Flame retardant compounds, compositions, methods, and uses thereof

Abstract

There is provided herein, a fire-retardant complex compound including a positively charged melamine-containing polymer bound to a negatively charged borate- and / or phosphate- polymer. There are further provided herein, methods of producing the fire-retardant compound, compositions, and uses thereof.

Description

[0001] FLAME RETARDANT COMPOUNDS, COMPOSITIONS, METHODS, AND USES THEREOF

[0002] TECHNICAL FIELD

[0003] The present disclosure relates to the field of flame-retardant materials. More specifically, the disclosure relates to flame-retardant compounds, compositions, uses, and methods of producing thereof.

[0004] BACKGROUND

[0005] Flame-retardant or fire-retardant (FR) compounds are substances added to manufactured products in order to reduce the risk of damage caused by fire. These compounds are applied to the products to minimize the probability of harm to humans, property, or the environment. The products can be made of polymer, wood, or textiles. The FR compound can be added as a raw material or as part of a composition that can be incorporated by impregnation, coating, or as a part of the product manufacturing process, such as in a master batch. By certain physical and chemical mechanisms, the added compound can prevent burning or slow the spread of a fire in the designated manufactured product.

[0006] There are several ways to reduce the flammability of materials. One mechanism is known as 'endothermic degradation'. This refers to the energy required for compounds to break down when exposed to high temperatures, such as in a flame. Another mechanism is called 'thermal shielding' (i.e., solid phase flame retardancy), which involves creating a thermal insulating barrier between the burning and unbumed parts by turning the polymer surface into a char. A third example is 'gas phase dilution', in which inert gases, such as carbon dioxide, ammonia, and water, are produced via thermal degradation. These gases act as diluents for the combustible gases, reducing the partial pressure of oxygen and slowing the reaction rate. Different flame retardant compounds have their own unique mechanisms of action, determined by their chemical structures. A compound's flame retardation effect can involve one or more mechanisms.

[0007] Melamine is a type of FR that contains a high percentage of nitrogen and does not contain halogens. When melamine undergoes thermal decomposition, it produces inert gases such as NH3 and dilutes the combustible gases in the system to achieve the effect of flame retardation. However, despite its potential, a FR compound based on melamine has some issues such as low degradation temperature, sublimation, leeching, or bleeding during processing or out of the surface of the final product. The melamine moiety alone is not sufficient motif by itself to provide flame retardation through several dominant mechanisms of action.

[0008] In addition, melamine is only slightly water soluble, which makes it challenging to include in water-based FR compositions. Hence, compositions that rely on melamine are not stable enough to remain homogeneously dispersed during the necessary processing time to implement the FR composition into a designated product.

[0009] Accordingly, there is a need in the art for multi-mechanism-dominant and highly incorporative melamine-based compounds that can retard flame more efficiently and that can be incorporated well in a manufactured product.

[0010] SUMMARY

[0011] The disclosure is directed, in embodiments thereof, to a flame-retardant (FR) compound including a melamine-based positively charged polymer complexed with a phosphate- and / or borate-based negatively charged polymer(s).

[0012] According to some embodiments, the advantageous FR compound may be utilized in products, such as plastic, wood, textiles, surface finishes, or coatings. Advantageously, in some embodiments, a flame / fire can be suppressed, prevented, and / or delayed at the designated manufactured product upon an inclusion of the FR compound provided herein.

[0013] According to some embodiments, the FR compound may inherently adapt multiple mechanisms of action to retard fire owing to its chemical structure. These may include, in accordance with some embodiments, but are not limited to, endothermic degradation, thermal shielding (via char formation towards solid phase flame retardancy), and gas phase dilution. In some embodiments, the compound includes numerous melamine that potentially can undergo through a gas phase dilution mechanism of retardation. In other embodiments, the compound includes numerous covalently bound monomeric units that potentially may act via a mechanism of endothermic degradation. In additional embodiments, the compound including a complex of electrostatically bound positively and negatively charged polymers may act via an additional endothermic degradation mechanism of retardation. In yet other embodiments, the compound incorporates multiple units of phosphate which may act via thermal shielding retardation mechanism.

[0014] According to some embodiments, the FR compound is advantageous as it incorporates well into FR compositions and / or manufactured products. In some embodiments, a dispersion of FR composition, typically based on water, remains stable upon the incorporation of the FR compound. In fact, the stability of the dispersion is demonstrated for the required duration of handling and / or manufacturing, in accordance with some embodiment, which makes the overall processing more efficient. According to some embodiments, this stable aqueous dispersion is attributed to the highly polar FR complex compound induced by the multiple charged moi eties. The complex structure, including the electrostatically bound positively and negatively charged polymers, enables the incorporation of high molecular weight molecules, which are otherwise characterized as hydrophobic molecules by nature and may not be included in water compositions, according to some embodiments.

[0015] In additional embodiments, there is provided herein an advantageous method for producing the FR compound. According to some embodiments, the production method involves a chemical complexation that benefits from a solid-state chemical reaction. In some embodiments, the production is facilitated by a by-production of ammonia gas.

[0016] There is provided, in accordance with some embodiments, a compound represented by formula (I): wherein: Z is Ci-Cis alkylene, wherein W is Ci-Cis alkylene; e and q are integers from 1-1000;

[0017] [A'] is represented by formula (CI-1): ination thereof.

[0018] (CI-2)

[0019] According to some embodiments, a compound represented by formula (I) is a neutral compound.

[0020] According to some embodiments, a compound represented by formula (I) is capable of being homogeneously dispersed in a polar protic solvent. In some embodiments, the solvent includes water.

[0021] According to some embodiments of formula (I), the dispersion in the polar protic solvent is stable for at least about 60 hours at room temperature.

[0022] According to some embodiments of formula (I), Z is and the compound is represented by the structure:

[0023] (Compound I)

[0024] According to some embodiments of formula wherein W and the compound is represented by the structure:

[0025] (Compound II)

[0026] According to some embodiments, the compound of formula (I) is for use as a fire retardant. According to some embodiments, the compound of formula (I) is characterized by a decomposition temperature of at least about 350°C at 25% (w / w) mass loss (Td2s), and of at least about 400°C at 50% (w / w) mass loss (Tdso) upon heating the compound at a heating rate of 20 °C / min under a nitrogen flow of 60 ml / min. According to some embodiments, when incorporated in textile or plastic material in an amount of at least about 5% (w / w), the compound represented by formula (I) facilitates passing a standard flaming test.

[0027] According to some embodiments, a compound represented by formula (I) facilitates passing a standard flaming test ASTM D6413 / D6413M, when incorporated in a textile in an amount of between about 5% and about 50% (w / w).

[0028] There is provided, in accordance with some embodiments, a compound represented by formula (II):

[0029] (Formula II) wherein:

[0030] X is absent, or is selected from C1-C20 hydrocarbylene, wherein Y is a C1-C20 hydrocarbylene; e and n are integers from 1-1000; n2is an integer from 1-100; and

[0031] [A'] is represented by formula (CI-1): ination thereof.

[0032] (CI-2)

[0033] According to some embodiments, the compound represented by formula (II) is a neutral compound.

[0034] According to some embodiments, the compound of formula (II) is capable of being homogeneously dispersed in a polar protic solvent. In some embodiments, the solvent includes water.

[0035] According to some embodiments, the dispersion in the polar protic solvent is stable for at least about 60 hours at room temperature.

[0036] According to some embodiments of formula (II), X is absent, and the compound is represented by the structure:

[0037] (Compound III) According to some embodiments of formula ( the compoundsented by the structure:

[0038] (Compound IV)

[0039] According to some embodiments of formula (

[0040] In some embodiments, is

[0041] , and the compound is represented by the structure:

[0042] (Compound V) In some embodiments of formula (II), and Y is

[0043] , and the compound is represented by the structure:

[0044] (Compound VI)

[0045] In some embodiments of formula (II), and Y is and the compound is represented by the structure:

[0046] (Compound VII) In some embodiments of formula (II), and Y is and the compound is represented by the structure:

[0047] (Compound VIII)

[0048] In some embodiments of formula ( the compound is represented by the structure:

[0049] (Compound IX) According to some embodiments, the compound of formula (II) is for use as a fire retardant.

[0050] According to some embodiments of formula (II), the compound is being characterized by a decomposition temperature of at least about 350°C at 25% (w / w) mass loss (Td2s), and at least about 400°C at 50% (w / w) mass loss (Tcho) upon heating the compound at a heating rate of 20 °C / min under a nitrogen flow of 60 ml / min.

[0051] According to some embodiments, when incorporated in textile or plastic material in an amount of at least 5%, the compound of formula (II) facilitates passing a standard flaming test (such as ASTM D6413 / D6413M or UL-94).

[0052] There is provided, in accordance with some embodiments, a method of producing a compound of formula (I) or (II), the method includes: providing a first component, wherein the first component is represented by formula (I-N):

[0053] (Formula I-N) wherein:

[0054] Z is Ci-Cis alkylene, wherein W is Ci-Cis alkylene; and q is an integer from 1-1000; or wherein the first component is represented by formula (II-N):

[0055] X is absent, or is selected from C1-C20 hydrocarbylene, O wherein Y is C1-C20 hydrocarbylene; n is an integer from 1-1000; and n2is an integer from 1-100; providing a second component of formula (CI-l-N): bination thereof;

[0056] (CI-2-N) wherein: e is an integer from 1-1000; and

[0057] G+is a cationic counter ion; mixing the first and the second components to obtain a mixture; and heating the mixture to produce the compound disclosed herein.

[0058] According to some embodiments, G+is NH4+and / or melaminium.

[0059] According to some embodiments, the obtained mixture is a powder.

[0060] According to some embodiments, the mixing is initiated in a solid phase.

[0061] According to some embodiments, the mixing is performed by using a technique selected from: ball-milling, mortar and pestle, grinding, melting, pelleting, and any combination thereof.

[0062] According to some embodiments, the mixture is supplemented with an acid.

[0063] According to some embodiments, the heating is performed at a temperature of at least about 150 °C. There is provided, in accordance with some embodiments, a compound produced according to the herein disclosed method.

[0064] According to some embodiments, the compound produced by the herein disclosed method is represented by formula (I):

[0065] (Formula I) wherein:

[0066] Z is Ci-Cis alkylene, wherein W is Ci-Cis alkylene; e and q are integers from 1-1000;

[0067] [A'] is represented by formula (CI-1): mbination thereof.

[0068] (CI-2)

[0069] According to some embodiments, the compound produced by the herein disclosed method is represented by formula (II):

[0070] (Formula II) wherein: is absent, or is selected from C1-C20 hydrocarbylene, o wherein Y is a C1-C20 hydrocarbylene; e and n are integers from 1-1000; n2is an integer from 1-100; and

[0071] [A'] is represented by the formula (CI-1): ination thereof.

[0072] (CI-2)

[0073] According to some embodiments, the compound produced by the herein disclosed method is capable of being homogeneously dispersed in a polar protic solvent.

