WO2014136940A1 - Composition adhésive thermofusible - Google Patents

Composition adhésive thermofusible Download PDF

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Publication number
WO2014136940A1
WO2014136940A1 PCT/JP2014/055975 JP2014055975W WO2014136940A1 WO 2014136940 A1 WO2014136940 A1 WO 2014136940A1 JP 2014055975 W JP2014055975 W JP 2014055975W WO 2014136940 A1 WO2014136940 A1 WO 2014136940A1
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WO
WIPO (PCT)
Prior art keywords
styrene
group
block copolymer
adhesive composition
butadiene
Prior art date
Application number
PCT/JP2014/055975
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English (en)
Japanese (ja)
Inventor
隆裕 岡松
亮太 高橋
美昭 桐野
Original Assignee
横浜ゴム株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 横浜ゴム株式会社 filed Critical 横浜ゴム株式会社
Priority to KR1020157025286A priority Critical patent/KR101622324B1/ko
Priority to CN201480025871.7A priority patent/CN105209566B/zh
Publication of WO2014136940A1 publication Critical patent/WO2014136940A1/fr
Priority to PH12015501989A priority patent/PH12015501989A1/en

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Classifications

    • 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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J153/02—Vinyl aromatic monomers and conjugated dienes

Definitions

  • the present invention relates to a hot melt adhesive composition.
  • One-component moisture-curing urethane-based hot melt adhesives based on urethane prepolymers with an isocyanate group in the molecule are applied to the adherend in a molten state, and are cooled, also called reactive hot melt adhesives. After solidifying, the reaction of the isocyanate group proceeds by the moisture present in the adherend or air to form a crosslinked structure and harden. Therefore, in the one-component moisture-curing urethane hot melt adhesive, higher heat resistance is expressed as compared to other hot melt adhesives due to the molecular growth reaction of the urethane prepolymer (see, for example, Patent Documents 1 and 2). .)
  • thermo stability the property stability in the molten state
  • a foreign substance in which a part of the component was gelled might be mixed.
  • the peel strength at 120 ° C. was low and the heat resistance was not sufficient depending on the kind of the adherend.
  • an object of the present invention is to provide a hot melt adhesive composition having excellent thermal stability and good heat resistance.
  • the present inventors have blended a specific amount of a nitrone derivative with a predetermined styrene-butadiene block copolymer, thereby providing excellent thermal stability and good heat resistance. It discovered that it became a hot-melt-adhesive composition, and completed this invention. That is, the present inventors have found that the above problem can be solved by the following configuration.
  • the styrene-butadiene block copolymer is a styrene-butadiene-styrene block copolymer (SBS) and / or a styrene-butadiene-butylene-styrene block copolymer (SBBS),
  • SBS styrene-butadiene-styrene block copolymer
  • SBBS styrene-butadiene-butylene-styrene block copolymer
  • the hot melt adhesive composition of the present invention contains a styrene-butadiene block copolymer and a nitrone derivative, and the styrene-butadiene block copolymer described above.
  • styrene-butadiene-styrene block copolymer SBS
  • SBBS styrene-butadiene-butylene-styrene block copolymer
  • the hot melt adhesive composition is 1 to 10 parts by mass with respect to 100 parts by mass.
  • a hot melt adhesive composition having excellent thermal stability and good heat resistance is obtained.
  • cyclization occurs between part or all of the nitrone derivative and the butadiene double bond of the styrene-butadiene block copolymer in the molten state at the time of kneading or use. It is considered that the interaction (intermolecular force) between the styrene-butadiene block copolymers is increased by the occurrence of the addition reaction (see the following formulas (I) and (II)).
  • a composition prepared without blending the nitrone derivative has a low melt viscosity at 120 ° C., as shown in Comparative Examples described later.
  • the nitrone derivative and the styrene-butadiene block copolymer are kneaded at a temperature (for example, about 160 to 180 ° C.) assuming a molten state at the time of use, and then the resulting mixture is mixed with cyclohexane, ethyl acetate, or the like.
  • the styrene-butadiene block copolymer contained in the adhesive composition of the present invention is a styrene-butadiene-styrene block copolymer (SBS) and / or a styrene-butadiene-butylene-styrene block copolymer (SBBS). is there.
  • SBS styrene-butadiene-styrene block copolymer
  • SBBS styrene-butadiene-butylene-styrene block copolymer
