CN1324390A - Antistatic pressure-sensitive adhesive composition - Google Patents

Antistatic pressure-sensitive adhesive composition Download PDF

Info

Publication number
CN1324390A
CN1324390A CN99812478A CN99812478A CN1324390A CN 1324390 A CN1324390 A CN 1324390A CN 99812478 A CN99812478 A CN 99812478A CN 99812478 A CN99812478 A CN 99812478A CN 1324390 A CN1324390 A CN 1324390A
Authority
CN
China
Prior art keywords
adhesive composition
acrylate
sensitive adhesive
contact adhesive
pressure sensitive
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.)
Granted
Application number
CN99812478A
Other languages
Chinese (zh)
Other versions
CN1210365C (en
Inventor
诹访敏宏
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.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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 Co filed Critical Minnesota Mining and Manufacturing Co
Publication of CN1324390A publication Critical patent/CN1324390A/en
Application granted granted Critical
Publication of CN1210365C publication Critical patent/CN1210365C/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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
    • 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
    • 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
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2170/00—Compositions for adhesives
    • C08G2170/40—Compositions for pressure-sensitive adhesives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

An antistatic pressure-sensitive adhesive composition comprising a copolymer produced upon irradiation polymerization of a polymeric mixture containing a urethane acrylate, a (meth)acrylate having a polyalkylene oxide chain and an adhesion-imparting monomer and the adhesive also contains an ionic compound.

