WO2020166414A1 - 反応性ホットメルト接着剤組成物、並びに接着体及びその製造方法 - Google Patents
反応性ホットメルト接着剤組成物、並びに接着体及びその製造方法 Download PDFInfo
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- WO2020166414A1 WO2020166414A1 PCT/JP2020/003974 JP2020003974W WO2020166414A1 WO 2020166414 A1 WO2020166414 A1 WO 2020166414A1 JP 2020003974 W JP2020003974 W JP 2020003974W WO 2020166414 A1 WO2020166414 A1 WO 2020166414A1
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4202—Two or more polyesters of different physical or chemical nature
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
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- C09J175/06—Polyurethanes from polyesters
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
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- 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
- C09J7/38—Pressure-sensitive adhesives [PSA]
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- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
- C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/304—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C
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- C09J2469/00—Presence of polycarbonate
- C09J2469/006—Presence of polycarbonate in the substrate
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- C09J2479/00—Presence of polyamine or polyimide
- C09J2479/02—Presence of polyamine or polyimide polyamine
- C09J2479/026—Presence of polyamine or polyimide polyamine in the substrate
Definitions
- the present invention relates to a reactive hot melt adhesive composition, an adhesive body and a method for producing the same.
- hot-melt adhesives are solvent-free adhesives, there is little load on the environment and the human body, and they can be bonded in a short time, making them suitable for improving productivity.
- the hot melt adhesive can be roughly classified into two types, one containing a thermoplastic resin as a main component and one containing a reactive resin as a main component.
- a reactive resin a urethane prepolymer having an isocyanate group at the end is mainly used.
- Reactive hot melt adhesives containing urethane prepolymer as the main component develop a certain degree of adhesive strength in a short time after application by cooling and solidifying the adhesive itself. Thereafter, the terminal isocyanate group of the urethane prepolymer reacts with moisture (in the air or the moisture on the surface of the adherend) to increase the molecular weight, and crosslinks to generate heat resistance.
- moisture-curable reactive hot melt adhesive Such an adhesive is referred to as a "moisture-curable reactive hot melt adhesive”.
- a reactive hot melt adhesive containing a urethane prepolymer as a main component exhibits good adhesive strength even when heated.
- a reactive hot melt adhesive composition containing a urethane prepolymer, a thermoplastic resin, and a tackifier is also known in order to improve the adhesive strength in the initial stage and after the curing (for example, Patent Documents 1 to 3). reference).
- the conventional reactive hot melt adhesive composition may not be able to obtain sufficient adhesive strength depending on the type of the substrate to be applied, and there is room for further improvement in the adhesive strength with a polyamide substrate. is there.
- the main object of the present invention is to provide a reactive hot melt adhesive composition that exhibits sufficient adhesive strength even when applied to a polyamide substrate.
- One aspect of the present invention includes a urethane prepolymer having a polymer chain containing a structural unit derived from a polyol and a structural unit derived from a polyisocyanate, having an isocyanate group as a terminal group of the polymer chain, and a functional group-protected silane cup.
- a reactive hot melt adhesive composition containing a ring agent is provided. Such a reactive hot melt adhesive composition can exhibit sufficient adhesive strength even when applied to a polyamide substrate.
- the content of the functional group-protected silane coupling agent may be 0.4 to 5 parts by mass based on 100 parts by mass of the total amount of the urethane prepolymer.
- Another aspect of the present invention is the above-mentioned reactive hot melt bonding, in which a first adherend, a second adherend, and a first adherend and a second adherend are adhered to each other.
- a cured product of the agent composition is provided.
- Another aspect of the present invention is to melt the reactive hot melt adhesive composition described above and apply it to a first adherend to form an adhesive layer, and a second step on the adhesive layer.
- Manufacture of an adhesive body which comprises a step of arranging an adherend and a pressure-bonding of a second adherend to obtain an adhesive body precursor, and a step of curing an adhesive layer in the obtained adhesive body precursor. Provide a way.
- a reactive hot melt adhesive composition that exhibits sufficient adhesive strength even when applied to a polyamide substrate. Further, according to the present invention, an adhesive body using such a reactive hot melt adhesive composition and a method for producing the same are provided.
