CN104830266B - Optics ultraviolet curing adhesive composition, the cured layer and optical component - Google Patents
Optics ultraviolet curing adhesive composition, the cured layer and optical component Download PDFInfo
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- CN104830266B CN104830266B CN201510064655.XA CN201510064655A CN104830266B CN 104830266 B CN104830266 B CN 104830266B CN 201510064655 A CN201510064655 A CN 201510064655A CN 104830266 B CN104830266 B CN 104830266B
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
- B32B27/26—Layered products comprising a layer of synthetic resin characterised by the use of special additives using curing agents
-
- 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
- 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
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention provides ultraviolet curing adhesive composition, the cured layer and the optical component of the problem of can solve discovery in previous adhesive used in the optical component for be bonded multilayered structure made of a variety of materials.Use a kind of optics ultraviolet curing adhesive composition, it is characterized by comprising: make multifunctional polyurethane (methyl) acrylate (A) obtained from hydrogenated butadiene polymer polyalcohol, aliphatic polyisocyante and (methyl) acrylate reactions with isocyanate group；Polyurethane (B1) obtained from reacting hydrogenated butadiene polymer polyalcohol and aliphatic polyisocyante and any at least one in hydrogenated butadiene polymer polyalcohol (B2)；Simple function (methyl) acrylate (C) that the carbon atom number of alkyl is 8 or more；And Photoepolymerizationinitiater initiater (D), also, solvent content, lower than 1 weight %, the viscosity at 25 DEG C is 100~10000mPas, and Gardner Color is 1 or less.
Description
Technical field
The present invention relates to optics ultraviolet curing adhesive composition, the cured layer and optical components.In more detail and
Speech, is related to being suitable for the Optical Adhesive composition of optical component/component gluing in various optical devices etc., by the group
Close the cured layer that object is formed and the optical component comprising the cured layer.
Background technique
As Optical Adhesive used in optical component/component gluing in optical device etc., glue is not only needed
Viscous force is excellent, and the various function admirables for needing to require in the optical applications such as durability, visible light transmission.For example, liquid crystal
Adhesive used in display panel in the image display devices such as display, e-book etc. is in addition to requiring light resistance, heat resistance
In addition, also demanding adhesive tension and durability.Especially in the case where adhesive itself is used as light transmission medium to use, remove
Other than requiring visible light transmission excellent, in the case where being used as film, also it is required to resistance to vibrated or impact
Adhesive tension, the durability for reducing adhesive tension because of moisture or light.
In addition, in recent years, the slimming of optical component, light-weighted requirement improve, therefore, as composition display device
Each component, instead of inorganic material such as previous glass, metals, the usage rate of resin material is being improved.Accordingly, it is considered to in this way
Resin component heat resistance, be badly in need of developing the cured form for being used without high-temperature heating (such as photocuring, low temperature thermosetting
Change) and with good characteristic as described above adhesive.
In addition, as optics ultraviolet curing adhesive, such as disclose comprising specific carbamate (first
Base) acrylate and specific silicone oil energy ray-curable liquid adhesive composition (referring to patent document 1).But
It is that the adhesive layer obtained by the sizing composition may not can satisfy each characteristic of above-mentioned requirements, and there is room for improvement for tool.
Patent document 1: Japanese Unexamined Patent Publication 2013-64075 bulletin
Summary of the invention
The purpose of the present invention is to provide can solve in the optical component for being bonded multilayered structure made of a variety of materials
The ultraviolet hardening of the problem of being found in the previous adhesive used (gluing is bad, bubble is mixed into, durability is bad etc.)
Adhesive compound.
In view of the above problems, the present inventor has made intensive studies the composition of the adhesive, proportion, as a result, it has been found that, benefit
With the ultraviolet curing adhesive composition for meeting specified conditions, it is able to solve the problem, so as to complete the present invention.
That is, the present invention relates to a kind of optics ultraviolet curing adhesive compositions, which is characterized in that
Include:
Make hydrogenated butadiene polymer polyalcohol, aliphatic polyisocyante and (methyl) acrylate with isocyanate group
Multifunctional polyurethane (methyl) acrylate (A) obtained from reaction；
Polyurethane (B1) obtained from reacting hydrogenated butadiene polymer polyalcohol and aliphatic polyisocyante and hydrogenation
Any at least one in polybutadiene polyol (B2) (wherein, (B1) and (B2) is merged and is known as (B))；
Simple function (methyl) acrylate (C) that the carbon atom number of alkyl is 8 or more；And
Photoepolymerizationinitiater initiater (D), also,
Solvent content is lower than 1 weight %, and the viscosity at 25 DEG C is 100~10000mPas, and Gardner Color is 1 or less.
Moreover, it relates to a kind of optics ultraviolet curing adhesive layer, which is characterized in that by using above-mentioned optics
Ultraviolet curing adhesive composition occurs ultraviolet curing and obtains.
