WO2019073869A1 - Résine et composition adhésive - Google Patents

Résine et composition adhésive Download PDF

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Publication number
WO2019073869A1
WO2019073869A1 PCT/JP2018/036991 JP2018036991W WO2019073869A1 WO 2019073869 A1 WO2019073869 A1 WO 2019073869A1 JP 2018036991 W JP2018036991 W JP 2018036991W WO 2019073869 A1 WO2019073869 A1 WO 2019073869A1
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WO
WIPO (PCT)
Prior art keywords
group
resin
formula
meth
carbon atoms
Prior art date
Application number
PCT/JP2018/036991
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English (en)
Japanese (ja)
Inventor
悠司 淺津
昭一 小澤
国見　信孝
Original Assignee
住友化学株式会社
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 住友化学株式会社 filed Critical 住友化学株式会社
Priority to CN201880066262.4A priority Critical patent/CN111201252A/zh
Priority to KR1020207004690A priority patent/KR20200067832A/ko
Publication of WO2019073869A1 publication Critical patent/WO2019073869A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/02—Physical, chemical or physicochemical properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/08—Anhydrides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/02—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonates or saturated polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • the structural unit derived from the compound represented by formula (I) is preferably a structural unit derived from the compound represented by formula (II).
  • R 11 , R 12 , R 13 , R 14 and R 15 are each independently a hydrogen atom or an aliphatic hydrocarbon having 1 to 25 carbon atoms which may have a substituent] Group, an aromatic hydrocarbon group having 6 to 15 carbon atoms which may have a substituent, or a heterocyclic group, and -CH 2- contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group is -NR 11A- , -SO 2- , -CO-, -O- or -S- may be substituted.
  • the structural unit selected from the structural units described in Group A is preferably a structural unit derived from (meth) acrylic acid ester.
  • the structural unit derived from the (meth) acrylic acid ester is preferably a (meth) acrylic acid alkyl ester and a (meth) acrylic acid alkyl ester having a hydroxy group.
  • acryloyl morpholine As a monomer having a heterocyclic group, acryloyl morpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, vinylpyridine, tetrahydrofurfuryl (meth) acrylate, caprolactone modified tetrahydrofurfuryl acrylate, 3,4-epoxycyclohexylmethyl Examples include (meth) acrylate, glycidyl (meth) acrylate, 2,5-dihydrofuran and the like.
  • the structural unit (aa) other than the structural unit having a merocyanine structure and the structural unit selected from group A is preferably a monomer having a carboxyl group.
  • VAC film (trade name; film of perfect biaxial orientation type) sold by Sumitomo Chemical Co., Ltd., "new VAC film” sold by Sumitomo Chemical Co., Ltd. Trade name; biaxially oriented film) and the like.
  • Example 1 Synthesis of photoselective absorbing compound (1) having a polymerizable group and a merocyanine structure
  • a 300 mL four-necked flask equipped with a Dimroth condenser and a thermometer is a nitrogen atmosphere, 10 parts of 2-hydroxyethyl acrylate, 8.1 parts of cyanoacetic acid, and 1.1 parts of N, N-dimethyl-4-aminopyridine Then, 0.95 parts of dibutylhydroxytoluene and 50 parts of toluene were charged, and the mixture was stirred with a magnetic stirrer.
  • the obtained resin (A-1) having a merocyanine structure had a polystyrene-reduced weight average molecular weight Mw of 500,000 and a Mw / Mn of 7.5 as measured by GPC. Let this be a resin (A-1).
  • the glass transition temperature by DSC was -48.4 ° C.
  • a total of a solution obtained by dissolving 0.4 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added to the obtained mixture.
  • the resulting mixture is maintained at 60 ° C. for 1 hour, then ethyl acetate is continuously added to the reaction vessel at an addition rate of 17.3 parts / hr while maintaining the internal temperature at 50 to 70 ° C., and the concentration of acrylic resin is When 35% was reached, the addition of ethyl acetate was stopped, and the internal temperature was kept at 50 to 70 ° C. until 12 hours had elapsed from the start of the addition of ethyl acetate.
  • a 2-butanone solution (56.0 g / L) of BONASORB UA-3911 is placed in a 1 cm quartz cell, and the quartz cell is set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the double beam method is used. Absorbance was measured in the wavelength range of 1 nm step 300 to 800 nm.
  • the obtained UVA-02 had an ⁇ (405) of 93 L / (g ⁇ cm) and an ⁇ (440) of 1.3 L / (g ⁇ cm).
  • a polyacrylate compound leveling agent; BYK-361N manufactured by BYK-Chemie
  • the polymerizable liquid crystal compound A was synthesized by the method described in JP-A-2010-31223.
  • the maximum absorption wavelength ⁇ max (LC) of the polymerizable liquid crystal compound A was 350 nm.
  • a coating liquid comprising the composition A containing the polymerizable liquid crystal compound obtained in (iv) is applied onto the alignment film using a bar coater, and dried at 120 ° C. for 1 minute, and then a high pressure mercury lamp
  • the ultraviolet ray is irradiated from the surface side to which the composition containing the polymerizable liquid crystal compound is applied using (Unicure VB-15201BY-A, manufactured by Ushio Inc.) (Integrated light quantity at a wavelength of 313 nm in a nitrogen atmosphere: 500 mJ / cm 2 )
  • Example 9 Preparation of Optical Laminate (1)
  • the pressure-sensitive adhesive layer (1) was attached to the surface of the cycloolefin resin film of the polarizing plate prepared in (ii) above, and the separator was peeled off. Furthermore, the surface of the pressure-sensitive adhesive layer (1) from which the separator was peeled off was bonded to the surface opposite to the COP surface of the optically anisotropic layer prepared in (V), and the COP was peeled off.
  • the separator-attached pressure-sensitive adhesive layer (5) was bonded to the surface of the optically anisotropic layer from which COP was peeled, to obtain an optical laminate (1).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polarising Elements (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Laminated Bodies (AREA)

