CN101693820A - Methyl acrylate pressure-sensitive adhesive for LCD polarizer and preparation method thereof - Google Patents
Methyl acrylate pressure-sensitive adhesive for LCD polarizer and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a methyl acrylate pressure-sensitive adhesive for an LCD polarizer and a preparation method thereof, which belong to the technical field of tackiness agent. The pressure-sensitive adhesive comprises the following three materials with the quality shares: a. weight average molecular weight Mw is 100000-2000000, dispersion degree Mw/Mn is 4-20 acrylate copolymer 100 shares, b. coupling agent, c. cross linker 0-15 shares, the comonomer of prepared acrylate copolymer comprises two parts: 1. (methyl) acrylate monomer : 90%-99.5%, 2. functional monomer: 0.5%-10%, wherein the functional monomer is one or several of (methyl) acroleic acid and (methyl) acroleic acid hydroxy ethyl, (methyl) acroleic acid hydroxypropyl acrylate, itaconic acid, acrylamide, N-hydroxymethyl acrylamide and maleic anhydride. The methyl acrylate pressure-sensitive adhesive does not contain elasticizer or low-molecular-weight acrylate copolymer and the like, can reach the use requirement without cross linker under the condition that the requirement to sticking property is low, and the glue layer has better stress relaxation property, and pressure-sensitive adhesive initial adhesion and stripping strength are both extremely ideal.
Description
Technical field:
The present invention relates to the solvent-type acrylic ester pressure-sensitive.Belong to the sizing agent technical field.
Background technology:
Pressure-sensitive acrylate can be used as the packaged pressure sensitive adhesive tape, label pressure sensitive adhesive etc.In the display panels field because its transparency and humidity resistance are widely used in the face glass and the polaroid of slurr crystal display.Specifically, in production application, enclose one deck pressure sensitive adhesive, and fit and go up the barrier film that pressure sensitive adhesive is protected in the one side of polaroid.Tear barrier film like this off, expose pressure sensitive adhesive, polaroid just can be attached on the face glass of liquid-crystal display conveniently and solidly.This polaroid pressure sensitive adhesive that is used for liquid-crystal display need have good releasable, performances such as higher stripping strength and initial bonding strength.At present, domestic technology is also comparatively weak.
Because polaroid has very high requirement with acrylate pressure-sensitive adhesive to the glue-line performance, one-component is difficult to satisfy desired properties, can adopt a plurality of components and the method by blend to prepare pressure sensitive adhesive usually.
The pressure-sensitive adhesive that JP2004002782 introduces the preparation of Nippon Carbide Industries company mainly comprises 4 parts: A: high molecular weight copolymer Mw is 900000～2500000, B: low-molecular weight copolymer Mw is 50000～200000, C: 0.001～10 part of linking agent (with reacting), D: silane coupling agent.Its adopts and sneak into a small amount of low-molecular-weight acrylate copolymer in the high-molecular weight acrylate copolymer, and molecular weight distribution is broadened, and can improve initial bonding strength and stripping strength greatly keeping holding preferably under the situation of viscous force.
JP200109771 introduces Lintec Co.Lid company synthetic polaroid and also adopts with pressure-sensitive adhesive the acrylic ester polymer of high molecular 600000～2000000 and molecular weight are mixed less than 5000000 acrylic ester polymer.Preferably having a kind of monomer at least is both to be used to constitute high-molecular weight polymer, is used to constitute low-molecular weight polymer again.Low-molecular weight polymer is added in the high-molecular weight polymer, and ratio is 0.1～50: 100.With butyl acrylate and vinylformic acid is that the principal monomer polymerization obtains acrylic ester polymer, and Mw is 1500000, adds trioctyl trimellitate then and the trimethoxytoluene vulcabond carries out crosslinked.The material of a spot of normal stress factor that also mixed the people in the pressure-sensitive adhesive.