Description

Antistatic pressure-sensitive adhesive composition
The detailed description of invention
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a kind of contact adhesive composition with ionic conductivity and anti-static function.
Prior art
Static electric charge on the insulating element produces the problem of for example adsorbing dust and destroying circuit sometimes.In order to prevent above-mentioned static electric charge, use the sheet material of coated with conductive contact adhesive composition to protect this parts in the practice.For the electrically conductive pressure sensitive adhesives composition, known is to contain with electronics as the metallic stuffing of charged particle carrier or the composition of carbon granule.Also known to the electrically conductive pressure sensitive adhesives composition of ion as charged particle carrier.
In general, with ion during as charged particle carrier, this material is called as solid electrolyte and as being commonly used for the structure unit of battery as described in Japanese Laid-Open Patent Application No.Sho 60 (1985)-47372 etc.According to the description of the document, solid electrolyte is to be made of polymer compound and the ionic compound of being with tool polyethylene oxide side chain.Above-mentioned solid electrolyte is used as the solid electrolyte of electrochemical appliance (as galvanic cell, store battery and electric driven color-changing part), and inviscid.
Japanese Laid-Open Patent Application No.Hei 1-266161 discloses a kind of solid electrolyte with viscosity, is also referred to as the ionic conduction contact adhesive composition.Described contact adhesive composition comprises the multipolymer and the ionic compound of how pure prepolymer of urethane and urethane polyisocyanate prepolymers.Above-mentioned multipolymer is a kind ofly to increase the urethane that increases polymericular weight by polyaddition reaction at the amino-formate bond of urethane oligomer.Above-mentioned reaction is a kind of sequential polymerisation reactions.In general, use catalyzer such as tin, and reaction needs the long time usually.
In addition, the ionic conduction pressure sensitive adhesion sheet is disclosed in the specification sheets and Japanese Laid-Open Patent Application Hei 9 (1997)-208910 of document such as patent gazette Hei 9 (1997)-501009, United States Patent (USP) 5,378,405.The described pressure sensitive adhesion sheet of above-mentioned document comprises the tackiness agent fine particle.Grafting ion conductive material on the fine grain surface of above-mentioned tackiness agent is as on average containing at least 8 ethylene oxide units and forming the nonyl phenol oxygen base polyethylene glycol acrylate of title complex with metal ion.
In general, above-mentioned tackiness agent fine particle is made by suspension polymerization or letex polymerization.In above-mentioned polymerization process, reaction raw materials need be dispersed in the polar solvent (as water).In general, use tensio-active agent to disperse.But even use tensio-active agent, the amount with Acrylic Acid Monomer (as vinylformic acid) of highly water-soluble also is restricted.In addition, passing in time, residual tensio-active agent contained in the pressure sensitive adhesion sheet can be towards the surface transport and the enrichment of bonding object.In many cases, above-mentioned migration and enrichment meeting have problems (changing or residual adhesive is polluted the binding surface) as bonding.When tensio-active agent was enriched on the bonding object surfaces, this zone absorbed water easily.The water of absorption can reduce the surface resistivity of this pressure sensitive adhesion sheet again, thereby obtains antistatic property.But above-mentioned absorption relies on steam to a great extent, so surface resistivity is subjected to the influence of steam easily.In other words, antistatic property may be subjected to the influence of outside atmosphere.
Therefore, the objective of the invention is to make a kind of ionic conduction contact adhesive composition, need not solvent or tensio-active agent during fabrication, it is not subjected to the influence of outside atmosphere as a result.
Need not solvent and tensio-active agent when making contact adhesive composition of the present invention.Therefore can make the ionic conduction pressure sensitive adhesive that antistatic property is not subjected to external environment influence.In addition, pressure sensitive adhesion sheet of the present invention presents very high light transmission.
The general introduction of invention
The antistatic contact adhesive composition of the present invention comprises:
(1) multipolymer that makes through radiation polymerization by the following polymers mixture:
(a) urethane acrylate,
(b) (methyl) acrylate of band polyalkylene oxide chain and
(c) give the monomer of viscosity; And
(2) ionic compound.
Contact adhesive composition of the present invention comprises the multipolymer that radiation polymerization makes.Make this contact adhesive composition and need not solvent, it makes in non-aqueous system.Therefore not existing substantially can residual adhesive and the tensio-active agent and the water that cause the pressure sensitive adhesive surface resistivity to change.
The example of invention
Multipolymer comprises urethane acrylate described in the contact adhesive composition of the present invention, and it makes contact adhesive composition have flexible and rigidity.It is suitable that soft section of alcohol and molecular weight more than having in molecular structure are at least 1000 urethane oligomer.For above-mentioned urethane oligomer acrylate, its example has polyester-polyurethane acrylate and polyether-polyurethane acrylate.The content of urethane acrylate is preferably 10-50 weight % in the multipolymer.If the content of urethane acrylate is too low, then cohesive force is improper.On the other hand, if its content surpasses 50 weight %, then viscosity descends, and this does not conform to demand.Some urethane acrylate is an xanchromatic, and some then is non-xanchromatic.In this case, better use non-xanchromatic urethane acrylate so that make water white contact adhesive composition.Simultaneously, in order to promote the ionic flowability, require the multipolymer in the contact adhesive composition to have low second-order transition temperature.From the angle of viscosity, wish that especially second-order transition temperature is 0 ℃ or lower composition.
