WO2020111338A1 - Ruban adhésif transparent optique présentant une capacité d'absorption de différence de niveau améliorée et son procédé de fabrication - Google Patents

Ruban adhésif transparent optique présentant une capacité d'absorption de différence de niveau améliorée et son procédé de fabrication Download PDF

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Publication number
WO2020111338A1
WO2020111338A1 PCT/KR2018/015055 KR2018015055W WO2020111338A1 WO 2020111338 A1 WO2020111338 A1 WO 2020111338A1 KR 2018015055 W KR2018015055 W KR 2018015055W WO 2020111338 A1 WO2020111338 A1 WO 2020111338A1
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WO
WIPO (PCT)
Prior art keywords
adhesive tape
photoinitiator
curing
optically transparent
transparent adhesive
Prior art date
Application number
PCT/KR2018/015055
Other languages
English (en)
Korean (ko)
Inventor
이지혜
남승웅
예광남
임회득
박민수
Original Assignee
주식회사 영우
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 주식회사 영우 filed Critical 주식회사 영우
Publication of WO2020111338A1 publication Critical patent/WO2020111338A1/fr

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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
    • 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]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • 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
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid 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
    • 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
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to an optically transparent adhesive tape used in electronic devices and a method for manufacturing the same, and relates to an optically transparent adhesive tape having improved step absorption and durability by a double curing method and a method for manufacturing the same.
  • optically transparent adhesive tapes are widely used for bonding optical members used in electronic components such as liquid crystal displays and touch panels.
  • the optically transparent adhesive tape has a structure laminated to a conductive glass, a reinforcing material or a deco film, etc. via an adhesive layer coated with an adhesive composition on a film such as polyethylene terephthalate.
  • the first object of the present invention is to provide a transparent adhesive tape having improved step absorption performance in a printing section.
  • a second object of the present invention is to provide an optically transparent adhesive tape that does not deteriorate durability while improving the step absorption performance.
  • the optically transparent adhesive tape of the present invention for solving the above problems is prepared from an optically transparent adhesive composition comprising a prepolymer syrup partially polymerized with an acrylate compound and a photoinitiator, a photoinitiator for primary curing, and a photoinitiator for secondary curing.
  • the optically transparent adhesive composition is an optically transparent adhesive tape having a step absorbency that is cured by primary curing, adhered to a substrate having a step in a semi-cured state, and then completely cured by secondary curing.
  • the gel fraction after primary curing is 30 to 50%, and the gel fraction after secondary curing is 60% or more.
  • the primary curing photoinitiator is 1-hydroxy-cyclohexylphenyl-ketone (1-hydroxy-cyclohexylphenyl ketone), and the secondary curing photoinitiator is acryloyl benzophenone, acrylic It is preferably one selected from the group consisting of monoethyl benzophenone and acryloyloxy benzophenone.
  • the optically transparent adhesive composition includes 100 parts by weight of the prepolymer syrup, 0.3 to 0.9 parts by weight of a photoinitiator for primary curing, and 0.2 to 0.9 parts by weight of a photoinitiator for secondary curing.
  • the method of manufacturing the optically transparent adhesive tape of the present invention comprises the steps of preparing a prepolymer syrup partially polymerized with an acrylate-based compound and a photoinitiator; Preparing an optically transparent adhesive composition by adding and blending a photoinitiator for primary curing and a photoinitiator for secondary curing to the prepolymer syrup; First curing the optically transparent adhesive composition; And secondary curing the primary cured optically transparent adhesive composition. It characterized in that it comprises.
  • the first curing step it is preferable to irradiate a light amount of 0.8 to 1.3 J/cm 2, and in the second curing step, it is preferable to irradiate a light amount of 3 to 5 J/cm 2. .
  • the optical adhesive tape of the present invention has an excellent step absorbency and durability.
  • the optically transparent adhesive tape of the present invention is prepared from an optically transparent adhesive composition comprising a prepolymer syrup partially polymerized with an acrylate compound and a photoinitiator, a photoinitiator for primary curing and a photoinitiator for secondary curing, and the optically transparent adhesive composition
