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WO2015068418A1 - Composition de résine polyuréthane - Google Patents

Composition de résine polyuréthane Download PDF

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Publication number
WO2015068418A1
WO2015068418A1 PCT/JP2014/063550 JP2014063550W WO2015068418A1 WO 2015068418 A1 WO2015068418 A1 WO 2015068418A1 JP 2014063550 W JP2014063550 W JP 2014063550W WO 2015068418 A1 WO2015068418 A1 WO 2015068418A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurethane resin
resin composition
group
containing compound
polyisocyanate compound
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/JP2014/063550
Other languages
English (en)
Japanese (ja)
Inventor
泰範 藤本
俊樹 野田
望 繁中
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.)
DKS Co Ltd
Original Assignee
Dai Ichi Kogyo Seiyaku Co Ltd
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 Dai Ichi Kogyo Seiyaku Co Ltd filed Critical Dai Ichi Kogyo Seiyaku Co Ltd
Priority to CN201480012560.7A priority Critical patent/CN105026451A/zh
Publication of WO2015068418A1 publication Critical patent/WO2015068418A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/69—Polymers of conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/6576—Compounds of group C08G18/69
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates

Definitions

  • the present invention relates to a polyurethane resin composition.
  • Patent Document 1 A polyurethane resin composition containing a modified product of isocyanurate has been disclosed.
  • Patent Document 2 a urethane elastomer having improved workability and reactivity by using allophanate-modified, isocyanurate-modified and prepolymer of hexamethylene diisocyanate
  • Patent Document 3 prepolymer having allophanate group and isocyanurate group
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide a polyurethane resin composition having excellent thermal durability under a cooling and heating cycle.
  • the inventors of the present invention can solve the above problems by using a polyol having a specific structure, an isocyanate group-containing compound, and an inorganic filler as a polyurethane resin composition. As a result, the present invention has been completed.
  • the polyurethane resin composition of the present invention is a polyurethane resin composition containing a hydroxyl group-containing compound, an isocyanate group-containing compound and an inorganic filler (D), wherein the hydroxyl group-containing compound contains a polybutadiene polyol (A).
  • the isocyanate group-containing compound contains an isocyanurate-modified product (B) of a polyisocyanate compound and an allophanate-modified product (C) of a polyisocyanate compound, and the inorganic filler (D) contains alumina, aluminum hydroxide, It is at least one selected from the group consisting of aluminum nitride, boron nitride, magnesium hydroxide and magnesium oxide, and the blending amount of the inorganic filler (D) is 50 to 95% by mass with respect to the polyurethane resin composition. .
  • the polyurethane resin composition of the present invention is characterized in that the polyisocyanate compound is hexamethylene diisocyanate.
  • the polyurethane resin composition of the present invention is used for electric and electronic parts.
  • the polyurethane resin composition of the present invention By using the polyurethane resin composition of the present invention, it is possible to obtain a polyurethane resin excellent in thermal durability under a cold cycle.
  • the polyurethane resin composition of the present invention contains a hydroxyl group-containing compound, an isocyanate group-containing compound and an inorganic filler (D).
  • the hydroxyl group-containing compound used in the present invention contains polybutadiene polyol (A).
  • polybutadiene polyol (A) used in the present invention those conventionally known for use in polyurethane resins can be used, and the average hydroxyl value is preferably 20 to 120 mgKOH / g.
  • the blending amount of the polybutadiene polyol (A) is preferably 1 to 40% by mass, more preferably 1 to 35% by mass, and further preferably 2 to 30% by mass with respect to the polyurethane resin composition. preferable.
  • the hydroxyl group-containing compound used in the present invention contains a castor oil-based polyol (E). Since it contains two types of polyol compounds, the polybutadiene polyol (A) and the castor oil-based polyol (E), the compatibility of the polyurethane resin composition during mixing is excellent, and the heat of the polyurethane resin under the cold cycle The durability is better.
  • the castor oil-based polyol, castor oil, castor oil fatty acid, and polyols produced using hydrogenated castor oil or hydrogenated castor oil fatty acid hydrogenated to these can be used.
  • polyols examples include castor oil, a transesterification product of castor oil and other natural fats, a reaction product of castor oil and polyhydric alcohol, an esterification reaction product of castor oil fatty acid and polyhydric alcohol, and alkylene oxide added thereto.
  • examples include polymerized polyols.
