WO1997010284A1 - Composition adhesive aqueuse, film adhesif et son procede de production - Google Patents

Composition adhesive aqueuse, film adhesif et son procede de production Download PDF

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Publication number
WO1997010284A1
WO1997010284A1 PCT/US1996/012869 US9612869W WO9710284A1 WO 1997010284 A1 WO1997010284 A1 WO 1997010284A1 US 9612869 W US9612869 W US 9612869W WO 9710284 A1 WO9710284 A1 WO 9710284A1
Authority
WO
WIPO (PCT)
Prior art keywords
adhesive
ofthe
adhesive layer
film
adhesive composition
Prior art date
Application number
PCT/US1996/012869
Other languages
English (en)
Inventor
Hidetoshi Abe
Original Assignee
Minnesota Mining And Manufacturing Company
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 Minnesota Mining And Manufacturing Company filed Critical Minnesota Mining And Manufacturing Company
Priority to AU67676/96A priority Critical patent/AU6767696A/en
Priority to BR9606645A priority patent/BR9606645A/pt
Priority to EP96928081A priority patent/EP0791030A1/fr
Publication of WO1997010284A1 publication Critical patent/WO1997010284A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/095—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • 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]

Definitions

  • the present invention relates to an aqueous adhesive composition More particularly, it relates to an aqueous adhesive composition which is suitable for producing products having an adhesive layer, such as adhesive film, etc
  • the present invention relates to an adhesive film having an adhesive layer formed from the above aqueous adhesive composition, and a process for producing the same
  • an adhesive layer is provided on at least one surface of a substrate (hereinafter referred to as an "adhesive film", sometimes), such as adhesive film (e g , graphic film, etc ), adhesive tape (e.g , mending tape, etc ), marking material, etc
  • an aqueous adhesive composition containing a water-soluble or water-dispersible polymer as an adhesive component has hitherto been used as a coating solution for forming the adhesive layer thereof
  • the process for producing these products include the following (i) a process comprising providing an adhesive layer on a substrate (e g , film, etc ) and laminating a base having a mold release layer such as silicon layer, etc (hereinafter referred to as a "liner") to protect the adhesive layer, and
  • the surface ofthe mold release layer (sometimes referred to as a "mold release surface”) has water repellency That is, regarding a conventional aqueous adhesive composition, wetting to the surface having a water repellency to be coated is insufficient and a coating failure (e.g., cissing, recess, etc.) is generated. Therefore, it is impossible to form a coating which has a sufficient thickness and has no thickness variation
  • an aqueous adhesive composition containing such a thickening agent is disclosed in Japanese Laid-open Patent Publication No. 61 -101555 This composition contains a thickening agent such as a slurry obtained by dissolving xanthanegum in a non-solvent such as alcohol, glycol, glycol monoether, etc
  • a thickening agent such as a slurry obtained by dissolving xanthanegum in a non-solvent such as alcohol, glycol, glycol monoether, etc
  • the thickening agent increases a viscosity ofthe composition to deteriorate a fluidity ofthe composition Therefore, it becomes difficult to form a coating having no thickness variation to obtain well-balanced coating characteristics
  • a nonionic surfactant for example, an aqueous adhesive composition containing such a nonionic surfactant is disclosed in Japanese Laid- Open Patent Publication No 55-30967 This publication discloses a water-soluble sizing agent containing an nonionic surfactant for adh
  • Open Patent Publication No. 4-337381 there is disclosed a solid adhesive composition comprising an adhesive resin, water, a water-miscible organic solvent, a gelatinizing agent and an alkyl glycoxide, which can be applied on the surface to be adhered, smoothly and uniformly, with a small pressure.
  • a water-miscible organic solvent examples include hydroxy group- containing compounds such as cellosolve (ethylene glycol monoethyl ether), butyl carbitol (diethylene glycol monobutyl ether), glycerin, etc.
  • the water-miscible organic solvent is also used for paint, such as industrial high gloss lacquer. However, these solvents have no sufficient performances for improving a wettability to the surface ofthe material such as silicone having a water repellency to form a coating having a sufficient thickness and no thickness variation on the surface to be coated.
