WO2015137264A1 - チオエーテル含有（メタ）アクリレート誘導体、およびこれを含有する密着性向上剤 - Google Patents

チオエーテル含有（メタ）アクリレート誘導体、およびこれを含有する密着性向上剤 Download PDF

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WO2015137264A1
WO2015137264A1 PCT/JP2015/056773 JP2015056773W WO2015137264A1 WO 2015137264 A1 WO2015137264 A1 WO 2015137264A1 JP 2015056773 W JP2015056773 W JP 2015056773W WO 2015137264 A1 WO2015137264 A1 WO 2015137264A1
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formula
meth
thioether
group
adhesion
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PCT/JP2015/056773
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English (en)
French (fr)
Japanese (ja)
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寛 田代
一洋 幸田
俊伸 藤村
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日油株式会社
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Priority to KR1020157034991A priority Critical patent/KR101748067B1/ko
Priority to CN201580000256.5A priority patent/CN105473561B/zh
Publication of WO2015137264A1 publication Critical patent/WO2015137264A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • 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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives

Definitions

  • the present invention relates to a novel thioether-containing (meth) acrylate derivative suitably used for an adhesion improver or the like.
  • an adhesion improver such as a silane coupling agent has been added to the paint for the purpose of improving adhesion (for example, JP-A-7-300491). Issue no.).
  • the silane coupling agent decomposes when heated, when used in a mass production line, silicon oxide is deposited in a heating furnace such as an oven, causing contamination.
  • the silane coupling agent cannot be said to have a sufficient effect of improving adhesion, for example, by simultaneously adding adhesion assistants such as salts such as titanium and zirconium, amines such as imidazole, phosphate esters and urethane resins.
  • adhesion could be achieved for the first time.
  • the addition of the adhesion aid not only leads to an increase in manufacturing man-hours and costs, but the addition of the adhesion aid reduces the storage stability of the paint at room temperature and decreases the heat resistance and hardness. There was a problem.
  • Japanese Patent Application Laid-Open No. 2013-249282 discloses that a thioether-containing urea derivative having a specific structure is used as an adhesion improver, thereby improving adhesion without using an adhesion aid. Is disclosed.
  • the present invention has been accomplished in view of the above circumstances, and the object thereof is to add to paints and the like, exhibit an effect of improving adhesion without an adhesion aid even in cold regions, and the obtained coating film It is to provide a material having flexibility.
  • the present invention includes the following [1] to [3].
  • a in the formula is an integer from 1 to 2
  • b is an integer from 1 to 2
  • R 2 is A divalent group represented by the following formula 3 or 4.
  • the R 3 is a hydrocarbon group having 1 to 12 carbon atoms.
  • R 5 is a hydrogen atom or a methyl group.
  • R 5 is a hydrogen atom or a methyl group.
  • An adhesion improver comprising the thioether-containing (meth) acrylate derivative according to [1] or [2] as an active ingredient.
  • (meth) acrylate is a concept including both “methacrylate” and “acrylate”.
  • the thioether-containing (meth) acrylate derivative of the present invention exhibits an effect of improving adhesion without an adhesion assistant even in a cold environment such as ⁇ 10 ° C., and the resulting coating film has flexibility. Have. Therefore, for example, by adding a small amount to the paint, it is possible to impart high adhesion to the paint without requiring the addition of an adhesion assistant.
  • the above effect is that, in a cold environment, the ester group having a specific carbon chain imparts flexibility to the paint, and this ester group does not prevent the thioether group and the base material from approaching each other. It is considered that the effect of improving the performance is accurately demonstrated.