  • the compounding amount of the castor oil-based polyol (E) is preferably 0 to 40% by mass, more preferably 2 to 35% by mass, and more preferably 3 to 30% by mass with respect to the polyurethane resin composition. Further preferred.
  • the polybutadiene polyol (A) and the castor oil-based polyol (E) are obtained by reacting with a polyisocyanate compound isocyanurate-modified product (B) and a polyisocyanate compound isocyanurate-modified product (C) under hydroxyl-excess conditions. It may be a urethane prepolymer.
  • the mixing ratio of the polybutadiene polyol (A) and the castor oil-based polyol (E) is preferably 100/0 to 40/60 (mass ratio).
  • the isocyanate group-containing compound used in the present invention contains an isocyanurate-modified product (B) of a polyisocyanate compound and an allophanate-modified product (C) of a polyisocyanate compound.
  • the polyurethane resin has excellent thermal durability under a cooling / heating cycle.
  • Examples of such isocyanurate-modified (B) and allophanate-modified (C) of polyisocyanate compounds include aliphatic polyisocyanate compounds, alicyclic polyisocyanate compounds, aromatic polyisocyanate compounds, and araliphatic polyisocyanate compounds. Isocyanurate modified and allophanate modified.
  • Aliphatic polyisocyanate compounds include tetramethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, 2-methylpentane- Examples include 1,5-diisocyanate and 3-methylpentane-1,5-diisocyanate.
  • alicyclic polyisocyanate compounds include isophorone diisocyanate, hydrogenated xylylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,4-cyclohexane diisocyanate, methylcyclohexylene diisocyanate, 1,3-bis (isocyanate methyl) cyclohexane, and the like. Is mentioned.
  • aromatic polyisocyanate compound examples include tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate (MDI), 4,4′-dibenzyl diisocyanate, 1, Examples include 5-naphthylene diisocyanate, xylylene diisocyanate, 1,3-phenylene diisocyanate, and 1,4-phenylene diisocyanate.
  • Examples of the araliphatic polyisocyanate compound include dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, ⁇ , ⁇ , ⁇ , ⁇ -tetramethylxylylene diisocyanate.
  • either or both of the polyisocyanate compound isocyanurate-modified product (B) and the polyisocyanate compound allophanate-modified product (C) may be used as the polyisocyanate compound isocyanurate-modified product (B) and
  • An isocyanate group-terminated urethane prepolymer obtained by reacting an allophanate-modified polyisocyanate compound (C) with a polybutadiene polyol (A) and / or a castor oil-based polyol (E) can also be used.
  • an aliphatic polyisocyanate compound or an alicyclic polyisocyanate compound is preferable, and an isocyanurate-modified product of hexamethylene diisocyanate is particularly preferable.
  • the polyisocyanate compound isocyanurate-modified product (B) and the polyisocyanate compound allophanate-modified product (C) may be used alone or in combination of two or more.
  • the polyurethane resin of the present invention preferably has a molar ratio (NCO / OH) of isocyanate groups to hydroxyl groups of 0.5 to 1.5. This is because if the molar ratio of isocyanate group to hydroxyl group is smaller than this range, curing failure may occur or the heat resistance of the resulting resin may be reduced, and if it exceeds this range, curing failure may occur.
  • Examples of the inorganic filler (D) used in the present invention include alumina, aluminum hydroxide, aluminum nitride, boron nitride, magnesium hydroxide, and magnesium oxide. Of these, alumina, magnesium oxide, aluminum nitride, and boron nitride are preferable because of excellent heat dissipation.
  • the compounding amount of the inorganic filler (D) is 50 to 95% by mass, preferably 50 to 90% by mass, and more preferably 60 to 85% by mass with respect to the polyurethane resin composition.
  • the blending amount of the inorganic filler (D) is less than the above range, the heat dissipation effect tends to be small. There is.
  • a plasticizer (F) can be blended with the polyurethane resin composition of the present invention.
  • plasticizers (F) examples include phthalic acid esters such as dioctyl phthalate, diisononyl phthalate, and diundecyl phthalate, adipic acid esters such as dioctyl adipate and diisononyl adipate, methyl acetyl ricinoleate, butyl acetyl ricinoleate, and acetyl.
  • Castor oil ester such as triglyceride triglyceride, triglyceride triglyceride acetylated, trimellitic ester such as trioctyl trimellitate, triisononyl trimellitate, tetraoctyl pyromellitate, tetraisononyl pyromellitate, etc.
  • trimellitic ester such as trioctyl trimellitate, triisononyl trimellitate, tetraoctyl pyromellitate, tetraisononyl pyromellitate, etc.
  • Pyromellitic acid ester such as triglyceride triglyceride, triglyceride triglyceride acetylated, trimellitic ester such as trioctyl trimellitate, triisononyl trimellitate, tetraoctyl pyromellitate, tetraisononyl pyromell
  • the blending amount is preferably 0.01 to 50% by mass, and more preferably 0.1 to 40% by mass with respect to the polyurethane resin composition.
