JP6132139B2 - Moisture-curing polyurethane hot melt resin composition and cosmetic product - Google Patents

Description

  An object of the present invention is to provide a moisture-curable polyurethane hot melt resin composition excellent in surface smoothness and initial creep property and a fabricated member.

  Conventionally, in the building materials field, to improve aesthetics and impart durability, wood, laminated timber, plywood, MDF (medium density fiberboard), particle board, etc. are used as the base material. Cosmetic makeup members obtained by bonding decorative sheets having colors and patterns are widely used.

  When the sheet or the like is a so-called specular decorative sheet having a glossy surface, it is very excellent not to impair its specularity in a decorative material such as a decorative plate obtained by bonding the sheet and the base material. Surface smoothness is required.

  Examples of moisture curable polyurethane hot melt adhesives that can be used in the production of the decorative member include polyether polyols, aliphatic polyester polyols, and ethylene glycol, neopentyl glycol, isophthalic acid, and terephthalic acid. A moisture-curable polyurethane hot melt adhesive containing a urethane prepolymer obtained by reacting a polyol containing an aromatic polyester polyol and 4,4′-diphenylmethane diisocyanate is disclosed (see, for example, Patent Document 1). .)

  However, when the moisture-curable polyurethane hot melt adhesive is used, although it can have excellent initial creep properties (initial adhesiveness), the surface smoothness is continuously improved as the curing of the adhesive proceeds. As a result, there was a problem that unevenness or the like occurred in the mirror surface portion of the resulting decorative member, and the mirror surface property was impaired.

JP 2006-45841 A

  The problem to be solved by the present invention is to provide a moisture curable polyurethane hot melt resin composition having excellent surface smoothness and initial creep properties.

  The inventors of the present invention, while pursuing research to solve the above-mentioned problems, paid attention to the polyol used for the urethane prepolymer, and advanced the earnest research to complete the present invention.

  That is, the present invention relates to an aromatic polyester polyol (A-1) obtained by reacting 1,6-hexanediol, terephthalic acid and / or isophthalic acid, and an aliphatic dicarboxylic acid, an aliphatic crystalline polyester polyol (A -2), a urethane prepolymer having an isocyanate group obtained by reacting a polyol (A) containing a polyether polyol (A-3) and an acrylic polyol (A-4) with a polyisocyanate (B) The present invention provides a moisture-curable polyurethane hot-melt adhesive characterized in that, and a manufactured member obtained using the same.

The moisture-curable polyurethane hot melt adhesive of the present invention is excellent in surface smoothness and initial creep property.
Therefore, the moisture-curable polyurethane hot melt adhesive of the present invention can be particularly suitably used for the production of a cosmetic product such as a decorative mirror surface sheet.

  The moisture-curable polyurethane hot melt adhesive of the present invention is an aromatic polyester polyol (A-1) obtained by reacting 1,6-hexanediol, terephthalic acid and / or isophthalic acid, and an aliphatic dicarboxylic acid (hereinafter referred to as “polyester”). , "Abbreviated as" aromatic polyester polyol (A-1) "), aliphatic crystalline polyester polyol (A-2), polyether polyol (A-3) and polyol containing acrylic polyol (A-4) It contains a urethane prepolymer having an isocyanate group obtained by reacting (A) with polyisocyanate (B).

  The aromatic polyester polyol (A-1) is obtained by a conventionally known method using 1,6-hexanediol, terephthalic acid and / or isophthalic acid, and aliphatic dicarboxylic acid.

  Examples of the aliphatic dicarboxylic acid include adipic acid, glutaric acid, pimelic acid, suberic acid, dimer acid, sebacic acid, undecanedicarboxylic acid, oxalic acid, malonic acid, succinic acid, azelaic acid, 1,12-dodecanediic acid. An acid or the like can be used. These may be used alone or in combination of two or more. Among these, from the viewpoint of further improving the initial creep property and the surface smoothness, it is preferable to use an aliphatic dicarboxylic acid having 4 to 12 carbon atoms, and the carbon atom number is 6 to 10. More preferably, sebacic acid is used.