[0074] According to some embodiments, the compound produced by the herein disclosed method is characterized by a decomposition temperature of at least about 350°C at 25% (w / w) mass loss (Td2s), and at least about 400°C at 50% (w / w) mass loss (Tdso) upon heating the compound at a heating rate of 20 °C / min under a nitrogen flow of 60 ml / min. According to some embodiments, when incorporated in a textile or plastic material in an amount of at least about 5% (w / w), the compound produced by the herein disclosed method facilitates passing a standard flaming test.

[0075] There is provided, in accordance with some embodiments, use of the herein disclosed compound of formula (I) and II) as a flame-retardant compound in paint, coating, plastic, textile, and / or impregnation.

[0076] According to some embodiments, the impregnation is in wood, concrete, and / or textile.

[0077] There is provided, in accordance with some embodiments, a use of the herein disclosed compound of formula (I) and II) as a flame-retardant compound in a plastic material.

[0078] There is provided, in accordance with some embodiments, a flame-retardant composition including the herein disclosed compound, and an acceptable fire-retardant carrier, in a suitable amount, the composition being formulated for incorporation in textiles.

[0079] According to some embodiments, the composition disclosed herein includes a polar solvent. In some embodiments, the polar solvent is or includes water.

[0080] There is provided, in accordance with some embodiments, a flame-retardant composition including the herein disclosed compound, and an acceptable fire-retardant carrier, in a suitable amount, the composition being formulated for incorporation in plastic material.

[0081] According to some embodiments, the herein disclosed composition is stable for at least about 60 hours at room temperature.

[0082] According to some embodiments, the herein disclosed composition further includes another fire retardant.

[0083] There is provided, in accordance with some embodiments, a flame retarded plastic material including the compound disclosed herein, optionally in combination with other flame retardants.

[0084] There is provided, in accordance with some embodiments, a textile article of manufacture made of or coated with the compound disclosed herein, optionally in combination with other flame retardants. Certain embodiments of the present disclosure may include some, all, or none of the above advantages. One or more technical advantages may be readily apparent to those skilled in the art from the figures, descriptions and claims included herein. Moreover, while specific advantages have been enumerated above, various embodiments may include all, some or none of the enumerated advantages.

[0085] In addition to the exemplary aspects and embodiments described above, further aspects and embodiments will become apparent by reference to the figures and by study of the following detailed descriptions.

[0086] BRIEF DESCRIPTION OF THE FIGURES

[0087] Some embodiments of the disclosure are described herein with reference to the accompanying figures. The description, together with the figures, makes apparent to a person having ordinary skill in the art how some embodiments may be practiced. The figures are for the purpose of illustrative description and no attempt is made to show structural details of an embodiment in more detail than is necessary for a fundamental understanding of the disclosure. For the sake of clarity, some objects depicted in the figures are not to scale.

[0088] In the figures:

[0089] FIGURE 1 - shows a flowchart of steps of a method for producing a fire-retardant compound, according to some embodiments;

[0090] FIGURE 2 - shows a thermal gravimetric analysis (TGA) plot for poly(melamine-co-oxalyl) (starting material II-N-IV), acquired while heating the sample from 30 °C - 400 °C at a heating rate of 20 °C / min, under a nitrogen flow of 60 ml / min, according to some embodiments;

[0091] FIGURE 3 - shows a thermal gravimetric analysis (TGA) plot for poly(melamine-co-oxalyl) tetraborate complex (compound IV-CI-1), acquired while heating the sample from 30 °C - 600 °C at a heating rate of 20 °C / min, under a nitrogen flow of 60 ml / min, according to some embodiments;

[0092] FIGURE 4 - shows a thermal gravimetric analysis (TGA) plot for poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2), acquired while heating the sample from 30 °C - 600 °C at a heating rate of 20 °C / min, under a nitrogen flow of 60 ml / min, according to some embodiments; FIGURE 5 - shows a thermal gravimetric analysis (TGA) plot for poly(melamine-co-oxalyl) tetraborate polyphosphate complex (compound IV-CI-1-2), acquired while heating the sample from 30 °C - 600 °C at a heating rate of 20 °C / min of 60 ml / min, under a nitrogen flow, according to some embodiments;

[0093] FIGURE 6 - shows an ASTM D6413 / D6413M analysis report for the flammability resistance of a fabric of polyester / cotton (1 : 1) incorporating poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2), according to some embodiments;

[0094] FIGURE 7 - shows an ASTM D6413 / D6413M analysis report for the flammability resistance of a fabric of cotton incorporating poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2), according to some embodiments;

[0095] FIGURE 8 - shows an ASTM D6413 / D6413M analysis report for the flammability resistance of a fabric of polyester / cotton (1 : 1) incorporating melamine-functionalized polysiloxane polyphosphate complex (compound I-CI-2), according to some embodiments;

[0096] FIGURE 9 - shows an ASTM D6413 / D6413M analysis report for the flammability resistance of a fabric of cotton incorporating melamine-functionalized polysiloxane polyphosphate complex (compound I-CI-2), according to some embodiments;

[0097] FIGURE 10- shows an ASTMD6413 / D6413M analysis report for the flammability resistance of a fabric of polyester incorporating poly(melamine-co-urea) polyphosphate complex (compound VII-CI-2), according to some embodiments;

[0098] FIGURE 11 - shows an ASTMD6413 / D6413M analysis report for the flammability resistance of a fabric of cotton incorporating poly(melamine-co-urea) polyphosphate complex (compound VII-CI-2), according to some embodiments;

[0099] FIGURE 12- shows an ASTMD6413 / D6413M analysis report for the flammability resistance of a fabric of cotton incorporating poly(melamine-co-oxalyl) (starting material II-N-IV), according to some embodiments;

[0100] FIGURE 13- shows an ASTMD6413 / D6413M analysis report for the flammability resistance of a fabric of polyester incorporating poly(melamine-co-oxalyl) (starting material II-N-IV), according to some embodiments; FIGURE 14 - shows a photograph of ABS polymer extrudate incorporating poly(melamine- co-oxalyl) (starting material II-N-IV) upon extrusion, according to some embodiments;

[0101] FIGURE 15 - shows a photograph of ABS polymer extrudate incorporating poly(melamine- co-oxalyl) polyphosphate complex (compound IV-CI-2) upon extrusion, according to some embodiments;

[0102] FIGURE 16 - shows a photograph of ABS polymer grains incorporating poly(melamine-co- oxalyl) (starting material II-N-IV), according to some embodiments;

[0103] FIGURE 17 - shows a photograph of ABS polymer grains incorporating poly(melamine-co- oxalyl) polyphosphate complex (compound IV-CI-2), according to some embodiments;

[0104] FIGURES 18A-B - show UL-94 vertical burning test analysis report for 3.2 mm ABS plastic sticks, which incorporated poly(melamine-co-oxalyl) polyphosphate complex compound (compound IV-CI-2), according to some embodiments; FIGURE 18A shows the performance specification, and FIGURE 18B shows the requirements for each criterion condition;

[0105] FIGURE 19 - shows UL-94 horizontal burning test analysis report for 1.6 mm ABS plastic sticks, which incorporated poly(melamine-co-oxalyl) polyphosphate complex compound (compound IV-CI-2), according to some embodiments;

[0106] FIGURE 20 - shows UL-94 horizontal burning test analysis report for 1.6 mm ABS plastic sticks, which incorporated melamine-functionalized polysiloxane polyphosphate complex compound (compound I-CI-2), according to some embodiments; and

[0107] FIGURE 21 - shows UL-94 horizontal burning test analysis report for 3.2 mm ABS plastic sticks, which incorporated poly(melamine-co-oxalyl) tetraborate complex compound (compound IV-CL1), according to some embodiments.

[0108] DETAILED DESCRIPTION

[0109] In the following description, various aspects of the disclosure will be described. For the purpose of explanation, specific configurations and details are set forth in order to provide a thorough understanding of the different aspects of the disclosure. However, it will also be apparent to one skilled in the art that the disclosure may be practiced without specific details being presented herein. Furthermore, well-known features may be omitted or simplified in order not to obscure the disclosure.

[0110] Prior to setting forth the present subject matter in detail, it may be helpful to provide definitions of certain terms to be used herein. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this subject matter pertains. The following definitions are provided for clarity.

[0111] The term "a" or "an" as used herein includes the singular and the plural, unless specifically stated otherwise. Therefore, the terms "a," "an", "at least one", or “at least two” can be used interchangeably in this application.

[0112] As used herein, the verb "comprise" as is used in this description and in the claims and its conjugations are used in its non-limiting sense to mean that items following the word are included, but items not specifically mentioned are not excluded.

[0113] As used herein, the term "about" when used in connection with a numerical value includes ±10% from the indicated value. In addition, all ranges directed to the same component or property herein are inclusive of the endpoints, are independently combinable, and include all intermediate points and ranges. It is understood that where a parameter range is provided, all integers within that range, and tenths thereof, are also provided by the invention.

[0114] As used herein, in accordance with some embodiments, the term “fire retardant” or “flame retardant” refers to a substance, material or composition designed to reduce the flammability of other associated materials, inhibit the ignition and spread of fire, and enhance fire safety by slowing down the combustion process.

[0115] As used herein, in accordance with some embodiments, the term “thermogravimetric analysis (TGA)” refers to a method of thermal analysis in which the mass of a sample is measured over time as the temperature is elevated. TGA can be used to evaluate the thermal stability of a material.

[0116] As used herein, in accordance with some embodiments, the term “decomposition temperature (Tdx)” refers to the temperature at which a material chemically decomposes and loses X % (w / w) of its mass, for example, a value of Td25 indicates the temperature at which the material loses 25% of its initial mass weight, at a defined TGA experimental conditions. Td is expressed in units of degrees Celsius (°C). This parameter determines the thermal survivability of the material, according to some embodiments.

[0117] As used herein, in accordance with some embodiments, the term “ASTM analysis / method / test” refers to a standardized test by the American Society for Testing and Materials. For example, a suitable ASTM to determine a fire retardant activity may be ASTM D6413 / D6413M, UL-94, or others.

[0118] As used herein, in accordance with some embodiments, the terms “wettability” and “water-compatibility” refers to the ability of water to maintain contact with a solid surface of the herein-detailed compound. In some embodiments, the (direct or indirect) water compatibility characteristic of a compound induces stability of a polar medium, which includes water and / or other polar media, in which the compound is dispersed.

[0119] As used herein, in accordance with some embodiments, the term “complex” refers to the association compound formed between oppositely charged oligomer and / or polymer entities. According to some embodiments, the complex is formed by an electrostatic interaction between oppositely charged polyionic oligomer and / or polymer, as well as other optional polar interactions. According to some embodiments, the oligomer and / or polymer can be organic, inorganic, or a combination thereof.

[0120] As used herein, in accordance with some embodiments, the term “polysiloxane” refers to a polymer consisting of a silicon-oxygen repeating unit backbone. In some embodiments, an organic group, e.g. melamine-containing substituent, is intermittently or periodically bound to the silicone element.

