WO2020004598A1 - Adhésif thermofusible contenant une composition de résine de propylène spécifique - Google Patents

Adhésif thermofusible contenant une composition de résine de propylène spécifique Download PDF

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Publication number
WO2020004598A1
WO2020004598A1 PCT/JP2019/025745 JP2019025745W WO2020004598A1 WO 2020004598 A1 WO2020004598 A1 WO 2020004598A1 JP 2019025745 W JP2019025745 W JP 2019025745W WO 2020004598 A1 WO2020004598 A1 WO 2020004598A1
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WIPO (PCT)
Prior art keywords
melt adhesive
hot melt
nucleating agent
polypropylene resin
adhesive according
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PCT/JP2019/025745
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English (en)
Japanese (ja)
Inventor
望 藤井
金丸　正実
麻未 古賀
武治 田島
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出光興産株式会社
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Publication of WO2020004598A1 publication Critical patent/WO2020004598A1/fr

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    • 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
    • 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
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/10—Homopolymers or copolymers of propene
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/10—Homopolymers or copolymers of propene
    • C09J123/12—Polypropene

Definitions

  • the present invention relates to a hot melt adhesive, and more particularly, to a hot melt adhesive containing a specific propylene-based resin composition.
  • Hot melt adhesives are solventless adhesives, which are applied to an adherend by heating and melting, then solidify by cooling, and exhibit adhesiveness. BACKGROUND ART In recent years, hot melt adhesives have been widely used in various fields because they are excellent in high-speed coating properties, quick-curing properties, solvent-free properties, barrier properties, energy saving properties, economy, and the like.
  • polypropylene polymers are widely used as base polymers for hot melt adhesives from the viewpoint of thermal stability.
  • low molecular weight polypropylene polymerized by metallocene catalyst has high fluidity, excellent coatability when used as a hot melt adhesive, excellent adhesive strength of low polar substances such as polypropylene, and heat stability during heat melting. Because of its excellent properties, it can be suitably used as a base polymer for various hot melt adhesives (Patent Documents 1 to 3).
  • the hot melt adhesive using this has a relatively slow solidification time, has good adherence to the adherend, and has good adhesion.
  • the adhesive because it is hard to solidify, for example, when laminating and bonding a porous substrate such as a nonwoven fabric, the adhesive exudes from the adhesive application surface side to the opposite surface, so-called back side A phenomenon called omission is likely to occur.
  • an object of the present invention is to provide a hot melt adhesive having an excellent solidification rate.
  • the present disclosure relates to the following. ⁇ 1> Using a differential scanning calorimeter (DSC), a sample is held at ⁇ 10 ° C. for 5 minutes in a nitrogen atmosphere, and then heated at a rate of 10 ° C./min.
  • DSC differential scanning calorimeter
  • a hot melt adhesive comprising a polypropylene resin (A) having a calorific value ( ⁇ HD) of more than 0 J / g and 80 J / g or less and a nucleating agent (B), wherein the content of the nucleating agent (B) Is from 5 mass ppm to 50,000 mass ppm with respect to 100 parts by mass of the polypropylene resin (A).
  • ⁇ HD calorific value
  • B nucleating agent
  • the melting point (Tm-D) defined as the observed peak top is not observed or is 0 ° C or more and 120 ° C or less.
  • Tm-D The hot melt adhesive according to ⁇ 1> or ⁇ 2>, wherein the polypropylene resin (A) has a weight average molecular weight (Mw) of 5,000 to 300,000.
  • Mw weight average molecular weight
  • ⁇ 4> The hot melt adhesive according to any one of the above ⁇ 1> to ⁇ 3>, wherein a half-crystallization time of the polypropylene resin (A) at 25 ° C. is 3 minutes or more.
  • ⁇ 5> The hot melt adhesive according to any one of ⁇ 1> to ⁇ 4> above, wherein the polypropylene resin (A) is a propylene homopolymer.
  • the polypropylene-based resin (A) contains at least one structural unit selected from the group consisting of ethylene and ⁇ -olefins having 4 to 30 carbon atoms in an amount of more than 0 mol% and 20 mol% or less.
  • the hot melt adhesive according to any one of ⁇ 4> to ⁇ 4>.
  • the nucleating agent (B) is at least one selected from the group consisting of an acetal nucleating agent, an amide nucleating agent and an organic metal salt nucleating agent. The hot melt adhesive according to one.
  • nucleating agent (B) is at least one selected from the group consisting of a sorbitol-based nucleating agent and a nonitol-based nucleating agent. adhesive.
  • nucleating agent (B) is at least one selected from the group consisting of a carboxamide nucleating agent and a triamide nucleating agent. adhesive.
  • nucleating agent (B) is a metal phenylphosphonate-based nucleating agent.
  • ⁇ 11> The hot melt adhesive according to ⁇ 10>, wherein there is substantially no visible white spot-like aggregation caused by the nucleating agent.
  • ⁇ 12> The hot melt adhesive according to any one of ⁇ 1> to ⁇ 11>, further including a tackifier (D).
  • ⁇ 13> The hot melt adhesive according to any one of ⁇ 1> to ⁇ 12>, further including an oil (E).
  • E oil
  • ⁇ 14> The hot melt adhesive according to any one of ⁇ 1> to ⁇ 13>, further including a linear hydrocarbon wax (F).
  • ⁇ 15> The hot melt adhesive according to any one of ⁇ 1> to ⁇ 14>, further comprising an ethylene polymer (G).
  • the hot melt adhesive of the present invention has an excellent solidification rate.
  • the term “A to B” regarding the description of numerical values means “A or more and B or less” (when A ⁇ B) or “A or less B or more” (when A> B). .
  • a combination of preferred embodiments is a more preferred embodiment.
