CN104830266A - Ultraviolet light solidified-type adhesive composition for optics and solidified layer and optical component thereof - Google Patents
Ultraviolet light solidified-type adhesive composition for optics and solidified layer and optical component thereof Download PDFInfo
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- CN104830266A CN104830266A CN201510064655.XA CN201510064655A CN104830266A CN 104830266 A CN104830266 A CN 104830266A CN 201510064655 A CN201510064655 A CN 201510064655A CN 104830266 A CN104830266 A CN 104830266A
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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
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- 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
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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
- 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
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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
- 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
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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
- 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 invention provides an ultraviolet light solidified-type adhesive composition for optics and a solidified layer and an optical component thereof, which is capable of solving the problems that are found in the previous adhesive used in an optical component with multi-layer structure formed by sticking various materials, wherein the use of the ultraviolet light solidified-type adhesive composition for optics is characterized in that the ultraviolet light solidified-type adhesive composition comprises polyfunctional polyurethane (methyl) acrylate (A) obtained by the reaction between hydrogenated polybutadiene polyol, aliphatic series polyisocyanate and acrylate with isocyanate group (methyl), at least one of polyurethane (B1) and hydrogenated polybutadiene polyol (B2) that are obtained through the reaction between hydrogenated polybutadiene polyol and aliphatic series polyisocyanate,single-function (methyl) acrylate (C) with more than 8 carbon atoms of alkyl, and photoplymerization initiator (D); the solvent content is less than 1 weight percent; the viscosity under 25 DEG is with the range of 100 to 10000 mPa s; and the Gardner chroma is less than 1.
Description
Technical field
The present invention relates to optics ultraviolet hardening adhesive compound, this cured layer and optical component.More specifically, relate to the gluing Optical Adhesive composition of the optical component/parts be suitable in various optical devices etc., the cured layer formed by said composition and comprise the optical component of this cured layer.
Background technology
As the Optical Adhesive of the gluing middle use of the optics/component in optical device etc., not only need adhesive power excellent, and need the various excellent propertys that require in the optical applications such as weather resistance, visible light transmission.Such as, the tackiness agent used in the display panel in the image display device such as liquid-crystal display, e-book etc., except requiring photostabilization, thermotolerance, also requires high adhesive power and weather resistance.Particularly when tackiness agent itself uses as light transmission medium, except requiring that visible light transmission is excellent, when using as film, also requirement can resistance to vibrated or the adhesive power of impacting, the weather resistance that because of moisture or light, adhesive power reduced.
In addition, in recent years, the slimming of optical component, light-weighted requirement improve, and therefore, as each component forming display unit, replace the inorganic materials such as glass, metal in the past, and the usage rate of resin material is in raising.Therefore, consider the thermotolerance of such resin component element, being badly in need of developing use does not need the cured form of heat (such as photocuring, low temperature heating-curing) and the tackiness agent with good characteristic as above.
In addition, as optics ultraviolet hardening tackiness agent, such as, disclose the liquid adhesive composition (with reference to patent documentation 1) of the energy ray-curable comprising specific carbamate (methyl) acrylate and specific silicone oil.But the adhesive layer obtained by this sizing composition may not meet each characteristic of above-mentioned requirements, has the leeway of improvement.
Patent documentation 1: Japanese Unexamined Patent Publication 2013-64075 publication
Summary of the invention
The object of the present invention is to provide the ultraviolet hardening adhesive compound that can solve the problem (gluing bad, bubble is mixed into, weather resistance is bad) found in the tackiness agent in the past that uses in the optical component of the multilayered structure of the various material of laminating.
In view of the above problems, the present inventor conducts in-depth research the composition of this tackiness agent, proportioning, found that, utilizes the ultraviolet hardening adhesive compound meeting specified conditions, can solve this problem, thus complete the present invention.
That is, the present invention relates to a kind of optics ultraviolet hardening adhesive compound, it is characterized in that,
Comprise:
Make hydrogenated butadiene polymer polyvalent alcohol, aliphatic polyisocyante and there is (methyl) acrylate reactions of isocyanate group and multifunctional urethane (methyl) acrylate (A) obtained;
Make any at least one in hydrogenated butadiene polymer polyvalent alcohol and aliphatic polyisocyante reaction and the urethane (B1) that obtains and hydrogenated butadiene polymer polyvalent alcohol (B2) (wherein, will (B1) and (B2) merging be called (B));
The carbonatoms of alkyl is simple function (methyl) acrylate (C) of more than 8; And
Photoepolymerizationinitiater initiater (D), and,
Solvent is 100 ~ 10000mPas lower than the viscosity at 1 % by weight, 25 DEG C, and Gardner Color is less than 1.