  • This is an optically transparent adhesive tape having a step absorbency that is cured by primary curing, and then adhered to a substrate having a step in a semi-cured state and then completely cured by secondary curing.
  • the optically transparent adhesive tape is excellent in durability when the gel fraction and modulus of the adhesive layer are high, but the high gel fraction and modulus are factors that weaken the step absorption performance. Therefore, in order to improve the step absorption performance of the adhesive layer, it is important to control to have an appropriate level of gel fraction and modulus.
  • in order to realize a proper gel fraction and modulus, in preparing the adhesive layer it is featured in introducing double photocuring.
  • the gel fraction of the adhesive layer is controlled to a level of 30-50% to improve the step absorption performance, and after the secondary curing, the gel fraction of the adhesive layer is 60%.
  • a photopolymerizable monomer and a photoinitiator are mixed and stirred, and then ultraviolet light is irradiated under a nitrogen atmosphere to prepare a syrup prepolymer.
  • the prepolymer syrup is usually formed by polymerization of photocurable monomers. Specifically, a monomer and a photoinitiator for forming the photocurable adhesive resin are mixed, and if necessary, an additive is added, followed by irradiation with light to partially photopolymerize to make a syrup state.
  • the optically transparent adhesive tape of the present invention can be used in a semi-cured state, and can be adhered to a substrate having a step difference of 60 to 100 ⁇ m due to excellent step absorption.
  • the semi-cured adhesive composition is second-cured to the second, and the adhesive tape is fully cured in the adhesive state on the substrate, and then the substrate And the adhesive tape are adhesive.
  • optically transparent adhesive composition according to the present invention will be described in more detail.
  • the adhesive composition of the present invention is not particularly limited as long as it is a polymer that is polymerized and crosslinked with a polymer upon light irradiation.
  • a compound containing at least one unsaturated double bond and a photopolymerization initiator may be used.
  • Preferred examples of the compound having one or more unsaturated double bonds are acrylic compounds.
  • the acrylate-based compound is 2-ethylhexyl acrylate (2-EHA), ethylhexyl methyl acrylate (EHMA), isobornyl acrylate (IBoA), isostearyl acrylate (ISTA), 4-hydroxy Butyl acrylate (4-HBA), hydroxyethyl acrylate (HEA), butyl acrylate, hexyl acrylate, n- octyl acrylate, and at least one selected from acrylate monomers including isooctyl acrylate. Can be.
  • the present invention may be subjected to a process of preparing a prepolymer in a syrup state by mixing a photoinitiator with the photopolymerizable monomer, adding an additive if necessary, and partially photopolymerizing by irradiating light.
  • the prepolymer syrup preferably has a weight average molecular weight of 1,000,000 to 3,000,000, more preferably 1,300,000 to 2,500,000, and most preferably 1,500,000 to 2,000,000.
  • weight average molecular weight is less than 1,000,000, it takes a long time for subsequent photocuring, so productivity may drop, and when it exceeds 3,000,000, it is not preferable because the mixing performance may decrease when preparing the adhesive composition.
  • the primary curing photoinitiator is 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,2,2-dimethoxy-1,2-diphenylethan-1-one , 1-hydroxy-cyclohexylphenyl-ketone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropanone-1,2,4-diethylthioxanthone, 2-ethyl
  • One or more selected from aromatic ketones of anthraquinone and phenanthrenequinone can be used, and 1-hydroxy-cyclohexylphenyl-ketone is particularly preferred.
  • the secondary curing photoinitiator may include acetophenone, benzophenone, mihila ketone, benzoin, benzyl methyl ketal, benzoyl bezoade, etc., but benzophenone is preferred, and in particular, acryloyl benzo in terms of improving durability.
  • Phenone, acryloylethyl benzophenone and acryloyloxy benzophenone are preferably one selected from the group consisting of.
  • the composition of the prepolymer syrup, the photoinitiator for primary curing and the photoinitiator for secondary curing 100 parts by weight of the prepolymer syrup, 0.3 to 0.9 parts by weight of the photoinitiator for primary curing, and the photoinitiator for secondary curing 0.2 It is preferably included in a proportion of 0.9 parts by weight. If the content of the primary curing photoinitiator is less than 0.2 parts by weight, the workability may be deteriorated, and if it exceeds 0.9 parts by weight, the step yieldability may deteriorate.
