WO2020044829A1 - Adhésif sensible à la pression à base d'uréthane et feuille d'adhésif sensible à la pression - Google Patents

Adhésif sensible à la pression à base d'uréthane et feuille d'adhésif sensible à la pression Download PDF

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Publication number
WO2020044829A1
WO2020044829A1 PCT/JP2019/028034 JP2019028034W WO2020044829A1 WO 2020044829 A1 WO2020044829 A1 WO 2020044829A1 JP 2019028034 W JP2019028034 W JP 2019028034W WO 2020044829 A1 WO2020044829 A1 WO 2020044829A1
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WO
WIPO (PCT)
Prior art keywords
sensitive adhesive
pressure
active hydrogen
mass
surfactant
Prior art date
Application number
PCT/JP2019/028034
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English (en)
Japanese (ja)
Inventor
嘉孝 戸根
秀平 齋藤
慎吾 田邉
Original Assignee
東洋インキＳｃホールディングス株式会社
トーヨーケム株式会社
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 東洋インキＳｃホールディングス株式会社, トーヨーケム株式会社 filed Critical 東洋インキＳｃホールディングス株式会社
Priority to CN201980003934.1A priority Critical patent/CN111032813B/zh
Priority to KR1020207035913A priority patent/KR20210049716A/ko
Publication of WO2020044829A1 publication Critical patent/WO2020044829A1/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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • 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
    • 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
    • C09J2301/312—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 parameters being the characterizing feature