JP2002047468 introduces the polaroid pressure sensitive adhesive that saiden chemical industrial company has synthesized a kind of self-adhesion coating, it has good self-adhesion characteristic under the condition of high temperature and high humidity, it is 800000～2000000 multipolymer (can and contain the unsaturated monomer copolymerization of carboxyl or hydroxyl by alkyl methacrylate) that this pressure-sensitive adhesive mainly comprises A: weight-average molecular weight Mw, 100 parts of consumptions; B: weight-average molecular weight Mw is less than (methyl) acrylic acid alkyl vinegar polymkeric substance of 50000 no functional group, and dispersity Mw/Mn is 1.0-2.5,5～50 parts of C of consumption: 0.01～2 part of .D of linking agent: contain alkoxysilane compound containing trialkylsilyl group in molecular structure.
But because the monomer of the monomer of low-molecular weight copolymer and high molecular weight copolymer composition is not quite identical, thereby influence the consistency of system, worsen the performance of glue-line.In addition, also can make and cut glue and become inconvenient.Therefore, need development can avoid adding the pressure sensitive adhesive of low-molecular weight copolymer or softening agent.
Summary of the invention:
The purpose of this invention is to provide a kind of initial bonding strength, the solvent-type acrylic ester pressure-sensitive that performances such as stripping strength are preferable.This pressure sensitive adhesive does not contain low-molecular-weight acrylic resin and softening agent.Main as the polaroid pressure sensitive adhesive, also can be applicable to make general packaging Pressuresensitive Tape, Pressuresensitive Label etc.
The present invention mainly is that control molecular weight and molecular weight distribution realize by adding long-chain comonomer.The reason that can avoid adding low molecular weight propylene acid resin or softening agent is mainly following several respects: 1. two used class acrylic comonomers have different chain lengths, long segment has been given glue-line tack preferably, short segment can be given the better cohesive strength 2. of glue-line and adopt suitable polymerization methods, make multipolymer have the distribution of broad, low-molecular-weight like this part can provide viscosity, the high-molecular weight part can provide cohesive strength, simultaneously because comonomer is identical, so there is not the suitable degree of crosslinking of compatibility problem 3. controls, owing to adopt the long-chain monomer copolymerization, control certain degree of crosslinking and can avoid the not enough problem of cohesive strength.
The object of the present invention is achieved like this: described pressure sensitive adhesive is the mixture of 3 part blend before oven dry is left standstill: a. weight-average molecular weight Mw is 100000～2000000, and dispersity Mw/Mn is 0～15 part of 0.1～5 part of c. linking agent of 100 parts of b. coupling agents of acrylate copolymer of 4～20.In addition, contain 50～500 parts solvent.Described solvent is aromatic hydrocarbon based, ester class, the mixture of one or more in alcohols and the ketone.
The described comonomer that makes acrylate copolymer is made of 2 parts, and following percentage ratio is mass percent; : 1. (methyl) acrylate monomer: 90%～99%, 2. functional monomer: 0.5%～6%.Described (methyl) acrylate monomer, can represent with following general formula:
Wherein R1 is hydrogen atom or methyl, and R2 is that carbonatoms is 1～18 alkyl.Specifically, comprise n-butyl acrylate, vinylformic acid n-octyl, Isooctyl acrylate monomer (claiming 2-EHA again) dodecyl acrylate, tetradecyl acrylate, Process Conditions of Cetane Acrylate, (methyl) methyl acrylate, ethyl propenoate, the methacrylic dodecyl gallate, tridecyl acrylate, the positive certain herbaceous plants with big flowers ester of vinylformic acid, decyl acrylate etc.(methyl) acrylate monomer of described participation copolymerization must be made of two portions:
A. contain a kind of R2 at least and be carbonatoms and be the monomer of 9～18 alkyl: 15%～65%
B. contain a kind of R2 at least and be carbonatoms and be the monomer of 1～6 alkyl: 35%～85%.Described functional monomer is (methyl) vinylformic acid, (methyl) Hydroxyethyl acrylate, (methyl) Propylene glycol monoacrylate, methylene-succinic acid, acrylamide, N hydroxymethyl acrylamide, one or more in the maleic anhydride.
Described acrylate copolymer causes comonomer by radical initiator and obtains by solution polymerization.Initiator is a kind of in azo-bis-isobutyl cyanide (AIBN) or the dibenzoyl peroxide (BPO), and the gross weight that initiator adds is 0.03%～0.6% of a total monomer weight.Copolymerization temperature is 50 ℃～100 ℃, preferred 60 ℃～90 ℃.The solvent that adopts in the solution polymerization is an organic solvent, for aromatic hydrocarbon based, and the ester class, the mixture of one or more in alcohols and the ketone specifically comprises ethyl acetate, toluene, acetone, n-propyl alcohol, Virahol, butylacetate etc.
