WO2023162931A1 - Structure assemblée, son procédé de production, adhésif thermofusible réactif et vêtement - Google Patents

Structure assemblée, son procédé de production, adhésif thermofusible réactif et vêtement Download PDF

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Publication number
WO2023162931A1
WO2023162931A1 PCT/JP2023/006046 JP2023006046W WO2023162931A1 WO 2023162931 A1 WO2023162931 A1 WO 2023162931A1 JP 2023006046 W JP2023006046 W JP 2023006046W WO 2023162931 A1 WO2023162931 A1 WO 2023162931A1
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WIPO (PCT)
Prior art keywords
polyol
reactive hot
fabric
melt adhesive
adhesive layer
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PCT/JP2023/006046
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English (en)
Japanese (ja)
Inventor
和樹 久野
亮介 大和
花歩 田中
晃一 斉藤
聡一郎 小宮
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株式会社レゾナック
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Publication of WO2023162931A1 publication Critical patent/WO2023162931A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/12—Layered products comprising a layer of synthetic resin next to a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/35—Heat-activated

Definitions

  • the present disclosure relates to a joint structure and its manufacturing method, a reactive hot melt adhesive, and clothing.
  • Patent Document 1 the joining method described in Patent Document 1 is known as a method for joining fabrics that make up clothing.
  • This conventional joining method is a method of joining fabrics constituting clothing by using an adhesive applied in dots.
  • a joint structure in which fabrics are joined via an adhesive layer of a discontinuous shape (a shape that is not continuous in one direction and is interrupted, such as a dot shape, a point shape, a broken line shape, etc.)
  • a continuous shape a shape that is continuous in one direction, such as a linear shape, a curved shape, a planar shape, etc.
  • the adhesive strength between the fabrics is not sufficient due to the decrease in the adhesive area.
  • the main object of the present disclosure is to provide a joint structure having sufficient adhesive strength even when a discontinuous adhesive layer is formed, and a manufacturing method thereof.
  • the method for manufacturing the joint structure includes a first step of applying a reactive hot melt adhesive containing a urethane prepolymer on a first fabric to form an adhesive layer, and an adhesive of the first fabric a second step of placing a second fabric on the layer and joining the first fabric and the second fabric by curing the adhesive layer to obtain a joined structure.
  • a urethane prepolymer has a structural unit derived from a polyol and a structural unit derived from a polyisocyanate.
  • Structural units derived from polyol based on the total amount of structural units derived from polyol, 45% by mass or more of structural units derived from crystalline polyester polyol, and 15 to 50% by mass of structural units derived from polyether polyol. including.
  • the equivalent ratio of the isocyanate groups of the polyisocyanate to the hydroxyl groups of the polyol is 1.80 or more.
  • the urethane prepolymer has a melt viscosity of 6.0 Pa ⁇ s or less at 120°C. According to such a bonding structure manufacturing method, even when a discontinuous adhesive layer is formed, a bonding structure having sufficient bonding strength can be manufactured.
  • the polyol may contain a crystalline polyester polyol having a melting point of 50°C or higher as a crystalline polyester polyol.
  • the shape of the adhesive layer may be discontinuous.
  • the bonding structure can have sufficient adhesive strength even if the shape of the adhesive layer is discontinuous.
  • the shape of the adhesive layer is discontinuous, it is possible to reduce the amount of adhesive used.
  • the first fabric and the second fabric may be elastic fabrics.
  • the adhesive strength between the stretchable fabrics can be improved while maintaining the stretchability of the stretchable fabrics.
  • the reactive hot melt adhesive contains a urethane prepolymer.
  • a urethane prepolymer has a structural unit derived from a polyol and a structural unit derived from a polyisocyanate. Structural units derived from polyol, based on the total amount of structural units derived from polyol, 45% by mass or more of structural units derived from crystalline polyester polyol, and 15 to 50% by mass of structural units derived from polyether polyol. including.
  • the equivalent ratio of the isocyanate groups of the polyisocyanate to the hydroxyl groups of the polyol is 1.80 or more.
  • the urethane prepolymer has a melt viscosity of 6.0 Pa ⁇ s or less at 120°C.
  • the bonding structure includes a first fabric, a second fabric, and an adhesive layer containing a cured product of the reactive hot-melt adhesive provided between the first fabric and the second fabric. and
  • the shape of the adhesive layer may be a discontinuous shape.
  • the clothing includes the joint structure.
  • a second fabric is placed on the adhesive layer of the first fabric, and the first fabric and the second fabric are joined by curing the adhesive layer to obtain a joined structure.
