WO2016009716A1 - Composition de résine polyuréthane - Google Patents

Composition de résine polyuréthane Download PDF

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Publication number
WO2016009716A1
WO2016009716A1 PCT/JP2015/064434 JP2015064434W WO2016009716A1 WO 2016009716 A1 WO2016009716 A1 WO 2016009716A1 JP 2015064434 W JP2015064434 W JP 2015064434W WO 2016009716 A1 WO2016009716 A1 WO 2016009716A1
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Prior art keywords
polyurethane resin
resin composition
mass
containing compound
parts
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PCT/JP2015/064434
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English (en)
Japanese (ja)
Inventor
成相 廣瀬
梓 金井
敏樹 野田
泰範 藤本
望 繁中
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第一工業製薬株式会社
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Priority claimed from JP2014144655A external-priority patent/JP5854534B2/ja
Priority claimed from JP2014144654A external-priority patent/JP5854533B2/ja
Application filed by 第一工業製薬株式会社 filed Critical 第一工業製薬株式会社
Priority to CN201580035477.6A priority Critical patent/CN106661182A/zh
Publication of WO2016009716A1 publication Critical patent/WO2016009716A1/fr

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    • 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
    • C08G18/70—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
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to a polyurethane resin composition.
  • Patent Document 1 Conventionally, electronic circuit boards and electronic components have been sealed using polyurethane resin or the like in order to prevent external contamination (Patent Document 1). 2. Description of the Related Art In recent years, as electronic parts and the like have a longer life, they are used under a long period of time under wet heat, and therefore have been required to have excellent wet heat resistance.
  • the present inventors contain a polybutadiene polyol, a castor oil-based polyol, and an isocyanurate-modified product of a polyisocyanate compound that are sealed in a transformer case and have excellent thermal durability even in a high temperature environment.
  • a polyurethane resin composition has been disclosed (Patent Document 2).
  • a resin case may be used for the peripheral parts of the sealing material.
  • the chemical stress crack does not occur on the case such as the electronic substrate and the case material, but the chemical stress crack is generated in the polyurethane resin composition disclosed so far.
  • a chemical stress crack is a typical brittle fracture that occurs with a tensile stress that is less than the tensile strength of the resin case.
  • the chemical adheres to and contacts the location where the tensile stress occurs (where the load is applied). In some cases, this is a phenomenon in which cracks (crazes, cracks) occur due to the synergistic action of chemicals and stress over time.
  • the present invention has been made in view of the above-described problems, and provides a polyurethane resin composition that is excellent in moisture and heat resistance, flame retardancy, electrical insulation, and workability, and that does not easily cause chemical stress cracks in a resin case. This is the issue.
  • the polyurethane resin composition includes a polyol having a specific structure, an isocyanate group-containing compound, a specific and specific amount of metal hydroxide, and a specific amount. It has been found that the above-mentioned problems can be solved by using the plasticizer, and the present invention has been completed.
  • Polyurethane resin composition containing 1 part by mass to 30 parts by mass with respect to a total of 100 parts by mass of (2)
  • the isocyanate group-containing compound contains a polyisocyanate compound isocyanurate-modified product (B1), and 40 parts by mass of the metal hydroxide (C) with respect to 100 parts by mass of the polyurethane resin composition (X).
  • the hydroxyl group-containing compound (A) further contains a castor oil-based polyol (A2), and 40 parts by mass of the metal hydroxide (C) to 100 parts by mass of the polyurethane resin composition (X).
  • the polyurethane resin composition according to (1) which contains 80 parts by mass
  • (4) The polyurethane resin composition according to (3), wherein a mass ratio of the castor oil-based polyol (A2) and the metal hydroxide (C) is (A2) :( C) 1: 5 to 1:10
  • the polyurethane resin composition of the present invention contains a hydroxyl group-containing compound, an isocyanate group-containing compound, a metal hydroxide and a plasticizer.
  • the hydroxyl group-containing compound used in the present invention contains polybutadiene polyol (A1).
  • polybutadiene polyol (A1) 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 (A1) is preferably 3 to 25% by mass, more preferably 5 to 20% by mass with respect to the polyurethane resin composition.
  • the blending amount of the polybutadiene polyol (A1) is less than the above range, the moist heat resistance and electrical insulation tend to be lowered.
  • the blending amount is more than the above range, the mixing viscosity at the time of producing the polyurethane resin composition is increased, and the workability is improved. There is a tendency to decrease.
  • the isocyanate group-containing compound contains a polyisocyanate compound isocyanurate-modified product (B1), and 40 parts by mass of the metal hydroxide (C) with respect to 100 parts by mass of the polyurethane resin composition (X). Parts to 80 parts by weight, (Ii)
  • the hydroxyl group-containing compound (A) further contains a castor oil-based polyol (A2), Containing 40 to 80 parts by mass of the metal hydroxide (C) with respect to 100 parts by mass of the polyurethane resin composition (X); Can be given.
