WO2019163621A1 - Composition de résine thermofusible de polyuréthane durcissable à l'humidité, et objet durci associé - Google Patents

Composition de résine thermofusible de polyuréthane durcissable à l'humidité, et objet durci associé Download PDF

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Publication number
WO2019163621A1
WO2019163621A1 PCT/JP2019/005248 JP2019005248W WO2019163621A1 WO 2019163621 A1 WO2019163621 A1 WO 2019163621A1 JP 2019005248 W JP2019005248 W JP 2019005248W WO 2019163621 A1 WO2019163621 A1 WO 2019163621A1
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WIPO (PCT)
Prior art keywords
moisture
resin composition
polyurethane hot
curable polyurethane
melt resin
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PCT/JP2019/005248
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English (en)
Japanese (ja)
Inventor
淳 二宮
豊邦 藤原
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Dic株式会社
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Priority to JP2019545827A priority Critical patent/JP6631863B1/ja
Publication of WO2019163621A1 publication Critical patent/WO2019163621A1/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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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

Definitions

  • the present invention relates to a moisture curable polyurethane hot melt resin composition and a cured product thereof.
  • Moisture curable polyurethane hot melt resin compositions are widely used as various adhesives. When the moisture curable polyurethane hot melt resin composition is used as various adhesives, it is required to obtain good adhesive strength (initial strength) immediately after the adhesive is applied. However, since the moisture curable polyurethane hot melt resin composition exhibits adhesive strength by moisture curing, it has been difficult to exhibit excellent initial strength.
  • the moisture-curable polyurethane hot melt resin composition having excellent initial strength for example, a method using a crystalline polyester polyol or a polyester polyol having a high glass transition temperature is known (see, for example, Patent Document 1). ). However, in these methods, since the obtained cured film is hardened, there is a problem that the use is limited.
  • the problem to be solved by the present invention is to provide a moisture curable polyurethane hot melt resin composition having excellent initial strength.
  • the present invention provides a reaction product of a polyol (A) and a polyisocyanate (B) containing a compound (a1) having a number average molecular weight of less than 500, a branched structure, and having 2 to 4 hydroxyl groups in one molecule.
  • the present invention provides a moisture curable polyurethane hot melt resin composition comprising a urethane prepolymer having an isocyanate group.
  • this invention provides the hardened
  • the moisture curable polyurethane hot melt resin composition of the present invention is excellent in initial strength. Furthermore, when a specific polyol is used as the polyol (A), a moisture-curable polyurethane hot melt resin composition having excellent low viscosity and flexibility can be obtained.
  • the moisture-curable polyurethane hot melt resin composition of the present invention has a polyol (A1) having a number average molecular weight of less than 500, a branched structure, and a compound (a1) having 2 to 4 hydroxyl groups in one molecule. And a urethane prepolymer having an isocyanate group which is a reaction product of polyisocyanate (B).
  • the compound (a1) has a number average molecular weight of less than 500, a branched structure, and 2 to 4 hydroxyl groups per molecule.
  • the urethane group concentration of the urethane prepolymer is improved, and the initial cohesive force is improved due to steric hindrance due to the branched structure. Therefore, a crystalline polyester polyol or a polyester polyol having a high glass transition temperature. Even without using, it is possible to obtain excellent initial strength and initial creep properties.
  • cured film obtained by this can also be designed, the utilization range of a moisture hardening type polyurethane hot-melt resin composition can be expanded.
  • the number average molecular weight of the compound (a1) is a value calculated from the chemical formula.
  • Examples of the compound (a1) include 2-methyl-1,5-pentanediol, 3-methyl-1,5-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 2,4 -Diethyl-1,5-pentanediol, 1,2-butanediol, 1,3-butanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,2-propanediol, 2-methyl- 1,3-propanediol, 2-ethyl-1,3-hexanediol, neopentyl glycol, 2-isopropyl-1,4-butanediol, 2,4-dimethyl-1,5-pentanediol, 2-ethyl- 1,6-hexanediol, 3,5-heptanediol, 2-methyl-1,8-octanediol
