosure. It is also to be understood that the terminology used in the disclosure is for the purpose of describing particular embodiments and examples only and is not intended to be limiting.

[0026] An objective of the present invention is to provide high-effective halogen free flame retardant for polymeric materials at low loadings as standalone flame retardants or as a synergist with other conventional flame retardants such as phosphorous based flame retardants, metal hydrates (e.g. Al(OH)s, Mg(OH)2, etc.), fillers (including nano fillers),intumescent flame retardants, melamine cyanurate, zinc based flame retardants and halogenated flame retardants.

[0027] By using the inventive flame retardants as synergists, the loading of the conventional flame retardant may be used in substantially reduced amounts.

[0028] Furthermore, an objective of the invention is to provide a method for preparing flame retarded foamed polystyrene by suspension polymerization of styrene in the presence of a blowing agent and the inventive flame retardants. The invention provides a method for preparing flame retarded foamed polystyrene (EPS), that may avoid at least partially the above-mentioned technical problems of suspension failure, decrease of molecular weight of polystyrene, alteration of bead size and its distribution and / or decrease in mechanical properties. Noteworthy, a flameproofed foamed polystyrene can also be prepared by utilizing the inventive flame retardants in an extrusion process.

[0029] It is to be understood that the embodiments of the invention disclosed are not limited to the particular structures, process steps, or materials disclosed herein, but are extended to equivalents thereof as would be recognized by those ordinarily skilled in the relevant arts. It should also be understood that terminology employed herein is used for the purpose of describing particular embodiments only and is not intended to be limiting.

[0030] Reference throughout this specification to “one embodiment” or “an embodiment” means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment of the present invention. Thus, appearances of the phrases “in one embodiment” or “in an embodiment” in various places throughout this specification are not necessarily all referring to the same embodiment.

[0031] As used herein, a plurality of items, structural elements, compositional elements, and / or materials may be presented in a common list for convenience. However, these lists should be construed as though each member of the list is individually identified as a separate and unique member. Thus, no individual member of such list should be construed as a de facto equivalent of any other member of the same list solely based on their presentation in a common group without indications to the contrary. In addition, various embodiments and example of the present invention may be referred to herein along with alternatives for the various components thereof. It is understood that suchembodiments, examples, and alternatives are not to be construed as de facto equivalents of one another, but are to be considered as separate and autonomous representations of the present invention.

[0032] Furthermore, the described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided, such as examples of lengths, widths, shapes, etc., to provide a thorough understanding of embodiments of the invention. One skilled in the relevant art will recognize, however, that the invention can be practiced without one or more of the specific details, or with other methods, components, materials, etc. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring aspects of the invention.

[0033] “Optional” or “optionally” denotes that the subsequently described event or circumstance may but need not occur, and that the description includes instances where the event or circumstance occurs and instances in which it does not.

[0034] The verbs “to comprise” and “to include” are used in this document as open limitations that neither exclude nor require the existence of also un-recited features. “Comprises” or “comprising” denotes that the subsequently described feature(s) or act(s) may but need not include other feature(s) or act(s). The features recited in depending claims are mutually freely combinable unless otherwise explicitly stated. Furthermore, it is to be understood that the use of "a" or "an", i.e., a singular form, throughout this document does not exclude a plurality.

[0035] In one aspect is provided a compound of formula (I):formula (I), whereinR is selected from the group consisting of a Ci-20-alkyl, C2-2o-alkenyl, (CH2)m-Ce-2o- aryl, and a (CH2)m-Ci-2o-heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein m is an integer selected from 0-2 and optionally the Ce-20-aryl and the Ci-20-heterocycle is substituted with 1-5 substituents each independently selected from R1; each R’ is independently selected from the group consisting of Ci-20-alkyl, C2-20- alkenyl, (CH2)n-Ce-20-aryl, SR, (CH2)n-C6-2o-arylene-C2-io-alkenyl, and a (CH2)n-Ci-2o- heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein n is an integer selected from 0-2 and optionally the Ce- 20-aryl and the (CH2)n-Ci-2o-heterocycle is substituted with 1-5 substituents each independently selected from R2;X is selected from the group consisting of a bond, NR’, N(R’)(R10), O, OR10, and R10, each optionally substituted with 1-5 substituents each independently selected from R3;X’ is selected from the group consisting of a bond, NR’, N(R’)(R10), O, OR10, and R10, each optionally substituted with 1-5 substituents each independently selected from R4;R” is selected from the group consisting of Ci-20-alkyl, (CH2)o-Ce-20-aryl, and SR, wherein o is an integer selected from 0-2 and optionally the Ci-20-alkyl and the (CH2)0-Ce- 20-aryl is substituted with 1-5 substituents each independently selected from R5;R’” is selected from the group consisting of Ci-20-alkyl, (CH2)P-Ce-2o-aryl, and SR, wherein p is an integer selected from 0-2 and optionally the Ci-20-alkyl and the (CH2)P-Ce- 20-aryl is substituted with 1-5 substituents each independently selected from R6; orR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle optionally substituted with 1-5 substituents each independently selected from R1; and each R1, R2, R3, R4, R5, and R6is independently selected from the group consisting of Ci-10-alkyl, C2-io-alkenyl, (CH2)q-02C-C2-io-alkenyl, oxiran-2-yl, (CH2)q-SR7, (CH2)q- OR7, (CH2)q-N(R7)2, OP(O)(OR8)2 and -PO(R8)2, wherein q is an integer selected from 0-2, each R7is independently selected from the group consisting of H, Ci-10-alkyl, and C2-10- alkenyl, and each R8is independently selected from the group consisting of Ci-io-alkyl, C2-io-alkenyl, Ce-20-aryl, and OR9, wherein R9is selected from the group consisting of Ci-io-alkyl, C2-io-alkenyl, and Ce-20-aryl; and each R10is independently selected from the group consisting of a linear or branched Ci-6-alkylene, cyclic C3-io-alkylene, Ce-20-arylene, C?-24-alkarylene, and C?-24-arylalkylene.

[0036] The term “aliphatic” is defined as including alkyl, alkenyl, alkynyl, halogenated alkyl and cycloalkyl groups.

[0037] The term “alkyl” refers to a branched or unbranched saturated hydrocarbon group of 1 to 20 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, / -butyl, pentyl, hexyl, heptyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl and the like. Preferred alkyl groups have 1 to 10 carbon atoms. Alkyl groups may be “substituted alkyls” wherein one or more hydrogen atoms are substituted with a substituent such as halogen, cycloalkyl, alkoxy, amino, hydroxyl, aryl, alkenyl, or carboxyl. For example, a Ci-8-alkyl (i.e., a (Ci-C8)alkyl) can be, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, pentyl, 3-pentyl, or hexyl; Ch-e-cycloalkyl can be cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; C3-6-cycloalkyl-Ci-8-alkyl can be cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 2- cyclopropylethyl, 2-cyclobutylethyl, 2-cyclopentylethyl, or 2-cyclohexylethyl; Ci-8-alkoxy can be methoxy, ethoxy, propoxy, isopropoxy, butoxy, iso-butoxy, sec-butoxy, pentoxy, 3- pentoxy, or hexyloxy; C2-8-alkenyl can be vinyl, allyl, 1 -propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -pentenyl, 2-pentenyl, 3 -pentenyl, 4-pentenyl, 1- hexenyl, 2- hexenyl, 3 -hexenyl, 4-hexenyl, or 5 -hexenyl; C2-8-alkynyl can be ethynyl, 1-propynyl, 2- propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1 -pentynyl, 2-pentynyl, 3 -pentynyl, 4-pentynyl, 1- hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, or 5-hexynyl; (Ci-C8)alkanoyl can be acetyl, propanoyl or butanoyl; halo(Ci-C8)alkyl can be iodomethyl, bromomethyl, chloromethyl, fluoromethyl, trifluoromethyl, 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, or pentafluoroethyl; hydroxy(Ci-C8)alkyl can be hydroxymethyl, 1 -hydroxy ethyl, 2- hydroxy ethyl, 1 -hydroxypropyl, 2-hydroxypropyl, 3 -hydroxypropyl, 1 -hydroxybutyl, 4- hydroxybutyl, 1 -hydroxypentyl, 5 -hydroxypentyl, 1 -hydroxyhexyl, or 6-hydroxyhexyl; (Ci-C8)alkoxycarbonyl can be methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, or hexyloxycarbonyl; (Ci- C8)alkylthio can be methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, or hexylthio; (C2-Ce)alkanoyloxy can be acetoxy, propanoyloxy, butanoyloxy, isobutanoyloxy, pentanoyloxy, or hexanoyloxy. Examples of “Cns-alkyl derivatives thereof being substituted with one or more halogen” include, but are not limited to, trifluoromethyl.

[0038] “Alkenyl” refers to a cyclic, branched or straight chain group containing only carbon and hydrogen, and contains one or more double bonds that may or may not be conjugated. Alkenyl groups may be unsubstituted or substituted.

[0039] “Alkanediyl” and “alkylene”, “cycloalkanediyl” and “cyclic alkylene”, “aryldiyl” and “arylene”, and “alkanearyldiyl” and “alkarylene” and “arylalkylene” refer to bivalent radicals derived from aliphatic, cycloaliphatic, aryl, and alkanearyl and arylalkyl hydrocarbons.

[0040] The term “alkoxy” refers to a straight, branched or cyclic hydrocarbon configuration and combinations thereof, including from 1 to 20 carbon atoms, preferably from 1 to 8 carbon atoms (referred to as a “lower alkoxy”), more preferably from 1 to 4 carbon atoms, that include an oxygen atom at the point of attachment. An example of an “alkoxy group” is represented by the formula -OR, where R can be an alkyl group, optionally substituted with an alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, halogenated alkyl, alkoxy or heterocycloalkyl group. Examples of alkoxy groups and lower alkoxy and Ci-8- alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i- butoxy, sec-butoxy, tert-butoxy, cyclopropoxy, cyclohexyloxy, and the like.

[0041] “Alkynyl” refers to a cyclic, branched or straight chain group containing only carbon and hydrogen, and unless otherwise mentioned typically contains one to twelve carbon atoms, and contains one or more triple bonds. Alkynyl groups may be unsubstituted or substituted.

[0042] An “analog” is a molecule that differs in chemical structure from a parent compound, for example a homolog (differing by an increment in the chemical structure or mass, such as a difference in the length of an alkyl chain or the inclusion of one of more isotopes), a molecular fragment, a structure that differs by one or more functional groups, or a change in ionization. An analog is not necessarily synthesized from the parent compound. A “derivative” is a molecule derived from the base structure.

[0043] The term "aralkyl" refers to an alkyl group wherein an aryl group is substituted for a hydrogen of the alkyl group. An example of an aralkyl group is a benzyl group.

[0044] “Aryl” and “aromatic ring” refer to a monovalent or polyvalent unsaturated aromatic carbocyclic group having a single ring (e.g., phenyl) or multiple condensed rings (e.g., naphthyl or anthryl), which can optionally be unsubstituted or substituted. Examples of “Ce io-aryl” or “6-10 membered aromatic ring” include, but are not limited to, phenyl, indanyl, and naphthyl. A “heteroaryl” and a “heteroaryl group” is defined as an aromaticgroup that has at least one heteroatom incorporated within the ring of the aromatic group. Therefore, it is to be understood that an “aromatic ring comprising 0-5 heteroatoms” may be an aryl or an heteroaryl. It is also to be understood that the terms “heterocyclic ring” as used in the present disclosure may include both aromatic and non-aromatic monovalent and polyvalent radicals derived from heterocyclic compounds and, therefore, may be a heteroaryl (such as, but not limited to, pyridinyl and indolyl) or a heterocyclic ring (such as, but not limited to, imidazolidinyl). Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorous. Heteroaryl includes, but is not limited to, pyridinyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isooxazolyl, thiadiazolyl, oxadiazolyl, thiophenyl, furanyl, quinolinyl, isoquinolinyl, benzimidazolyl, benzooxazolyl, quinoxalinyl, and the like. The aryl or heteroaryl group can be substituted with one or more substituents including, but not limited to, alkyl, alkynyl, alkenyl, aryl, halide, nitro, amino, ester, ketone, aldehyde, hydroxy, carboxylic acid, thiol, thioalkyl, or alkoxy, or the aryl or heteroaryl group can be unsubstituted.

[0045] The terms “cycloalkyl” and “aliphatic ring” refer to a non-aromatic carbonbased ring composed of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo[2.2.1]heptanyl, and the like. The terms “heterocycloalkyl group”, “heterocyclic ring” and “heterocycle” is a cycloalkyl group as defined above where at least one of the carbon atoms of the ring is substituted with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorous. Therefore, the terms “aliphatic ring comprising 0-5 heteroatoms” as used herein and hereafter may include both cycloalkyls and heterocycloalkyl groups (heterocyclic rings, heterocycles), and may be a monovalent or polyvalent saturated or partially unsaturated aliphatic ring having a single ring (e.g., cyclohexyl) or multiple condensed rings (e.g., perhydronaphth-2-yl). Therefore, “C1-20- heterocycle” may be for example, but not limited to, a mono- or divalent oxirane (e.g., 2- oxiranyl if monovalent and 2, 3 -oxiranediyl if divalent) if comprising two carbon atoms and one oxygen as the heteroatom. Further, the terms “heterocyclic”, “heterocycle” and “heterocyclic ring” refer to a closed-ring compound, or radical thereof as a substituent bonded to another group, particularly other organic groups, where at least one atom in the ring structure is other than carbon, and typically is oxygen, sulfur, nitrogen and / or phosphorous. It is to be understood that the terms “heterocyclic ring”, “heterocyclic”, and“heterocycle” as used in the present disclosure may include both aromatic and nonaromatic monovalent and polyvalent radicals derived from heterocyclic compounds and, therefore, may refer to a heteroaryl group, a non-aromatic heterocycloalkyl group and heterocyclic ring. A “Ci-20-heterocycle comprising 1-5 heteroatoms” and a “5-10 membered heterocyclic ring” may have a single ring (e.g., pyridinyl) or multiple, e.g., two, three, or four, condensed rings (e.g., indolyl).