  • Example 3 is an IR spectrum of the compound 1 obtained in Example 1-1.
  • 2 is an IR spectrum of the compound 2 obtained in Example 1-2.
  • 3 is an IR spectrum of the compound 3 obtained in Example 1-3.
  • 4 is an IR spectrum of the compound 4 obtained in Example 1-4. It is an IR spectrum of the compound 5 obtained in Example 1-5.
  • 1 is a 1 H-NMR spectrum of Compound 1 obtained in Example 1-1.
  • 1 is a 1 H-NMR spectrum of Compound 2 obtained in Example 1-2.
  • 1 is a 1 H-NMR spectrum of Synthesis Compound 3 obtained in Example 1-3.
  • 1 is a 1 H-NMR spectrum of Compound 4 obtained in Example 1-4.
  • 1 is a 1 H-NMR spectrum of the compound 5 obtained in Example 1-5.
  • the thioether-containing (meth) acrylate derivative of this embodiment is a compound represented by the following formula 1.
  • a in the formula is an integer from 1 to 2
  • b is an integer from 1 to 2
  • R 2 is A divalent group represented by the following formula 3 or 4.
  • the R 3 is a hydrocarbon group having 1 to 12 carbon atoms.
  • Examples of the hydrocarbon group having 1 to 12 carbon atoms, which is R 3 in the above formula 1, include a linear alkyl group, an alkyl group having a side chain, and a cyclic alkyl group.
  • R 4 in the above formula 2 is a methylene group, an ethylene group, or an isopropylene group, and an ethylene group or an isopropylene group is particularly preferable because the effect of improving adhesion is enhanced.
  • the thioether-containing (meth) acrylate derivative represented by the above formula 1 is represented by, for example, an acrylic compound having a (meth) acrylate group (hereinafter referred to as A component) as represented by the following formula 5 and the following formula 6. It can be obtained by reacting with a polyvalent thiol compound having a thiol group (—SH) (hereinafter referred to as B component).
  • a component an acrylic compound having a (meth) acrylate group
  • B component a polyvalent thiol compound having a thiol group
  • R 3 is a hydrocarbon group having 1 to 12 carbon atoms.
  • R 5 is a hydrogen atom or a methyl group.
  • Examples of the component A represented by the above formula 5 include methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, and the like.
  • component B represented by the above formula 6 tris-[(3-mercaptopropionyloxy) -ethyl] -isocyanurate, tris-[(3-mercaptobutyryloxy) -ethyl]]-isocyanurate, tris- [ (3-mercaptobutyryloxy) -ethyl]]-isocyanurate.
  • the thioether-containing (meth) acrylate derivative of the present embodiment is produced by reacting the A component and the B component at a temperature of 5 ° C. or higher, and is preferably reacted at 60 to 100 ° C.
  • the reaction can be performed at 60 ° C. or higher, the reaction can be performed in a short time such as within 5 hours.
  • a base catalyst and a radical generator are added, it can be made to react in a high yield in a shorter time.
  • the base catalyst is preferably an amine base catalyst, and primary, secondary or tertiary amines or imidazole compounds can be used.
  • the primary amine include methylamine, ethylamine, propylamine, butylamine, and ethylenediamine.
  • Secondary amines include dimethylamine, diethylamine, dipropylamine, methylethylamine, diphenylamine and the like.
  • Tertiary amines include trimethylamine, triethylamine, tripropylamine, triphenylamine, 1,8-diazabicyclo (5.4.0) undec-aminomethyl) phenol, and the like.
  • imidazole compounds include 1-methylimidazole, 1,2-dimethylimidazole, 1,4-dimethyl-2-ethylimidazole, imidazole analogues such as 1-phenylimidazole, 1-methyl-2-oxymethylimidazole, Alkyl derivatives such as 1-methyl-2-oxyethylimidazole, nitro and amino derivatives such as 1-methyl-4 (5) -nitroimidazole, 1,2-dimethyl-5 (4) -aminoimidazole, benzimidazole, 1 -Methylbenzimidazole, 1-methyl-benzylbenzimidazole and the like.
  • a peroxide or an azo compound is preferable.
  • the peroxide include dibenzoyl peroxide, tert-butylperoxy-2-ethylhexanoate, and dilauroyl peroxide.
  • the azo compound include azobis (iso-butyronitrile) and 2,2'-azobis (2-methylbutanenitrile).