In addition, the present invention relates to a kind of optics ultraviolet curing adhesive layer, it is characterized in that, obtaining by making the generation ultraviolet curing of above-mentioned optics ultraviolet hardening adhesive compound.
In addition, the present invention relates to a kind of optical component, it is characterized in that, comprise above-mentioned optics ultraviolet curing adhesive layer.
Invention effect
According to the present invention, can widely use as the ultraviolet hardening tackiness agent of the optical applications of the display panel of the multilayered structure be applicable in digital display unit etc.Such as, when being applied to contact panel, during decorative sheet, icon sheet that this panel is fitted or when the transparency carrier being formed with transparency electrode of the contact panel by electrostatic capacitance mode and transparent panel are fitted, can when screening characteristics excellent and not bubbles carry out laminating operation, in addition, the adhesive layer obtained by ultraviolet curing is water white transparency and visible light transmission is excellent, and can play do not peel off, the excellent weather resistance of distortion etc.
Embodiment
As mentioned above, optics ultraviolet hardening adhesive compound (hereinafter referred to as this composition) of the present invention is the composition simultaneously meeting following each condition,
It comprises:
Multifunctional urethane (methyl) acrylate (A) (hereinafter referred to as (A) composition);
Any at least one in urethane (B1) (hereinafter referred to as (B1) composition) and hydrogenated butadiene polymer polyvalent alcohol (B2) (hereinafter referred to as (B2) composition) (it should be noted that, (B1) composition and (B2) composition are merged and is called (B) composition);
The carbonatoms of alkyl is simple function (methyl) acrylate (C) (hereinafter referred to as (C) composition) of more than 8; And
Photoepolymerizationinitiater initiater (D) (hereinafter referred to as (D) composition), and,
Solvent is 100 ~ 10000mPas lower than the viscosity at 1 % by weight, 25 DEG C, and Gardner Color is less than 1.
It should be noted that, in this manual, for the purpose of facility, the ultraviolet curing layer obtained is called this cured layer, and the optical component comprising this cured layer is called this component by this composition.
In above-mentioned each condition, if solvent is more than 1 % by weight, then the composition obtained can bubble when ultraviolet curing, easily in cured layer, produces bubble, likely damages the value of application component, end article.
In above-mentioned each condition, when the scope of 100 ~ 10000mPas is outer, there is the tendency that the coat operations under normal temperature, normal pressure reduces in the viscosity of the composition obtained.
In addition, in above-mentioned each condition, if the tone of the composition obtained exceedes Gardner Color 1, then there is the tendency of the tone of the cured layer obtained, transparency reduction, worry can be limited in the application in optical applications.
As mentioned above, (A) composition is for making hydrogenated butadiene polymer polyvalent alcohol (hereinafter referred to as (a1) composition), aliphatic polyisocyante (hereinafter referred to as (a2) composition) and having (methyl) acrylate (hereinafter referred to as (a3) composition) reaction of isocyanate group and the product that obtains.
(a1) composition is carry out to polybutadiene polyol the polyvalent alcohol that hydrogenation obtains.By being used as (a1) composition of hydride, adhesive power, this composition of excellent durability and this cured layer can be obtained.(a1) molecular weight of composition is not particularly limited, and from the view point of adhesive power, is preferably 1000 ~ 5000.(a1) iodine number of composition is not particularly limited, and is generally less than 50, and from the view point of weather resistance, be preferably less than 25, in addition, hydroxyl value is generally the scope of 10 ~ 200, from the view point of tackiness, is preferably 20 ~ 100.In addition, as the commercially available product corresponding to (a1) composition, such as, can enumerate: " Krasol HLBH-P2000 ", " Krasol HLBH-P3000 " that " NISSO-PB GI-1000 ", " NISSO-PB GI-2000 ", " NISSO-PB GI-3000 " that Tso Tat Co., Ltd., Japan manufactures, CRAY VALLEY company manufacture etc.