  • the urethane prepolymer has a structural unit derived from a polyol and a structural unit derived from a polyisocyanate,
  • the structural units derived from the polyol are 45% by mass or more of the structural units derived from the crystalline polyester polyol and 15 to 50% by mass of the structural units derived from the polyether polyol, based on the total amount of the structural units derived from the polyol.
  • the equivalent ratio of the isocyanate groups of the polyisocyanate to the hydroxyl groups of the polyol is 1.80 or more
  • the reactive hot melt adhesive has a melt viscosity of 6.0 Pa s or less at 120°C.
  • a method of manufacturing a junction structure [2]
  • the structural unit derived from the crystalline polyester polyol contains a structural unit derived from a crystalline polyester polyol having a melting point of 50°C or higher.
  • a method for manufacturing a joint structure [3]
  • the shape of the adhesive layer is discontinuous, [1] or [2] manufacturing method of the joint structure according to.
  • the first fabric and the second fabric are elastic fabrics, [1] A method for manufacturing a joint structure according to any one of [3].
  • a reactive hot melt adhesive containing a urethane prepolymer has a structural unit derived from a polyol and a structural unit derived from a polyisocyanate,
  • the structural units derived from the polyol are 45% by mass or more of the structural units derived from the crystalline polyester polyol and 15 to 50% by mass of the structural units derived from the polyether polyol, based on the total amount of the structural units derived from the polyol.
  • the equivalent ratio of the isocyanate groups of the polyisocyanate to the hydroxyl groups of the polyol is 1.80 or more,
  • the reactive hot melt adhesive has a melt viscosity of 6.0 Pa s or less at 120°C.
  • Reactive hot melt adhesive [6]
  • the polyol contains a crystalline polyester polyol having a melting point of 50° C. or higher as the crystalline polyester polyol.
  • the shape of the adhesive layer is discontinuous, The joint structure according to [7].
  • the first fabric and the second fabric are elastic fabrics, The joint structure according to [7] or [8]. [10] Provided with the joint structure according to any one of [7] to [9], clothing.
  • a joint structure having sufficient adhesive strength even when a discontinuous adhesive layer is formed, and a manufacturing method thereof are provided.
  • the present disclosure also provides reactive hot melt adhesives that can be used in these. Further, according to the present disclosure, garments are provided comprising such joint structures.
  • FIG. 1 is a schematic diagram showing a manufacturing method of a connection structure of one embodiment
  • FIGS. 1(a), (b), (c), and (d) are schematic diagrams showing each step.
  • polyol means a compound having two or more hydroxyl groups in the molecule.
  • polyisocyanate means a compound having two or more isocyanate groups in the molecule.
  • crystalline and “amorphous” can be judged by the presence or absence of a melting point (Tm) (endothermic peak accompanying melting in DSC (differential scanning calorimetry)).
  • Tm melting point
  • Non-crystalline means having a melting point (Tm)
  • amorphous means not having a melting point (Tm).
  • crystalline polyol means a polyol that has a melting point (Tm)
  • amorphous polyol means a polyol that does not have a melting point (Tm).
  • a numerical range indicated using "-" indicates a range that includes the numerical values before and after "-" as the minimum and maximum values, respectively.
  • the upper limit value or lower limit value of the numerical range at one step may be replaced with the upper limit value or lower limit value of the numerical range at another step.
  • the upper or lower limits of the numerical ranges may be replaced with the values shown in the examples.
  • "A or B” may include either A or B, or may include both.
  • the materials exemplified in this specification can be used singly or in combination of two or more unless otherwise specified.
  • the content of each component in the composition refers to the total amount of the multiple substances present in the composition unless otherwise specified when there are multiple substances corresponding to each component in the composition. means.
  • the reactive hot-melt adhesive of one embodiment is one that can develop adhesive strength and the like by increasing its molecular weight through a chemical reaction.
  • the reactive hot-melt adhesive contains a urethane prepolymer (hereinafter sometimes referred to as "(A) component").
  • Urethane prepolymers are usually urethane prepolymers having isocyanate groups.
  • a reactive hot-melt adhesive containing urethane prepolymer as a main component develops a certain degree of adhesive strength in a short period of time by cooling and solidifying the adhesive itself after application.
  • a reactive hot-melt adhesive can also be called a moisture-curable reactive hot-melt adhesive.
  • the reactive hot-melt adhesive may further contain, for example, a curing catalyst (hereinafter sometimes referred to as "component (B)").