  • polyols other than polybutadiene polyol (A) and castor oil-based polyol (E) can be blended with the polyol component used in the present invention to such an extent that the effects of the present invention are not impaired.
  • examples of such polyols include polyether polyols, polyester polyols, polycarbonate polyols, polyisoprene polyols, polybutadiene polyol hydrides, and polyisoprene polyol hydrides.
  • silane coupling agent examples include alkoxysilanes, vinyl group-containing silane coupling agents, epoxy group-containing silane coupling agents, methacryl group-containing silane coupling agents, and acrylic group-containing silane coupling agents.
  • the polyurethane resin composition of the present invention preferably has a thermal conductivity in the range of 0.5 to 3 W / m ⁇ K.
  • the polyurethane resin obtained from the polyurethane resin composition of the present invention has thermal durability under a cooling and heating cycle, it can be suitably used for electrical and electronic parts that generate heat.
  • electric and electronic parts include transformers such as transformer coils, choke coils, and reactor coils, and equipment control bases.
  • Electric and electronic parts using the polyurethane resin of the present invention can be used in electric washing machines, toilet seats, water heaters, water purifiers, baths, dishwashers, electric tools, automobiles, motorcycles, and the like.
  • polyurethane resin composition of the present invention and the polyurethane resin raw material composition of the present invention will be described in detail based on Examples and Comparative Examples.
  • “parts” and “%” represent “parts by mass” and “mass%”, respectively, unless otherwise specified.
  • Examples 1 to 22 and Comparative Examples 1 to 3 The polyurethane resin composition of each Example and each comparative example was prepared according to the formulation shown in Table 1.
  • components other than the isocyanurate-modified polyisocyanate compound (B), allophanate-modified polyisocyanate compound (C) and catalyst (H) were mixed with a mixer (trade name: Awa). And then mixed at 2000 rpm for 1 minute and then adjusted to 25 ° C. Subsequently, the polyisocyanate compound isocyanurate-modified product (B) adjusted to 25 ° C. and the polyisocyanate compound allophanate-modified product (C) are added to this mixture and mixed at 2000 rpm for 30 seconds using the same mixer. Thereby, the polyurethane resin composition of each Example was obtained.
  • Thermal conductivity The polyurethane resin composition was poured into a 6 cm ⁇ 12 cm ⁇ 1 cm mold, cured at 80 ° C. for 16 hours, then demolded, and then allowed to stand at 25 ° C. for 24 hours to test for thermal conductivity measurement. Created a piece. The thermal conductivity was measured by a probe method using a thermal conductivity meter (QTM-D3, manufactured by Kyoto Electronics Industry Co., Ltd.).
  • the polyurethane resin composition of the present invention has a mixed viscosity within a usable range and is excellent in compatibility. Furthermore, it can be seen that the resulting polyurethane resin has good thermal conductivity and thermal durability under a cold cycle.
  • Comparative Example 3 when only an allophanate modified product (C) of a polyisocyanate compound is used as an isocyanate group-containing compound, a polyurethane is obtained when a polyisocyanate compound that is not an isocyanurate modified product is used. It can be seen that the thermal durability of the resin at high temperatures and the thermal durability under a cold cycle are inferior.
  • the resulting polyurethane resin has excellent thermal durability and can be used in the fields of electrical products and electronic parts.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invnetion concerne une composition de résine polyuréthane possédant une excellente durabilité thermique lors d'un cycle de refroidissement/chauffage. La présente invention concerne une composition de résine polyuréthane comprenant un composé contenant un groupe hydroxyle, un composé contenant un groupe isocyanate et une charge minérale (D), le composé contenant un groupe hydroxyle comprenant un polybutadiène polyol (A), le composé contenant un groupe isocyanate comprenant un produit (B) modifié par un isocyanurate d'un composé de polyisocyanate et un produit (C) modifié par un allophanate d'un composé de polyisocyanate, la charge minérale (D) comprenant au moins un composé choisi dans le groupe constitué par l'alumine, l'hydroxyde d'aluminium, le nitrure d'aluminium, le nitrure de bore, l'hydroxyde de magnésium et l'oxyde de magnésium, et la quantité de charge minérale (D) ajoutée étant de 50 à 95% en masse par rapport à la quantité de la composition de résine polyuréthane.
PCT/JP2014/063550 2013-11-06 2014-05-22 Composition de résine polyuréthane Ceased WO2015068418A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201480012560.7A CN105026451A (zh) 2013-11-06 2014-05-22 聚氨基甲酸酯树脂组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013-229884 2013-11-06
JP2013229884A JP5550161B1 (ja) 2013-11-06 2013-11-06 ポリウレタン樹脂組成物