[0121] As used herein, in accordance with some embodiments, the term “counter ion” refers to a small molecule ion or a metal ion that accompanies an ionic species in order to maintain electric neutrality of the whole compound. In some embodiments, the counter ion may be referred to as an anion or a cation, depending on whether it is negatively or positively charged. Thus, in accordance with some embodiments, the counterion to an anion will be a cation, and vice versa. As used herein, in accordance with some embodiments, the terms “solid-state synthesis”, “solid-state reaction”, “solid-phase synthesis”, or “solid-phase reaction” refer to a chemical reaction from solid starting materials to form a new powder / solid compound.

[0122] As used herein, in accordance with some embodiments, the term “C1-C20 hydrocarbylene” refers to a hydrocarbon diradical of from 1 to 20 carbon atoms, in which each hydrocarbon diradical is aromatic or non-aromatic, saturated or unsaturated, straight chain or branched chain, cyclic (having three carbons or more, and including mono- and poly-cyclic, fused and non-fused polycyclic, and bicyclic) or acyclic., and substituted by one or more substituents or unsubstituted.

[0123] As used herein, in accordance with some embodiments, the term “alkyl” group refers to any saturated aliphatic hydrocarbon, including straight-chain and branched-chain alkyl groups. Non-limiting examples of alkyl groups include straight, branched, and cyclic alkyl groups. An alkyl group can be, for example, a Ci, C2, C3, C4, C5, Ce, C7, Cs, C9, C10, Cu, C12, C13, C14, C15, Ci6, C17, Cis, C19, or C20, group that is substituted or unsubstituted. Non-limiting examples of straight alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, docosyl, and the like. Branched alkyl groups include any straight alkyl group substituted with any number of alkyl groups.

[0124] As used herein, in accordance with some embodiments, the term “alkylene" or "alkylene chain" refers to a straight or branched divalent hydrocarbon chain linking the rest of the molecule through a radical group, for example, methylene, ethylene, propylene, n-butylene, and the like. The alkylene chain is attached to the rest of the molecule through a single bond and to the radical group through a single bond. The points of attachment of the alkylene chain to the rest of the molecule and to the radical group is through one carbon in the alkylene chain or through any two carbons within the chain.

[0125] As used herein, in accordance with some embodiments, the term “alkenyl” group refers to any unsaturated aliphatic hydrocarbon, including at least one carbon-carbon double bond. An alkenyl group can be, for example, a C2, C3, C4, C5, Ce, C7, Cs, C9, C10, Cu, C12, C13, C14, C15, Cie, C17, Cis, C19, or C20, group that is substituted or unsubstituted.

[0126] As used herein, in accordance with some embodiments, the term "alkenylene" or "alkenylene chain" refers to a straight or branched divalent hydrocarbon chain linking the rest of the molecule to a radical group, containing at least one carbon-carbon double bond. The alkenylene chain is attached to the rest of the molecule through a single bond and to the radical group through a single bond. The alkenylene group can be substituted or unsubstituted.

[0127] As used herein, in accordance with some embodiments, the term “alkyne” refers to a straight or branched hydrocarbon chain, containing at least one carbon-carbon double bond, and having from two to twenty carbon atoms. The alkyne chain is attached to the rest of the molecule through a single bond and to the radical group through a single bond. The alkyne group can be substituted or unsubstituted.

[0128] As used herein, in accordance with some embodiments, the term "alkynylene" or "alkynylene chain" refers to a straight or branched divalent hydrocarbon chain linking the rest of the molecule to a radical group, containing at least one carbon-carbon triple bond, and having from two to twenty carbon atoms. The alkynylene chain is attached to the rest of the molecule through a single bond and to the radical group through a single bond. The alkynylene group can be substituted or unsubstituted.

[0129] As used herein, in accordance with some embodiments, the term “cycloalkyl” group refers to a saturated or unsaturated cyclic hydrocarbon, including monocyclic or polycyclic groups. Non-limiting examples of cyclic alkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Cyclic alkyl groups also include fused-, bridged-, and spiro-bicycles and higher fused-, bridged-, and spiro-systems.

[0130] As used herein, in accordance with some embodiments, the term “cycloalkylene” group refers to a divalent saturated or unsaturated cyclic hydrocarbon, linked to the rest of the molecule through a radical group. The cycloalkylene is attached to the rest of the molecule through a single bond and to the radical group through a single bond. The cycloalkylene group can be substituted or unsubstituted.

[0131] As used herein, in accordance with some embodiments, the term “aryl” group refers to an aromatic carbocyclic group. An aryl group can be monocyclic or polycyclic. Non-limiting examples of aryl groups include phenyl, toluyl, naphthyl, pyrrolyl, pyridyl, imidazolyl, thiophenyl, and furyl. Non-limiting examples of substituted aryl groups include phenyl, phenyl, naphthyl including 1 -naphthyl and 2-naphthyl.

[0132] As used herein, in accordance with some embodiments, the term “arylene” group refers to a divalent aromatic carbocyclic group, linked to the rest of the molecule through a radical group. The arylene is attached to the rest of the molecule through a single bond and to the radical group through a single bond. The arylene group can be substituted or unsubstituted.

[0133] As used herein, in accordance with some embodiments, one or more moieties described herein can contain heteroatoms. The heteroatoms may include at least one element of nitrogen, oxygen, sulfur, or any combination thereof.

[0134] As used herein, in accordance with some embodiments, one or more moieties described herein can be substituted or unsubstituted. According to some embodiments, non-limiting examples of optional substituents include hydroxyl groups, sulfhydryl groups, halogens, amino groups, nitro groups, nitroso groups, cyano groups, azido groups, sulfoxide groups, sulfone groups, sulfonamide groups, carboxyl groups, carboxaldehyde groups, imine groups, alkyl groups, halo-alkyl groups, alkenyl groups, halo-alkenyl groups, alkynyl groups, halo-alkynyl groups, alkoxy groups, aryl groups, aryloxy groups, aralkyl groups, arylalkoxy groups, heterocyclyl groups, acyl groups, acyloxy groups, carbamate groups, amide groups, ureido groups, epoxy groups, and ester groups. Other non-limiting examples of optional substituents include halogen, haloalkyl, hydroxy, alkoxy, haloalkoxy, cycloalkyl, aryl, heterocyclyl, heteroaryl, amido, alkylamido, dialkylamido, nitro, amino, cyano, azido, oxo, alkylamino, dialkylamino, carboxyl, thio, thioalkyl and thioaryl.

[0135] According to some embodiments, compounds described herein can contain an asymmetric atom (also referred as a chiral center), and some of the compounds can contain one or more asymmetric atoms or centers, which can thus give rise to optical isomers (enantiomers) and diastereomers. The present teachings and compounds disclosed herein include such enantiomers and diastereomers, as well as the racemic and resolved, enantiomerically pure R and S stereoisomers, as well as other mixtures of the R and S stereoisomers and pharmaceutically acceptable salts thereof. Optical isomers can be obtained in pure form by standard procedures known to those skilled in the art, which include, but are not limited to, diastereomeric salt formation, kinetic resolution, chiral separation by HPLC, simulated moving bed chromatography (SMB), and asymmetric synthesis. The present teachings also encompass cis and trans isomers (Z and E) of compounds containing alkenyl moieties (e.g., alkenes and imines). It is also understood that the present teachings encompass all possible regioisomers, and mixtures thereof, which can be obtained in pure form by standard separation procedures known to those skilled in the art, and include, but are not limited to, column chromatography, thin-layer chromatography, and high-performance liquid chromatography. There is provided herein, in accordance with some embodiments, a compound represented by formula (I):

[0136] (Formula I) wherein:

[0137] Z is Ci-Cis alkylene, wherein W is Ci-Cis alkylene; e and q are integers from 1-1000;

[0138] [A'] is represented by formula (CI-1): ination thereof.

[0139] (CI-2) According to some embodiments of formula (I), the compound is neutral.

[0140] According to some embodiments of formula (I), when [A ']eis represented by (CI-1), 2 x q = e. According to some embodiments, when [A ']eis represented by (CI-1), e = q.

[0141] According to some embodiments of formula (I), when [A ']eis represented by (CI-2), q = 2 x e. According to some embodiments, when [A ']eis represented by (CI-2), e = q.

[0142] According to some embodiments of formula (I), the charge is single or double, delocalized at the melamine moiety, and the formula may be further represented by formula (I’), (1(2+)), (I’(2+)), or any tautomer thereof.

[0143] (Formula F(2+))

[0144] According to some embodiments, n and q are each independently integers from: 5-200, 100-200, 100-500, 200-300, 300-400, 400-500, 100-700, 500-600, 600-700, 700-800, 800-900, and 900-1000. Each possibility is a separate embodiment. T1

[0145] According to some embodiments, formula (I) represents a compound of a complex. According to some embodiments, the complex includes a polysiloxane functionalized with a positively charged melamine moiety complexed together with a negatively charged inorganic polymer (CI-1), (CI-2), or a combination thereof. In some embodiments, the complex includes cross-linked polymers. In some embodiments, the complex includes partially cross-linked polymers. In some embodiments, the cross-linking of the polymers is induced by polar and / or electrostatic interactions between the oppositely charged polymers and / or oligomers. In some embodiments, the cross-linking of the polymers is induced by the structure of the polymer and / or oligomer neutral starting materials.

[0146] According to some embodiments of formula (I), the polysiloxane includes repeating units of SiCh array. According to some embodiments of formula (I), the polysiloxane is a three- dimensional network of -O-Si-O- repeating moieties further bound to positively charged melamine moieties through the Si. According to some embodiments, the polysiloxane is a bulk silica. In some embodiments, the polysiloxane may be an amorphous silica. In some embodiments, the polysiloxane may be partially amorphous silica and partially crystalline.

[0147] According to some embodiments, a symbol “ ”, as detailed in formula (I), denotes the point(s) of attachment of a radical to a defined portion(s) of the compound. In some embodiments of formula (I), the symbol denotes the point(s) of attachment of Si or O atoms of one monomer to consecutive Si or O atoms of another monomer.

[0148] In other embodiments, the symbol “ ”, as detailed in formula (I), denotes the point(s) of attachment of an organic substituent radical to a defined organic portion(s) radical of the compound. In some embodiments, the organic portion(s) radical refers to any Ci-Cis alkylene, for example, , i.e. C3H6.

[0149] According to some embodiments, Z is Ci-Cis alkylene, or W is Ci-Cis alkylene, according to formula (I). According to some embodiments, Ci-Cis alkylene is selected from the group consisting of CH2, C2H4, C3H6, C4H8, C5H10, CeHu, C7H14, CsHie, C9H18, C10H20, C11H22, C12H24, C13H26, C14H28, C15H30, C16H32, C17H34, and C18H36. Each possibility is a separate embodiment. In some embodiments, the Ci-Cis alkylene is straight, branched, further substituted, unsubstituted, or containing heteroatom. Each possibility is a separate embodiment. According to some embodiments, Ci-Cis alkylene is CsEfc.