  • the styrene content of the styrene-butadiene block copolymer is not particularly limited, but for SBS, the mass ratio of styrene to butadiene (styrene / butadiene) is preferably 20/80 to 50/50. More preferably, the amount is 30/70 to 45/55.
  • the melt flow rate (MFR: 200 ° C., load 5.0 kg) of the styrene-butadiene block copolymer is not particularly limited, but is preferably 100 or less, more preferably 2 to 80.
  • SBS Asaprene (registered trademark) A, 125 and 126S manufactured by Asahi Kasei Chemicals, Asaprene (registered trademark) T-411, T-432, T-
  • SBS Asaprene (registered trademark) A, 125 and 126S manufactured by Asahi Kasei Chemicals
  • Commercially available products such as 437, T-438 and T-439 can be used, and commercially available products such as Tuftec (registered trademark) P1000, P1500 and P2000 manufactured by the same company can be used as the SBBS.
  • other styrene-butadiene block copolymers include, for example, styrene-isoprene-styrene block copolymer (SIS), styrene-ethylene-propylene-styrene block copolymer A combination (SEPS), a styrene-ethylene-butylene-styrene block copolymer (SEBS), a styrene-ethylene-ethylene-propylene-styrene block copolymer (SEEPS), or the like can be used in combination.
  • SEBS styrene-isoprene-styrene block copolymer
  • SEBS styrene-ethylene-propylene-styrene block copolymer
  • SEEPS styrene-ethylene-ethylene-propylene-styrene block copolymer
  • SEEPS styrene-ethylene-ethylene-propylene-styrene block
  • the nitrone derivative contained in the adhesive composition of the present invention is not particularly limited as long as it is a compound in which an oxygen atom is bonded to a nitrogen atom of a Schiff base.
  • the nitrone derivative is a nitrone having an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent, because both the thermal stability and the heat resistance are improved. It is preferable that there is, for example, a nitrone represented by the following formula (a).
  • X and Y each independently represent an aliphatic or aromatic hydrocarbon group which may have a substituent, and at least one of X or Y has a substituent. Or an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • Examples of the aliphatic hydrocarbon group represented by X and Y include an alkyl group, a cycloalkyl group, and an alkenyl group.
  • Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, Examples thereof include a tert-pentyl group, 1-methylbutyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, n-hexyl group, n-heptyl group, and n-octyl group.
  • Alkyl groups having 1 to 6 carbon atoms are more preferable.
  • the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. Among them, a cycloalkyl group having 3 to 10 carbon atoms is preferable, and a cycloalkyl group having 3 to 6 carbon atoms is preferable. More preferred.
  • Examples of the alkenyl group include a vinyl group, a 1-propenyl group, an allyl group, an isopropenyl group, a 1-butenyl group, and a 2-butenyl group. Among them, an alkenyl group having 2 to 18 carbon atoms is preferable. An alkenyl group having 2 to 6 carbon atoms is more preferable.
  • Examples of the aromatic hydrocarbon group represented by X and Y include an aryl group and an aralkyl group.
  • the aryl group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, and a biphenyl group. Among them, an aryl group having 6 to 14 carbon atoms is preferable, and an aryl group having 6 to 10 carbon atoms is more preferable. A phenyl group and a naphthyl group are more preferable.
  • Examples of the aralkyl group include a benzyl group, a phenethyl group, and a phenylpropyl group. Among them, an aralkyl group having 7 to 13 carbon atoms is preferable, an aralkyl group having 7 to 11 carbon atoms is more preferable, and a benzyl group is preferable. Further preferred.
  • Examples of the aromatic heterocyclic group represented by X and Y include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl (imidazole), oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl (pyridine). Group), furan group, thiophene group, pyridazinyl group, pyrimidinyl group, pyrazinyl group and the like. Of these, a pyridyl group is preferable.
  • the substituent that the hydrocarbon group represented by X and Y may have is not particularly limited, and examples thereof include a lower alkyl group having 1 to 4 carbon atoms, a hydroxy group, an amino group, a nitro group, a carbonyl group, and a carboxy group. Group, carbonate group, urethane group, sulfonyl group, alkoxy group, ester group, halogen atom and the like.
  • the aromatic hydrocarbon group having such a substituent include an aryl group having a substituent such as a tolyl group and a xylyl group; and a substituent such as a methylbenzyl group, an ethylbenzyl group, and a methylphenethyl group.
  • the nitrone represented by the formula (a) is an aromatic hydrocarbon group or an aromatic heterocyclic group in which at least one of X and Y in the formula (a) may have a substituent.