  As the dibasic acid used in addition to the aliphatic dicarboxylic acid, it is more preferable to use terephthalic acid from the viewpoint of further improving initial creep and surface smoothness.

  The molar ratio between the terephthalic acid and / or isophthalic acid and the aliphatic dicarboxylic acid is in the range of 40/60 to 90/10 from the viewpoint of further improving the initial creep property and surface smoothness. Preferably, it is in the range of 50/50 to 80/20.

  The number average molecular weight of the aromatic polyester polyol (A-1) is preferably in the range of 500 to 5,000, preferably 1,000 to 3 from the viewpoint of further improving the initial creep property and surface smoothness. The range of 1,000 is more preferred. In addition, the number average molecular weight of the said aromatic polyester polyol (A-1) 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 μL (tetrahydrofuran solution with a sample concentration of 0.4 mass%)
Standard sample: A calibration curve was prepared using the following standard polystyrene.

(Standard polystyrene)
"TSKgel standard polystyrene A-500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-1000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-2500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-5000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-1" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-2" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-4" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-10" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-20" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-40" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-80" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-128" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-288" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-550" manufactured by Tosoh Corporation

  The amount of the aromatic polyester polyol (A-1) used is preferably in the range of 3 to 35% by mass in the total amount of the polyol (A) from the viewpoint of further improving the initial creep property and surface smoothness. The range of 5-30 mass% is more preferable, and the range of 10-25 mass% is still more preferable.

  The aliphatic crystalline polyester polyol (A-2) is an essential component for imparting particularly excellent initial creep properties. For example, a reaction product of a compound having a hydroxyl group and a polybasic acid can be used. . In the present invention, “crystallinity” means that the peak of crystallization heat or heat of fusion can be confirmed in DSC (differential scanning calorimeter) measurement in accordance with JIS K 7121. Indicates that the peak cannot be confirmed.

  Examples of the compound having a hydroxyl group include ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, trimethylolpropane, trimethylolethane, and glycerin. Can do. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use butanediol, hexanediol, octanediol, and decanediol from the viewpoint of improving crystallinity and improving waterproofness and adhesiveness.

  Examples of the polybasic acid include oxalic acid, malonic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, 1,12-dodecanedicarboxylic acid, and the like.

  The number average molecular weight of the aliphatic crystalline polyester polyol (A-2) is preferably in the range of 500 to 10,000, more preferably in the range of 2,000 to 8,000, from the viewpoint of initial creep properties. In addition, the number average molecular weight of the said crystalline polyester polyol (A-2) shows the value obtained by measuring similarly to the number average molecular weight of the said aromatic polyester polyol (A-1).

  Moreover, as melting | fusing point of the said aliphatic crystalline polyester polyol (A-2), the range of 40-130 degreeC is preferable. In addition, melting | fusing point of the said crystalline polyester polyol (A-2) shows the value measured based on JISK7121-1987.

  As a usage-amount of the said aliphatic crystalline polyester polyol (A-2), it is the range of 10-200 mass parts with respect to 100 mass parts of said aromatic polyester polyol (A-1) from viewpoints, such as initial stage creep property. Are preferable, the range of 15-150 mass parts is more preferable, and the range of 20-100 mass parts is especially preferable.

  The polyether polyol (A-3) is an essential component for imparting excellent initial creep properties and surface smoothness, for example, polyethylene glycol, polypropylene glycol, prebutylene glycol, polytetramethylene glycol, and these A product obtained by adding an alkylene oxide to the above can be used.

  The number average molecular weight of the polyether polyol (A-3) is preferably in the range of 500 to 5,000, more preferably in the range of 700 to 4,000, from the viewpoint of initial creep properties and surface smoothness. In addition, the number average molecular weight of the said polyether polyol (A-3) shows the value obtained by measuring similarly to the number average molecular weight of the said aromatic polyester polyol (A-1).