  • a castor oil-based polyol (A2) as the hydroxyl group-containing compound in any of the preferred embodiments (i) and (ii). In particularly preferred embodiment (ii), it is more preferred. Since it contains two types of polyol compounds, the polybutadiene polyol (A1) and the castor oil-based polyol (A2), it is preferable because the compatibility of the polyurethane resin composition is excellent.
  • castor oil-based polyol (A2) castor oil, castor oil fatty acid, and hydrogenated castor oil or hydrogenated castor oil fatty acid hydrogenated to these can be used.
  • examples of such polyols 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 viscosity of castor oil-based polyol (A2) at 25 ° C. is preferably 800 mPa ⁇ s or less, and more preferably 700 mPa ⁇ s or less.
  • the number of functional groups is preferably 1.0 to 3.0, more preferably 1.0 to 2.7. Preferably, it is 1.2 to 2.7. It is particularly preferable in the preferred embodiment (ii) that the number of functional groups is within these ranges.
  • the number of functional groups means the average number of hydroxyl groups calculated from the charged amount. If it is these ranges, the mixing viscosity at the time of manufacture of a polyurethane resin composition will become suitable, and workability
  • the blending amount of the castor oil-based polyol (A2) is preferably 3 to 25% by mass, more preferably 5 to 20% by mass with respect to the polyurethane resin composition.
  • the blending amount of the castor oil-based polyol (A2) is less than the above range, the mixing viscosity at the production of the polyurethane resin composition tends to be high, and the workability tends to be lowered.
  • the blending amount is more than the above range, the heat and humidity resistance tends to be lowered. There is.
  • the polybutadiene polyol (A1) and castor oil-based polyol (A2) may be a hydroxyl group-terminated urethane prepolymer obtained by reacting with the isocyanate group-containing compound (B).
  • the mixing ratio of the polybutadiene polyol (A1) and the castor oil-based polyol (A2) is preferably 10/90 to 90/10 (mass ratio). By making it in the said range, the compatibility at the time of mixing of a polyurethane resin composition becomes more favorable.
  • polyols other than polybutadiene polyol (A1) and castor oil-based polyol (A2) 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.
  • an isocyanurate-modified product (B1) of a polyisocyanate compound it is preferable to contain an isocyanurate-modified product (B1) of a polyisocyanate compound.
  • the isocyanate group-containing compound contains an isocyanurate-modified product of a polyisocyanate compound, the thermal durability of the polyurethane resin becomes excellent.
  • another polyisocyanate compound (B2) can be included in an isocyanate group containing compound.
  • Other isocyanate compounds are not particularly limited as long as they are other than isocyanurate-modified products, and examples include biuret-modified products, adduct-modified products, bifunctional modified products, and monomers.
  • the preferred embodiment (ii) preferably contains a polyisocyanate compound isocyanurate-modified product (B1), isocyanurate, allophanate, burette, or adduct-modified product.
  • the isocyanate group-containing compound contains an isocyanurate-modified product of a polyisocyanate compound, the thermal durability of the polyurethane resin becomes excellent. Although the reason is not clear, it can be inferred to be due to the hydrolysis-inhibiting effect of the isocyanurate-modified polyisocyanate compound.
  • the isocyanate group-containing compound may include other polyisocyanate compounds such as a bifunctional modified product and a monomer.
  • polyisocyanate compound examples include aliphatic polyisocyanate compounds, alicyclic polyisocyanate compounds, aromatic polyisocyanate compounds, and araliphatic polyisocyanate compounds.
  • the polyisocyanate compound is preferably an aliphatic polyisocyanate compound or an alicyclic polyisocyanate compound, more preferably an aliphatic polyisocyanate compound, and most preferably hexamethylene diisocyanate from the viewpoints of reactivity, durability, viscosity, and workability. .
  • 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.
  • the polyisocyanate compound is preferably an aliphatic polyisocyanate compound or an alicyclic polyisocyanate compound, more preferably an aliphatic polyisocyanate compound, and most preferably hexamethylene diisocyanate from the viewpoints of reactivity, durability, viscosity, and workability. .
  • an isocyanate group-terminated urethane prepolymer obtained by reacting a polyisocyanate compound with a polybutadiene polyol (A1) and / or a castor oil-based polyol (A2) can also be used as the polyisocyanate compound.
  • the molar ratio of isocyanate groups to hydroxyl groups is preferably 0.6 to 1.5, more preferably 0.7 to 1.3. 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.
  • the metal hydroxide (C) used in the present invention is, for example, aluminum hydroxide and / or magnesium hydroxide.
