JP7172542B2 - Moisture-curable urethane hot-melt resin composition and laminate - Google Patents

Description

The present invention relates to a moisture-curable urethane hot-melt resin composition and a laminate.

Moisture-curable urethane hot-melt resin compositions based on urethane prepolymers are widely used for adhesion of metal materials, wood materials, plastics, rubber, textile products, synthetic leather, paper products, etc. It is used in various fields such as decorative panels, automotive interior materials, and clothing.

Moisture-curable urethane hot-melt resin compositions are characterized by the fact that they are solvent-free like other hot-melt adhesives, and in addition to obtaining initial adhesive strength by cooling and solidifying, they also last about 24 to 72 hours after adhesion. By reacting with the air or the humidity of the adherend within the time of , the final adhesive strength and heat resistance that cannot be obtained with other hot-melt adhesives can be obtained. However, as with other hot-melt adhesives, it is not easy to further increase the initial adhesive strength only by cooling and solidifying.

As the moisture-curable urethane hot-melt resin composition having excellent initial adhesive strength, for example, a moisture-curable polyurethane hot-melt adhesive containing a urethane prepolymer using a plurality of different types of polyester polyols is disclosed ( See, for example, Patent Literature 1).

Although the adhesive has excellent initial adhesive strength, it has been pointed out that the usable time (open time) is short and the productivity is poor.

JP 2015-52090 A

The problem to be solved by the present invention is to provide a moisture-curable urethane hot-melt resin composition excellent in initial adhesive strength and open time.

The present invention provides a polyol (A) containing an alicyclic polyol (a1), a polyisocyanate (B), and a compound (C) having one or more (meth)acryloyl groups and having one hydroxyl group. Essential raw materials are a urethane prepolymer (i) having an isocyanate group, and a moisture-curable polyurethane hot-melt resin composition characterized by containing a photopolymerization initiator (ii), and a cured product layer thereof to provide a laminate having

The moisture-curable urethane hot-melt resin composition of the present invention is excellent in initial adhesive strength and open time.

The moisture-curable urethane hot-melt resin composition of the present invention has a polyol (A) containing an alicyclic polyol (a1), a polyisocyanate (B), and one or more (meth)acryloyl groups, and It contains a urethane prepolymer (i) having an isocyanate group and a photopolymerization initiator (ii), which is essentially made of a compound (C) having one hydroxyl group.

The urethane prepolymer (i) has a polyol (A) containing an alicyclic polyol (a1), a polyisocyanate (B), one or more (meth)acryloyl groups, and one hydroxyl group. It is obtained by using the compound (C) as an essential raw material and has an isocyanate group.

The alicyclic polyol (a1) is an essential component for obtaining excellent open time. As the alicyclic polyol (a1), for example, alicyclic polyester polyol, alicyclic polycarbonate polyol, alicyclic polyacryl polyol, alicyclic polyether polyol, etc. can be used. These polyols may be used alone or in combination of two or more. Among these, alicyclic polyester polyols and/or alicyclic polycarbonate polyols are preferably used, and alicyclic polyester polyols are more preferred, from the viewpoint of obtaining even more excellent open time.

Examples of the alicyclic polyester polyol include a reaction product of an alicyclic compound having two or more hydroxyl groups and an aliphatic polybasic acid, and a reaction product of an aliphatic compound having two or more hydroxyl groups and an alicyclic polybasic acid. reaction products and the like. In addition, such a reactant can be obtained by a known esterification reaction.

Examples of the alicyclic compound having two or more hydroxyl groups include cyclopentanediol, cyclohexanediol, cyclohexanedimethanol, hydrogenated bisphenol A; alkylene oxide adducts thereof, and the like. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use cyclohexanedimethanol from the viewpoint of obtaining an even more excellent open time.

Examples of the aliphatic polybasic acid include succinic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedioic acid, dodecanedioic acid, eicosadioic acid, citraconic acid, itaconic acid, and citraconic anhydride. , itaconic anhydride and the like can be used. These compounds may be used alone or in combination of two or more.

Examples of the aliphatic compound having two or more hydroxyl groups include ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7- heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, diethylene glycol, triethylene glycol, triethylene glycol, tetraethylene glycol, neopentyl glycol, 1 ,3-butanediol, 2,2-diethyl-1,3-propanediol, 2,2-diethylpropanediol, 3-methyl-1,5-pentanediol, 2-ethyl-2-butyl-1,3- Compounds such as propanediol, 2-methyl-1,8-octanediol, 2,4-diethyl-1,5-pentanediol, 2-methylpropanediol, trimethylolethane, trimethylolpropane, and pentaerythritol can be used. can. These compounds may be used alone or in combination of two or more. Among these, 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, neopentyl glycol, and 2-methylpropanediol are preferred because they provide even better weather resistance and adhesive strength. , and 3-methyl-1,5-pentanediol. It is preferable to use one or more compounds selected from the group consisting of 3-methyl-1,5-pentanediol, and from the viewpoint of obtaining a more excellent open time than having a branched structure, neopentyl More preferably, one or more selected from the group consisting of glycol, 2-methylpropanediol, and 3-methyl-1,5-pentanediol.