  • both X and Y are preferably an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent.
  • the above nitrone derivative has better thermal stability and can improve intermolecular force, so that the nitrone having an aromatic hydrocarbon group or aromatic heterocyclic group having a carboxy group as a substituent (hereinafter referred to as “nitrone”)
  • nitrone aromatic hydrocarbon group or aromatic heterocyclic group having a carboxy group as a substituent
  • carboxy nitrone For convenience, it is also referred to as “carboxy nitrone”
  • examples thereof include nitrones represented by the following formula (b).
  • m and n each independently represent an integer of 0 to 5, and the sum of m and n is 1 or more.
  • the integer represented by m is preferably an integer of 0 to 2, more preferably an integer of 0 to 1, because the solubility in a solvent at the time of synthesizing nitrone is improved and the synthesis is facilitated.
  • the integer represented by n is preferably an integer of 0 to 2, more preferably an integer of 0 to 1, because the solubility in a solvent at the time of synthesizing nitrone is improved and the synthesis is facilitated.
  • the total of m and n (m + n) is preferably 1 to 4 and more preferably 1 to 2 because the solubility in the polymer is good and the reactivity is excellent.
  • the nitrone derivatives exemplified above may be used alone or in combination of two or more.
  • the above carboxynitrone and an aromatic hydrocarbon group or aromatic heterocyclic group which may have a functional group (excluding the carboxy group) for the reason that the heat resistance becomes better and the economy is also excellent. It is preferable to use in combination with a nitrone having a nitrogen atom (for example, diphenylnitrone).
  • the content of the nitrone derivative is 1 to 10 parts by mass with respect to 100 parts by mass of the styrene-butadiene block copolymer.
  • the amount is preferably 1 to 5 parts by mass with respect to 100 parts by mass of the coalescence.
  • the method for synthesizing the nitrone derivative is not particularly limited, and a conventionally known method can be used.
  • a compound having a hydroxyamino group (—NHOH) and a compound having an aldehyde group (—CHO) are mixed in an organic solvent (eg, methanol, ethanol) at a molar ratio of 1.5: 1 to 1: 1.5. , Tetrahydrofuran, etc.) at room temperature for 1 to 24 hours to react both groups to give a nitrone having a nitrone group represented by the formula “—N + (—O ⁇ ) ⁇ CH—”.
  • the adhesive composition of the present invention may further contain an additive as necessary within the range not impairing the object and effect of the present invention, in addition to the above-described styrene-butadiene block copolymer and nitrone derivative.
  • additives examples include diene rubbers and non-diene rubbers other than the styrene-butadiene block copolymer, thermoplastic elastomers, catalysts, fillers, plasticizers, softeners, adhesion promoters, tackifiers, waxes, Examples include vulcanization accelerators, pigments, dyes, antioxidants, antioxidants, antistatic agents, flame retardants, stabilizers, fragrances, thixotropic agents, ultraviolet absorbers, and silane coupling agents.
  • the filler examples include calcium carbonate, talc, white carbon, silica, and carbon black.
  • silica when silica is used as a filler, the content thereof is 5 parts by mass or less with respect to 100 parts by mass of the styrene-butadiene block copolymer, because the heat resistance becomes better. Preferably, it is 4 parts by mass or less.
  • plasticizer examples include paraffinic, naphthenic or aromatic process oils; liquid resins such as liquid polybutene, liquid polybutadiene or liquid polyisoprene; liquid paraffin; olefin process oil; Can be mentioned.
  • Examples of the tackifier include rosin resin, terpene resin, petroleum resin, coumarone-indene resin and the like, modified products thereof, and hydrogenated products.
  • examples of petroleum resins include aliphatic, alicyclic and aromatic resins made from petroleum. Specifically, C5 petroleum resins, C9 petroleum resins, and copolymer petroleum resins. Suitable examples include alicyclic saturated hydrocarbon resins and styrene petroleum resins.
  • anti-aging agent examples include hindered phenol compounds and hindered amine compounds.
  • the method for producing the adhesive composition of the present invention is not particularly limited, and examples thereof include a method of kneading each of the above-described components using a known method and apparatus (for example, a Banbury mixer, a kneader, a roll, etc.). It is done.
  • a known method and apparatus for example, a Banbury mixer, a kneader, a roll, etc.
  • the ratio of the melt viscosity at 120 ° C. to the melt viscosity at 180 ° C. is preferably 7 or more, more preferably 8 or more.