  • the component (A) includes a structural unit derived from a polyol (hereinafter sometimes referred to as "(A1) component”) and a structural unit derived from a polyisocyanate (hereinafter sometimes referred to as "(A2) component”).
  • the (A) component may be, for example, a urethane prepolymer having isocyanate groups.
  • a urethane prepolymer having an isocyanate group usually has a polymer chain containing a structural unit derived from a polyol and a structural unit derived from a polyisocyanate, and an isocyanate group bonded to the end of the polymer chain.
  • the component (A) can usually be obtained by reacting a polyol with a polyisocyanate. That is, component (A) can be a reaction product of polyol and polyisocyanate.
  • component (A) the content of structural units derived from polyol and the content of structural units derived from polyisocyanate are adjusted by adjusting the amount of polyol that provides each structural unit and the amount of polyisocyanate that provides each structural unit. can be done by Moreover, since a urethane bond is formed by reacting a polyol and a polyisocyanate, the polymer chain of the component (A) may have a urethane bond. Also, by increasing the equivalent ratio of the isocyanate groups of the polyisocyanate to the hydroxyl groups of the polyol, isocyanate groups can be introduced at the ends of the polymer chains.
  • the structural units derived from the component (A1) are, based on the total amount of structural units derived from the component (A1), 45% by mass or more of structural units derived from a crystalline polyester polyol, and 15 to 50 % by mass of structural units derived from polyether polyol.
  • the content of the structural unit may be the ratio of the charged amount of the polyol that provides the structural unit to the total charged amount of the component (A1).
  • the content of each structural unit can be adjusted by adjusting the charge amount of the polyol that provides each structural unit.
  • the (A1) component may be, for example, a compound (diol) having two hydroxyl groups in the molecule.
  • the (A1) component-derived structural unit includes a crystalline polyester polyol-derived structural unit.
  • the solidification time and viscosity of the reactive hot-melt adhesive can be adjusted by including the structural unit derived from the crystalline polyester polyol in the structural unit derived from the component (A1).
  • the structural unit derived from the crystalline polyester polyol can impart excellent cohesive force to the component (A) due to its crystallinity, and contributes to the expression of excellent adhesiveness in the crystalline state.
  • polyester polyol will be explained below.
  • crystalline ones can be used as the crystalline polyester polyol that provides structural units derived from the crystalline polyester polyol.
  • the polyester polyol may be a polycondensation reaction product of a polyhydric alcohol and a polycarboxylic acid, or may be a polycondensation reaction product of a dihydric alcohol and a dihydric carboxylic acid.
  • polyhydric alcohols examples include ethylene glycol, 1,2-propanediol, 1,3-propanediol, isomers of butanediol, isomers of pentanediol, isomers of hexanediol, 2,2- Dimethyl-1,3-propanediol, 2-methylpropanediol, 2,4,4-trimethyl-1,6-hexanediol, 2,2,4-trimethyl-1,6-hexanediol, diethylene glycol, dipropylene glycol , triethylene glycol, tripropylene glycol, etc., wherein some of the carbon atoms ( --CH.sub.2 --(methylene group)) may be substituted with oxygen atoms (--O--); 1,4 - Alicyclic dihydric alcohols such as cyclohexanediol and 1,4-cyclohexanedimethanol; dihydric alcohol having) and the like.
  • polyhydric alcohol may be used alone, or two or more types may be used in combination.
  • the polyhydric alcohol is preferably an aliphatic dihydric alcohol in which some carbon atoms may be substituted with oxygen atoms, more preferably a dihydric alcohol having 2 to 6 carbon atoms. be.
  • polycarboxylic acids examples include aromatic polycarboxylic acids (polycarboxylic acids having an aromatic ring) such as phthalic acid, isophthalic acid, terephthalic acid, and 1,2,4-benzenetricarboxylic acid; Aliphatic polycarboxylic acids such as acid, aconitic acid, 1,2,3-propanetricarboxylic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, azelaic acid, sebacic acid; cyclohexane-1,2- Dicarboxylic acids, alicyclic polyvalent carboxylic acids such as 1,4-cyclohexanediene-1,2-dicarboxylic acid, and the like.
  • aromatic polycarboxylic acids polycarboxylic acids having an aromatic ring
  • Aliphatic polycarboxylic acids such as acid, aconitic acid, 1,2,3-propanetricarboxylic acid, malonic acid, succinic acid,
  • the aromatic polycarboxylic acid may be a polycarboxylic acid having a benzene ring and two or more carboxy groups bonded to the benzene ring, and is a group consisting of phthalic acid, isophthalic acid, and terephthalic acid. It may be at least one selected from.