- 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.
- the reactive hot melt adhesive composition of one embodiment contains a urethane prepolymer and a functional group-protecting silane coupling agent.
- the reactive hot melt adhesive composition is a moisture-curable type, by reacting with water in the air or water on the surface of the adherend, the urethane prepolymer mainly has a high molecular weight, The adhesive strength and the like can be expressed.
- the urethane prepolymer includes a polymer chain containing a structural unit derived from a polyol and a structural unit derived from a polyisocyanate, and has an isocyanate group as a terminal group of the polymer chain. That is, the urethane prepolymer of this embodiment is a reaction product of a polyol and a polyisocyanate, and has an isocyanate group as a terminal group of the reaction product.
- the adhesive composition of the present embodiment can exhibit excellent adhesive strength after moisture curing.
- the polyol can be used without particular limitation as long as it is a compound having two or more hydroxyl groups.
- the polyol may contain a polyester polyol and a polyether polyol from the viewpoint of further improving the adhesive strength.
- the urethane prepolymer may include a polymer chain including a structural unit derived from polyester polyol, a structural unit derived from polyether polyol, and a structural unit derived from polyisocyanate.
- the solidification time and viscosity of the adhesive composition can be adjusted by including the structural unit derived from the polyester polyol in the polymer chain.
- the polyester polyol a compound produced by a polycondensation reaction between a polyhydric alcohol and a polycarboxylic acid can be used.
- the polyester polyol has, for example, a polyhydric alcohol having 2 to 15 carbon atoms and 2 or 3 hydroxyl groups, 2 to 14 carbon atoms (including carbon atoms in a carboxyl group), and 2 to 3 carbon atoms. It may be a polycondensate with a polycarboxylic acid having 6 carboxyl groups.
- the polyester polyol may be a linear polyester diol produced from a diol and a dicarboxylic acid, or a branched polyester triol produced from a triol and a dicarboxylic acid.
- the branched polyester triol can also be obtained by reacting a diol with a tricarboxylic acid.
- polyhydric alcohols examples include ethylene glycol, 1,2-propanediol, 1,3-propanediol, butanediol isomers, pentanediol isomers, hexanediol isomers, 2,2- Dimethyl-1,3-propanediol, 2-methylpropanediol, 2,4,4-trimethyl-1,6-hexanediol, 2,2,4-trimethyl-1,6-hexanediol, 1,4-cyclohexane Aliphatic or alicyclic diols such as diols and 1,4-cyclohexanedimethanol; aromatic diols such as 4,4′-dihydroxydiphenylpropane, bisphenol A, bisphenol F, pyrocatechol, resorcinol and hydroquinone.
- the polyhydric alcohol may be used alone or in combination of two or more. Of these, aliphatic diols are prefer
- polycarboxylic acid examples include aromatic polycarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid and 1,2,4-benzenetricarboxylic acid; maleic acid, fumaric acid, aconitic acid, 1,2,3-propane. Aliphatics such as tricarboxylic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, cyclohexane-1,2-dicarboxylic acid, 1,4-cyclohexanediene-1,2-dicarboxylic acid Alternatively, alicyclic polycarboxylic acid and the like can be mentioned.
- the polycarboxylic acids may be used alone or in combination of two or more.
- a polycarboxylic acid derivative such as a carboxylic acid anhydride or a compound in which a part of the carboxyl group is esterified can be used.
- the polycarboxylic acid derivative include dodecyl maleic acid and octadecenyl maleic acid.
- the polyester polyol may be a crystalline polyester polyol or an amorphous polyester polyol.
- a crystalline polyester polyol means a polyester polyol which is crystalline at 25°C
- an amorphous polyester polyol means a polyester polyol which is amorphous at 25°C.
- the polyol may include both a crystalline polyester polyol and an amorphous polyester polyol.
- the number average molecular weight (Mn) of the crystalline polyester polyol is preferably 500 to 10000, more preferably 800 to 9000, and still more preferably 1000 to 8000 from the viewpoint of improving waterproofness and adhesive strength. is there.
