WO2015024487A1 - Retardateur de flamme préparé à partir de dérivés d'amide et son procédé de préparation - Google Patents

Retardateur de flamme préparé à partir de dérivés d'amide et son procédé de préparation Download PDF

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Publication number
WO2015024487A1
WO2015024487A1 PCT/CN2014/084589 CN2014084589W WO2015024487A1 WO 2015024487 A1 WO2015024487 A1 WO 2015024487A1 CN 2014084589 W CN2014084589 W CN 2014084589W WO 2015024487 A1 WO2015024487 A1 WO 2015024487A1
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WO
WIPO (PCT)
Prior art keywords
melamine
phosphite
compound
mixture
salt
Prior art date
Application number
PCT/CN2014/084589
Other languages
English (en)
Inventor
Junli Li
Gary Woodward
Original Assignee
Rhodia Operations
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhodia Operations filed Critical Rhodia Operations
Priority to CN201480046748.3A priority Critical patent/CN105492520B/zh
Priority to KR1020167007213A priority patent/KR102300270B1/ko
Publication of WO2015024487A1 publication Critical patent/WO2015024487A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34928—Salts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0066—Flame-proofing or flame-retarding additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/14—Glass

Definitions

  • the present invention pertains to a process for manufacturing a melamine derivative mixture by a reaction between at least an amide derivative and a metallic phosphite salt, and the use of said reaction to produce a flame retardant.
  • Flame retardants are additives used in plastics and other industrial
  • halogen free flame retardant phosphonate HFFR, such as melamine pyrophosphate (MPP), which is widely used in thermoplastics and has a general molecular formula of C3H6N6 (H3PO 4 ) n .
  • MPP melamine pyrophosphate
  • the combination of nitrogen and phosphorus elements in MPP could help form a crosslinked char in the applied product, thus boosting its flame retardant performance.
  • thermoplastic additive has its own constrains and disadvantages when used for thermoplastics. For instance, off-gassing and liquid bleed out have been found in the thermoplastic systems incorporating MPP, and these problems are believed to be caused by phosphonate slat synergist interactions in the systems.
  • the present invention thus seeks to provide an economic approach to produce a new phosphonate HFFR additive that overcomes the aforesaid disadvantages of conventional phosphonate HFFR additives, which offers satisfactory and stable flame retardant properties while retaining good mechanical properties of the polymer it adds to.
  • the invention is directed to a melamine derivative mixture having flame retardant properties, and a process for manufacturing the same.
  • a process for manufacturing a melamine derivative mixture comprising at least the following steps:
  • step (iii) separating the reaction mixture obtained in step (ii) by a solid-liquid separation method to obtain a solid phase
  • step (iv) heating the solid phase obtained in step (iii), at a temperature between 150°C and 500°C in the presence of an oxidant, to obtain the melamine derivative mixture
  • Ri, R2, and R3 are independently hydrogen, hydroxyl, amino, or mono- or diCi-Ce alkyl amino; or Ci-Ce alkyl, C5-Ci6cycloalkyl, - alkylcycloalkyl, each being optionally substituted by a hydroxyl or a Ci- C 4 hydroxyalkyl, C2-C8alkenyl, Ci-Cealkoxyl, -acyl, -acyloxy, C6-C12 aryl, - OR1 and -N(Ri)R2; or are N-alicyclic or N-aromatic, where N-alicyclic denotes cyclic nitrogen containing compounds such as pyrrodiline, piperidine, imidazolidine, piperazine and N-aromatic denotes nitrogen containing heteroaromatic ring compounds such as pyrrole, pyridine, imidazole and pyrazine; X is phosphoric acid or pyrophosphoric acid, q is phospho
  • metallic phosphite or hydrogen phosphite salt refers to a salt containing a metallic cation and one anion of HPO3 2 ⁇ or H2PO3-.
  • a melamine derivative mixture can be produced, which offers excel flame retardant properties and helps retaining good mechanical properties of the polymer it adds to.
  • the melamine derivative mixture produced by the above process shows a better stability and polymer compatibility compared to the commercial MPP retardant, and can be effective as both vapour-phase and condensed-phase flame retardants.
  • the melamine mixture obtained from the process of the invention is also found to be less acidic in the aqueous solution, which gives a better compatibility in resin matrix.