In addition, the present invention relates to a kind of optical components, which is characterized in that include above-mentioned optics ultraviolet curing gluing
Layer.
Invention effect
According to the present invention it is possible to which the optics of display panel as the multilayered structure suitable for numeric display unit etc. is used
The ultraviolet curing adhesive on way and be widely used.For example, being bonded on the panel in the case where being applied to touch panel
When decorative panel, icon sheet or by the formation of the touch panel of electrostatic capacitance method have the transparent substrate of transparent electrode with it is transparent
When plate is bonded, fitting operation can be carried out in the case where and not bubbles excellent in screening characteristics, in addition, passing through ultraviolet curing
Obtained adhesive layer be colorless and transparent and visible light transmission it is excellent, and can play it is not peeling-off, deformation etc. it is excellent
Durability.
Specific embodiment
As described above, optics ultraviolet curing adhesive composition (hereinafter referred to as this composition) of the invention is same
When meet the compositions of following each conditions,
It includes:
Multifunctional polyurethane (methyl) acrylate (A) (hereinafter referred to as (A) ingredient)；
Polyurethane (B1) (hereinafter referred to as (B1) ingredient) and hydrogenated butadiene polymer polyalcohol (B2) (hereinafter referred to as (B2)
Ingredient) any at least one in (being known as (B) ingredient it should be noted that (B1) ingredient and (B2) ingredient are merged)；
Simple function (methyl) acrylate (C) (hereinafter referred to as (C) ingredient) that the carbon atom number of alkyl is 8 or more；And
Photoepolymerizationinitiater initiater (D) (hereinafter referred to as (D) ingredient), also,
Solvent content is lower than 1 weight %, and the viscosity at 25 DEG C is 100~10000mPas, and Gardner Color is 1 or less.
It should be noted that in the present specification, for conventionally, the ultraviolet curing layer obtained by this composition is claimed
For this cured layer, and the optical component comprising this cured layer is known as this component.
In above-mentioned each condition, if solvent content is more than 1 weight %, the meeting in ultraviolet curing of obtained composition
Blistering, is easy to generate bubble in cured layer, it is possible to damage the value of application component, final product.
In above-mentioned each condition, when the viscosity of obtained composition is outside the range of 100~10000mPas, exist often
The tendency that coat operations under temperature, normal pressure reduce.
In addition, if the tone of obtained composition is more than Gardner Color 1, existing and obtaining in above-mentioned each condition
Cured layer tone, the transparency reduce tendency, worry will limit the application in optical applications.
As described above, (A) ingredient is to make hydrogenated butadiene polymer polyalcohol (hereinafter referred to as (a1) ingredient), aliphatic polyisocyanate cyanogen
Acid esters (hereinafter referred to as (a2) ingredient) and with isocyanate group (methyl) acrylate (hereinafter referred to as (a3) ingredient) reaction
Obtained from product.
(a1) ingredient is polyalcohol obtained from hydrogenating to polybutadiene polyol.By using as hydride
(a1) ingredient, this composition and this cured layer of available adhesive tension, excellent durability.(a1) molecular weight of ingredient is without spy
It does not limit, from the viewpoint of adhesive tension, preferably 1000~5000.(a1) iodine number of ingredient is not particularly limited, usually
50 hereinafter, preferably 25 hereinafter, in addition, hydroxyl value is usually 10~200 range, from adhesivity from the viewpoint of durability
From the perspective of, preferably 20~100.In addition, as the commercially available product of (a1) ingredient is corresponded to, such as can enumerate: Japanese Cao
" NISSO-PB GI-1000 ", " NISSO-PB GI-2000 ", " the NISSO-PB GI-3000 ", CRAY manufactured up to Co., Ltd.
" Krasol HLBH-P2000 ", " the Krasol HLBH-P3000 " etc. of VALLEY company manufacture.
As (a2) ingredient, such as can enumerate: dicyclohexyl methyl hydride diisocyanate, isophorone diisocyanate,
Hexamethylene diisocyanate etc., their 2~6 aggressiveness etc., these (a2) ingredients can be with any one individually, in combination
Form uses.By using (a2) ingredient, it is capable of providing this cured layer of adhesive tension, excellent durability.
It as (a3) ingredient, such as can enumerate: (methyl) acrylic acid 2- isocyanatoethyl methacrylate, 1,1- (double acryloyl-oxies
Ylmethyl) ethyl diisocyanate etc., these can be used in the form of any one individually, in combination.
(A) ingredient can by make (a1) ingredient react with (a2) ingredient obtain C-terminal polyurethane after make the hydroxyl
Base end polyurethane reacts to manufacture with (a3) ingredient.In the manufacture of (A) ingredient, can also use makes (a1) ingredient, (a2)
The method that ingredient and (a3) ingredient one react, but from the viewpoint of being easy to control the weight average molecular weight of (A) ingredient, preferably adopt
Use the former.