Suitable commercial polyurethane acrylate comprises Nippon Synthetic Chemical Co., UV-3000B, UV-3200B and UV-3300B that Ltd. makes, CN-964, the NC-965 that Sartomer Co. makes, CN-966, CN-984, CN-986 etc.In urethane acrylate, the second-order transition temperature of UV-3000B is low especially, is 39 ℃, is preferably.
(methyl) acrylate that has the polyalkylene oxide chain makes contact adhesive composition have ionic conductivity.The polyalkylene oxide chain forms title complex with the positively charged ion with relative small ion radius (as lithium ion, potassium ion and sodium ion), makes contact adhesive composition of the present invention have ionic conductivity.
Example with (methyl) acrylate of polyalkylene oxide chain comprises polyoxyethylene glycol (methyl) acrylate, polypropylene glycol (methyl) acrylate and gathers 1,4-butyleneglycol (methyl) acrylate etc.The molecular weight of above-mentioned (methyl) acrylate does not have special restriction, but from commercially available viewpoint, specially suitable is ShinNakamura Chemical Co., the methoxy poly (ethylene glycol) acrylate (AM-90G) of manufacturing.The ratio of mixture that has (methyl) acrylate of polyalkylene oxide chain in the multipolymer is preferably 50 weight % or lower.When ratio of mixture surpassed 50 weight %, the cohesive force of composition can be reduced to unacceptable degree.
Can control the viscosity of contact adhesive composition according to ratio of mixture with the monomer of giving viscosity.For above-mentioned monomer, can use (methyl) Propylene glycol monoacrylate, (methyl) Hydroxyethyl acrylate, (methyl) vinylformic acid hydroxy butyl ester, vinylformic acid etc.Propylene glycol monoacrylate and high viscosity urethane acrylate have good solvability, so this material can be used as thinner and can mixing effectively or apply in the manufacturing processed of pressure sensitive adhesive.Vinylformic acid strengthens the viscosity with substrate, and it is effective therefore using vinylformic acid when the special high viscosity of needs.In addition, when using monomer to be dispersed in conventional suspension polymerization in the water, therefore consumption (ratio of mixture) is restricted because these monomeric solubleness are high, but the present invention can use any ratio of mixture in solvent-free suspension polymerization.The monomeric amount of giving viscosity contained in the multipolymer is determined by required viscosity.
In general, (methyl) hydroxyalkyl acrylate is preferably 50 weight % or lower as the amount of (methyl) Propylene glycol monoacrylate, and the amount when using vinylformic acid is preferably 30 weight % or lower.Reason is when acrylic acid content increases, and the second-order transition temperature of composition rises, and conductivity degree rises.
For the monomer of multipolymer contained in the contact adhesive composition of the present invention, can comprise can with the comonomer of above-mentioned monomer copolymerization.For example, need dilution contact adhesive composition system and during the rare variation of electrical property or viscosity, the acrylate (as Isooctyl acrylate monomer (IOA)) that can use non-costliness is as comonomer.When needing, the consumption of comonomer is 50 weight % or lower.
As the curing of contact adhesive composition of the present invention, can mention actinic radiation, as UV-light, visible light or electron beam irradiation.In addition, can add the radiation polymerization initiator if necessary.Should use non-yellowing type photo-induced polymerization initiator, especially suitable is for example available from the Darocur of Ciba Geigy Co. 1173, Irgacure 184 etc.In general, the consumption of photo-induced polymerization initiator is that per 100 weight parts monomers are 1 weight part.
Ionic compound in the contact adhesive composition of the present invention and polyalkylene chain formation title complex are also given ionic conductivity.For above-mentioned ionic compound, can mention the compound of positively charged ion (as lithium ion, potassium ion or sodium ion) with relative small ion radius, the for example perchlorate of lithium, potassium or sodium or its inorganic salt, for example muriate, bromide, iodide and thiocyanide.The ionic radius minimum of lithium, so it can make contact adhesive composition have the charge mobility of height.On the other hand, in requiring contact adhesive composition, during non-metallic ion, can use organic salt effectively, as the perchloro-4-butyl ammonium.The content of contact adhesive composition mesoionic compound is preferably 10 weight % or lower.
In order to improve electroconductibility, can in contact adhesive composition of the present invention, add the compound (as Texacar PC) of high-k.Above-mentioned compound with high-k is added the ionic conductivity of the poly-alkane glycol chains in the multipolymer.Compare with (methyl) acrylate (as above-mentioned polyethylene glycol acrylate) with polyalkylene chain, Texacar PC has higher specific inductivity and above-mentioned inorganic salt can be dissolved in the organic salt, thereby can use this compound effectively.
Can add other additive in contact adhesive composition of the present invention, as softening agent, tackifier, oxidation inhibitor etc., having a negative impact only otherwise to the present invention gets final product.
Different with the tackiness agent fine particle that for example letex polymerization or suspension polymerization make, contained multipolymer is with UV-light or electron beam irradiation solidified in the contact adhesive composition of the present invention, therefore need not water and solvent.In the present invention, use the chain polymerization based on the irradiation activation source, compare with above-mentioned sequential polymerization, speed of response is very high.In all types of acrylate, the curing speed of urethane acrylate is very high.Therefore this material can be used to improve the productivity of contact adhesive composition effectively.