  • melting endotherm ⁇ H-D
  • melting point Tm-D
  • weight average molecular weight Mw
  • Mn molecular weight distribution
  • the hot melt adhesive of this embodiment is a hot melt adhesive containing a polypropylene resin (A) having a melting endotherm ( ⁇ HD) of more than 0 J / g and 80 J / g or less and a nucleating agent (B).
  • a hot melt adhesive wherein the content of the nucleating agent (B) is 5 mass ppm or more and 50,000 mass ppm or less based on 100 parts by mass of the polypropylene resin (A).
  • the polypropylene resin (A) is preferably contained as a base polymer of the hot melt adhesive.
  • the base polymer of the hot melt adhesive may further contain a specific ethylene polymer (G) in addition to the polypropylene resin (A).
  • the polypropylene resin (A) used in the present embodiment is obtained by holding a sample at ⁇ 10 ° C. for 5 minutes in a nitrogen atmosphere using a differential scanning calorimeter (DSC), and then heating the sample at 10 ° C./min.
  • This is a polypropylene resin having a melting endotherm ( ⁇ HD) obtained from the obtained melting endothermic curve of more than 0 J / g and 80 J / g or less. If the melting endotherm ( ⁇ H ⁇ D) exceeds 80 J / g, the interfacial adhesive strength may decrease.
  • the melting endotherm ( ⁇ H-D) is preferably 20 J / g or more, more preferably 25 J / g or more, further preferably 27 J / g or more, and still more preferably, from the viewpoint of the adhesive strength and flexibility of the hot melt adhesive. Is 30 J / g or more, and preferably 50 J / g or less, more preferably 45 J / g or less, and still more preferably 40 J / g or less.
  • the above-mentioned melting endotherm ( ⁇ H ⁇ D) is defined as the highest temperature of the melting endotherm curve obtained by the DSC measurement using a line connecting the low-temperature side point with no calorific value change and the high-temperature side point with no calorific value change as a baseline.
  • the melting endotherm ( ⁇ HD) can be controlled by appropriately adjusting the monomer concentration and the reaction pressure.
  • the DSC used for the measurement must have been calibrated in advance on the same day.
  • the calibration described here indicates a temperature calibration using indium (In) and lead (Pb) as a standard sample and a calorimetric calibration using In as a standard sample.
  • the extrapolation melting onset temperatures of In and Pb were ⁇ 0.3 ° C.
  • the polypropylene resin (A) preferably satisfies the following (1).
  • (1) Using a differential scanning calorimeter (DSC), the sample was kept at ⁇ 10 ° C. for 5 minutes in a nitrogen atmosphere, and then heated at a rate of 10 ° C./min.
  • the melting point (Tm-D) defined as the observed peak top is not observed or is 0 ° C or more and 120 ° C or less.
  • the melting point (Tm-D) of the polypropylene resin (A) is not observed or is 0 ° C or more and 120 ° C or less from the viewpoint of the adhesive strength of the hot melt adhesive.
  • a melting point is observed, from the same viewpoint, it is more preferably at least 30 ° C, still more preferably at least 45 ° C, still more preferably at least 60 ° C, particularly preferably at least 75 ° C, and more preferably
  • the temperature is 100 ° C. or lower, more preferably 90 ° C. or lower, even more preferably 85 ° C. or lower.
  • the melting point can be controlled by appropriately adjusting the monomer concentration and the reaction pressure.
  • the weight average molecular weight (Mw) of the polypropylene resin (A) is preferably 5,000 or more, more preferably 15,000 or more, and still more preferably 30,000 or more, from the viewpoint of adhesive strength. From the viewpoint of coatability, it is preferably 300,000 or less, more preferably 200,000 or less, and still more preferably 150,000 or less.
  • the weight average molecular weight (Mw) is a weight average molecular weight in terms of polystyrene measured by a gel permeation chromatography (GPC) method.
  • the molecular weight distribution (Mw / Mn) of the polypropylene resin (A) is preferably 3.0 or less, more preferably 2.8 or less, further preferably 2.6 or less, and still more preferably 2.5 or less, And it is 1.5 or more, More preferably, it is 1.6 or more, More preferably, it is 1.7 or more, More preferably, it is 1.8 or more.
  • the molecular weight distribution (Mw / Mn) is a value calculated from the weight average molecular weight Mw and the number average molecular weight Mn in terms of polystyrene measured by gel permeation chromatography (GPC).
  • the semi-crystallization time when the polypropylene resin (A) is rapidly cooled to 25 ° C. from the molten state is preferably 3 minutes or more from the viewpoint of adhesiveness or from the molten state by a differential scanning calorimeter (DSC). No crystallization peak measured in the process of cooling at ⁇ 10 ° C./min is observed. It is more preferably at least 10 minutes, even more preferably at least 15 minutes, particularly preferably at least 20 minutes.
  • the half-crystallization time of the polypropylene resin (A) was measured by using a differential scanning calorimeter (DSC) (manufactured by Perkin-Elmer Co., Ltd., trade name: “DSC-7”) at 10 ° C.
  • DSC differential scanning calorimeter
  • the temperature is raised to 220 ° C. at 320 ° C./min and held for 5 minutes, then cooled to 25 ° C. at 320 ° C./min, and held for 60 minutes to measure the time change of the calorific value during the isothermal crystallization process.
  • the integrated value of the calorific value from the start of isothermal crystallization to the completion of crystallization is 100%
  • the time from the start of isothermal crystallization until the integrated value of the calorific value becomes 50% is the isothermal half-crystallization. Is defined as the conversion time (t 1/2 ).
  • the polypropylene-based resin (A) is not particularly limited as long as the above-mentioned melting endotherm ( ⁇ HD) satisfies the above range.
  • ⁇ HD melting endotherm
  • the propylene polymer is preferably selected from the group consisting of: Among them, a propylene homopolymer and a propylene-ethylene random copolymer are more preferable, and a propylene homopolymer is more preferable.