  • These compounds may be used alone or in combination of two or more.
  • Pentanediol 2,4-diethyl-1,5-pentanediol, 1,2-butanediol, 1,3-butanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,2-propane It is preferable to use one or more compounds selected from the group consisting of diol, 2-methyl-1,3-propanediol, 2-ethyl-1,3-hexanediol, neopentyl glycol, and trimethylolpropane.
  • the amount of the compound (a1) used is that the polyol (A) and the polyisocyanate (B) have a suitable viscosity while maintaining an excellent initial strength, and a good softness of the cured film can be obtained.
  • the amount of the compound (a1) used is preferably in the range of 0.1 to 30% by mass, more preferably in the range of 0.2 to 25% by mass in the polyol (A) for the same reason. A range of 5 to 20% by mass is more preferable.
  • polyol (A) examples include polyester polyol, polyether polyol, polycarbonate polyol, acrylic polyol, dimer diol, isoprene polyol, polybutadiene polyol, and the like. These polyols may be used alone or in combination of two or more. Among these, it is preferable to use a polyether polyol from the viewpoint of obtaining even more excellent low viscosity and flexibility.
  • polyether polyol examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyoxyethylene polyoxypropylene glycol, polyoxyethylene polyoxytetramethylene glycol, and polyoxypropylene polyoxytetramethylene glycol. it can. These polyether polyols may be used alone or in combination of two or more. Among these, it is preferable to use polypropylene glycol from the viewpoint that even more excellent low viscosity, flexibility and initial strength can be obtained.
  • the number average molecular weight of the polyether polyol is preferably less than 2,800, more preferably in the range of 300 to 2,500, from the viewpoint of obtaining further excellent low viscosity, flexibility and initial strength.
  • the range of 600 to 2,200 is more preferable, and the range of 700 to 1,500 is particularly preferable.
  • the number average molecular weight of the said polyether polyol shows the value measured by the gel permeation chromatography (GPC) method.
  • the amount of the polyether polyol used is 75% by mass or more in the polyol (A) excluding the compound (a1) from the viewpoint of obtaining further excellent low viscosity, flexibility and initial strength.
  • 80 mass% or more is more preferable, and 90 mass% or more is still more preferable.
  • polyisocyanate (B) examples include aromatic polyisocyanates such as polymethylene polyphenyl polyisocyanate, diphenylmethane diisocyanate, carbodiimide-modified diphenylmethane diisocyanate, xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and naphthalene diisocyanate; hexamethylene diisocyanate , Cycloaliphatic diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, tetramethylxylylene diisocyanate, or other aliphatic or alicyclic polyisocyanates. These polyisocyanates may be used alone or in combination of two or more. Among these, aromatic polyisocyanate is preferably used from the viewpoint of reactivity and adhesive strength, and diphenylmethane diisocyanate is more preferably used.
  • the urethane prepolymer is obtained by reacting the polyol (A) and the polyisocyanate (B), and reacts with moisture present in the air or in the base material to which the urethane prepolymer is applied. It has an isocyanate group capable of forming a crosslinked structure.
  • a mixture of the polyol (A) is dropped into a reaction vessel containing the polyisocyanate (B) and then heated, and the isocyanate group of the polyisocyanate (B) is changed. , And can be produced by reacting under an excess condition with respect to the hydroxyl group of the polyol (A).
  • the equivalent ratio of the isocyanate group of the polyisocyanate (B) to the hydroxyl group of the polyol (A) further improves the adhesive strength and flexibility. From the point of view, the range of 1.1 to 5 is preferable, the range of 1.2 to 3 is more preferable, and the range of 1.15 to 1.45 is more preferable.
  • the isocyanate group content (hereinafter abbreviated as “NCO%”) of the urethane prepolymer is preferably in the range of 1 to 10% by mass from the viewpoint of further improving the adhesive strength.
  • the range of ⁇ 8 mass% is more preferred, the range of 1 ⁇ 5 mass% is further preferred, and the range of 1.2 ⁇ 4.5 mass% is particularly preferred.
  • the NCO% of the urethane prepolymer is a value measured by potentiometric titration in accordance with JISK1603-1: 2007.