  • the reaction can be allowed to proceed even without a solvent.
  • the reaction can be performed by adding a solvent.
  • a solvent that does not react with the carbon-carbon double bond of the (meth) acrylate group or the thiol group for example, alcohols, ketones, and esters is preferable.
  • Alcohols used as solvents react with carbon-carbon double bonds and thiol groups, such as carbon-carbon double bonds, thiol groups, epoxy groups, isocyanate groups, carboxyl groups, sulfonyl groups, nitrile groups, halogen atoms, etc. Must not contain functional groups.
  • Examples of alcohols that do not contain the above functional group include methanol, ethanol, isopropyl alcohol, tertiary butanol, hexanol, propylene glycol, glycerin, and alkyl ethers and esters of ethylene glycol.
  • alcohols having a boiling point of 80 ° C. or higher are preferable because the reaction temperature can be kept high.
  • Ketones used as solvents react with carbon-carbon double bonds and thiol groups, such as carbon-carbon double bonds, thiol groups, epoxy groups, isocyanate groups, carboxyl groups, sulfonyl groups, nitrile groups, halogen atoms, etc. Must not contain functional groups.
  • Examples of the ketones that do not contain the functional group include acetone, methyl ethyl ketone, methyl isobutyl ketone, and methyl isopropyl ketone. Of these, ketones having a boiling point of 80 ° C. or higher are preferable because the reaction temperature can be kept high.
  • Esters used as solvents include carbon-carbon double bonds, thiol groups, carbon-carbon double bonds, thiol groups, epoxy groups, isocyanate groups, carboxyl groups, sulfonyl groups, nitrile groups, halogen atoms, etc. Must not contain functional groups.
  • Examples of ketones that do not contain the above functional group include ethyl acetate, butyl acetate, ethyl benzoate, and propylene glycol acetate. Of these, esters having a boiling point of 80 ° C. or higher are preferable because the reaction temperature can be kept high.
  • the reaction formula represented by the following formula 7 X represents a hydrogen atom or a methyl group
  • Y represents a residue other than X bonded to the double bond of the (meth) acryloyl group of the A component
  • Z represents a residue bonded to the thiol group of the B component.
  • both of the two carbons forming the double bond of the (meth) acrylate group of the A component are bonded to S of the thiol group.
  • the production ratio of the two products varies depending on the reaction conditions. For example, when a base catalyst such as amine is added to the reaction system as a catalyst for this reaction, a large amount of product (1) is produced, and the radical generator is produced in the reaction system. When added to, a large amount of product (2) tends to be formed. In many cases, the thioether-containing acrylic derivative after production is a mixture of products (1) and (2).
  • ⁇ Adhesion improver> By blending the thioether-containing (meth) acrylate derivative of this embodiment into a resin composition such as a paint or an adhesive, adhesion to both inorganic materials and organic materials can be improved. Therefore, it can be used as an adhesion improver as it is or after blending with a solvent or the like. In particular, by blending with a compound having a double bond such as an epoxy resin, a urethane resin, an acrylic resin, a polyimide resin, or polyacetylene, a high effect of improving adhesion can be exhibited.
  • the adhesion improving effect of the adhesion improving agent is attributed to the thioether group of the thioether-containing (meth) acrylate derivative.
  • a substrate that forms a chemical bond with a thioether group for example, an inorganic substrate such as a transition metal or an alloy thereof, a silicon compound, a phosphorus compound, a sulfur compound, or a boron compound, It is excellent in the effect of improving adhesion to an organic substance having a saturated bond (including an aromatic ring), an organic substance having a hydroxyl group or a carboxyl group, or an organic substance treated with plasma or UV ozone.