[0150] According to some embodiments of formula (I), Z is , i.e. C3H6, and the compound is represented by the structure of compound (I):

[0151] (Compound I)

[0152] In some embodiments, the [A]'eof compound (I) is (CI-1), and the compound is represented by the structure of compound (I-CI-1):

[0153] Compound (I-CI-1) In some embodiments, the [A]'eof compound (I) is (CI-2), and the compound is represented by the structure of compound (I-CI-2):

[0154] Compound (I-CI-2)

[0155] According to some embodiments of formula wherein W is , i.e. C3H6, and the compound is represented by the structure of compound (II):

[0156] (Compound II) In some embodiments, the [A]'eof compound (II) is (CI-1), and the compound is represented by the structure of compound (II-CI-1):

[0157] Compound (II-CI-1)

[0158] In some embodiments, the [A]'eof compound (II) is (CI-2), and the compound is represented by the structure of compound (II-CI-2):

[0159] Compound (II-CI-2)

[0160] There is provided, in accordance with some embodiments, a compound represented by formula (II):

[0161] (Formula II) wherein:

[0162] X is absent, or is selected from substituted or unsubstituted C1-C20 hydrocarbylene, substituted or unsubstituted C1-C20 hydrocarbylene; e and n are integers from 1-1000; n2is an integer from 1-100; and

[0163] [A'] is represented by formula (CI-1): ination thereof.

[0164] (CI-2)

[0165] According to some embodiments of formula (II), the compound is neutral. According to some embodiments of formula (II), when [A ']eis represented by (CI-1), e = 2 * n. According to some embodiments, when [A ']eis represented by (CI-1), e = q.

[0166] According to some embodiments of formula (II), when [A ']eis represented by (CI-2), e = q. According to some embodiments of formula (II), the charge is single or double, delocalized at the melamine moiety, and the formula may be further represented by formula (IF) (11(2+)), or (IF (2+)), or any tautomer thereof:

[0167] (Formula IF (2+))

[0168] According to some embodiments, n and e are each independently integers from: 5-200, 100-200, 100-500, 200-300, 300-400, 400-500, 500-600, 100-700, 600-700, 700-800, 800-900, and 900-1000. Each possibility is a separate embodiment. According to some embodiments, the compound of formula (II) is a complex consisting of oppositely charged polymers and / or oligomers. In accordance with some embodiments, the first polymer is an organic polymer consisting of positively charged melamine-based monomers, and the second polymer and / or oligomer includes negatively charged monomers of borate or phosphate. In some embodiments, the polymers are interacting via electrostatic interactions and / or via other polar interactions. In some embodiments, the polymers are at least partially cross-linked.

[0169] According to some embodiments of formula (II), the (substituted or unsubstituted) Ci- C20 hydrocarbylene of X may include alkyl, alkylene, alkenyl, alkenylene, alkynyl, alkynylene, cycloalkyl, cycloalkylene, aryl, arylene, or any combination thereof.

[0170] In some embodiments, the symbol “ ”, as detailed in formula (II), denotes the point(s) of attachment of an organic substituent radical to a defined organic portion(s) radical of the compound. In some embodiments, for example, the organic portion(s) radical may refer to , i.e. C5H10.

[0171] According to some embodiments of formula (II), X is absent, and the compound is represented by the structure:

[0172] (Compound III) In some embodiments, the [A]'eof compound (III) is (CI-1), and the compound is represented by the structure of compound (III-CI-1):

[0173] Compound (III-CI-1)

[0174] In some embodiments, the [A]'eof compound (III) is (CI-2), and the compound is represented by the structure of compound (III-CI-2):

[0175] According to some embodiments of formula (II), X is O , and the compound is represented by the structure:

[0176] (Compound IV)

[0177] In some embodiments, the [A]'eof compound (IV) is (CI-1), and the compound is represented by the structure of compound (IV-CI-1):

[0178] Compound (IV-CI-1)

[0179] In some embodiments, the [A]'eof compound (IV) is (CI-2), and the compound is represented by the structure of compound (IV-CI-2):

[0180]

[0181] Compound (IV-CI-2)

[0182] In some embodiments, the [A]'eof compound (IV) includes (CI-1) and (CI-2), and the compound is represented by the structure of compound (IV-CI-1-2):

[0183] Compound (IV-CI-1-2)

[0184] According to some embodiments of formula (II), X is wherein Y is a (substituted or unsubstituted) C1-C20 hydrocarbylene. In some embodiments, the substituted or unsubstituted C1-C20 hydrocarbylene may include alkyl, alkylene, alkenyl, alkenylene, alkynyl, alkynylene, cycloalkyl, cycloalkylene, aryl, arylene, or any combination thereof. According to some embodiments of formula ( wherein

[0185] (Compound V) In some embodiments, the [A]'eof compound (V) includes (CI-1), and the compoundsented by the structure of compound (V-CI-1):

[0186] Compound (V-CI-1)

[0187] In some embodiments, the [A]'eof compound (V) includes (CI-2), and the compoundsented by the structure of compound (V-CI-2):

[0188] Compound (V-CI-2)

[0189] According to some embodiments of formula wherein the compound is represented by the structure:

[0190] In some embodiments, the [A]'eof compound (VI) includes (CI-1), and the compound is represented by the structure of compound (VI-CI-1):

[0191] Compound (VI-CI-1)

[0192] In some embodiments, the [A]'eof compound (VI) includes (CI-2), and the compoundsented by the structure of compound (VI-CI-2):

[0193] Compound (VI-CI-2)

[0194] According to some embodiments of formula ( wherein and the compound is represented by the structure:

[0195]

[0196] (Compound VII)

[0197] In some embodiments, the [A]'eof compound (VII) is (CI-2), and the compound is represented by the structure of compound (VII-CI-2):

[0198] Compound (VII-CI-2)

[0199] In some embodiments, the [A]'eof compound (VII) is (CI-1), and the compound is represented by the structure of compound (VII-CI-1):

[0200] Compound (VII-CI-1)

[0201] According to some embodiments of formula ( wherein the compound is represented by the structure:

[0202] (Compound VIII)

[0203] In some embodiments, the [A]'eof compound (VIII) is (CI-1), and the compound is represented by the structure of compound (VIII-CI-1):

[0204] Compound (VIII-CI-1)

[0205] In some embodiments, the [A]'eof compound (VIII) is (CI-2), and the compound is represented by the structure of compound (VIII-CI-2):

[0206] Compound (VIII-CI-2)

[0207] According to some embodiments of formula ( the compound is represented by the structure:

[0208] (Compound IX)

[0209] In some embodiments, the [A]'eof compound (IX) is (CI-1), and the compound is represented by the structure of compound (IX-CI-1):

[0210] Compound (IX-CI-1)

[0211] In some embodiments, the [A]'eof compound (IX) is (CI-2), and the compound is represented by the structure of compound (IX-CI-2): Compound (IX-CI-2)

[0212] According to some embodiments, the compound is characterized by a watercompatibility that is higher by at least about 1.5-3-fold compared to its corresponding uncharged starting material, for example, about 3-5-fold, about 5-6-fold, about 6-8-fold, about 8-10-fold, or about 10-13-fold. Each possibility is a separate embodiment. According to some embodiments, the compound is more hydrophilic compared to its corresponding uncharged starting material.

[0213] Advantageously, and according to some embodiments, the compound is capable of being homogeneously dispersed in a polar protic solvent. In some embodiments, the compound is capable of being homogeneously dispersed in a polar protic solvent that is water. According to some embodiments, the polarity of the complex compound which is induced by the charged moieties and represented in formulas (I) and / or (II), facilitates dispersion thereof within the polar protic solvent. In some embodiments, the polarity induced by the (stabilized) charged moieties of the complex compound, as represented in formulas (I) and / or (II), facilitates its dispersion in water. According to some embodiments, the dispersion of the compound in the polar protic solvent is stable for at least about 60 hours at room temperature, for example, for at least about 80 hours, 100 hours, 120 hours, 140 hours, 160 hours, or 180 hours. Each possibility is a separate embodiment. In some embodiments, the polar protic solvent may include methanol, ethanol, butanol, isopropanol, water, or a combination thereof. Each possibility is a separate embodiment. According to some embodiments, the polar protic solvent includes water. In accordance with some embodiments, the polar protic solvent may be incorporated in a FR composition. In some embodiments, the FR composition incorporates water as the polar protic solvent. According to some embodiments, the FR composition is used to facilitate the application of the FR compound to a designated manufactured product, such as textile. According to some embodiments, the FR compound is hydrophilic and is, therefore, dispersed in a polar protic solvent. According to some embodiments, the FR compound is hydrophilic and is, therefore, well dispersed in water. According to some embodiments, the FR compound is hydrophilic due to polarity induced by the stabilized charged moieties of the complex. The charged moieties may include borate, phosphate, and charged melamine, as detailed herein.

[0214] In some embodiments, the polarity induced by the (stabilized) charged moieties of the complex compound, as represented in formulas (I) and / or (II), facilitates its homogenous incorporation in a master batch. A master batch is a mixture of additives dispersed in a carrier resin and it is used in plastics manufacturing to modify properties such as FR, color, mechanical properties, etc. The additives are blended and extruded together with the resin. According to some embodiments, the FR compound disclosed herein is homogenously dispersed in a master batch. In some embodiments, the dispersion is facilitated by the polarity of the complex compound. In some embodiments, the dispersion is facilitated by the charged moieties of the complex compound. In some embodiments, the dispersion of the herein disclosed FR compound is maintained homogenous throughout the production process. In some embodiments, the dispersion of the herein disclosed FR compound is maintained homogenous throughout the extrusion process. In some embodiments, the herein disclosed FR compound facilitates the production of a homogeneous product. In some embodiments, the herein disclosed FR compound facilitates the production of a smooth product.

[0215] According to some embodiments, the compound of formula (I) and / or (II) is characterized by a decomposition temperature of at least about 350 °C at 25% (w / w) mass loss (Td25) upon heating the compound at a heating rate of 20 °C / min under a nitrogen flow of 60 ml / min, for example, at least about 400 °C, at least about 425 °C, at least about 450 °C, or at least about 500 °C. Each possibility is a separate embodiment. According to some embodiments, the compound of formula (I) is characterized by a decomposition temperature of at least about 400°C at 50% (w / w) mass loss (Tdso) upon heating the compound at a rate of 20 °C / min under a nitrogen flow of 60 ml / min, for example, at least about 450 °C, at least about 475 °C, at least about 500 °C, or at least about 600 °C. Each possibility is a separate embodiment.

[0216] Advantageously, and according to some embodiments, the compound of formula (I) and / or (II) exhibit high thermal stability which is reflected in its capability to effectively retard flame at high temperatures, as detailed.

