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WO2015009003A1 - Composition d'adhésif - Google Patents

Composition d'adhésif Download PDF

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Publication number
WO2015009003A1
WO2015009003A1 PCT/KR2014/006341 KR2014006341W WO2015009003A1 WO 2015009003 A1 WO2015009003 A1 WO 2015009003A1 KR 2014006341 W KR2014006341 W KR 2014006341W WO 2015009003 A1 WO2015009003 A1 WO 2015009003A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
meth
parts
acrylate
adhesive composition
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2014/006341
Other languages
English (en)
Korean (ko)
Inventor
최한영
유지희
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongwoo Fine Chem Co Ltd
Original Assignee
Dongwoo Fine Chem Co Ltd
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
Priority claimed from KR20140050241A external-priority patent/KR20150010567A/ko
Application filed by Dongwoo Fine Chem Co Ltd filed Critical Dongwoo Fine Chem Co Ltd
Publication of WO2015009003A1 publication Critical patent/WO2015009003A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • 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

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition excellent in antistatic properties, liquid stability and durability, shortened curing period.
  • a liquid crystal display device In general, a liquid crystal display device (LCD) is provided with a liquid crystal cell and a polarizing plate containing a liquid crystal, and an appropriate pressure-sensitive adhesive layer for bonding them is used.
  • the pressure sensitive adhesive is often used an acrylic pressure sensitive adhesive based on an acrylic copolymer having excellent adhesiveness and transparency.
  • peeling the release film from the pressure-sensitive adhesive layer generates static electricity.
  • the generated static electricity affects the alignment of the liquid crystal and causes defects or flows between the liquid crystal cell and the adhesive due to electrostatic attraction. It causes contamination by foreign objects.
  • an ionic antistatic agent is mixed and used in the pressure-sensitive adhesive composition, but a bleed out phenomenon that precipitates due to the surface migration of the ionic antistatic agent may cause lifting, bubbles, and peeling. In particular, this problem may be exacerbated when exposed to a high temperature or high temperature and high humidity environment.
  • a pressure-sensitive adhesive composition containing an acrylic copolymer copolymerized using a monomer containing an alkylene oxide group has been proposed (Korean Patent Publication Nos. 2012-0073093 and 2009-0055576).
  • the acrylic copolymer may have a problem of viscosity increase due to change over time, so that storage after mass production is difficult.
  • the pressure-sensitive adhesive composition also acts as an important factor in the curing period that affects productivity, warehouse capacity, inventory management and emergency shipment response.
  • the present invention relates to a pressure-sensitive adhesive composition that can simultaneously improve antistatic properties and durability without fear of viscosity increase due to changes over time, and can shorten the curing period without using a catalyst for crosslinking.
  • the present invention relates to 1 to 10 parts by weight of a (meth) acrylate monomer having a carboxyl group, and a linear or cyclic alkyl group having 4 or more carbon atoms in which a hydroxy group is substituted (meth)
  • the acrylate monomer having a linear or cyclic alkyl group having 4 or more carbon atoms in which the hydroxy group is substituted is 4-hydroxybutyl acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, and It may be one or more selected from the group consisting of.
  • the monomer used for manufacture of the said acryl-type copolymer may further contain the (meth) acrylate type monomer which has an aromatic ring.
  • the antistatic agent may be a fluorine-containing anion.
  • the fluorine-containing anion is OTF ( ), TFSI ( ) Or FSI ( May be).
  • the acrylic copolymer is 1 to 88 parts by weight of (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, and 2) 1 to 10 parts by weight of (meth) acrylate monomer having a carboxyl group, based on 100 parts by weight of the total monomers. And 3) a monomer including 0.1 to 2 parts by weight of a (meth) acrylate-based monomer having a linear or cyclic alkyl group having 4 or more carbon atoms in which a hydroxy group is substituted.
  • the pressure-sensitive adhesive composition has a curing period of 48 hours or less at the time of no change over time at 23 °C, 65% RH, the viscosity change rate before and after leaving for 24 hours at room temperature may be less than 50%.