As (a2) composition, such as can enumerate: dicyclohexyl methane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate etc., their 2 ~ 6 aggressiveness etc., these (a2) compositions can use with any one form separately, in combination.By using (a2) composition, this cured layer of adhesive power, excellent durability can be provided.
As (a3) composition, such as can enumerate: (methyl) vinylformic acid 2-isocyanatoethyl methacrylate, 1,1-(two acryloyloxymethyl) ethyl vulcabond etc., these can use with any one form separately, in combination.
(A) composition can react to manufacture by making after obtaining C-terminal urethane making (a1) composition and (a2) composition react this C-terminal urethane and (a3) composition.In the manufacture of (A) composition, also the method that (a1) composition, (a2) composition and (a3) composition one are reacted can be adopted, but the viewpoint of the weight-average molecular weight of (A) composition easy to control is set out calmly, preferably adopts the former.
(A) weight-average molecular weight (the polystyrene conversion value obtained by gel permeation chromatography) of composition is not particularly limited, from the view point of tackiness and the weather resistance of this composition obtained, this cured layer, be preferably 10000 ~ 100000.
In addition, the average functional group number of (A) composition is not particularly limited, and from the view point of the weather resistance of this cured layer obtained, is preferably 1.5 ~ 3.0, is more preferably 1.8 ~ 2.2.It should be noted that, this average functional group number refers to the mean number of (methyl) acryl existed in 1 molecule of (A) composition.
About the usage quantity of (A) composition, in this composition 100 weight part, be preferably 10 ~ 50 % by weight, be more preferably 25 ~ 35 % by weight.By the ratio of (A) composition is set as more than 10 % by weight, this composition, the adhesive power of this cured layer, weather resistance can be improved, in addition, by the ratio of (A) composition is set as less than 50 % by weight, the operability of this composition can be improved.
(B) composition is above-mentioned (B1) composition and any at least one in (B2) composition.(B1) composition is the compound identical with the intermediate of (A) composition, and in addition, (B2) composition is equivalent to above-mentioned (a1) composition.
About the usage quantity of (B) composition, in this composition 100 weight part, be preferably 10 ~ 60 % by weight, be more preferably 25 ~ 35 % by weight.By the ratio of (B) composition is set as more than 10 % by weight, this composition, the adhesive power of this cured layer, weather resistance can be improved, in addition, by the ratio of (B) composition is set as less than 60 % by weight, the operability of this composition can be improved.
As the concrete example of (C) composition, can enumerate: (methyl) 2-EHA, (methyl) n-octyl, (methyl) Isooctyl acrylate monomer, (methyl) vinylformic acid ester in the ninth of the ten Heavenly Stems, (methyl) vinylformic acid ester in the different ninth of the ten Heavenly Stems, (methyl) decyl acrylate, (methyl) isodecyl acrylate, (methyl) lauryl acrylate, (methyl) vinylformic acid cetyl, (methyl) stearyl acrylate ester, the different stearyl ester of (methyl) vinylformic acid, (methyl) vinylformic acid mountain Yu ester etc. has (methyl) acrylate of chain-like structure, (methyl) isobornyl acrylate, (methyl) vinylformic acid dicyclopentenyl ester, (methyl) vinylformic acid bicyclopentyl ester, (methyl) vinylformic acid dicyclopentenyl oxygen base ethyl ester, (methyl) vinylformic acid diamantane ester etc. have (methyl) acrylate of ring texture.
In addition, if simple function (methyl) acrylate using the carbonatoms of the alkyl such as (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) n-propyl, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) vinylformic acid n-pentyl ester to be less than 8, then there is the tendency of the tackiness of the adhesive compound obtained, peculiar smell, skin irritation aggravation.
About the usage quantity of (C) composition, in this composition 100 weight part, be preferably the scope of 15 ~ 74.9 % by weight, be more preferably the scope of 30 ~ 70 % by weight.By the ratio of (C) composition is set as more than 15 % by weight, the operability of this composition can be improved, in addition, by the ratio of (C) composition is set as less than 74.9 % by weight, the solidified nature of this composition can be improved.
