EP2991995A1 - Dérivés de di-dopo liés oar butadièn-2,3-diyle en tant que retardateurs de flamme - Google Patents

Dérivés de di-dopo liés oar butadièn-2,3-diyle en tant que retardateurs de flamme

Info

Publication number
EP2991995A1
EP2991995A1 EP14729157.9A EP14729157A EP2991995A1 EP 2991995 A1 EP2991995 A1 EP 2991995A1 EP 14729157 A EP14729157 A EP 14729157A EP 2991995 A1 EP2991995 A1 EP 2991995A1
Authority
EP
European Patent Office
Prior art keywords
parts
weight
compound
alkyl
composition
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP14729157.9A
Other languages
German (de)
English (en)
Inventor
Scott Edward ANGELL
Kimberly A. WHITE
Yu Li ANGLELL
Arthur G. Mack
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Angell Scott Edward
Anglell Yu Li
Mack Arthur G
WHITE, KIMBERLY A.
Albemarle Corp
Original Assignee
Anglell Yu Li
Angell Scott Edward
Mack Arthur G
Albemarle Corp
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 Anglell Yu Li, Angell Scott Edward, Mack Arthur G, Albemarle Corp filed Critical Anglell Yu Li
Publication of EP2991995A1 publication Critical patent/EP2991995A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus

Definitions

  • all the foregoing groups derived from hydrocarbons may have up to about 1 to about 20 carbon atoms (e.g., C1-C2 0 alkyl, C6-C2 0 aryl, C7-C2 0 alkaryl, C7-C2 0 aralkyl) or 1 to about 12 carbon atoms (e.g., C1-C12 alkyl, C 6 -Ci2 aryl, C7-C12 alkaryl, C7-C12 aralkyl), or 1 to about 8 carbon atoms, or 1 to about 6 carbon atoms.
  • carbon atoms e.g., C1-C2 0 alkyl, C6-C2 0 aryl, C7-C2 0 alkaryl, C7-C2 0 aralkyl
  • 1 to about 12 carbon atoms e.g., C1-C12 alkyl, C 6 -Ci2 aryl, C7-C12 alkaryl,
  • Polystyrene and graft copolymers of styrene for example styrene on polybutadiene, styrene and acrylonitrile on polybutadiene, styrene and alkyl acrylates or methacrylates on polybutadiene, styrene and acrylonitrile on ethylene/propylene/diene terpolymers, styrene and acrylonitrile on polyacrylates or polymethacrylates, styrene and acrylonitrile on acrylate/butadiene copolymers, as well as mixtures thereof with random copolymers of styrene or a-methylstyrene with dienes or acrylic derivatives, for instance the terpolymers of styrene known as ABS, MBS, ASA or AES terpolymers.
  • Epoxy resins are compounds that are prepared by polyaddition reaction of an epoxy resin component and a crosslinking (hardener) component.
  • the epoxy resin components used are aromatic polyglycidyl ethers such as bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, polyglycidyl ethers of phenol-formaldehyde resins and of cresol-formaldehyde resins, polyglycidyl ethers of phthalic, isophthalic and terephthalic acid, and also of trimellitic acid, N-glycidyl compounds of aromatic amines and of heterocyclic nitrogen bases, and also di- and polyglycidyl compounds of polyhydric aliphatic alcohols.
  • the flame-retardant additive of Formula I may be incorporated into the polymer by a variety of mixing techniques, such as solution blending and melt blending.
  • melt blending equipment include twin screw extruders, single screw extruders, Banbury mixers, roll mixers, kneaders, etc.
  • the melt blending temperature depends on the resin being used and is within the range from about 150°C to about 400°C.
  • the extrudate exits through small die holes, and the strands of molten composition are cooled by passing through a water bath.
  • the cooled strands can be pelletized.
  • the pellets can be used to prepare molded articles. In some instances, it is necessary to dry the composition prior to molding.
  • a further technique is to add the flame- retardant to finished polymer granules or powders and to process the mixture directly to provide a plastic article.
  • the method used in producing a plastic article from the flame-retardant resin composition of the present invention is not particularly limited, and any method commonly used may be employed. Exemplary such methods include moldings such as injection molding, blow molding, extrusion, sheet forming, thermal molding, rotational molding, and lamination.
  • Preferred cyanate ester monomers from which the triazines are prepared include bisphenol-A cyanate esters, bisphenol-E cyanate esters, tetramethylbisphenol-F cyanate esters, bisphenol-M cyanate esters, phenol Novolac cyanate esters, bisphenol-C cyanate esters, dicyclopentadienyl-bisphenol cyanate esters, Novolac cyanate esters, and the like, as well as mixtures of any two or more thereof.
  • Polybenzoxazines are made from benzoxazine monomer, which upon heating or curing, causes the heterocyclic oxazine ring to open forming the polymer where the nitrogen is in the main chain of the polymer.
  • the epoxy resin can be selected from known epoxy resins. Examples thereof include a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a biphenyl type epoxy resin, a phenol novolak type epoxy resin, a cresol novolak type epoxy resin, a xylene novolak type epoxy resin, triglycidyl isocyanurate, an alicyclic epoxy resin, a dicyclopentadiene.
  • the above epoxy resin curing agent can be selected from generally known epoxy resin curing agents. Examples thereof include imidazole derivatives such as 2- methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, l-cyanoethyl-2- phenylimidazole, 1 -cyanoethyl-2-ethyl-4-methylimidazole, 2-phenyl-4,5 - dihydroxymethylimidazole and 2-phenyl-4-methyl-5-hydroxymethylimidazole; amine compounds such as dicyandiamide, benzyldimethylamine and 4-methyl-N,N- dimethylbenzylamine; and phosphine compounds such as phosphonium compounds.
  • imidazole derivatives such as 2- methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, l-cyanoethyl-2- phenylimidazole, 1 -cyanoethyl
  • Polyphenylene oxide also called polyphenylene ether
  • exemplary polyphenylene oxides have the structure: [-Ph-0-] n wherein Ph is an optionally substituted phenyl ring, and n falls in the range of about 10 up to about 200; with n in the range of about 10-100 is preferred.
  • Ph is an optionally substituted phenyl ring
  • n falls in the range of about 10 up to about 200; with n in the range of about 10-100 is preferred.
  • SB styrene-butadiene
  • SBS styrene-butadiene-styrene
  • FG1901X and FG 1924 from Kraton Polymers
  • ethylene propylene diene monomer liquid rubbers and vinyl-terminated polybutadiene rubber
  • the average particle diameter of the inorganic filler is preferably 0.1 to 10 um. Inorganic fillers having different particle size distributions or different average particle diameters may be used in combination as required.
  • the amount of the inorganic filler is not specially limited. The amount of the inorganic filler per 100 parts by weight of the resin components is preferably 10 to 300 parts by weight, particularly preferably 30 to 200 parts by weight.
  • the lamination step is usually carried out for a time of from 1 minute to 200 minutes, and most often for 45 minutes to 120 minutes.
  • the lamination step may optionally be carried out at higher temperatures for shorter times (such as in continuous lamination processes) or for longer times at lower temperatures (such as in low energy press processes).