  • the pressure-sensitive adhesive composition of the present invention can improve the antistatic properties and durability at the same time, there is an advantage that there is no fear of deterioration of physical properties due to changes over time (high temperature or high temperature and high humidity environment changes).
  • the pressure-sensitive adhesive composition of the present invention is significantly shortened to 48 hours or less, preferably 36 hours or less, compared to the conventional, so that the use of excess additives used to shorten the curing period is usually suppressed, resulting in clogging of equipment and the like. There is an advantage to ameliorate the same problem.
  • the present invention relates to a pressure-sensitive adhesive composition excellent in antistatic properties, liquid stability and durability, shortened curing period.
  • the pressure-sensitive adhesive composition of the present invention has a (meth) acrylate having 1 to 10 parts by weight of a (meth) acrylate monomer having a carboxyl group and a linear or cyclic alkyl group having 4 or more carbon atoms substituted with a hydroxy group, based on 100 parts by weight of the total monomers. It contains an acrylic copolymer prepared by copolymerizing monomers containing 0.1 to 2 parts by weight of the monomer, a trifunctional or higher tolylene diisocyanate-based crosslinking agent, and an ionic antistatic agent having Na + or K + ions.
  • the (meth) acrylate-based monomer having a carboxyl group inhibits the bleed out phenomenon in which the ionic antistatic agent moves to the surface and precipitates, and serves to improve durability by improving adhesion to glass,
  • the (meth) acrylate monomer having a hydroxyl group serves to increase crosslinking reaction and shorten curing of the pressure-sensitive adhesive composition.
  • Na + or K + ions of the ionic antistatic agent serves to coordinate the hydroxy group, thereby inhibiting the reaction between the hydroxy group and the isocyanate to improve the crude liquid stability of the pressure-sensitive adhesive composition.
  • the trifunctional or higher tolylene diisocyanate-based crosslinking agent is an aromatic isocyanate having a high reactivity with the hydroxy group of the (meth) acrylate monomer having a hydroxy group, and thus serves to shorten the curing period of the pressure-sensitive adhesive composition.
  • the present invention is a linear or more than 4 carbon atoms substituted with a (meth) acrylate monomer having a carboxyl group and a hydroxy group in the monomer for producing an acrylic copolymer in order to simultaneously improve the antistatic properties, durability, curing period and crude liquid stability
  • a (meth) acrylate monomer having a cyclic alkyl group a trifunctional or higher tolylene diisocyanate-based crosslinking agent, and an ionic antistatic agent having Na + or K + ions. It is characterized by optimizing the component mixing ratio of the monomers.
  • the acrylic copolymer of the present invention is 88 to 98 parts by weight of a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and 1 to 10 parts by weight of a (meth) acrylate monomer having a carboxyl group, based on 100 parts by weight of the total monomers. And a monomer comprising 0.1 to 2 parts by weight of a (meth) acrylate monomer having a linear or cyclic alkyl group having 4 or more carbon atoms substituted with a hydroxy group.
  • the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms is methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, n-butyl (meth) acryl Late, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) Acrylate, isopropyl (meth) acrylate, pentyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, la Usyl (meth) acrylate
  • the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms may contain 88 to 98 parts by weight based on 100 parts by weight of the total monomers. If the content is less than 88 parts by weight, the adhesive force may not be sufficient, and if it exceeds 98 parts by weight, the cohesion may be reduced.
  • (meth) acrylate monomer having a carboxyl group acrylic acid or methacrylic acid may be used.
  • the (meth) acrylate monomer having such a carboxyl group is preferably contained 1 to 10 parts by weight based on 100 parts by weight of the total monomers.
  • the content is less than 1 part by weight, the effect of suppressing the bleed out phenomenon of the ionic antistatic agent may be insignificant and the durability may be reduced, or as a catalyst of the crosslinking reaction, it may be difficult to secure a curing shortening effect.
  • the crude liquid stability of the adhesive composition may be lowered due to excessive crosslinking reaction.