  • the polypropylene resin (A) is a copolymer
  • it contains at least one structural unit selected from the group consisting of ethylene and ⁇ -olefins having 4 to 30 carbon atoms, in an amount of more than 0 mol% and not more than 20 mol%.
  • This is preferable from the viewpoint of suppressing the occurrence of bumps due to crosslinking and increasing the flexibility of the resin composition. From such a viewpoint, it is more preferably at least 0.5 mol%, further preferably at least 1.0 mol%, and more preferably at most 18.5 mol%, further preferably at most 15.0 mol%, It is even more preferably at most 10.0 mol%.
  • the structural unit of the olefin having 2 carbon atoms is preferably 0 mol%. It is more than 20 mol%, more preferably more than 0 mol% and 18 mol% or less, further preferably more than 0 mol% and 16 mol% or less, even more preferably more than 0 mol% and 14 mol% or less.
  • the content of ⁇ -olefins having 4 or more carbon atoms is preferably more than 0 mol% and 30 mol% or less, more preferably 0 mol% or less. It is more than 25 mol% and more preferably more than 0 mol% and 20 mol% or less.
  • a commercially available product can be used as the polypropylene resin (A). Specific examples include “S400”, “S410”, “S600”, and “S901” of “L-MODU” (registered trademark) (manufactured by Idemitsu Kosan Co., Ltd.).
  • Commercially available amorphous poly- ⁇ -olefins (APAO) include “Rextac” manufactured by LLC, “Vestoplast” manufactured by Evonik, “Eastflex”, “Aerafin” manufactured by Eastman, etc. Name).
  • propylene elastomers include “Tuffmer XM”, “Tuffmer PN”, and “Tuffmer SN” manufactured by Mitsui Chemicals, Inc .; “Prime TPO” manufactured by Prime Polymer Co., Ltd .; and Dow Chemical Co., Ltd. "Versify”; “Vistamaxx” and “Linxar” manufactured by ExxonMobil, “Licosene” manufactured by Clariant; "Adflex” manufactured by Bathell, and the like (all are trade names).
  • the polypropylene resin (A) can be obtained by polymerizing a monomer in the presence of a polymerization catalyst such as a Ziegler-Natta type catalyst or a metallocene catalyst.
  • a polymerization catalyst such as a Ziegler-Natta type catalyst or a metallocene catalyst.
  • the polypropylene resin (A) is preferably a polypropylene resin obtained with a metallocene catalyst.
  • the metallocene catalyst is a kind of homogeneous catalyst, and the resulting polymer is a uniform polymer having a narrow molecular weight distribution and a narrow composition distribution.
  • the content of the polypropylene resin (A) in the hot melt adhesive is preferably 1% by mass or more, more preferably 5% by mass or more, and still more preferably 10% by mass, based on 100% by mass of the resin component (base polymer). %, More preferably 15% by mass or more, particularly preferably 25% by mass.
  • the upper limit is not particularly limited, but may be 100% by mass, 90% by mass or less, 85% by mass or less, or 80% by mass or less.
  • the polypropylene resin (A) in the hot melt adhesive may be of one type or two or more types.
  • the hot melt adhesive of the present embodiment contains a nucleating agent (B). Since the polypropylene-based resin (A) has a low crystallization rate, a hot-melt adhesive using the same has a relatively slow solidification time, good adherence to an adherend, and excellent adhesion. On the other hand, since it is difficult to solidify, a phenomenon called so-called strike-through, in which the adhesive exudes from the adhesive-coated surface to the opposite surface, is likely to occur.
  • the hot melt adhesive of the present embodiment contains the nucleating agent (B), whereby the crystallization speed of the polypropylene resin (A) is improved, and the solidification speed is excellent. As a result, the strike-through of the adhesive during the application of the adhesive can be suppressed.
  • the nucleating agent (B) is preferably one that induces crystallization quickly without lowering the physical properties of the polypropylene resin (A) and raises the crystallization temperature required for crystallization to start.
  • Specific examples of the nucleating agent (B) include acetal-based nucleating agents such as sorbitol and nonitol; amide-based nucleating agents such as carboxamide, triamide, and bisamide; metal phosphate salts, metal carboxylate salts, and metal phenylphosphonate.
  • the nucleating agent (B) is at least one selected from the group consisting of acetal nucleating agents, amide nucleating agents, and organic metal salt nucleating agents. Is preferred. Further, these may be used in combination.
  • the nucleating agent (B) may be added as a master batch within a range that does not affect the properties of the polypropylene resin (A).
  • the effect of improving the crystallization rate of the above nucleating agent varies depending on the temperature conditions during kneading and the concentration to be added, it is desirable to optimize the conditions according to each nucleating agent.
  • the effect of improving the crystallization rate when kneaded at preferably 260 to 320 ° C., more preferably 280 to 300 ° C. Becomes larger.
  • “Irgclear XT386” manufactured by BASF is preferably 5 to 1,000 ppm by mass, more preferably 10 to 500 ppm by mass, and still more preferably 50 to 200 ppm by mass with respect to 100 parts by mass of the polypropylene resin (A). When added at a concentration of ppm by mass, the effect of improving the crystallization rate is increased. Furthermore, “Eco Promote C” manufactured by Nissan Chemical Industries, Ltd. or the like is preferably in a good dispersion state, whereby the effect of improving the crystallization rate is increased.
  • the acetal-based nucleating agent is preferably at least one selected from the group consisting of sorbitol-based nucleating agents and nonitol-based nucleating agents.
  • sorbitol derivatives for example, 1,3: 2,4-bis-O-benzylidene-D-glucitol-dibenzylidene sorbitol, 1,3: 2,4-bis-O- (4-methylbenzylidene) -D-sorbitol , 1,3: 2,4-bis-O- (3,4-dimethylbenzylidene) sorbitol, bis (4-propylbenzylidene) propylsorbitol, nonitol, 1,2,3-trideoxy-4,6: 5,7 -Bis-o-[(4-propylphenyl) methylene] and mixtures thereof.