- the number average molecular weight is a value measured by gel permeation chromatography (GPC) and converted into standard polystyrene. GPC measurement can be performed under the following conditions.
- Examples of the amorphous polyester polyol include an amorphous polyester polyol having a number average molecular weight of 3000 or less and an amorphous polyester polyol having a number average molecular weight of 5000 or more.
- Mn of the amorphous polyester polyol having a number average molecular weight of 3,000 or less is preferably in the range of 500 to 3000, more preferably 1000 to 3000.
- the Mn of the amorphous polyester polyol having a number average molecular weight of 5,000 or more is preferably in the range of 5,000 to 9000, more preferably 7,000 to 8,000, from the viewpoint of improving impact resistance.
- the polyester polyols may be used alone or in combination of two or more. From the viewpoint of further improving the adhesive strength, the content of the polyester polyol is preferably 70 to 90 parts by mass, more preferably 75 to 85 parts by mass, based on 100 parts by mass of the total amount of the polyol.
- polyether polyol By including the structural unit derived from the polyether polyol in the polymer chain, it becomes possible to adjust the appropriate melt viscosity and open time after application of the adhesive composition, and excellent workability, adhesiveness, waterproofness, and flexibility. Can be given.
- the polyether polyol include polyethylene glycol, polypropylene glycol, polybutylene glycol, polytetramethylene glycol, ethylene oxide modified polypropylene glycol and the like.
- the Mn of the polyether polyol is preferably in the range of 500 to 5000, more preferably 700 to 4500, and further preferably 1000 from the viewpoint of the initial adhesive strength, the adhesive strength after curing, and the appropriate open time after coating.
- the range is up to 4000.
- the polyether polyols may be used alone or in combination of two or more.
- the content of the polyether polyol is preferably 10 to 30 parts by mass with respect to 100 parts by mass of the total amount of the polyol, since it is easy to adjust the viscosity of the adhesive composition to be low and the adhesive strength to the adherend is improved. , And more preferably 15 to 25 parts by mass.
- the polyol may include a polyol other than the polyester polyol and the polyether polyol.
- the polyisocyanate can be used without particular limitation as long as it is a compound having two or more isocyanate groups.
- polyisocyanates include aromatic isocyanates such as diphenylmethane diisocyanate, dimethyldiphenylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate and p-phenylene diisocyanate; alicyclic isocyanates such as dicyclohexylmethane diisocyanate and isophorone diisocyanate; hexamethylene diisocyanate and the like. And aliphatic isocyanates thereof.
- the polyisocyanate preferably contains an aromatic diisocyanate, more preferably diphenylmethane diisocyanate.
- an aromatic diisocyanate more preferably diphenylmethane diisocyanate.
- the polyisocyanate one type may be used alone, or two or more types may be used in combination.
- Urethane prepolymer can be synthesized by reacting polyol and polyisocyanate.
- the urethane prepolymer of this embodiment includes a polymer chain containing a structural unit derived from a polyol and a structural unit derived from a polyisocyanate, and has an isocyanate group as a terminal group of the polymer chain.
- the ratio of the isocyanate group (NCO) equivalent of polyisocyanate to the hydroxyl group (OH) of polyol (isocyanate group (NCO) equivalent of polyisocyanate/hydroxyl group (OH) equivalent of polyol, NCO/ OH) is greater than 1, preferably 1.5 to 3.0, more preferably 1.8 to 2.5.
- the NCO/OH ratio When the NCO/OH ratio is 1.5 or more, the viscosity of the urethane prepolymer obtained is prevented from becoming too high, and workability tends to be improved. When the NCO/OH ratio is 3.0 or less, foaming is less likely to occur during the moisture curing reaction of the adhesive composition, and the decrease in adhesive strength tends to be suppressed easily.
- a functional group-protected silane coupling agent is a silane coupling agent having a functional group such as a mercapto group and a hydroxy group, in which the functional group is protected by a protective group.
- the protective group is preferably one that reacts with moisture to be eliminated.