[0046] The terms “mono- or polycyclic heterocycle” refer to monovalent or polyvalent heterocycles having a single heterocyclic ring (monocyclic) or multiple rings (polycyclic, e.g., di- and tricyclic) provided that at least one of the rings of the multiple rings is a heterocyclic ring. The mono- and polycyclic heterocycle can be unsubstituted or substituted. Examples of mono- and polycyclic heterocycles include, but are not limited to, 2-oxo- 1 ,2X5-oxaphosph i nan-2-y I , 1 -oxo-3 ,4-dihydro-2, 1 X5-benzoxaphosphinin- 1 -yl, and 10-oxo-9-oxa-l OX5-phospha- 10-phenanthryl. Therefore, it is to be understood that “R”’, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle“ may refer to, but not limited to, a 2-oxo-l ,2X5-oxaphosphinan-2-yl, 1 -oxo-3, 4-dihydro-2,lX5-benzoxaphosphinin-l-yl, and 10-oxo-9-oxa-l OX5-phospha- 10- phenanthryl.

[0047] In the present context, the terms “substituted” or “substitution” refer to replacement of a hydrogen atom of a molecule, a group or moiety with one or more substituents. Unless otherwise defined, the term “optionally-substituted” or “optional substituent” as used herein refers to a group which may or may not be further substituted with 1, 2, 3, 4, 5 or more groups, preferably 1, 2, 3, 4 or 5, more preferably 1 or 2 groups. The substituents may be selected, for example, from Ci-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-8-cycloalkyl, hydroxyl, oxo, Ci-6-alkoxy, aryloxy, Ci-6-alkoxyaryl, halo, Ci-6-alkylhalo (such as CF3 and CHF2), Ci-6-alkoxyhalo (such as OCF3 and OCHF2), carboxyl, esters, cyano, nitro, amino, substituted amino, disubstituted amino, acyl, ketones, amides, aminoacyl, substituted amides, disubstituted amides, thiol, alkylthio, thioxo, sulfates, sulfonates, sulfinyl, substituted sulfinyl, sulfonyl, substituted sulfonyl, sulfonylamides, substituted sulfonamides, disubstituted sulfonamides, aryl, Ci-6-alkyl, heterocyclyl and heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl and heterocyclyl and groups containing them may be further optionally substituted. Optional substituents in the case N-heterocycles may also include but are not limited to Ci-6-alkyl, i.e., X-Ci-3-alkyl, more preferably methyl, particularly A -mcthyl.

[0048] In one aspect is provided a polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in the present disclosure, wherein the moiety is included in a main chain of the polymer, in a pendant group of the polymer or is part of a crosslink of the polymer. Additionally, or alternatively, the formula (I):formula (I), whereinR’”, X’, X, R”, R’ and R are as defined in the present disclosure. Additionally, or alternatively, the moiety is a mono- or polyvalent, preferably a mono- or bivalent, group of the compound of formula (I).

[0049] Alternatively, provided is a polymer of one or more monomers, wherein at least one of the monomers has formula (I):formula (I), whereinR” ’, X’, X, R”, R’ and R are as defined in the present disclosure.

[0050] Additionally, or alternatively, the polymer is a polymer of one monomer, wherein the monomer has formula (I):formula (I), whereinR” ’, X’, X, R”, R’ and R are as defined in the present disclosure.

[0051] Additionally, or alternatively, the polymer is a copolymer of two or more monomers, preferably two monomers, wherein one of the two or more monomers has formula (I):formula (I), whereinR” ’, X’, X, R”, R’ and R are as defined in the present disclosure; and one of the two or more monomers is selected from styrene, acrylates, such as alkyl acrylates, such as methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, and lauryl acrylate; and vinyl acetate, preferably selected from styrene.

[0052] Additionally, or alternatively, the polymer is a copolymer of two or more monomers, preferably two monomers, wherein one of the two or more monomers has formula (I):formula (I), whereinR” ’, X’, X, R”, R’ and R are as defined in the present disclosure; and one of the two or more monomers is styrene.

[0053] Additionally, or alternatively, the moiety of the compound of formula (I) is one of the one or more repeating units.

[0054] Additionally, or alternatively, R is l,3-benzothiazol-2-yl; R’ is (p- styrenyl)methyl; and R ', X', R ", X, and the phosphorous both X' and X are attached to, together with the oxo attached to said phosphorous, together form a 10-oxo-9-oxa-10X5- phospha- 10 -phenanthryl.

[0055] Additionally, or alternatively, R is l,3-benzothiazol-2-yl; R’ is 2-(p- methylylphenyl)ethyl; and R ', X', R ", X, and the phosphorous both X' and X are attached to, together with the oxo attached to said phosphorous, together form a 10-oxo-9- oxa-1 OX5-phospha- 10-phenanthryl. This moiety of the compound of formula (I) may be included in a main chain of the polymer, in a pendant group of the polymer or is part of a crosslink of the polymer. It is to be understood that R’ is a bivalent group that is attached to N of the compound of formula (I) (to which also the phosphorous and S are attached to)but R’ is also attached to the main chain of the polymer, in a pendant group of the polymer or is part of a crosslink of the polymer.

[0056] Additionally, or alternatively, R is l,3-benzothiazol-2-yl; R’ is l-(p- methylylphenyl)ethylene; and R ', X', R ", X, and the phosphorous both X' and X are attached to, together with the oxo attached to said phosphorous, together form a 10-oxo-9- oxa-1 OX5-phospha- 10-phenanthryl. This moiety of the compound of formula (I) may be included in a main chain of the polymer, in a pendant group of the polymer or is part of a crosslink of the polymer. It is to be understood that R’ is a trivalent group that is attached to N of the compound of formula (I) (to which also the phosphorous and S are attached to) but R’ is also attached to the main chain of the polymer, in a pendant group of the polymer or is part of a crosslink of the polymer. Therefore, this moiety of the compound of formula (I) may be a repeating unit of the polymer.

[0057] The term “polymer” as used herein and hereafter refers to natural and / or synthetic linear or two- or three-dimensional homopolymers and copolymers that can be unbranched or branched polymers, such as, but not limited to, star polymers, comb polymers, brush polymers, dendronized polymers, ladder polymers, and dendrimers. Polymers which contain only a single type of repeating unit are referred as homopolymers, while polymers containing two or more types of repeating units are referred as copolymers.

[0058] The term “copolymer” as used herein and hereafter refers to polymers derived from more than one species of monomer. Copolymers include, but are not limited to, alternating copolymers, periodic copolymers, statistical copolymers, random copolymers, block copolymers, and graft copolymers.

[0059] The term “monomer” as used herein and hereafter refers to a molecule that can undergo polymerization thereby contributing repeating units to the essential structure of a polymer. The monomers are used to form the one or more repeating units of the polymer. Monomers include, but are not limited to, compounds of formula (I) as disclosed in the present disclosure that are polymerizable, e.g., having a double bond or an epoxy group, styrene, cyclic lactones, carbonates, esters, lactams, alkenes, and epoxides. Examples of preferred monomers are styrene and compound 8 as disclosed in the present disclosure.

[0060] The term “repeating unit” as used herein and hereafter refers to a part of the main chain (backbone) of a polymer that is connected on at least two ends to the polymer chain. I.e., the repeating unit is a part of a polymer whose repetition would produce the complete polymer chain (except for the end-groups) by linking the repeat units together successively along the chain. Furthermore, a repeating unit is a basic structural unit of a polymer, said repeating unit corresponds to a monomer unit, which has been polymerized to produce a polymer.

[0061] The terms “end group” as used herein and hereafter refers to functionalities and constitutional units that are at the extremity of polymers, in particular copolymers.

[0062] The terms “constitutional units” as used herein and hereafter refers to a group of atoms comprising a part of the essential structure of polymers, in particular copolymers. Constitutional units may be covalently attached between repeating units. Constitutional units covalently attached at the extremity of polymers are referred herein and hereafter to end groups.

[0063] Additionally, or alternatively, R is a Ci-20-heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein optionally the Ci-20-heterocycle is substituted with 1-5 substituents each independently selected from R1.

[0064] Additionally, or alternatively, R is a (CH2)m-C6-2o-aryl; and m is 0; optionally wherein the Ce-20-aryl is substituted with 1-5 substituents each independently selected from R1.

[0065] Additionally, or alternatively, R is a (CH2)m-C6-2o-aryl; and m is 1 ; optionally wherein the Ce-20-aryl is substituted with 1-5 substituents each independently selected from R1.

[0066] Additionally, or alternatively, R’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle optionally substituted with 1-5 substituents each independently selected from R1.

[0067] Additionally, or alternatively, R’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle comprising a phosphorous and 0-3 heteroatoms each independently selected from the group consistingof N, O, and S, optionally wherein the heterocycle is substituted with 1-5 substituents each independently selected from R1.

[0068] Additionally, or alternatively, X is O; andR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a 5 - 14 membered mono-, bi- or tricyclic heterocycle comprising a phosphorus and an oxygen, optionally wherein the mono-, bi- or tricyclic heterocycle is substituted with 1-5 substituents each independently selected from R1.

[0069] Additionally, or alternatively, X is O; andR ', X', R ", X, and the phosphorous both X' and X are attached to together form a 14 membered tricyclic heterocycle comprising a phosphorus and an oxygen, optionally wherein the tricyclic heterocycle is substituted with 1-5 substituents each independently selected from R1.

[0070] Additionally, or alternatively, X is O; andR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle selected fromwherein the heterocycle being optionally substituted with 1-5 substituents each independently selected from R1. It is to be understood that the wavy bonds indicate the attachments of the phosphorous to the oxo and the N that the phosphorous is attached to in formula (I).

[0071] Additionally, or alternatively, each R’ is independently selected from the group consisting of Ci-6-alkyl, C2-6-alkenyl, (CH2)n-Ce-io-aryl, SR, and (CH2)n-Ce-io- arylene-C2-4-alkenyl, wherein n is an integer selected from 0-1 and optionally the Ce-io- aryl is substituted with 1 substituent selected from R2; andR2is selected from CH=CH2, (CH2)-O2C-CH=CH2, and oxiran-2-yl, preferably the 1 substituent is para to the nitrogen that the phenyl or benzyl is attached to.

[0072] Additionally, or alternatively, each R’ is independently selected from the group consisting of tert-butyl, phenyl, and benzyl, optionally wherein the phenyl andbenzyl is substituted with 1-3 substituents, preferably 1 substituent, each independently selected from R2; andR2is selected from CH=CH2, (CH2)-O2C-CH=CH2, and oxiran-2-yl, preferably the 1 substituent is para to the nitrogen that the phenyl or benzyl is attached to.

[0073] Additionally, or alternatively, both X and X’ are O; and both R” and R”’ are selected from ethyl and phenyl; orR” ’, X’, R”, X, and the phosphorous both X’ and X are attached to together form a

[0074] Additionally, or alternatively, the compound of formula (I) is selected from a compound of formula (la), (formula (lb) formula (Ic) formula (Id)formula (I e) formula (If) formula (Ig) formula (Ih) formula (li)

[0075] Additionally, or alternatively, the polymer is a polymer of one or more monomers, wherein at least one of the one or more monomers is a compound of formula (la), (lb), (Ic), (Id), (le), (If), (Ig), (Ih), or (li), preferably at least one of the one or more monomers has formula (le):formula (le)

[0076] Additionally, or alternatively, the polymer is a copolymer or a terpolymer.

[0077] The terms “molecular weight” (Mw) as used herein and hereafter refers to the molecular mass and is expressed in g / mol. “Molecular weight” may also refer to the number average molecular weight (also called the number average molar mass, Mn), which is the average of the molecular masses of the individual macromolecules, in particular polymers.

[0078] The term “wt-%” or “wt%” as used herein and hereafter refers to percentage by mass, i.e., the mass fraction (wi) of the mass (mi) to the total mass (mtot) times a denominator of 100, i.e., the formula wt-% = Wi * 100 = (mi / mtot) * 100, wherein Wi = mass fraction of compound or polymer to which wt-% refers to, m; = mass of compound or polymer to which wt-% refers to, and mtot = the total mass of e.g. starting material, product, or composition, or to what it refers to. It is to be understood that the proportion (wt-%) of each compound in any of the compositions as disclosed herein and herefater may be selected so that they add up to 100 wt-%.