  • the (meth) acrylate monomer having a linear or cyclic alkyl group having 4 or more carbon atoms in which the hydroxy group is substituted is 4-hydroxybutyl (meth) acrylate, 6-hydroxypexyl (meth) acrylate, 8-hydroxyoctyl (Meth) acrylate and One or more selected from the group consisting of can be used. Considering the curing rate, 4-hydroxybutyl acrylate or Is preferred
  • the (meth) acrylate monomer having a linear or cyclic alkyl group having 4 or more carbon atoms substituted with such a hydroxy group is preferably contained in an amount of 0.1 to 2 parts by weight based on 100 parts by weight of the total monomers. If the content is less than 0.1 parts by weight, the curing period may be shortened, and when it exceeds 2 parts by weight, the crude liquid stability may be lowered due to excessive crosslinking reaction.
  • the monomer for preparing the acrylic copolymer of the present invention may further contain a (meth) acrylate monomer having an aromatic ring to prevent light leakage.
  • Examples of the (meth) acrylate monomer having an aromatic ring include 2-ethylphenoxy (meth) acrylate, 2-ethylthiophenyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, 2- Phenylethyl (meth) acrylate, 3-phenylpropyl (meth) acrylate, 4-phenylbutyl (meth) acrylate, 2-2-methylphenylethyl (meth) acrylate, 2-3-methylphenylethyl (meth) acrylic Rate, 2-4-methylphenylethyl (meth) acrylate, 2- (4-propylphenyl) ethyl (meth) acrylate, 2- (4- (1-methylethyl) phenyl) ethyl (meth) acrylate, 2 -(4-methoxyphenyl) ethyl (meth) acrylate, 2- (4-
  • the (meth) acrylate monomer having such an aromatic ring is a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, a (meth) acrylate monomer having a carboxyl group, and a linear or cyclic group having 4 or more carbon atoms substituted with a hydroxy group.
  • the total total amount of the (meth) acrylate monomer having an alkyl group is 100 parts by weight, it is preferable to add 6 to 12 parts by weight. When the amount is less than 6 parts by weight or more than 12 parts by weight may cause light leakage.
  • the production method of the copolymer is not particularly limited, and may be prepared using a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which are commonly used in the art, and solution polymerization is preferable.
  • a solvent, a polymerization initiator, a chain transfer agent for molecular weight control, and the like, which are usually used in the polymerization may be used.
  • the copolymer has a weight average molecular weight (polystyrene equivalent, Mw) measured by gel permeation chromatography (GPC) of 50,000 to 2 million, preferably 400,000 to 2 million.
  • Mw polystyrene equivalent
  • GPC gel permeation chromatography
  • a crosslinking agent can improve adhesiveness and durability, and can maintain the reliability and shape of an adhesive at high temperature.
  • the present invention considers the reactivity, durability and light leakage of the (meth) acrylate-based monomer having a carboxyl group and the (meth) acrylate-based monomer having a linear or cyclic alkyl group having 4 or more carbon atoms substituted with a hydroxy group. If it is a trifunctional or more than trifunctional tolylene diisocyanate type crosslinking agent is preferable.
  • Examples of the trifunctional or higher tolylene diisocyanate-based crosslinking agent include trimethylolpropane adducts of tolylene diisocyanate (Japanese urethane company, coronate-L) and tolylene diisocyanate trimer (Aekyung Chemical Company, AKNATE TR-50). .
  • the trifunctional or higher tolylene diisocyanate-based crosslinking agent may be contained in an amount of 0.1 to 1 parts by weight based on 100 parts by weight of the total monomers. If the content is less than 0.1 parts by weight, the cohesion force becomes small due to insufficient crosslinking degree, causing durability deterioration such as lifting and damaging property. If the content is more than 1.0 parts by weight, it may be difficult to secure the stability of the solution.
  • the present invention includes an ionic antistatic agent having Na + or K + ions which can lower the reaction rate of the hydroxy group and the isocyanate group of the acrylic copolymer to improve the crude liquid stability.
  • a fluorine-containing anion or an iodine ion may be used as the anion of the ionic antistatic agent.
  • the fluorine-containing anion is OTF ( ), TFSI ( ) Or FSI ( ) And the like.
  • Such an ionic antistatic agent may contain 0.5 to 5 parts by weight based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.5 parts by weight of crude liquid stability may be insufficient, if it exceeds 5 parts by weight it may be difficult to secure durability.
  • the pressure-sensitive adhesive composition of the present invention may further contain a silane coupling agent.