  • the adhesive material composition of the present invention preferably has a melt viscosity at 180 ° C. of 4000 mPas or less, and more preferably 3000 mPas or less.
  • members (adhered bodies) that can use the adhesive composition of the present invention include glass; various metals such as aluminum, anodized aluminum, iron, steel plate, galvanized steel plate, copper, and stainless steel; mortar and Porous members such as stone materials; members coated by fluorine electrodeposition, acrylic electrodeposition, fluorine coating, urethane coating, acrylic urethane coating; such as silicone, modified silicone, urethane, polysulfide, and polyisobutylene Cured products of sealing materials; polyolefins such as polyethylene, resins such as vinyl chloride resins and acrylic resins; rubbers such as NBR and EPDM.
  • various metals such as aluminum, anodized aluminum, iron, steel plate, galvanized steel plate, copper, and stainless steel
  • mortar and Porous members such as stone materials
  • members coated by fluorine electrodeposition, acrylic electrodeposition, fluorine coating, urethane coating, acrylic urethane coating such as silicone, modified silicone, urethane, polysulfide, and polyis
  • Examples 1 to 13 The components shown in Table 1 below were blended in the proportions (parts by mass) shown in Table 1 below. Specifically, first, a styrene-butadiene block copolymer and a plasticizer are added to a glass container whose temperature in the container is set to 160 ° C., kneaded for 5 minutes, then a nitrone derivative is added, and further 10 minutes. Kneaded. Next, the temperature in the glass container was set to 130 ° C., a filler and a tackifier were added, kneaded for 10 minutes, an anti-aging agent was added, and the mixture was further kneaded for 5 minutes. Thereafter, the mixture was taken out and cooled to prepare a hot melt adhesive composition.
  • Example 14 The components shown in Table 1 below were blended in the proportions (parts by mass) shown in Table 1 below. Specifically, a hot melt adhesive composition was prepared in the same manner as in Example 1 except that the temperature in the glass container when kneading the styrene-butadiene block copolymer was 130 ° C. .
  • melt viscosity and melt viscosity ratio The melt viscosity (mPas) at 120 ° C., 140 ° C., 160 ° C. and 180 ° C. of each hot melt adhesive composition was measured using a single cylindrical rotational viscometer. Moreover, the ratio (120 degreeC viscosity / 180 degreeC viscosity) of the melt viscosity in 120 degreeC and the melt viscosity in 180 degreeC was computed from the measurement result.
  • Softening point The softening point (° C.) of each hot melt adhesive composition was measured by a ring method using a glycerin bath based on JIS K6863: 1994.
  • thermo stability Each hot melt adhesive composition was allowed to stand for 72 hours in a melted state at 180 ° C. The presence or absence of foreign matter (gelled product) after 72 hours was confirmed. If there is no foreign material, it can be evaluated that the thermal stability is excellent, and if there is a foreign material, it can be evaluated that the thermal stability is poor.
  • Example 1 and Example 14 were washed with cyclohexane to isolate only the polymer, and then 1 H-NMR (proton nuclear magnetic resonance) measurement was performed.
  • the polymer derived from the hot melt adhesive composition prepared in Example 1 had a proton chemical shift associated with the disappearance of butadiene (double bond) in the styrene-butadiene block copolymer. It was confirmed that a cycloaddition reaction (see the above formula (I)) occurred between a part of the nitrone derivative and the butadiene double bond of the styrene-butadiene block copolymer.
  • SBS1 Asaprene T-439 (styrene / butadiene mass ratio: 45/55, manufactured by Asahi Kasei Chemicals Corporation)
  • SBS2 Asaprene T-432 (styrene / butadiene mass ratio: 30/70, manufactured by Asahi Kasei Chemicals)
  • SBBS Tuftec P1000 (styrene / butadiene mass ratio: 30/70, manufactured by Asahi Kasei Chemicals Corporation)
  • Nitron derivative Carboxynitrone, pyridylnitrone, diphenylnitrone synthesized by the above-described method was used.
  • the hot melt adhesive compositions of Examples 1 to 14 prepared by blending a specific amount of a nitrone derivative with a predetermined styrene-butadiene block copolymer are excellent in thermal stability and peel at 120 ° C. It was found that the strength (heat resistance) was also good. In particular, when Example 1 and Comparative Example 1 are compared, the melt viscosity at 120 ° C. rises almost twice due to the presence or absence of the nitrone derivative, and the melt viscosity at 180 ° C. becomes comparable, and the nitrone derivative is added. Thus, it can be seen that not only the thermal stability and heat resistance, but also the workability at the time of coating has been remarkably improved.