[0079] The term “moiety” as used herein and hereafter refers to mono- or bivalent group of a molecule (compound) that is typically attached, typically covalently attached, to at least one organic compound and / or polymer. In the context of “moiety of a compound of formula (I)”, the term “moiety” refers to a part of the compound of formula (I), i.e., a replacement of one or more hydrogen atoms of the compound of formula (I) with the at least one organic compound and / or polymer (being then mono- or polyvalent) that the moiety is attached to. Therefore, it is to be understood that the moiety of the compound of formula (I), wherein R’”, X’, X, R”, R’ and R are as defined in the present disclosure, at least one of R’”, X’, X, R”, R’ and R, preferably one of R, R’, R” or R’”, is in fact a bi-or polyvalent group, which is also attached to the main chain of the polymer, to a pendant group of the polymer or is part of a crosslink of the polymer. Therefore, it is to be understood that even though one of R’”, X’, X, R”, R’ and R may be defined in the present disclosure as, e.g., a monovalent group (such as an alkyl group), in the context of the moiety said R’”, X’, X, R”, R’ and R group has a greater valence, i.e., said group is capable also to attach to the main chain of the polymer, to a pendant group of the polymer or a part of a crosslink of the polymer. Therefore, said monovalent group (alkyl group) is in the context of the moiety an alkanediyl (alkylene) group. An example of a moiety of a compound of formula (I), but is not limited to this example, is:The wavy bonds indicate the attachment to the polymer. As can be seen from the above structure, this is a moiety of compound 8 (described elsewhere in this disclosure), wherein the moiety is divalent (position of attachment indicated by the two wavy bonds). Therefore, even though R’ of the compound of formula (I) is (4-vinylphenyl)methyl (( / ?- styrenyl)methyl) in this case, the moiety derived from this compound is a 1 -( / ?- methylylphenyl)ethylene (l-(4-methylylphenyl)ethylene) group at the corresponding R’ position. Further, as can be seen from the above structure, two hydrogens of the compound 8 have been substituted such that this moiety may in fact be one of the one or more repeating units. This is shown in the below structure:Therefore, an example of a polymer, in particular a copolymer, comprising two repeating units, wherein at least one of the repeating units is a moiety of a compound of formula (I), is:As can be seen from the above structure, the polymer is a copolymer of two repeating units, wherein one of the two repeating units is a moiety of a compound of formula (I), and one of the two repeating units is derived from styrene.

[0080] Additionally, or alternatively, the polymer is a copolymer comprising or consisting of two repeating units, wherein one of the two repeating units is a moiety of a compound of formula (I), and one of the two repeating units is derived from styrene.

[0081] In one aspect is provided a composition comprising a compound of formula (I) and / or a polymer comprising one or more repeating units and a moiety of a compound of formula (II) as defined in the present disclosure.

[0082] Additionally, or alternatively, the composition further comprises a polymeric substrate.

[0083] Additionally, or alternatively, the composition comprises the compound of formula (I), or the polymer comprising one or more repeating units and a moiety of a compound of formula (I), as defined in the present disclosure and a polymeric substrate.

[0084] The polymeric substrate may be flame retarded by utilizing the present inventive flame retardants. It should be understood that terms “polymeric substrate” and “polymer substrate” is used in the present disclosure interchangeable. Examples of suitable polymer substrates include, but are not limited to, natural and / or synthetic polymers, such as:

[0085] 1) polymers of mono- and diolefins, for example, but not limited to, poly-propylene, polyisobutylene, polybutene- 1, poly-4-methyl-pentene-l, polyvinylcyclohexane, polyisoprene or polybutadiene and also polymerizates of cycloolefins, for example of cyclopentene or norbomene; and also polyethylene (which may optionally be crosslinked), for example, but not limited to, high density poly-ethylene (HDPE), high density polyethylene of high molecular weight (HDPE-HMW), high density polyethylene of ultra-high molecular weight (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), and linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE), or mixtures thereof;

[0086] 2) examples of mixtures mentioned in 1) include, but are not limited to, polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP / HDPE, PP / LDPE) and mixtures of different types of polyethylene (for example LDPE / HDPE);

[0087] 3) copolymers of mono- and diolefins with one another or with other vinyl monomers, for example, but not limited to, ethylene / propylene copolymers, linear low density polyethylene (LL-DPE) and mixtures thereof with low density polyethylene (LDPE), propylene / butene-1 copolymers, propylene / isobutylene copolymers, ethylene / butene-1 copolymers, ethylene / hexene copolymers, ethylene / methylpentene copolymers, ethylene / heptene copolymers, ethylene / octene copolymers, ethylene / vinylcyclohexane copolymers, ethyl-ene / cycloolefin copolymers, for example ethylene / norbomene (COC), ethylene / 1 -olefin copolymers wherein the 1 -olefin is prepared in situ, propylene / butadiene copolymers, isobutylene / isoprene copolymers, ethylene / vinyl cyclohexene copolymers, ethylene / alkyl acrylate copoly-mers, ethylene / alkyl methacrylate copolymers, ethylene / vi-nyl acetate copolymers, ethylene / acrylic acid copolymers and saltsthereof (ionomers), and also terpolymers of ethylene with propylene and a diene, such as hexadiene, dicyclopentadiene or ethylidene norbomene; and also mixtures of such copolymers with one another or with polymers mentioned under 1), for example polypropylene-ethylene / pro-pylene copolymers, LDPE-ethylene / vinyl acetate copolymers, LDPE-ethylene / acrylic acid copolymers, LLDPE-ethylene / vinyl acetate copolymers, LLDPE-ethylene / acrylic acid copolymers and alternately or randomly structured polyalkylene-carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides;

[0088] 4) polystyrene, expanded polystyrene (EPS) and extruded polystyrene (XPS), poly(p-methylstyrene), poly(a-methylstyrene), high impact polystyrene (HIPS), various grades of styrene-butadiene (SB), styrene-acrylonitrile (SAN) including grades of acrylonitrile-butadiene-styrene (ABS) copolymers and blends of HIPS-polyphenylene oxide (PPO) and ABS with polycarbonates (PC);

[0089] 5) aromatic homopolymers and copolymers derived from vinyl-aromatic monomers, for example, but not limited to, styrene, a-methylstyrene, all isomers of vinyltoluene, for example p-vinyltoluene, all isomers of ethylstyrene, propylstyrene, vinylbiphenyl, vinylnaphthalene, vinylanthracene and mixtures thereof; homopolymers and copolymers can have a syn-diotactic, isotactic, hemi-isotactic or atactic stereo structure; preference may be given to atactic polymers, and also included are stereo block polymers;

[0090] 6) homopolymers and copolymers that may have a syndiotactic, isotactic, hemi-isotactic or atactic stereo structure; preference may be given to atactic polymers, and also included are stereo block polymers;

[0091] 6a) copolymers including the already mentioned vinylaromatic monomers and co-monomers selected from ethylene, propylene, dienes, nitriles, acids, maleic anhydrides, maleic acid amides, vinyl acetate, vinyl chloride and acrylic acid derivatives and mixtures thereof, for example styrene / butadiene, styrene / acrylonitrile, styrene / ethylene (interpolymers), styrene / alkyl methacrylate, styrene / butadiene / alkyl acrylate and methacrylate, styrene / maleic anhydride, styrene / acrylonitrile / methylacrylate; high-impact-strength mixtures consisting of styrene copolymers and another polymer, for example a polyacrylate, a diene polymer or an ethylene / propylene / diene terpolymer; and also block copolymers of styrene, for example styrene / butadiene / styrene,styrene / isoprene / styrene , styrene / ethy lene-buty lene / styrene or styrene / ethylene- propylene / styrene;10092] 6b) hydrogenated aromatic polymers prepared by hydrogenation of the polymers mentioned under 6), especially polycyclohexylethylene (PCHE), often also referred to as polyvinylcyclohexane (PYCH), which is prepared by hydrogenation of atactic polystyrene;

[0093] 6c) hydrogenated aromatic polymers prepared by hydrogenation of the polymers mentioned under 6a);

[0094] 7) graft copolymers of vinylaromatic monomers, for example, but not limited to, styrene on polybutadiene, styrene on polybutadiene / styrene or polybutadiene / acrylonitrile copolymers, styrene and acrylonitrile (or methacrylonitrile) on polybutadiene; styrene, acrylonitrile and methylmethacrylate on polybutadiene; styrene and maleic anhydride on polybutadiene; styrene, acrylonitrile and maleic anhydride or maleic acid imide on polybutadiene; styrene and maleic acid imide on polybutadiene, styrene and alkyl acrylates or alkyl methacrylates on polybutadiene, styrene and acrylonitrile on ethylene / propylene / diene terpolymers, styrene and acrylonitrile on polyalkyl acrylates or polyalkylmethacrylates, styrene and acrylonitrile on acrylate / butadiene copolymers, and mixtures thereof with the copolymers mentioned above under 6), such as those known, for example, as so-called ABS, MBS, ASA or AES polymers;

[0095] 8) halogen-containing polymers, for example, but not limited to, polychloroprene, chlorinated rubber, chlorinated and brominated copolymer of isobutylene / isoprene (halobutylrubber), chlorinated or chlorosulphonated polyethylene, copolymers of ethylene and chlorinated ethylene, epichlorohydrin homo- and co-polymers, especially polymers of halogen-containing vinyl compounds, for example, but not limited to, polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride; and copolymers thereof, such as vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate or vinylidene chloride / vinyl acetate;

[0096] 9) polymers derived from a,P-unsaturated acids and derivatives thereof, such as, but not limited to, polyacrylates and polymethacrylates, or polymethyl methacrylates, polyacrylamides and polyacrylonitriles impact-resistant-modified with butyl acrylate;

[0097] 10) copolymers of the monomers mentioned under 9) with one another or with other unsaturated monomers, for example, but not limited to, acrylonitrile / butadiene co-polymers, acrylonitrile / alkyl acrylate copolymers, acrylonitrile / alkoxyalkyl acrylate copolymers, acrylonitrile / vinyl halide copolymers or acrylonitrile / alkyl methacrylate / butadiene terpolymers;

[0098] 11) polymers derived from unsaturated alcohols and amines or their acyl derivatives or acetals, such as, but not limited to, polyvinyl alcohol, polyvinyl acetate, stearate, benzoate or maleate, polyvinylbutyral, polyallyl phthalate, polyallylmelamine; and the copolymers thereof with olefins mentioned under 1);

[0099] 12) homo- and copolymers of cyclic ethers, such as, but not limited to, polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with bisglycidyl ethers;

[0100] 13) polyacetals, such as, but not limited to, polyoxymethylene, and also those polyoxymethylenes which contain comonomers, for example ethylene oxide; polyacetals modified with thermo-plastic polyurethanes, acrylates or MBS;

[0101] 14) polyphenylene oxides and sulphides and mixtures thereof with styrene polymers or polyamides;

[0102] 15) polyamides and copolyamides derived from diamines and dicarboxylic acids and / or from aminocarboxylic acids or the corresponding lactams, such as, but not limited to, polyamide 4, polyamide 6, polyamide 6 / 6, 6 / 10, 6 / 9, 6 / 12, 4 / 6, 12 / 12, polyamide 11, polyamide 12, aromatic polyamides derived from m-xylene, diamine and adipic acid; polyamide 61 (poly-hexamethylene isophthalimide, MXD (m- xylylenediamine); polyamides prepared from hexamethylenediamine and iso- and / or terephthalic acid and optionally an elastomer as modifier, for example poly-2, 4,4- trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide. Block copolymers of the above-mentioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, for example with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; and also polyamides or copolyamides modi-fied with EPDM or ABS; and polyamides condensed during processing (“RIM polyamide systems”); examples of polyamides and copolyamides that can may be used are derived from, inter alia, a-caprolactam, adipic acid, sebacic acid,dodecanoic acid, isophthalic acid, terephthalic acid, hexamethylenediamine, tetramethylenediamine, 2-methylpentamethylenediamine, 2,2,4- trimethylhexamethylenediamine, 2,4,4-trimethylhexamethylenediamine, m- xylylenediamine or bis(3-methyl-4-aminocyclohexyl)methane; and also semi-aromatic polyamides such as polyamide 35 66 / 61, for example consisting of 70-95% polyamide 6 / 6 and 5-30% polyamide 61; and also tricopolymers in which some of the poly-amide 6 / 6 has been replaced, for example consisting of 60-89% polyamide 6 / 6, 5-30% polyamide 61 and 1-10% of another aliphatic polyamide; the latter may consist of, for example, polyamide 6, polyamide 11, polyamide 12 or polyamide 6 / 12 units, such tricopolymers may accordingly be designated polyamide 66 / 61 / 6, polyamide 66 / 61 / 1 1, polyamide 66 / 61 / 12, polyamide 66 / 61 / 610 or polyamide 66 / 61 / 612;

[0103] 16) polyureas, polyimides, polyamide imides, polyether imides, polyester imides, poly-hydantoins and polybenzimidazoles;

[0104] 17) polyesters derived from dicarboxylic acids and dialcohols and / or from hydroxycarboxylic acids or the corresponding lactones, such as, but not limited to, polyethylene terephthalate, poly-propylene terephthalate, polybutylene terephthalate, poly- I, 4-dimethylolcyclohexane terephthalate, polyalkylenenaphthalate (PAN) and polyhydroxy-benzoates, and also block polyether esters derived from polyethers with hydroxyl terminal groups; and also polyesters modified with polycarbonates or MBS;

[0105] 18) polycarbonates and polyester carbonates;

[0106] 19) mixtures (polyblends) of the aforementioned polymers, for example, but not limited to, PP / EPDM, polyamide / EPDM or ABS, 60 PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PC / PBT, PVC / CPE, PVC / acrylates, POM / thermo-plastic PUR, PC / thermoplastic PUR, POM / acrylate, POM / MBS, PPO / HIPS, PPO / PA 6.6 and co-polymers, PA / HDPE, PA / PP, PA / PPO, PBT / PC / ABS or PBT / PET / PC; preference may be given to mixtures (polyblends) wherein the thermoplastic polymer is high-impact polystyrene (HIPS), expandable polystyrene (EPS), extruded polystyrene (XPS), polyphe-nylene ether (PPE), polyamide, polyester, polycarbonate (PC) or a polymer blend of the type ABS (acrylonitrile -butadiene-styrene) or PC / ABS (polycarbonate / acrylonitrilebutadiene-styrene) or PPE / HIPS (polyphenylene ether / highimpact polystyrene), especially a polyamide, polyester or a PPE / HIPS blend; special preference may be given to polymer compositions that may comprise a filler or areinforcing agent, especially glass-fibre-reinforced polymers, e.g., glass-fibre-reinforced polyamide. The finishing of styrene homo- and copolymers with flame-retardancy is important for many applications, for example for polystyrene particle foams made from expandable polystyrene (EPS) or extruded poly-styrene foam sheets (XPS) for insulating buildings, as well as for injection molded parts made from HIPS, ABS, ASA, etc. for use as parts and components in the electrical and electronics sector, such as, but not limited to, in electrical devices.