As the alicyclic polybasic acid, for example, cyclohexanedicarboxylic acid, cyclopentanedicarboxylic acid, cyclohexanediadipate, and the like can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use cyclohexanedicarboxylic acid from the viewpoint of obtaining even more excellent open time.

As the alicyclic polycarbonate polyol, for example, one obtained by reacting a carbonate ester and/or phosgene with a polyol compound containing an alicyclic polyol having a molecular weight in the range of 50 to 400 can be used. In addition, the molecular weight of the said alicyclic polyol shows the value calculated from chemical structural formula.

As the carbonate ester, for example, methyl carbonate, dimethyl carbonate, ethyl carbonate, diethyl carbonate, cyclocarbonate, diphenyl carbonate and the like can be used. These compounds may be used alone or in combination of two or more.

Examples of the alicyclic polyol include 1,2-cyclobutanediol, 1,3-cyclopentanediol, 1,4-cyclohexanediol, cycloheptanediol, cyclooctanediol, 1,4-cyclohexanedimethanol, and hydroxypropyl. cyclohexanol, tricyclo[5.2.1.0 ^2,6 ]decane-dimethanol, bicyclo[4.3.0]-nonanediol, dicyclohexanediol, tricyclo[5.3.1.1]dodecanediol, bicyclo[4.3.0]nonanedimethanol, tricyclo[5,3,1,1]dodecane-diethanol, hydroxypropyltricyclo[5.3.1.1]dodecanol, spiro[3.4]octanediol, Butylcyclohexanediol, 1,1'-bicyclohexylidenediol, cyclohexanetriol, hydrogenated bisphenol A, 1,3-adamantanediol and the like can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use 1,4-cyclohexanedimethanol from the viewpoint of obtaining even better open time.

The amount of the alicyclic polyol to be used is preferably 20% by mass or more, more preferably 30% by mass or more, in the polyol compound in order to obtain even more excellent low viscosity and open time.

Examples of polyol compounds that can be used in addition to the alicyclic polyols include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, 1,3-propanediol, dipropylene glycol, and triethylene glycol. Propylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,5-hexanediol, 1,6-hexane Diol, 2,5-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol , 2-methyl-1,3-propanediol, neopentyl glycol, 2-butyl-2-ethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2-ethyl-1,3- Hexanediol, 2-methyl-1,8-octanediol, glycerin, trimethylolpropane, ditrimethylolpropane, tritrimethylolpropane, pentaerythritol and the like can be used. Among these, it is preferable to use 1,6-hexanediol from the viewpoint of obtaining even better open time.

The number average molecular weight of the alicyclic polyol (a1) is preferably in the range of 450 to 10,000, 500 to 5,000, from the viewpoint of obtaining even better low viscosity and open time. A range of 000 is more preferred, and a range of 600 to 3,000 is even more preferred. The number average molecular weight of the alicyclic polyol (a1) is a value measured under the following conditions by a gel permeation chromatography (GPC) method.

In addition to the alicyclic polyol (a1), the polyol (A) can be used in combination with other polyols, if necessary.

Examples of other polyols that can be used include polyester polyols, polycaprolactone polyols, polyether polyols, polycarbonate polyols, acrylic polyols, and polyurethane polyols that do not have the alicyclic structure. These polyols may be used alone or in combination of two or more.

The amount of the alicyclic polyol (a1) used in the polyol (A) is preferably 10% by mass or more, and preferably 55% by mass or more, from the viewpoint of obtaining even more excellent open time. is more preferred.

In addition, the amount of the alicyclic polyol (a1) used is 100 in total of the polyol (A), the polyisocyanate (B) and the compound (C), from the viewpoint of obtaining even more excellent open time. It is preferably in the range of 10 to 80 parts by mass, more preferably in the range of 35 to 75 parts by mass, and even more preferably in the range of 40 to 70 parts by mass.