Definitions

  • the pressure-sensitive adhesive sheet has good removability that can be easily re-peeled from the adherend when it is detached from the adherend, both initially (before aging) and after aging (especially after (wet) heat aging). Is preferred.
  • the anchoring property between the adherend and the pressure-sensitive adhesive layer is increased, so that the pressure-sensitive adhesive strength of the pressure-sensitive adhesive layer is increased and the removability is reduced. Tends to decrease.
  • the pressure-sensitive adhesive sheet preferably has good removability even when exposed to a (moist) heat environment, and preferably has no adherend contamination in which the pressure-sensitive adhesive component remains on the surface of the adherend after re-peeling.
  • Hydroxy-terminated urethane prepolymer examples include a hydroxyl-terminal urethane which is a reaction product obtained by copolymerizing one or more active hydrogen group-containing compounds (HX) and one or more polyisocyanates (N). Prepolymers (UPH) are preferred.
  • the copolymerization reaction can be carried out in the presence of one or more catalysts, if necessary.
  • One or more solvents can be used in the copolymerization reaction, if necessary.
  • the number average molecular weight (Mn) per functional group of the active hydrogen group-containing compound (HX) is not particularly limited. Since the adhesive strength and wettability of the adhesive layer are suitable, the one or more active hydrogen group-containing compounds (HX) preferably have Mn of 500 or more, more preferably 1000 or more, particularly preferably 2000 or more, and most preferably. Preferably contains an active hydrogen group-containing compound of 3000 or more.
  • non-tin compound examples include titanium compounds such as dibutyl titanium dichloride, tetrabutyl titanate, and butoxy titanium trichloride; lead compounds such as lead oleate, lead 2-ethylhexanoate, lead benzoate, and lead naphthenate; Irons such as iron-ethylhexanoate and iron acetylacetonate; cobalts such as cobalt benzoate and cobalt 2-ethylhexanoate; zincs such as zinc naphthenate and zinc 2-ethylhexanoate; zirconium naphthenate; Zirconium-based is exemplified.
  • the type and amount of the catalyst can be appropriately designed within a range in which the reaction proceeds favorably.
  • the polymerization method of the hydroxyl group-terminated urethane prepolymer (UPH) is not particularly limited, and a known polymerization method such as a bulk polymerization method and a solution polymerization method can be applied.
  • the polymerization procedure of the hydroxyl-terminated urethane prepolymer (UPH) includes: Procedure 1) One or more active hydrogen group-containing compounds (HX), one or more polyisocyanates (N), one or more catalysts as needed, and one or more solvents as needed.
  • the pressure-sensitive adhesive of the present invention has at least one surfactant (S) having a cationic hydrophilic group and having an amine value of 0.1 to 160 mgKOH / g, preferably 0.1 to 150 mgKOH / g in terms of nonvolatile components. including.
  • the surfactant (S) one or more known cationic surfactants and / or amphoteric surfactants can be used.
  • the amine value is 0.1 to 160 mgKOH / g in terms of non-volatile components. If it is, there is no particular limitation.
  • a hydrolysis resistant agent When a carboxy group is generated by a hydrolysis reaction in the adhesive layer under a (wet) heat environment or the like, a hydrolysis resistant agent can be used to block the carboxy group.
  • the hydrolysis stabilizer include carbodiimide-based, oxazoline-based, and epoxy-based. Above all, carbodiimides are preferred from the viewpoint of the effect of inhibiting hydrolysis.
  • the amount of the hydrolysis stabilizer added is not particularly limited, and is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 4.5 parts by mass, per 100 parts by mass of the active hydrogen group-containing compound (H). And particularly preferably 0.5 to 3 parts by mass.
  • Examples of the phosphorus-based compound include triphenyl phosphite, diphenyl isodecyl phosphite, 4,4′-butylidene-bis (3-methyl-6-tert-butylphenyl ditridecyl) phosphite, and cyclic neopentanetetrayl Bis (octadecylphosphite), tris (nonylphenyl) phosphite, tris (monononylphenyl) phosphite, tris (dinonylphenyl) phosphite, diisodecylpentaerythritol diphosphite, 9,10-dihydro-9-oxa- 10-phosphaphenanthrene-10-oxide, 10- (3,5-di-tert-butyl-4-hydroxybenzyl) -9,10-dihydro-9-oxa-10-phosphaphenanthren
  • the pressure-sensitive adhesive of the present invention optionally contains one or more antistatic agents (AS agents) (excluding those corresponding to the active hydrogen group-containing compound (H) and the surfactant (S)).
  • AS agents antistatic agents
  • examples of the antistatic agent include an inorganic salt, an ionic liquid, an ionic solid, and a surfactant. Among them, an ionic liquid and an ionic solid are preferable.
  • the “ionic liquid” is also called a room temperature molten salt, and is a salt having a fluidity at 25 ° C.
  • ionic solids containing phosphonium ions include, for example, tetrabutylphosphonium bisfluorosulfonylimide, tetrabutylphosphonium bistrifluoromethylsulfonylimide, tetrabutylphosphonium bispentafluoroethylsulfonylimide, tetrabutylphosphonium bisheptafluoropropylsulfonylimide, tetrabutylphosphonium Bisnonanefluorobutylsulfonylimide, tributylhexadecylphosphonium bisfluorosulfonylimide, tributylhexadecylphosphonium bistrifluoromethylsulfonylimide, tributylhexadecylphosphonium bispentafluoroethylsulfonylimide, tributylhexadecylphosphonium bis
  • ionic solids containing ammonium ions include, for example, lauryltrimethylammonium chloride, tributylmethylbistrifluoromethylsulfonylimide, tributylmethylbispentafluoroethylsulfonylimide, tributylmethylbisheptafluoropropylsulfonylimide, tributylmethylmubisnonanefluorobutylsulfonylimide Octyltributylbistrifluoromethylsulfonylimide, octyltributylbispentafluoroethylsulfonylimide, octyltributylbisheptafluoropropylsulfonylimide, octyltributylmubisnonanefluorobutylsulfonylimide, tetrabutylbisfluorosulfonylimide, te
  • the pressure-sensitive adhesive sheet can be manufactured by a known method.
  • the pressure-sensitive adhesive of the present invention is applied to the surface of a substrate sheet to form a coating layer composed of the pressure-sensitive adhesive of the present invention.
  • Known coating methods can be applied, and examples include a roll coater method, a comma coater method, a die coater method, a reverse coater method, a silk screen method, and a gravure coater method.
  • the coating layer is dried and cured to form an adhesive layer made of a cured product of the adhesive of the present invention.
  • the heating and drying temperature is not particularly limited, and is preferably about 60 to 150 ° C.
  • the pressure-sensitive adhesive sheet of the present invention includes a flat panel display and a touch panel display (collectively referred to simply as a “display”), and a substrate (a glass substrate and an ITO on a glass substrate) manufactured or used in these manufacturing processes. (ITO / glass substrate or the like on which (indium tin oxide) film is formed) and a surface protection sheet for optical members and the like.
  • HX-18 Preminol 7012, manufactured by Asahi Glass Co., Ltd., trifunctional polyether polyol, hydroxyl value 16.8, degree of unsaturation 0.02.
  • the unit of the degree of unsaturation is meq / g.
  • a release sheet having a thickness of 38 ⁇ m (Super Stick SP-PET38, manufactured by Lintec Corporation) was adhered on the adhesive layer to obtain an adhesive sheet.
  • the evaluation of the initial curing property after curing for 5 hours under the condition of 23 ° C. and 50% RH, the evaluation was performed. Other evaluations were performed after curing for one week under the condition of 23 ° C. and 50% RH.
  • a test piece having a width of 25 mm and a length of 100 mm was cut out from the pressure-sensitive adhesive sheet after curing for one week in an atmosphere of 23 ° C. and 50% RH.
  • the release sheet was peeled off from the test piece, the exposed adhesive layer was adhered to a caustic soda glass plate, and a 2 kg roll was reciprocated one time and pressed. Then, it was left for 1 hour in an atmosphere at 150 ° C. Then, after air cooling in an atmosphere of 23 ° C.
  • Each of the two laminates was taken out of the oven, air-cooled in an atmosphere of 23 ° C. and 50% RH for 3 hours, and then the adhesive sheet was peeled off from the glass plate to evaluate adherend contamination.
  • the surface of the glass plate on which the adhesive sheet was stuck in the dark room was irradiated with LED (light emitting diode) lamp light, and evaluated by visual observation.
  • the evaluation criteria are as follows. ⁇ : Excellent in that no adhesion component of the adhesive layer was observed on the glass surface in any of the samples under the heating conditions of 60 ° C.-90% RH and 85 ° C.-85% RH.
  • the pressure-sensitive adhesive sheet obtained in Comparative Example 2 in which the amount of the surfactant (S) having a cationic hydrophilic group added to 100 parts by mass of the active hydrogen group-containing compound (H) was more than 20 parts by mass, had an initial curability and heat. The increase rates of the adhesive strength before and the adhesive strength after heating were poor, and the adherend contamination was remarkable.