[0107] 20) natural polymers, for example, but not limited to, cellulose, starch(amylase and amylopectin), lignocellulose, proteins silk, poly-hydroxyalkanoates, polypeptides, polysaccharides such as, but not limited to, Xanthan gum, B-Glucans, chitosan and natural rubbers;

[0108] 21) biopolymers, for example polycaprolactones, poly-lactides, poly(Lactide- co-Glycolide) Copolymers (PLGA), poly(glycolic acid) (PGA) and polydioxanone (PDS).

[0109] Additionally, or alternatively, the polymer substrate consists of polystyrene, polystyrene copolymers, polyethylene, polypropylene or blends of polypropylene with polyolefins. Examples of blends include blends of polypropylene with polyethylene selected from the group consisting of high density polyeth-ylene (HDPE), high molecular weight high density polyethylene (HMW HDPE), ultrahigh molecular weight high density polyethylene (UHMW HDPE), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low-density polyethylene (LLDPE), branched low density polyethylene (BLDPE) and ethylene-propylene-diene terpolymers (EPDM) containing small (0.2-5 wt%) proportions of diene;

[0110] Additionally, or alternatively, the composition comprises a compound of formula (le) as defined in the present disclosure, and a polymeric substrate selected from the group consisting of polystyrene, expanded polystyrene (EPS) and extruded polystyrene (XPS), poly(p-methylstyrene), poly(a-methylstyrene), high impact polystyrene (HIPS), polypropylene, and polyamide.

[0111] Additionally, or alternatively, the composition further comprises one or more flame retardants.

[0112] Additionally, or alternatively, the composition further comprises one or more flame retardants each independently selected from the group consisting of (a), (b), (c), (d), (e) and (f), and combinations thereof:(a)wherein R1and R2are identical or different and are selected from the group consisting of linear or branched Ci-6-alkyl and Ce-io-aryl; M is selected from the group consisting of Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K, Zn, and a protonated nitrogen base; m is 1-4; n is 1-4; and x is 1-4;(b) a metal salt of hypophosphorous acid of the formula:wherein Met is a metal selected from groups I, II, III, and IV of the periodic table of elements; and n is 1-4 which corresponds to the charge of the corresponding metal ion Met;(c) a phosphonate or phosphonic acid diaryl ester of the formula:wherein R8and R10are H or Ci-8-alkyl; R9is Ci-4-alkyl; u is 1-5; and v is 1-5;(d) one or more of the following compounds:wherein M is a metal selected from groups II, III, 12 and 13 of the periodic table of elements; x is 2 or 3; n is 2-10; m is 0-25; R is H, halogen, or an aliphatic or aromatic radical with 1-32 C atoms and R1is H or Ci-6-alkyl; (e) one or more of the following compounds:wherein Al and A2, independently of each other, representing a substituted or unsubstituted, straight-chain or branched alkyl group with 1 to 4 carbon atoms, substituted or unsubstituted benzyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and A3 and A4, independently of each other, is methyl or ethyl and A5 is a straight-chain or branched alkyl group with 1 to 4 carbon atoms or a phenyl- or benzyl group which can have respectively up to 3 methyl groups; and(f) any brominated flame retardant including brominated poly(styrene-co-butadiene)wherein n, m, p, and q are each independently selected from 0-5000.With these embodiments, the plastic (polymeric) material, after incorporation of the compound of formula (I) or the polymer comprising one or more repeating units and a moiety of a compound of formula (I) (which polymer may be a copolymer / terpolymer) and the flame retardant(s) selected from (a), (b), (c), (d), and (e) to the polymeric substrate, has a flame retardancy rating of UL 94 V-2 or better and / or DIN4102-B2 rating, wherein the flame retardancy is measured according to DIN EN 60695-11-10 for UL 94 V tests, and wherein the flame retardancy is greater than the flame retardancy of the plastic material containing only a phosphorus containing flame retardant, a nitrogen-containing flame retardant, alkoxyamine (NOR), azoalkane, oxyimide, sulfenamide, silylamine, dicumene or a sulphur-containing flame retardant, or combination(s) thereof

[0113] Additionally, or alternatively, the composition further comprises one or more additives. Additionally, or alternatively, the one or more additives are each independently selected from the group consisting of polymer stabilizers and additional flame-retardants, such as melamine containing flame retardants, phosphorus containing flame-retardants, further nitrogen containing flame-retardants other than melamine containing flame retardants, inorganic flame-retardants and halogenated flame retardants.

[0114] Additionally, or alternatively, the stabilizer(s) is / are optionally halogen-free and may be selected from nitroxyl stabilizers, nitrone stabilizers, amine oxide stabilizers, benzofuranone stabilizers, phosphite and phosphonite stabilizers, quinone methide stabilizers and monoacrylate esters of 2,2'-alkylidenebisphenol stabilizers. Additional flame retardants as of one or more additives are known components, items of commerce or can be obtained by known methods.

[0115] Representative melamine containing flame retardants are for example, but not limited to, melamine comprising compounds, wherein the melamine structure 1,3,5- triazine-2,4,6-triamin (=cyanuric acid triamide) or condensates thereof are present. The definition applies to monomeric, oligomeric or polymeric co-pounds of melamine, condensates of melamine or condensates with of melamine and phosphoric thereof.

[0116] Preferred melamine comprising compounds are melamine cyanurate, melamine phosphate, dimelamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine phenyl phosphonate, melamine borate, melamine ammonium phosphate, melamine ammonium polyphosphate, melamine ammonium pyrophosphate, melem, melam or melon or polyphosphates of melem, melam or melon.

[0117] Representative phosphorus containing flame-retardants are for example: organic metal phosphinates (aluminium phosphinates, Exolit OP, Clariant), pentaerythritol phosphates, tetraphenyl resorcinol diphosphite (FYROLFLEX® RDP, Akzo Nobel), tetrakis(hydroxy-methyl)phosphonium sulphide, triphenyl phosphate, diethyl-N,N-bis(2- hydroxy-ethyl)-amino-methyl phosphonate, hydroxyalkyl esters of phosphorus acids and cyclic phosphonates (ADK STAB FP 600 / 800 / 2200, Adeka Corp), AFEAMMIT PCO 900 (CAS No.: 3001-98-7) / 800 / 700, (Thor GmbH), ammonium polyphosphate (APP), EXOEIT AP 766 (Clariant) or HOSTAFEAM® AP750 (Clariant), resorcinol diphosphate oligomer (RDP), phosphazene flame-retardants, 9,10-dihydro-9-oxa-10- phosphaphenanthrene-10-oxide (DOPO, CAS No: 35948-25-5) or its derivatives, N,N-bis- (2 -hydroxylethyl) aminomethane phosphonic acid diethyl ester, CAS No. 2781-11-5 63, Poly(m-phenylene methylphosphonate), CAS No. 63747-58-0, Polyphosphonate, CAS No. 68664-06-2, Poly[phosphonate-co-carbonate], CAS No. 77226-90-5, Phosphoric acid, mixed esters with [l,l'-bisphenyl-4,4'-diol] and phenol, CAS No. 1003300-73-9, Oligomeric phosphonate polyol, CAS No. 363626-50-0, Organophosphates (phosphate esters) - Aryl phosphates, Triphenyl phosphate, CAS No. 115-86-6, Phenol,isobutylenated, phosphate (3:1), CAS No. 68937-40-6, Tricresyl phosphate, CAS No. 1330-78-5, Cresyl diphenyl phosphate, CAS No. 26444-49-5, Phosphoric acid, bis(methylphenyl) phenyl ester, CAS No. 26446-73-1, Resorcinol bis-diphenyl phosphate, CAS No. 57583-54-7, Bisphenol A bis(diphenyl phosphate), CAS No. 5945-33-5, Organophosphates (phosphate esters) - Alkyl phosphates, Oligomeric ethyl ethylene phosphate, CAS No. 184538-58-7, Organophosphates (phosphate esters) - Aryl alkyl phosphates, Isopropyl phenyl phosphate, CAS No. 68937-41-7, Tris (p-t-butylphenyl) phosphate, CAS No. 78-33-1, Melamine-derived and other organic phosphates (not being esters), Melamine pyrophosphate, CAS No. 15541-60-3, Melamine phosphate, CAS No. 41583-09-9, Diphosphoric acid, compd. with piperazine, CAS No. 66034-17-1, and substituted amine phosphate (confidential CAS No.), Ammonium polyphosphate, CAS No. 68333-79-9, Red phosphorus, CAS No. 7723-14-0, Phosphinic acid, aluminium salt (3:1), CAS no. 7784-22-7, Phosphinic acid, aluminium salt (3:1), CAS no. 7784-22-7, Ethylenediamine-o-phosphate, CAS No. 14852-17-6, Diethylphosphinate, aluminium and zinc salts with melamine polyphosphinate synergist, CAS No. 225789-38-8, halogen-free flame retardant, Emerald Innovation™ NH-1*, Fyrol™ HF-5, 4.7.5 6H-Dibenz[c,e][l,2]oxa-phosphotin-6-propanoic acid, butyl ester, 6-oxide, CAS No. 848820- 98-4, di(ethylenediamine) phosphate (DEDAP), and ethylenediamine diphosphate (EDAP) or their mixtures (e.g., BUDIT 3167, Budenheim).

[0118] Further nitrogen containing flame retardants other than melamine containing flame retardants are, for example, isocyanurate flame-retardants, such as polyisocyanurate, esters of isocyanuric acid or isocyanurates, melamine metal phosphates (SAFIRE® 200 / 400 / 600, Floridienne Chimie). Representative examples are hydroxyalkyl isocyanurates, such as tris-(2-hydroxyethyl)isocyanurate, tris(hydroxymethyl)isocyanurate, tris(3-hydroxy-n-proyl)isocyanurate or triglycidyl isocyanurate. Further examples are: benzoguanamine, tris(hydroxyethyl) isocyanurate, allantoin, glycouril, melamine cyanurate, urea cyanurate, poly-[2,4-(piperazine-l,4-yl)-6-(morpholine-4-yl)-l,3,5- triazine] / piperazin (MCA® PPM TRIAZINE HF, MCA Technologies) azoalkanes and related compounds (e.g. AZONOR, azine, azoxy, hydrazone, triazenyl, INAZO), NOR compounds (FLAMESTAB® NORI 16 Cas No. 191680-81-6, TINUV1NTM NOR 371 Cas No. 565450-39-7, BASF), or ammonium polyphosphate.

[0119] Additionally, or alternatively, the compound or polymer as disclosed herein may be used as flame retardants together with a synergist based on other radicalgenerators, e.g., but not limited to, disulfides, oxyimides, silylamines, dicumene and peroxides.

[0120] Representative organohalogen flame-retardants are, for example, but not limited to, polybrominated diphenyl oxide (DE-60F, Great Lakes Corp.), decabromodiphenyl ethane (SAYTEX™ 35 8010, Albemarle), hexabromocyclododecane (SAYTEX™ HP 900P, Albemarle), brominated polymers and oligomers such as styrenebutadiene block copolymers (Emerald 3000 (Butadiene styrene brominated copolymer CAS No. 1195978-93-8) EMERALD INNOVATION™ 3000, Chemtura, GREEN ARMOR™, GREEN CREST™, Albemarle, FR-122P™, ICL), polyphenylene oxide and its derivatives, brominated polyacrylates (FR-1025 P™ Cas No. 59447-57-3, ICL), decabromodiphenyl oxide (DBDPO; SAYTEX ® 102E), tris [3-bromo-2,2- bis(bromomethyl)propyl] phosphate (PB 370®, FMC Corp.), tris(2,3-dibro- mopropyl)phosphate, tris(2,3-dichloropropyl)phosphate, chlorendic acid, tetrachlorophthalic acid, tetrabromophthalic acid, poly-P-chloroethyl triphosphonate mixture, tetrabromobisphenol A bis(2,3-dibromopropyl ether) (PE68), brominated epoxy resin, ethylene-bis(tetrabromophthalim-ide) (SAYTEX® BT-93), bis(hexachlorocyclopentadieno) cyclooctane (DECHLORANE PLUS®), chlorinated paraf-fins, octabromodiphenyl ether, hexa-chlorocyclopentadiene derivatives, 1,2- bis(tribromophenoxy)ethane (FF680), tetra-bromo-bisphenol A (SAYTEX® RB 100), ethylene bis-(dibromonorbomane-dicarboximide) (SAYTEX® BN-451), PTFE, tris-(2, 3- dibromopropyl )-iso-cyanurate, and ethylene-bistetrabromophthalimide. The flameretardant mentioned above routinely combined with inorganic (hydr)oxide synergists. Most common for this use are aluminum (hydr)oxide, such as Al(OH)s or A1OOH, magnesium hydroxide, zinc or antimony oxides, e.g., Sb20s or Sb20s. Boron compounds are suitable, too. If a plurality of components / flame-retardants) is added to the composition, these can be up to 45.0% by weight of the polymer substrate; for instance, about 0.25% to about 35.0%; for example, about 0.25% to about 30.0%, by weight of the polymer substrate.