(A) weight average molecular weight (the polystyrene scaled value obtained by gel permeation chromatography) of ingredient does not limit especially
It is fixed, from the viewpoint of the adhesivity of obtained this composition, this cured layer and durability, preferably 10000~100000.
In addition, the average functional group number of (A) ingredient is not particularly limited, from the viewpoint of the durability of this obtained cured layer
It sets out, preferably 1.5~3.0, more preferably 1.8~2.2.It should be noted that the average functional group number refers in (A) ingredient
1 molecule present in (methyl) acryloyl group mean number.
About the usage amount of (A) ingredient, in 100 parts by weight of this composition, preferably 10~50 weight %, more preferably
25~35 weight %.By the way that the ratio of (A) ingredient is set as 10 weight % or more, this composition, this cured layer can be improved
Adhesive tension, durability, in addition, by the way that the ratio of (A) ingredient is set as 50 weight % hereinafter, can be improved this composition
Operability.
(B) ingredient is any at least one in above-mentioned (B1) ingredient and (B2) ingredient.(B1) ingredient is and (A) ingredient
The identical compound of intermediate, in addition, (B2) ingredient is equivalent to above-mentioned (a1) ingredient.
About the usage amount of (B) ingredient, in 100 parts by weight of this composition, preferably 10~60 weight %, more preferably
25~35 weight %.By the way that the ratio of (B) ingredient is set as 10 weight % or more, this composition, this cured layer can be improved
Adhesive tension, durability, in addition, by the way that the ratio of (B) ingredient is set as 60 weight % hereinafter, can be improved this composition
Operability.
As the concrete example of (C) ingredient, can enumerate: (methyl) 2-EHA, (methyl) acrylic acid are just pungent
Ester, (methyl) Isooctyl acrylate monomer, (methyl) nonyl acrylate, the different nonyl ester of (methyl) acrylic acid, (methyl) decyl acrylate,
(methyl) isodecyl acrylate, (methyl) lauryl acrylate, (methyl) acrylic acid cetyl, (methyl) stearyl acrylate,
(methyl) isostearyl acrylate, (methyl) behenyl acrylate etc. have (methyl) acrylate of chain structure；(methyl)
Isobornyl acrylate, (methyl) acrylic acid dicyclopentenyl base ester, (methyl) dicyclopentyl acrylate, (methyl) acrylic acid two
Cyclopentenyl oxygroup ethyl ester, (methyl) acrylic acid Buddha's warrior attendant alkyl ester etc. have (methyl) acrylate of cyclic structure.
In addition, if using (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) n-propyl, (first
Base) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (first
Base) alkyl such as acrylic acid n-pentyl ester simple function (methyl) acrylate of carbon atom number less than 8, then there is obtained adhesive
The tendency that adhesivity, peculiar smell, the skin irritation of composition are aggravated.
About the usage amount of (C) ingredient, in 100 parts by weight of this composition, the preferably range of 15~74.9 weight %,
The more preferably range of 30~70 weight %.By the way that the ratio of (C) ingredient is set as 15 weight % or more, this group can be improved
The operability for closing object, in addition, by the way that the ratio of (C) ingredient is set as 74.9 weight % hereinafter, can be improved this composition
Curability.
(D) ingredient can not have as long as the Photoepolymerizationinitiater initiater to irradiate decomposition by ultraviolet light and generating free radicals
Use various well known substances with being particularly limited to.Specifically, can enumerate: benzoin compound, acetophenone compound, acyl group
The Photoepolymerizationinitiater initiaters such as phosphine oxide compound, titanocenes compound, thioxanthone compounds, oxime ester compound, the photosensitizers such as amine, quinone
Agent etc. can specifically be enumerated: 2,2- dimethoxy -1,2- diphenylethane -1- ketone, 1- hydroxycyclohexyl phenyl ketone, 2- hydroxyl
Base-2- methyl-1-phenyl-propane-1- ketone, 1- [4- (2- hydroxyl-oxethyl) phenyl]-2- hydroxy-2-methyl-1- propane-1- ketone,
2- hydroxyl-1- [4- [4- (2- hydroxy-2-methyl propiono) benzyl] phenyl]-2- methylpropane-1- ketone, 2- methyl-1-(4- first
Base sulfur phenenyl) -2- morpholino propane -1- ketone, 2- (dimethylamino) -2- [(4- aminomethyl phenyl) methyl] -1- [4- (4- morpholine
Base) phenyl] -1- butanone, 2,4,6- trimethyl benzoyl diphenyl base phosphine oxide, bis- (2,4,6- trimethylbenzoyl) phenyl
Phosphine oxide, bis- (η5- 2,4- cyclopentadiene -1- base)-bis- (the fluoro- 3- of 2,6- bis- (1H- pyrroles -1- base) phenyl) titaniums, 1,2- octane
Diketone 1- [4- (phenylsulfartyl) -2- (o-benzoyl base oxime)], ethyl ketone 1- [9- ethyl -6- (2- methyl benzoyl) -9H- click
Azoles -3- base] -1- (adjacent acetyl group oxime) etc., it can be used alone or two or more kinds may be used.Wherein, 1- hydroxy-cyclohexyl
Phenyl ketone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide can be further improved the curability of this composition, therefore
It is preferred that.