  • examples of the inorganic base material include glass, silicon, and various metals.
  • Preferred examples of the organic substrate include polyethylene terephthalate, polybutylene terephthalate, polyethylene, polypropylene, polycarbonate, polyimide, ABS resin, polyvinyl alcohol, vinyl chloride, and polyacetal.
  • the adhesion improver comprising the thioether-containing (meth) acrylate derivative as an active ingredient is highly adhesive when added in an amount of 0.1 to 80% by mass as the active ingredient relative to the resin component in the resin composition such as paint or adhesive. Can demonstrate its sexuality.
  • This adhesion improver also has the effect of increasing the flexibility of the resin by the ester group, and the resulting coating film has excellent flexibility.
  • Examples 1-1 to 1-5) First, in Examples 1-1 to 1-5, thioether-containing (meth) acrylate derivatives (composites 1 to 5) were synthesized using the following components A and B.
  • the A component and B component used are as follows.
  • Example 1-1 (Compound 1): FIG. 2960 cm ⁇ 1 : 99% T, 1733 cm ⁇ 1 : 84% T, 1690 cm ⁇ 1 : 73% T, 1459 cm ⁇ 1 : 81% T, 1351 cm ⁇ 1 : 95% T, 1243 cm ⁇ 1 : 91% T, 1158 cm ⁇ 1 : 87% T, 1007 cm ⁇ 1 : 96% T, 764 cm ⁇ 1 : 91% T
  • Example 1-2 (Compound 2): FIG. 2960 cm ⁇ 1 : 98% T, 1732 cm ⁇ 1 : 84% T, 1690 cm ⁇ 1 : 78% T, 1459 cm ⁇ 1 : 84% T, 1351 cm ⁇ 1 : 95% T, 1243 cm ⁇ 1 : 91% T, 1158 cm ⁇ 1 : 88% T, 764 cm ⁇ 1 : 93% T
  • Example 1-3 (Compound 3): FIG. 2964 cm ⁇ 1 : 99% T, 1733 cm ⁇ 1 : 84% T, 1690 cm ⁇ 1 : 73% T, 1459 cm ⁇ 1 : 81% T, 1351 cm ⁇ 1 : 95% T, 1243 cm ⁇ 1 : 91% T, 1158 cm ⁇ 1 : 87% T, 1003 cm ⁇ 1 : 96% T, 818 cm ⁇ 1 : 97% T, 764 cm ⁇ 1 : 91% T
  • Example 1-4 (Compound 4): FIG. 2925 cm ⁇ 1 : 97% T, 1737 cm ⁇ 1 : 87% T, 1690 cm ⁇ 1 : 78% T, 1459 cm ⁇ 1 : 84% T, 1351 cm ⁇ 1 : 96% T, 1243 cm ⁇ 1 : 93% T, 1158 cm ⁇ 1 : 90% T, 1003 cm ⁇ 1 : 97% T, 837 cm ⁇ 1 : 96% T, 764 cm ⁇ 1 : 92% T
  • Example 1-5 (Compound 5): FIG. 2956 cm ⁇ 1 : 99% T, 1733 cm ⁇ 1 : 86% T, 1690 cm ⁇ 1 : 76% T, 1459 cm ⁇ 1 : 83% T, 1351 cm ⁇ 1 : 95% T, 1243 cm ⁇ 1 : 92% T, 1158 cm ⁇ 1 : 88% T, 1007 cm ⁇ 1 : 97% T, 764 cm ⁇ 1 : 92% T
  • Example 1-1 (Compound 1): FIG. a: 0.9 to 1.0 ppm, b: 1.3 to 1.5 ppm, c, o: 1.5 to 1.7 ppm, e, f, g, h, m, n: 2.5 to 2. 9 ppm, d, i, j, k, l: 4.0 to 4.5 ppm
  • Example 1-2 (Compound 2): FIG. a: 0.9 to 1.0 ppm, b: 1.3 to 1.6 ppm, c, o: 1.5 to 1.7 ppm, e, f, g, h, m, n: 2.5 to 2. 9 ppm, d, i, j, k, l: 4.0 to 4.5 ppm
  • Example 1-3 (Compound 3): FIG. a, b: 0.8 to 1.1 ppm, c, o: 1.6 to 2.1 ppm, e, f, g, h, m, n: 2.5 to 3.0 ppm, d, i, j, k, l: 3.8 to 4.6 ppm
  • Example 1-4 (Compound 4): FIG. a: 0.8 to 0.9 ppm, b, c, d, e, f, g, h, i, j: 1.1 to 1.4 ppm, k, w: 1.5 to 1.7 ppm, n, m, p, o, u, v: 2.5 to 2.9 ppm, l, q, r, s, t: 4.0 to 4.5 ppm
  • Example 1-5 (Compound 5): FIG. a, e: 0.7 to 1.0 ppm, b, c, d, f: 1.1 to 1.4 ppm, q, s: 1.5 to 1.8 ppm, i, j, k, l, q, r: 2.5 to 2.9 ppm, h, m, n, o, p: 3.8 to 4.4 ppm
  • Examples 2-1 to 2-5 Comparative Examples 2-1 to 2-5)
  • the above composites 1 to 5 were added to the resin composition as an adhesion improver, and the performance was evaluated.
  • the adhesion improver when only the A component before the reaction is used as the adhesion improver, only the B component before the reaction is used, the A component and the B component before the reaction are used, and the adhesion is improved. The performance was evaluated when the agent was not used.
  • a phenol novolac type epoxy resin [manufactured by Toto Kasei Co., Ltd., YDPN638] was used.
  • the composition was applied on a PET film having a width of 25 mm [manufactured by Toray Industries, Inc., Lumirror U46-100] with a bar coater to a thickness of 100 microns, and the PET film was laminated on the opposing substrate, and then the coating was applied at 150 ° C., 1
  • the test piece for evaluation was obtained by curing under time conditions.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
PCT/JP2015/056773 2014-03-11 2015-03-09 チオエーテル含有（メタ）アクリレート誘導体、およびこれを含有する密着性向上剤 WO2015137264A1 (ja)