Can followingly make contact adhesive composition of the present invention.As required ionic compound (as lithium perchlorate) added and contain urethane acrylate (as polyester-polyurethane acrylate), have in the polymeric blends of (methyl) acrylate monomer (as the methoxy poly (ethylene glycol) acrylate) of polyalkylene chain, the monomer (as Propylene glycol monoacrylate) of giving viscosity and comonomer (as Isooctyl acrylate monomer) and mix.Add photo-induced polymerization initiator subsequently as required, and be stirred to till the thorough dissolving of raw material.Then when the mixture that makes is above carried out UV-light or electron beam irradiation, solidify, make pressure sensitive adhesive.In general, irradiation is 100-1000mJ/cm 2
In addition, contact adhesive composition of the present invention is formed in on-chip and is used as pressure sensitive adhesion sheet.The suitable example of substrate comprises polyester such as polyethylene terephthalate (PET) and PEN (PEN), polyethylene (PE), polypropylene (PP) etc.The thickness of substrate does not have special restriction usually, is generally the 10-200 micron.
Above-mentioned pressure sensitive adhesion sheet can followingly make: mixture that will make above is coated on the substrate (as the PET sheet), places substrate (as PET) with stripper (as siloxanes) processing thereon to make sandwich structure.With the thickness of adjusting pressure sensitive adhesives such as blade coater to obtain required thickness.Applying irradiation such as UV-light and electron beam irradiation is cured to make pressure sensitive adhesion sheet.
In general, the particle diameter of the tackiness agent fine particle that is made by letex polymerization or suspension polymerization (as the described particle of patent gazette Hei9 (1997)-501009) is about 1 micron.Therefore, this particle meeting scattered beam, it is translucent that pressure sensitive adhesion sheet itself is become.In translucent pressure sensitive adhesion sheet, be difficult to the table of discovery plane defect, can record defective when still being bonded in this pressure sensitive adhesion sheet on the parts for the first time.Yet scattering takes place in contact adhesive composition of the present invention hardly, and can make at visible region and have high radioparent pressure sensitive adhesion sheet.Contact adhesive composition of the present invention is 90% or higher when pressure sensitive adhesion sheet thickness is 50 microns to the transmittance of white light.
Illustrate in greater detail the present invention below by embodiment.
Embodiment 1
The following antistatic pressure-sensitive adhesive composition that makes: at first 20 parts of UV-3000B (a kind of urethane acrylate of NipponSynthetic Chemical Industries system) and 20 parts of AM-90G (the methoxy poly (ethylene glycol) acrylate of ShinNakamura Chemical Co. system) are mixed to dissolving fully.Add subsequently 35 parts by weight of acrylic acid hydroxypropyl acrylates, the different monooctyl ester of 15 parts by weight of acrylic acid and 10 weight parts, 0.4 weight % lithium perchlorate AM-90G solution and 1 weight part Darocur 1173 (registered trademark) and be stirred to fully dissolving.
Then, the sample solution that makes is above dropped on the PET substrate of 50 micron thickness, apply substrate again through the PET of siloxane treated.Regulate with blade coater and to make thick 50 microns of the pressure sensitive adhesive that makes.The sample that makes is passed through the ultraviolet light irradiation device fast with the about 800mJ/cm of irradiation 2Irradiation, solidify the pressure sensitive adhesion sheet make.
The surface resistivity of the pressure sensitive adhesion sheet that evaluation makes, viscosity and light transmission.The results are shown in table 1.In this case, the mensuration of surface resistivity is that standard test methods S11.11 according to EOS/ESD association carries out.Measure viscosity according to 180 ° of stripping tests.In addition, measure light transmission with haze meter (Nippon Denshoku Ind., NDH-SENSOR system).It is as shown in the table, and surface resistivity is 1.1 * 10 10Ω/square, this value is for preventing that static electric charge from being quite low.In addition, do not observe adhesive residue, light transmission is 90% or higher, confirms to have good transparency.
Table 1
Pressure sensitive adhesive characteristics
Surface resistivity (Ω/square) ????1.1×10 10
Viscosity (g/25mm) ???????49
Light transmission (%) 90% or higher 1)
Adhesive residue Do not have
Annotate 1) use white light PET substrate in-site detecting.
Embodiment 2
The following antistatic pressure-sensitive adhesive composition that makes: at first 20 parts of urethane acrylate UV-3000B and 20 parts of methoxy poly (ethylene glycol) acrylate AM-90G are mixed to dissolving fully.Add consumption subsequently as showing vinylformic acid (AA) and Isooctyl acrylate monomer, 10 weight parts, 0.4 weight % lithium perchlorate solution and the 1 weight part Darocur 1173 (registered trademark) shown in the II and being stirred to dissolving fully.The mixture that makes as curing as described in the top embodiment 1.
As implied above, (1) use Texacar PC and methoxy poly (ethylene glycol) acrylate as the ionic conduction medium, (2) use vinylformic acid (AA) replaces Propylene glycol monoacrylate, and the ratio of mixture of (3) change vinylformic acid/Isooctyl acrylate monomer, and viscosity is estimated.
The demonstration of table II is applied to the pressure sensitive adhesion sheet that makes on the glass substrate and carries out the result that stripping test obtains.By the result who obtains as seen, viscosity and acrylic acid consumption are closely related.In addition, in all systems, all obtain suitable low surface resistivity.
The table II
AA/IOA (weight part) ?????5/45 ?????10/40 ?????20/30
Viscosity (g/25mm) ?????12 ?????41 ?????590
Adhesive residue Do not have Do not have Do not have
Surface resistivity (Ω/square) ??5.7×10 8 ??1.1×10 9 ??4.0×10 9