  • Polyvalent carboxylic acid may be used individually by 1 type, and may be used in combination of 2 or more type. Among these, the polyvalent carboxylic acid is preferably an aliphatic divalent carboxylic acid or an aromatic divalent carboxylic acid, more preferably 2 to 6 carbon atoms (excluding the carbon atoms constituting the carboxylic acid). is a dihydric alcohol with
  • Polyvalent carboxylic acid derivatives such as carboxylic acid anhydrides and compounds in which a part of the carboxyl groups are esterified can be used instead of the polyvalent carboxylic acids.
  • Examples of polyvalent carboxylic acid derivatives include phthalic anhydride, dimethyl terephthalate, dodecyl maleic acid, octadecenyl maleic acid and the like.
  • the polyester polyol may have a number average molecular weight (Mn) of 500 to 12,000 from the viewpoint of adhesion.
  • the number average molecular weight (Mn) of the polyester polyol may be 1000 or more, 1500 or more, or 1800 or more, and may be 10000 or less, 8000 or less, or 6000 or less.
  • Mn is a value measured by gel permeation chromatography (GPC) and converted into standard polystyrene.
  • GPC measurement for determining the number average molecular weight (Mn) can be performed, for example, under the following conditions.
  • a structural unit derived from a crystalline polyol may contain a structural unit derived from a crystalline polyester polyol having a melting point of 50°C or higher, since the adhesive strength of the reactive hot-melt adhesive is superior.
  • the melting point of the crystalline polyol may be 52° C. or higher, or 55° C. or higher, and may be 100° C. or lower, 80° C. or lower, or 70° C. or lower.
  • the melting point (Tm) can be determined by DSC (differential scanning calorimetry).
  • the structural units derived from the crystalline polyol are more preferably composed only of structural units derived from the crystalline polyester polyol having a melting point of 50°C or higher.
  • the content of the structural units derived from the crystalline polyester polyol is 45% by mass or more based on the total amount of the structural units derived from the component (A1), since the adhesive strength of the reactive hot-melt adhesive is excellent, and 55 It may be at least 60% by mass or at least 60% by mass.
  • the content of structural units derived from the crystalline polyester polyol may be 85% by mass or less or 80% by mass or less based on the total amount of structural units derived from the component (A1).
  • the structural unit derived from the (A1) component includes a structural unit derived from polyether polyol.
  • a structural unit derived from a polyether polyol in the structural unit derived from the component (A1), the melt viscosity and open time of the reactive hot-melt adhesive can be adjusted, and excellent workability, adhesiveness, It tends to be able to impart waterproofness and flexibility.
  • polyether polyols examples include polyethylene glycol, polypropylene glycol, polybutylene glycol, polytetramethylene glycol, ethylene oxide-modified polypropylene glycol, and alkylene oxide-modified bisphenol.
  • the number average molecular weight of the polyether polyol may be 500 to 6000, 700 to 5500, or 1000 to 5000 from the viewpoint of initial adhesive strength, adhesive strength after curing, and appropriate open time after application.
  • the content of structural units derived from polyether polyol is 15 to 50% by mass based on the total amount of structural units derived from component (A1), since it is easy to suppress the increase in the melt viscosity of the reactive hot-melt adhesive. is.
  • the content of the structural units derived from the polyether polyol may be 18% by mass or more or 20% by mass or more, and 45% by mass or less or 40% by mass, based on the total amount of the structural units derived from the component (A1). may be:
  • the structural units derived from component (A1) may contain structural units derived from other polyols in addition to structural units derived from crystalline polyester polyols and structural units derived from polyether polyols.
  • polystyrene resin examples include amorphous polyester polyols, polyetherester polyols, polyurethane polyols, polycarbonate polyols, and polyolefin polyols.
  • other polyols may be amorphous polyester polyols.
  • amorphous polyester polyols can be used as the amorphous polyester polyol.
  • the content of structural units derived from other polyols is 0 to 40% by mass, 0 to 30% by mass or more, 0 to 20% by mass, or 0 to 10% by mass, based on the total amount of structural units derived from component (A1). % by mass.
  • (A2) Component Polyisocyanate
  • (A2) component that provides structural units derived from the (A2) component include aromatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates.