  • an aqueous acrylic pressure sensitive adhesive contains such a thickening agent as mentioned above and a surfactant.
  • AROSET resins which is commercially available from Ashland Co. is an emulsion based acrylic pressure sensitive adhesive using an acrylic latex thickening agent
  • the present invention provides an aqueous adhesive composition having the following characteristics ( 1 ) It has a sufficient fluidity (e.g., a viscosity within a suitable range, etc ) at the time of applying operation.
  • the present invention provides an aqueous adhesive composition comprising a mixed solvent of water and a co-solvent, and an adhesive component dissolved or dispersed in the mixed solvent, the co-solvent containing a compound A represented by the formula ( 1 )
  • Ri is a methyl group or an ethyl group
  • R 2 is an alkylene group having 3 to 5 carbon atoms
  • Another aspect of the present invention also provides an adhesive film having the improved adhesive layer as described above
  • Another aspect of the present invention is to provide a process for producing an adhesive film having the improved adhesive layer as described above
  • the aqueous adhesive composition comprises a mixed solvent of water and a co-solvent, and an adhesive component dissolved or dispersed in the mixed solvent, the co-solvent containing a compound A represented by the formula ( 1 )
  • Ri is a methyl group or an ethyl group
  • R 2 is an alkylene group having 3 to 5 carbon atoms
  • the compound A is contained in the mixed solvent to improve solubility or dispersion properties ofthe adhesive component in the mixed solvent, thereby acting on the fluidity and drying rate ofthe adhesive composition to control them within a suitable range
  • the above-described application properties ofthe aqueous adhesive composition as well as stability with time ofthe adhesive force ofthe adhesive layer formed from the adhesive-composition can be improved
  • These properties ofthe compound A manifest from its chemical structure, that is, the fact that it contains no hydroxyl group but contains a methoxy group (or ethoxy group) and an acetoxy group and an alkylene group exists between these functional groups has 3 to 5 carbon atoms
  • the viscosity of the adhesive composition is represented by the viscosity ofthe adhesive composition
  • the viscosity is within a range of 500 to 10,000 cps
  • the viscosity is smaller than 500 cps, it is liable to become difficult to obtain a coating having a sufficient thickness and no thickness variation
  • the viscosity is larger than 10,000 cps, the fluidity is inferior and, therefore, it is likely to become difficult to conduct the applying operation and to supply the adhesive composition to the applying apparatus.
  • the viscosity is too large, air bubbles entrapped at the time of dispersing are not easily escaped and crater, pinhole, etc. are easily generated in the coat
  • the present invention provides an adhesive film comprising a film-like substrate and an adhesive layer formed on the substrate, the adhesive layer being formed by vaporizing a mixed solvent from the aqueous adhesive composition of claim 1 Since this adhesive film is formed from the above adhesive composition, it has no coating failure such as cissing, recess, etc., which are generated in the applying operation Furthermore, it has an adhesive layer having thickness variation within a stated range and the adhesive layer has an adhesive force which is stable with time It is preferred that such an adhesive layer has a compression modulus which is a value measured at 20°C and is within a range of 1 x IO 4 to I O 7 dyne/cm 2 When the compression modulus is smaller than 10 4 dyne/cm 2 , the cohesiveness becomes small and adhesion performances such as retention are liable to become insufficient On the contrary, when the compression modulus is larger than 10 dynecm 2 , the tackiness is deteriorated and it is likely to become difficult to apply the adhesive film
  • the present invention provides a process for producing an adhesive film consisting ofa film-like substrate, an adhesive layer and a liner, which are mutually laminated in this order, comprising the steps of (a) applying the aqueous adhesive composition of claim 1 on a mold release surface ofthe liner, at least one surface of which is the mold release surface, and removing a mixed solvent in the composition to form an adhesive layer, and