  • the solvent for the epoxy resin in step A above is a ketone such as 2- butanone or methyl ethyl ketone (MEK).
  • MEK methyl ethyl ketone
  • any other suitable type of conventionally-used solvent for forming these formulations can be employed.
  • such other solvents include, but are not limited to acetone, methyl isobutyl ketone (MIBK), 2-methoxy ethanol, l-methoxy-2-propanol, propylene glycol monomethyl ether, ethylene glycol monoethyl ether acetate, toluene, ⁇ , ⁇ -dimethylformamide, and mixtures thereof.
  • the curing or polymerization initializing agents that may be used for preparing the laminates are not limited to a specific curing or polymerization initializing agent as long as the agent helps polymerization of the epoxy resin in the flame-retardant epoxy composition.
  • the amount of curing agent that may be used is based on the molar equivalence of curing functional groups in the curing agent to the molar equivalence of un-reacted epoxy groups in the phosphorus-containing epoxy resin.
  • the curing agent amount may be from about 0.1 equivalence to about 10 equivalence or about 0.3 equivalence to about 5 equivalence, or about 0.7 equivalence to about 2 equivalence based on the equivalence of unreacted epoxy groups in the phosphorus-containing epoxy resin.
  • the amount of Flame retardant of Formula I used in the laminate or composite formulation is typically about 1% to about 30wt%, or about 3% to about 25wt%, or about 5% to about 20wt%, based on the total weight of the resins in the composite or laminate formulation.
  • compositions comprises (a) 10-50 parts by weight of at least one cyanate ester, (b) 10-50 parts by weight of at benzoxazine monomer; (c) 10-50 parts by weight of at least one bismaleimide, (d) 10-100 parts by weight of at least one epoxy compound; and (e) 5-60 parts by weight of the phosphorus compound having formula I.
  • the present invention also relates to a thermoset composition
  • a thermoset composition comprising: (a) 30-100 parts by weight of at least styrene -butadiene (SB) rubber, (b) 0-50 parts by weight of a styrene-butadiene-styrene (SBS) rubber; (c) 0-50 parts by weight of at least one bismaleimide, (d) 0-50 parts by weight of a maleic anhydride grafted styrene-butadiene polymer; ( e) 0-50 parts of an ethylene propylene diene monomer liquid rubber, (f) 0-50 parts of a vinyl -terminated polybutadiene rubber and (g) 0-50 parts of a polyphenylene oxide resin and (h) 5-60 parts of the phosphorus compound of Formula I .
  • SB styrene -butadiene
  • SBS styrene-butadiene-styrene
  • the compounds of the present invention may be produced by reacting approximately 2 equivalents of the chloro-dopo compound of Formula A with approximately one equivalent of the butyne diol compound of Formula B, optionally in presence of a base to neutralize the HC1 produced and an optional solvent, to form the compound of the present invention, wherein R 1 , R 2 and R 3 are defined above.
  • the reaction temperature may be from about - 20°C to about 100°C.
  • Any suitable optional base may be used to neutralize the HC1 produced in the reaction including organic or inorganic bases.
  • any optional suitable solvent may be used in the reaction.
  • suitable solvent may include: include, but are not limited to heptane, hexane, chloroform, chlorobenzene, petroleum ether, methylcyclohexane; dichloromethane, toluene, xylenes, ethyl benzene, tetrahydrofuran, DMSO, 1,4-dioxane, acetonitrile, ethylene glycol dimethyl ether, ethylene glycol diethyl ether or mixtures thereof.
  • a 4000-mL, 5-neck reaction vessel with circulating oil jacket was equipped with a mechanical stirrer, a condenser, a thermocouple, and a 1000-ml addition funnel.
  • the addition funnel was equipped with a short section of Teflon tubing for smooth delivery to the reactor and a glass plug at the top.
  • a nitrogen line with a bubbler was fitted to the top of the condenser.
  • DOPO-C1 (531.63g, 2.266mol) was dissolved in dichloromethane (1645g) and transferred to the reactor.
  • the oil jacket of the reaction vessel was cooled to -15°C.
  • the condenser was cooled to 10°C. Once the thermocouple indicated that the interior temperature of the reaction vessel was 0°C, the solution was slowly added to the reaction vessel to maintain a temperature of less than 15°C. After addition, the mixture was allowed to come to room temperature.
  • An 11 inch by 11 inch square woven glass fabric (7628 glass with 643 finish from BGF Industries) was cut to size from a large roll and stapled to wood supports (12 inches long, 1 inch wide and 1/16 inch thick) on the top and bottom ends of the fabric.
  • the wood supports contained holes in the corners for inserting paper clips on one end for hanging the fabric in the B-stage oven.
  • the A-stage, or resin varnish, was painted on the front and back of the fabric. Paper clips were unfolded and inserted into the both holes of one wood support.
  • compositions are processed according to the following procedure.
  • YPXTM 100F is a polypheny lene ether from Mitsubishi Gas Chemical Co.
  • DelacalTM NFR HP is a nitrogen synergists comprising constituents of Melem and Melam from Delamin Limited.
  • MGZ-6R is a silica coated magnesium hydroxide from Sakai Chemicals.
  • SMA® 1000 is a styrene-maleic anhydride copolymer with styrene/maleic anhydride molar ratios of 1 : 1 from Cray Valley USA.
  • Kraton ⁇ D-1118 a styrene-butadierie (SB) diblock copolymer (20%) and styrene- butadiene-styrene (SBS) tri block copolymer (80%) from Kraton Polymers.
  • SB styrene-butadierie
  • SBS styrene- butadiene-styrene
  • BM-200 is 4,4- dipbeny] methane bismaleimide from Otsuka Chemical.
  • YPXTM 100F is a polyphenylene ether from Mitsubishi Gas Chemical Co. Ricon® 156MA17 from Sartomer (subsidiary of the Arkema group) is a polybutadiene resin with maleic anhydride additions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Reinforced Plastic Materials (AREA)
  • Fireproofing Substances (AREA)