Coupling agent is that silane coupling agent is γ-An Bingjisanyiyangjiguiwan (KH550), γ-2,3-glycidoxypropyltrime,hoxysilane (KH560), a kind of in γ-methacryloxypropyl trimethoxy silane (KH570).Coupling agent can improve the adhesive ability to glass.
Linking agent is one or more the mixture in isocyanate compound and the Resins, epoxy.Main purpose is to make glue-line suitably crosslinked, glue-line can be used for a long time and performance does not descend.
Described isocyanate compound is a tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, Xylene Diisocyanate, hydrogenated xylene diisocyanate, diphenylmethanediisocyanate, hydrogenated diphenyl methane diisocyanate; Make above-mentioned isocyanic ester and glycerine, polyol reaction such as TriMethylolPropane(TMP) and the adducts that obtains and isocyanate compound 2,3 in one or more mixture.
Resins, epoxy comprises bisphenol A epoxide resin, polyethyleneglycol diglycidylether, diglycidyl ether of ethylene glycol, glycerin diglycidyl ether, glycerine triglycidyl group ether, trimethylolpropane tris glycidyl ether, the mixture of one or more in the diglycidylaniline.
Also can require to add anti-aging agent, UV light absorber, flow agent according to reality.Described anti-aging agent comprises triphenyl phosphite, diphosphorous acid tetramethylolmethane two hard acid fat, three (2, the 4-di-tert-butyl-phenyl) phosphorous acid ester, [β (3,5-di-t-butyl 4-hydroxyl-phenyl) propionic acid] pentaerythritol ester, Tyox B etc.UV light absorber comprises 2-(2-hydroxy-5-methyl base phenyl) benzotriazole, Octabenzone etc.Flow agent comprises polyacrylic ester, silicone resin, fluorine surfactant.Comprise BYK-306, BYK-373, HX-3010 etc.
With weight-average molecular weight Mw is that acrylate copolymer adds coupling agent according to said ratio, linking agent, and add organic solvent with convenient coating, be coated on the barrier film after mixing, the solvent that adds is aromatic hydrocarbon based, ester class, the mixture of one or more in alcohols and the ketone.Bake out temperature is 50 ℃～150 ℃, and preferred 60 ℃～100 ℃, temperature is too low loses time, the too high glue-line degradation of temperature, and drying time generally is controlled at 0.5h～16h.
The present invention distinguishes with general polaroid and is that with the solvent-type acrylic ester pressure-sensitive prepared pressure sensitive adhesive does not contain components such as softening agent or low-molecular-weight acrylate copolymer, for hold viscosity can less demanding situation under, pressure sensitive adhesive of the present invention can not use linking agent just can reach the requirement of use.The present invention mainly is that control molecular weight and molecular weight distribution realize that glue-line has stress relaxation ability preferably by adding long-chain comonomer, the pressure sensitive adhesive initial bonding strength, and stripping strength is all very good, so range of application is wide.
Embodiment
Following embodiment can illustrate further characteristics of the present invention, but not limited by these examples." part " among the embodiment is a weight basis.
Molecular weight and molecular weight distribution are recorded by the GPC that waters company produces, and weight-average molecular weight is measured by the polystyrene standard conversion and obtained.The sample concentration of GPC test is 2mg/mL, and the sample import volume is 50 μ mL, and 30 ℃ of temperature under the condition of flow velocity 1mL/min, are measured by the tetrahydrofuran (THF) dissolving.
Initial bonding strength is measured and is adopted the spin slope to stop test method(s), adopts the GB/T4852-2002 testing standard, 30 ℃ of measured angular.
Stripping strength is measured and is adopted
GB-T2792-1981Testing standard
Polymerization example 1:
Prolong is being housed, nitrogen replaceable equipment, agitator, in the reactor of temperature regulating device, add 180 parts of ethyl acetate (EAc), 50 parts dodecyl acrylate (LA), 46 parts of butyl acrylates (BA), 1 part acrylate (AA), 3 parts Hydroxyethyl acrylate (HEA), 0.075 part azo-bis-isobutyl cyanide (AIBN).Feed nitrogen (N earlier
2), behind air in the nitrogen replacement system, with interior temperature rise to 65 ℃, behind the reaction 5h, with interior temperature rise to 71 ℃, reaction 2h.Add 0.15 part the AIBN and the mixing solutions of 25 parts of ethyl acetate again, behind the reaction 2h, be cooled to 40 ℃, finish reaction.