  • the urethane bond content in the urethane prepolymer is preferably in the range of 0.2 to 3.5 mol / kg from the viewpoint of obtaining even better initial strength and initial creep properties.
  • the range of 0.6 to 3.2 mol / kg is more preferable, and the range of 1.1 to 2.9 mol / kg is particularly preferable.
  • content of the urethane bond of the said urethane prepolymer shows the value calculated from the preparation amount of the said polyol (A) and polyisocyanate (B).
  • the moisture-curable polyurethane hot melt resin composition contains the urethane prepolymer, but may contain other additives as necessary.
  • additives examples include a curing catalyst, an antioxidant, a tackifier, a plasticizer, a stabilizer, a filler, a dye, a pigment, a fluorescent brightening agent, a silane coupling agent, a wax, and a thermoplastic resin. Can be used. These additives may be used alone or in combination of two or more.
  • Examples of a method for obtaining a cured product from the moisture curable polyurethane hot melt resin composition of the present invention include a method in which the moisture curable polyurethane hot melt resin composition is applied to a substrate and moisture cured.
  • the substrate examples include resin substrates such as polyethylene terephthalate and polycarbonate, rubber substrates, fiber substrates, glass substrates, and wood.
  • Examples of a method for applying the moisture curable polyurethane hot melt resin composition to the substrate include a coater system such as a roll coater, a spray coater, a T-die coater, a knife coater, and a comma coater; Precise methods such as printing and offset printing; nozzle coating and the like.
  • the moisture-curable polyurethane hot melt resin composition it is preferable to heat and melt the moisture-curable polyurethane hot melt resin composition at 100 to 140 ° C. before applying the moisture-curable polyurethane hot melt resin composition to the substrate.
  • the thickness of the cured product layer of the moisture curable polyurethane hot melt resin composition can be appropriately determined according to the intended use, and is, for example, in the range of 0.001 to 0.5 cm.
  • the moisture curable polyurethane hot melt resin composition of the present invention has a storage elastic modulus (G ′) of melt viscoelasticity at 20 ° C. before curing of 0.
  • the pressure is preferably 1 MPa or more, preferably in the range of 0.2 to 1,000 MPa, and more preferably in the range of 0.3 to 500 MPa.
  • the storage elastic modulus (G ′) was measured by melting a moisture-curable polyurethane hot melt resin composition at 110 ° C. for 1 hour, sampling 10 ml, and measuring a melt viscoelasticity measuring device (“MCR-302 manufactured by Anton Paar).
  • MCR-302 manufactured by Anton Paar.
  • the storage elastic modulus (G ′) at 20 ° C. when the melt viscoelasticity measurement is performed from 110 ° C. to 10 ° C. at a temperature drop rate of 1 ° C./min and a frequency of 1 Hz is shown.
  • the Young's modulus of the cured film of the moisture-curable polyurethane hot melt resin composition of the present invention is preferably 20 MPa or less from the viewpoint of obtaining even more excellent flexibility, and is in the range of 0.5 to 15 MPa. Is more preferable, and the range of 1 to 10 MPa is still more preferable.
  • the Young's modulus is such that after the moisture-curable polyurethane hot melt resin composition is melted at 110 ° C. for 1 hour, the film thickness after curing is 100 ⁇ m on the polyethylene terephthalate substrate that has been subjected to a release treatment. Apply using a knife coater and leave it for 3 days to obtain a cured film, peel the cured film from the release PET, and stamp it with a No. 2 dumbbell, and use this specimen as Tensilon.
  • the moisture curable polyurethane hot melt resin composition of the present invention is excellent in initial strength. Furthermore, when a specific polyol is used as the polyol (A), a moisture-curable polyurethane hot melt resin composition having excellent low viscosity and flexibility can be obtained.
  • Example 1 In a four-necked flask equipped with a stirrer, thermometer, inert gas inlet, and reflux condenser, polypropylene glycol (number average molecular weight: 1,000, hereinafter abbreviated as “PPG”) 50 parts by mass, amorphous 20 parts by mass of polyester polyol (reaction product of neopentyl glycol and orthophthalic acid, number average molecular weight: 1,000, hereinafter abbreviated as “amorphous PEs”), 2-butyl-2-ethyl-1,3- 2 parts by mass of propanediol (hereinafter abbreviated as “BEP”) was charged and dehydrated by heating at 90 ° C.
  • PPG polypropylene glycol