Abstract

La présente invention concerne une résine (A) qui présente une température de transition vitreuse inférieure ou égale à 40 °C, tout en contenant un motif structural qui possède une structure mérocyanine ; une composition adhésive qui contient cette résine (A) ; et un stratifié optique qui comprend un film optique et une couche adhésive qui est formée à partir de cette composition adhésive qui contient la résine (A).
PCT/JP2018/036991 2017-10-13 2018-10-03 Résine et composition adhésive WO2019073869A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201880066262.4A CN111201252A (zh) 2017-10-13 2018-10-03 树脂和粘合剂组合物
KR1020207004690A KR20200067832A (ko) 2017-10-13 2018-10-03 수지 및 점착제 조성물

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2017199262 2017-10-13
JP2017-199262 2017-10-13
JP2017238352 2017-12-13
JP2017-238352 2017-12-13

Publications (1)

Publication Number Publication Date
WO2019073869A1 true WO2019073869A1 (fr) 2019-04-18

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PCT/JP2018/036991 WO2019073869A1 (fr) 2017-10-13 2018-10-03 Résine et composition adhésive

Country Status (5)

Country Link
JP (1) JP2019090005A (fr)
KR (1) KR20200067832A (fr)
CN (1) CN111201252A (fr)
TW (1) TW201927988A (fr)
WO (1) WO2019073869A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021172179A1 (fr) * 2020-02-28 2021-09-02 コニカミノルタ株式会社 Film optique, plaque de polarisation et dispositif d'affichage d'images à électroluminescence organique
CN114502687A (zh) * 2019-10-11 2022-05-13 住友化学株式会社 粘合剂组合物
CN115052857A (zh) * 2020-02-14 2022-09-13 住友化学株式会社 化合物
JP7456224B2 (ja) 2019-03-28 2024-03-27 住友化学株式会社 粘着剤組成物

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220081987A (ko) * 2019-10-11 2022-06-16 스미또모 가가꾸 가부시키가이샤 점착제 조성물
JP2021099478A (ja) * 2019-12-23 2021-07-01 住友化学株式会社 光学積層体および画像表示装置
JP2021099477A (ja) * 2019-12-23 2021-07-01 住友化学株式会社 光学積層体および画像表示装置
CN113603814B (zh) * 2021-08-23 2022-05-13 无锡安睿驰科技有限公司 一种修复轮胎气密层的方法