  • Suitable Compound (N) for the present invention may be selected from a group consisting of: melamine, melamine cyanurate, melamine phosphate compounds, dimelamine phosphate compounds, melamine pyrophosphate compounds, melem, melam, melon, ammeline, ammelide and the like.
  • the Compound (N) is melamine.
  • the compound of "melamine” refers to a compound of the formula (III):
  • a metallic phosphite or hydrogen phosphite salt refers to a salt containing a metallic cation and one anion of HPO3 2 or H2PO3 " , wherein the metallic cation may be derived from a metal selected from the group consisting of alkali metals, alkaline earth metals, and transition metals.
  • the metallic phosphite or hydrogen phosphite salt include U2HPO3, UH2PO3,
  • the Solution (S) is an aqueous solution comprising the metallic phosphite or hydrogen phosphite salt.
  • Solution (S) is acidic and has a pH value preferably between 1.0 to 6.0, more preferably between 1.5 to 4.5.
  • the term "acidic" refers to a pH value of less than about 7, and the pH value refer to the pH of aqueous phases.
  • the pH value of the Solution (S) can be adjusted by judiciously adding to it an acid or a base. If the Solution (S) has a pH value higher than the desired pH value, then the pH value is adjusted by the addition of an appropriate acid (e.g. HCI, HNO3, H3PO3, H3PO2 or H3PO 4 ). Conversely, if the Solution (S) has a pH value lower than the desired pH value, then the pH value is adjusted by the addition of an appropriate base (e.g. NaOH, KOH KOH, Ca(OH) 2 , or NH 3 ).
  • an appropriate base e.g. NaOH, KOH KOH, Ca(OH) 2 , or NH 3
  • reaction time of step (ii) of the process invention can vary from 15
  • step (ii) of the process invention is influenced to a significant degree by the reaction temperature, the concentration and choice of reactants, the presence of a catalyst, and other factors in step (ii) which are selected by one skilled in the art.
  • the molar ratio of Compound (N) to the sum of phosphite and hydrogen phosphite salt in the Solution (S) is within the range of 1 :5 to 5:1 , preferably 1 :2 to 2:1 , and more preferably 1.1 :1 to 1 :1.1.
  • step (iii) of the process invention the reaction mixture obtained in step (ii) is separated by a suitable solid-liquid separation method to obtain a solid phase, wherein the solid-liquid separation method may be filtration, spray drying or the like.
  • the solid phase separated from step (iii) is heated at a temperature between 150°C and 500°C and in the presence of an oxidant.
  • the step (iv) generally results in a dry loss between 10 and 40% wt, on the basis of the weight of the solid phase separated from step (iii).
  • the oxidant used in step (iv) may be selected from air, oxygen, gaseous oxidant precursors such as oxides of nitrogen (N x O y ) and ozone, or other gaseous oxidants commonly used in the art.
  • gaseous oxidant precursors such as oxides of nitrogen (N x O y ) and ozone, or other gaseous oxidants commonly used in the art.
  • the heating time in step (iv) is typically selected to be 1 to 8 hours
  • the heating time in said step (iv) is selected by one skilled in the art to obtain a dry loss between 10 and 40% wt, based on the weight of the solid phase separated from step (iii).
  • the present invention also relates to a product susceptible to be obtained by the inventive process as afore-described.
  • the melamine derivative mixture according to the present invention provides enhanced stability.
  • the stability of the mixture can be evaluated by measuring the decomposition onset of the mixture by thermo gravimetric analysis (TGA).
  • TGA thermo gravimetric analysis
  • the melamine derivative mixture has a TGA temperature for 3% weight loss which is 300°C or higher under N2 atmosphere.
  • the melamine derivative mixture has a TGA temperature for 3% weight loss which is 330°C or higher under N2 atmosphere.
  • the heating rate of the TGA analysis is 10°C per min.
  • composition (P) comprising at least one polymer and a melamine derivative mixture as afore-described.
  • the at least one polymer in the Composition (P) is selected from the group consisting of polyphenylene ethers, polyamides such as PA66, PA6, PA610, or high-temperature polyamides (PPA/ PA4.6/ PA9T/
  • PA66.6T/ PA10T/ PA6.6T and blends of polyamides such as PA/ PET, PA/ ABS or PA/PP), polyesters, polycarbonates, epoxy resins; phenolic resins; acrylonitrile butadiene styrene (ABS); styrene acrilonitrile (SAN); mixtures of high impact polystyrene (HIPS) and polyphenylene ethers (such as PPO/HIPS); Styrene Butadiene Rubber and lattices (SBR and SB); and Halogenated polymers such as polyvinylchloride (PVC), and mixtures and blends of these polymers, expandable Polystyrene (EPS), and polybutylene terephthalate (PBT).