  • Aromatic polyisocyanates include, for example, 1,3- or 1,4-phenylene diisocyanate, 2,4- or 2,6-tolylene diisocyanate, 2,4'- or 4,4'-diphenylmethane diisocyanate, 4, 4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatodiphenylmethane, 1,5-naphthylene diisocyanate, 4,4′,4′′-triphenylmethane triisocyanate, m- or p-isocyanatophenylsulfonyl isocyanate, m- or p-xylylene diisocyanate, ⁇ , ⁇ , ⁇ ′, ⁇ ′-tetramethylxylylene diisocyanate etc.
  • aliphatic polyisocyanates examples include ethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate, 1,6,11-undecane triisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, 2, 6-diisocyanatomethylcaproate, bis(2-isocyanatoethyl)fumarate, bis(2-isocyanatoethyl)carbonate, 2-isocyanatoethyl-2,6-diisocyanatohexanoate and the like.
  • alicyclic polyisocyanates examples include isophorone diisocyanate, dicyclohexylmethane-4,4′-diisocyanate, cyclohexylene diisocyanate, methylcyclohexylene diisocyanate, bis(2-isocyanatoethyl)-4-cyclohexene-1,2-diisocyanate, carboxylate, 2,5- or 2,6-norbornane diisocyanate, and the like.
  • the (A2) component may be, for example, a compound (diisocyanate) having two isocyanate groups.
  • the component (A2) may contain an aromatic diisocyanate or diphenylmethane diisocyanate from the viewpoint of moisture curing speed. That is, the structural unit derived from the component (A2) may contain a structural unit derived from an aromatic diisocyanate, more preferably a structural unit derived from diphenylmethane diisocyanate.
  • the (A) component can be synthesized by reacting the (A1) component and the (A2) component.
  • Component (A) has, for example, a polymer chain containing a structural unit derived from component (A1) and a structural unit derived from component (A2), and an isocyanate group bonded to the end of the polymer chain.
  • the equivalent ratio of the isocyanate group (NCO) of the component (A2) to the hydroxyl group (OH) of the component (A1) (the isocyanate group (NCO) equivalent of the component (A2) (gram equivalent) / ( The hydroxyl group (OH) equivalent (gram equivalent), NCO/OH) of component A1) is 1.80 or more, and may be 1.85 or more or 1.90 or more.
  • the NCO/OH ratio is 1.80 or more
  • component (A) has an isocyanate group bonded to the end of the polymer chain, and an increase in the melt viscosity of the reactive hot-melt adhesive tends to be suppressed. be.
  • NCO/OH can be, for example, 2.50 or less, 2.30 or less, or 2.10 or less.
  • foaming is less likely to occur during the moisture-curing reaction of the reactive hot-melt adhesive, which tends to make it easier to suppress a decrease in adhesive strength.
  • component (B) curing catalyst>
  • the reactive hot-melt adhesive accelerates the curing of component (A) (high molecular weight due to the reaction between the isocyanate group of component (A) and moisture (moisture in the air or on the surface of the adherend)), resulting in higher adhesion.
  • the component (B) may be further contained.
  • Examples of component (B) include dibutyltin dilaurate, dibutylthione octate, dimethylcyclohexylamine, dimethylbenzylamine, trioctylamine, and dimorpholinodiethyl ether (bis(2-morpholinoethyl) ether).
  • the content of component (B) may be 0.01 to 0.5 parts by mass when the total amount of component (A) is 100 parts by mass.
  • the reactive hot melt adhesive may further contain a thermoplastic polymer from the viewpoint of increasing the rubber elasticity of the formed adhesive layer and further improving the impact resistance.
  • thermoplastic polymers include polyurethanes, ethylene-based copolymers, propylene-based copolymers, vinyl chloride-based copolymers, acrylic copolymers, and styrene-conjugated diene block copolymers.
  • the content of the thermoplastic polymer may be 0.1-20% by weight, based on the total amount of the reactive hot melt adhesive.
  • the reactive hot-melt adhesive may further contain a tackifying resin from the viewpoint of imparting stronger adhesion to the formed adhesive layer.
  • tackifying resins include rosin resins, rosin ester resins, hydrogenated rosin ester resins, terpene resins, terpene phenol resins, hydrogenated terpene resins, petroleum resins, hydrogenated petroleum resins, coumarone resins, ketone resins, styrene resins, Modified styrene resins, xylene resins, epoxy resins and the like can be mentioned.
  • the content of the tackifying resin may be 0.1-20% by weight based on the total amount of the reactive hot melt adhesive.
  • the reactive hot melt adhesive may further contain other components as necessary.
  • Other components include, for example, antifoaming agents, nucleating agents, plasticizers, pigments, surfactants, flame retardants, fillers, photocoloring agents, thermal coloring inhibitors, fragrances, imaging agents, thermal crosslinking agents, and the like. mentioned.