[0217] In some embodiments, the compound of formula (I) and / or (II) is characterized by a heat stability region that spans up to at least about 550 °C, for example, at least about 600 °C, at least about 600 °C, or at least about 650 °C. Each possibility is a separate embodiment.

[0218] According to some embodiments, the compound of formula (I) or (II) disclosed herein is capable to retard flame when incorporated into paint, textile, plastic, coating, and / or impregnation. According to some embodiments, the compound is capable to retard flame when impregnated in wood, concrete, and / or textile. Each possibility is a separate embodiment.

[0219] According to some embodiments, the compound of formula (I) or (II) disclosed herein is characterized by flame retardation activity. In some embodiments, the compound disclosed herein is capable to retard flame when incorporated into a plastic material. In some other embodiments, the compound disclosed herein is characterized by a flame retardation activity when incorporated into textiles. The compound disclosed herein prevents the burning of the textiles in which it is incorporated. In some embodiments, the compound exhibits flame retardation activity according to ASTM D6413 / D6413M-15 vertical flammability test.

[0220] According to some embodiments, the compound is capable of minimizing a char length by at least about 2-fold compared to a corresponding melamine-based neutral polymer.

[0221] According to some embodiments, the compound of formula (I) or (II) disclosed herein, when incorporated in a textile or plastic material in an amount of at least about 5% (w / w), facilitates passing a standard flaming test. For example, in some embodiments, the herein disclosed compound facilitates passing a standard when incorporated in a textile or plastic material in an amount of at least 2%, 5%, 7%, 10%, 15%, 20%, 25%, 30%, 35%, or 40% (w / w) . Each possibility is a separate embodiment.

[0222] According to some embodiments, the compound of formula (I) or (II) disclosed herein enables passing a standard flaming test ASTM D6413 / D6413M. In some embodiments, the compound of formula (I) or (II) disclosed herein enables passing a standard flaming test ASTM D6413 / D6413M, when incorporated in a textile in an amount of at least about 2%, 5%, 7%, 10%, 15%, 20%, 25%, 30%, 35%, or 40% (w / w). Each possibility is a separate embodiment. In some embodiments, the incorporation of the herein disclosed FR compound in textiles or plastic material can be, in some embodiments, in an amount of between about 5% and about 50% (w / w). For example, the incorporation of the herein disclosed FR compound can be, in some embodiments, in an amount of between about 10% and about 40%, between about 20% and about 40%, or between about 10% and about 30%. Each possibility is a separate embodiment.

[0223] According to some embodiments, the compound of formula (I) or (II) disclosed herein enables passing a standard flaming test (e.g., UL-94), when incorporated in a plastic material, such as ABS, in an amount of at least about 2%, 5%, 7%, 10%, 15%, 20%, 25%, 30%, 35%, or 40% (w / w). Each possibility is a separate embodiment. For example, in some embodiments, the herein disclosed compound enables passing a standard flaming test (e.g., UL-94), when incorporated in a plastic material in an amount of between about 15% and about 50% (w / w), for example, 20-50%, 20-45%, 20-40%, 25-40%, or 30-40% (w / w) of the plastic material. Each possibility is a separate embodiment.

[0224] The FR compound may display several possible mechanisms of action towards fire retardation. In some embodiments, the advantageous FR compound includes a plurality of melamine moieties that can form ammonia gas when exposed to a flame / fire. In some embodiments, the inert gas dilutes the combustible gas, such as oxygen, thereby reducing the flame potential near the FR compound and the designated manufactured product in which it is implemented. In other embodiments, the advantageous FR compound disclosed herein includes high molecular weight polymers. According to some embodiments, the high molecular weight polymers include numerous covalent bonds that can break during an exposure to a fire / flame while absorbing the evolved heat energy, through an endothermic degradation. In yet another embodiment, the advantageous FR compound, which includes polyphosphate units, can form a protective blocking char layer when exposed to a fire / flame. In accordance with some embodiments, the char layer containing phosphorus may create a barrier between the burned and unbumed parts of the product, thereby preventing the fire from spreading. Therefore, in accordance with some embodiments, the FR compound provided herein may act as FR by multiple synergized mechanisms, and thus may serve as a highly performing FR compound.

[0225] According to some embodiments, the compound of formula (I) and / or (II) disclosed herein is a fire retardant. According to some embodiments, the compound is physically mixed during and / or after a manufacturing process to obtain a product that is resistant to burning. In some embodiments, the product may include but is not limited to thermoplastic polymer, thermosetting polymer, metal, paint, fabric, wood, liquid, gel, or a combination thereof. Each possibility is a separate embodiment.

[0226] According to some embodiments, the compound is used to retard flame when incorporated into paint, coating, and / or in impregnation. Each possibility is a separate embodiment.

[0227] According to some embodiments, the compound is used to retard flame when impregnated in wood, concrete, and / or textile. Each possibility is a separate embodiment. According to some embodiments, the herein disclosed compound of formula (I) or (II) is for use as fire retardant.

[0228] According to some embodiments, the wood product, into which the compound may be incorporated as FR, may be selected from furniture, building, instrument, paper, decoration, art piece, or toy. Each possibility is a separate embodiment.

[0229] According to some embodiments, the textile product, in which the compound may be incorporated as FR, may include but is not limited to cloth, uniform, curtain, household-related product, lab coat, firefighter fire extinguishing uniform, or custom. Each possibility is a separate embodiment. In accordance with some embodiments, the textile product may include but is not limited to fibers of cotton, silk, wool, viscose, polyester, nylon, polyaramid, Nomex, Kevlar, pyrovatex, linen, rayon, lyocell, cellulose, modacrylic, polybenzobisoxazole (PBO), polybenzimidazole (PBI), polysulfonamide (PSA), polyphenylene sulfide, polyacrylic, oxidized polyacrylic, partially oxidized polyacrylic (including partially oxidized polyacrylonitrile), polyether-ketone, or novoloid. Each possibility is a separate embodiment.

[0230] According to some embodiments, the thermoplastic polymer or thermosetting polymer product in which the compound may be incorporated as FR includes but is not limited to rubber, polypropylene, polyethylene, polystyrene, polyamide, polyimide, polyester, polyurethane, polycarbonate, polyacrylate, urea formaldehyde, polysulfone, epoxy, neoprene polynitrile, polyphenol, polyolefin, polyvinyl, polyvinyl chloride (PVC), silicone, poly styrene-butadiene, fluorinated poly ethylene-propylene, acrylonitrile butadiene styrene (ABS), ethylene vinyl acetate, polyphenylene oxide, polyethylene terephthalate (PET), polyether, a block copolymer thereof, derivatives thereof, fluoropolymer and co-polymer thereof, further cross-linked form thereof, or a combination thereof. Each possibility is a separate embodiment.

[0231] According to some embodiments, the plastic-containing product in which the FR compound may be incorporated may be selected from but is not limited to electronic device, textile, toy, instrument, furniture, and insulation material. Each possibility is a separate embodiment.

[0232] According to some embodiments, the FR compound is physically mixed during and / or after a product manufacturing process to obtain a product that is resistant to burning. In some embodiments, the compound may be incorporated into the product as part of a masterbatch, i.e. during the product’s manufacturing. In some embodiments, the compound may be applied as part of a concentrated mixture of pigments and / or additives blended and extruded together in a carrier matrix, such as resin or wax. In some embodiments, the compound-incorporated matrix is utilized to add the FR compound to a manufactured plastic-containing product. In some embodiments, the matrix may be used for coloring or for imparting other properties. According to some embodiments, the imparted properties may include fire retardation. According to some embodiments, the FR compound may be incorporated into the manufactured product as a raw and / or undiluted compound to introduce fire retardation.

[0233] In yet other embodiments, the FR compound may be applied to a product material or composition upon product’s manufacturing. In some embodiments, the application of the FR compound may be performed by using a method selected from but not limited to dip coating, spray coating, layer-by-layer deposition, spreading, or a combination thereof. Each possibility is a separate embodiment.

[0234] Advantageously, and in accordance with some embodiments, the FR compound is homogeneously dispersed into the applied FR composition used to implement it in the product, before, and / or after product manufacturing. In some embodiments, the FR compound is stably and homogeneously dispersed in a FR composition used for, but not limited to, coating, impregnation, textiles, master-batch, pigments, or additives. Each possibility is a separate embodiment. In some embodiments, the advantageous stable FR dispersion facilitates the processing of the FR compound. In additional embodiments, the advantageous stable FR dispersion facilitates the processing of the rest of the additives implemented in the designated product’s manufacturing.

[0235] There is provided, in accordance with some embodiments, a method of fire retardation, the method includes incorporating the herein disclosed compound(s) of formula (I) or (II) in or onto paint, coating an / or impregnation. There is provided, in accordance with some embodiments, a method of fire retardation, the method including incorporating the herein disclosed compound of formula (I) or (II) in impregnation of wood, concrete, and / or textile. Each possibility is a separate embodiment.

[0236] There is provided, in accordance with some embodiments, a method of fire retardation, the method including incorporating the herein disclosed compound of formula (I) or (II) in a plastic material. There is provided, in accordance with some embodiments, a method of producing the compound disclosed herein, the method includes: providing a first component, wherein the first component is represented by formula (I-

[0237] N):

[0238] (Formula I-N) wherein:

[0239] - Z is Ci-Cis alkylene, wherein W is Ci-Cis alkylene; and q is an integer from 1-1000; or wherein the first component is represented by formula (II-N):

[0240] (Formula II-N) wherein: X is absent, or is selected from substituted or unsubstituted C1-C20 in Y is substituted or unsubstituted Ci-

[0241] C20 hydrocarbylene; n is an integer from 1-1000; and n2is an integer from 1-100; providing a second component of formula (CI-l-N): nation thereof;

[0242] (CI-2-N) wherein: e is an integer from 1-1000; and

[0243] G+is a cationic counter ion; mixing the first and the second components to obtain a mixture; and heating the mixture to produce the compound of formula (I) or (II). According to some embodiments, a general route of synthesis of formula (I) is set forth in Scheme 1, and a general route of synthesis of formula (II) is set forth in Scheme 2:

[0244] Scheme 1 : (F ormul a I-N) (F ormul a I)

[0245] Scheme 2:

[0246] (Formula II-N) (Formula II) wherein:

[0247] [GA]eis represented by the structure of (CI-l-N) and / or (CI-2-N), wherein [GA]ecomprising G+and [A'];

[0248] G is a natural form of the G+cationic counter ion; and

[0249] [A']eis the negatively charged form of (CI-l-N) and / or the (CI-2-N), i.e. (CI-1) and / or (CI-2), and is represented by the structures:

[0250] (CM) (CI-2)

[0251] A reference is now made to FIG. 1, which schematically illustrates a flowchart of steps of a method for producing a FR compound, according to some embodiment. As shown in FIG. 1, manufacturing method 100 includes, in accordance with some embodiments, step 110 providing a first component, such as formula (I-N) or formula (II-N). In step 120, a second component, such as (CI-l-N) and / or (CI-l-N), is provided, according to some embodiments. In step 130, the first and the second components are mixed to obtain a reaction mixture. According to some embodiments, the two components are solids. The mixing may be done, according to some embodiments, via a solid-state synthetic technique, such as ball milling, to grind the two solids together, and later on to obtain a homogeneous product, in accordance with some embodiments. In step 140, according to some embodiments, the reaction mixture is heated up (to a high temperature of above 150 °C) to provide the FR compound. In some embodiments, ammonia gas is formed during the synthesis. The ammonia escapes from the reaction mixture and, thereby, facilitates the complexation of the FR product, in accordance with some embodiments.

