WO2024122297A1 - 難燃剤組成物、難燃性樹脂組成物および成形品 - Google Patents

難燃剤組成物、難燃性樹脂組成物および成形品 Download PDF

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Publication number
WO2024122297A1
WO2024122297A1 PCT/JP2023/041222 JP2023041222W WO2024122297A1 WO 2024122297 A1 WO2024122297 A1 WO 2024122297A1 JP 2023041222 W JP2023041222 W JP 2023041222W WO 2024122297 A1 WO2024122297 A1 WO 2024122297A1
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WO
WIPO (PCT)
Prior art keywords
mass
flame
parts
component
flame retardant
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.)
Ceased
Application number
PCT/JP2023/041222
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English (en)
French (fr)
Japanese (ja)
Inventor
佳 浅井
文彦 佐藤
久史 櫻井
圭亮 阪野
豊 米澤
総夫 中村
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.)
Adeka Corp
Original Assignee
Adeka 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 Adeka Corp filed Critical Adeka Corp
Priority to US19/135,870 priority Critical patent/US20260092163A1/en
Priority to CN202380084347.6A priority patent/CN120265730A/zh
Priority to JP2024562650A priority patent/JPWO2024122297A1/ja
Priority to EP23900418.7A priority patent/EP4632041A1/en
Priority to KR1020257022737A priority patent/KR20250120385A/ko
Publication of WO2024122297A1 publication Critical patent/WO2024122297A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00Fireproofing materials
    • C09K21/06Organic materials
    • C09K21/12Organic materials containing phosphorus
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462Six-membered rings
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477Six-membered rings
    • C08K5/3492Triazines
    • C08K5/34928Salts
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/52Phosphorus bound to oxygen only
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/53Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313Phosphinic compounds, e.g. R2=P(:O)OR'
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00Use of ingredients characterised by shape
    • C08K7/02Fibres or whiskers
    • C08K7/04Fibres or whiskers inorganic
    • C08K7/14Glass