  • the compound A is different from the water-miscible organic solvent containing a hydroxyl group in the molecule (e g , cellosolve, etc ) in the fact that the compound A has not a large solubility to water That is, the compound A may have a predetermined solubility to water within a range that it is contained in the mixed solvent to improve the solubility or dispersion properties ofthe adhesive component in the mixed solvent, thereby acting on the fluidity and drying rate ofthe adhesive composition to control them within a suitable range
  • the solubility ofthe compound A to water is normally within a range of 1 to 30 ml/1 00 ml of water, preferably 5 to 20 ml/100 ml of water
  • the number of carbon atoms of R 2 is within a range of 3 to 5
  • the above- described application properties ofthe aqueous adhesive composition can not be improved
  • the productivity becomes inferior
  • An alkylene group of R 2 can take a straight-chain structure or a branched structure
  • Ri is a methyl group, preferably Because the solubility to water becomes comparatively good, which facilitates the improvement of application properties ofthe adhesive composition
  • the vaporization rate ofthe compound A when that of butyl acetate is 100 is preferably within a range of 5 to 50, particularly 8 to 40
  • solubility parameter ofthe compound A is preferably within a range of 8 0 to 10 0, particularly 8 2 to 9 5
  • the adhesive component and additive to be optionally added are dissolved or dispersed in the mixed solvent of water and a co-solvent containing the compound A to form an aqueous adhesive composition solution which can be applied with an applying means
  • the co-solvent can contain a water- miscible organic solvent unless the effect ofthe present invention is damaged
  • the amount of the water-miscible organic solvent to be contained is preferably not more than 20 parts by weight based on 100 parts by weight of water
  • the polymer to be contained in the adhesive component is not specifically limited, and a normal water-soluble or water-dispersible adhesive polymer can be used Examples thereof include polyacrylate, polyvinyl acetate, polyvinyl alcohol, polyurethane, urea, melamine, silicone, natural rubber, synthetic rubber, etc Such a polymer is used after dissolving or dispersing in a mixed solvent.
  • the polymer when the polymer is contained after dispersing, it can be contained as an elastic microsphere ofthe polymer Such an elastic microsphere is described in
  • Additives such as crosslinking agents, tackifiers, plasticizers, etc can be contained in the adhesive component for the purpose of improving performances ofthe adhesive
  • the adhesive composition can contain additives such as thickening agents, surfactants, etc unless the object ofthe present invention is damaged
  • the thickening agent is added to control the viscosity ofthe adhesive composition
  • An alkaline thickening type acrylic emulsion is preferred, for example, there can be used Primal ASE-60 and Primal TT-615 (manufactured by Rohm and Haas (R & H) Co ) It is preferred that the amount ofthe solid content thereof to be added is 0 2 to 3 0 parts by weight, based on 100 parts by weight ofthe adhesive polymer When the amount is smaller than 0 2 part by weight, it is liable to be difficult to obtain a coating having no thickness variation because of insufficient thickening effect On the contrary, when the amount is larger than 3 0 parts by weight, it takes a long time to dry and, therefore, the productivity is likely to become inferior
  • the surfactant is added to adjust the surface tension ofthe adhesive composition
  • the amount ofthe surfactant to be added is normally within a range of 0 005 to 0 5 parts by weight
  • Tryton X-100 polyethylene glycol surfactant, manufactured by R & H Co
  • Tryton GR-5M polyethylene glycol surfactant, manufactured by R & H Co
  • FC-129 fluorine surfactant, manufactured by 3M Co
  • the adhesive composition ofthe present invention is produced by introducing a predetermined amount of water, a compound A, an adhesive component and, if necessary, various additives into a mixing apparatus or dispersing apparatus which has hitherto been known and then uniformly dissolving or dispersing the respective materials.
  • the apparatus include high-speed mixer, planetary mixer, extruder, homogenizer, sand mill, etc.
  • an intermediate composition wherein a material other than an alkaline reagent (e.g , ammonia, etc.) is uniformly dissolved or dispersed is formed and the intermediate composition is thickened by adding the alkaline reagent
  • the aqueous adhesive composition ofthe present invention can be used for forming the adhesive layer of the adhesive film as described hereinafter and is also used as the solvent vaporization type adhesive