  • the amide nucleating agent is preferably at least one selected from the group consisting of a carboxamide nucleating agent and a triamide nucleating agent, and a carboxamide nucleating agent is particularly preferred.
  • the amide nucleating agent include N, N'-dicyclohexyl-2,6-naphthalenedicarboxamide, 1,3,5-tris [2,2-dimethylpropyl-amino] benzene, N, N ', N "-tris [2-Methylcyclohexane-1-yl] -propane-1,2,3-triylcarboxamide, N, N′-ethylenebisstearic acid amide, etc.
  • amide-based nucleating agents include Shin-Nippon Rika ( “Nrgester NU-100” manufactured by BASF, “Irgclear @ XT386” manufactured by BASF, and “Likaclear PC1” manufactured by Nippon Rika Co., Ltd.
  • the organic metal salt nucleating agent is in the form of fine powder and is used by dispersing it in a resin.
  • the organic metal salt nucleating agent include a phosphoric acid ester metal salt, a carboxylic acid metal salt, and a phenylphosphonic acid metal salt.
  • phosphoric acid is preferred from the viewpoint of improving the crystallization rate of the polypropylene resin (A).
  • Ester metal salts and phenylphosphonic acid metal salt nucleating agents are preferred, and phenylphosphonic acid metal salt nucleating agents are particularly preferred.
  • organic metal salt-based nucleating agents include "ADKSTAB @ NA-11", “ADKSTAB @ NA-21” and “ADKSTAB @ NA-27” manufactured by ADEKA, “Hostanox 4030” manufactured by Clariant, and “Milken Chemical”. HPN-68L "Eco-promote C” manufactured by Nissan Chemical Industries, Ltd. and the like.
  • the content of the nucleating agent (B) in the hot melt adhesive is determined from the viewpoint of improving the crystallization speed of the polypropylene resin (A) without deteriorating the physical properties of the polypropylene resin (A).
  • A) It is at least 5 ppm by mass, preferably at least 10 ppm by mass, more preferably at least 50 ppm by mass with respect to 100 parts by mass, and 50,000 parts by mass from the viewpoint of dispersibility in the polypropylene resin (A).
  • ppm preferably 20,000 mass ppm or less, more preferably 5,000 mass ppm or less, still more preferably 1,000 mass ppm or less, further preferably 500 mass ppm or less, and still more preferably 200 mass ppm or less.
  • the hot melt adhesive of the present invention is preferably substantially free from visible white spot-like aggregation caused by the nucleating agent when visually observed.
  • the hot melt adhesive of the present embodiment may further contain a tackifier (D).
  • a tackifier (D) for example, a solid, semi-solid or liquid at room temperature composed of a hydrogenated derivative of an aliphatic hydrocarbon petroleum resin, a rosin derivative resin, a polyterpene resin, a petroleum resin, an oil-soluble phenol resin, or the like. And the like.
  • tackifiers Commercially available products of the tackifier (D) include the following.
  • Examples of the tackifiers produced using crude oil and the raw material obtained in the naphtha refining process include “I-MARV” (manufactured by Idemitsu Kosan Co., Ltd.), “ALCON” (manufactured by Arakawa Chemical Industry Co., Ltd.), “Quinton” ( Nippon Zeon Co., Ltd.), “T-REZ” (JXTG Energy Co., Ltd.), “Escorez”, “Opera” (all from ExxonMobil Chemical), “Eastotac", “Regalite”, “Regalrez”, “Plastolyn” (all from Eastman), “Sukolez” (Kolon), “Wingtack", “Norsolene” (all from Cray Valley) and the like can be mentioned (all are trade names).
  • Examples of the tackifier manufactured using an essential oil obtained from orange or the like as a raw material include “Clearon” (manufactured by Yashara Chemical Co., Ltd.) and “Sylvalite” and “Sylvares” (manufactured by Arizona Chemical). (All are trade names).
  • Examples of tackifiers manufactured using raw materials such as rosin include “Haritac”, “Neotol” (manufactured by Harima Chemicals, Inc.), “Ester Gum”, and “Pencel” (manufactured by Arakawa Chemical Industries, Ltd.). (Both are trade names).
  • the content of the tackifier (D) in the hot-melt adhesive is preferably based on 100 parts by mass of the resin component (base polymer) in the hot-melt adhesive from the viewpoint of improving tackiness and applicability. Is 20 parts by mass or more, more preferably 30 parts by mass or more, still more preferably 40 parts by mass or more, even more preferably 50 parts by mass or more, and preferably 200 parts by mass or less, more preferably 150 parts by mass or less, More preferably, it is 120 parts by mass or less, even more preferably 100 parts by mass or less.
  • the softening point of the tackifier (D) is not particularly limited. However, if the softening point is too high, the viscosity of the hot-melt adhesive at the time of coating increases, so that the coatability deteriorates and the softening point is too low. In addition, the thermal stability of the hot melt adhesive becomes poor, and seizure occurs in the melter, which adversely affects the adhesiveness and odor.
  • the softening point of the tackifier (D) is preferably 80 ° C. or higher, more preferably 85 ° C. or higher, even more preferably 90 ° C. or higher, and preferably 130 ° C. or lower, more preferably It is 120 ° C. or lower, more preferably 110 ° C. or lower.
  • the hot melt adhesive of the present embodiment may further contain an oil (E).
  • the oil (E) is not particularly limited, and mineral oils such as paraffin-based process oil, naphthene-based process oil and isoparaffin-based oil, aromatic mineral oil-based hydrocarbons, polybutene, polyisobutylene, polybutadiene, and poly ( ⁇ ) -Olefin) and other synthetic resin-based hydrocarbons such as low molecular weight products, alkylbenzenes, castor oil, linseed oil, rapeseed oil, fatty oil-based softeners such as coconut oil, dibutyl phthalate, dioctyl phthalate, dioctyl adipate, dioctyl sebacate, etc.