(D) as long as composition is for decompose by uviolizing and the Photoepolymerizationinitiater initiater producing free radical then can be not particularly limited to use various known material.Specifically, can enumerate: bitter almond oil camphor compound, acetophenone compound, acylphosphine oxide compound, two cyclopentadiene titanium compounds, thioxanthone compounds, the Photoepolymerizationinitiater initiaters such as oxime ester compound, amine, the photosensitizers etc. such as quinone, specifically can enumerate: 2, 2-dimethoxy-1, 2-diphenylethane-1-ketone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-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 propionyl) benzyl] phenyl]-2-methylpropane-1-ketone, 2-methyl isophthalic acid-(4-methyl thio phenyl)-2-morpholino propane-1-ketone, 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl]-1-butanone, 2, 4, 6-trimethyl benzoyl diphenyl base phosphine oxide, two (2, 4, 6-trimethylbenzoyl) phenyl phosphine oxide, two (η
5-2, 4-cyclopentadiene-1-base)-bis-(2, the fluoro-3-of 6-bis-(1H-pyrroles-1-base) phenyl) titanium, 1, 2-octanedione 1-[4-(phenylsulfartyl)-2-(o-benzoyl base oxime)], ethyl ketone 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-base]-1-(adjacent ethanoyl oxime) etc., can be used alone or two or more kinds may be used.Wherein, 1-hydroxycyclohexyl phenyl ketone, TMDPO can improve the solidified nature of this composition further, therefore preferably.
About the usage quantity of (D) composition, in this composition 100 weight part, be preferably 0.1 ~ 10 % by weight, be more preferably 0.2 ~ 5 % by weight.By the ratio of (D) composition is set as more than 0.1 % by weight, the deviation of the solidification polymerization caused by uviolizing can be prevented, in addition, by being set as less than 10 % by weight, can reduce and result from the peculiar smell of resolvent of (D) composition and produce, and the painted of cured layer can be prevented.
The manufacture of this composition is by carrying out above-mentioned (A) ~ (D) composition with the ratio expected mixing.About blending means and the order of addition of each composition, be not particularly limited.
In addition, in the present compositions, various polyfunctional monomer, tackifier can be contained as required in the scope not damaging effect of the present invention.
As the concrete example of above-mentioned polyfunctional monomer, can enumerate: 1,4-butyleneglycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, 1,6-hexylene glycol two (methyl) acrylate, 1,9-nonanediol two (methyl) acrylate etc. have two (methyl) acrylate of aliphatic structure; Cyclohexanedimethanol two (methyl) acrylate, tristane two (methyl) acrylate etc. have 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. have two (methyl) acrylate of aromatic structure; Multifunctional (methyl) acrylate more than trifunctionals such as trimethylolpropane tris (methyl) acrylate, isocyanuric acid ethylene-oxide-modified three (methyl) acrylate, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, Dipentaerythritol Pentaacrylate, dipentaerythritol acrylate.
As the concrete example of above-mentioned tackifier, can enumerate: petroleum resin, resol, xylene resin, coumarone resin, rosin based resin, terpenoid resin, hydrogenated petroleum resin, staybelite resinoid, hydriding terpene resinoid etc.Wherein, preferred hue is the resin of Gardner Color less than 1.As the resin that tone is Gardner Color less than 1, such as, can enumerate: hydrogenated petroleum resin, staybelite resinoid etc.These hydrogenated resins normally tone are the tackifier of Gardner Color less than 1, excellent transparency, therefore, it is possible to improve the transparency of this composition and this cured layer, and polymerization during ultraviolet curing hinders also few, has the advantage that solidified nature is excellent.In addition, for softening temperature, the aniline point (according to Japanese JISK2256) of these tackifier, be not particularly limited, if further consider the transparency of this composition obtained, with the consistency etc. of other each compositions in this composition, then preferably softening temperature is about 80 DEG C ~ about 120 DEG C, aniline point is about 50 DEG C ~ about 100 DEG C.As the commercially available tackifier with tone as above, softening temperature and aniline point, such as, can enumerate: the リ ガ ラ イ ト 5100 etc. that the エ ス コ レ ッ Star 5690 that ア イ マ ー Block S-100, エ Network ソ Application モ ー ビル company that the ア Le コ Application M-90 that Arakawa Chemical Industries, Ltd. manufactures, M-100, M-115, Idemitsu Kosen Co., Ltd. manufacture manufactures, イ ー ス ト マ Application ケ ミ カ Le company manufacture.
In addition, in the present compositions, various additive can be contained as required in the scope not damaging effect of the present invention.Such as, the additives such as surface conditioner, tensio-active agent, UV light absorber, antioxidant, mineral filler, silane coupling agent, colloidal silica, defoamer, wetting agent, rust-preventive agent, stablizer can be contained.