About the usage amount of (D) ingredient, in 100 parts by weight of this composition, preferably 0.1~10 weight %, more preferably
For 0.2~5 weight %.By the way that the ratio of (D) ingredient is set as 0.1 weight % or more, it can prevent from being irradiated by ultraviolet light and draw
That rises solidifies the deviation of polymerization, in addition, by being set as 10 weight % hereinafter, the decomposition product due to (D) ingredient can be reduced
Peculiar smell generate, and the coloring of cured layer can be prevented.
The manufacture of this composition is carried out by mixing above-mentioned (A)~(D) ingredient with desired ratio.About each ingredient
Mixed method and order of addition, be not particularly limited.
In addition, in the present compositions, can according to need within the scope of the effect of the invention containing various more
Functional monomer, tackifier.
It as the concrete example of above-mentioned polyfunctional monomer, can enumerate: 1,4-butanediol two (methyl) acrylate, new penta 2
The tool such as alcohol two (methyl) acrylate, 1,6-hexylene glycols two (methyl) acrylate, 1,9- nonanediol two (methyl) acrylate
There are two (methyl) acrylate of aliphatic structure；Cyclohexanedimethanol two (methyl) acrylate, tristane two (methyl)
Acrylate etc. has two (methyl) acrylate of ester ring type structure；Bisphenol-A epoxy oxide-modified two (methyl) acrylate,
Bisphenol F epoxy oxide-modified two (methyl) acrylate etc. has two (methyl) acrylate of aromatic structure；Trihydroxy methyl
Propane three (methyl) acrylate, isocyanuric acid ethylene-oxide-modified three (methyl) acrylate, pentaerythritol triacrylate,
It is more than the trifunctionals such as pentaerythritol tetraacrylate, Dipentaerythritol Pentaacrylate, dipentaerythritol hexaacrylate more
Function (methyl) acrylate.
It as the concrete example of above-mentioned tackifier, can enumerate: Petropols, phenolic resin, xylene resin, coumarone tree
Rouge, rosin resinoid, terpenoid resin, hydrogenated petroleum resin, hydrogenated rosin resinoid, hydriding terpene resinoid etc..Wherein, excellent
Selecting tone is the resin below of Gardner Color 1.It is the resin below of Gardner Color 1 as tone, such as can enumerates: hydrogen
Fossil oleoresin, hydrogenated rosin resinoid etc..These hydrogenated resins are usually that tone is excellent for 1 or less Gardner Color, the transparency
Therefore good tackifier can be improved the transparency of this composition He this cured layer, and polymerization when ultraviolet curing hinders
Also few, have the advantages that curability is excellent.In addition, for the softening points of these tackifier, aniline point (according to Japanese JIS
K2256), be not particularly limited, if further consider the transparency of this obtained composition, in this composition other are each
The compatibility etc. of ingredient, then preferred softening point is about 80 DEG C~about 120 DEG C, aniline point is about 50 DEG C~about 100 DEG C.As having
The commercially available tackifier of tone, softening point and aniline point as described above, such as can enumerate: Arakawa Chemical Industries, Ltd.
ア イ マ ー Block S-100, エ Network ソ Application that ア Le U Application M-90, M-100 of manufacture, M-115, Idemitsu Kosen Co., Ltd. manufacture
The リ ガ ラ イ ト 5100 etc. that the エ ス U レ ッ Star 5690 of モ ー ビル company manufacture, イ ー ス ト マ Application ケ ミ カ Le company manufacture.
In addition, in the present compositions, can according to need and add within the scope of the effect of the invention containing various
Add agent.For example, can be even containing surface conditioner, surfactant, ultraviolet absorbing agent, antioxidant, inorganic filler, silane
Join the additives such as agent, colloidal silicon dioxide, defoaming agent, wetting agent, antirust agent, stabilizer.