  • Ester plasticizers and the like are preferred, and at least one selected from the group consisting of mineral oil-based hydrocarbons, paraffin-based process oils, and naphthene-based process oils is preferred, and paraffin-based hydrocarbons have a carbon number of 50% of the total carbon number. Oil is particularly preferred.
  • the weight average molecular weight of the mineral oil-based hydrocarbon is preferably from 50 to 2,000, particularly preferably from 100 to 1,500, and the pour point is preferably from -40 to 0 ° C, particularly preferably from -30 to 0 ° C.
  • the (COC method) is preferably at 200 to 400 ° C., particularly 250 to 350 ° C.
  • the pour point is a value measured according to JIS K2269, and the flash point is a value measured according to JIS K2265.
  • the kinematic viscosity of the oil (E) at 40 ° C. is preferably 5 cSt or more and 800 cSt or less, more preferably 10 cSt or more and 500 cSt or less.
  • the kinematic viscosity is a value measured according to ISO3104.
  • paraffin-based process oils include “Diana Process Oil PW-32”, “Diana Process Oil PW-90”, “Diana Process Oil PW-150”, and “Diana Process Oil PS-” manufactured by Idemitsu Kosan Co., Ltd. 32, “Diana Process Oil PS-90", “Diana Process Oil PS-430”; “Kaydol Oil” and “ParaLux Oil” manufactured by Chevron USA (all are trade names).
  • IP Solvent 1016 Commercially available isoparaffinic oils include “IP Solvent 1016”, “IP Solvent 1620”, “IP Solvent 2028”, “IP Solvent 2835”, “IP Clean LX” manufactured by Idemitsu Kosan Co., Ltd .; And “NA Solvent” series (both are trade names).
  • the hot melt adhesive of the present embodiment contains an oil (E)
  • the content is determined from the viewpoint of improving the tackiness of the hot melt adhesive, applicability, and improving the wettability to an adherend due to a decrease in viscosity.
  • the resin component (base polymer) in the hot melt adhesive preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and preferably 200 parts by mass or less. It is preferably at most 100 parts by mass, more preferably at most 50 parts by mass.
  • the hot melt adhesive of the present embodiment may further contain a linear hydrocarbon wax (F) having a melting endotherm ( ⁇ HD) of more than 120 J / g and 300 J / g or less.
  • the melting endotherm ( ⁇ HD) of the linear hydrocarbon wax (F) is more preferably 140 J / g or more, still more preferably 160 J / g or more, and more preferably 280 J, from the viewpoint of solidification rate. / G or less, more preferably 250 J / g or less.
  • the melting endotherm ( ⁇ HD) of the linear hydrocarbon wax (F) is measured in the same manner as the above-mentioned melting endotherm ( ⁇ HD) of the polypropylene resin (A).
  • the melting point (Tm-D) of the linear hydrocarbon wax (F) is preferably at least 50 ° C, more preferably at least 80 ° C, and preferably at most 150 ° C, more preferably at most 130 ° C.
  • the melting point (Tm-D) of the linear hydrocarbon wax (F) is measured in the same manner as the above-mentioned melting point (Tm-D) of the polypropylene resin (A).
  • straight-chain hydrocarbon wax examples include paraffin wax, higher fatty acid wax, higher fatty acid ester wax, Fischer-Tropsch wax, polyethylene wax, polypropylene wax and the like (however, the ethylene polymer (G) described below). Excludes that apply.)
  • linear hydrocarbon wax (F) Commercial products of the linear hydrocarbon wax (F) include the following.
  • examples of the Fischer-Tropsch wax include “Sasol” manufactured by Sasol, and examples of the paraffin wax include “Paraffin Wax” manufactured by Nippon Seiro Co., Ltd.
  • examples of the low-density polyethylene-based wax include “Hi Wax” NL series manufactured by Mitsui Chemicals, Inc. and the like are listed (all are trade names).
  • the content of the linear hydrocarbon-based wax (F) in the hot melt adhesive of the present embodiment is 100% in terms of the content of the resin component (base polymer) in the hot melt adhesive from the viewpoint of improving flexibility and coating properties.
  • the amount is preferably 10,000 parts by mass or less, more preferably 5,000 parts by mass or less, still more preferably 500 parts by mass or less, and still more preferably 100 parts by mass or less with respect to parts by mass.
  • the content of the wax increases, the viscosity of the thermoplastic resin composition decreases. Therefore, it is preferable to appropriately determine the content of the linear hydrocarbon wax (F) according to the use of the hot melt adhesive made of the thermoplastic resin composition.
  • the hot melt adhesive of the present embodiment may contain an ethylene polymer (G) having a melting endotherm ( ⁇ HD) of 0 J / g or more and 120 J / g or less.
  • the ethylene polymer (G) is preferably contained as a base polymer of the hot melt adhesive.
  • the melting endothermic amount ( ⁇ HD) of the ethylene polymer (G) is preferably 20 J / g or more, more preferably 40 J / g or more, and preferably 100 J / g or less, from the viewpoint of flexibility. More preferably, it is 80 J / g or less.
  • the melting endotherm ( ⁇ HD) of the ethylene polymer (G) is measured in the same manner as the above-mentioned melting endotherm ( ⁇ HD) of the polypropylene resin (A).
  • the melting point (Tm-D) of the ethylene polymer (G) is preferably 30 ° C. or higher, more preferably 50 ° C. or higher, and preferably less than 85 ° C., more preferably, from the viewpoint of applicability. 80 ° C. or less.