Abstract

La présente invention concerne de nouveaux retardateurs de flamme exempts d'halogène, dérivés du 9,10-dihydro-9-oxa-10-phosphaphénanthrène-10-oxyde (DOPO) de la structure ci-après : Cette invention concerne également l'utilisation des compositions dérivées de DOPO exemptes d'halogène en tant que retardateurs de flamme dans des polymères, et un procédé de préparation des composés ci-dessus par réaction d'un composé de formule A avec un composé de formule B :
EP14729157.9A 2013-05-03 2014-05-02 Dérivés de di-dopo liés oar butadièn-2,3-diyle en tant que retardateurs de flamme Withdrawn EP2991995A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361819326P 2013-05-03 2013-05-03
PCT/US2014/036579 WO2014179688A1 (fr) 2013-05-03 2014-05-02 Dérivés de di-dopo liés oar butadièn-2,3-diyle en tant que retardateurs de flamme

Publications (1)

Publication Number Publication Date
EP2991995A1 true EP2991995A1 (fr) 2016-03-09

Family

ID=50897928

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14729157.9A Withdrawn EP2991995A1 (fr) 2013-05-03 2014-05-02 Dérivés de di-dopo liés oar butadièn-2,3-diyle en tant que retardateurs de flamme

Country Status (6)

Country Link
EP (1) EP2991995A1 (fr)
JP (1) JP2016529205A (fr)
CA (1) CA2911382A1 (fr)
SG (1) SG11201509015YA (fr)
TW (1) TW201500368A (fr)
WO (1) WO2014179688A1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104558684A (zh) * 2015-01-21 2015-04-29 三峡大学 一种含dopo的双氧己内磷酸酯阻燃剂，制备方法及其应用
JP6819921B2 (ja) * 2016-03-15 2021-01-27 三菱瓦斯化学株式会社 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板
CN107325128B (zh) * 2017-07-05 2019-04-02 中国科学院宁波材料技术与工程研究所 一种DiDOPO类化合物的制备方法
JP7100799B2 (ja) * 2018-01-12 2022-07-14 昭和電工マテリアルズ株式会社 熱硬化性樹脂組成物、プリプレグ、積層板、プリント配線板及び高速通信対応モジュール
JP7274114B2 (ja) * 2018-01-12 2023-05-16 株式会社レゾナック 熱硬化性樹脂組成物、プリプレグ、積層板、プリント配線板及び高速通信対応モジュール
CN109161000A (zh) * 2018-07-27 2019-01-08 武汉工程大学 一种新型化合物dopo-ma在环氧树脂体系中的应用
CN109721710A (zh) * 2018-07-27 2019-05-07 武汉工程大学 一种新型化合物dopo-ma及其合成方法
CN109796688A (zh) * 2018-12-31 2019-05-24 安徽天康(集团)股份有限公司 一种云母带矿物绝缘波纹铜护套防火阻燃电缆
CN111635616B (zh) * 2019-03-01 2021-07-30 广东生益科技股份有限公司 无卤阻燃热固性树脂组合物、印刷电路用预浸料及覆金属层压板
CN110964320B (zh) * 2019-12-25 2022-06-07 艾蒙特成都新材料科技有限公司 一种阻燃马来酰亚胺组合物及其覆铜板的制备方法
TWI757816B (zh) * 2020-08-05 2022-03-11 國立中興大學 磷系化合物及其製備方法、阻燃不飽和樹脂組成物及固化物
CN113322533B (zh) * 2021-06-28 2022-11-22 中车青岛四方机车车辆股份有限公司 一种本征阻燃聚乙烯醇纤维及其制备方法
KR102615736B1 (ko) * 2021-08-11 2023-12-20 세진하이텍(주) 열반사 단열재 판넬 및 이의 제조방법
WO2023145960A1 (fr) * 2022-01-31 2023-08-03 株式会社ダイセル Composition de résine thermodurcissable, composition de résine pour carte de circuit imprimé, et composition de résine pour substrat de carte de circuit imprimé

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI503339B (zh) * 2009-05-19 2015-10-11 Albemarle Corp Ｄｏｐｏ衍生的阻燃劑及環氧樹脂組合物
PL2552929T3 (pl) * 2010-03-31 2017-05-31 Albemarle Corporation Sposób wytwarzania związków pochodnych DOPO i ich kompozycja

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2014179688A1 *

Also Published As

Publication number Publication date
CA2911382A1 (fr) 2014-11-06
SG11201509015YA (en) 2015-11-27
WO2014179688A1 (fr) 2014-11-06
JP2016529205A (ja) 2016-09-23
TW201500368A (zh) 2015-01-01

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