  • the content of other components may be 0.001 to 10% by mass based on the total amount of the reactive hot melt adhesive.
  • Reactive hot-melt adhesives are prepared by, for example, reacting components (A1) and (A2) to synthesize component (A), the synthesized component (A), component (B), and the like. mixing to obtain a reactive hot melt adhesive.
  • the temperature and time for reacting component (A1) and component (A2) when synthesizing component (A) are not particularly limited, but may be, for example, 85 to 120° C. for 0.1 minute to 48 hours. .
  • the melt viscosity of the reactive hot melt adhesive at 120°C is 6.0 Pa ⁇ s or less from the viewpoint of improving the applicability.
  • the melt viscosity at 120° C. may be 5.5 Pa ⁇ s or less, 5.2 Pa ⁇ s or less, or 5.0 Pa ⁇ s or less.
  • the lower limit of the melt viscosity at 120°C is not particularly limited, it may be, for example, 0.1 Pa ⁇ s or more.
  • the melt viscosity of the reactive hot-melt adhesive at 120° C. is measured with a rotary viscometer (for example, TVB-25H type viscometer (manufactured by Toki Sangyo Co., Ltd.)) using a No. 4 rotor. means the melt viscosity measured under the conditions of a rotor speed of 50 rpm and a reactive hot melt adhesive sample amount of 15 g.
  • the melt viscosity of the reactive hot-melt adhesive at 120°C increases the ratio of the polyether polyol in the component (A1) within a predetermined range. ) can be added to lower the value.
  • Reactive hot-melt adhesives react with moisture in the air or moisture on the surface of the adherend. It can be cured by leaving (curing) at RH (relative humidity) for 24 hours or longer. Thus, a cured product of reactive hot-melt adhesive can be obtained.
  • a reactive hot-melt adhesive can be melted at 60-130°C and then applied, for example, to form an adhesive layer.
  • the coating method is not particularly limited, and examples thereof include a method using a coating device such as a bar coater, a die coater, a roll coater, and a sprayer.
  • a dispenser is suitable for application to narrow areas such as small parts.
  • the application pattern of the reactive hot-melt adhesive can be appropriately set, and examples thereof include a continuous pattern and a discontinuous pattern.
  • a continuous shape means a shape that is continuous in at least one direction. Examples of the continuous shape include linear, curved, planar, and the like.
  • a discontinuous shape means a shape that is not continuous in one direction and is interrupted.
  • the application pattern of the reactive hot-melt adhesive can be dot-like, for example.
  • a continuous adhesive layer can be obtained, and when the application pattern is discontinuous, a discontinuous adhesive layer can be obtained.
  • the shape of the adhesive layer may be, for example, dot-like.
  • a reactive hot-melt adhesive can obtain a joint structure by joining the first fabric and the second fabric via the cured product (adhesive layer) of the reactive hot-melt adhesive.
  • the material of the first fabric and the material of the second fabric include polyester, polyurethane, acrylic, cotton, nylon, composite fabrics combining these, and the like.
  • the first fabric and the second fabric may be, for example, elastic fabrics.
  • Stretchable fabrics include, for example, stretchable knitted fabrics (warp knitted fabrics, circular knitted fabrics, weft knitted fabrics, etc.) and stretchable woven fabrics.
  • Elastic knitted fabrics include velor and jersey (cotton jersey, wool jersey) and the like.
  • stretchable fabrics include polyurethane elastic fibers, mixed fibers containing polyurethane elastic fibers, and the like. These stretchable fabrics may have stretchability in at least one direction, and may have stretchability in multiple directions.
  • the type of the first fabric and the type of the second fabric may be the same or different.
  • Reactive hot-melt adhesives can be suitably used for bonding elastic fabrics together, and can be particularly suitably used for clothing such as clothes (apparel products).
  • the elasticity can be sufficiently improved, but compared to the case of a continuous adhesive layer, the bonding area is increased. A decrease in the adhesive strength tends to result in insufficient adhesive strength between fabrics.
  • the reactive hot-melt adhesive of this embodiment can ensure sufficient adhesive strength even when applied to such a bonding structure.
  • the reactive hot melt adhesive may be formed into a film and used as an adhesive film.
  • Such an adhesive film can be obtained, for example, by applying a reactive hot-melt adhesive onto a support film such as a PET (polyethylene terephthalate) film to form an adhesive layer. can be done.