- the functional group is protected by a protective group, and the functional group-protected silane coupling agent also reacts with moisture at the stage where the urethane prepolymer in the adhesive composition reacts with moisture to cure. It is considered that the above is eliminated and a functional group capable of acting with a base material such as a polyamide base material or a urethane prepolymer is generated.
- Examples of the functional group-protected silane coupling agent include compounds represented by the following general formula (1).
- R 1 represents an alkoxy group, and a plurality of R 1 may be the same or different.
- E represents a group containing a nitrogen atom or a sulfur atom, and X represents a protecting group.
- n represents an integer of 1 to 10.
- Examples of the alkoxy group represented by R 1 include a methoxy group and an ethoxy group. Plural R 1 s are preferably the same.
- E is preferably a sulfur atom because it is more excellent in stability when the adhesive composition is heated.
- the protective group represented by X is not particularly limited as long as it can be removed by reacting with moisture, and examples thereof include a trialkoxysilyl group and a group containing an aryl group.
- the trialkoxysilyl group may be a trimethoxysilyl group or a triethoxysilyl group.
- the group containing an aryl group may be a phenyl group or a benzyl group.
- N is preferably 1 to 7, more preferably 1 to 5, and further preferably 2 to 4.
- Examples of commercially available functional group-protected silane coupling agents include “X12-1056ES” (trade name) manufactured by Shin-Etsu Chemical Co., Ltd.
- the content of the functional group-protected silane coupling agent may be 0.4 to 5 parts by mass based on 100 parts by mass of the total amount of the urethane prepolymer.
- the content of the functional group-protecting silane coupling agent is preferably 0.5 parts by mass or more, more preferably 0.6 parts by mass or more, still more preferably 0.8, based on 100 parts by mass of the total amount of the urethane prepolymer. It is at least 4 parts by mass, preferably at most 4 parts by mass, more preferably at most 3.5 parts by mass, and even more preferably at most 3 parts by mass.
- the adhesive strength of the adhesive composition tends to be more excellent.
- the content of the functional group-protecting silane coupling agent is 5 parts by mass or less with respect to 100 parts by mass of the total amount of the urethane prepolymer, the elastic modulus of the cured product of the adhesive composition becomes too high and the impact resistance becomes high. It tends to be able to suppress the decrease.
- the content of the functional group-protected silane coupling agent may be 0.3 to 7 parts by mass with respect to 100 parts by mass of the total amount of the polyol constituting the urethane prepolymer.
- the content of the functional group-protecting silane coupling agent is preferably 0.5 parts by mass or more, more preferably 0.7 parts by mass or more, and further preferably 100 parts by mass with respect to the total amount of polyols constituting the urethane prepolymer. Is 1 part by mass or more, particularly preferably 1.5 parts by mass or more, preferably 6.5 parts by mass or less, more preferably 6 parts by mass or less, further preferably 5 parts by mass or less, particularly preferably 4 parts by mass or less. Is.
- the adhesive strength of the adhesive composition tends to be more excellent.
- the content of the functional group-protecting silane coupling agent is 7 parts by mass or less based on 100 parts by mass of the total amount of polyols constituting the urethane prepolymer, the elastic modulus of the cured product of the adhesive composition becomes too high. It tends to be possible to suppress a decrease in impact resistance.
- the adhesive composition of the present embodiment may contain a silane coupling agent other than the functional group-protecting silane coupling agent.
- silane coupling agents are not particularly limited, and silane coupling agents used in the field of adhesives can be used.
- examples of other silane coupling agents include compounds represented by the following general formula (2).
- Formula (2) in R 1, E, and n are the general formula (1) of R 1, E, and synonymous with n.
- the content of the other silane coupling agent may be 0 to 1 part by mass based on 100 parts by mass of the total amount of the urethane prepolymer.
- the adhesive composition of the present embodiment may further contain a catalyst from the viewpoint of accelerating the curing of the pretanned prepolymer and exhibiting higher adhesive strength.
- a catalyst from the viewpoint of accelerating the curing of the pretanned prepolymer and exhibiting higher adhesive strength.