  • amorphous 20 parts by mass of polyester polyol reaction product of neopentyl glycol and orthophthalic acid, number average molecular weight: 1,000, hereinafter abbreviated as “amorphous PEs”
  • BEP propanedi
  • MDI-1 4,4′-diphenylmethane diisocyanate
  • Example 2 The amount of PPG used is changed from 50 parts by mass to 44.5 parts by mass, the amount of amorphous PEs used is changed from 20 parts by mass to 15 parts by mass, the amount of BEP used is changed from 2 parts by mass to 7 parts by mass, A moisture-curable polyurethane hot melt resin composition was obtained in the same manner as in Example 1 except that the amount of MDI-1 used was changed from 28 parts by mass to 33.5 parts by mass. In addition, content of the urethane bond of the obtained urethane prepolymer was 2.06 mol / kg.
  • Example 3 The amount of PPG used is changed from 50 parts by weight to 49 parts by weight, the amount of amorphous PEs used is changed from 20 parts by weight to 19.5 parts by weight, BEP is changed to neopentyl glycol, and the amount of MDI-1 used is changed.
  • a moisture-curable polyurethane hot melt resin composition was obtained in the same manner as in Example 1 except that the amount was changed from 28 parts by mass to 29.5 parts by mass. In addition, content of the urethane bond of the obtained urethane prepolymer was 1.75 mol / kg.
  • Example 4 The amount of PPG used was changed from 50 to 49 parts by mass, the amount of amorphous PEs was changed from 20 to 19 parts by mass, BEP was changed to 2-methyl-1,3-propanediol, and MDI- 1 was replaced with an equivalent mixture of 2,4′-diphenylmethane diisocyanate and 4,4′-diphenylmethane diisocyanate (hereinafter abbreviated as “MDI-2”), and the amount used was changed from 28 parts by weight to 30 parts by weight. Except for the above, a moisture-curable polyurethane hot melt resin composition was obtained in the same manner as in Example 1. In addition, content of the urethane bond of the obtained urethane prepolymer was 1.80 mol / kg.
  • Example 1 The amount of PPG used is changed from 50 to 53 parts by mass, the amount of amorphous PEs used is changed from 20 to 21 parts by mass, the amount of BEP used is changed from 2 to 0 parts by mass, MDI- A moisture-curable polyurethane hot melt resin composition was obtained in the same manner as in Example 1 except that the amount of 1 used was changed from 28 parts by mass to 26 parts by mass. In addition, content of the urethane bond of the obtained urethane prepolymer was 1.48 mol / kg.
  • the number average molecular weight of the polyol used by the Example and the comparative example shows the value measured on condition of the following by gel permeation chromatography (GPC) method.
  • Measuring device High-speed GPC device (“HLC-8220GPC” manufactured by Tosoh Corporation) Column: The following columns manufactured by Tosoh Corporation were connected in series. "TSKgel G5000" (7.8 mm ID x 30 cm) x 1 "TSKgel G4000” (7.8 mm ID x 30 cm) x 1 "TSKgel G3000” (7.8 mm ID x 30 cm) x 1 “TSKgel G2000” (7.8 mm ID ⁇ 30 cm) ⁇ 1 detector: RI (differential refractometer) Column temperature: 40 ° C Eluent: Tetrahydrofuran (THF) Flow rate: 1.0 mL / min Injection amount: 100 ⁇ L (tetrahydrofuran solution with a sample concentration of 0.4 mass%) Standard sample: A calibration curve was prepared using the following standard polystyrene.
  • the moisture curable polyurethane hot melt resin composition of the present invention was found to be excellent in initial strength.
  • Comparative Example 1 is an embodiment in which the compound (a1) is not used, but the initial strength was insufficient.
  • Comparative Example 2 is an embodiment in which 1,6-hexanediol having no branched structure was used in place of the compound (a1), but the initial strength was insufficient.
  • Example 5 PPG 93 parts by mass in a four-necked flask equipped with a stirrer, thermometer, inert gas inlet and reflux condenser, and heated at 90 ° C. under reduced pressure until the water content becomes 0.05% by mass or less Dehydrated. Next, 7 parts by mass of 1,3-butanediol was charged. After the vessel internal temperature is cooled to 60 ° C., 54 parts by mass of MDI-1 is added, the temperature is raised to 110 ° C., and the reaction is allowed to proceed for about 3 hours until the isocyanate group content becomes constant. Got.
  • the urethane prepolymer had an NCO% of 2.2% by mass, an amount of urethane bonds of 2.22 mol / kg, and [NCO / OH] at the time of synthesis of 1.27.
  • Example 6 A urethane prepolymer was obtained in the same manner as in Example 5 except that the types and amounts used of the polyol and polyisocyanate used were changed as shown in Table 2.