Claims (5)

1. antistatic pressure-sensitive adhesive composition comprises:
(1) multipolymer that makes through radiation-initiated polymerization by the following polymers mixture:
(a) urethane acrylate,
(b) (methyl) acrylate of band polyalkylene oxide chain and
(c) give the monomer of viscosity; And
(2) ionic compound.
2. antistatic pressure-sensitive adhesive composition as claimed in claim 1 is characterized in that described urethane acrylate accounts for the 10-50% of described polymeric blends.
3. antistatic pressure-sensitive adhesive composition as claimed in claim 1, (methyl) acrylate that it is characterized in that described band polyalkylene oxide chain accounts in described polymeric blends and is less than 50%.
4. antistatic pressure-sensitive adhesive composition as claimed in claim 1 is characterized in that described ionic compound accounts for and is less than 10 weight % in described contact adhesive composition.
5. pressure sensitive adhesion sheet, it comprises:
(1) substrate and
(2) be formed on contact adhesive composition as claimed in claim 1 on the described substrate surface.
CNB998124788A 1998-10-27 1999-09-28 Antistatic pressure-sensitive adhesive composition Expired - Fee Related CN1210365C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP305164/1998 1998-10-27
JP10305164A JP2000129235A (en) 1998-10-27 1998-10-27 Antistatic pressure-sensitive adhesive composition

Publications (2)

Publication Number Publication Date
CN1324390A true CN1324390A (en) 2001-11-28
CN1210365C CN1210365C (en) 2005-07-13

Family

ID=17941845

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB998124788A Expired - Fee Related CN1210365C (en) 1998-10-27 1999-09-28 Antistatic pressure-sensitive adhesive composition

Country Status (4)

Country Link
JP (1) JP2000129235A (en)
KR (1) KR20010080332A (en)
CN (1) CN1210365C (en)
WO (1) WO2000024839A1 (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101326254B (en) * 2005-10-14 2010-09-08 Lg化学株式会社 Acrylic pressure sensitive adhesive compositions
CN101243152B (en) * 2005-09-05 2010-09-22 日东电工株式会社 Adhesive composition, adhesive sheet, and surface-protective film
CN101243154B (en) * 2005-08-19 2011-03-23 Lg化学株式会社 Acrylic pressure sensitive adhesive composition
CN101208403B (en) * 2005-06-24 2011-06-29 东洋油墨制造株式会社 Antistatic acrylic pressure-sensitive adhesive
CN1884415B (en) * 2005-06-24 2011-09-07 东洋油墨制造株式会社 Antistatic acroleic acid binding agent
CN102449092A (en) * 2009-06-09 2012-05-09 日本合成化学工业株式会社 Pressure-sensitive adhesive composition, pressure-sensitive adhesive, pressure-sensitive adhesive for optical member, and optical member with pressure-sensitive adhesive layer obtained using same
CN105038630A (en) * 2015-07-06 2015-11-11 常熟市长江胶带有限公司 Ultraviolet-cured antistatic adhesive tape, and preparation method thereof
CN110691830A (en) * 2017-05-22 2020-01-14 三星Sdi株式会社 Adhesive film, optical member comprising the same, and optical display comprising the same