[0121] Additionally, or alternatively, the above-mentioned additional flame retardant compounds are advantageously contained in the composition of disclosed embodiments in an amount from about 0.25 % to about 45.0% by weight of the polymer substrate, for instance about 0.25% to about 35%; for example about 0.25% to about 30% by weight of the polymer substrate.

[0122] As mentioned above, the composition as disclosed herein may additionally contain one or more conventional additives, for example selected from pigments, dyes, plasticizers, antidripping agents such as fluorinated polymers (PTFE, Metablen A3800, Mitsubishi Rayon), nanoclays (Cloisite 30B) and borates (FIREBRAKE®, Borax), antioxidants, thixotropic agents, levelling assistants, basic co-stabilizers, metal passivators, metal oxides, organo-phosphorus compounds, further light stabilizers and mixtures thereof, especially pigments, phenolic antioxidants, calcium stearate, zinc stearate, UV absorbers of the 2-hydroxy-benzophenone, 2-(2'-hydroxyphenyl)benzotriazole and / or 2-(2- hydroxyphenyl)-l ,3,5-triazine groups.

[0123] The additives mentioned above are optionally contained in an amount of 0.01 to 10.0%, especially 0.05 to 5.0%, relative to the weight of the polymer substrate (b).

[0124] Disclosed embodiments accordingly relate also to the use of the compounds of formula (I) as defined above for imparting flame-resistant properties to a polymer substrate, for example synthetic polymers, especially to thermoplastics as well as foamed thermoplastics, and also to a method of imparting flame-resistant properties to synthetic polymers, wherein at least one compound of formula (I) according to disclosed embodiments is incorporated in the polymer substrate or is applied to their surface.

[0125] The incorporation of the compounds of formula (I) and the optional additional components, as defined above, into the polymer substrate is carried out by known methods such as dry blending in the form of a powder, or wet mixing in the form of solutions, dispersions or suspensions for example in an inert solvent, water or oil. The compound of formula (I) and optional further additives may be incorporated, for example, before or after molding or also by applying the dissolved or dispersed additive or additive mixture to the polymer material, with or without subsequent evaporation of the solvent or the suspension / dispersion agent. They may be added directly into the processing apparatus (e.g., extruders, internal mixers, etc.), e.g., as a dry mixture or powder, or as a solution or dispersion or suspension or melt.

[0126] Alternatively, the compound of disclosed embodiments can be incorporated to the backbone of a polymeric substrate or of part of a polymeric substrate, or of one or more polymeric component(s) of the polymeric substrate. Grafting can be affected in a manner known in the art using compounds of formula (I) which comprise functionalities in the substituents R, R', R” or R’” which are reactive with the functionalities of thepolymeric material. Thus, the compounds of formula (I) and their use as flame retardants cover also such embodiments, wherein they are incorporated chemically to a part or all of the polymeric material ("functionalized / grafted" polymeric material) of the polymeric substrate. If the polymeric substrate comprises two or more different polymeric materials, the compound(s) of formula (I) may be combined by mixing or grafting with one of the polymeric materials to obtain a first composition, and the rest of the two or more polymeric materials may be added to the obtained first composition. E.g., when the polymeric substrate comprises wood (cellulose) and polypropylene, the compound(s) of formula (I) (flame retardant(s)) may be grafted to cellulose and then admixed with polypropylene.

[0127] The addition of the additive components to the polymer substrate may be carried out in all customary mixing machines in which the polymer is melted and mixed with the additives. Suitable machines are known to those skilled in the art. They are predominantly mixers, kneaders and extruders. If a plurality of components is added, these can be premixed or added individually. In such operations, the polymer can be used in the form of powder, granules, solutions, and suspensions or in the form of lattices.

[0128] The compounds of formula (I) and optional further additives may also be added to the polymer substrate in the form of a master batch ("concentrate") which contains the components in a concentration of, for example, about 1.0% to about 80.0% and optionally 2.0% to about 40.0% by weight incorporated in a polymer. In such operations, the polymer can be used in the form of powder, granules, solutions, and suspensions or in the form of lattices.

[0129] Incorporation may take place prior to or during the shaping operation. The materials containing the additives described herein may be optionally used to produce molded articles, for example rotomolded articles, injection molded articles, profiles and the like, and especially a fiber, spun melt non-woven, film or foam. Thus, disclosed embodiments may pertain to molded or extruded articles, such as pipes, wire and cables, fibers, spun melt non-woven or a foam comprising the compound or composition of disclosed embodiments.

[0130] Thus, in accordance with disclosed embodiments, a compound of formula (I), a polymer, and a composition as defined in herein can be used for providing a flameresistant product.

[0131] The compounds of formula (I) and the polymers comprising one or more repeating units and a moiety of a compound of formula (I) can be prepared by methods known by person skilled in the art or by methods disclosed herein. Suitable methods are described for example in Table 4 (using compound of structure 8).

[0132] The polymer comprising one or more repeating units and a moiety of a compound of formula (I) may be prepared, e.g., by optionally substituting a compound of formula (I) as disclosed herein with a reactive group such as amino, hydroxy or epoxy functionality, and reacting the obtained compound, or by polymerizing a compound of formula (I), optionally in the presence of another polymerizable monomer. For instance, but not limited to, one or more of the compounds represented by the following structures may be used to prepare the polymer:

[0133] Additionally, or alternatively, the moiety of the compound of formula (I) may be linked to a polymeric backbone by suitable linking groups, such as vinyl groups, to obtain the polymer.

[0134] In one aspect is provided a use of a compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound formula (I), or a composition as defined in the present disclosure as a flame retardant or as a synergist with one or more flame retardants, preferably as a flame retardant for a synthetic or natural polymer.

[0135] Additionally, or alternatively, the synthetic and natural polymer is selected from foamed polystyrene, such as expanded polystyrene (EPS), extruded polystyrene (XPS), foam sheets prepared from homopolymeric polystyrene or co- / terpolymers of polystyrene.

[0136] In one aspect is provided a use of a compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in the present disclosure as a component in polymer extrusion or in polymerization processes.

[0137] In one aspect is provided a method for producing molding compounds, wherein the method comprises: a) providing a melt composition comprising a polymer melt comprising at least one compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in the present disclosure, preferably the melt composition further comprises an organic blowing agent, wherein the temperature of the melt composition is at least 120 °C, such as 120 - 300 °C; b) discharging the melt composition through a nozzle plate having one or more holes, preferably the diameter at the nozzle outlet of the holes of the nozzle plate is < 1.5 mm; and c) granulating the discharged melt composition, preferably directly behind the nozzle plate under water at a pressure within the range of 1 to 20 bar.

[0138] Additionally, or alternatively, the melt composition further comprises a polymeric substrate.

[0139] Additionally, or alternatively, the method comprises, before a), mixing an organic blowing agent with, preferably into, the polymer melt, wherein the polymer melt comprises or is free of one or more phosphorus-containing additive, preferably by means of static and / or dynamic mixers, at a temperature of at least 150 °C, such as 150 - 300 °C, preferably at ca. 180 °C; and, before b), cooling the melt composition to a temperature of at least 120 °C.

[0140] In one aspect is provided a method for producing molding compounds, wherein the method comprises:a) polymerizing a first composition comprising a compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in the present disclosure, optionally in the presence of one or more vinylic monomers, to form a first polymer; b) optionally adding before, during, and / or after the polymerizing in a) one or more of an organic blowing agent, suspension agent, and nucleating agent, or a combination thereof to the first composition or to the formed first polymer; and c) separating the formed first polymer, such as copolymer, preferably by means of sieving.

[0141] Additionally, or alternatively, the method comprises: a) polymerizing a first composition comprising one or more vinylic monomers in the presence of a compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in the present disclosure, to form a first polymer; b) adding before, during, and / or after the polymerizing in a) an organic blowing agent, optionally adding further one or more of a suspension agent, and nucleating agent, or a combination thereof, to the first composition or to the formed first polymer, thereby to form an expandable, blowing agent-containing copolymer; and c) separating the formed expandable, blowing agent-containing copolymer, preferably by means of sieving.

[0142] Additionally, or alternatively, the one or more vinylic monomers is styrene.

[0143] Additionally, or alternatively, athermanous particles and a nonionic surfactant are mixed with a melt of the styrene (co)polymer, preferably in an extruder. At the same time, the blowing agent is metered into the melt. Athermanous particles are understood to mean particles that are impermeable to infrared radiation (heat radiation).

[0144] The athermanous particles may also be incorporated into a melt of styrene (co)polymer containing a blowing agent, wherein it is expedient to use screened edge fractions of a bead spectrum of blowing agent-containing polystyrene beads formed in a suspension polymerization. The blowing agent and the styrene (co)polymer melts containing athermanous particles are pressed out and comminuted to form blowing agentcontaining granules. Because the athermanous particles can have a strong nucleating effect, it may be beneficial to cool them under pressure quickly after pressing to avoid foaming. Itis therefore expedient to carry out under-water granulation under pressure in a closed system.

[0145] It is also possible to add the blowing agent to the styrene (co)polymers that contain athermanous particles in a separate method step. Here, the granules are then preferably impregnated with the blowing agent in an aqueous suspension.

[0146] In all three cases, the fine, athermanous particles and the nonionic surfactant may be added directly to a styrene (co)polymer melt. However, the athermanous particles may also be added to the melt in the form of a concentrate in polystyrene. Preferably, however, styrene (co)polymer granules and athermanous particles are fed together into an extruder, where the styrene (co)polymer is melted and mixed with the athermanous particles. The expandable styrene (co)polymers (EPS) are particularly preferably prepared by polymerizing styrene and, optionally, in the presence of disclosed flame retardants or copolymerizable monomers of the disclosed flame retardants in an aqueous suspension and impregnation with a blowing agent, wherein the polymerization is carried out in the presence of 0.1 to 5% by weight of graphite particles based on the weight of the styrene (co)polymer and a nonionic surfactant. Suitable nonionic sur-factants are, for example, maleic anhydride copolymers (MA), for example from maleic anhydride and C20-24 olefin, polyisobutylene succinic anhydride (PIBSA) or reaction products thereof with hydroxy polyethylene glycol ester, diethylaminoethanol or amines such as tridecylamine, octylamine or polyetheramine, tetraethylenepentamine, or mixtures thereof. The molecular weights of the nonionic surfactant are preferably within the range of 500 to 3000 g / mol. They are generally used in amounts ranging from 0.01 to 2% by weight based on the styrene (co)polymer. The styrene (co)polymers containing expandable, athermanous particles can be processed into styrene (co)polymer foams having densities of 5-200 kg / m3, preferably 7 to 100 kg / m3and in particular 10-80 kg / m3.

[0147] For this purpose, the expandable particles may be prefoamed. This is usually done by heating the particles with water vapor in what are referred to as prefoamers. The particles prefoamed in this way may then be welded to form molded bodies. For this purpose, the prefoamed particles may be placed in non-gastight molds and treated with water vapor. After cooling, the molded parts may be be removed. The foams produced from the expandable styrene (co)polymers according to the invention are distinguished by excellent thermal insulation. This effect is particularly evident at low densities.

[0148] The foams may be used for thermal insulation of buildings and parts of buildings, for thermal insulation of machines and household appliances, and as packaging materials. To produce the expandable styrene (co)polymers, the blowing agent may be mixed into the polymer melt. One possible method comprises the steps of a) melt production, b) mixing, c) cooling, d) conveying and e) granulating. Each of these steps can be carried out by the apparatus or apparatus combinations known in plastics processing. Static or dynamic mixers, for example extruders, are suitable for mixing. The polymer melt can be taken directly from a polymerization reactor or produced directly in the mixing extruder or a separate melting extruder by melting polymer granules. The melt can be cooled in the mixing units or in separate coolers. For the granulation, for example, pressurized underwater granulation, granulation with rotating blades and cooling by spray nebulization of temperature control liquids or atomization granulation may be considered. Apparatus arrangements suitable for carrying out the method are, for example, but not restricted to, polymerization reactor-static mixer / cooler-granulator, polymerization reactor- extruder-granulator, extruder-static mixer-granulator, and extruder-granulator.