Publications (1)

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WO2015068418A1 true WO2015068418A1 (fr) 2015-05-14

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Country Link
JP (1) JP5550161B1 (fr)
CN (1) CN105026451A (fr)
MY (2) MY183834A (fr)
WO (1) WO2015068418A1 (fr)

Cited By (5)

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Publication number Priority date Publication date Assignee Title
JP5989219B1 (ja) * 2015-12-04 2016-09-07 サンユレック株式会社 ポリウレタン樹脂組成物
JP7198398B1 (ja) 2021-11-10 2023-01-04 東洋インキＳｃホールディングス株式会社 表面処理無機粒子、無機粒子含有組成物、熱伝導性硬化物、構造体および積層体
EP4368650A4 (fr) * 2021-09-28 2024-10-02 LG Chem, Ltd. Composition durcissable
EP4328252A4 (fr) * 2021-09-28 2024-10-02 LG Chem, Ltd. Composition durcissable
EP4328253A4 (fr) * 2021-09-28 2024-10-02 LG Chem, Ltd. Composition durcissable

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JP5784210B1 (ja) * 2014-11-21 2015-09-24 サンユレック株式会社 ポリウレタン樹脂組成物
JP5946555B1 (ja) * 2015-03-13 2016-07-06 サンユレック株式会社 ポリウレタン樹脂組成物
JP5897184B1 (ja) * 2015-05-12 2016-03-30 サンユレック株式会社 ポリウレタン樹脂組成物
JP6411280B2 (ja) * 2015-05-12 2018-10-24 サンユレック株式会社 ポリウレタン樹脂組成物、封止材及び電気電子部品
JP6539106B2 (ja) * 2015-05-13 2019-07-03 旭化成株式会社 ポリイソシアネート組成物及びその製造方法、硬化性組成物、硬化物、並びに硬化樹脂
JP6273235B2 (ja) * 2015-07-03 2018-01-31 サンユレック株式会社 ポリウレタン樹脂組成物
US20190338121A1 (en) * 2016-07-29 2019-11-07 Mitsui Chemicals, Inc, Polyurethane resin and production method thereof
JP2018141096A (ja) * 2017-02-28 2018-09-13 第一工業製薬株式会社 封止用ポリウレタン樹脂組成物および封止物
JP6905135B1 (ja) * 2020-09-29 2021-07-21 第一工業製薬株式会社 ポリウレタン樹脂組成物
KR102583626B1 (ko) * 2021-02-05 2023-10-04 주식회사 엘지화학 조성물
JP7315107B2 (ja) 2021-04-08 2023-07-26 株式会社レゾナック 熱伝導性ウレタン樹脂組成物及び硬化物

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JP5370736B2 (ja) * 2009-03-18 2013-12-18 日本ポリウレタン工業株式会社 ２液型ポリウレタン樹脂塗料用硬化剤およびその製造方法ならびに２液型ポリウレタン樹脂塗料
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WO2013054659A1 (fr) * 2011-10-12 2013-04-18 サンユレック株式会社 Composition de résine de polyuréthane pour une isolation électrique

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5989219B1 (ja) * 2015-12-04 2016-09-07 サンユレック株式会社 ポリウレタン樹脂組成物
WO2017094358A1 (fr) * 2015-12-04 2017-06-08 サンユレック株式会社 Composition de résine de polyuréthane
EP4368650A4 (fr) * 2021-09-28 2024-10-02 LG Chem, Ltd. Composition durcissable
EP4328252A4 (fr) * 2021-09-28 2024-10-02 LG Chem, Ltd. Composition durcissable
EP4328253A4 (fr) * 2021-09-28 2024-10-02 LG Chem, Ltd. Composition durcissable
JP7198398B1 (ja) 2021-11-10 2023-01-04 東洋インキＳｃホールディングス株式会社 表面処理無機粒子、無機粒子含有組成物、熱伝導性硬化物、構造体および積層体
WO2023085034A1 (fr) * 2021-11-10 2023-05-19 東洋インキＳｃホールディングス株式会社 Particules inorganiques traitées en surface, composition contenant des particules inorganiques, produit durci thermoconducteur, structure et stratifié
JP2023071146A (ja) * 2021-11-10 2023-05-22 東洋インキＳｃホールディングス株式会社 表面処理無機粒子、無機粒子含有組成物、熱伝導性硬化物、構造体および積層体

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CN105026451A (zh) 2015-11-04
JP2015089909A (ja) 2015-05-11
MY155770A (en) 2015-11-25
JP5550161B1 (ja) 2014-07-16
MY183834A (en) 2021-03-17

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