  • the kind of the silane coupling agent is not particularly limited, and for example, vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxy Propyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-metha Krilloxypropyl triethoxysilane, 3-methacryloxypropyl trimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyl diethoxysilane, 3-acryloxypropyl trimethoxysilane , N-2- (aminoethyl) -3-aminopropylmethyld
  • the pressure-sensitive adhesive composition is a tackifying resin, antioxidant, leveling agent, surface lubricant, dye, pigment, antifoaming agent, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, etc. It may further contain additives such as fillers and light stabilizers.
  • Such additives can be appropriately adjusted in a range not impairing the effects of the present invention.
  • the pressure-sensitive adhesive composition of the present invention can be used as a pressure-sensitive adhesive for polarizing plates and a surface protective film for bonding to liquid crystal cells.
  • it can be used as a general commercial adhesive sheet product as well as a protective film, a reflective sheet, a structural adhesive sheet, a photographic adhesive sheet, a lane marking adhesive sheet, an optical adhesive product, an adhesive for electronic parts, and the like.
  • Nitrogen gas was refluxed and the monomer mixture consisting of the composition of Table 1 was added to a 1 L reactor equipped with a cooling device to facilitate temperature control, and then 100 parts by weight of ethyl acetate was added as a solvent. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 78 °C. After the mixture was uniformed, 0.03 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 8 hours to prepare an acrylic copolymer having a weight average molecular weight of about 780,000.
  • AIBN azobisisobutyronitrile
  • the pressure-sensitive adhesive composition prepared above was applied on a release film coated with a silicone release agent to have a thickness of 25 ⁇ m, and dried at 100 ° C. for 1 minute to form an adhesive layer.
  • An adhesive sheet was prepared by laminating another release film thereon.
  • the pressure-sensitive adhesive layer was laminated on an iodine-based polarizing plate having a thickness of 185 ⁇ m by adhesive processing to prepare a polarizing plate with pressure-sensitive adhesive.
  • the prepared polarizing plate was stored for 20 days under conditions of 23 degreeC and 60% RH.
  • the gel fraction was measured by the following method on a daily basis, and the gel fraction was no longer increased, that is, the curing period was measured.
  • the adhesive layer of an adhesive sheet is affixed on the fixed 250 mesh wire mesh (100 mm x 100 mm), and it wraps so that a gel powder may not leak.
  • the wire mesh is immersed in ethyl acetate solution for 3 days.
  • the immersed wire mesh is taken out, washed with a small amount of ethyl acetate solution, dried at 120 ° C. for 24 hours, and weighed.
  • the gel fraction was calculated by the following equation 1 using the measured weight. Curing periods were determined based on the time when the value of the calculated gel fraction was in the range of 70 to 80% and there was no change over time.
  • A is the weight of the wire mesh (g)
  • B is the weight of the wire mesh with the adhesive layer (BA: adhesive weight, g)
  • C is the weight of the dried wire mesh after immersion (CA: weight of the gelled resin, g )being].
  • the prepared pressure-sensitive adhesive polarizing plate was cut to a size of 90 mm x 170 mm, the release film was peeled off, and the specimens were prepared by attaching the optical absorption axis perpendicular to both surfaces of the glass substrate (110 mm x 190 mm x 0.7 mm).
  • the applied pressure was 5kg / cm2 and the clean room work so as not to generate bubbles or foreign matter.
  • the heat resistance characteristics were observed whether bubbles or peeling occurred after 1000 hours at 80 °C temperature, and the heat-resistant characteristics were bubbles or peeling after 1000 hours at 60 °C temperature and 90% RH conditions Was observed. At this time, it was observed after leaving for 24 hours at room temperature immediately before evaluating the state of the specimen.
  • the surface specific resistance was used (MCP-HT450 / MITSUBISHI CHEMICAL), Probe (URS, UR100), Probe Checker (for URS, UR 100).
  • the pressure-sensitive adhesive composition of Examples 1 to 18 according to the present invention has a curing period of 12 to 36 hours compared to Comparative Examples 1 to 12, and can improve antistatic properties and durability at the same time, change over time It was confirmed that there is no fear of deterioration of physical properties due to (high temperature or high temperature and high humidity environment changes).