  • polyamides such as PA/ PET, PA/ ABS or PA/PP
  • polyesters polycarbonates, epoxy resins; phenolic resins; acrylonitrile butadiene styrene (ABS); styrene
  • composition (P) may further comprise one or more
  • flame retardant additives which could enhance its flame retardancy properties such as endothermic degradation, thermal shielding, dilution of gas phase, dilution of combustible portion, and radical quenching.
  • the additional flame retardant additive in the Composition (P) are notably described in US 6344158 , US 6365071 , US 6211402 , and US 6255371 .
  • Composition (P) is selected from the group comprising:
  • Phosphorous containing flame retardant additives such as:
  • phosphine oxide such as for example triphenylphosphine oxide, tri-(3-hydroxypropyl) phosphine oxide and tri-(3-hydroxy-2-methylpropyl) phosphine oxide;
  • phosphonic acids and their salts such as for example phosphinic acid of zinc, magnesium, calcium, aluminium or manganese, notably aluminium salt of
  • diethylphosphinic acid aluminium salt of dimethylphosphinic acid, or zinc salt of dimethylphosphinic acid;
  • cyclic phosphonates such as diphosphate cyclic esters that is for example Antiblaze 1045;
  • organic phosphates such as triphenylphosphate
  • inorganic phosphates such as ammonium polyphosphates and sodium polyphosphates
  • Nitrogen containing flame retardant additives such as: triazines, cyanuric acid and/or isocyanuric acid, melamine or its derivatives such as cyanurate, oxalate, phtalate, borate, sulfate, phosphate, polyphosphate and/or pyrophosphate, condensed products of melamine such as melem, melam, melon, tris(hydroxyethyl) isocyanurate, benzoguanamine, guanidine, allanto ' i ' ne and glycoluril,
  • triazines such as: triazines, cyanuric acid and/or isocyanuric acid, melamine or its derivatives such as cyanurate, oxalate, phtalate, borate, sulfate, phosphate, polyphosphate and/or pyrophosphate, condensed products of melamine such as melem, melam, melon, tris(hydroxye
  • Halogen containing flame retardant additives such as:
  • Bromine containing flame retardant additives such as polybromodiphenyloxydes (PBDPO), brominated polystyrene (BrPS), poly(pentabromobenzylacrylate), brominated indane,
  • tetradecabromodiphenoxybenzene (Saytex 120), ethane-1 ,2- bis(pentabromophenyl) or Saytex 8010 of Albemarle, tetrabromobisphenol A and brominated epoxy oligomers.
  • PDBS-80 from Chemtura
  • Saytex HP 3010 from Albemarle or FR-803P from Dea Sea Bromine Group
  • FR-1210 from Dea Sea Bromine Group
  • OBPE octabromodiphenylether
  • FR-245 from Dead Sea Bromine Group
  • FR-1025 from Dead Sea Bromine Group
  • F-2300 or F2400 Dead Sea Bromine Group
  • Inorganic flame retardant additives such as antimony trioxide, aluminium hydroxide, magnesium hydroxide, cerium oxide, boron containing compounds such as calcium borate.
  • These above-listed flame retardant additive compounds may be used alone or in combination in the Composition (P).
  • Charring agents and charring catalysts may also be added if necessary.
  • composition (P) may further comprise fillers and
  • lubricants e.g. stearic acid or stearate salts such as calcium stearate
  • glass fibers e.g. PTFE SN3306.
  • antidriping agents such as poly(tetrafluoroethylene), e.g. PTFE SN3306.
  • composition (P) may also comprise additives normally used for the manufacture of polymer compositions, such as plasticizers, nucleating agents, catalysts, light and/or thermal stabilizers, antioxidants, antistatic agents, colorants, pigments, matting agents, conductive agents such as carbon black, molding additives or the like.
  • additives normally used for the manufacture of polymer compositions such as plasticizers, nucleating agents, catalysts, light and/or thermal stabilizers, antioxidants, antistatic agents, colorants, pigments, matting agents, conductive agents such as carbon black, molding additives or the like.
  • the fillers and additives may be added by any conventional means, e.g. during the polymerization or as a molten mixture.
  • the additives are added to the polymer in a melt process, such as during a melt extrusion step.
  • the additives can be added to the polymer in a solid process, in a mechanical mixer, to produce a solid mixture that is subsequently melted, for example by extrusion process.
  • the Composition (P) may be used as raw material in the field of plastics processing, such as for the preparation of articles formed by injection molding, by injection/ blow-molding, by extrusion or by extrusion/blow- molding.