  • the aqueous adhesive composition of the present invention is applied on a mold release surface of a substrate or a liner, followed, by drying, to form an adhesive layer
  • the application is conducted, for example, using normal applying apparatuses such as knife coater, gravure coater, roll coater, die coater, etc
  • the drying after application is normally conducted at 80 to 120°C for 3 to 10 minutes
  • the coating weight (weight after drying) ofthe adhesive is 4 to 1 00 g/m 2 when the adhesive film is produced, and it can be optionally selected depending upon the uses
  • the adhesive film of the present invention is formed by laminating an adhesive layer on one or both surfaces of a film-like substrate of materials such as polyethylene, polypropylene, polyester, polyvinyl chloride, polymethyl methacrylate, polycarbonate, paper, metal foil, ceramic thin film, etc and then sealing the adhesive layer to the substrate
  • a film-like substrate of materials such as polyethylene, polypropylene, polyester, polyvinyl chloride, polymethyl methacrylate, polycarbonate, paper, metal foil, ceramic thin film, etc.
  • the thickness of the substrate is normally within a range of 5 to 500 ⁇ m, preferably 20 to 200 ⁇ m
  • the liner having an adhesive layer obtained by applying an adhesive composition directly on a liner, followed by drying the surface ofthe adhesive layer formed is covered with another liner, or the surface ofthe liner which is opposite the surface having the adhesive layer is subjected to a mold release treatment and stored after coiling in the roll form
  • the mold release treatment ofthe liner is normally conducted by providing a mold release layer comprising a silicon compound on the liner
  • a pressure-sensitive adhesive was used This is prepared-by using a polymer ofa monomer mixture having a monomer composition of IOA B A AA (90 7 3) as an adhesive polymer and adding an epoxy compound
  • IOA, BA and AA means isooctyl acrylate, butyl acrylate and acrylic acid, respectively
  • Kuraray Co , Ltd was used Process for preparing sample
  • a predetermined amount of an adhesive, a thickening agent, a surfactant and a compound A as shown in Table 1 were mixed and dispersed, and the mixture was stirred and thickened using ammonia to give an adhesive composition
  • the amount of the respective materials to be formulated are shown in
  • test method Solution fluidity A polyethylene container containing the adhesive composition was allowed to incline at an angle of 45 degrees to evaluate according to the following criteria
  • the compression modulus at 20°C was measured using a viscoelasticity spectrometer RSA II manufactured by Rheometrix Co.
  • An adhesive to be tested was molded in a cylinder having a diameter of 5 mm and a thickness of 7 mm and the cylinder was attached to a parallel plate jig. Then, the temperature dependence of the elastic modulus was measured by changing the temperature within a range between -80 to 150°C while providing a compression strain having a frequency of 1 rad/second.
  • ASE-60, TT-615 and FC-129 means an acrylic emulsion thickening agent available from Rohm and Haas Co , an acrylic emulsion thickening agent available from Rohm and Haas Co. and an fluorine surfactant available from Sumitomo 3M, respectively
  • the adhesive of Comparative Example 1 has a problem in fluidity ofthe solution but those of Examples 1 to 3 have a good fluidity imparted by the addition effect ofthe co-solvent.
  • the adhesives of Comparative Examples 2 and 3 caused a failure such as cissing on the liner but those of Examples 1 to 3 could form a good coating having a improved wettability.
  • an aqueous adhesive composition which are characterized by the following (1 ) It has a sufficient fluidity (e g , a viscosity within a suitable range, etc ) at the time of applying operation
  • an adhesive film to be formed from such a adhesive composition has the adhesive layer having minimal coating failure and thickness variation as described above, and it can exhibit an adhesive force which is stable with time
  • the above adhesive composition can be applied on the surface of an object having a water repellency, uniformly and easily
  • an adhesive film can be produced by a process comprising the steps of applying the above adhesive composition on a mold release surface of a liner, removing a mixed solvent to provide an adhesive layer, laminating a substrate on the adhesive layer and sealing the substrate to the adhesive layer, thereby making it possible to improve the productivity