Families Citing this family (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4247956B2 (en) * 2001-07-04 2009-04-02 古河電気工業株式会社 Antistatic dicing tape
ATE286936T1 (en) * 2001-08-02 2005-01-15 3M Innovative Properties Co OPTICALLY CLEAR AND ANTISTATIC ADHESIVES
JP2003096232A (en) * 2001-09-26 2003-04-03 Nitto Denko Corp Adhesive and porous film and polymer-gel electrolyte obtained from the same and their use
JP4539081B2 (en) * 2003-11-21 2010-09-08 東洋インキ製造株式会社 Antistatic polyurethane adhesive and method for producing the same
JP5582185B2 (en) * 2003-12-26 2014-09-03 東洋インキＳｃホールディングス株式会社 Removable antistatic acrylic adhesive
JP5422091B2 (en) * 2003-12-26 2014-02-19 東洋インキＳｃホールディングス株式会社 Antistatic acrylic adhesive
EP2246404A1 (en) 2004-03-08 2010-11-03 Nitto Denko Corporation Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheets and surface protecting film
JP4629992B2 (en) * 2004-03-31 2011-02-09 古河電気工業株式会社 Adhesive tape for fixing semiconductor wafers
JP5110675B2 (en) * 2004-04-07 2012-12-26 日東電工株式会社 Pressure-sensitive adhesive composition and pressure-sensitive adhesive sheets using the same
JP4420389B2 (en) * 2004-04-19 2010-02-24 日東電工株式会社 Adhesive composition and adhesive sheet
JP2005314579A (en) 2004-04-30 2005-11-10 Nitto Denko Corp Adhesive composition and adhesive sheets
JP4562070B2 (en) * 2004-05-14 2010-10-13 日東電工株式会社 Adhesive composition, adhesive sheet, and surface protective film
JP4776272B2 (en) * 2004-05-20 2011-09-21 サイデン化学株式会社 Polymer composition for pressure-sensitive adhesive, pressure-sensitive adhesive composition for surface protective film, and surface protective film
JP5437192B2 (en) * 2004-05-26 2014-03-12 日東電工株式会社 Adhesive optical member
TWI388640B (en) 2004-06-01 2013-03-11 Nitto Denko Corp Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet and surface protecting film
JP5794725B2 (en) * 2004-06-01 2015-10-14 日東電工株式会社 Adhesive composition, adhesive sheet and surface protective film
JP5088806B2 (en) * 2004-06-01 2012-12-05 日東電工株式会社 Adhesive composition, adhesive sheet and surface protective film
TWI387629B (en) 2004-07-26 2013-03-01 Nitto Denko Corp Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheets, and surface protecting film
JP5030306B2 (en) * 2004-07-26 2012-09-19 日東電工株式会社 Adhesive composition, adhesive sheet and surface protective film
JP5030251B2 (en) * 2004-07-26 2012-09-19 日東電工株式会社 Adhesive composition, adhesive sheet and surface protective film
KR100694445B1 (en) * 2004-08-24 2007-03-12 주식회사 엘지화학 Acrylic pressure sensitive adhesive having antistaic property
JP4917267B2 (en) 2004-09-16 2012-04-18 日東電工株式会社 Adhesive composition, adhesive sheet, and surface protective film
JP4531628B2 (en) 2004-09-16 2010-08-25 日東電工株式会社 Adhesive composition, adhesive sheet, and surface protective film
JP5535987B2 (en) * 2004-09-16 2014-07-02 日東電工株式会社 Adhesive composition, adhesive sheet, and surface protective film
US7750075B2 (en) * 2004-10-21 2010-07-06 Lg Chem, Ltd. Acrylic pressure sensitive adhesive with good antistatic property
JP4799900B2 (en) * 2004-10-28 2011-10-26 日東電工株式会社 Adhesive composition, adhesive sheet and surface protective film
KR100626709B1 (en) * 2004-12-13 2006-09-21 나노캠텍주식회사 Shielding film transmit electricity and process for preparing the same
JP4358190B2 (en) 2005-03-16 2009-11-04 日東電工株式会社 Adhesive composition, adhesive sheet and surface protective film
CN101175830B (en) 2005-05-20 2011-05-25 日东电工株式会社 Adhesive composition, adhesive sheet, and surface protection film
KR100838973B1 (en) * 2005-06-08 2008-06-17 주식회사 엘지화학 Acrylic pressure sensitive adhesive compositions
KR100784991B1 (en) * 2005-06-10 2007-12-11 주식회사 엘지화학 Acrylic pressure-sensitive adhesive compositions
KR101182989B1 (en) * 2005-06-22 2012-09-18 토요잉크Sc홀딩스주식회사 Antistatic acrylic pressure sensitive adhesive agent
TWI384049B (en) 2005-09-05 2013-02-01 Nitto Denko Corp Adhesive composition, adhesive sheet and surface protective film
KR100760978B1 (en) * 2006-01-21 2007-10-04 광 석 서 Antistatic protection films for display
KR100807910B1 (en) * 2006-06-14 2008-02-27 광 석 서 Antistatic Dicing Tape for Semiconductor Wafer
JP4984735B2 (en) * 2006-08-18 2012-07-25 東洋インキＳｃホールディングス株式会社 Acrylic adhesive manufacturing method
JP4942171B2 (en) * 2006-09-14 2012-05-30 綜研化学株式会社 Adhesive composition and adhesive sheet
KR100810413B1 (en) * 2006-10-23 2008-03-04 율촌화학 주식회사 Adhesive composition for surface protective film and surface protective film using the same
JP5315685B2 (en) * 2006-12-20 2013-10-16 東洋インキＳｃホールディングス株式会社 Antistatic acrylic resin composition
JP5101111B2 (en) 2007-01-05 2012-12-19 日東電工株式会社 Adhesive sheet for semiconductor substrate processing
JP5182465B2 (en) * 2007-01-30 2013-04-17 株式会社ブリヂストン UV curable resin composition for bonding plastic substrates
JP5137102B2 (en) * 2007-03-07 2013-02-06 寛治 林 Antistatic adhesive base solution, antistatic dry laminate adhesive and antistatic composite film
JP5769353B2 (en) * 2007-07-13 2015-08-26 チェイル インダストリーズ インコーポレイテッド Adhesive composition and optical member
JP2009035659A (en) * 2007-08-03 2009-02-19 Finetech Kenkyusho:Kk Cationic antistatic agent, adhesive agent including antistatic agent, and dry laminate film dry-laminated by using adhesive agent
CN101925664B (en) 2007-12-27 2013-05-29 3M创新有限公司 Urea-based pressure sensitive adhesives
WO2010050527A1 (en) * 2008-10-31 2010-05-06 日本合成化学工業株式会社 Adhesive for optical members, optical member having adhesive layer obtained using the same, and adhesive composition for active energy beam-setting and/or thermosetting optical member
JP5623020B2 (en) 2009-02-27 2014-11-12 日東電工株式会社 Adhesive composition, adhesive layer, and adhesive sheet
CN102459490B (en) * 2009-05-15 2014-04-23 3M创新有限公司 Urethane-based pressure sensitive adhesives
JP5385203B2 (en) * 2010-04-05 2014-01-08 日東電工株式会社 Pressure-sensitive adhesive composition and pressure-sensitive adhesive sheets using the same
JP5235021B2 (en) * 2010-04-26 2013-07-10 日東電工株式会社 Adhesive composition, adhesive sheet, and surface protective film
JP5442578B2 (en) * 2010-10-27 2014-03-12 日東電工株式会社 Pressure-sensitive adhesive composition and pressure-sensitive adhesive sheets using the same
JP2011042803A (en) * 2010-10-27 2011-03-03 Nitto Denko Corp Adhesive composition and adhesive sheet using the same
JP5734754B2 (en) 2011-06-10 2015-06-17 藤森工業株式会社 Adhesive composition containing antistatic agent and adhesive film
JP6078222B2 (en) * 2011-06-15 2017-02-08 日東電工株式会社 Adhesive composition and adhesive sheet
JP2014048165A (en) 2012-08-31 2014-03-17 Nitto Denko Corp Destaticizer for analysis
JP6779705B2 (en) * 2016-08-22 2020-11-04 理研ビタミン株式会社 Active energy ray-curable antistatic resin composition
JP6782664B2 (en) 2017-04-28 2020-11-11 藤森工業株式会社 Adhesive composition and surface protective film
DE102019101582A1 (en) * 2019-01-23 2020-07-23 Adhesive Polymers International GmbH & Co. KG Device and method for producing PSA tapes with radiation-induced polymerization of the PSA
JP2020183461A (en) * 2019-04-26 2020-11-12 日立化成株式会社 Composition for pressure-sensitive adhesives, pressure-sensitive adhesive film, and surface-protective film
CN113939563A (en) * 2019-06-07 2022-01-14 积水化学工业株式会社 Resin composition, resin film, and glass laminate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5187007A (en) * 1985-12-27 1993-02-16 Lintec Corporation Adhesive sheets
US5378405A (en) * 1993-07-28 1995-01-03 Minnesota Mining And Manufacturing Company Conductive microparticles and pressure-sensitive adhesive tapes made therefrom
JPH09291258A (en) * 1996-04-26 1997-11-11 Lintec Corp Tacky agent composition and tacky sheet using the same