Definitions

  • this flame retardant composition is configured so that the content of the (C) component is 0.2 parts by mass or more and 39 parts by mass or less, relative to 100 parts by mass of the total content of the (A) component, the (B) component, and the (C) component.
  • the ratio of phosphorus atoms to melamine in the melamine salt is not particularly limited, but from the standpoint of flame retardancy, it is preferable that the ratio be 0.5 to 2 moles of melamine per mole of phosphorus atoms, and more preferably 0.8 to 1.2 moles of melamine per mole of phosphorus atoms.
  • the component (C) may contain at least one compound in which R 1 and R 2 in the above general formula (1) are each independently any alkyl group having 2 to 4 carbon atoms.
  • M in the above general formula (1) is preferably one or more selected from the group consisting of Mg, Ca, Al, Fe, Zn, Na and K, more preferably one or more selected from the group consisting of Al, Fe, Zn and Na, even more preferably one or more selected from the group consisting of Al and Na, and particularly preferably Al.
  • the component (C) one type of compound may be used alone, or two or more types of compounds having different R 1 , R 2 and M in the general formula (1) may be used in combination.
  • the component (C) may contain at least one compound in which M in the general formula (1) is one type selected from the group consisting of Al, Fe, Zn and Na.
  • the manufacturing method of component (C) can be a known method.
  • methods for manufacturing dialkylphosphinate salts are disclosed in JP-T-2001-525327 and JP-A-2005-179362.
  • the content of the (C) component may be 2 parts by mass or more and 25 parts by mass or less, per 100 parts by mass of the total mass of the (A) component, the (B) component, and the (C) component.
  • the flame retardant composition of this embodiment may contain a surface treatment agent.
  • the surface treatment agent include silicone oil and a silane coupling agent.
  • silicone oil By using the silicone oil, it is possible to prevent the powdered flame retardant composition from agglomerating, improve the storage stability, and improve the dispersibility in synthetic resins. It is also possible to improve the water resistance.
  • the silicone oil can be any known silicone oil having a polysiloxane skeleton.
  • the silicone oil can be a polymer having a linear polysiloxane skeleton, and the side chain of the polysiloxane can be entirely methyl groups, or a part of the side chain can have a phenyl group, or a part of the side chain can have hydrogen.
  • silicone oil examples include dimethyl silicone oil, in which the side chain of polysiloxane and the terminal are all methyl groups, methylphenyl silicone oil, in which the side chain of polysiloxane and the terminal are methyl groups and part of the side chain is phenyl group, methyl hydrogen silicone oil, in which the side chain of polysiloxane and the terminal are methyl groups and part of the side chain is hydrogen, and copolymers thereof.
  • silicone oils may be partially modified by epoxy modification, amino modification, carboxy modification, etc.These may be used alone or in combination of two or more.
  • Light stabilizers include, for example, 2,2,6,6-tetramethyl-4-piperidyl stearate, 1,2,2,6,6-pentamethyl-4-piperidyl stearate, 2,2,6,6-tetramethyl-4-piperidyl benzoate, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl) methyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, bis(2,2,6,6-tetramethyl-4-piperidyl) bis(tridecyl)-1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-
  • cyanoacrylates such as aryl-2-cyano-3-methyl-3-(p-methoxyphenyl)acrylate
  • triaryltriazines such as 2-(2-hydroxy-4-octoxyphenyl)-4,6-bis(2,4-di-tert-butylphenyl)-s-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-s-triazine, and 2-(2-hydroxy-4-propoxy-5-methylphenyl)-4,6-bis(2,4-di-tert-butylphenyl)-s-triazine.
  • These ultraviolet absorbents can be used alone or in combination of two or more.
  • the flame retardant composition of the present invention is effective in making synthetic resins flame retardant, and is preferably used as a flame retardant resin composition when blended with synthetic resins.
  • thermoplastic resins can be used regardless of molecular weight, degree of polymerization, density, softening point, proportion of insoluble matter in solvent, degree of stereoregularity, presence or absence of catalyst residue, type and blending ratio of raw monomers, type of polymerization catalyst (e.g. Ziegler catalyst, metallocene catalyst, etc.).
  • type of polymerization catalyst e.g. Ziegler catalyst, metallocene catalyst, etc.
  • polyolefin resins one or more selected from the group consisting of polyolefin resins, polystyrene resins, and copolymers thereof are preferred, polyolefin resins are more preferred, polypropylene, high density polyethylene, low density polyethylene, and linear low density polyethylene are even more preferred, and it is also preferred to use them in combination with a thermoplastic elastomer.
  • a flame retardant composition containing the (A), (B) and (C) components (and, if necessary, the (D) component) was produced in the same manner as in the blending ratios shown in Table 1 of Examples 1 to 18, and then the flame retardant composition was blended with a polypropylene composition to obtain a flame retardant resin composition, which also showed evaluation results similar to those of Examples 1 to 18 above.
  • the flame retardant compositions of Examples 1 to 18 can improve the flame retardancy of a flame-retardant resin composition by blending them with a thermoplastic resin (polypropylene composition).
  • the flame retardant compositions of each Example reduced the injection pressure during injection molding, which shows that the processability of the thermoplastic resin can be improved.

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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)
PCT/JP2023/041222 2022-12-09 2023-11-16 難燃剤組成物、難燃性樹脂組成物および成形品 Ceased WO2024122297A1 (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US19/135,870 US20260092163A1 (en) 2022-12-09 2023-11-16 Flame-retardant composition, flame-retardant resin composition, and molded product
CN202380084347.6A CN120265730A (zh) 2022-12-09 2023-11-16 阻燃剂组合物、阻燃性树脂组合物和成型品
JP2024562650A JPWO2024122297A1 (https=) 2022-12-09 2023-11-16
EP23900418.7A EP4632041A1 (en) 2022-12-09 2023-11-16 Flame-retardant composition, flame-retardant resin composition and molded article
KR1020257022737A KR20250120385A (ko) 2022-12-09 2023-11-16 난연제 조성물, 난연성 수지 조성물 및 성형품

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022-196962 2022-12-09
JP2022196962 2022-12-09

Publications (1)

Publication Number Publication Date
WO2024122297A1 true WO2024122297A1 (ja) 2024-06-13

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PCT/JP2023/041222 Ceased WO2024122297A1 (ja) 2022-12-09 2023-11-16 難燃剤組成物、難燃性樹脂組成物および成形品

Country Status (7)

Country Link
US (1) US20260092163A1 (https=)
EP (1) EP4632041A1 (https=)
JP (1) JPWO2024122297A1 (https=)
KR (1) KR20250120385A (https=)
CN (1) CN120265730A (https=)
TW (1) TW202442862A (https=)
WO (1) WO2024122297A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2026041026A1 (en) * 2024-08-19 2026-02-26 Benecke Changshun Auto Trim (Zhangjiagang) Co., Ltd Thermoplastic polyolefin elastomer composition and artificial leather thereof