Examples of the polyisocyanate (B) include, for example, hexamethylene diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, tetramethylxylylene diisocyanate, and other aliphatic polyisocyanates or alicyclic polyisocyanates; Aromatic polyisocyanates such as diphenylmethane diisocyanate, carbodiimide-modified diphenylmethane diisocyanate, xylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate and naphthalene diisocyanate; isocyanurates thereof and the like can be used. These polyisocyanates may be used alone or in combination of two or more. Among these, it is selected from the group consisting of diphenylmethane diisocyanate, xylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, and isocyanurate derivatives thereof, from the viewpoint of obtaining even better reactivity and final adhesive strength. It is preferred to use one or more compounds.

As the amount of the polyisocyanate (B) used, the polyol (A), the polyisocyanate (B) and the compound (C ) and 100 parts by mass in total, it is preferably in the range of 1 to 50 parts by mass, more preferably in the range of 10 to 40 parts by mass.

The compound (C) is an essential component for obtaining excellent initial adhesive strength. By using the compound (C), a (meth)acryloyl group can be introduced into a part of the terminals of the urethane prepolymer, so that a good initial adhesive strength can be obtained by irradiating ultraviolet rays or the like. Examples of the compound (C) include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (Meth)acrylate, 6-hydroxyhexyl (meth)acrylate, hydroxyethylacrylamide and the like can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use 2-hydroxyethyl (meth)acrylate because (meth)acryloyl groups can be easily introduced and excellent initial adhesive strength can be obtained.

The amount of the compound (C) used is based on a total of 100 parts by mass of the polyol (A), the polyisocyanate (B) and the compound (C), from the viewpoint of obtaining even more excellent initial adhesive strength. , preferably in the range of 0.01 to 10 parts by mass, more preferably in the range of 0.05 to 5 parts by mass, and even more preferably in the range of 0.1 to 1.5 parts by mass.

The urethane prepolymer (i) is obtained by reacting the polyol (A), the polyisocyanate (B) and the compound (C), and the hydroxyl groups of the compound (C) are polyisocyanate (B ), a polymerizable unsaturated group is introduced into the molecule, and a crosslinked structure is formed by reacting with moisture present in the air or in the substrate to which the urethane prepolymer is applied. It has an isocyanate group at the end of the molecule.

As a method for producing the urethane prepolymer (i), for example, a polyisocyanate (B) is placed in a reaction vessel containing the polyol (A) and the compound (C), and the isocyanate group of the polyisocyanate (B) is can be produced by reacting under conditions in which is excessive with respect to the hydroxyl groups of the polyol (A) and the compound (C).

When producing the urethane prepolymer (i), the equivalent ratio (isocyanate group/hydroxyl group) between the isocyanate group of the polyisocyanate (B) and the hydroxyl group of the polyol (A) and the compound (C) is , From the point that even better initial adhesive strength and final adhesive strength can be obtained, it is preferably in the range of 1.1 to 10, more preferably in the range of 1.2 to 3, 1.5 to 2.5 A range is more preferred.

Examples of the photopolymerization initiator (ii) include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl] -2-hydroxy-2-methyl-1-propan-1-one, thioxanthone, thioxanthone derivative, 2,2-dimethoxy-1,2-diphenylethan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide , bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl)-butan-1-one and the like can be used. These photopolymerization initiators may be used alone or in combination of two or more.

The amount of the photopolymerization initiator (ii) used is in the range of 0.0001 to 10 parts by mass with respect to 100 parts by mass of the urethane prepolymer (i) in order to obtain even better UV curability. and more preferably in the range of 0.005 to 5 parts by mass.

The moisture-curable urethane hot-melt resin composition of the present invention contains the urethane prepolymer (i) and the photopolymerization initiator (ii) as essential components, and optionally other additives. You may

Examples of other additives include curing catalysts, tackifiers, plasticizers, light stabilizers, fillers, dyes, pigments, fluorescent brighteners, silane coupling agents, waxes, thermoplastic resins, and the like. can be done. These additives may be used alone or in combination of two or more.

Next, the laminated body of this invention is demonstrated.

The laminate of the present invention comprises a substrate and a cured product layer of the moisture-curable urethane hot-melt resin composition.

Examples of the base material include wood base materials such as plywood, MDF (medium density fiberboard), and particle board; metal base materials such as aluminum and iron; polyester, polyamide, polystyrene, polycarbonate, vinyl chloride, and ethylene-vinyl acetate. Sheet base material obtained using resin such as polymer, polyvinyl alcohol, polyethylene, polypropylene; calcium silicate board; paper; metal foil; veneer; fiber base material such as non-woven fabric and woven fabric; Substrate: A glass substrate or the like can be used. The thickness of the base material is determined depending on the application, and is, for example, in the range of 1 to 500 mm.