This composition is adapted at being formed with laminating of the transparency carrier of transparency electrode and the laminating of transparent panel and display body and optical functional materials etc. for using in the adhesive material purposes of various optical device, optical component in display panel and decorative sheet, the laminating of icon sheet, contact panel.As the material of above-mentioned component, can enumerate: polyethylene terephthalate, polycarbonate, glass, acrylic resin etc.As display body, can enumerate: on glass, be fitted with the display elements such as the liquid-crystal display of polaroid, EL indicating meter, EL illumination, e-book, plasma display.As optical functional materials, can enumerate: improving visibility, prevent from causing because of external impact transite plate, chilled glass (the anti-film that disperses can be attached with) and the contact panel input pickup etc. such as the acrylic panel for the purpose of the breaking of display element (can one or two sides carry out hard coat process, anti-reflection coating process), polycarbonate plate, polyethylene terephthalate plate, PEN.
As the ultraviolet light source used in the solidification of this composition, can enumerate: the UV irradiation equipment with xenon lamp, high voltage mercury lamp, metal halide lamp.In addition, the conditions such as light quantity, light source, transfer rate suitably regulate, and light quantity is generally about 80W/cm ~ about 160W/cm, and transfer rate is generally about 5m/ minute ~ about 50m/ minute.
In addition, the thickness of this cured layer is not particularly limited, usual average out to about 10 μm ~ about 1000 μm, is preferably 25 ~ 500 μm.By thickness is set as this scope, the shock-resistance of optical component, module can be improved, in addition, can the printing height of absorbing surface poor, therefore, it is possible to use as the protective film of foremost.
Embodiment
Below, the present invention is further illustrated by embodiment.But the present invention is not limited to these embodiments.In addition, in embodiment, in case of no particular description, " % " and " part " refers to " % by weight ".
The synthesis > of < (A) composition
Synthesis example 1
(A-1) synthesis of composition
In the reaction unit with prolong and agitator, add hydrogenated butadiene polymer polyvalent alcohol (Tso Tat Co., Ltd., Japan's manufacture of weight-average molecular weight 4000, trade(brand)name " NISSO-PBGI-3000 ") 910 parts, isophorone diisocyanate 81 parts and stannous octoate 0.2 part, be warming up to 80 DEG C and be incubated 2 hours, then, measured by NCO and confirm that reaction terminates, obtain the C-terminal oligourethane as intermediate.Then, add methacrylic acid 2-isocyanatoethyl methacrylate 19 parts, 2 hours are incubated at 80 DEG C, then, measured by NCO and confirm that reaction terminates, thus, the urethane methacrylate oligopolymer (hereinafter referred to as (A-1) composition) of weight-average molecular weight 36000, average functional group number 2.0 is obtained.It should be noted that, this weight-average molecular weight is the polystyrene conversion value obtained by gel permeation chromatography, this condition determination [determinator main body (goods name " HLC-8220GPC ", TOSOH Co., Ltd manufacture), post (goods name " TSKGel G1000H ", " TSKGel G2000H ", TOSOH Co., Ltd manufacture), developing solvent (tetrahydrofuran (THF))] as described below.(lower same)
Synthesis example 2
(A-2) synthesis of composition
In the reaction unit identical with synthesis example 1, add and the identical hydrogenated butadiene polymer polyvalent alcohol 925 parts used in synthesis example 1, isophorone diisocyanate 51 parts and stannous octoate 0.2 part, be warming up to 80 DEG C and be incubated 2 hours, then, measured by NCO and confirm that reaction terminates, obtain the C-terminal oligourethane as intermediate.Then, add methacrylic acid 2-isocyanatoethyl methacrylate 24 parts, 2 hours are incubated at 80 DEG C, measured by NCO and confirm that reaction terminates, thus, the urethane methacrylate oligopolymer (hereinafter referred to as (A-2) composition) of weight-average molecular weight 21000, average functional group number 2.0 is obtained.