- the catalyst include dibutyltin dilaurate, dibutylthione octate, dimethylcyclohexylamine, dimethylbenzylamine, trioctylamine and the like.
- the adhesive composition of the present embodiment 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.
- a thermoplastic polymer examples include polyurethane, ethylene-based copolymers, propylene-based copolymers, vinyl chloride-based copolymers, acrylic copolymers, styrene-conjugated diene block copolymers and the like.
- the adhesive composition of the present embodiment may further contain a tackifying resin from the viewpoint of imparting stronger adhesiveness to the formed adhesive layer.
- a tackifying resin for example, rosin resin, rosin ester resin, hydrogenated rosin ester resin, terpene resin, terpene phenol resin, hydrogenated terpene resin, petroleum resin, hydrogenated petroleum resin, coumarone resin, ketone resin, styrene resin, Examples thereof include modified styrene resin, xylene resin, epoxy resin and the like.
- the adhesive composition of the present embodiment may contain an appropriate amount of an antioxidant, a pigment, an ultraviolet absorber, a surfactant, a flame retardant, a filler, etc., if necessary.
- the isocyanate group which is the terminal group of the urethane prepolymer, reacts with moisture in the air or moisture on the surface of the adherend, and therefore, for example, the temperature is 23° C. and the humidity is 50% for 24 hours. It can be cured by curing, and a cured product of the adhesive composition can be obtained.
- the adhesive composition of the present embodiment comprises reacting a polyol and a polyisocyanate to include a polymer chain containing a structural unit derived from a polyol and a structural unit derived from a polyisocyanate, and an isocyanate group as an end group of the polymer chain. It can be produced by a method including a step of obtaining a urethane prepolymer and a step of mixing the obtained urethane prepolymer and a functional group-protected silane coupling agent.
- the adhesive composition of the present embodiment in the presence of a functional group-protected silane coupling agent, by reacting a polyol and a polyisocyanate, a polymer chain containing a structural unit derived from a polyol and a structural unit derived from a polyisocyanate It can also be produced by a method including a step of obtaining a urethane prepolymer having an isocyanate group as an end group of a polymer chain.
- the temperature and time for reacting the polyol and the polyisocyanate may be, for example, 85 to 120° C. and 1 minute to 48 hours.
- the temperature and time for mixing the urethane prepolymer and the functional group-protected silane coupling agent may be, for example, 85 to 120° C. and 1 minute to 48 hours. Note that degassing under reduced pressure may be performed in the mixing.
- the viscosity of the adhesive composition at 120° C. measured using a rotational viscometer is preferably 5 Pa ⁇ s or less, more preferably 4 Pa ⁇ s or less, and further preferably 3.5 Pa ⁇ s, from the viewpoint of improving coatability. s or less.
- the lower limit of the viscosity is not limited, but may be, for example, 1 Pa ⁇ s or more.
- the adhesive composition of the present embodiment can adhere various adherends via the cured product of the adhesive composition.
- the adherend include metal base materials such as SUS and aluminum, non-metal base materials such as polycarbonate, polyamide, polyetherimide, and glass.
- at least one of the adherends may be a polyamide base material, because the adherend can exhibit sufficient adhesive strength even when the adherend is a polyamide base material.
- the adhesive body of one embodiment is a reactive hot melt adhesive as described above, which adheres a first adherend, a second adherend, and a first adherend and a second adherend to each other. And a cured product of the composition.
- Examples of the adhesive body of the present embodiment include semiconductor devices, non-sewn clothing, electronic devices, and the like.
- the first adherend and the second adherend may be the same as those exemplified above for the adherend.
- the adhesive composition of the present embodiment can exhibit sufficient adhesive strength even when applied to a polyamide substrate. Therefore, either one or both of the first adherend and the second adherend may be a polyamide base material.
- the adhesive body of the present embodiment comprises a step of melting the above-mentioned reactive hot melt adhesive composition and applying it to the first adherend to form an adhesive layer, and a second cover on the adhesive layer. It may be manufactured by a method including a step of disposing an adherend and press-bonding a second adherend to obtain an adhesive body precursor, and a step of curing an adhesive layer in the obtained adhesive body precursor. it can.