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

Abstract

La présente invention concerne un adhésif sensible à la pression apte à former une couche d'adhésif sensible à la pression qui permet une réduction du pouvoir adhésif et une aptitude à l'élimination favorable même pendant une période initiale (avant le passage du temps) et après le passage du temps (en particulier après une période de temps chauffée (humide)) et qui laisse une tache moindre sur une partie adhérée après son élimination. Selon la présente invention, l'adhésif sensible à la pression est un adhésif sensible à la pression à base d'uréthane, comprenant : au moins un type d'un composé (H) contenant un groupe hydrogène actif possédant une pluralité de groupes hydrogène actifs par molécule ; au moins un type d'un composé isocyanate multifonctionnel (I) ; et au moins un type d'un tensioactif (S) possédant un groupe hydrophile cationique, le tensioactif (S) possédant une valeur amine de 0,1 à 150 mgKOH/g en termes de contenus non volatils, et la quantité contenue du tensioactif (S) étant de 0,01 à 20 parties en masse par rapport à 100 parties en masse du composé (H) contenant un groupe hydrogène actif.
PCT/JP2019/028034 2018-08-29 2019-07-17 Adhésif sensible à la pression à base d'uréthane et feuille d'adhésif sensible à la pression WO2020044829A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201980003934.1A CN111032813B (zh) 2018-08-29 2019-07-17 氨基甲酸酯系粘着剂及粘着片
KR1020207035913A KR20210049716A (ko) 2018-08-29 2019-07-17 우레탄계 점착제 및 점착 시트