  As a usage-amount of the said polyether polyol (A-3), the range of 20-400 mass parts with respect to 100 mass parts of said aromatic polyester polyol (A-1) from a viewpoint of initial stage creep property or surface smoothness. It is preferable that the range of 40-300 mass parts is more preferable.

  The acrylic polyol (A-4) is an essential component for imparting excellent workability by adjusting initial creep properties, surface smoothness, and moderate open time after application (bondable time). It is obtained by polymerizing a (meth) acrylic compound containing a (meth) acrylic compound having In the present invention, “(meth) acrylic compound” refers to one or both of a methacrylic compound and an acrylic compound, “(meth) acrylate” refers to one or both of methacrylate and acrylate, and “(meta) “Acrylic acid” refers to one or both of methacrylic acid and acrylic acid.

  As the (meth) acrylic compound having a hydroxyl group, it is preferable to use a (meth) acrylic acid alkyl ester having a hydroxyl group because of easy availability of raw materials. For example, 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) Acrylate, hydroxybutyl (meth) acrylate, pentaerythritol triacrylate and the like can be used. Among these, it is particularly preferable to use 2-hydroxyethyl (meth) acrylate from the viewpoint of further improving the initial creep property and the surface smoothness.

  Examples of the (meth) acrylic compound that can be used other than the (meth) acrylic compound having a hydroxyl group include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, and n-butyl (meth) acrylate. , Isobutyl (meth) acrylate, tert-butyl (meth) acrylate, neopentyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, Cetyl (meth) acrylate, lauryl (meth) acrylate, isobornyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H 5H-octafluoropentyl (meth) acrylate, 2- (perfluorooctyl) ethyl (meth) acrylate, cyclohexyl (meth) acrylate, sidiclopentanyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, polyethylene glycol Mono (meth) acrylate, methoxyethyl (meth) acrylate, methoxybutyl (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, benzyl (meth) acrylate, 2-ethyl-2-methyl -[1,3] -Dioxolan-4-yl-methyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobornyl (meth) acrylate, etc. may be used. Kill. These (meth) acrylic compounds may be used alone or in combination of two or more. Among these, it is preferable to use methyl (meth) acrylate and n-butyl (meth) acrylate from the viewpoint of further improving initial creep properties and surface smoothness.

  The weight average molecular weight of the acrylic polyol (A-4) is preferably from 5,000 to 50,000, more preferably from 10,000 to 40,000, from the viewpoint of further improving initial creep properties and surface smoothness. The range of 15,000 to 30,000 is more preferable. In addition, the weight average molecular weight of the said acrylic polyol (A-4) is the same as the measuring method of the number average molecular weight of the said aromatic polyester polyol (A-1).

  The glass transition temperature of the acrylic polyol (A-4) is preferably in the range of 30 to 120 ° C, and more preferably in the range of 50 to 80 ° C, from the viewpoint of further improving the initial creep properties and surface smoothness. In addition, the glass transition temperature of the said acrylic polyol (A-4) shows the midpoint glass transition temperature (Tmg) measured based on JISK7121-1987.

  As a usage-amount of the said acrylic polyol (A-4), it is 20-400 mass with respect to 100 mass parts of said aromatic polyester polyol (A-1) from a viewpoint which can improve initial stage creep property and surface smoothness further. The range of parts is preferable, the range of 50 to 300 parts by mass is more preferable, and the range of 70 to 200 parts by mass is particularly preferable.

  The polyol (A) comprises the aromatic polyester polyol (A-1), the aliphatic crystalline polyester polyol (A-2), the polyether polyol (A-3), and the acrylic polyol (A-4). Although it contains as an essential component, you may contain another polyol as needed.

  As said other polyol, aromatic polyester polyols other than the said aromatic polyester polyol (A-1), aliphatic amorphous polyester polyol, polycarbonate polyol etc. can be used, for example. By using these polyols, there is an effect of improving the adhesion to an untreated PET sheet or the like.