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001525327A (ja) 1997-11-28 2001-12-11 クラリアント・ゲゼルシヤフト・ミト・ベシユレンクテル・ハフツング ジアルキルホスフィン酸塩の製造方法
JP2005179362A (ja) 2003-12-19 2005-07-07 Clariant Gmbh ジアルキルホスフィン酸塩の製造方法
JP2008291217A (ja) 2007-03-29 2008-12-04 Clariant Internatl Ltd 難燃性にされた接着剤およびシーリング材
CN102775740A (zh) * 2012-07-24 2012-11-14 金发科技股份有限公司 一种无卤阻燃弹性体组合物
JP2014098125A (ja) 2012-11-16 2014-05-29 Unitika Ltd 熱可塑性樹脂組成物およびそれを成形してなる成形体
JP2014198778A (ja) 2013-03-29 2014-10-23 旭化成イーマテリアルズ株式会社 ポリフェニレンエーテル組成物
JP2016502505A (ja) * 2012-10-16 2016-01-28 カテナ アディティブス ゲーエムベーハー ウント コー.カーゲー 難燃性材料としてのアジン金属ホスフェート
JP2019038989A (ja) * 2017-08-23 2019-03-14 株式会社Adeka 難燃性エポキシ樹脂組成物
JP2020518594A (ja) * 2018-01-24 2020-06-25 キングファ サイエンス アンド テクノロジー カンパニーリミテッドKingfa Sci. & Tech. Co.,Ltd. アルミニウムアミノトリメチレンホスホネート、その調製方法及び応用
JP2022508243A (ja) * 2018-11-30 2022-01-19 クラリアント・インターナシヨナル・リミテツド 難燃剤混合物、難燃性ポリマー組成物、それを備えたケーブルおよびそれらの使用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101530833B1 (ko) 2011-11-17 2015-06-29 엘지전자 주식회사 무선 통신 시스템에서 데이터를 교환하는 방법 및 장치

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001525327A (ja) 1997-11-28 2001-12-11 クラリアント・ゲゼルシヤフト・ミト・ベシユレンクテル・ハフツング ジアルキルホスフィン酸塩の製造方法
JP2005179362A (ja) 2003-12-19 2005-07-07 Clariant Gmbh ジアルキルホスフィン酸塩の製造方法
JP2008291217A (ja) 2007-03-29 2008-12-04 Clariant Internatl Ltd 難燃性にされた接着剤およびシーリング材
CN102775740A (zh) * 2012-07-24 2012-11-14 金发科技股份有限公司 一种无卤阻燃弹性体组合物
JP2016502505A (ja) * 2012-10-16 2016-01-28 カテナ アディティブス ゲーエムベーハー ウント コー.カーゲー 難燃性材料としてのアジン金属ホスフェート
JP2014098125A (ja) 2012-11-16 2014-05-29 Unitika Ltd 熱可塑性樹脂組成物およびそれを成形してなる成形体
JP2014198778A (ja) 2013-03-29 2014-10-23 旭化成イーマテリアルズ株式会社 ポリフェニレンエーテル組成物
JP2019038989A (ja) * 2017-08-23 2019-03-14 株式会社Adeka 難燃性エポキシ樹脂組成物
JP2020518594A (ja) * 2018-01-24 2020-06-25 キングファ サイエンス アンド テクノロジー カンパニーリミテッドKingfa Sci. & Tech. Co.,Ltd. アルミニウムアミノトリメチレンホスホネート、その調製方法及び応用
JP2022508243A (ja) * 2018-11-30 2022-01-19 クラリアント・インターナシヨナル・リミテツド 難燃剤混合物、難燃性ポリマー組成物、それを備えたケーブルおよびそれらの使用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP4632041A1

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2026041026A1 (en) * 2024-08-19 2026-02-26 Benecke Changshun Auto Trim (Zhangjiagang) Co., Ltd Thermoplastic polyolefin elastomer composition and artificial leather thereof

Also Published As

Publication number Publication date
EP4632041A1 (en) 2025-10-15
TW202442862A (zh) 2024-11-01
JPWO2024122297A1 (https=) 2024-06-13
US20260092163A1 (en) 2026-04-02
KR20250120385A (ko) 2025-08-08
CN120265730A (zh) 2025-07-04

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