[0149] The blowing agent-containing styrene (co)polymer melt is generally conveyed through the nozzle plate at a temperature within the range of 140 to 300 °C, preferably within the range of 160 to 240 °C. Cooling down to the glass transition temperature range is not necessary.

[0150] The nozzle plate is heated to at least the temperature of the blowing agentcontaining styrene (co)polymer melt. The temperature of the nozzle plate is preferably within the range of 20 to 100° C above the temperature of the blowing agent-containing styrene (co)polymer melt. This prevents polymer deposits in the nozzles and ensures trouble-free granulation.

[0151] To obtain marketable granule sizes, the diameter (D) of the nozzle bores at the nozzle outlet should be within the range of 0.2 to 1.5 mm, preferably within the range of 0.3 to 1.2 mm, particularly preferably within the range of 0.3 to 0.8 mm. In this way, granule sizes of less than 2 mm, in particular the range of 0.4 to 1.4 mm, can be set in a targeted manner even after strand expansion.

[0152] A particularly preferred method for producing fire-retardant, expandable styrene (co)polymers (EPS) comprises:al) mixing an organic blowing agent into the polymer melt of a copolymer as disclosed in the present disclosure and / or mixtures thereof by means of static or dynamic mixers at a temperature of at least 150 °C, thereby providing a melt composition comprising a blowing agent-containing styrene (co)polymer melt; b) cooling the melt composition comprising the blowing agent-containing styrene (co)polymer melt to a temperature of 120 to 200 °C; c) discharging the cooled melt composition through a nozzle plate having one or more holes whose diameter at the nozzle outlet is <1.5 mm; and d) granulating the discharged cooled melt composition directly behind the nozzle plate under water at a pressure within the range of 1 to 20 bar.

[0153] It is also possible to produce the copolymers and / or molding compounds according to the invention by means of suspension polymerization. In suspension polymerization, styrene may be polymerized in the presence of the compound of formula (I) or the polymer comprising one or more repeating units and a moiety of a compound of formula (I) as disclosed in the present disclosure. Up to 50% of the weight of styrene may be replaced by other ethylenically unsaturated monomers.

[0154] In suspension polymerization, one or more auxiliaries, such as peroxide initiators, suspension stabilizers (agents), (organic) blowing agents, chain transfer agents, expansion aids, nucleating agents, and plasticizers, may be used. Blowing agents may be added in amounts of 3 to 10% by weight based on the monomer(s). They may be added to the suspension before, during or after polymerization. Suitable blowing agents are aliphatic hydrocarbons having 4 to 6 carbon atoms. It is advantageous to use inorganic Pickering dispersants such as magnesium pyrophosphate or calcium phosphate as suspension stabilizers.

[0155] The suspension polymerization produces bead-shaped, substantially round particles having an average diameter within the range of 0.2 to 2 mm.

[0156] To improve processability, the finished, expandable styrene(co)polymer beads and granules can be coated with customary and known coating agents such as, for example, metal stearates, glycerol esters and fine-particle silicates, antistatic agents or anticaking agents.

[0157] The EPS granules can be mixed with glycerol monostearate (GMS, typically 0.25% by weight), glycerol tristearate (typically 0.25% by weight), fine-particle silica (Aerosil R972, typically 0.12% by weight) and zinc stearate (typically 0.15% by weight) and an antistatic agent.

[0158] In a first step, the expandable styrene (co)polymer particles according to the invention may be prefoamed by means of hot air or water vapor to give foam particles having a density within the range of 20 to 500 kg / m3, in particular 10 to 100 kg / m3, and in a second step the material may be fused in a closed mold to give molded foams.

[0159] The expandable styrene (co)polymer particles can be processed into polystyrene foams having densities of 8 to 200 kg / m3, preferably 10 to 100 kg / m3. For this purpose, the expandable particles are pre-foamed. This is usually done by heating the particles with water vapor in what are referred to as prefoamers. The particles prefoamed in this way are then welded to form semi-finished products or molded bodies. For this purpose, the prefoamed particles are placed in non-gastight molds and treated with water vapor. After cooling, the molded parts can be removed.

[0160] In one aspect is provided a molding compound obtainable by a method as defined in the present disclosure.

[0161] In one aspect is provided a use of a compound of formula (I), a polymer, or a composition as defined in the present disclosure as an individual component or cocomponent of insulating material for buildings or as a part and / or component in electrical devices.

[0162] In one aspect is provided a use of a compound, a polymer, or a composition as defined in the present disclosure as synergist with one or more flame retardants.

[0163] In one aspect is provided a method for the preparation of a compound of formula (I) as defined in the present disclosure, wherein the method comprises: i) providing a reaction composition comprising a compound of formula (X):formula (X), whereinX, X’, R’, R”, and R”’ are as defined in the present disclosure; and a base, preferably NaH, thereby deprotonating the nitrogen of the compound of formula (X); ii) optionally heating the reaction composition; iii) adding to the reaction composition a compound of formula (XII):R-S-X’” formula (XII), whereinR is as defined in the present disclosure;X’” is a leaving group, preferably the leaving group is selected from the group consisting of a halogen, preferably the halogen is I, Br, or Cl, thereby forming a compound of formulaformula (I), whereinX, X’, R, R’, R”, and R”’ are as defined in the present disclosure.

[0164] In one aspect is provided a method for the preparation of a polymer comprising one or more repeating units and a moiety of a compound of formula (I), as defined in the present disclosure, wherein the method comprises: i) providing a reaction composition comprising a compound of formula (I):formula (I), whereinX, X’, R, R’, R”, and R”’ are as defined in the present disclosure; and optionally one or more monomers; ii) optionally heating the reaction composition, thereby forming a polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in the present disclosure.

[0165] Examples

[0166] Preparation of compounds of formula (I). The flame retardants can be synthesized according to the general scheme 1. Noteworthy is that other synthetic routes for the synthesis of inventive flame retardants may also be utilized.X, X’, R, R’, R”, and R’” are as defined in the present disclosure.Scheme 1. General synthetic route and description to the inventive flame retardants.

[0167] General synthetic method for the preparation of compounds of formula (I)1 Eq of the phosphoramide was dispersed in THF (around 0.8 M concentration). 1.1 Eq of sodium hydride was added in one portion to the dispersion. After the addition, no significant gas evaluation was observed. The mixture was warmed up and intensive gas formation was observed. The temperature of the mixture was kept constant at 50 °C to control the gas formation. When gas formation slowed down, the reaction mixture (RM) was heated to reflux. After the gas formation stopped, the reaction mixture was cooled down to room temperature (RT). To the slightly cloudy reaction mixture was added a solution of the intermediate S-Cl prepared by the following method:

[0168] 0.5 Eq. of the corresponding disulfide was dispersed in DCM (ca. 0.7 M concentration). Then 0.5 Eq of sulfuryl chloride was added in one portion at RT. After 20 min of mixing at RT, the reaction mixture was concentrated to dryness. The residue was dissolved in DCM (to ca. 0.8 M concentration) and the solution was added dropwise to the previously prepared solution of the deprotonated phosphoramide . During the addition the temperature of the reaction mixture was kept under 30 °C.

[0169] The reaction mixture was stirred overnight at RT and the solvents were evaporated in vacuum. The residue was diluted with solvent A and then filtered. The precipitate was washed on filter with water and then with Solvent B and / or Solvent A. After drying in vacuum, the compound (PNS derivative) with formula (I) was obtained with the yield 48-78% as a white to creamy powder. NMR (1H,31P,13C) confirms the purity of the product. HRMS confirms the molecular composition.

[0170] Synthesis of compounds 1, 2, 3, 4, 5, 6, 7 and 8

[0171] Synthesis of compound 1 (with formula (la))In a 2 L 3 -necked flask (Ar atmosphere) was placed 6-(tert- butylamino)dibenzo[c,e][l,2]oxa-phosphinine 6-oxide (196.2 g, 1 Eq, 682.9 mmol) and THF (800 mL). To the suspension was added sodium hydride (30.05 g, 60% wt, 1.1 Eq, 751.2 mmol) in one portion. After the addition no gas evaluation was observed. Then the mixture was warmed up to 40 °C. Intensive gas evaluation started during warming up the reaction mixture. When gas evaluation slowed down (~1.5 h) the RM was heated to reflux. After the gas evaluation stopped (~2h) the reaction mixture cooled down to room temperature. To the slightly cloudy reaction mixture was added a solution of the intermediate S-Cl prepared by the following method:

[0172] To a 1 L flask (Ar atmosphere) was placed l,2-bis(benzo[d]thiazol-2- yl)disulfane (113.5 g, 0.5 Eq, 341.5 mmol) and 500 mL of DCM to form a suspension. Sulfuryl chloride (46.08 g, 27.76 mL, 0.5 Eq, 341.5 mmol) was added to the suspension in one portion at room temperature. After the sulfuryl chloride dissolved and a deep red solution was formed (after ~20 min), the reaction mixture was evaporated using rotary evaporator (vacuum was released by nitrogen gas to avoid the hydrolysis of the product by air moisture). The residue was dissolved in DCM (500 mL) and the solution was transferred to the dropping funnel and was added dropwise to the previously preparedsolution of the deprotonated phosphoramide. During the addition, the temperature of the reaction mixture was kept under 25 °C. The addition took approx. 50 min.

[0173] The reaction mixture was stirring overnight at RT and then the solvents were evaporated in vacuum. The residue was diluted with Et2O (600 mL) and with water solution of a phosphate buffer (500 mL, pH 7, 0.1M) and then filtered. The precipitate was washed with water (3x300 mL) and then with ethanol (3x400 mL) and Et2O (200 mL). After drying in vacuum, 6-((benzo[d]thiazol-2-ylthio)(tert- butyl)amino)dibenzo[c,e][l,2]oxaphosphinine 6-oxide (PNS-1) was obtained (235 g, 519 mmol, 76.0 %) as a white powder. NMR: (mixture of diastereomers 42:58).1H NMR (500 MHz, DMSO-7e) 5 ppm 1.64 (s, 9 H) 1.70 (s, 9 H) 6.74 (d, 7=8.00 Hz, 1 H) 7.02 (t, J=1.63 Hz, 1 H) 7.14 (t, 7=7.48 Hz, 1 H) 7.25 (td, <7=7.40, 3.20 Hz, 1 H) 7.30 - 7.47 (m, 6 H) 7.53 (dt, 7=17.28, 8.53 Hz, 2 H) 7.68 (td, 7=7.50, 2.90 Hz, 1 H) 7.71 (d, 7=8.09 Hz, 2 H) 7.81 (t, 7=7.71 Hz, 1 H) 7.88 (dd, 7=14.88, 7.71 Hz, 1 H) 7.96 (s, 2 H) 8.01 - 8.16 (m, 3 H) 8.19 (d, 7=7.78 Hz, 1 H) 8.26 (t, 7=7.17 Hz, 1 H),31P NMR (202 MHz, DMSO-76) 8 ppm 15.68 (d, 7=14.93 Hz, 1 P) 17.62 (d, 7=12.44 Hz, 1 P),13C NMR (126 MHz, DMSO-76) 8 ppm 30.46 (s, 3 C) 30.78 (s, 3 C) 64.93 (d, 7=4.54 Hz, 1 C) 65.06 (d, 7=5.45 Hz, 1 C) 119.30 (d, 7=6.36 Hz, 1 C) 119.91 (d, 7=7.27 Hz, 1 C) 121.16 (d, 7=9.99 Hz, 1 C) 121.91 (s, 1 C) 121.96 (s, 1 C) 122.32 (br. s„ 1 C) 122.35 (br. s„ 1 C) 122.76 (d, 7=14.53 Hz, 1 C) 123.43 (d, 7=17.26 Hz, 1 C) 124.08 (d, 7=11.81 Hz, 1 C) 124.22 (d, 7=10.90 Hz, 1 C) 124.72 (s, 1 C) 125.04 (s, 1 C) 125.18 (s, 1 C) 125.76 (s, 1 C) 126.07 (d, 7=15.44 Hz, 1 C) 126.85 (d, 7=3.63 Hz, 2 C) 127.39 (s, 1 C) 128.08 (d, 7=14.53 Hz, 1 C) 129.45 (d, 7=14.53 Hz, 1 C)130.12 (d, 7=9.08 Hz, 1 C) 130.57 (s, 1 C) 131.08 (d, 7=9.99 Hz, 1 C) 131.30 (s, 1 C)133.88 (d, 7=3.00 Hz, 1 C) 134.03 (d, 7=2.00 Hz, 1 C) 134.75 (s, 1 C) 134.90 (s, 1 C)136.08 (s, 1 C) 136.95 (d, 7=6.36 Hz, 1 C) 137.05 (d, 7=6.36 Hz, 1 C) 150.23 (d, 7=9.08Hz, 1 C) 150.78 (d, 7=9.99 Hz, 1 C) 153.26 (s, 1 C) 153.40 (s, 1 C) 172.71 (s, 1 C) 173.10 (s, 1 C). HPLC-HRMS: composition found: C23H21N2O2PS2.