  • the secondary curing photoinitiator When the secondary curing photoinitiator is less than 0.2 parts by weight, heat resistance and workability It may fall off, and if the photoinitiator for secondary curing exceeds 0.9 parts by weight, the adhesive performance may deteriorate, which is not preferable.
  • an adhesive composition constituting the adhesive layer of the adhesive tape is prepared.
  • the adhesive composition may be started from partial polymerization by first irradiating a mixture of a photopolymerizable monomer and a photoinitiator to prepare a syrup prepolymer.
  • the primary curing photoinitiator and the secondary curing photoinitiator are added to obtain a sufficiently stirred adhesive composition.
  • the adhesive composition is applied onto a transparent film such as polyethylene terephthalate, the adhesive composition is first irradiated with light to obtain a semi-cured adhesive tape.
  • the first curing step it is preferable to irradiate a light amount of 0.8 to 1.3 J/cm 2.
  • a light amount of less than 0.8 J/cm2 sufficient photocuring may not be achieved, and when irradiating a light amount of more than 1.3 J/cm2, curing proceeds too much and the step absorption performance may be deteriorated, which is not preferable.
  • the adhesive tape After adhering the semi-cured adhesive tape on the substrate, the adhesive tape is completely cured so that the adhesive tape is adhered to the substrate, and the amount of light irradiated is preferably 3 to 5 J/cm 2.
  • the amount of light irradiated is preferably 3 to 5 J/cm 2.
  • the gel fraction of the adhesive layer is 30-50%. It is more preferable from the viewpoint of step absorbency to control the gel fraction of the adhesive layer after the primary curing to 35 to 45%.
  • the adhesive tape according to the present invention may be used for an optical member such as a touch panel or a display panel, but is not limited thereto, and may be used without particular limitation as long as it is an application requiring absorption of a printing step.
  • 2-EHA / EHMA / IBOA / HEA each using 40 parts by weight/10 parts by weight/30 parts by weight/20 parts by weight
  • photoinitiator 1-hydroxy-cyclohexylphenyl-ketone Irgacure 184
  • the acrylic polymer syrup is a prepolymer with a polymerization rate of 10% and a weight average molecular weight (Mw) of 2 million.
  • Example 1 except for changing the composition of the pressure-sensitive adhesive composition as shown in Table 1, an adhesive tape was prepared in the same manner as in Example 1.
  • the prepolymer syrup of the above preparation example 100 parts by weight of the prepolymer syrup of the above preparation example, 0.3 parts by weight of the primary photoinitiator 1-hydroxy-cyclohexylphenyl-ketone (Irgacure 184), and 0.6 parts by weight of HDDA (Hexanediol diacrylate) were added, followed by mixing the pressure-sensitive adhesive composition. Thereafter, the pressure-sensitive adhesive composition was coated on a polyethylreterphthalate film to a thickness of 150 ⁇ m. The coated adhesive composition was cured by irradiating a light amount of 3J/cm 2 using a black light bulb.
  • the primary photoinitiator 1-hydroxy-cyclohexylphenyl-ketone Irgacure 184
  • HDDA Hexanediol diacrylate
  • Example 1 except for changing the composition of the pressure-sensitive adhesive composition as shown in Table 1, an adhesive tape was prepared in the same manner as in Example 1.
  • the measurement of the gel fraction accurately measures the mass of the adhesive layer, is immersed in toluene for 24 hours, and then filtered through a 200 mesh wire mesh. Thereafter, the filtrate was dried at 100° C. for 1 hour, and the mass of the residue was accurately measured to calculate the gel fraction of the adhesive layer from the following equation.
  • the modulus was measured at 30°C using a modulus meter ARES G2.
  • the printing step was attached to a glass substrate having a thickness of 100 ⁇ m, and the step absorbency was evaluated.
  • the evaluation of the level absorbency was evaluated by the presence or absence of air bubbles or air bubbles in the adhesive film. When the level of water absorption or air bubbles is little, the level of water absorption is excellent. When a lot of or bubbles are generated, it is indicated as " ⁇ " and the results are shown in Table 2 below.
  • the adhesive tapes of the embodiments incorporating the double curing method have much better step absorbency and durability than Comparative Example 1 which is not.
  • Comparative Examples 2 and 3 in which the composition of the secondary photoinitiator was 1.0 part by weight, showed a tendency to drop in step absorbency compared to the adhesive tape of the Examples.
  • the adhesive composition constituting the adhesive tape of the present invention has a photoinitiator content of 0.5 to 0.7 parts by weight based on 100 parts by weight of the prepolymer syrup. It can be seen that it is the most preferable range.