  • the melting point (Tm-D) of the ethylene-based polymer (G) is measured in the same manner as the melting point (Tm-D) of the polypropylene-based resin (A).
  • Ethylene polymer (G) is an ethylene homopolymer or an ethylene copolymer.
  • the ethylene-based copolymer refers to a copolymer of ethylene and a copolymerizable monomer copolymerizable with ethylene.
  • the copolymerizable monomer include ⁇ -olefins; carboxylic acids (esters) such as vinyl acetate, (meth) acrylic acid, (meth) acrylate, maleic acid, and maleic ester; maleic anhydride, phthalic anhydride, and anhydride.
  • Carboxylic acid anhydrides such as succinic acid; and the like.
  • copolymerizable monomers may be copolymerized with ethylene alone, or two or more copolymerizable monomers may be copolymerized.
  • ethylene copolymer examples include an ethylene / ⁇ -olefin copolymer, an ethylene / carboxylic acid copolymer, an ethylene / carboxylic acid ester copolymer, and an ethylene / carboxylic anhydride copolymer.
  • (meth) acrylic acid refers to a concept including both methacrylic acid and acrylic acid.
  • Specific examples of (meth) acrylates include methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, acryl Isooctyl acid, methyl methacrylate, ethyl methacrylate, glycidyl methacrylate and the like can be mentioned.
  • the ethylene polymer (G) at least one selected from the group consisting of ⁇ -olefins having 3 to 30 carbon atoms (preferably having 3 to 10 carbon atoms) from the viewpoint of the adhesiveness and odor of the hot melt adhesive. It is preferable to contain more than 0 mol% and no more than 40 mol% of structural units.
  • the ethylene-based polymer (G) is preferably an ethylene / ⁇ -olefin copolymer, and is preferably a copolymer of ethylene and an ⁇ -olefin having 3 to 30 (preferably 3 to 10) carbon atoms. preferable. Further, an ethylene / ⁇ -olefin copolymer obtained by polymerization with a metallocene catalyst is preferable.
  • ⁇ -olefin examples include propylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, and 1-hexadecene , 1-octadecene, 1-eicosene and the like. In the present embodiment, one or more of these can be used. Propylene or 1-octene is preferred among these ⁇ -olefins.
  • the ethylene-based polymer (G) used in the present embodiment is more preferably an ethylene-1-octene copolymer from the viewpoint of adhesiveness, and still more preferably contains 5 to 20 structural units derived from 1-octene. It is an ethylene-1-octene copolymer containing mol%.
  • the hot melt adhesive of the present embodiment contains an ethylene / ⁇ -olefin copolymer obtained by polymerization with a metallocene catalyst, the suitability for spiral coating at low temperatures is improved, and the adhesion to a polyethylene film or a nonwoven fabric is further improved. Excellent.
  • G Commercial products of the ethylene-based polymer (G) include the “Exact” series (manufactured by ExxonMobil), the “Affinity @ polymer” series, and the “Infuse” series (both manufactured by Dow Chemical Company). "Affinity @ GA1875", “Affinity @ GA1900”, “Affinity @ GA1950”, “Affinity @ GP1570”, “Infuse @ 9807”, “Infuse9817” (manufactured by Dow Chemical Company) (all are trade names).
  • the content of the ethylene-based polymer (G) in the hot melt adhesive is preferably 10,000 parts by mass based on 100 parts by mass of the polypropylene-based resin (A) from the viewpoint of improving flexibility and coatability. Or less, more preferably 7,500 parts by mass or less, and still more preferably 5,000 parts by mass or less.
  • the content of the ethylene polymer (G) in the resin component (base polymer) increases, the strength decreases. Therefore, it is preferable to appropriately determine the content of the ethylene polymer (G) according to the use of the hot melt adhesive.
  • the content of the polypropylene resin (A) in the total amount of 100% by mass of the polypropylene resin (A) and the ethylene polymer (G) is preferably 25% by mass or more, more preferably 50% by mass or more, and furthermore It is preferably at least 75% by mass.
  • the hot melt adhesive of the present embodiment may further contain various additives such as a plasticizer, an inorganic filler, an antioxidant and the like, as needed, as long as the effects of the present invention are not impaired.
  • plasticizer examples include phthalates, adipic esters, fatty acid esters, glycols, epoxy polymer plasticizers, and the like.
  • inorganic filler talc, calcium carbonate, barium carbonate, wollastonite, silica, clay, mica, kaolin, titanium oxide, diatomaceous earth, urea resin, styrene beads, starch, barium sulfate, calcium sulfate, magnesium silicate, Examples thereof include magnesium carbonate, alumina, and quartz powder.
  • antioxidants examples include trisnonylphenyl phosphite, distearylpentaerythritol diphosphite, "Adecastab 1178" (manufactured by ADEKA Corporation), “Stamlyzer TNP” (manufactured by Sumitomo Chemical Co., Ltd.), and “Ilgafos 168" (BASF Phosphorus antioxidants such as “Sandstab P-EPQ” (manufactured by Sando), 2,6-di-t-butyl-4-methylphenol, n-octadecyl-3- (3 ′, 5 ′) Phenolic antioxidants such as -di-t-butyl-4'-hydroxyphenyl) propionate, “SUMILIZER BHT” (manufactured by Sumitomo Chemical Co., Ltd.) and “Irganox 1010" (manufactured by BASF), dilauryl-3,3 '
  • the hot melt adhesive of the present embodiment may further contain a wax other than the linear hydrocarbon wax (F).
  • the wax other than the linear hydrocarbon wax (F) include animal wax, vegetable wax, carnauba wax, candelilla wax, wood wax, beeswax, mineral wax, petroleum wax, microcrystalline wax, petrolatum, higher fatty acid wax, and higher-grade wax. Fatty acid ester waxes and the like.
  • the hot melt adhesive of the present embodiment it is possible to partially crosslink by adding a crosslinking agent or a crosslinking assistant.