[0174] Synthesis of compound 2 (with formula (lb))Compound 2 was synthesized using general synthetic method described above using diphenyl Ze / 7-buty I phosphoram idatc as starting phosphoramide and 1,2- bis(benzo[d]thiazol-2-yl)disulfane as starting disulfide. Derivative 2 was obtained with the yield of 64%. 'H NMR (500 MHz, CHLOROFORM- ) 5 ppm 1.62 (s, 9 H) 7.03 - 7.37 (m, 11 H) 7.42 (td, <7=7.71, 1.07 Hz, 1 H) 7.75 (d, J=1.63 Hz, 1 H) 7.86 (d, J=8.09 Hz, 1 H),31P NMR (202 MHz, CHLOROFORM- ) 5 ppm -2.57 (s, 1 P),13C NMR (126 MHz, CHLOROFORM -<7) 5 ppm 30.22 (d, <7=2.72 Hz, 3 C) 64.84 (d, <7=6.36 Hz, 1 C) 119.95 - 120.25 (m, 4 C) 120.69 (d, <7=4.54 Hz, 2 C) 121.09 (s, 1 C) 122.07 (s, 1 C) 124.39 (s, 1 C) 124.97 (s, 1 C) 125.33 (s, 1 C) 126.20 (s, 1 C) 129.41 - 129.88 (m, 4 C) 135.28 (s, 1 C) 153.74 (s, 1 C) 174.02 (s, 1 C). HPLC-HRMS: composition found: C23H23N2O3PS2.

[0175] Synthesis of compound 3 (with formula 6 Ic ) )Compound 3 was synthesized using general synthetic method described above using diphenyl phenylphosphoramidate as starting phosphoramide and l,2-bis(benzo[d]thiazol-2- yl)disulfane as starting disulfide. Compound 3 was obtained with the yield of 67%. ' H NMR (500 MHz, , DMSO-t / 6) 5 ppm 6.96 (t, J=7.32 Hz, 1 H) 7.17 (d, J=7.63 Hz, 2 H) 7.19 - 7.25 (m, 5 H) 7.25 - 7.32 (m, 2 H) 7.35 - 7.42 (m, 4 H) 7.42 - 7.47 (m, 1 H) 7.50 - 7.55 (m, 1 H) 7.95 (d, J=8.09 Hz, 1 H) 8.07 (d, J=7.63 Hz, 1 H) 8.84 (d, J=10.38 Hz, 1 H), 3 IP NMR (202 MHz, DMSO-t / 6) 5 ppm -1.88 (d, J=9.95 Hz, 1 P), 13C NMR (126 MHz, DMSO-<76) 5 ppm 117.76 (d, >8.18 Hz, 2 C) 120.08 (d, J=5.45 Hz, 4 C) 121.64 (s, 2 C) 122.23 (s, 1 C) 122.38 (s, 1 C) 125.09 - 125.37 (m, 2 C) 125.42 - 125.70 (m, 1 C) 126.92 (s, 1 C) 129.24 (s, 2 C) 129.96 (s, 4 C) 135.61 (s, 1 C) 139.74 (s, 1 C) 150.04 (d, J=7.27 Hz, 1 C) 153.85 (s, 1 C) 167.24 (s, 1 C). HPLC-HRMS: composition found: C25H19N2O3PS2.

[0176] Synthesis of compound 4 (with formula (Id))Compound 4 was synthesized using general synthetic method described above using 6- (benzylamino)dibenzo[c,e][l,2]oxa-phosphinine 6-oxide as starting phosphoramide and l,2-bis(benzo[d]thiazol-2-yl)disulfane as starting disulfide. Compound 4 was obtained with the yield of 61%. 'H NMR (500 MHz, CHLOROFORM-d) 5 ppm 4.11 - 5.55 (m, 2 H)Compound 6 was synthesized using general synthetic method described above using 6- (tert-butylamino)dibenzo[c,e][l,2]oxa-phosphinine 6-oxide as starting phosphoramide and disulfanediylbis(4,l-phenylene)-tetraethyl-bis(phosphate) (CAS No. 809-78-9) as starting disulfide. Compound 6 was obtained with the yield of 85 %. 'H NMR (500 MHz, CHLOROFORM-d) 5 ppm 1.29 (t, J=6.94 Hz, 6 H) 1.57 (br. s., 9 H) 3.91 - 4.31 (m, 4 H) 6.76 - 6.83 (m, 2 H) 6.90 (dd, J=8.85, 0.92 Hz, 2 H) 7.17 (s, 2 H) 7.21 - 7.98 (m, 6 H),31P NMR (202 MHz, CHLOROFORM-d) 5 ppm -6.26 (br. s., 1 P) 16.22 (br. s., 1 P) 19.05 (br. s., 1 P). HPLC-HRMS: composition found: C26H31NO6P2S.

[0179] Synthesis of compound 7 (with formula (li))Compound 7 was synthesized using general synthetic method described above using 6- (phenylamino)dibenzo[c,e][l,2]oxa-phosphinine 6-oxide as starting phosphoramide and l,2-bis(benzo[d]thiazol-2-yl)disulfane as starting disulfide. Compound 7 was obtained with the yield of 78%. 'H NMR (500 MHz, CHLOROFORM-d) 5 ppm 6.86 - 6.93 (m, 1 H) 7.05 - 7.16 (m, 3 H) 7.16 - 7.46 (m, 7 H) 7.60 (t, J=7.78 Hz, 1 H) 7.70 (dd, J=11.98, 8.16 Hz, 2 H) 7.76 - 7.90 (m, 2 H) 7.90 - 8.05 (m, 1 H),31P NMR (202 MHz, CHLOROFORM- d) 5 ppm 12.99 (br. s., 1 P),13C NMR (126 MHz, CHLOROFORM-d) 5 ppm 120.00 (d, J=8.17 Hz, 1 C) 121.15 (s, 1 C) 121.33 (s, 1 C) 122.16 (s, 1 C) 122.55 (s, 1 C) 122.71 (s, 1 C) 123.52 (d, J=11.81 Hz, 1 C) 124.55 (s, 1 C) 124.62 (s, 1 C) 124.94 (s, 1 C) 125.33 (s, 1 C) 126.17 (s, 1 C) 126.61 (s, 1 C) 127.26 (d, J=1.82 Hz, 2 C) 127.44 (s, 1 C) 128.38 (d, J=14.53 Hz, 1 C) 129.11 (s, 1 C) 130.39 (s, 1 C) 131.19 (d, J=9.08 Hz, 1 C) 133.76 (s, 1 C) 135.25 (s, 1 C) 136.17 (s, 1 C) 137.54 (d, J=6.36 Hz, 1 C) 139.20 (s, 1 C) 143.30 (d, J=5.45 Hz, 1 C) 150.25 (d, J=8.18 Hz, 1 C) 153.60 (s, 1 C) 154.56 (s, 1 C) 167.85 (s, 1 C) 170.65 (s, 1 C). HPLC-HRMS: composition found: C25H17N2O2PS2.

[0180] Synthesis of compound 8 (with formula ( I c)), , impact polystyrene (HIPS), or polyamide and the flame retardant compounds used in the examples and indicated in tables below were blended in a Haake mixer (60 rpm, 5 min) at210 °C, 160 °C and 290 °C, respectively. The polymer blends were then pelletized, and films (200 pm thick) were prepared by compression molding in a hot press. Pressing temperature was 190° C for PP, 165 °C for PS and 270 °C for PA-6.

[0183] The flame retardant efficacy was investigated in accordance to DIN 4102 B2 (edge ignition, flame length = 20 mm), UL 94 V standard or by determination of limited oxygen index. During the DIN 4102-B2 flammability test, the film was subjected to the flame for 15 seconds, whereafter the flame was removed, and the burning time was measured. From the burning tests the burning time and whether the standard was passed or failed. To pass the test, the flame was not allowed to exceed the 15 cm line within 20 seconds. Five film samples were produced and tested for each flame retardant formulation, if not otherwise stated.

[0184] In the following Tables “Formulation” stands for the test sample's composition, wherein PP means polypropylene, PA means polyamide 6, PS means polystyrene and HIPS high impact polystyrene. The number of the flame retardant compounds used is given as the number of the example in which it was prepared above or as the number of commercially available compound as previously listed. “Amount” refers to the amount of flame retardant compound(s) added to the reference material. The average burning time is calculated from the application of flame. The overall result for polymer films is given as Pass or Fail, according to the norm DIN 4102 B2 fire test. Low values of burning time reflects increased flame retardancy.

[0185] For UL94 V ratings the criteria shown in Table 1 was used.

[0186] Table 1. Criteria for UL94 V ratings.

[0187] Table 2 shows the test results for reference polypropylene (PP) films (without any flame retardant) and for combinations of PP films with various compounds as prepared in the examples above and some of commercially available compounds listed above. Table 2 also shows results from Din 4102-1 B2 tests of polystyrene and polyamide-6 films with or without the indicated compound (flame retardant). Table 3 shows the fire test results for polypropylene and polyamide 6 plaques, whereas in Table 4 the results of limited oxygen index measurements for polystyrene (PS) and high impact polystyrene (HIPS) have been summarised.

[0188] In Table 5 examples of successful preparation of flame retarded polystyrene prepared via suspension polymerization in the presence of the inventive flame retardants have been summarized. Moreover, expanded polystyrene has been prepared by extrusion using pentane as blowing agent with subsequent foaming in two stages.

[0189] Table 2. Din 4102-1 B2 test of polypropylene, polystyrene and polyamide-6 films of 200 pm thickness with or without a flame retardant compound.1The used polypropylene (PP) was LyondellBasell MOPLEN HP500N MFR (230 °C / 2.16 kg = 12 g / 10 min);2The used polystyrene (PS) was Styrolution PS 158N or GPPS 25SPI(LG Chemical);3The formulation was obtained by admixing compound 8 into the polymer melt of PS (i.e., not copolymerized with styrene);4The used polyamide was polyamide-6 (PA-6) = BASF PA6 Ultramid P3K;5Ref (PCO 900) = reference flame retardant(Aflammit PCO 900 (CAS no. 3001-98-7));62.5 wt-% of compound 1 and 5 wt-% of PCO900, respectively, based on the total weight of the formulation;7Ref A = reference flame retardant ((tert-butyl)( 10-oxo-9-oxa- 1 OiC-phosphaphcnan th r- 10-yl)amine) .

[0190] Table 2 shows flame retardant effects of the inventive flame retardants for polypropylene and polystyrene when used alone or in a synergistic combination with PCO 900 for polyamide-6.

[0191] Table 3. Polypropylene and polyamide-6 plaques of 1.6 mm and UL94 V ratings.1The used polypropylene (PP) was Moplen HP 552R (MFR 230 °C. / 2.16 kg =25 g / 10 min), PCO 900 = Aflammit PCO 900 (Thor GmbH, CAS no. 3001-98-7);25 wt-% of compound 1 and 10 wt-% of PCO 900, respectively, based on the total weight of the formulation31 wt-% of compound 1 and 30 wt-% of ATH, respectively, based on the total weight of the formulation;4The used polyamide (PA) was polyamide-6 (PA-6) = BASFPA6 Ultramid P3K,5LOI 21.4;6LOI 23,8.

[0192] In Table 4 the results of limiting oxygen index (LOI) values are shown for the various inventive flame retardant formulations.

[0193] Table 4. Flame retardant efficacy in terms of increased limited oxygen index values.1 The used polystyrene (PS) was Styrolution PS 158N or GPPS 25SPI (LG Chemical);2Emerald 3000 = Emerald Innovation 3000 (butadiene styrene brominated copolymer: CAS No. 1195978-93-8);32.4 wt-% of compound 1 and 0.4 wt-% of Emerald 3000,respectively, based on the total weight of the formulation;4The used high impact polystyrene (HIPS) was BASF polystyrol 454 KG2.

[0194] The increase in LOI values in the presence of the inventive flame retardants in comparison to the references (See Table 3), clearly shows that the inventive flame retardant compounds significantly increase the flame retardancy of polystyrene and high impact polystyrene when either used alone or in combination with conventional flame retardants, such as Emerald 3000.

[0195] Suspension polymerization of styrene in the presence of inventive flame retardantsThe suspension polymerizations were carried out in a 1 L jacketed (Buchi) steel autoclave reactor system equipped with an impeller stirrer. A circulating water bath controlled the reaction temperature within ± 0.3 °C. The reactor cover had inlets for addition of styrene, suspension agents and initiator. 92 mL of water, sodium acetate (1.58 mmol, 0.13 g) and styrene (720 mmol, 75 g) were added to the 1 L autoclave reactor. A part of the styrene (ca. 25 mL) was used to dissolve the flame retardant. At 50 °C, bentonite (0.900 mmol, 0.19 g), benzoyl peroxide (3.1 mmol, 0.76 g) and gelatin (0.38 g) in 15 mL water were added to the mixture at the stirring rate of 300 rpm. The polymerization was considered to have started when the reaction temperature reached 80 °C. After 30 minutes, the inventive flame retardant was charged into the reactor. The suspension polymerization was continued for an additional 5 h at 80 °C. Afterwards, the reactor was decanted, and the pearls were washed several times with water and then vacuum filtered. After drying the final product in a vacuum oven for 24 h at 40 °C, the pearls were analyzed. The suspension polymerization with polymerizable compound 8 was carried out in 100 mL round-bottom glass flask with magnetic stirring. The reaction flask was loaded with 18 mL of water, sodium acetate (0.32 mmol, 28 mg) and styrene (192 mmol, 20 g), compound 8 (1.9 mmol, 1 g), bentonite (95 mg), benzoyl peroxide (0.6 mmol, 150 mg) and gelatin (75 mg). The polymerization was conducted for 6 hours at 90 °C. Then the reaction mixture was filtered, and the precipitate was washed with water and then dried in a vacuum oven for 24 h at 40 °C prior the analyses.