- the temperature for melting the adhesive composition may be, for example, 80 to 180°C.
- the method of applying the adhesive composition to the first adherend is not particularly limited, and a known method can be appropriately applied.
- a method of crimping the second adherend for example, a method of crimping using a pressure roll or the like can be mentioned.
- the conditions for curing the adhesive layer in the adhesive body precursor may be the same as the conditions for curing the above-mentioned adhesive composition.
- A1 Crystalline polyester polyol containing adipic acid and ethylene glycol as main components (number of hydroxyl groups: 2, number average molecular weight: 5000)
- A2 Crystalline polyester polyol containing adipic acid and ethylene glycol as main components (number of hydroxyl groups: 2, number average molecular weight 2000)
- A3 Crystalline polyester polyol containing sebacic acid and 1,6-hexanediol as main components (number of hydroxyl groups: 2, number average molecular weight 5000)
- A4 Amorphous polyester polyol containing isophthalic acid and neopentyl glycol as main components (number of hydroxyl groups: 2, number average molecular weight: 2000)
- A5 Polypropylene glycol (polyether polyol, number of hydroxyl groups: 2, number average molecular weight: 2000)
- the adhesive composition is melted at 100° C., and in a temperature of 23° C. and a humidity of 50%, on a polycarbonate (PC) substrate of 25 mm in length ⁇ 75 mm in width ⁇ 2 mm in thickness, 1 mm in length ⁇ 25 mm in width ⁇ thickness
- PC polycarbonate
- a shear test (tensile speed: 10 mm/min) is performed to measure the adhesive strength (MPa). did. The same test was performed on the polyamide (PA) substrate to measure the adhesive strength (MPa).
- melt viscosity A melt viscosity of the adhesive composition (sample amount: 15 g) at a rotor rotation speed of 50 rpm and a temperature of 120° C. was measured with a TVB-25H type viscometer (manufactured by Toki Sangyo Co., Ltd.) using a No. 4 rotor.
- the adhesive compositions of Examples 1 to 5 containing the functional group-protected silane coupling agent were compared to the adhesive compositions containing no functional group-protected silane coupling agent when applied to a polyamide substrate. Even if there was, sufficient adhesive strength was exhibited.
- the adhesive compositions of Examples 1 to 5 had a low rate of increase in viscosity when heated at 110° C. and were excellent in mechanical properties after curing. From the above, it was confirmed that the adhesive composition of the present invention exhibits sufficient adhesive strength even when applied to a polyamide substrate.