Synthesis example 3
(A-3) synthesis of composition
In the reaction unit identical with synthesis example 1, add and the identical hydrogenated butadiene polymer polyvalent alcohol 917 parts, the dicyclohexyl methyl hydride-4 that use in synthesis example 1,4 '-vulcabond 67 parts and stannous octoate 0.2 part, be warming up to 80 DEG C and be incubated 2 hours, then, measured by NCO and confirm that reaction terminates, obtain the C-terminal oligourethane as intermediate.Then, add methacrylic acid 2-isocyanatoethyl methacrylate 16 parts, 2 hours are incubated at 80 DEG C, measured by NCO and confirm that reaction terminates, thus, the urethane methacrylate oligopolymer (hereinafter referred to as (A-3) composition) of weight-average molecular weight 21000, average functional group number 2.0 is obtained.
Relatively synthesis example 1
(E-1) synthesis of composition
In the reaction unit identical with synthesis example 1, add polypropylene glycol (Asahi Glass Co., Ltd's manufacture of weight-average molecular weight 4000, trade(brand)name " PREMINOL 5001F ") 955 parts, isophorone diisocyanate 34 parts and stannous octoate 0.2 part, be warming up to 80 DEG C and be incubated 2 hours, then, measured by NCO and confirm that reaction terminates, obtain the C-terminal oligourethane as intermediate.Then, add methacrylic acid 2-isocyanate 19 parts, 2 hours are incubated at 80 DEG C, measured by NCO and confirm that reaction terminates, thus, the urethane methacrylate oligopolymer (hereinafter referred to as (E-1) composition) of weight-average molecular weight 36000, average functional group number 2.0 is obtained.
The synthesis > of < (B) composition
Synthesis example 4
(B-1) synthesis of composition
In the reaction unit identical with synthesis example 1, add and the identical hydrogenated butadiene polymer polyvalent alcohol 964 parts used in synthesis example 1, isophorone diisocyanate 36 parts and stannous octoate 0.2 part, be warming up to 80 DEG C and be incubated 2 hours, then, measured by NCO and confirm that reaction terminates, obtain the urethane (hereinafter referred to as (B-1) composition) of weight-average molecular weight 9900.
Synthesis example 5
(B-2) synthesis of composition
In the reaction unit identical with synthesis example 1, add and the identical hydrogenated butadiene polymer polyvalent alcohol 942 parts used in synthesis example 1, isophorone diisocyanate 58 parts and stannous octoate 0.2 part, be warming up to 80 DEG C and be incubated 2 hours, then, measured by NCO and confirm that reaction terminates, obtain the urethane (hereinafter referred to as (B-2) composition) of weight-average molecular weight 34000.
Relatively synthesis example 2
(E-2) synthesis of composition
In the reaction unit identical with synthesis example 1, add and compare the identical polypropylene glycol 955 parts, isophorone diisocyanate 34 parts and the stannous octoate 0.2 part that use in synthesis example 1, be warming up to 80 DEG C and be incubated 2 hours, then, measured by NCO and confirm that reaction terminates, obtain the urethane (hereinafter referred to as (E-2) composition) of weight-average molecular weight 34000.
The preparation > of < adhesive compound
Embodiment 1
By (A-1) composition 30 parts, as hydrogenated butadiene polymer polyvalent alcohol (Tso Tat Co., Ltd., Japan's manufacture of (B) composition, trade(brand)name " NISSO-PB GI-1000 ", hereinafter referred to as (B-3) composition) 27 parts, as isobornyl acrylate (Osaka organic chemistry Co., Ltd. manufacture of (C) composition, trade(brand)name " IBXA ", hereinafter referred to as (C-1) composition) 10 parts, (Mitsubishi chemical Co., Ltd manufactures 2-EHA, trade(brand)name " 2-EHA (ア Network リ Le acid 2-エ チ Le ヘ キ シ Le) ", hereinafter referred to as (C-2) composition) 45 parts and (BASF Amada Co., Ltd. manufactures as the 1-hydroxycyclohexyl phenyl ketone of (D) composition, trade(brand)name " イ Le ガ キ ュ ア 184 ", hereinafter referred to as (D-1) composition) 3 parts all carry out converting coordinating with purity, prepare adhesive compound (with reference to table 1).In addition, evaluate the Gardner Color of said composition, viscosity, solvent containing ratio and consistency, show the result in table 2 (lower same).
Embodiment 2 ~ 7
As shown in table 1, change the kind of each composition, according to the method identical with embodiment 1, prepare adhesive compound.
Comparative example 1
Do not use (B) composition, (A-1) composition 57 parts, (C-1) composition 10 parts, (C-2) composition 30 parts and (D-1) composition 3 parts are all carried out converting coordinating with purity, according to the method identical with embodiment 1, prepare adhesive compound (with reference to table 1, lower with).