  • the crosslinking agent include organic peroxides, sulfur, sulfur compounds, and phenolic vulcanizing agents such as phenolic resins. Of these, organic peroxides are preferred. Specific examples of the organic peroxide include 2,5-dimethyl-2,5-di (t-butylperoxy) -hexane and 2,5-dimethyl-2,5-di (t-butylperoxy) -3.
  • 2,5-dimethyl-2,5-di- (t-butylperoxy) hexane and 2,5-dimethyl-2,5-di- (t -Butylperoxy) -3-hexyne 1,3-bis (t-butylperoxyisopropyl) benzene, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, n-butyl -4,4-bis (t-butylperoxy) valerate is preferred, and 1,3-bis (t-butylperoxyisopropyl) benzene is most preferred.
  • crosslinking assistant examples include N-methyl-N, 4-dinitrosoaniline, nitrosobenzene, diphenylguanidine, divinylbenzene, trimethylolpropane tri (meth) acrylate, ethylene di (meth) acrylate, and diethylene glycol di (meth) acrylate.
  • crosslinking aids triallyl cyanurate, ethylene glycol dimethacrylate, divinylbenzene, and bismaleimide are preferable. These are easy to handle, have good compatibility with the polypropylene resin (A), which is the main component of the object to be crosslinked, and have an action of solubilizing organic peroxides. Since it acts as an oxide dispersant, a resin composition having a uniform crosslinking effect by heat treatment and a balance between flexibility and physical properties can be obtained.
  • the cross-linking agent and the cross-linking assistant may be used alone or in combination of two or more.
  • a crosslinking agent and a crosslinking aid are used, the degree of crosslinking is adjusted arbitrarily in the range of 0.1 to 5 parts by mass based on 100 parts by mass of the total of components (A) to (G). be able to.
  • an unsaturated silane compound is used as a crosslinking aid, crosslinking can be further advanced by contact with moisture in the presence of a silanol condensation catalyst.
  • the hot melt adhesive of this embodiment is obtained by adding a nucleating agent (B) to a polypropylene resin (A), and further, if necessary, a tackifier (D), an oil (E), and a linear hydrocarbon-based resin.
  • a nucleating agent (B) to a polypropylene resin (A)
  • a tackifier (D) to an oil (E)
  • a linear hydrocarbon-based resin At least one selected from the group consisting of wax (F), ethylene-based polymer (G) and various additives is added and dry-blended using a Henschel mixer or the like, and a single-screw or twin-screw extruder, plast mill or Banbury is used. It can be produced by melt-kneading with a mixer or the like.
  • the temperature during melt-kneading can be appropriately determined according to the type of the nucleating agent (B) used.
  • the temperature during melt kneading is preferably 150 ° C. Or less, more preferably 100 ° C. or less.
  • the temperature at the time of melt-kneading is preferably 250 ° C. or higher, since the effect of improving the crystallization rate when kneaded and dispersed at a high temperature in a hot melt adhesive is large. 280 ° C. or more.
  • the hot melt adhesive of the present embodiment has an excellent solidification rate.
  • a hot melt adhesive having an improved solidification rate is useful in various applications.
  • the hot melt adhesive composed of the thermoplastic resin composition of the present embodiment can be suitably used for, for example, sanitary materials, bookbinding, fibers, cans, filters, low pressure molding, and bag making. .
  • the packaging field fixing cartons, cardboard, cushioning materials, repairing automatic packaging boxes, fixing samples, packaging after unpacking, packing desiccants in food packaging, etc.
  • electrical materials Fixing electronic parts on C-board, temporary fixing, anti-vibration reinforcement, filling of connector empty space, board insulation, wire fixing, encapsulation), film adhesive processing, non-slip (film coating such as DM), housing, building materials ( Siding, tile, flooring, carpet, fabric, wallpaper, sample adhesion), architecture / interior (adhesion of insulation material, kitchen tarpaulin, prevention of fraying when cutting tatami, roof, veranda FRP, crack, tile), furniture, woodwork (Tables, chairs, sofas, beds, mirror cabinets, fixing of reinforcements, bonding of fabric, fixing of frills, Buddhist altars, binding, etc.), hobby, small Adhesives, accessories, traditional crafts, automotive industry (adhesion of dashboard anti-vibration reinforcement, adhesion of head / lamp case, door interior materials
  • the hot-melt adhesive In the case of woodworking, in a bonding method in which a hot-melt adhesive is applied to an adherend and then wound once with a roll, if the hot-melt adhesive does not solidify quickly, the rolls are all bonded and integrated. Faster solidification allows for winding.
  • the bonding between the pocket coils is made on an automated automated assembly machine. After the pocket coils are adhered to each other, it is necessary to develop the adhesive strength early in order to prevent displacement, and it is useful to improve the solidification speed.
  • the hot melt adhesive may be applied and affixed using a hand gun. At this time, the set time is shortened, and thus the adhesive strength immediately after lamination is improved.
  • B1 "Gelall D”, a sorbitol-based nucleating agent manufactured by Shin Nippon Rika Co., Ltd.
  • B2 "Gerol MD”, a sorbitol-based nucleating agent manufactured by Shin Nippon Rika Co., Ltd.
  • B3 "Gerol DXR”, New Japan Sorbitol-based nucleating agent manufactured by Rika Co., Ltd.
  • E1 "Diana Process Oil PW-90": paraffinic oil, manufactured by Idemitsu Kosan Co., Ltd., kinematic viscosity at 40.degree.
  • G ⁇ Ethylene polymer (G)>
  • the heat was obtained as a crystallization heat ( ⁇ Hc) from a crystallization heat curve obtained.
  • the crystallization temperature (Tc) was determined from the peak top of the obtained crystallization exothermic curve.