  • the Composition (P) is extruded in the form of rods, for example in a twin-screw extrusion device, said rods then being chopped into granules.
  • the molded components are then prepared by melting the granules produced above and feeding the molten composition into injection-molding devices.
  • examples include vehicle parts such as tubes, tanks, bodywork components, or components under the engine hood, as well as articles for the electrical and electronics applications, such as connecters.
  • PA 66 an aliphatic polyamide obtained from Solvay Advanced Polymers
  • PBT 1200 a polybutylene terephthalate resin obtained from Taiwan
  • Exolit OP1230 aluminium phosphinate from Clariant GmbH
  • MPP (Melapur-200): from BASF
  • a 250 mL reactor equipped with mechanical stirrer was charged with 120 g water and 30.46g of a calcium phosphite mixture obtained as mentioned above. Under stirring, 53.3g of a 85% orthophosphate acid solution was added into the resulting mixture at room temperature. After addition, the mixture was stirred for half an hour and then was filtered to remove unsolvable solid to get a clean solution. Then 58g melamine was slowly added into the filtrate with stirring for another 1 hour reaction. After that, this mixture was evaporated to remove all water to obtain a white solid. This white solid was heated at 330°C for 3 hours, with a weight loss of 22%, to convert into a calcium melamine phosphorous salt.
  • the P(lll) molar percentage in the phosphorus species of the calcium melamine phosphorous salt can be calculated to be 17%.
  • a 500 mL reactor equipped with mechanical stirrer was charged with 400g water and 60g of a calcium phosphite mixture. Under stirring, 91.34g of a 38% hydrochloride acid solution was added into the resulting mixture at room temperature. After addition, the mixture was stirred for half an hour and then was filtered to remove unsolvable solid to get a clean solution. Then 144g melamine was slowly added into the filtrate with stirring for another 1 hour reaction. After that, this reaction mixture was filtered to remove aqueous solution and obtained a white solid. This white solid was then heated at 330°C for 3 hours, with a weight loss of 23%, to convert into a calcium melamine phosphorous salt.
  • a 500 mL reactor equipped with mechanical stirrer was charged with 400 g water and 65.5g of a calcium phosphite mixture. Under stirring, 91.34g of a 38% hydrochloride acid solution was added into the resulting mixture at room temperature. After addition, the mixture was stirred for half an hour and then was filtered to remove unsolvable solid to get a clean solution. Then 144g melamine was added slowly into the filtrate with stirring for another one hour reaction. After that, this mixture was filtered to remove aqueous solution to obtain a white solid. This white solid was heated at 330°C for 3 hour to produce a calcium melamine phosphorous salt, with 23% weight loss during heating. The thus obtained calcium melamine
  • this salt product has a phosphorous valence of 4.11 , corresponding to a P(lll) percentage of 44.5% in its phosphorus species.
  • melamine phosphorous salt obtained in the above procedure also had a pH greater than 5, notably less acidic than a 10wt% aqueous solution of MPP and thus offers a comparatively better compatibility in resin matrix. Moreover, TGA analysis of this salt product indicated that there was 3% weight losing at 335°C under N2 atmosphere.
  • the calcium melamine phosphorous salts obtained from Examples 1 -4 were each tested as flame retardants for epoxy resins. Specifically, various resin samples were prepared by mixing the calcium melamine phosphorous salts with glass fiber and selected monomer (see Table 1 ), in the injection moulding machine, subsequently cured and then extruded in granulate form. For comparison, additional two resin samples were prepared in the same manner, only without addition of the calcium melamine phosphorous salts according to the invention (see CE 1 and CE 2 in Table 1). The flame retardancy performance of these resin samples were tested according to the UL94 vertical burning test procedure, using a sample thickness of both 1.6 mm and 0.8 mm.
  • Test Example 2 Comparison of the Flame Retardant Capacity of Example 1 and MPP
  • Example 1 achieved equally good fire retardancy as the MPP-added sample, and notably improved physical properties than the latter.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fireproofing Substances (AREA)