Polymerization example 2～3
Polymerization process is with polymerization example 1, and just the ratio of comonomer is different with composition, sees Table 1
Polymerization example 4:
Prolong is being housed, nitrogen replaceable equipment, agitator in the reactor of temperature regulating device, adds 56.5 parts BA, 23 parts octadecyl acrylate (SA), 20 parts 2-EHA (2-EHA), the ethyl acetate of 0.5 part AA and 85 parts feeds N earlier
2, replace the air in the system fully after, with interior temperature rise to 60 ℃, at the uniform velocity to drip the mixing solutions of initiator A IBN0.03 part and 85 parts of ethyl acetate in 3h, warm at 62 ℃ in the control then, isothermal reaction 8h is cooled to 40 ℃, discharging.
Polymerization example 5:
Prolong is being housed, nitrogen replaceable equipment, agitator, in the reactor of temperature regulating device, the ethyl propenoate (EA) that adds 22 parts, 60 parts BA, the positive certain herbaceous plants with big flowers ester of 15 parts vinylformic acid (DA), 1.5 the AA of part, 1.5 the mixed solution of the hydroxyethyl methylacrylate (HEMA) of part and 60 parts of ethyl acetate of 120 parts of toluene and 0.06 part dibenzoyl peroxide (BPO), feed N2 earlier and replace the interior air of system fully, temperature is to 74 ℃ of reaction 1h in raising then, 1h adds 0.3 part of BPO with 20 parts of toluene and ethyl acetate mixture (toluene and ethyl acetate weight ratio are 3: 2), adds 0.24 part of BPO behind the 4h with 20 parts of toluene and ethyl acetate mixture (toluene and ethyl acetate weight ratio are 3: 2).Be warming up to 100 ℃ behind the 3h, reaction 1.5h is cooled to 40 ℃.
Polymerization example 6:
Just the ratio of comonomer is different with composition with polymerization example 5 for polymerization process, sees Table 1
Polymerization example 7:
Prolong is being housed, nitrogen replaceable equipment, agitator in the reactor of temperature regulating device, adds 15 parts methyl acrylate (MA), 20 parts butyl methacrylate (BMA), 61 parts Ethyl acrylate (HA), 1 part AA, the ethyl acetate of 3 parts Hydroxyethyl acrylate (HEA) and 80 parts, feed N2 earlier, after replacing the air in the system fully, with interior temperature rise to 64 ℃, at the uniform velocity in 4h, to drip the mixing solutions of initiator A IBN0.4 part and 120 parts of ethyl acetate, warm in the control then at 64 ℃, isothermal reaction 3h is warming up to 69 ℃ behind the 3h, behind the reaction 2h, be cooled to 40 ℃, discharging.
Polymerization example 8～9:
Polymerization process is with polymerization example 7, and just the ratio of comonomer is different with composition, sees Table 1
Table 1. polymerization single polymerization monomer schedule of proportion
The multipolymer that the polymerization example is obtained adds coupling agent by the proportioning of table 2, linking agent, wherein, polymerization example 1～4,7～9 add ethyl acetate adjusts viscosity, polymerization example 5～6 adds toluene and the ethyl acetate weight ratio is that 3: 2 mixed solvents are adjusted viscosity, and the control solid content was at 30～55% o'clock, and coating viscosity is proper.Be coated on the barrier film after above-mentioned substance mixed,, leave standstill 12h and just can obtain the described pressure sensitive adhesive of embodiment at 60 ℃ of baking 4h down.
Annotate: the corresponding polymerization example 1 of the acrylate copolymer among the embodiment 1, the rest may be inferred for other.Mn is a number-average molecular weight, and Mw is a weight-average molecular weight.