[0252] According to some embodiments, the molar ratio between the total e provided and the n or q provided is between 1 : 10 and 10: 1, for example, between 1 :7 and 7: 1, between 1 :3 and 3: 1, or 1 :5 and 5: 1. According to some embodiments, the molar ratio between e and n or q is about 2: 1-1 :2, for example, 2: 1, 1.5: 1, 1.2: 1, 1 : 1, or 1 :2. Each possibility is a separate embodiment. According to some embodiments, the molar ratio between e and n or q is 1.2: 1.

[0253] According to some embodiments, the cationic counter ion G+of formula (CI-l-N) and / or (CI-2-N) is a metal cation or a positively charged small molecule.

[0254] In some embodiments, the metal can be an alkali metal, alkaline earth metal, transition metal, or main group metal. Each possibility is a separate embodiment. According to some embodiments, the metal is lithium, sodium, potassium, cesium, cerium, magnesium, manganese, iron, calcium, strontium, cobalt, titanium, aluminum, copper, cadmium, or zinc. Each possibility is a separate embodiment. In some embodiment, the cationic counter ion can be silver, barium, strontium, nickel, chromium, cobalt, manganese, lead, tin, or mercury. Each possibility is a separate embodiment.

[0255] In some embodiments, the second component formula (CI-l-N) and / or (CI-2-N) is a metal salt, for example, a lithium salt, a sodium salt, a potassium salt, a cesium salt, a cerium salt, a magnesium salt, a manganese salt, an iron salt, a calcium salt, a strontium salt, a cobalt salt, a titanium salt, an aluminum salt, a copper salt, a cadmium salt, or a zinc salt. Each possibility is a separate embodiment.

[0256] According to some embodiments, the cationic counter ion is natural basic amino acids lysine, arginine or histidine, non-natural basic amino acid, EDTA, or a quaternary ammonium cation. Each possibility is a separate embodiment.

[0257] According to some embodiments, quaternary ammonium salts corresponding to the quaternary ammonium cation can originate from an amine moiety. In some embodiments, the second component formula (CI-l-N) and / or (CI-2-N) is an ammonium salt. In some embodiments, (the second component) formula (CI-l-N) and / or (CI-2-N) is a melaminium salt. According to some embodiments, the corresponding amine is a moiety of ammonia, melamine, triethyl amine, diisopropyl amine, ethanol amine, diethanol amine, triethanol amine, morpholine, N- methylmorpholine, piperidine, N-methylpiperidine, N-ethylpipendine, dibenzylamine, piperazine, pyridine, pyrazole, imidazole, or pyrazine. Each possibility is a separate embodiment.

[0258] According to some embodiments, an ammonium salt of formula (CI-l-N ) and / or (CI- 2-N) is an ammonia salt, a melamine salt, a triethyl amine salt, a trimethyl amine salt, a diisopropyl amine salt, an ethanol amine salt, a diethanol amine salt, a triethanol amine salt, a morpholine salt, an N-methylmorpholine salt, a piperidine salt, an N-methylpiperidine salt, an N-ethylpiperidine salt, a dibenzylamine salt, a piperazine salt, a pyridine salt, a pyrazole salt, a pyridazine salt, a pyrimidine salt, an imidazole salt, or a pyrazine salt. Each possibility is a separate embodiment. According to some embodiments, an ammonium salt of formula (CI-1- N) and / or (CI-2-N) is an ammonium salt. According to some embodiments, G+is NEU+, i.e. ammonium cation. According to some embodiments, G+is melaminium cation.

[0259] According to some embodiments, the mixing of the first component and the second component is initiated in a solid phase. According to some embodiments, the reaction is a solid- state synthesis. According to some embodiments, the first and second components are in a solid state at the initial reaction conditions. According to some embodiments, the reaction is devoid of a solvent.

[0260] In some other embodiments, the mixing further includes a solvent or a combination of solvents.

[0261] According to some embodiments, the mixing is performed by using a technique selected from: ball-milling, mortar and pestle, grinding, melting, pelleting, and any combination thereof. Each possibility is a separate embodiment.

[0262] According to some embodiments, the obtained mixture is a powder. According to some embodiments, the obtained mixture is a solid.

[0263] According to some further embodiments, the reaction mixture is supplemented with an acid. In some embodiments, the supplemented acid is boric acid.

[0264] According to some embodiments, the heating of the reaction mixture is performed at a temperature of at least about 100 °C. According to some embodiments, the heating of the reaction mixture is performed at a temperature of at least about 150 °C, for example, at least about 180 °C, at least about 210 °C, at least about 230 °C, at least about 260 °C, or at least about 290 °C. Each possibility is a separate embodiment.

[0265] According to some embodiments, the reaction involves the production of a neutral gas. According to some embodiments, the reaction involves the production of an ammonia gas. According to some embodiments, the produced ammonia gas is released and evacuated from the reaction mixture during the production of the FR complex compound. According to some embodiments, the evacuation of ammonia by-product further induces complexation in the FR compound. According to some embodiments, the complex includes fewer or no counter ions compared to the first component starting material. According to some embodiments, the reduction of a counter ion, i.e., formerly an ammonium counter ion, induces the charged / electrostatic interaction between the positive and negative polymer / oligomer. According to some embodiments, the release of the ammonia as a neutral species stabilizes the positive charges in the positive polymer to be further complexed with the negative polymer / oligomer, thereby employing the advantageous stability of the final FR complex compound. According to some embodiments, the entropically favored release of ammonia gas may thermodynamically favor the complexation process. There is provided, in accordance with some embodiments, a compound produced according to the method disclosed herein.

[0266] According to some embodiments, the compound produced by the method disclosed herein is represented by the formula (I):

[0267] (Formula I) wherein:

[0268] Z is Ci-Cis alkylene, wherein W is Ci-Cis alkylene; e and q are integers from 1-1000;

[0269] [A'] is represented by formula (CI-1): mbination thereof.

[0270] (CI-2)

[0271] According to some embodiments, the compound produced by the method disclosed herein is represented by the formula (II):

[0272] X is absent, or is selected from C1-C20 hydrocarbylene, O wherein Y is a C1-C20 hydrocarbylene; e and n are integers from 1-1000; n2is an integer from 1-100; and

[0273] [A'] is represented within the formula (CI-1):

[0274] (CI-1) within the formula (CI-2): combination thereof.

[0275] (CI-2)

[0276] According to some embodiments, the compound produced by the method disclosed herein is capable of being homogeneously dispersed in a polar protic solvent.

[0277] According to some embodiments, the compound produced by the method disclosed herein is characterized by a decomposition temperature of at least about 350°C at 25% (w / w) mass loss (Td2s), and at least about 400°C at 50% (w / w) mass loss (Tdso) upon heating the compound at a heating rate of 20 °C / min under a nitrogen flow of 60 ml / min.

[0278] According to some embodiments, the compound produced by the method disclosed herein enables passing a standard flaming test when incorporated in textile or plastic material in an amount of at least about 2% (w / w), between about 5% and about 50% (w / w), or in any other minimum amount or range amount disclosed herein.

[0279] According to some embodiments, the compound produced by the method disclosed herein enables passing a standard flaming test ASTM D6413 / D6413M, when incorporated in textile in an amount of at least about 2% (w / w), between about 5% and about 50% (w / w), or in any other minimum amount or range amount disclosed herein. According to some embodiments, the compound produced by the method disclosed herein enables passing a standard flaming test UL-94, when incorporated in plastic material in an amount of at least about 2% (w / w), between about 5% and about 50% (w / w), or in any other minimum amount or range amount disclosed herein.

[0280] There is provided, in accordance with some embodiments, a flame-retardant composition including the herein disclosed compound and an acceptable fire-retardant carrier, in a suitable amount, the composition being formulated for incorporation in textiles.

[0281] According to some embodiments, the composition includes a polar solvent. In some embodiments, the polar solvent is or includes water, in some embodiments, the herein disclosed compound is homogenously dispersed in the herein disclosed composition, including the polar solvent, such as water.

[0282] According to some embodiments, the composition is being stable for at least about 60 hours at room temperature.

[0283] According to some embodiments, the herein disclosed composition further includes another fire retardant.

[0284] There is provided, in accordance with some embodiments, a flame-retardant composition including the herein disclosed compound and an acceptable fire-retardant carrier, in a suitable amount, the composition being formulated for incorporation in plastic material.

[0285] There is provided, in accordance with some embodiments, a flame retarded plastic material including the herein disclosed compound.

[0286] There is provided, in accordance with some embodiments, a flame retarded plastic material including the herein disclosed compound, optionally in combination with other flame retardants.

[0287] There is provided, in accordance with some embodiments, a textile article of manufacture made of or coated with the compound disclosed herein.

[0288] There is provided, in accordance with some embodiments, a textile article of manufacture made of or coated with the compound disclosed herein, optionally in combination with other flame retardants. The following examples are presented in order to more fully illustrate some embodiments of the invention. They should, in no way be construed, however, as limiting the broad scope of the invention. One skilled in the art can readily devise many variations and modifications of the principles disclosed herein without departing from the scope of the invention.

[0289] EXAMPLES

[0290] Preparation of melamine-functionalized polysiloxane (starting material I-N-

[0291] Sodium bicarbonate (6.5 gr) was dissolved in distilled water (90 gr) followed by an addition of ethanol (70 gr). Then, under an inert atmosphere, 2,4-diamino-6-chloro-triazine (9 gr) was added to the reaction mixture while stirring, followed by a slow addition of 3- aminopropyl-triethoxysilane (13.9 gr). The mixture was then incubated / mixed for 7 h at 80 °C to obtain a product of the melamine-functionalized poly siloxane as a white powder. Preparation of poly(melamine-co-oxalyl) polymer (starting material II-N-

[0292] IV)

[0293] Oxalyl chloride (25.4 gr) and dichloromelamine (39 gr) were mixed in a mixture of solvents, including chloroform and toluene. The polycondensation was carried out at room temperature for 8 h. The mixture was then filtered and washed multiple times in water and hexane, and then dried to obtain the poly(melamine-co-oxalyl) as a white powder product. This polymer is a respective starting material for Compound IV. Preparation of poly(melamine-co-urea) (starting material II-N-VII)

[0294] Melamine (25 gr) and tolylene-2,4-diisocyanate (35 gr) were mixed in dimethylformamide (DMF) for 3 h at 75 °C. The slurry was then diluted in acetone, filtered, and washed with water to obtain the poly(melamine-co-urea) as a white powder in a yield of 80%. This polymer is a respective starting material for Compound VII.