  Examples of the polyisocyanate (B) include polymethylene polyphenyl polyisocyanate, diphenylmethane diisocyanate, carbodiimide-modified diphenylmethane diisocyanate isocyanate, phenylene diisocyanate, tolylene diisocyanate, naphthalene diisocyanate, and other aromatic polyisocyanates, hexamethylene diisocyanate, lysine diisocyanate, Aliphatic or alicyclic polyisocyanates such as cyclohexane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, xylylene diisocyanate, and tetramethylxylylene diisocyanate can be used. These polyisocyanates may be used alone or in combination of two or more. Among these, it is preferable to use diphenylmethane diisocyanate from the viewpoint of reactivity and adhesiveness.

  The amount of the polyisocyanate (B) used is preferably in the range of 10 to 50 parts by weight, and 10 to 30 parts by weight with respect to 100 parts by weight of the moisture-curable polyurethane hot melt adhesive of the present invention, from the viewpoint of viscosity and the like. A range of parts is more preferred.

  The urethane prepolymer having an isocyanate group is obtained by reacting the polyol (A) and the polyisocyanate (B), and is in the air or in a casing or adherend to which the urethane prepolymer is applied. It has an isocyanate group that can react with moisture present in the polymer to form a crosslinked structure at the polymer terminal or in the molecule.

  As a method for producing the urethane prepolymer, for example, 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).

  When the urethane prepolymer is produced, the equivalent ratio of the isocyanate group of the polyisocyanate (B) to the hydroxyl group of the polyol (A) ([isocyanate group / hydroxyl group]) is the surface smoothness and initial creep property. From the viewpoint of further improving the ratio, a range of 1.1 to 5.0 is preferable, and a range of 1.5 to 3.0 is more preferable.

  The urethane prepolymer can be usually produced without a solvent, but may be produced by reacting the polyol (A) and the polyisocyanate (B) in an organic solvent. When reacting in an organic solvent, an organic solvent such as ethyl acetate, n-butyl acetate, methyl ethyl ketone, and toluene that does not hinder the reaction can be used, but by a method such as heating under reduced pressure during or after the reaction. It is necessary to remove the organic solvent.

  When manufacturing the said urethane prepolymer, a urethanation catalyst can be used as needed. The urethanization catalyst can be appropriately added at any stage of the reaction.

  Examples of the urethanization catalyst include nitrogen-containing compounds such as triethylamine, triethylenediamine and N-methylmorpholine; metal salts such as potassium acetate, zinc stearate and tin octylate; and organometallic compounds such as dibutyltin dilaurate. Can do.

  The isocyanate group content (hereinafter referred to as NCO%) of the urethane prepolymer obtained by the above method is in the range of 1.5 to 8.0% from the viewpoint of further improving the surface smoothness and initial creep properties. Preferably, the range of 1.7 to 5.0% is more preferable, and the range of 1.8 to 3.0% is particularly preferable. In addition, NCO% of the said urethane prepolymer shows the value measured by the potentiometric titration method based on JISK1603-1.

  As the viscosity of the urethane prepolymer, the melt viscosity at 120 ° C. is preferably in the range of 1,000 to 50,000 mPa · s from the viewpoint of further improving the surface smoothness and initial creep property, and 2,000 More preferably, it is in the range of ˜20,000 mPa · s. The melt viscosity at 120 ° C. is a value measured with a cone plate viscometer (manufactured by ICI).

  The softening point of the urethane prepolymer is preferably in the range of 30 to 120 ° C. from the viewpoint of further improving the surface smoothness and initial creep property. The softening point refers to the temperature at which the fluid starts to flow and loses cohesion when the temperature of the ureta prepolymer is raised stepwise. Further, the softening point of the urethane prepolymer indicates a value obtained by a ring and ball method in accordance with JIS K 5902.

  The moisture-curable polyurethane hot melt adhesive of the present invention may be composed of the urethane prepolymer (only, but may contain other additives as necessary.

  Examples of the other additives include antioxidants, tackifiers, plasticizers, stabilizers, fillers, dyes, pigments, fluorescent brighteners, silane coupling agents, waxes, thermoplastic resins, and the like. be able to.