Embodiment 1～3 coupling agent is KH550, and embodiment 4～6 coupling agents are KH560, and embodiment 7～9 coupling agents are KH570.It is TriMethylolPropane(TMP) and tolylene diisocyanate affixture that embodiment 1～4 adds linking agent, and embodiment 5～9 linking agents are polyethyleneglycol diglycidylether and toluene diisocyanate dimer.Embodiment 1～5 anti-aging agent adds 0.6 part, and the uv-absorbing agent Octabenzone adds 0.5 part, and flow agent BKY-306 adds 0.5 part
Do as one likes can be tested as can be known, and made pressure sensitive adhesive characteristic is good, can satisfy service requirements.
Claims (6)
1. acrylate pressure-sensitive adhesive, it is characterized in that, comprise three kinds of materials of following massfraction: a. weight-average molecular weight Mw is 100000～2000000, and dispersity Mw/Mn is 0～15 part of 0.1～5 part of c. linking agent of 100 parts of b. coupling agents of acrylate copolymer of 4～20;
. the described comonomer that makes acrylate copolymer is made of following 2 parts, and following percentage ratio is mass percent; 1. (methyl) acrylate monomer: 90%～99.5%, 2. functional monomer: 0.5%～10%
Described (methyl) acrylate monomer, represent with following general formula:
Wherein R1 is hydrogen atom or methyl, and R2 is that carbonatoms is 1～18 alkyl, and (methyl) acrylate monomer of participation copolymerization is made of following two portions:
A. contain a kind of R2 at least and be carbonatoms and be the monomer of 9～18 alkyl: 15%～65%
B. contain a kind of R2 at least and be carbonatoms and be the monomer of 1～6 alkyl: 35%～85%
Described functional monomer is (methyl) vinylformic acid, (methyl) Hydroxyethyl acrylate, (methyl) Propylene glycol monoacrylate, methylene-succinic acid, acrylamide, N hydroxymethyl acrylamide, one or more in the maleic anhydride.
2. pressure sensitive adhesive according to claim 1 is characterized in that, described acrylate copolymer causes comonomer by radical initiator and obtains by solution polymerization; Initiator is a kind of in azo-bis-isobutyl cyanide or the dibenzoyl peroxide, and the gross weight that initiator adds is 0.03%～0.6% of a total monomer weight; Copolymerization temperature is 50 ℃～100 ℃; Polymerization process adopts N
2Protection; The solvent that adopts in the solution polymerization is an organic solvent, for aromatic hydrocarbon based, and ester class, the mixture of one or more in alcohols and the ketone.
3. pressure sensitive adhesive according to claim 1, it is characterized in that. coupling agent is that silane coupling agent is a γ-An Bingjisanyiyangjiguiwan, γ-2, the 3-glycidoxypropyltrime,hoxysilane, a kind of in γ-methacryloxypropyl trimethoxy silane.
4. pressure sensitive adhesive according to claim 1 is characterized in that, linking agent is one or more the mixture in isocyanate compound and the Resins, epoxy; Described isocyanate compound is a tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, Xylene Diisocyanate, hydrogenated xylene diisocyanate, diphenylmethanediisocyanate, hydrogenated diphenyl methane diisocyanate; Perhaps linking agent is one or more the mixture that makes in 2,3 aggressiveness of compound that above-mentioned isocyanic ester and polyol reaction obtain and above-mentioned isocyanic ester; Described Resins, epoxy is bisphenol A epoxide resin, polyethyleneglycol diglycidylether, diglycidyl ether of ethylene glycol, glycerin diglycidyl ether, glycerine triglycidyl group ether, trimethylolpropane tris glycidyl ether, the mixture of one or more in the diglycidylaniline.
5. pressure sensitive adhesive according to claim 1 is characterized in that. also add anti-aging agent, anti UV agent or flow agent.
6. the preparation method of pressure sensitive adhesive according to claim 1, it is characterized in that, with weight-average molecular weight Mw is 100000～2000000, dispersity Mw/Mn is that 4～20 acrylate copolymer 1 adds coupling agent according to said ratio, linking agent, and add solvent and be adjusted to the viscosity that can be used for being coated with, be coated on the barrier film after mixing, just can obtain pressure sensitive adhesive 50 ℃～150 ℃ following dry out solvent; Described solvent is aromatic hydrocarbon based, ester class, the mixture of one or more in alcohols and the ketone.
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