As a method for applying the moisture-curable urethane hot-melt resin composition on the substrate, for example, the moisture-curable urethane hot-melt resin composition melted at 70 to 140 ° C. is coated with a roll coater, a spray coater, a T - A coater method such as a tie coater, a knife coater, a comma coater; and a method of applying to a substrate using a precision method such as a dispenser, spray, inkjet printing, screen printing, offset printing, and the like.

The thickness of the cured product layer of the moisture-curable urethane hot-melt composition is appropriately determined depending on the intended use, and is, for example, in the range of 0.001 to 3 cm.

The applied moisture-curable urethane hot-melt composition can obtain excellent initial adhesive strength by irradiation with active energy rays. Examples of the active energy rays include ultraviolet rays, electron rays, X-rays, infrared rays, visible rays, and the like. Among these, ultraviolet rays are preferable because initial adhesive strength can be easily obtained.

When irradiating the ultraviolet rays, for example, a light source such as a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a hydrogen lamp, a deuterium lamp, a halogen lamp, a xenon lamp, a carbon arc lamp, and a fluorescent lamp can be used.

The irradiation dose of the ultraviolet rays is 0.05 to 5 J/cm ² , more preferably 0.1 to 3 J/cm ² , particularly preferably 0.3 to 1 J/cm 2 from the viewpoint of obtaining even better initial adhesive strength. It should be in the range of 0.5 J/cm ² . The amount of ultraviolet irradiation is based on a value measured in a wavelength range of 300 to 390 nm using a UV checker "UVR-N1" manufactured by GS Yuasa Corporation.

After the UV irradiation, the isocyanate groups of the urethane prepolymer (i) are aged, so it is preferably cured at a temperature of 10 to 40° C. for 1 to 3 days.

As described above, the moisture-curable urethane hot-melt resin composition of the present invention is excellent in initial adhesive strength and open time.

The present invention will be described in more detail below using examples.

[Example 1]
Alicyclic polyester polyol (neopentyl glycol, 2-methylpropanediol and 1,4-cyclohexanedicarboxylic acid reaction product, number average molecular weight: 1,000, Hereinafter abbreviated as “alicyclic PEs”.) 68.1 parts by mass and 1.3 parts by mass of 2-hydroxyethyl acrylate (hereinafter abbreviated as “HEA”) were charged. Dehydration was carried out until the water content with respect to the total amount was 0.05% by mass.
Then, after cooling to 70° C., 30.6 parts by mass of 4,4′-diphenylmethane diisocyanate (hereinafter abbreviated as “MDI”) was added, and the temperature was raised to 100° C., followed by a photopolymerization initiator (1-hydroxycyclohexyl 1.6 parts by mass of phenyl ketone (hereinafter abbreviated as “HCPK”) is added and reacted at 110° C. for about 3 hours under a nitrogen atmosphere until the isocyanate group content becomes constant to obtain a urethane prepolymer (i-1 ).

[Example 2]
38.9 parts by mass of alicyclic PEs and other polyester polyol (1,6-hexanediol and adipic acid reactant, number average molecular weight: 4,500, 38.9 parts by mass of HEA and 0.9 parts by mass of HEA were charged and dehydrated under reduced pressure heating conditions until the water content in the flask reached 0.05% by mass.
Next, after cooling to 70°C, 21.4 parts by mass of MDI was added, the temperature was raised to 100°C, 1.9 parts by mass of HCPK was added, and the temperature was maintained at 110°C for about 3 hours under a nitrogen atmosphere until the isocyanate group content became constant. A urethane prepolymer (i-2) was obtained by reacting for a certain period of time.

[Example 3]
17 parts by mass of alicyclic PEs, 68 parts by mass of other PEs, and 0.6 parts by mass of HEA were charged in a 2-liter four-necked flask equipped with a stirrer and a thermometer, and under reduced pressure and heating conditions, the water content of the total amount in the flask was 0.05. It dehydrated until it became mass %.
Next, after cooling to 70°C, 14.4 parts by mass of MDI was added, the temperature was raised to 100°C, 2 parts by mass of HCPK was added, and the mixture was reacted at 110°C for about 3 hours under a nitrogen atmosphere until the isocyanate group content became constant. A urethane prepolymer (i-3) was obtained.

[Comparative Example 1]
0.4 parts by mass of HEA and 90.6 parts by mass of other PEs were charged in a 2-liter four-necked flask equipped with a stirrer and a thermometer, and the water content in the flask was 0.05% by mass with respect to the total amount in the flask under reduced pressure and heating conditions. dehydrated until
Next, after cooling to 70°C, 9.1 parts by mass of MDI was added, the temperature was raised to 100°C, 2.2 parts by mass of HCPK was added, and the mixture was heated at 110°C under a nitrogen atmosphere until the isocyanate group content became constant. A urethane prepolymer (iR-1) was obtained by reacting for about 3 hours.