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention porte sur une couche adhésive présentant de faibles discontinuités et de faibles variations d'épaisseur. Une composition adhésive aqueuse comprend un solvant mixte constitué d'eau et d'un cosolvant dans lequel un adhésif est dissous ou dispersé, le cosolvant contenant un composé A de formule (1) dans laquelle R1 est un groupe méthyle ou éthyle, et R2 un groupe alkylène à 3 à 5 atomes de carbone.
PCT/US1996/012869 1995-09-11 1996-08-08 Composition adhesive aqueuse, film adhesif et son procede de production WO1997010284A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU67676/96A AU6767696A (en) 1995-09-11 1996-08-08 Aqueous adhesive composition, adhesive film and process for producing it
BR9606645A BR9606645A (pt) 1995-09-11 1996-08-08 Composições de adesivo aquoso filme adesivo e processo para produzir um filme adesivo
EP96928081A EP0791030A1 (fr) 1995-09-11 1996-08-08 Composition adhesive aqueuse, film adhesif et son procede de production

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP7232418A JPH0987608A (ja) 1995-09-11 1995-09-11 水系接着剤組成物、接着フィルム、および接着フィルムの製造方法
JP7/232418 1995-09-11

Publications (1)

Publication Number Publication Date
WO1997010284A1 true WO1997010284A1 (fr) 1997-03-20

Family

ID=16938949

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/012869 WO1997010284A1 (fr) 1995-09-11 1996-08-08 Composition adhesive aqueuse, film adhesif et son procede de production

Country Status (7)

Country Link
EP (1) EP0791030A1 (fr)
JP (1) JPH0987608A (fr)
KR (1) KR970707216A (fr)
CN (1) CN1165528A (fr)
AU (1) AU6767696A (fr)
BR (1) BR9606645A (fr)
WO (1) WO1997010284A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8946057B2 (en) * 2012-04-24 2015-02-03 Applied Materials, Inc. Laser and plasma etch wafer dicing using UV-curable adhesive film

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2027642A1 (fr) * 1969-01-02 1970-10-02 Eastman Kodak Co
JPS59207973A (ja) * 1983-05-12 1984-11-26 Kansai Paint Co Ltd 電着塗装用常温乾燥型水性塗料組成物
EP0407952A1 (fr) * 1989-07-11 1991-01-16 Georg Scheidel Jr. Gmbh Composition pour le décapage de revêtements et d'adhésifs
JPH0725821A (ja) * 1993-07-15 1995-01-27 Mitsubishi Chem Corp 新規溶剤およびその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2027642A1 (fr) * 1969-01-02 1970-10-02 Eastman Kodak Co
JPS59207973A (ja) * 1983-05-12 1984-11-26 Kansai Paint Co Ltd 電着塗装用常温乾燥型水性塗料組成物
EP0407952A1 (fr) * 1989-07-11 1991-01-16 Georg Scheidel Jr. Gmbh Composition pour le décapage de revêtements et d'adhésifs
JPH0725821A (ja) * 1993-07-15 1995-01-27 Mitsubishi Chem Corp 新規溶剤およびその製造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 8502, Derwent World Patents Index; Class A82, AN 85-009455, XP002018728 *
DATABASE WPI Section Ch Week 9514, Derwent World Patents Index; Class A60, AN 95-101832, XP002018727 *

Also Published As

Publication number Publication date
KR970707216A (ko) 1997-12-01
CN1165528A (zh) 1997-11-19
BR9606645A (pt) 1997-09-30
AU6767696A (en) 1997-04-01
JPH0987608A (ja) 1997-03-31
EP0791030A1 (fr) 1997-08-27

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