  • the compounding amount of the metal hydroxide (C) is preferably 40 to 80 parts by mass, and more preferably 45 to 78 parts by mass with respect to 100 parts by mass of the polyurethane resin composition (X). If the blending amount of the metal hydroxide (C) is less than the above range, the flame retardancy tends to decrease, and if it is more than the above range, the mixing viscosity at the time of production of the polyurethane resin composition increases and the workability decreases. Tend to.
  • the amount of castor oil-based polyol (A2) is larger than the above range, the heat and humidity resistance tends to decrease.
  • the amount of castor oil-based polyol (A2) is small, the mixed viscosity at the time of production of the polyurethane resin composition increases, and the workability tends to decrease. There is.
  • plasticizer (D) used in the present invention those conventionally known for use in polyurethane resins can be used.
  • examples of such a plasticizer include phthalic acid such as dioctyl phthalate, diisononyl phthalate, and diundecyl phthalate.
  • Esters such as dioctyl adipate and diisononyl adipate, castor oil esters such as methyl acetyl ricinoleate, butyl acetyl ricinoleate, acetylated ricinoleic acid triglyceride, acetylated polyricinoleic acid triglyceride, trioctyl trimellitate, triisononyl Trimellitic acid esters such as trimellitate, pyromellitic acid esters such as tetraoctyl pyromellitate, tetraisononyl pyromellitate, tricresyl phosphate, triski Les nil phosphate, cresyl diphenyl phosphate, carboxymethyl Les sulfonyl phosphate, and phosphoric acid esters such as triphenyl phosphate.
  • castor oil esters such as methyl acetyl ricino
  • phthalic acid ester, trimellitic acid ester, and phosphoric acid ester are preferred from the viewpoints of excellent heat and humidity resistance, flame resistance, electrical insulation, workability, and economic efficiency, and resistance to chemical stress cracks in the resin case.
  • a phthalic acid ester and a phosphoric acid ester are more preferable.
  • the compounding amount of the plasticizer (D) is 1 to 30 parts by mass with respect to a total of 100 parts by mass of the hydroxyl group-containing compound (A) and the plasticizer (D). From the viewpoints of excellent workability and workability and resistance to the occurrence of chemical stress cracks in the resin case, it is preferably 1 part by weight to 28 parts by weight, and more preferably 5 parts by weight to 25 parts by weight.
  • the mixing ratio of the polybutadiene polyol (A1) and the plasticizer (D) is preferably 100/4 to 100/35 (mass ratio), and preferably 100/7 to 100/30 (mass ratio). More preferred. By setting it within the above range, it is possible to obtain a polyurethane resin which has good workability and hardly causes chemical stress cracks in the resin case.
  • 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 mixed viscosity of the present invention is preferably 40,000 mPa.s or less, more preferably 30,000 mPa.s or less. Within these ranges, the workability is good. In addition, mixing viscosity is measured by the method as described in an Example.
  • the moisture and heat resistance of the present invention preferably retains a hardness of type A5 or more, more preferably retains a hardness of type A10 or more after 85 ° C. ⁇ 85% RH ⁇ 3000 hours. These ranges are good in terms of maintaining the resin shape.
  • the flame retardancy of the present invention is preferably V-1 level flame retardancy, more preferably V-0 level flame retardancy in the UL94 standard.
  • the electrical insulation of the present invention is preferably 10 8 ⁇ ⁇ cm or more, more preferably 10 9 ⁇ ⁇ cm or more after 85 ° C. ⁇ 85% RH ⁇ 3000 hours. Within these ranges, it is favorable in terms of electrical insulation.
  • the chemical stress crack resistance of the present invention is preferably 0.5% or more, more preferably 0.7% or more, at a critical strain after 25 ° C. ⁇ 60% RH ⁇ 48 hours. Within these ranges, it is favorable in that cracks do not occur in the housing and case material of the substrate.
  • 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.
  • A1-1 Polybutadiene polyol having an average hydroxyl value of 103 mgKOH / g (trade name: Poly bd R-15HT, manufactured by Idemitsu Kosan Co., Ltd.)
  • A1-2 Polybutadiene polyol having an average hydroxyl value of 47 mgKOH / g (trade name: Poly bd R-45HT, manufactured by Idemitsu Kosan Co., Ltd.)
  • A2-1 Castor oil fatty acid-polyhydric alcohol ester (divalent functional group) (Product name: URIC Y-403, manufactured by Ito Oil)
  • A2-2 Castor oil (2.7 functional groups) (Product name: castor oil, manufactured by Ito Oil Co., Ltd.)