[Method for measuring number average molecular weight]
The number average molecular weights of polyols and the like used in Synthesis Examples and Comparative Synthesis Examples are values measured under the following conditions by gel permeation chromatography (GPC).

Measuring device: high-speed GPC device ("HLC-8220GPC" manufactured by Tosoh Corporation)
Column: The following columns manufactured by Tosoh Corporation were connected in series and used.
"TSKgel G5000" (7.8mm I.D. x 30cm) x 1 "TSKgel G4000" (7.8mm I.D. x 30cm) x 1 "TSKgel G3000" (7.8mm I.D. x 30cm) x 1 Book "TSKgel G2000" (7.8 mm I.D. x 30 cm) x 1 Detector: RI (differential refractometer)
Column temperature: 40°C
Eluent: Tetrahydrofuran (THF)
Flow rate: 1.0 mL/min Injection volume: 100 μL (tetrahydrofuran solution with a sample concentration of 0.4% by mass)
Standard sample: A calibration curve was created 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

[Method for evaluating initial adhesive strength]
(1) Test method for initial peelability The moisture-curable urethane hot-melt resin compositions obtained in Examples and Comparative Examples were each melted at 120°C for 1 hour, and then treated with a corona-treated polyethylene terephthalate base having a thickness of 200 µm. It was coated on the material using a roll coater so as to have a thickness of 100 μm. After that, the coated surface is irradiated with ultraviolet rays of 0.65 J/cm ² using a high-pressure mercury lamp, and a corona-treated polyethylene terephthalate (PET) substrate having a thickness of 200 μm is further laminated to the irradiated surface. After 3 minutes, the 180° peel strength (N/inch) was measured according to JISK7311-1995 and evaluated as follows.
"T"; 50N/inch or more "F"; less than 50N/inch

(2) Test Method for Initial Heat Resistant Creep Resistance Each of the moisture-curable urethane hot-melt resin compositions obtained in Examples and Comparative Examples was melted at 120° C. for 1 hour, and then a roll coater was placed on a polyethylene terephthalate substrate. It was applied so as to have a thickness of 50 μm when used. Thereafter, this coated surface was irradiated with ultraviolet rays of 0.65 J/cm ² using a high-pressure mercury lamp, and MDF (medium density fiberboard) was placed on this irradiated surface and bonded together. Five minutes after bonding, a load of 75 g was applied to a width of 25 mm in a 90° direction in an atmosphere of 35°C, and the peeled length of the polyethylene terephthalate substrate after 15 minutes was measured and evaluated as follows. .
"T"; less than 6 mm "F"; 6 mm or more

[How to evaluate open time]
Each of the moisture-curable urethane hot-melt resin compositions obtained in Examples and Comparative Examples was melted at 120° C. for 1 hour, and then applied to a polypropylene sheet to a thickness of 50 μm. Thereafter, this coated surface was irradiated with ultraviolet rays of 0.65 J/cm ² using a high-pressure mercury lamp. Starting from the point at which the UV irradiation was completed, the time until the kraft paper stopped adhering to the moisture-curable urethane hot-melt resin composition coating surface was measured and evaluated as follows.
"A": More than 300 seconds.
"B": More than 60 seconds and less than or equal to 300 seconds.
"C": More than 30 seconds and 60 seconds or less.
"D": 30 seconds or less.

It was found that the moisture-curable urethane hot-melt resin composition of the present invention has excellent initial adhesive strength and open time.

On the other hand, Comparative Example 1, in which the alicyclic polyol (A) was not used, had poor open time.

Claims (3)

Alicyclic polyester which is a reaction product of one or more aliphatic compounds selected from the group consisting of neopentyl glycol, 2-methylpropanediol, and 3-methyl-1,5-pentanediol and cyclohexanedicarboxylic acid A polyol (A) containing a polyol, a polyisocyanate (B), and a compound (C) having one or more (meth)acryloyl groups and having one hydroxyl group as essential raw materials, and having an isocyanate group A moisture-curable polyurethane hot-melt resin composition comprising a urethane prepolymer (i) and a photopolymerization initiator (ii). 2. The moisture-curable polyurethane hot-melt resin composition according to claim 1, wherein said compound (C) is 2-hydroxyethyl (meth)acrylate. A laminate comprising a substrate and a cured product layer of the moisture-curable urethane hot-melt resin composition according to claim 1 or 2 .