Abstract

Procédé de préparation d'un mélange de dérivés de mélamine, comprenant les étapes consistant à : premièrement, faire réagir au moins un composé contenant de l'azote et un phosphite métallique ou sel de phosphite d'hydrogène dans une solution aqueuse; et deuxièmement, chauffer le mélange réactionnel sous forme solide, ainsi obtenu, à une température comprise entre 150 et 500 °C en présence d'un oxydant, pour obtenir un mélange de dérivés de mélamine. Le mélange de dérivés de mélamine ainsi obtenu s'avère être utile comme ignifugeant dans des polymères époxy et contribue à maintenir les propriétés physiques de ces derniers.
PCT/CN2014/084589 2013-08-23 2014-08-18 Retardateur de flamme préparé à partir de dérivés d'amide et son procédé de préparation WO2015024487A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201480046748.3A CN105492520B (zh) 2013-08-23 2014-08-18 由酰胺衍生物制备的阻燃剂及其制造方法
KR1020167007213A KR102300270B1 (ko) 2013-08-23 2014-08-18 아미드 유도체로부터 제조된 난연제 및 그의 제조 방법

Applications Claiming Priority (2)

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CN2013082132 2013-08-23
CNPCT/CN2013/082132 2013-08-23

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3517566A4 (fr) * 2017-11-22 2019-12-11 Jiangsu Liside New Material Co., Ltd. Système de composé ignifuge sans halogène pour nylon renforcé par des fibres de verre et application de celui-ci dans un matériau de nylon renforcé par des fibres de verre sans halogène
DE102021202508A1 (de) 2021-03-15 2022-09-15 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Verwendung einer Stabilisatorzusammensetzung zur Stabilisierung von Polyolefin-Recyclaten, Stabilisatorzusammensetzung, Masterbatchkonzentrat, Kunststoffzusammensetzung, Formmasse oder Formteil, Verfahren zur Stabilisierung eines Polyolefin-Recyclats sowie Verwendung einer Kunststoffzusammensetzung

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
KR102403254B1 (ko) 2022-03-11 2022-05-26 정종헌 건축재용 친환경 난연 조성물 및 이의 제조 방법

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US4879327A (en) * 1987-03-31 1989-11-07 Atochem New phosphorous acid salts, compositions containing them, and their application as fireproofing agents

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JP4304510B2 (ja) * 2004-02-16 2009-07-29 信越化学工業株式会社 難燃性添加剤、並びにエマルション型コーティング剤及び難燃性組成物
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US4879327A (en) * 1987-03-31 1989-11-07 Atochem New phosphorous acid salts, compositions containing them, and their application as fireproofing agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3517566A4 (fr) * 2017-11-22 2019-12-11 Jiangsu Liside New Material Co., Ltd. Système de composé ignifuge sans halogène pour nylon renforcé par des fibres de verre et application de celui-ci dans un matériau de nylon renforcé par des fibres de verre sans halogène
JP2020504188A (ja) * 2017-11-22 2020-02-06 ジィァンスー リースーデェァ ニュー マテリアル カンパニー リミテッド ガラス繊維増強ナイロン用ハロゲンを含まない難燃再配合システム、およびハロゲンを含まない難燃ガラス繊維増強ナイロン材料中における活用
DE102021202508A1 (de) 2021-03-15 2022-09-15 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Verwendung einer Stabilisatorzusammensetzung zur Stabilisierung von Polyolefin-Recyclaten, Stabilisatorzusammensetzung, Masterbatchkonzentrat, Kunststoffzusammensetzung, Formmasse oder Formteil, Verfahren zur Stabilisierung eines Polyolefin-Recyclats sowie Verwendung einer Kunststoffzusammensetzung
WO2022194672A1 (fr) 2021-03-15 2022-09-22 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Utilisation d'une composition stabilisante pour stabiliser des recyclats de polyoléfine, composition de stabilisant, concentré de mélange maître, composition de matière plastique, composé de moulage ou moulage, procédé de stabilisation recyclat de polyoléfine et utilisation d'une composition de matière plastique

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KR20160045796A (ko) 2016-04-27

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