This composition is suitble in display panel and decorative panel, being bonded of icon sheet, is formed with transparent electrode in touch panel
Being bonded for transparent substrate and transparent panel and being bonded etc. for various optical devices, optics for display body and optical functional materials
The adhesive material of component with using on the way.As the material of above-mentioned component, can enumerate: polyethylene terephthalate gathers
Carbonic ester, glass, acrylic resin etc..It as display body, can enumerate: be fitted with the liquid crystal display of polarizing film on glass
The display elements such as device, EL display, EL illumination, e-book, plasma display.As optical functional materials, can enumerate: with
It improves visibility, prevent from causing the acrylic panel for the purpose of the rupture of display element (can be with one or two sides because of external impact
Carry out hard conating process, anti-reflection coating processing), polycarbonate plate, polyethylene terephthalate board, poly- naphthalenedicarboxylic acid second
The transparent plastic sheets such as diol ester, strengthened glass (the anti-film that disperses can be attached with) and contact panel input pickup etc..
The light source of ultraviolet light used in solidification as this composition can be enumerated: have xenon lamp, high-pressure sodium lamp, gold
Belong to the ultraviolet lamp of halide lamp.In addition, the conditions such as light quantity, light source, conveying speed are suitably adjusted, light quantity is usual
It is about 80W/cm~about 160W/cm, conveying speed is typically about 5m/ minutes~about 50m/ minutes.
In addition, the thickness of this cured layer is not particularly limited, about 10 μm~about 1000 μm of usual average out to, preferably 25~
500μm.By the way that thickness is set as the range, the impact resistance of optical component, module can be improved, in addition, table can be absorbed
The printing height in face is poor, therefore can use as the protective film of foremost.
Embodiment
Hereinafter, further illustrating the present invention by embodiment.But the present invention is not limited to these embodiments.Separately
Outside, in embodiment, in case of no particular description, " % " and " part " refers to " weight % ".
<synthesis of (A) ingredient>
Synthesis example 1
(A-1) synthesis of ingredient
In the reaction unit with condenser pipe and blender, the hydrogenated butadiene polymer that weight average molecular weight 4000 is added is polynary
910 parts, 81 parts of isophorone diisocyanate of alcohol (Tso Tat Co., Ltd., Japan's manufacture, trade name " NISSO-PB GI-3000 ")
With 0.2 part of tin octoate, be warming up to 80 DEG C and keep the temperature 2 hours, then, by NCO measure confirmation reaction terminate, obtain as centre
The C-terminal oligourethane of body.Then, 19 parts of methacrylic acid 2- isocyanatoethyl methacrylate is added, is protected at 80 DEG C
Temperature 2 hours, then, measuring confirmation reaction by NCO terminates, and obtains weight average molecular weight 36000, average functional group number 2.0 as a result,
Urethane methacrylate oligomer (hereinafter referred to as (A-1) ingredient).It should be noted that the weight average molecular weight is to pass through
The polystyrene scaled value that gel permeation chromatography obtains, the determination condition [measurement device main body (product name as described below
" HLC-8220GPC ", TOSOH Co., Ltd manufacture), column (product name " TSKGel G1000H ", " TSKGel G2000H ", Tosoh
Co., Ltd. manufacture), developing solvent (tetrahydrofuran)].(similarly hereinafter)
Synthesis example 2
(A-2) synthesis of ingredient
In reaction unit identical with synthesis example 1, it is added more with identical hydrogenated butadiene polymer used in synthesis example 1
925 parts of first alcohol, 51 parts of isophorone diisocyanate and 0.2 part of tin octoate are warming up to 80 DEG C and keep the temperature 2 hours, then, passes through
NCO measurement confirmation reaction terminates, and obtains the C-terminal oligourethane as intermediate.Then, methyl-prop is added
24 parts of olefin(e) acid 2- isocyanatoethyl methacrylate keeps the temperature 2 hours at 80 DEG C, and measuring confirmation reaction by NCO terminates, and obtains weight as a result,
The urethane methacrylate oligomer (hereinafter referred to as (A-2) ingredient) of average molecular weight 21000, average functional group number 2.0.
Synthesis example 3
(A-3) synthesis of ingredient
In reaction unit identical with synthesis example 1, it is added more with identical hydrogenated butadiene polymer used in synthesis example 1
917 parts of first alcohol, 67 parts and 0.2 part of tin octoate of 4,4 '-diisocyanate of dicyclohexyl methyl hydride-, are warming up to 80 DEG C and heat preservation 2 is small
When, then, measuring confirmation reaction by NCO terminates, and obtains the C-terminal oligourethane as intermediate.So
Afterwards, 16 parts of methacrylic acid 2- isocyanatoethyl methacrylate is added, keeps the temperature 2 hours at 80 DEG C, confirmation reaction knot is measured by NCO
Beam, obtain as a result, weight average molecular weight 21000, average functional group number 2.0 urethane methacrylate oligomer (hereinafter referred to as
For (A-3) ingredient).