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101208403B (en) * 2005-06-24 2011-06-29 东洋油墨制造株式会社 Antistatic acrylic pressure-sensitive adhesive
CN1884415B (en) * 2005-06-24 2011-09-07 东洋油墨制造株式会社 Antistatic acroleic acid binding agent
CN101243154B (en) * 2005-08-19 2011-03-23 Lg化学株式会社 Acrylic pressure sensitive adhesive composition
CN101243152B (en) * 2005-09-05 2010-09-22 日东电工株式会社 Adhesive composition, adhesive sheet, and surface-protective film
CN101326254B (en) * 2005-10-14 2010-09-08 Lg化学株式会社 Acrylic pressure sensitive adhesive compositions
CN102449092A (en) * 2009-06-09 2012-05-09 日本合成化学工业株式会社 Pressure-sensitive adhesive composition, pressure-sensitive adhesive, pressure-sensitive adhesive for optical member, and optical member with pressure-sensitive adhesive layer obtained using same
CN105038630A (en) * 2015-07-06 2015-11-11 常熟市长江胶带有限公司 Ultraviolet-cured antistatic adhesive tape, and preparation method thereof
CN110691830A (en) * 2017-05-22 2020-01-14 三星Sdi株式会社 Adhesive film, optical member comprising the same, and optical display comprising the same
US11618837B2 (en) 2017-05-22 2023-04-04 Samsung Sdi Co., Ltd. Adhesive film, optical member including same, and optical display device including same