[0295] Similarly, respective starting materials for compounds including urea linkage, i.e., Compounds II-N-V, II-N-VI, and II-N-VIII, are obtained. Accordingly, starting material II-N- V (for Compound V) utilizes the addition reaction of the amine moieties of melamine with isocyanate moieties of a pentylene- 1,5-diisocyanate. Starting material II-N-VI (for compound VI) utilizes the addition reaction of the amine moieties of melamine with isocyanate moieties of a l-(2-isocyanatoethyl)-5-(isocyanatomethyl)-l,3,3-trimethylcyclohexane. Starting material II-N-VIII (for compound VIII) utilizes the addition reaction of the amine moieties of melamine with isocyanate moieties of a 4,4 ‘ -methylenebi s(phenylisocyanate). Preparation of poly(melamine-co-oxalyl) polyphosphate complex compound

[0296] (compound IV-CI-2)

[0297] Poly(melamine-co-oxalyl) (see Example 2) (173 gr) and ammonium polyphosphate were mixed (100 gr) and ball-milled together in a ball -milling machine. The mixture was then transferred into a glass beaker coated with aluminum foil with multiple ventilation holes to allow the escape of the evolved ammonia gas. The beaker was placed in an oven and heated for 2 h at 230 °C. The reaction mixture was then allowed to cool down to room temperature, followed by drying in the milling machine.

[0298] The compound poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI- 2) is prepared by using melamine polyphosphate. Preparation of poly(melamine-co-oxalyl) tetraborate complex compound

[0299] (compound IV-CI-1)

[0300] Poly(melamine-co-oxalyl) (see Example 2) (173 gr), ammonium tetraborate tetrahydrate (191 gr), and boric acid (15 gr) were mixed and ball-milled together in a ballmilling machine. The mixture was then transferred into a glass beaker coated with aluminum foil with multiple ventilation holes to allow the escape of the evolved ammonia gas. The beaker was placed in an oven and heated for 2 h at 215 °C. The reaction mixture was then allowed to cool down to room temperature, followed by drying in the milling machine. Preparation of poly(melamine-co-oxalyl) tetraborate polyphosphate complex compound (compound IV-CI-1-2)

[0301] Poly(melamine-co-oxalyl) (see Example 2) (173 gr), ammonium polyphosphate (70 gr), ammonium tetraborate tetrahydrate (80 gr), and boric acid (7 gr) were mixed and ball- milled together in a ball-milling machine. The mixture was then transferred into a glass beaker coated with aluminum foil with multiple ventilation holes to allow the escape of the evolved ammonia gas. The beaker was placed in an oven and heated for 2 h at 260 °C. The reaction mixture was then allowed to cool down to room temperature, followed by drying in the milling machine. Preparation of melamine-functionalized polysiloxane polyphosphate complex compound (compound I-CI-2)

[0302] Melamine-functionalized poly siloxane (see Example 1) (195 gr) and ammonium polyphosphate (100 gr) were mixed and ball-milled together in a ball-milling machine. The mixture was then transferred into a glass beaker coated with aluminum foil with multiple ventilation holes to allow the escape of the evolved ammonia gas. The beaker was placed in an oven and heated for 2 h at 280 °C. The reaction mixture was then allowed to cool down to room temperature, followed by drying in the milling machine. Preparation of melamine-functionalized polysiloxane tetraborate complex compound (compound I-CI-1)

[0303] Melamine-functionalized polysiloxane (see Example 1) (195 gr), ammonium tetraborate tetrahydrate (191 gr), and boric acid (15 gr) were mixed and ball-milled together in a ball-milling machine. The mixture was then transferred into a glass beaker coated with aluminum foil with multiple ventilation holes to allow the escape of the evolved ammonia gas. The beaker was placed in an oven and heated for 2 h at 260 °C. The reaction mixture was then allowed to cool down to room temperature, followed by drying in the milling machine. Preparation of poly(melamine-co-urea) polyphosphate complex compound

[0304] (compound VII-CI-2)

[0305] Poly(melamine-co-urea) (see Example 3) (294 gr) and ammonium polyphosphate (100 gr) were mixed and ball-milled together in a ball-milling machine. The mixture was then transferred into a glass beaker coated with aluminum foil with multiple ventilation holes to allow the escape of the evolved ammonia gas. The beaker was placed in an oven and heated for 2 h at 240 °C. The reaction mixture was then allowed to cool down to room temperature, followed by drying in the milling machine. Complexes of poly(melamine derivatives) of compounds IX, VIII, VI, V, and III are obtained by an equivalent synthesis utilizing the solid phase synthetic approach as exemplified for complexes of polyphosphate / borate with poly(melamine-co-oxalyl) (compound IV) or poly(melamine-co-urea) (compound VII), in examples 4-6 and 9. The neutral melamine polymer of interest (i.e., the starting material) is mixed with ammonium tetraborate tetrahydrate and boric acid and / or ammonium polyphosphate via ball-milling, in a molar ratio of about 1 to 1. The mixture is then transferred to an oven for further reaction at a high temperature, and involves the release of ammonia gas. Reacting the starting material with phosphoric acid (comparative procedure)

[0306] A comparative experiment was conducted to evaluate an alternative synthetic pathway for preparing the poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2), utilizing phosphoric acid (instead of the abovementioned disclosed polyphosphate reagent). In this experiment, the starting material poly(melamine-co-oxalyl) (starting material II-N-IV) was combined with an aqueous solution of phosphoric acid (50% w / w) at ambient temperature. After an incubation period of 50 minutes, the reaction was terminated, and the resulting powder was washed. Analysis of the recovered powder indicated that the starting polymer (poly(melamine-co-oxalyl)) had undergone hydrolysis of at least approximately 60%. This result demonstrated that the use of phosphoric acid in aqueous solution significantly reduced the formation of the desired complex compound.

[0307] In contrast, the solid phase method (as in Examples 4-9 above), surprisingly, yielded the desired complex compounds, without detectable hydrolysis. Advantageously, the preparation method utilizing polyphosphate reagent preserved the high molecular weight of the melamine-based polymer, enabling the formation of the flame-retardant complex compounds while maintaining polymer integrity and high molecular weight. Thermogravimetric analysis (TGA)

[0308] Thermogravimetric analysis (TGA) was performed on samples to evaluate their thermal stability by using a heating rate of 20 °C / min and a flow of nitrogen. Decomposition temperatures upon 25% (w / w) mass loss (Td2s), 50% (w / w) mass loss (Tdso), and 75% (w / w) mass loss (Td?s) were measured for poly(melamine-co-oxalyl) starting material and corresponding complexes thereof, as seen in FIG. 2-5, and summarized in Table 1. Table 1.

[0309] FIG. 2 shows a thermogram of a sample of poly(melamine-co-oxalyl) (starting material II-N-IV) demonstrating a non-significant thermal resistance. The decomposition temperatures that can be estimated from the thermogram are: Td25 = 300 °C, Tdso = 324 °C, and Td?s = 400 °C. In contrast, FIG. 3 shows a thermogram of a sample of poly(melamine-co-oxalyl) tetraborate complex (compound IV-CI-1) demonstrating a significant thermal resistance over a region of at least about 550 °C. The decomposition temperatures that can be estimated from the thermogram are: Td25 = 395 °C, Tdso = 425 °C, and Td?s = 455 °C. In addition, FIG. 4 shows a thermogram of a sample of poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2) demonstrating a significant thermal resistance over a region of at least about 550 °C. The decomposition temperatures that can be estimated from the thermogram are: Td25= 390 °C, Tdso = 425 °C, and Td?s = 450 °C. Furthermore, FIG. 5 shows a thermogram of a sample of poly(melamine-co-oxalyl) tetraborate polyphosphate complex (compound IV-CI- 1-2) demonstrating a significant thermal resistance over a region of at least about 600 °C. The decomposition temperatures that can be estimated from the thermogram are Td25 = 280 °C and Td5o = 51O °C.

[0310] Therefore, advantageously, according to the TGA results the complexed compounds are expected to retard flames more efficiently compared to the neutral melamine polymer alone. 12 Composition for incorporating FR in textiles and sample preparation for

[0311] ASTM D6413 / D6413M analysis of flammability resistance of textiles

[0312] Dispersion compositions containing the tested compounds were prepared; these contained a surfactant, a wetting agent, a thickener, and acrylic binder emulsion, all of which are standard components in the following flammability tests. The dispersion compositions appeared homogenous and remained stable for more than a week. No phase separation was observed.

[0313] In contrast, when trying to make dispersion compositions of the neutral starting materials, sediments were observed 10-15 min after mixing of the ingredients.

[0314] The stability of the composition, including the herein disclosed complex compound, is advantageous since it facilitates the application of the composition to textiles via methods such as spraying, screen printing, or roll-to-roll processes.

[0315] The test fabrics were impregnated with the dispersions, and then squeezed to a controlled pick-up of dispersion, followed by drying and curing at 150-160 °C for 3 minutes. The tests were performed on fabrics made of cotton, polyester, or a combination thereof. The inclusion of the add-on compound in the tested specimen was 5-50% (w / w), or preferably 10- 40% (w / w).

[0316] The objective of this test is to determine whether a fabric including a fire-retarding compound will continue to burn after the source of ignition is removed. For this purpose, a specimen of fabric in a size of 12 inches was suspended in an enclosed chamber, secured on three sides. The cut edge of the fabric on the bottom was exposed to a controlled methane flame for 12 seconds. After exposure to the flame, afterflame, afterglow, and char length were measured. ASTM D6413 / D6413M analysis of flammability resistance of textiles, including the flame-retardant compounds

[0317] A flame retardant activity was observed for:

[0318] Poly(melamine-co-oxalyl) polyphosphate (compound IV-CI-2) incorporated in a fabric of polyester / cotton (1 : 1), as exemplified in FIG. 6. - Poly(melamine-co-oxalyl) polyphosphate (compound IV-CI-2) incorporated in a fabric of cotton, as exemplified in FIG. 7.

[0319] - Melamine-functionalized polysiloxane polyphosphate (compound I-CI-2) incorporated in a fabric of polyester / cotton (1 : 1), as exemplified in FIG. 8.

[0320] - Melamine-functionalized polysiloxane polyphosphate (compound I-CI-2) incorporated in a fabric of cotton, as exemplified in FIG. 9.

[0321] - Poly(melamine-co-urea) polyphosphate (compound VII-CI-2) incorporated in a fabric of polyester, as exemplified in FIG. 10.

[0322] - Poly(melamine-co-urea) polyphosphate (compound VII-CI-2) incorporated in a fabric of cotton, as exemplified in Fig. 11.