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KR1020157034991A KR101748067B1 (ko) 2014-03-11 2015-03-09 티오에테르 함유 (메트)아크릴레이트 유도체 및 이를 함유하는 밀착성 향상제
CN201580000256.5A CN105473561B (zh) 2014-03-11 2015-03-09 含硫醚的(甲基)丙烯酸酯衍生物及含有该衍生物的贴附性改善剂

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JP2014047230A JP6326875B2 (ja) 2014-03-11 2014-03-11 チオエーテル含有（メタ）アクリレート誘導体、およびこれを含有する密着性向上剤
JP2014-047230 2014-03-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017052948A (ja) * 2015-09-11 2017-03-16 日油株式会社 粘着剤組成物、及びこれを用いた粘着シート
EP3424933A1 (en) * 2013-06-12 2019-01-09 Shin-Etsu Chemical Co., Ltd. Thiocarbamatoalkyl-substituted 2,4,6-trioxo-1,3,5-triazines as adhesion improvers

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JP6710892B2 (ja) * 2014-09-01 2020-06-17 日油株式会社 硬化性樹脂組成物
CN105980444B (zh) * 2014-09-01 2017-12-15 日油株式会社 固化性树脂组合物
JPWO2016117385A1 (ja) * 2015-01-20 2017-10-26 日油株式会社 硬化性樹脂組成物
JP6962009B2 (ja) * 2016-12-09 2021-11-05 日油株式会社 粘着剤組成物、及びこれを用いた積層体
KR102707199B1 (ko) 2019-10-07 2024-09-13 미쓰이 가가쿠 가부시키가이샤 에틸렌·α-올레핀 공중합체 조성물 및 그 용도

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50106881A (zh) * 1974-01-30 1975-08-22
JPS6230753A (ja) * 1985-07-16 1987-02-09 ダブリユ−・ア−ル・グレイス・アンド・カンパニ− メルカプトカルボン酸を含むチオエ−テル及びその製造法
JP2008163094A (ja) * 2006-12-27 2008-07-17 Dic Corp 含フッ素組成物及び含フッ素多官能チオール
WO2012070637A1 (ja) * 2010-11-25 2012-05-31 日油株式会社 チオエーテル含有アルコキシシラン誘導体およびその用途
US20140323647A1 (en) * 2013-04-24 2014-10-30 The Board Of Regents Of The University Of Texas System Softening materials based on thiol-ene copolymers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5895715B2 (ja) * 2012-06-01 2016-03-30 日油株式会社 チオエーテル含有ウレア誘導体、およびその用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50106881A (zh) * 1974-01-30 1975-08-22
JPS6230753A (ja) * 1985-07-16 1987-02-09 ダブリユ−・ア−ル・グレイス・アンド・カンパニ− メルカプトカルボン酸を含むチオエ−テル及びその製造法
JP2008163094A (ja) * 2006-12-27 2008-07-17 Dic Corp 含フッ素組成物及び含フッ素多官能チオール
WO2012070637A1 (ja) * 2010-11-25 2012-05-31 日油株式会社 チオエーテル含有アルコキシシラン誘導体およびその用途
US20140323647A1 (en) * 2013-04-24 2014-10-30 The Board Of Regents Of The University Of Texas System Softening materials based on thiol-ene copolymers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3424933A1 (en) * 2013-06-12 2019-01-09 Shin-Etsu Chemical Co., Ltd. Thiocarbamatoalkyl-substituted 2,4,6-trioxo-1,3,5-triazines as adhesion improvers
JP2017052948A (ja) * 2015-09-11 2017-03-16 日油株式会社 粘着剤組成物、及びこれを用いた粘着シート

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TWI527802B (zh) 2016-04-01
KR101748067B1 (ko) 2017-06-15
CN105473561B (zh) 2017-09-19
TW201534592A (zh) 2015-09-16
CN105473561A (zh) 2016-04-06
KR20160006759A (ko) 2016-01-19
JP2015168679A (ja) 2015-09-28
JP6326875B2 (ja) 2018-05-23

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