  • the melting endotherm ( ⁇ H ⁇ D or ⁇ Hm) and the crystallization calorific value (cHc) are obtained by using a line connecting a low-temperature side point with no calorific value change and a high-temperature side point with no calorific value change as a baseline.
  • a line portion including a peak of a melting endothermic curve and a crystallization exothermic curve obtained by DSC measurement using a differential scanning calorimeter (manufactured by Perkin-Elmer Co., Ltd., “DSC-7”) is surrounded by the base line. It is calculated by calculating the area.
  • Weight average molecular weight (Mw) The weight average molecular weight (Mw) was measured by gel permeation chromatography (GPC). For the measurement, the following apparatus and conditions were used, and a weight average molecular weight in terms of polystyrene was obtained.
  • ⁇ GPC measurement device Column: "TOSO GMHHR-H (S) HT” manufactured by Tosoh Corporation Detector: RI detection for liquid chromatogram "WATERS 150C” manufactured by Waters Corporation ⁇ Measurement conditions> Solvent: 1,2,4-trichlorobenzene Measurement temperature: 145 ° C Flow rate: 1.0 mL / min Sample concentration: 2.2 mg / mL Injection volume: 160 ⁇ L Calibration curve: Universal Calibration Analysis program: HT-GPC (Ver. 1.0)
  • the measurement was carried out using a differential scanning calorimeter (DSC) (manufactured by Perkin-Elmer Co., Ltd., trade name: "DSC-7") by the following method.
  • DSC differential scanning calorimeter
  • 10 mg of a sample is held at 25 ° C. for 5 minutes, heated to 220 ° C. at 320 ° C./min and held for 5 minutes, then cooled to 25 ° C. at 320 ° C./min, and held for 60 minutes to be isothermal.
  • the time change of the calorific value during the crystallization process was measured.
  • Examples 1 to 22 and Comparative Example 1 The components of the types and compounding amounts shown in Tables 1 and 2 were melt-kneaded using a plast mill at the temperature shown in Tables 1 and 5 for 5 minutes at 100 rpm to prepare a resin composition.
  • the nucleating agent (B5) was kneaded at 300 ° C.
  • the nucleating agent (B10) was kneaded at 80 ° C.
  • Examples 23 to 27 and Comparative Examples 2 to 6 The components shown in Table 3 were charged into a heat-resistant glass bottle having a capacity of 100 mL so that the total amount was 60 g, and the content was melted by heating at 200 ° C. for 30 minutes. Thereafter, the contents were stirred with a spatula for 5 minutes and heated at 200 ° C. for 10 minutes. The above operation was repeated five times to obtain a hot melt adhesive made of the thermoplastic resin composition. After taking out the obtained hot melt adhesive into a vat coated with polytetrafluoroethylene, the solidification time was measured by the following method. In Example 27 and Comparative Example 6, the open time was measured by the following method. Table 3 shows the results.
  • the open time refers to the adhesive holding time from when the adhesive is applied to the adherend until the temperature decreases and the adhesive disappears.
  • a hot melt adhesive melted by heating to 180 ° C. is applied to a K liner cardboard at a coating amount of 2.8 to 3.2 g / m, and after a predetermined time, an adhesive pressure of 2 kg / 25 cm 2 and a set time of 2 seconds Under the following conditions.
  • the adhesive test piece was allowed to stand for 24 hours in an environment of 23 ° C. and 50% humidity, and was peeled off by hand. Of the five measurements, the longest elapsed time when four or more test pieces with a material destruction rate of 80% or more were defined as open time (seconds).

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

Abstract

La présente invention concerne un adhésif thermofusible qui contient (A) une résine de polypropylène qui a un endotherme de fusion (∆H - D) supérieure à 0 J/g mais inférieure ou égale à 80 J/g tel que déterminé à partir de la courbe endothermique de fusion qui est obtenue à l'aide d'un calorimètre à balayage différentiel (DSC) par maintien d'un échantillon à -10 °C pendant 5 minutes dans une atmosphère d'azote et par chauffage, ensuite, de l'échantillon à 10 °C/min, et (B) un agent de nucléation. Ledit adhésif thermofusible est conçu de telle sorte que la teneur de l'agent de nucléation (B) est comprise entre 5 ppm en masse et 50 000 ppm en masse (inclus) par rapport à 100 parties en masse de la résine de polypropylène (A).
PCT/JP2019/025745 2018-06-28 2019-06-27 Adhésif thermofusible contenant une composition de résine de propylène spécifique WO2020004598A1 (fr)

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JP2014501811A (ja) * 2010-11-19 2014-01-23 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン 接着剤組成物およびその使用
JP2016524002A (ja) * 2013-05-23 2016-08-12 ボスティック，インコーポレイテッド 低融点ポリプロピレンホモポリマーを基剤とするホットメルト接着剤
JP2017516888A (ja) * 2014-04-16 2017-06-22 ボスティック，インコーポレイテッド 改良された性質を有するポリオレフィンベースのホットメルト接着剤
JP2018504473A (ja) * 2014-12-04 2018-02-15 エクソンモービル ケミカル パテンツ インコーポレイテッド 多峰性ポリマーブレンド、それを含むホットメルト接着剤およびその使用

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JP2014501811A (ja) * 2010-11-19 2014-01-23 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン 接着剤組成物およびその使用
JP2016524002A (ja) * 2013-05-23 2016-08-12 ボスティック，インコーポレイテッド 低融点ポリプロピレンホモポリマーを基剤とするホットメルト接着剤
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JP2018504473A (ja) * 2014-12-04 2018-02-15 エクソンモービル ケミカル パテンツ インコーポレイテッド 多峰性ポリマーブレンド、それを含むホットメルト接着剤およびその使用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021536521A (ja) * 2018-09-03 2021-12-27 サソル サウス アフリカ リミティド ホットメルト接着剤組成物

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