Compare synthesis example 1
(E-1) synthesis of ingredient
In reaction unit identical with synthesis example 1, polypropylene glycol (the Asahi Glass strain formula meeting of weight average molecular weight 4000 is added
Society's manufacture, trade name " PREMINOL 5001F ") 955 parts, 34 parts of isophorone diisocyanate and 0.2 part of tin octoate, heating
To 80 DEG C and 2 hours are kept the temperature, then, measuring confirmation reaction by NCO terminates, and obtains the C-terminal amino first as intermediate
Acid esters oligomer.Then, 19 parts of methacrylic acid 2- isocyanate is added, keeps the temperature 2 hours at 80 DEG C, is surveyed by NCO
Fixed confirmation reaction terminates, and it is low to obtain weight average molecular weight 36000, the urethane methacrylate of average functional group number 2.0 as a result,
Polymers (hereinafter referred to as (E-1) ingredient).
<synthesis of (B) ingredient>
Synthesis example 4
(B-1) synthesis of ingredient
In reaction unit identical with synthesis example 1, it is added more with identical hydrogenated butadiene polymer used in synthesis example 1
964 parts of first alcohol, 36 parts of isophorone diisocyanate and 0.2 part of tin octoate are warming up to 80 DEG C and keep the temperature 2 hours, then, passes through
NCO measurement confirmation reaction terminates, and obtains the polyurethane (hereinafter referred to as (B-1) ingredient) of weight average molecular weight 9900.
Synthesis example 5
(B-2) synthesis of ingredient
In reaction unit identical with synthesis example 1, it is added more with identical hydrogenated butadiene polymer used in synthesis example 1
942 parts of first alcohol, 58 parts of isophorone diisocyanate and 0.2 part of tin octoate are warming up to 80 DEG C and keep the temperature 2 hours, then, passes through
NCO measurement confirmation reaction terminates, and obtains the polyurethane (hereinafter referred to as (B-2) ingredient) of weight average molecular weight 34000.
Compare synthesis example 2
(E-2) synthesis of ingredient
In reaction unit identical with synthesis example 1, the identical polypropylene glycol used in synthesis example 1 compared with is added
955 parts, 34 parts of isophorone diisocyanate and 0.2 part of tin octoate are warming up to 80 DEG C and keep the temperature 2 hours, then, passes through NCO
Measurement confirmation reaction terminates, and obtains the polyurethane (hereinafter referred to as (E-2) ingredient) of weight average molecular weight 34000.
<preparation of adhesive compound>
Embodiment 1
By 30 parts of (A-1) ingredient, as (B) ingredient hydrogenated butadiene polymer polyalcohol (Tso Tat Co., Ltd., Japan manufacture,
Trade name " NISSO-PB GI-1000 ", hereinafter referred to as (B-3) ingredient) 27 parts, as the isobornyl acrylate of (C) ingredient
10 parts of (manufacture of Osaka organic chemistry Co., Ltd., trade name " IBXA ", hereinafter referred to as (C-1) ingredient), acrylic acid 2- ethyl hexyl
Ester (Mitsubishi chemical Co., Ltd's manufacture, trade name " 2-EHA (ア Network リ Le acid 2- エ チ Le ヘ キ シ Le) ",
Hereinafter referred to as (C-2) ingredient) 45 parts and as (D) ingredient 1- hydroxycyclohexyl phenyl ketone (BASF Amada Co., Ltd. system
Make, trade name " イ Le ガ キ ュ ア 184 ", hereinafter referred to as (D-1) ingredient) 3 parts converted with purity to cooperate, prepare glue
Adhesive composition (referring to table 1).In addition, the Gardner Color, viscosity, solvent containing ratio and compatibility of evaluation the composition, it will
As a result it is shown in table 2 (similarly hereinafter).
Embodiment 2~7
As shown in table 1, the type for changing each ingredient prepares adhesive compound according to method same as Example 1.
Comparative example 1
Without using (B) ingredient, by 57 parts of (A-1) ingredient, 10 parts of (C-1) ingredient, 30 parts of (C-2) ingredient and (D-1) ingredient 3
Part is converted with purity to cooperate, according to method same as Example 1, prepare adhesive compound (referring to table 1, under
Together).
Comparative example 2
Without using (B) ingredient, by 57 parts of (A-2) ingredient, 10 parts of (C-1) ingredient, 30 parts of (C-2) ingredient and (D-1) ingredient 3
Part is converted with purity to cooperate, and adhesive compound is prepared.
Comparative example 3
Without using (A) ingredient, by 57 parts of (B-1) ingredient, 10 parts of (C-1) ingredient, 30 parts of (C-2) ingredient and (D-1) ingredient 3
Part is converted with purity to cooperate, and adhesive compound is prepared.
Comparative example 4
Without using (A) ingredient, by 57 parts of (B-2) ingredient, 10 parts of (C-1) ingredient, 30 parts of (C-2) ingredient and (D-1) ingredient 3
Part is converted with purity to cooperate, and adhesive compound is prepared.
Comparative example 5
Without using (A) ingredient, by 57 parts of (B-3) ingredient, 10 parts of (C-1) ingredient, 30 parts of (C-2) ingredient and (D-1) ingredient 3
Part is converted with purity to cooperate, and adhesive compound is prepared.