[0196] Molecular weight results were obtained from SEC analysis by utilizing a HPSEC instrument equipped with Shimadzu LC-10ATVP pump and SEDERE SEDEX 85 LT -ELSD detector (Low Temperature Evaporative Light Scattering Detector).

[0197] Table 4. Polystyrene prepared by suspension polymerization in the presence or absence of compound (flame retardant) 1 or 8, and DIN4102 B2 fire test results of polystyrene films of 200 pm thickness.1The used polystyrene (PS) was Styrolution PS 158N or GPPS 25SPI (LG Chemical);2The formulation of PS and compound 8 was prepared by copolymerizing styrene and compound 8;3n.d = not determined.

[0198] Table 5. Particle size distribution of prepared polystyrene beads.1The used polystyrene (PS) was Styrolution PS 158N or GPPS 25SPI (LG Chemical).

[0199] Results of the suspension polymerizations (Table 4) showed no negative impact of the additives on the molecular weight of the prepared polystyrene. Furthermore, incorporation of the polymerizable compound 8 (flame retardant) to yield a polystyrene copolymer was successful, i.e., ' H NMR analysis confirmed the composition of the copolymer.

[0200] Surprisingly, the examples in according to the invention as shown in Tables 4 give very high flameproof already at very low loadings and no significant drop of polystyrene molecular weight or its distribution is observed in relative to polystyrene produced under same suspension polymerization conditions in absence of the inventive flame retardants. Moreover, it is surprising that also the bead size of polystyrene particles is not altered as shown in Table 5, i.e., the inventive compounds and polymers (flame retardants) do not negatively effect on suspension stability.

[0201] Another set of three experiments involving relevant steps for industrial production of expanded polystyrene (EPS), i.e., preparation of polystyrene beads containing pentane as blowing agent and utilizing the inventive compound (flame retardant) as the sole flame retardant was conducted.

[0202] The production of the polystyrene beads was done with twin-screw extruder KrausMaffei-Berstorff Ze25A x 49D UTX (KraussMaffei Berstorff GmbH, Laatzen, Germany) with a melt pump and melt cooler. A laboratory-scale underwater micropelletizing system ”LPU Laboratory Pelletizing System” (MAAG GALA, Eagle Rock, VA, USA) was connected to the melt cooler and used to make the expandable beads. Detailed trial parameters are in Table 2. Polywax 2000 (manufacturer Baker Hughes, low MW linear polyethylene with high crystallinity and low polydispersity) acted as the nucleating agent for the foam. The granulates and Polywax-additive were fed with onefeeder and the other additives with another feeder. The ’’zones” in Table 6 depict the heating zones of the extruder. After the trials the samples were put into cold storage until the date of the bead foaming trials.

[0203] Table 6. Parameters of the production of expandable beads in three experiments. The die holes in the die plate were divided into two clusters of five die holes.n.r = The value was not recorded.

[0204] The samples were pre-expanded, dried and stabilized overnight and steamchest moulded on 23.5. The pre-expansion was done in a laboratory-scale pre-expansion chamber. In the pre-expansion, 7.5 bar steam was used. The pre-expansion program is presented in Table 7.

[0205] Table 7. Parameters used in pre-expansion program.

[0206] The program has 2 halves. In the first half only the mixer moves, no steam. In the second half also steam comes through. The program was altered in real time during each trial point so that all the materials would rise to the same height in the chamber, effectively making their densities equal (in theory). The reference material height was used as the reference for the heights, the beads were expanded to visually about the same height in the chamber and the pre-expanded material densities were measured to be about 19 to 20 kg / m3.

[0207] The samples were dried and left to stabilize overnight. The steam-chest moulding was performed on THW 7010 (Thermoware, Barneveld, The Netherlands). The steam-chest moulding was done on the following program (Table 8), which was modified according to the sample.

[0208] Table 8. The steam-chest moulding program, for which the total steaming time was 7.5-8 seconds. The steam pressure was 3 bar during both preheating and steaming.

[0209] The efficacy of compound (flame retardant) 1 for expanded polystyrene was evaluated by measuring the limited oxygen index. The results are depicted in Table 9.

[0210] Table 9. Flame retarded expanded polystyrene (EPS) and limited oxygen index standard fire test results.1 The used polystyrene (PS) was Styrolution PS 158N or GPPS 25SPI (LG Chemical).

[0211] The results in Table 9 show that compounds (flame retardants) 1 and 2 significantly increase the flame retardancy of expanded polystyrene, since the limited oxygen index increased from 17.9 (ref) to 21.7 and 22.0, respectively.

[0212] While the forgoing examples are illustrative of the principles of the present invention in one or more particular applications, it will be apparent to those of ordinary skill in the art that numerous modifications in form, usage and details of implementation can be made without the exercise of inventive faculty, and without departing from the principles and concepts of the invention. Accordingly, it is not intended that the invention be limited, except as by the claims set forth below.

Claims

CLAIMS:

1. A compound of formula (I):formula (I), whereinR is selected from the group consisting of a Ci-20-alkyl, C2-2o-alkenyl, (CH2)m-Ce-2o- aryl, and a (CH2)m-Ci-2o-heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein m is an integer selected from 0- 2 and optionally the Ce-20-aryl and the Ci-20-heterocycle is substituted with 1-5 substituents each independently selected from R1; each R’ is independently selected from the group consisting of Ci-20-alkyl, C2-20- alkenyl, (CH2)n-Ce-20-aryl, SR, (CH2)n-C6-2o-arylene-C2-io-alkenyl, and a (CH2)n-Ci-2o- heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein n is an integer selected from 0-2 and optionally the Ce- 20-aryl and the (CH2)n-Ci-2o-heterocycle is substituted with 1-5 substituents each independently selected from R2;X is selected from the group consisting of a bond, NR’, N(R’)(R10), O, OR10, and R10, each optionally substituted with 1-5 substituents each independently selected from R3;X’ is selected from the group consisting of a bond, NR’, N(R’)(R10), O, OR10, and R10, each optionally substituted with 1-5 substituents each independently selected from R4;R” is selected from the group consisting of Ci-20-alkyl, (CH2)o-Ce-20-aryl, and SR, wherein o is an integer selected from 0-2 and optionally the Ci-20-alkyl and the (CH2)0-Ce- 20-aryl is substituted with 1-5 substituents each independently selected from R5;R’” is selected from the group consisting of Ci-20-alkyl, (CH2)P-Ce-2o-aryl, and SR, wherein p is an integer selected from 0-2 and optionally the Ci-20-alkyl and the (CH2)P-Ce- 20-aryl is substituted with 1-5 substituents each independently selected from R6; orR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle optionally substituted with 1-5 substituents each independently selected from R1; andeach R1, R2, R3, R4, R5, and R6is independently selected from the group consisting of Ci-io-alkyl, C2-io-alkenyl, (CH2)q-02C-C2-io-alkenyl, oxiran-2-yl, (CH2)q-SR7, (CH2)q- OR7, (CH2)q-N(R7)2, OP(O)(OR8)2 and -PO(R8)2, wherein q is an integer selected from 0-2, each R7is independently selected from the group consisting of H, Ci-io-alkyl, and C2-10- alkenyl, and each R8is independently selected from the group consisting of Ci-io-alkyl, C2-io-alkenyl, Ce-20-aryl, and OR9, wherein R9is selected from the group consisting of Ci-io-alkyl, C2-io-alkenyl, and Ce-20-aryl; and each R10is independently selected from the group consisting of a linear or branched Ci-6-alkylene, cyclic C3-io-alkylene, Ce-20-arylene, C?-24-alkarylene, and C?-24-arylalkylene.

2. A polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in claim 1, wherein the moiety is included in a main chain of the polymer, in a pendant group of the polymer or is part of a crosslink of the polymer.

3. The compound as claimed in claim 1 or the polymer as claimed in claim 2, wherein R is a Ci-20-heterocycle comprising 1-5 heteroatoms each independently selected from the group consisting of N, O, and S, wherein optionally the Ci-20-heterocycle is substituted with 1-5 substituents each independently selected from R1.

4. The compound as claimed in claim 1 or 3, or the polymer as claimed in claim 2 or 3, wherein R is a (CH2)m-C6-2o-aryl; and m is 0; optionally wherein the Ce-20-aryl is substituted with 1-5 substituents each independently selected from R1.

5. The compound or the polymer as claimed in any of the preceding claims, whereinR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle optionally substituted with 1-5 substituents each independently selected from R1.

6. The compound or the polymer as claimed in any of the preceding claims, whereinR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a mono- or polycyclic heterocycle comprising a phosphorous and 0-3 heteroatoms each independently selected from the group consisting of N, O, and S, optionally wherein the heterocycle is substituted with 1-5 substituents each independently selected from R1.

7. The compound or the polymer as claimed in any of the preceding claims, wherein X is O; andR’”, X’, R”, X, and the phosphorous both X’ and X are attached to together form a 5 - 14 membered mono-, bi- or tricyclic heterocycle comprising a phosphorus and an oxygen, optionally wherein the mono-, bi- or tricyclic heterocycle is substituted with 1-5 substituents each independently selected from R1.

8. The compound or the polymer as claimed in any of the preceding claims, whereinX is O; andR ', X', R ", X, and the phosphorous both X' and X are attached to together form a 14 membered tricyclic heterocycle comprising a phosphorus and an oxygen, optionally wherein the tricyclic heterocycle is substituted with 1-5 substituents each independently selected from R1.

9. The compound or the polymer as claimed in any of the preceding claims, whereinR’ is selected from the group consisting of tert-butyl, phenyl, and benzyl, optionally wherein the phenyl and benzyl is substituted with 1-3 substituents each independently selected from R2; andR2is selected from CH=CH2.

10. The compound as claimed in any of the claims 1, and 3 - 9, wherein the compound of formula (I) is selected from a compound of formula (la), (lb), (Ic), (Id), (le), (If), (Ig), (Ih), or (li):formula (lb) formula (Ic) formula (Id)formula (le) formula (If) formula (Ig) formula (Ih) formula (li)11. The polymer as claimed in any of claims 2 - 9, wherein the polymer is a copolymer or a terpolymer.

12. A composition comprising a compound of formula (I) and / or a polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in any of the preceding claims.

13. The composition as claimed in claim 12, wherein the composition further comprises one or more flame retardants.

14. Use of a compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in any of the preceding claims as a flame retardant or as a synergist with one or more flame retardants.

15. The use as claimed in claim 14, wherein the use of the compound of formula (I), the polymer comprising one or more repeating units and a moiety of a compound of formula (I), or the composition is as a flame retardant for a synthetic or natural polymer, wherein the synthetic and natural polymer is selected from foamed polystyrene, such as expanded polystyrene (EPS), extruded polystyrene (XPS), foam sheets prepared from homopolymeric polystyrene or co- / terpolymers of polystyrene.

16. A method for producing molding compounds, wherein the method comprises: a) providing a melt composition comprising a polymer melt comprising at least one compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in any of claims 1 - 13, wherein the temperature of the melt composition is at least 120 °C; b) discharging the melt composition through a nozzle plate having one or more holes; and c) granulating the discharged melt composition.

17. The method for producing molding compounds as claimed in claim 16, wherein the method comprises, before a), mixing an organic blowing agent with the polymer melt at a temperature of at least 150 °C; and, before b), cooling the melt composition to a temperature of at least 120 °C.

18. A method for producing molding compounds, wherein the method comprises: a) polymerizing a first composition comprising a compound of formula (I) or a polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in any of claims 1 - 13, optionally in the presence of one or more vinylic monomers, to form a first polymer; b) optionally adding before, during, and / or after the polymerizing in a) one or more of an organic blowing agent, suspension agent, and nucleating agent, or a combination thereof to the first composition or to the formed first polymer; and c) separating the formed first polymer.

19. A molding compound obtainable by a method as defined in any of claims 16 - 18.

20. Use of a compound of formula (I), a polymer comprising one or more repeating units and a moiety of a compound of formula (I), or a composition as defined in any of claims 1 - 13 as an individual component or co-component of insulating material for buildings or as a part and / or component in electrical devices, or in polymer extrusion or in polymerization processes.

21. A method for the preparation of a compound of formula (I) as defined in any of claims 1, and 3 - 10, wherein the method comprises n composition comprising a compound of formula (X):formula (X), whereinX, X’, R’, R”, and R’” are as defined in claim 1; and a base, thereby deprotonating the nitrogen of the compound of formula (X); ii) optionally heating the reaction composition; iii) adding to the reaction composition a compound of formula (XII):R-S-X’” formula (XII), whereinR is as defined in claim 1 ; andX’” is a leaving group, thereby forming a compound of formula (I):formula (I), whereinX, X’, R, R’, R”, and R’” are as defined in claim 1.

22. A method for the preparation of a polymer comprising one or more repeating units and a moiety of a compound of formula (I), as defined in any of the claims 2 - 9 and 11, wherein the method comprises: i) providing a reaction composition comprising a compound of formula (I):formula (I), whereinX, X’, R, R’, R”, and R’” are as defined in claim 1; and optionally one or more monomers; ii) optionally heating the reaction composition, thereby forming the polymer comprising one or more repeating units and a moiety of a compound of formula (I) as defined in any of claims 2 - 9 and 11.

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