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

Abstract

La présente invention concerne une composition d'adhésif et, plus précisément, une composition d'adhésif qui permet d'améliorer à la fois les propriétés antistatiques et la durabilité, ne pose aucun problème en ce qui concerne l'altération des propriétés physiques selon le changement au cours du temps (changement d'environnement chaud ou chaud et humide), et raccourcit le temps de durcissement, par le fait qu'elle contient un copolymère à base d'acryle préparé par copolymérisation, sur la base de 100 parties en poids des monomères totaux, de monomères comprenant 1 à 10 parties en poids d'un monomère à base de (méth)acrylate ayant un groupe carboxyle, et 0,1 à 2 parties en poids d'un monomère à base de (méth)acrylate ayant un groupe alkyle linéaire ou cyclique qui est substitué par un groupe hydroxyle et qui contient 4 atomes de carbone ou plus ; un agent de réticulation à base de diisocyanate de tolylène trifonctionnel ou de fonctionnalité supérieure ; un agent ionique antistatique contenant du Na+ ou K+.
PCT/KR2014/006341 2013-07-19 2014-07-15 Composition d'adhésif Ceased WO2015009003A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2013-0085358 2013-07-19
KR20130085358 2013-07-19
KR10-2014-0050241 2014-04-25
KR20140050241A KR20150010567A (ko) 2013-07-19 2014-04-25 점착제 조성물

Publications (1)

Publication Number Publication Date
WO2015009003A1 true WO2015009003A1 (fr) 2015-01-22

Family

ID=52346396

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/006341 Ceased WO2015009003A1 (fr) 2013-07-19 2014-07-15 Composition d'adhésif

Country Status (1)

Country Link
WO (1) WO2015009003A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010275524A (ja) * 2009-04-30 2010-12-09 Nitto Denko Corp 光学フィルム用粘着剤組成物、光学フィルム用粘着剤層、粘着型光学フィルムおよび画像表示装置
KR20110098691A (ko) * 2010-02-26 2011-09-01 주식회사 엘지화학 점착제 조성물
KR20120137266A (ko) * 2011-06-10 2012-12-20 동우 화인켐 주식회사 점착제 조성물, 이를 포함하는 편광판 및 액정표시장치
JP2013010838A (ja) * 2011-06-28 2013-01-17 Lintec Corp 粘着性組成物、粘着剤および粘着シート
WO2013069870A1 (fr) * 2011-11-07 2013-05-16 제일모직 주식회사 Composition adhésive durcie par uv, film adhésif durci par uv la comprenant, dispositif d'affichage la comprenant et procédé d'assemblage de module l'utilisant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010275524A (ja) * 2009-04-30 2010-12-09 Nitto Denko Corp 光学フィルム用粘着剤組成物、光学フィルム用粘着剤層、粘着型光学フィルムおよび画像表示装置
KR20110098691A (ko) * 2010-02-26 2011-09-01 주식회사 엘지화학 점착제 조성물
KR20120137266A (ko) * 2011-06-10 2012-12-20 동우 화인켐 주식회사 점착제 조성물, 이를 포함하는 편광판 및 액정표시장치
JP2013010838A (ja) * 2011-06-28 2013-01-17 Lintec Corp 粘着性組成物、粘着剤および粘着シート
WO2013069870A1 (fr) * 2011-11-07 2013-05-16 제일모직 주식회사 Composition adhésive durcie par uv, film adhésif durci par uv la comprenant, dispositif d'affichage la comprenant et procédé d'assemblage de module l'utilisant

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