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

Abstract

La présente invention concerne un ruban adhésif transparent optique. Le ruban adhésif transparent optique est préparé à partir d'une composition adhésive transparente optique comprenant : un sirop de prépolymère dans lequel un composé à base d'acrylate et un photo-initiateur sont partiellement polymérisés ; un photo-initiateur de durcissement primaire ; et un photo-initiateur de durcissement secondaire. La composition adhésive transparente optique est premièrement durcie pour être maintenue dans un état semi-durci. La composition adhésive transparente optique dans un état semi-durci est appliquée sur un substrat présentant un épaulement puis complètement durcie par durcissement secondaire, le ruban adhésif transparent optique obtenu ayant de ce fait une capacité d'absorption de différence de niveau. Le ruban adhésif optique de la présente invention présente une excellente capacité d'absorption de différence de niveau et une excellente durabilité.
PCT/KR2018/015055 2018-11-30 2018-11-30 Ruban adhésif transparent optique présentant une capacité d'absorption de différence de niveau améliorée et son procédé de fabrication WO2020111338A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2018-0151594 2018-11-30
KR1020180151594A KR102154998B1 (ko) 2018-11-30 2018-11-30 단차 흡수성이 향상된 광학 투명 점착 테이프 및 이의 제조방법

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WO2020111338A1 true WO2020111338A1 (fr) 2020-06-04

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WO (1) WO2020111338A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130130927A (ko) * 2012-05-23 2013-12-03 동우 화인켐 주식회사 점착제 조성물 및 점착제층
KR20160015474A (ko) * 2014-07-30 2016-02-15 (주)엘지하우시스 광경화성 점접착제 조성물, 점접착 필름 및 점접착 필름의 제조 방법
KR20160062305A (ko) * 2014-11-24 2016-06-02 삼성디스플레이 주식회사 점착제 조성물 및 표시장치
KR20170082190A (ko) * 2016-01-05 2017-07-14 주식회사 엘지화학 3층 구조의 반경화형 광학 점착 필름
KR20170103079A (ko) * 2016-03-02 2017-09-13 주식회사 엘지화학 광학용 점착 조성물 및 광학용 점착 시트

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130130927A (ko) * 2012-05-23 2013-12-03 동우 화인켐 주식회사 점착제 조성물 및 점착제층
KR20160015474A (ko) * 2014-07-30 2016-02-15 (주)엘지하우시스 광경화성 점접착제 조성물, 점접착 필름 및 점접착 필름의 제조 방법
KR20160062305A (ko) * 2014-11-24 2016-06-02 삼성디스플레이 주식회사 점착제 조성물 및 표시장치
KR20170082190A (ko) * 2016-01-05 2017-07-14 주식회사 엘지화학 3층 구조의 반경화형 광학 점착 필름
KR20170103079A (ko) * 2016-03-02 2017-09-13 주식회사 엘지화학 광학용 점착 조성물 및 광학용 점착 시트

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KR102154998B1 (ko) 2020-09-14
KR20200065285A (ko) 2020-06-09

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