  As described above, since the moisture-curable polyurethane hot melt adhesive of the present invention is excellent in surface smoothness and initial creep property, it can be particularly suitably used for the production of a cosmetic product such as a cosmetic mirror sheet.

  The decorative product of the present invention can be produced by laminating a substrate and a sheet or film as described below using the moisture-curable polyurethane hot melt adhesive.

  As the base material, for example, a wood base material such as plywood, MDF (medium density fiber board), particle board, or a metal base material such as aluminum or iron can be used. Further, the base material may have a complicated shape such as a groove, an R portion, and an inverted R portion.

  As the sheet or film, for example, a sheet or film obtained using a resin such as polyester, polyamide, polystyrene, polycarbonate, vinyl chloride, ethylene-vinyl acetate copolymer, polyvinyl alcohol, polyethylene, polypropylene, paper, Metal foil, a veneer, etc. can be used.

  The sheet or film is generally referred to as decorative paper, base paper for decorative board, decorative sheet, and the like, and the surface thereof is provided with a decorative solid color or various colors or patterns. . In addition, the back surface thereof may be subjected to primer treatment with a resin or the like. Among them, the moisture-curable polyurethane hot melt adhesive can form an adhesive layer having excellent surface smoothness, so even when a decorative sheet having a mirror-like surface is used, the mirror surface derived from the decorative sheet is used. It does not deteriorate the sex. In addition, since the adhesive layer can form a high-hardness adhesive layer, an external impact is applied to the decorative board obtained by bonding the equipment and the decorative sheet using the adhesive. Even when is added, it is possible to suppress the deterioration of the surface appearance and specularity.

  As a method for bonding the substrate and the sheet or the like using the moisture curable polyurethane hot melt adhesive of the present invention, for example, the moisture curable polyurethane hot melt adhesive is heated in a range of 60 to 150 ° C. It is melted and applied onto a substrate using a roll coater, spray coater, T-die coater, knife coater, etc., and the sheet or the like is bonded to the coated surface, or the roll coater or the like is used. It is possible to use a method of applying on a sheet or the like, bonding the substrate to the application surface, and appropriately pressing according to the shape of the substrate by a roll press, flat press, belt press or the like. .

  Hereinafter, the present invention will be described in detail with reference to examples.

[Example 1]
In a four-necked flask equipped with a thermometer, stirrer, inert gas inlet and reflux condenser, the aromatic polyester polyol (A-1-1) (1,6-hexanediol, terephthalic acid and sebacic acid in a molar ratio , 53/33/14, number average molecular weight 2,000) 20 parts by mass, aliphatic crystalline polyester polyol (A-2-1) (1,6-hexanediol and 1,12-dodecane) Dicarboxylic acid reacted, number average molecular weight 3,500) 12 parts by mass, polypropylene glycol (A-3-1) (number average molecular weight 1,000) 30 parts by mass, acrylic polyol (A-4-1) ) (Methacrylic acid, butyl methacrylate and 2-hydroxyethyl methacrylate reacted at a molar ratio of 73.8 / 25.8 / 0.4, number average molecular weight 20, 00, Tg; 73 ℃) was placed 20 parts by weight, mixed by heating under reduced pressure at 100 ° C., and dehydrated until the water in the flask is 0.05 mass% or less.
Next, the inside of the flask is cooled to 90 ° C., 18 parts by mass of 4,4′-diphenylmethane diisocyanate melted at 70 ° C. is added, and the mixture is reacted at 110 ° C. for about 3 hours until the isocyanate group content becomes constant in a nitrogen atmosphere. As a result, a urethane prepolymer (melt viscosity at 120 ° C .; 7,000 mPa · s, NCO%; 2.2%) was obtained, and a moisture-curable polyurethane hot melt adhesive was obtained.

[Examples 2 to 4 and Comparative Examples 1 to 4]
A moisture-curable polyurethane hot melt adhesive was obtained in the same manner as in Example 1 except that the types and amounts of the polyol (A) and polyisocyanate (B) used were changed as shown in Tables 1-2.