Abstract
Description
一実施形態の反応性ホットメルト接着剤組成物(以下、単に「接着剤組成物」という場合もある。)は、ウレタンプレポリマーと、官能基保護型シランカップリング剤とを含有する。なお、一般的に、反応性ホットメルト接着剤組成物とは、湿気硬化型であり、空気中の水分又は被着体表面の水分と反応することによって、主にウレタンプレポリマーが高分子量化し、接着強度等を発現し得るものである。
カラム:「Gelpack GLA130-S」、「Gelpack GLA150-S」及び「Gelpack GLA160-S」(日立化成株式会社製、HPLC用充填カラム)
溶離液:テトラヒドロフラン
流量:1.0mL/分
カラム温度:40℃
検出器:RI
一実施形態の接着体は、第1の被着体と、第2の被着体と、第1の被着体及び第2の被着体を互いに接着する、上述の反応性ホットメルト接着剤組成物の硬化物とを備える。本実施形態の接着体としては、例えば、半導体装置、無縫製衣類、電子機器等が挙げられる。
<接着剤組成物の調製>
あらかじめ脱水処理したポリオール(A)を表1に示す配合量で反応容器に加え、均一に混合した。次いで、ポリイソシアネート(B)を表1に示す配合量で反応容器にさらに加えて均一に混合し、110℃で1時間反応させた。得られた混合物に官能基保護型シランカップリング剤(C)を表1に示す配合量で加えて均一に混合した後、さらに110℃で1時間減圧脱泡撹拌することによって、実施例1~4及び比較例1、2の接着剤組成物を得た。なお、表1における配合量の単位は、質量部である。
A1:アジピン酸及びエチレングリコールを主成分とする結晶性ポリエステルポリオール(水酸基数:2、数平均分子量:5000)
A2:アジピン酸及びエチレングリコールを主成分とする結晶性ポリエステルポリオール(水酸基数:2、数平均分子量2000)
A3:セバシン酸及び1,6-ヘキサンジオールを主成分とする結晶性ポリエステルポリオール(水酸基数:2、数平均分子量5000)
A4:イソフタル酸及びネオペンチルグリコールを主成分とする非晶性ポリエステルポリオール(水酸基数:2、数平均分子量:2000)
A5:ポリプロピレングリコール(ポリエーテルポリオール、水酸基数:2、数平均分子量:2000)
B1:ジフェニルメタンジイソシアネート(イソシアネート基数:2)
C1:トリエトキシシリルチオプロピルトリメトキシシラン(R1がメトキシ基、Eが硫黄原子、Xがトリエトキシシリル基、nが3である一般式(1)で表される化合物、商品名:「X12-1056ES」、信越化学株式会社製)
C’1:γ-メルカプト-プロピルトリメトキシシラン(商品名:「SILQUEST A-189 SILANE」、モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製)
接着剤組成物を100℃で溶融させ、温度23℃、湿度50%の環境下で、縦25mm×横75mm×厚さ2mmのポリカーボネート(PC)基材上に、縦1mm×横25mm×厚さ100μmの接着剤層を形成した後、接着剤層の上に、縦25mm×横75mm×厚さ2mmのPC基材を圧着して試験片を作製した。試験片を温度23℃、湿度50%の環境下で1日間静置して接着剤組成物を硬化せた後、せん断試験(引張速度:10mm/分)を行い、接着強度(MPa)を測定した。ポリアミド(PA)基材についても、同様の試験を行い、接着強度(MPa)を測定した。
TVB-25H形粘度計(東機産業株式会社製)で、4号ローターを使用して、ローター回転数50rpm、120℃における接着剤組成物(試料量:15g)の溶融粘度を測定した。
接着剤組成物を窒素雰囲気下、110℃で24時間静置後、粘度測定を実施し、粘度上昇率(110℃で24時間後の120℃における粘度/初期の120℃における粘度)を算出した。
接着剤組成物を100℃で溶融させ、厚さ100μmのフィルムを形成した後、当該フィルムを、温度23℃、湿度50%の恒温恒湿槽に2日間静置して、硬化させた。静置した後のフィルムを1号ダンベルで打ち抜いて試験片を作製し、オートグラフAGS-X(株式会社島津製作所製)を用いて、試験片の引張弾性率(MPa)、破断強度(MPa)、及び破断伸び(%)をJIS K-6251に準拠して測定した。
Claims (4)
- ポリオールに由来する構造単位及びポリイソシアネートに由来する構造単位を含む重合鎖を含み、前記重合鎖の末端基としてイソシアネート基を有する、ウレタンプレポリマーと、
官能基保護型シランカップリング剤と、
を含有する、反応性ホットメルト接着剤組成物。 - 前記官能基保護型シランカップリング剤の含有量が、前記ウレタンプレポリマーの総量100質量部に対して0.4~5質量部である、請求項1に記載の反応性ホットメルト接着剤組成物。
- 第1の被着体と、
第2の被着体と、
前記第1の被着体及び前記第2の被着体を互いに接着する、請求項1又は2に記載の反応性ホットメルト接着剤組成物の硬化物と、
を備える、接着体。 - 請求項1又は2に記載の反応性ホットメルト接着剤組成物を溶融させ、第1の被着体に塗布して接着剤層を形成する工程と、
前記接着剤層上に第2の被着体を配置し、前記第2の被着体を圧着することによって接着体前駆体を得る工程と、
得られた前記接着体前駆体における前記接着剤層を硬化させる工程と、
を備える、接着体の製造方法。
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US17/430,237 US20220112405A1 (en) | 2019-02-14 | 2020-02-03 | Reactive hot-melt adhesive composition, and bonded body and method for producing same |
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