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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)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention fournit une composition de résine thermofusible de polyuréthane durcissable à l'humidité qui est caractéristique en ce qu'elle présente une masse moléculaire moyenne en nombre inférieure à 500, possède une structure ramifiée, et comprend un prépolymère d'uréthane possédant un groupe isocyanate consistant en un produit de réaction d'un polyol (A) contenant un composé (a1) ayant deux à quatre groupes hydroxyle dans chaque molécule, et d'un polyisocyanate (B). En outre, l'invention fournit un objet durci caractéristique en ce qu'il est formé à partir de ladite composition de résine thermofusible de polyuréthane durcissable à l'humidité. De préférence, la teneur en liaison uréthane dudit prépolymère d'uréthane, est comprise dans une plage de ０,２ à ３,５ｍｏｌ／ｋｇ. Enfin, de préférence, ledit polyol (A) contient également un polyol de polyéther.
PCT/JP2019/005248 2018-02-22 2019-02-14 Composition de résine thermofusible de polyuréthane durcissable à l'humidité, et objet durci associé WO2019163621A1 (fr)

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JP2018208159 2018-11-05
JP2018-208159 2018-11-05

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020128515A (ja) * 2019-02-12 2020-08-27 日立化成株式会社 湿気硬化型ホットメルト接着剤及び接着体
WO2023157384A1 (fr) * 2022-02-17 2023-08-24 Dic株式会社 Composition de résine thermofusible de polyuréthane durcissable à l'humidité, adhésif sensible à la pression, stratifié et procédé de production de stratifié

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JP2003277459A (ja) * 2002-03-27 2003-10-02 Achilles Corp ポリウレタンウレア発泡体シートおよび該シートを用いた合成皮革
JP2003313531A (ja) * 2002-04-22 2003-11-06 Asahi Glass Co Ltd 湿気硬化型接着剤
JP2010090263A (ja) * 2008-10-08 2010-04-22 Toyo Polymer Co Ltd 無溶剤形一液湿気硬化型ポリウレタン系接着剤
JP2014083800A (ja) * 2012-10-25 2014-05-12 Dic Corp 積層体及び画像表示装置
WO2015033734A1 (fr) * 2013-09-04 2015-03-12 Dic株式会社 Composition de mousse d'uréthane et coussin d'amortissement
JP2015078326A (ja) * 2013-10-18 2015-04-23 Dic株式会社 ウレタン樹脂、それを用いたコーティング剤及び物品

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JPS55151075A (en) * 1979-05-09 1980-11-25 Nat Starch Chem Corp Modified polyurethane adhesive composition
JPH1192544A (ja) * 1997-09-19 1999-04-06 Dainippon Ink & Chem Inc 一液湿気硬化型ウレタン樹脂組成物
JP2000297130A (ja) * 1999-04-15 2000-10-24 Mitsubishi Gas Chem Co Inc ポリイソシアネートプレポリマー
JP2001059008A (ja) * 1999-06-14 2001-03-06 Mitsubishi Gas Chem Co Inc 舗装用バインダー及び舗装材
JP2001098047A (ja) * 1999-07-27 2001-04-10 Takeda Chem Ind Ltd ガスバリア性ポリウレタン樹脂及びこれを含むガスバリア性フィルム
JP2003277459A (ja) * 2002-03-27 2003-10-02 Achilles Corp ポリウレタンウレア発泡体シートおよび該シートを用いた合成皮革
JP2003313531A (ja) * 2002-04-22 2003-11-06 Asahi Glass Co Ltd 湿気硬化型接着剤
JP2010090263A (ja) * 2008-10-08 2010-04-22 Toyo Polymer Co Ltd 無溶剤形一液湿気硬化型ポリウレタン系接着剤
JP2014083800A (ja) * 2012-10-25 2014-05-12 Dic Corp 積層体及び画像表示装置
WO2015033734A1 (fr) * 2013-09-04 2015-03-12 Dic株式会社 Composition de mousse d'uréthane et coussin d'amortissement
JP2015078326A (ja) * 2013-10-18 2015-04-23 Dic株式会社 ウレタン樹脂、それを用いたコーティング剤及び物品

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020128515A (ja) * 2019-02-12 2020-08-27 日立化成株式会社 湿気硬化型ホットメルト接着剤及び接着体
JP7275622B2 (ja) 2019-02-12 2023-05-18 株式会社レゾナック 湿気硬化型ホットメルト接着剤及び接着体
WO2023157384A1 (fr) * 2022-02-17 2023-08-24 Dic株式会社 Composition de résine thermofusible de polyuréthane durcissable à l'humidité, adhésif sensible à la pression, stratifié et procédé de production de stratifié

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