[0323] A flame retardant activity was not observed for:

[0324] - Poly(melamine-co-oxalyl) (starting material II-N-IV) incorporated in a fabric of cotton, as exemplified in FIG. 12.

[0325] - Poly(melamine-co-oxalyl) (starting material II-N-IV) incorporated in a fabric of polyester, as exemplified in FIG. 13.

[0326] The test results demonstrate the fire-retardant activity of the advantageous complex compounds disclosed herein when incorporated into manufactured textile products. In addition, it shows the advantage of incorporating a complex consisting of oppositely charged polymer and / or oligomer, as opposed to incorporating a neutral melamine-polymer alone. Incorporation of FR compounds in plastic materials

[0327] The compounds disclosed herein were incorporated into plastic material, such as ABS to obtain FR retarded plastic material. Comparable incorporations were performed using corresponding neutral starting materials. The form / shape / texture and the homogeneity of the FR retarded plastic materials were visually examined and compared, after the extrusion.

[0328] Briefly, a FR compound of poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2) in an amount of 30-40% (w / w) of the FR retarded plastic material was mixed with Xibond synergistic agent in an amount of 2-5% (w / w) of the FR retarded plastic material, and with ABS grains in an amount of 55-65% (w / w) of the FR retarded plastic material. The obtained mixture was introduced into an extruder and melted at a temperature of above about 220 °C. The same procedure was performed using poly(melamine-co-oxalyl) (starting material II-N-IV). As can be seen in FIG. 14, when the poly(melamine-co-oxalyl) (starting material II-N-IV) was used, the extrudate that emerged from the extruder showed an inhomogeneous and rough form. However, as can be seen in FIG. 15, when the FR compound of poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2) was used, the extrudate exhibited a homogenous form.

[0329] FIG. 16 shows a corresponding photo of FR retarded plastic grains that were obtained from the inhomogeneous extrudate incorporating the poly(melamine-co-oxalyl) (starting material II-N-IV). The grains are rough and inhomogeneous. FIG. 17 shows a corresponding photo of FR retarded plastic grains that were obtained from the homogeneous extrudate incorporating the poly(melamine-co-oxalyl) polyphosphate complex (compound IV-CI-2). The grains in this case are smooth and homogeneous. UL-94 analysis in ABS plastic materials, including the flame-retardant compounds

[0330] A vertical burning test (V-0, V-l, and V-2) assessed how the material responded when positioned vertically and exposed to a 20 mm flame applied twice for 10 seconds each. During testing, the afterflame and afterglow times were recorded, along with observations of whether flaming drips ignited a cotton indicator placed below. Material was classified as V-0, V-l, or V-2 based on how quickly it extinguished and whether it produced flaming drips. V-0 material exhibited the fastest self-extingui shing and produced no flaming drips, while V-l material was allowed slightly longer afterflame times but still could not ignite the cotton. This test provided a rigorous measure of flame retardance for a vertically mounted component.

[0331] A vertical flammability test was conducted on 3.2 mm ABS plastic sticks, incorporating poly(melamine-co-oxalyl) polyphosphate complex compound (compound IV-CI-2) and polycarbonate. The test followed the protocol of test UL 94:2022-Plastic Materials for Parts in Devices and Appliances-Flammability (level VI, V2). Results are shown in the performance specifications table in FIG. 18A. As can be seen in the categories table shown in FIG. 18B, the flammability results are suitable for V-l category but are very close to being categorized by V-0 grade.

[0332] A Horizontal Burning (HB) test evaluated the flammability of a plastic material in horizontal orientation. A bar-shaped specimen was mounted at a 45° inclination and was exposed to a methane flame at one end for up to 30 seconds. The burning rate was determined based on the time it took for the flame front to travel a set distance. To be classified as HB, the material could not burn faster than 40 mm / min for specimens 3.0-13 mm thick or 75 mm / min for thinner ones, or it had to self-extinguish before reaching the 100 mm mark. This test served to identify materials with basic horizontal flame resistance.

[0333] A horizontal flammability test was conducted on 1.6 mm ABS plastic sticks, incorporating the poly(melamine-co-oxalyl) polyphosphate complex compound (compound IV-CI-2). The test followed the protocol of UL 94:2022-Plastic Materials for Parts in Devices and Appliances-Flammability (level HB). Results are shown in the performance specification table in FIG. 19. As can be seen, according to the test criteria, the sample is classified as HB grade.

[0334] A horizontal flammability test was conducted on 1.6 mm ABS plastic sticks, incorporating the melamine-functionalized polysiloxane polyphosphate complex compound (compound I-CI-2). The test followed the protocol of UL 94:2022-Plastic Materials for Parts in Devices and Appliances-Flammability (level HB). Results are shown in the performance specification table in FIG. 20. As can be seen, according to the test criteria, the sample is classified as HB grade.

[0335] A horizontal flammability test was conducted on 3.2 mm ABS plastic sticks, incorporating the poly(melamine-co-oxalyl) tetraborate complex compound (compound IV- CLl) and polycarbonate. The test followed the protocol of UL 94:2022-Plastic Materials for Parts in Devices and Appliances-Flammability (level HB). Results are shown in the performance specification table in FIG. 21. As can be seen, according to the test criteria, the sample is classified as HB grade.

[0336] The test results demonstrate the fire-retardant activity of the advantageous complex compounds disclosed herein when incorporated in plastic products.

Claims

CLAIMS1. A compound represented by formula (I):(Formula I) wherein:Z is Ci-Cis alkylene,wherein W is Ci-Cis alkylene; e and q are integers from 1-1000;[A'] is represented by formula (CI-1):ination thereof.(CI-2)2. The compound of claim 1, being a neutral compound.

3. The compound of any one of claims 1 and 2, wherein the compound is capable of being homogeneously dispersed in a polar protic solvent.

4. The compound of claim 3, wherein the solvent comprises water.

5. The compound of any one of claims 3 and 4, wherein the dispersion in the polar protic solvent is stable for at least about 60 hours at room temperature.The compound of any one of claims 1-5, wherein Z isand the compound is represented by the structure:(Compound I)7. The compound of any one of claims 1-5, whereinwherein Wand the compound is represented by the structure:(Compound II)8. The compound of any one of claims 1-7, for use as a fire retardant.

9. The compound of any one of claims 1-8, characterized by a decomposition temperature of at least about 350°C at 25% (w / w) mass loss (Td2s), and of at least about 400°C at 50% (w / w) mass loss (Tdso) upon heating the compound at a heating rate of 20 °C / min under a nitrogen flow of 60 ml / min.

10. The compound of any one of claims 1-9, wherein the compound, when incorporated in a textile or plastic material in an amount of at least about 5% (w / w), facilitates passing a standard flaming test.

11. A compound represented by formula (II):(Formula II) wherein:X is absent, or is selected from C1-C20 hydrocarbylene, Owherein Y is a C1-C20 hydrocarbylene; e and n are integers from 1-1000; n2is an integer from 1-100; and[A'] is represented by formula (CI-1):ination thereof.(CI-2)12. The compound of claim 11, is a neutral compound.

13. The compound of any one of claims 11 and 12, wherein the compound is capable of being homogeneously dispersed in a polar protic solvent.

14. The compound of claim 13, wherein the solvent comprises water.

15. The compound of any one of claims 13 and 14, wherein the dispersion in the polar protic solvent is stable for at least about 60 hours at room temperature.

16. The compound of any one of claims 11-15, wherein X is absent, and the compound is represented by the structure:

17. The compound of any one of claims 11-15, wherein X is O , and the compound is represented by the structure:(Compound IV)18. The compound of any one of claims 11-15, wherein19. The compound of claim 18, wherein Y is, and the compound is represented by the structure:the compound is represented by the structure:(Compound VI)21. The compound of claim 18, whereinthe compound is represented by the structure:(Compound VII)22. The compound of claim 18, whereinthe compound is represented by the structure:(Compound VIII)23. The compound of any one of claims 11-15, whereinthe compound is represented by the structure:(Compound IX)24. The compound of any one of claims 11-23, for use as a fire retardant.

25. The compound of any one of claims 11-24, characterized by a decomposition temperature of at least about 350°C at 25% (w / w) mass loss (Td2s), and at least about 400°C at 50% (w / w) mass loss (Tdso) upon heating the compound at a heating rate of 20 °C / min under a nitrogen flow of 60 ml / min.

26. The compound of any one of claims 11-25, when incorporated in a textile or a plastic material in an amount of at least about 5% (w / w) facilitates passing a standard flaming test.

27. A method of producing a compound according to any one of claims 1-10 and 11-26, the method comprising: providing a first component, wherein the first component is represented by formula (I-N):(Formula I-N) wherein:- Z is Ci-Cis alkylene,wherein W is Ci-Cis alkylene; and q is an integer from 1-1000; or wherein the first component is represented by formula (II-N):X is absent, or is selected from C1-C20 hydrocarbylene, OC1-C20 hydrocarbylene; n is an integer from 1-1000; and n2is an integer from 1-100; providing a second component of formula (CI-l-N):(CI-l-N)formula (CI-2-N):any combination thereof;(CI-2-N) wherein: e is an integer from 1-1000; andG+is a cationic counter ion; mixing the first and the second components to obtain a mixture; and heating the mixture to produce the compound of any one of claims 1-10 and 11-26.

28. The method of claim 27, wherein G+is NH4+and / or melaminium.

29. The method of any one of claims 27 and 28, wherein the obtained mixture is a powder.

30. The method of any one of claims 27-29, wherein the mixing is initiated in a solid phase.

31. The method of any one of claims 27-30, wherein the mixing is performed by using a technique selected from: ball-milling, mortar and pestle, grinding, melting, pelleting, and any combination thereof.

32. The method of any one of claims 27-31, wherein the heating is performed at a temperature of at least about 150 °C.

33. A compound produced according to the method of any one of claims 27-32.

34. The compound of any one of claims 1-26, for use as a flame-retardant compound in paint, coating, textile, plastic, and / or impregnation.

35. The compound of claim 34, wherein the impregnation is in wood, concrete, and / or textile.

36. The compound of any one of claims 1-26, for use as a flame-retardant compound in a plastic material.

37. A flame-retardant composition comprising the compound as defined in any one of claims 1-26, and an acceptable fire-retardant carrier, in a suitable amount, the composition being formulated for incorporation in textile.

38. The composition of claim 37, comprising a polar solvent.

39. The composition of claim 38, wherein the polar solvent is or comprises water.

40. A flame-retardant composition comprising the compound as defined in any one of claims 1-26, and an acceptable fire-retardant carrier, in a suitable amount, the composition being formulated for incorporation in plastic material.

41. The composition of any one of claims 37-39, being stable for at least about 60 hours at room temperature.

42. The composition of any one of claims 37-41, further comprising another fire retardant.

43. A flame retarded plastic material comprising the compound as defined in any one of claims 1-26, optionally in combination with one or more other flame retardants.

44. A textile article of manufacture made of or coated with the compound as defined in any one of claims 1-26, optionally in combination with one or more other flame retardants.

Images