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018-159967 2018-08-29
JP2018159967A JP6516056B1 (ja) 2018-08-29 2018-08-29 ウレタン系粘着剤および粘着シート

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Publication Number Publication Date
WO2020044829A1 true WO2020044829A1 (fr) 2020-03-05

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PCT/JP2019/028034 WO2020044829A1 (fr) 2018-08-29 2019-07-17 Adhésif sensible à la pression à base d'uréthane et feuille d'adhésif sensible à la pression

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JP (1) JP6516056B1 (fr)
KR (1) KR20210049716A (fr)
CN (1) CN111032813B (fr)
TW (1) TWI808226B (fr)
WO (1) WO2020044829A1 (fr)

Families Citing this family (6)

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Publication number Priority date Publication date Assignee Title
JP7322607B2 (ja) * 2019-09-05 2023-08-08 東洋インキＳｃホールディングス株式会社 溶剤型粘着剤および粘着シート
JP6769574B1 (ja) * 2020-06-01 2020-10-14 東洋インキＳｃホールディングス株式会社 粘着シート、粘着シート付き被着体、および粘着シートの使用方法
KR102266586B1 (ko) * 2020-08-25 2021-06-17 부산대학교 산학협력단 분자설계를 통해 점착력 제어가 가능한 폴리우레탄계 점착제 및 이의 제조방법
CN114315603B (zh) * 2020-09-30 2024-04-05 上海凯赛生物技术股份有限公司 一种1,5-戊二胺的提取方法及其所得的1,5-戊二胺产品
KR102584942B1 (ko) * 2021-12-20 2023-10-05 정윤종 단열성 및 완충성을 향상시킨 건축용 시트 및 상기 시트를 이용한 시공방법
CN114369422A (zh) * 2021-12-29 2022-04-19 苏州赛伍应用技术股份有限公司 一种可直接收卷的pu保护膜及其制备方法

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JP2018062628A (ja) * 2016-10-14 2018-04-19 東洋インキＳｃホールディングス株式会社 感圧式接着剤、及び接着フィルム
JP2018119028A (ja) * 2017-01-23 2018-08-02 東洋インキＳｃホールディングス株式会社 感圧式接着剤及び接着フィルム

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JP5200359B2 (ja) * 2006-09-29 2013-06-05 オート化学工業株式会社 硬化性組成物
JP5526646B2 (ja) * 2009-08-07 2014-06-18 東洋インキＳｃホールディングス株式会社 帯電防止性感圧式接着剤組成物、並びにそれを用いてなる帯電防止性感圧式接着シート、及び積層体
JP2014162821A (ja) 2013-02-22 2014-09-08 Nitto Denko Corp 表面保護フィルム
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JPH0995473A (ja) * 1995-09-29 1997-04-08 Henkel Japan Kk 低塩分含有ベタイン型両性界面活性剤の製造方法
JP2018062628A (ja) * 2016-10-14 2018-04-19 東洋インキＳｃホールディングス株式会社 感圧式接着剤、及び接着フィルム
JP2018119028A (ja) * 2017-01-23 2018-08-02 東洋インキＳｃホールディングス株式会社 感圧式接着剤及び接着フィルム

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Publication number Publication date
CN111032813A (zh) 2020-04-17
JP6516056B1 (ja) 2019-05-22
KR20210049716A (ko) 2021-05-06
TWI808226B (zh) 2023-07-11
TW202020090A (zh) 2020-06-01
CN111032813B (zh) 2021-12-21
JP2020033434A (ja) 2020-03-05

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