  • the thickness of the adhesive layer may be 10 ⁇ m or more, 20 ⁇ m or more, or 30 ⁇ m or more, and may be 500 ⁇ m or less, 400 ⁇ m or less, or 300 ⁇ m or less. The thicker the film, the more adhesive force can be secured, and the thinner the film, the easier it is to ensure stretchability.
  • the adhesive film can be used after being molded into any shape.
  • a bonding structure of one embodiment contains a first fabric, a second fabric, and a cured product of the reactive hot melt adhesive provided between the first fabric and the second fabric. and an adhesive layer.
  • Articles having a joint structure include, for example, clothing (especially seamless clothing).
  • the bonding structure of this embodiment includes a first step of applying the reactive hot-melt adhesive containing a predetermined urethane prepolymer on a first fabric to form an adhesive layer; a second step of placing a second fabric on the adhesive layer of and curing the adhesive layer to join the first fabric and the second fabric to obtain a joined structure can do.
  • the reactive hot-melt adhesive When applying a reactive hot-melt adhesive, the reactive hot-melt adhesive is usually melted and then applied.
  • the temperature for melting the reactive hot melt adhesive may be, for example, 60-130°C.
  • Examples of the method of applying the reactive hot-melt adhesive to the first fabric include methods using a coating device such as a die coater, a roll coater, and a sprayer.
  • a dispenser is suitable for application to narrow areas such as small parts.
  • the application pattern of the reactive hot-melt adhesive can be appropriately set, and examples thereof include a continuous pattern and a discontinuous pattern.
  • the second fabric When placing the second fabric on the adhesive layer of the first fabric, the second fabric may be crimped.
  • a method of crimping the second fabric for example, a method of crimping using a pressure roll or the like can be mentioned.
  • the adhesive layer composed of reactive hot-melt adhesive is dried, for example, at a temperature of 23° C. and 50% RH (relative humidity) for 24 hours. It can be hardened by leaving (curing). Thereby, the adhesive layer can contain a cured product of the reactive hot-melt adhesive.
  • FIG. 1 is a schematic diagram showing the manufacturing method of the connection structure of one embodiment
  • FIGS. 1(a), (b), (c), and (d) are schematic diagrams showing each step. A method for manufacturing the connection structure will be described below with reference to FIG.
  • the first cloth 1 is placed along the jig 10 (see (a) of FIG. 1).
  • the reactive hot-melt adhesive of this embodiment is applied to a predetermined portion of the first fabric 1 to form an adhesive layer 4 (see FIG. 1(b)).
  • the material and shape of the jig 10 are not particularly limited, and can be appropriately selected according to the purpose.
  • Application of the reactive hot melt adhesive may be performed, for example, using a dispenser.
  • the application pattern of the reactive hot-melt adhesive may be a continuous shape that is continuous in at least one direction, or a discontinuous shape that is not continuous in one direction. .
  • the reactive hot-melt adhesive of the present embodiment exhibits sufficient adhesive strength even when a discontinuous adhesive layer is formed.
  • the adhesive layer 4 can have a predetermined shape according to the application pattern of the reactive hot-melt adhesive.
  • the shape of the adhesive layer shown in (b) of FIG. 1 is a continuous shape (planar shape).
  • the second fabric 2 is placed on the adhesive layer 4, and pressure is applied from the top of the second fabric 2 by a roll or the like to bond the first fabric 1 and the second fabric 2 together with the adhesive. They are bonded together via the layer 4 to obtain a crimped structure 20 which is a precursor of the bonded structure (see (c) and (d) of FIG. 1).
  • the adhesive layer 4 composed of the reactive hot-melt adhesive is moisture-cured, and a joint structure in which the elastic fabrics are joined can be obtained.
  • the adhesive layer 4 in the bonding structure contains a cured product of the reactive hot-melt adhesive because the curing of the reactive hot-melt adhesive is progressing.
  • an adhesive film made of a reactive hot-melt adhesive which is formed in advance on a release base material and molded into an arbitrary shape, is transferred onto the first fabric 1 and adhered.
  • An agent layer 4 may be formed.
  • a garment of one embodiment comprises the joint structure described above.
  • the garment may be a seamless garment.
  • Examples 1 to 8 and Comparative Examples 1 to 6 [Preparation of reactive hot melt adhesive] Using polyol ((A1) component), polyisocyanate ((A2) component), and curing catalyst ((B) component) of the types and parts by mass shown in Tables 1 and 2, Examples 1 to 8 and Comparative Examples 1-6 reactive hot melt adhesives were prepared. More specifically, the (A2) component is added to the reaction vessel and mixed at 110 ° C. for 1 hour to the (A1) component that has been dehydrated in advance by a vacuum dryer, and the (A1) component and the (A2) component are mixed. reacted in the system. Next, after adding the component (B), defoaming under reduced pressure at 110° C.