  • A2-3 Castor oil fatty acid-alcohol ester (monovalent functional group) (Product name: URIC H-31, manufactured by Ito Oil)
  • B1 Isocyanurate modified product of hexamethylene diisocyanate (trade name: Duranate TLA-100, manufactured by Asahi Kasei Chemicals) (Other polyisocyanate compound (B2))
  • B2-1 Bifunctional modified product of hexamethylene diisocyanate (trade name: Duranate D201, manufactured by Asahi Kasei Chemicals Corporation)
  • B2-2 A modified burette of hexamethylene diisocyanate (trade name: Duranate 24A-100, manufactured by Asahi Kasei Chemicals Corporation)
  • B2-3 Adduct modified product of hexamethylene diisocyanate (trade name: Duranate AE700-100, manufactured by Asahi Kasei Chemicals Corporation)
  • B2-4 Polymeric MDI (Product name: Millionate MR-200, manufactured by Nippon Polyurethane Industry Co., Ltd.)
  • Metal hydroxide (C)) C1: Aluminum hydroxide (trade name: Aluminum hydroxide C-305, manufactured by Sumitomo Chemical Co., Ltd.)
  • C2 Magnesium hydroxide (manufactured by Tateho Chemical Co., Ltd.)
  • D1 Diundecyl phthalate (Brand name: SUNSOSIZER DUP, manufactured by Shin Nippon Rika Co., Ltd.)
  • D2 Trisoxylenyl phosphate (trade name: TXP, manufactured by Daihachi Chemical Industry Co., Ltd.)
  • Examples 1 to 23 and Comparative Examples 1 to 6 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 isocyanate group-containing compound (B) among the components shown in Table 1 were mixed for 3 minutes at 2000 rpm using a mixer (trade name: Aritori Nertaro, manufactured by Shinky Corp.), then 25 Adjusted to ° C. Then, the isocyanate group containing compound (B) adjusted to 25 degreeC was added to this mixture, and the polyurethane resin composition of each Example was obtained by mixing for 60 second at 2000 rpm using the mixer same as the above.
  • the flame retardancy was measured according to UL standard UL94 (flame retardance of plastic materials).
  • ABS test piece 1 (trade name: Kobe Poly Sheet ABS, manufactured by Shin-Kobe Electric Machinery Co., Ltd.) was attached to a 1/4 oval jig shown in FIG. After being attached to the surface of the test piece, the specimen was left in an environment of 25 ° C. ⁇ 60% for 48 hours, the position X at which a crack occurred was measured, and the critical strain value was obtained using Equation 1. Based on the critical strain value, the chemical stress crack resistance was evaluated by ranking as follows.
  • ⁇ critical strain value a: ellipse major axis 100 mm b: Ellipse minor axis 40mm
  • X Crack generation point Distance from the fixed end to the crack generation point with respect to the long axis of the test piece mm t: Test piece thickness 2.0 mm ⁇ Evaluation> ⁇ (The possibility of occurrence of crazes or cracks is small and can be used practically): Critical strain value ( ⁇ ) 0.7% or more ⁇ (The possibility of cracking is high in parts where molding strain is large or where stress concentration is high): Critical strain value ( ⁇ ) less than 0.7%
  • the polyurethane resin composition of the present invention has a range in which the mixed viscosity can be used, is excellent in workability, moist heat resistance, flame resistance, and electrical insulation, and is suitable for a resin case. It can be seen that chemical stress cracks are less likely to occur.
  • the polyurethane resin obtained from the polyurethane resin composition of the present invention has heat and moisture resistance, it can be suitably used for electric and electronic parts that generate heat.
  • electric and electronic parts include transformers such as transformer coils, choke coils, and reactor coils, and device control boards.
  • the 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, solar panels, electric tools, automobiles, motorcycles and the like.
  • the resulting polyurethane resin is less likely to cause chemical stress cracks in the resin case, and thus can be suitably used particularly in the field of electrical and electronic parts in which the resin case material is used.

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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 invention concerneune composition de résine polyuréthane présentant une résistance à la chaleur humide, un caractère ignifugeant, une isolation électrique et une aptitude au façonnage excellents et avec laquelle les fissures de tension chimique ne se produisent pas facilement dans un boîtier en résine correspondant. L'invention concerne une composition de résine polyuréthane (X) comprenant un composé contenant un groupe hydroxyle (A), un composé contenant un groupe isocyanate (B), un hydroxyde métallique (C) et un plastifiant (D) : le composé contenant un groupe hydroxyle comprenant un polyol de polybutadiène (A1) ; l'hydroxyde métallique étant de l'hydroxyde d'aluminium et/ou de l'hydroxyde de magnésium ; et la composition comprenant de 1 partie en masse à 30 parties en masse du plastifiant (D) par rapport à 100 parties en masse de la somme du composé contenant un groupe hydroxyle (A) et du plastifiant (D).
PCT/JP2015/064434 2014-07-15 2015-05-20 Composition de résine polyuréthane WO2016009716A1 (fr)

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