Comparative example 6
By 30 parts of A-1) ingredient, 27 parts of (B-3) ingredient, instead of the butyl acrylate (Mitsubishi chemical Co., Ltd of (C) ingredient
Manufacture, trade name " butyl acrylate (ア Network リ Le acid Block チ Le) ", hereinafter referred to as (F-1) ingredient) 40 parts and 3 parts of (D-1) ingredient
It is converted with purity to cooperate, prepares adhesive compound.
Comparative example 7
It will replace 30 parts of (E-1) ingredient, 27 parts of (E-2) ingredient instead of (B) ingredient, (C-1) ingredient 10 of (A) ingredient
3 parts of part, 30 parts of (C-2) ingredient and (D-1) ingredient are converted with purity to cooperate, and prepare adhesive compound.
Table 1
(B-3): hydrogenated butadiene polymer polyalcohol
(Tso Tat Co., Ltd., Japan's manufacture, trade name " NISSO-PB GI-1000 ")
(B-4): hydrogenated butadiene polymer polyalcohol
(Tso Tat Co., Ltd., Japan's manufacture, trade name " NISSO-PB GI-3000 ")
(C-1): isobornyl acrylate (manufacture of Osaka organic chemistry Co., Ltd., trade name " IBXA ")
(C-2): 2-EHA (Mitsubishi chemical Co., Ltd's manufacture, trade name " ア Network リ Le acid 2- エ チ Le
ヘキシル”)
(C-3): (methyl) acrylic acid dicyclopentenyl oxygroup ethyl ester (Hitachi Chemical Co., Ltd.'s manufacture, trade name " Off ァ
ンクリルFA512AS”)
(D-1): 1- hydroxycyclohexyl phenyl ketone (manufacture of BASF Amada Co., Ltd., trade name " イ Le ガ キ ュ ア
184”)
(F-1): butyl acrylate (Mitsubishi chemical Co., Ltd's manufacture, trade name " ア Network リ Le acid Block チ Le ")
Table 2
<Gardner Color>
Gardner Color is measured according to Japanese JIS K5600.
<viscosity>
Viscosity (mPas) is using E type viscosimeter { TVE-10 (Toki Sangyo Co., Ltd.'s manufacture) } at 25 DEG C, 5 minutes
Under the conditions of be measured.
<solvent containing ratio>
About solvent containing ratio, it is measured under the following conditions using gas phase chromatographic device.
(analytical equipment)
GC:Agilent 6850 (manufacture of ア ジ レ Application ト テ Network ノ ロ ジ ー Co., Ltd.)
(GC determination condition)
GC column: HP-1 (manufacture of ア ジ レ Application ト テ Network ノ ロ ジ ー Co., Ltd.)
Column temperature: 50 DEG C (10 minutes) → 10 DEG C/min → 300 DEG C (10 minutes)
Column flow: 2.0ml/ minutes
Carrier gas: helium
Sample injection method: it shunts (50:1)
Detection temperature: 300 DEG C
<compatibility>
About compatibility, obtained adhesive compound is visually observed, is judged based on the following benchmarks.
Zero: uniform, fully transparent
×: confirm any one in gonorrhoea, sediment, insoluble matter or liquid layer separation
<production of test film>
The composition of embodiment 1 is fitted in the glass plate and 0.7mm of 0.7mm thickness in a manner of as 100 μm of film thickness
Between thick glass plate, make it from metal halide lamp (1000mJ/cm2) under by 3 times, thus make its solidification, test be made
Piece.For the composition of embodiment 2~7 and comparative example 1~7, test film is also made in the same way.
[the various evaluations of adhesive layer]
Evaluate example 1~7, comparative evaluation example 1~7
Using above-mentioned test film, implement test below.
<haze value, transmissivity>
Using colored haze meter (カ ラ ー へ イ ズ メ ー タ ー, color technical research institute manufacture in village), according to Japan
JIS K5600 measures the haze value and transmissivity of above-mentioned test film.Show the result in table 3.It should be noted that each haze value is
The numerical value of haze value comprising the glass as substrate.
<heat resistant test>
In heat resistant test, after above-mentioned test film is stood 500 hours in 85 DEG C of temperature of constant temperature and humidity cabinet, by with it is preceding
State same method measurement haze value and transmissivity.Show the result in table 3.It should be noted that each haze value is to include conduct
The numerical value of the haze value of the glass of substrate.
In addition, durability is evaluated based on the following benchmarks.
Zero: without removing, the leaching of adhesion without adhesiver layer, bubble-free and breakage
×: there is removing, there is adhesive layer to leach, have bubble and breakage
<hot resistance test>
In hot resistance test, by above-mentioned test film 85 DEG C of temperature, humidity 85% constant temperature and humidity cabinet in stand 500 hours
Afterwards, by measuring haze value and transmissivity with aforementioned same method.Show the result in table 4.It should be noted that each haze value
For the numerical value of the haze value comprising the glass as substrate.