  • A2 Polyisocyanate (A2-1) Diphenylmethane diisocyanate (manufactured by Tosoh Corporation, trade name: Millionate MT, number of isocyanate groups: 2, molecular weight: 250, isocyanate group equivalent: 125 g/eq)
  • test sample was subjected to a T-type peel strength test using a tensile tester (EZ-Test EZ-SX, manufactured by Shimadzu Corporation) under the conditions of a measurement temperature of 25 ° C. and a tensile speed of 100 mm / min. The maximum value obtained was taken as the adhesive strength of the joint structure.
  • a tensile tester EZ-Test EZ-SX, manufactured by Shimadzu Corporation
  • the bonding structures using the reactive hot-melt adhesives of Examples 1-8 that satisfy the predetermined conditions are the reactive hot-melt adhesives of Comparative Examples 1-6 that do not satisfy the predetermined conditions. It was superior in terms of adhesive strength compared to a bonding structure using an agent. Since the reactive hot melt adhesives of Examples 1 to 8 have sufficient adhesive strength, it can be expected to have sufficient adhesive strength even when a discontinuous adhesive layer is formed. These results suggest that the bonding structure of the present disclosure has sufficient bonding strength even when a discontinuous adhesive layer is formed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une structure assemblée qui comprend un premier tissu, un second tissu et une couche adhésive qui est disposée entre le premier tissu et le second tissu et contient un produit durci d'un adhésif thermofusible réactif. L'adhésif thermofusible réactif contient un prépolymère d'uréthane qui a des motifs structuraux dérivés d'un polyol et des motifs structuraux dérivés d'un polyisocyanate. Le polyol comprend, par rapport à la quantité totale de celui-ci, au moins 45 % en masse d'un polyester polyol cristallin et 15 à 50 % en masse d'un polyéther polyol. Dans le prépolymère d'uréthane, le rapport équivalent des groupes isocyanate du polyisocyanate aux groupes hydroxyle du polyol est d'au moins 1,80. La viscosité à l'état fondu de l'adhésif thermofusible réactif à 120 °C n'est pas supérieure à 6,0 Pa⋅s.
PCT/JP2023/006046 2022-02-22 2023-02-20 Structure assemblée, son procédé de production, adhésif thermofusible réactif et vêtement WO2023162931A1 (fr)

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Citations (6)

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Publication number Priority date Publication date Assignee Title
JP2014196587A (ja) * 2013-03-05 2014-10-16 グンゼ株式会社 アンダーシャツ
CN112646534A (zh) * 2020-12-24 2021-04-13 上海回天新材料有限公司 一种智能穿戴产品用湿固化聚氨酯热熔胶及其制备方法
JP2021095489A (ja) * 2019-12-17 2021-06-24 東洋インキＳｃホールディングス株式会社 湿気硬化型ホットメルト接着剤、該接着剤を用いてなる本、および本の製造方法
JP2021172769A (ja) * 2020-04-28 2021-11-01 昭和電工マテリアルズ株式会社 反応性ホットメルト接着剤組成物
JP2021172772A (ja) * 2020-04-28 2021-11-01 昭和電工マテリアルズ株式会社 反応性ホットメルト接着剤組成物
JP2022112188A (ja) * 2021-01-21 2022-08-02 Dic株式会社 湿気硬化型ポリウレタンホットメルト樹脂組成物、及び、接着剤

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014196587A (ja) * 2013-03-05 2014-10-16 グンゼ株式会社 アンダーシャツ
JP2021095489A (ja) * 2019-12-17 2021-06-24 東洋インキＳｃホールディングス株式会社 湿気硬化型ホットメルト接着剤、該接着剤を用いてなる本、および本の製造方法
JP2021172769A (ja) * 2020-04-28 2021-11-01 昭和電工マテリアルズ株式会社 反応性ホットメルト接着剤組成物
JP2021172772A (ja) * 2020-04-28 2021-11-01 昭和電工マテリアルズ株式会社 反応性ホットメルト接着剤組成物
CN112646534A (zh) * 2020-12-24 2021-04-13 上海回天新材料有限公司 一种智能穿戴产品用湿固化聚氨酯热熔胶及其制备方法
JP2022112188A (ja) * 2021-01-21 2022-08-02 Dic株式会社 湿気硬化型ポリウレタンホットメルト樹脂組成物、及び、接着剤

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