[Evaluation method of initial creep property]
The moisture-curable polyurethane hot melt adhesives obtained in Examples and Comparative Examples were melted at a temperature of 110 ° C. for 1 hour using a melting apparatus. The adhesive was applied onto a 75 μm thick PET sheet (“Lumirror” manufactured by Toray Industries, Inc.) using a T-die coater so as to have a thickness of about 50 μm. On the coating layer, MDF was bonded and pressure-bonded with a pressure roller. A load of 75 g was applied in the 90 ° direction for 15 minutes after the lapse of 3 minutes after the pressure bonding, and the peel length (mm) was measured to obtain initial creep properties.

[Method for evaluating surface smoothness]
The moisture-curable polyurethane hot melt adhesives obtained in Examples and Comparative Examples were melted at a temperature of 110 ° C. for 1 hour using a melting apparatus. The adhesive was applied to the back surface of the mirror surface decorative sheet using a T-die coater so that the thickness was about 50 μm. On the coating layer, MDF was bonded and pressure-bonded using a rubber roller to obtain a decorative product.
The surface smoothness was evaluated as “◯” when there was no unevenness or the like by visual observation when a fluorescent lamp was applied from the mirror decorative sheet side of the decorative member, and “X” when there was even unevenness.

Abbreviations in Tables 1 and 2 will be described.
“Aromatic polyester polyol (A-1-2)”: 1,6-hexanediol, terephthalic acid and adipic acid reacted at a molar ratio of 53/33/14, number average molecular weight 2,000
"Other aromatic polyester polyol-1": ethylene glycol, adipic acid, isophthalic acid and terephthalic acid reacted at a molar ratio of 51/29/10/10, number average molecular weight 3,500
“Amorphous polyester polyol-1”; a reaction of neopentyl glycol and adipic acid, number average molecular weight 2,000
“MDI”; 4,4′-diphenylmethane diisocyanate

  It turned out that the thing of Examples 1-4 which is a moisture hardening type polyurethane hot-melt-adhesive agent of this invention is excellent in initial stage creep property and surface smoothness.

  On the other hand, although the comparative example 1 is an aspect which does not use an aromatic polyester polyol (A-1) as a polyol (A), surface smoothness was unsatisfactory.

  Although the comparative example 2 is an aspect which does not use an aliphatic crystalline polyester polyol (A-2) as a polyol (A), initial stage creep property was unsatisfactory.

  In Comparative Example 3, the polyether polyol (A-3) was not used as the polyol (A), but the surface smoothness was poor.

  Although the comparative example 4 is an aspect which does not use an acrylic polyol (A-4) as a polyol (A), surface smoothness and initial stage creep property were unsatisfactory.

Claims (5)

Aromatic polyester polyol (A-1) obtained by reacting 1,6-hexanediol, terephthalic acid and / or isophthalic acid, and aliphatic dicarboxylic acid, aliphatic crystalline polyester polyol (A-2), poly Isocyanate obtained by reacting polyisocyanate (B) with ether polyol (A-3) and polyol (A-4) containing acrylic polyol (A-4) having a glass transition temperature in the range of 30 to 120 ° C. A moisture-curable polyurethane hot-melt adhesive comprising a urethane prepolymer having a group. The moisture-curable polyurethane hot melt adhesive according to claim 1, wherein the aliphatic dicarboxylic acid used in the aromatic polyester polyol (A-1) is sebacic acid. The moisture-curable polyurethane hot melt adhesive according to claim 1, wherein the dibasic acid other than the aliphatic dicarboxylic acid used in the aromatic polyester polyol (A-1) is terephthalic acid. The moisture-curable polyurethane hot melt adhesive according to claim 1, wherein the acrylic polyol (A-4) has a weight average molecular weight in the range of 5,000 to 50,000. A cosmetic product obtained by using the moisture-curable polyurethane hot melt adhesive according to any one of claims 1 to 4 .