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JPS62260152A (ja) * 1986-05-06 1987-11-12 Konika Corp 色素画像の光堅牢性が優れた熱転写材料における受像要素
US4943519A (en) * 1985-01-19 1990-07-24 Agfa-Gevaert Aktiengesellschaft Light sensitive, stabilized photographic recording material
JPH0784335A (ja) * 1993-09-16 1995-03-31 Konica Corp ハロゲン化銀写真感光材料
JP2006002069A (ja) * 2004-06-18 2006-01-05 Hayashibara Biochem Lab Inc メロシアニン色素共重合体及びその用途
JP2006521220A (ja) * 2003-03-25 2006-09-21 ランクセス ドイチュラント ゲゼルシャフト ミット ベシュレンクテル ハフツング 情報層中にポリマー網目を含有する光学データ媒体
WO2017043241A1 (fr) * 2015-09-07 2017-03-16 綜研化学株式会社 Procédé de production de polymère (méth)acrylique et procédé de production de couche adhésive

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IT1206995B (it) * 1979-10-12 1989-05-17 Minnesota Mining & Mfg Assorbenti ultravioletti polimerici materiale fotografico che li contiene e metodo per introdurli in detto materiale fotografico
JPS5990844A (ja) * 1982-11-16 1984-05-25 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPH0485531A (ja) * 1990-07-28 1992-03-18 Konica Corp ハロゲン化銀写真感光材料
JP2005281339A (ja) * 2004-03-26 2005-10-13 Nippon Shokubai Co Ltd 樹脂粒子分散体、その製造方法、およびその用途
CN105518092B (zh) * 2013-06-21 2019-04-23 日东电工株式会社 带隔膜的粘合剂层及其制造方法、带有带隔膜的粘合剂层的偏光膜及其制造方法、以及图像显示装置
JP2017048340A (ja) * 2015-09-04 2017-03-09 日本化薬株式会社 光学用粘着剤組成物、並びにこれを用いた粘着剤層及び粘着型光学フィルム
JP6088019B2 (ja) * 2015-10-01 2017-03-01 住友化学株式会社 光学積層体及び液晶表示装置

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58178351A (ja) * 1982-04-14 1983-10-19 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
US4943519A (en) * 1985-01-19 1990-07-24 Agfa-Gevaert Aktiengesellschaft Light sensitive, stabilized photographic recording material
JPS62260152A (ja) * 1986-05-06 1987-11-12 Konika Corp 色素画像の光堅牢性が優れた熱転写材料における受像要素
JPH0784335A (ja) * 1993-09-16 1995-03-31 Konica Corp ハロゲン化銀写真感光材料
JP2006521220A (ja) * 2003-03-25 2006-09-21 ランクセス ドイチュラント ゲゼルシャフト ミット ベシュレンクテル ハフツング 情報層中にポリマー網目を含有する光学データ媒体
JP2006002069A (ja) * 2004-06-18 2006-01-05 Hayashibara Biochem Lab Inc メロシアニン色素共重合体及びその用途
WO2017043241A1 (fr) * 2015-09-07 2017-03-16 綜研化学株式会社 Procédé de production de polymère (méth)acrylique et procédé de production de couche adhésive

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7456224B2 (ja) 2019-03-28 2024-03-27 住友化学株式会社 粘着剤組成物
CN114502687A (zh) * 2019-10-11 2022-05-13 住友化学株式会社 粘合剂组合物
CN115052857A (zh) * 2020-02-14 2022-09-13 住友化学株式会社 化合物
WO2021172179A1 (fr) * 2020-02-28 2021-09-02 コニカミノルタ株式会社 Film optique, plaque de polarisation et dispositif d'affichage d'images à électroluminescence organique

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Publication number Publication date
TW201927988A (zh) 2019-07-16
JP2019090005A (ja) 2019-06-13
CN111201252A (zh) 2020-05-26
KR20200067832A (ko) 2020-06-12

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