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

Abstract

L'invention concerne une composition adhésive thermofusible qui est hautement thermostable et montre aussi une bonne résistance à la chaleur. Ladite composition adhésive thermofusible contient un ou des copolymère(s) à blocs de styrène-butadiène, à savoir un copolymère à blocs de styrène-butadiène-styrène (SBS)et/ou un copolymère à blocs de styrène-butadiène-butylène-styrène (SBBS), et 1 à 10 parties en masse d'un dérivé de nitrone par 100 parties en masse du ou des copolymère(s) à blocs de styrène-butadiène.
PCT/JP2014/055975 2013-03-08 2014-03-07 Composition adhésive thermofusible WO2014136940A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020157025286A KR101622324B1 (ko) 2013-03-08 2014-03-07 핫멜트 접착제 조성물
CN201480025871.7A CN105209566B (zh) 2013-03-08 2014-03-07 热熔粘接剂组合物
PH12015501989A PH12015501989A1 (en) 2013-03-08 2015-09-07 Hot melt adhesive composition

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JP2013-046627 2013-03-08
JP2013046627A JP5578249B1 (ja) 2013-03-08 2013-03-08 ホットメルト接着剤組成物

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KR (1) KR101622324B1 (fr)
CN (1) CN105209566B (fr)
PH (1) PH12015501989A1 (fr)
WO (1) WO2014136940A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107250244A (zh) * 2015-03-19 2017-10-13 横滨橡胶株式会社 轮胎胎面用橡胶组合物及充气轮胎
WO2018151190A1 (fr) * 2017-02-17 2018-08-23 積水フーラー株式会社 Adhésif thermofusible et stratifié étirable
CN112772005A (zh) * 2018-09-25 2021-05-07 积水富乐株式会社 电子电路安装基板用热熔涂敷剂
US11312886B2 (en) 2016-04-08 2022-04-26 Avery Dennison Corporation Clear hot melt adhesives

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WO2018070676A1 (fr) * 2016-10-14 2018-04-19 박희대 Composition de résine réactive thermofusible et film réactif thermofusible fabriqué à partir de la résine
JP7060885B2 (ja) * 2019-12-11 2022-04-27 誠泰工業科技股▲分▼有限公司 エコ防水ホットメルト接着剤組成物、そのフィルム材及び製造方法
KR102309698B1 (ko) 2020-01-16 2021-10-07 주식회사 이레A.T (에이티) 고내구성 및 고접착력을 갖는 핫멜트 접착제
JPWO2022181690A1 (fr) * 2021-02-26 2022-09-01

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JP2013032471A (ja) * 2011-08-03 2013-02-14 Yokohama Rubber Co Ltd:The ゴム組成物

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JP5471639B2 (ja) 2010-03-12 2014-04-16 Ｄｉｃ株式会社 湿気硬化型ポリウレタンホットメルト接着剤、及びそれを用いて得られる化粧造作部材
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JP2011506650A (ja) * 2007-12-12 2011-03-03 ハインリヒ−ハイネ−ウニベルジテート ポリニトロン及び不飽和ポリマーを架橋するためのその使用
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Cited By (6)

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Publication number Priority date Publication date Assignee Title
CN107250244A (zh) * 2015-03-19 2017-10-13 横滨橡胶株式会社 轮胎胎面用橡胶组合物及充气轮胎
US11312886B2 (en) 2016-04-08 2022-04-26 Avery Dennison Corporation Clear hot melt adhesives
WO2018151190A1 (fr) * 2017-02-17 2018-08-23 積水フーラー株式会社 Adhésif thermofusible et stratifié étirable
JPWO2018151190A1 (ja) * 2017-02-17 2019-02-21 積水フーラー株式会社 ホットメルト接着剤及び伸縮性積層体
CN112772005A (zh) * 2018-09-25 2021-05-07 积水富乐株式会社 电子电路安装基板用热熔涂敷剂
EP3860318A4 (fr) * 2018-09-25 2022-06-15 Sekisui Fuller Company, Ltd. Agent de revêtement thermofusible pour carte de circuit imprimé électronique montée sur un composant

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KR20150142674A (ko) 2015-12-22
JP2014172995A (ja) 2014-09-22
CN105209566B (zh) 2017-12-05
JP5578249B1 (ja) 2014-08-27
PH12015501989B1 (en) 2016-01-11
PH12015501989A1 (en) 2016-01-11
CN105209566A (zh) 2015-12-30
KR101622324B1 (ko) 2016-05-18

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