In addition, durability is evaluated based on the following benchmarks.
Zero: without removing, the leaching of adhesion without adhesiver layer, bubble-free and breakage
×: there is removing, there is adhesive layer to leach, have bubble and breakage
Table 3
Table 4
Claims (6)
1. a kind of optics ultraviolet curing adhesive composition, which is characterized in that
Include:
Make hydrogenated butadiene polymer polyalcohol, aliphatic polyisocyante and (methyl) acrylate reactions with isocyanate group
Obtained from multifunctional polyurethane (methyl) acrylate (A)；
Polyurethane (B1) obtained from reacting hydrogenated butadiene polymer polyalcohol and aliphatic polyisocyante and the poly- fourth of hydrogenation
Any at least one in diene polyol (B2), wherein (B1) and (B2) is merged and is known as (B)；
Simple function (methyl) acrylate (C) that the carbon atom number of alkyl is 8 or more；And
Photoepolymerizationinitiater initiater (D), also,
Solvent content is lower than 1 weight %, and the viscosity at 25 DEG C is 100~10000mPas, and Gardner Color is 1 or less.
2. optics according to claim 1 ultraviolet curing adhesive composition, wherein the weight of (A) ingredient
Average molecular weight is 10000~100000, and the weight average molecular weight is that the polystyrene obtained by gel permeation chromatography converts
Value.
3. optics according to claim 1 or 2 ultraviolet curing adhesive composition, wherein (A) ingredient
Average functional group number is 1.5~3.0.
4. optics according to claim 1 or 2 ultraviolet curing adhesive composition, wherein (A), (B),
(C) and each content of (D) ingredient is followed successively by 10~50 weight %, 5~30 weight %, 5~74.9 weight % and 0.1~10 weight
% is measured, 100 weight % are added up to.
5. a kind of optics ultraviolet curing adhesive layer, which is characterized in that according to any one of claims 1 to 4 by making
Optics ultraviolet curing adhesive composition occurs ultraviolet curing and obtains.
6. a kind of optical component, which is characterized in that include the ultraviolet curing adhesive layer of the optics described in claim 5.
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| JP6643846B2 (en) * | 2015-09-18 | 2020-02-12 | 日本化薬株式会社 | Polyurethane compound and resin composition containing the same |
| JP2017057349A (en) * | 2015-09-18 | 2017-03-23 | 日本化薬株式会社 | Polyurethane compound and resin composition containing the same |
| CN105511106A (en) * | 2016-02-16 | 2016-04-20 | 侯绪华 | Plastic polarized glasses |
| CN105527727A (en) * | 2016-02-16 | 2016-04-27 | 侯绪华 | Plastic polarized glasses |
| JP6819871B2 (en) * | 2016-03-22 | 2021-01-27 | 荒川化学工業株式会社 | Method of manufacturing a laminate |
| JP6697306B2 (en) * | 2016-03-31 | 2020-05-20 | ハリマ化成株式会社 | Photocurable composition with moisture curing, conformal coating agent and cured product |
| KR102378844B1 (en) * | 2016-09-05 | 2022-03-24 | 아라까와 가가꾸 고교 가부시끼가이샤 | Ultraviolet ray-curable adhesive agent, cured product and adhesive sheet |
| WO2019016963A1 (en) * | 2017-07-21 | 2019-01-24 | 日本化薬株式会社 | Ultraviolet curable adhesive, and lamination method and article using same |
| JP6969515B2 (en) * | 2017-07-24 | 2021-11-24 | 荒川化学工業株式会社 | UV curable adhesive, cured product, adhesive sheet |
| JPWO2019093157A1 (en) * | 2017-11-13 | 2021-01-14 | 日本化薬株式会社 | UV-curable adhesive composition, a cured product thereof, and a method for manufacturing an optical member using the UV-curable adhesive composition. |
| CN108485547B (en) * | 2018-02-08 | 2021-11-16 | 康美药业股份有限公司 | Shading film for automatic medicine selling machine and preparation method thereof |
| WO2019208517A1 (en) * | 2018-04-23 | 2019-10-31 | 日本化薬株式会社 | Ultraviolet-curable adhesive composition, cured product thereof, and optical member production method |
| JP7338299B2 (en) * | 2019-07-30 | 2023-09-05 | 株式会社レゾナック | Photocurable adhesive composition and adhesive sheet |
| KR102427059B1 (en) * | 2019-10-28 | 2022-07-29 | 주식회사 엘지화학 | Curable composition |
| KR102425187B1 (en) * | 2019-10-28 | 2022-07-26 | 주식회사 엘지화학 | Curable composition |
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