Also Published As

Publication number Publication date
WO2000024839A1 (en) 2000-05-04
KR20010080332A (en) 2001-08-22
CN1210365C (en) 2005-07-13
JP2000129235A (en) 2000-05-09

Similar Documents

Publication Publication Date Title
CN1210365C (en) Antistatic pressure-sensitive adhesive composition
JP5422091B2 (en) Antistatic acrylic adhesive
KR101437709B1 (en) Pressure-sensitive adhesive sheet
CN1749344B (en) Pressure-sensitive adhesive compositions, pressure-sensitive adhesive sheets and surface protecting films
TWI691570B (en) Adhesive composition, adhesive sheet and display
CN100404569C (en) Anti-electrostatic cutting band
JP4984735B2 (en) Acrylic adhesive manufacturing method
JP2007002111A (en) Antistatic acrylic pressure-sensitive adhesive
CN101889065A (en) Adhesive composition, adhesive article, adhesive composition for optical use, and adhesion method
CN104371581A (en) Surface protection film and optical component attached with the same
KR100762729B1 (en) Transparent conductive material and transparent conductive member
JP5617987B2 (en) Antistatic acrylic adhesive
JP2007002112A (en) Method for decreasing surface resistance value of insulation substrate
JP2019014897A (en) Adhesive layer and adhesive film
KR20220136058A (en) Display
KR102541682B1 (en) Surface protection tape
JP2010168541A (en) Pressure-sensitive adhesive tape or sheet
JP4362093B2 (en) Ionizing radiation curable composition for forming antistatic film, antistatic film and structure comprising antistatic film
JP2019014899A (en) Adhesive layer and adhesive film
CN110776854B (en) Adhesive sheet and laminate
KR20190079894A (en) Antistatic adhesive composition and protection film, polarizing plate and display device
KR101182989B1 (en) Antistatic acrylic pressure sensitive adhesive agent
CN108285761B (en) Adhesive and protective tape
JP2007296751A (en) Resin laminate
JP2003053924A (en) Base material for polarizing plate protecting film

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C19 Lapse of patent right due to non-payment of the annual fee
CF01 Termination of patent right due to non-payment of annual fee