Comparative example 2
Do not use (B) composition, (A-2) composition 57 parts, (C-1) composition 10 parts, (C-2) composition 30 parts and (D-1) composition 3 parts are all carried out converting coordinating with purity, prepares adhesive compound.
Comparative example 3
Do not use (A) composition, (B-1) composition 57 parts, (C-1) composition 10 parts, (C-2) composition 30 parts and (D-1) composition 3 parts are all carried out converting coordinating with purity, prepares adhesive compound.
Comparative example 4
Do not use (A) composition, (B-2) composition 57 parts, (C-1) composition 10 parts, (C-2) composition 30 parts and (D-1) composition 3 parts are all carried out converting coordinating with purity, prepares adhesive compound.
Comparative example 5
Do not use (A) composition, (B-3) composition 57 parts, (C-1) composition 10 parts, (C-2) composition 30 parts and (D-1) composition 3 parts are all carried out converting coordinating with purity, prepares adhesive compound.
Comparative example 6
By A-1) composition 30 parts, (B-3) composition 27 parts, replace (C) composition butyl acrylate (Mitsubishi chemical Co., Ltd manufacture, trade(brand)name " butyl acrylate (ア Network リ Le acid Block チ Le) ", hereinafter referred to as (F-1) composition) 40 parts and (D-1) composition 3 parts all carry out converting coordinating with purity, prepares adhesive compound.
Comparative example 7
(E-1) composition 30 parts of (A) composition will be replaced, replace (E-2) composition 27 parts of (B) composition, (C-1) composition 10 parts, (C-2) composition 30 parts and (D-1) composition 3 parts all to carry out converting coordinating with purity, prepare adhesive compound.
Table 1
(B-3): hydrogenated butadiene polymer polyvalent alcohol
(Tso Tat Co., Ltd., Japan manufactures, trade(brand)name " NISSO-PB GI-1000 ")
(B-4): hydrogenated butadiene polymer polyvalent alcohol
(Tso Tat Co., Ltd., Japan manufactures, trade(brand)name " NISSO-PB GI-3000 ")
(C-1): isobornyl acrylate (Osaka organic chemistry Co., Ltd. manufactures, trade(brand)name " IBXA ")
(C-2): 2-EHA (Mitsubishi chemical Co., Ltd manufactures, trade(brand)name " ア Network リ Le acid 2-エ チ Le ヘ キ シ Le ")
(C-3): (methyl) vinylformic acid dicyclopentenyl oxygen base ethyl ester (Hitachi Chemical Co., Ltd. manufactures, trade(brand)name " Off ァ Application Network リ Le FA512AS ")
(D-1): 1-hydroxycyclohexyl phenyl ketone (BASF Amada Co., Ltd. manufactures, trade(brand)name " イ Le ガ キ ュ ア 184 ")
(F-1): butyl acrylate (Mitsubishi chemical Co., Ltd manufactures, trade(brand)name " ア Network リ Le acid Block チ Le ")
Table 2
< Gardner Color >
Gardner Color measures according to Japanese JIS K5600.
< viscosity >
Viscosity (mPas) utilizes E type viscometer { TVE-10 (Toki Sangyo Co., Ltd.'s manufacture) } to measure under the condition of 25 DEG C, 5 minutes.
< solvent containing ratio >
About solvent containing ratio, gas phase chromatographic device is used to measure under the following conditions.
(analytical equipment)
GC:Agilent 6850 (manufacture of ア ジ レ Application ト テ Network ノ ロ ジ ー Co., Ltd.)
(GC condition determination)
GC post: 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)
Post flow: 2.0ml/ minute
Carrier gas: helium
Sample injection method: shunting (50:1)
Detected temperatures: 300 DEG C
< consistency >
About consistency, the adhesive compound that visual observation obtains, judges based on following benchmark.
Zero: evenly, completely transparent
×: confirm gonorrhoea, sediment, insolubles or liquid layer be separated in any one
The making > of < test film
The composition of embodiment 1 is fitted between the thick sheet glass of 0.7mm and the thick sheet glass of 0.7mm in the mode of the thickness becoming 100 μm, makes it from metal halide lamp (1000mJ/cm
2) under by 3 times, make it solidify thus, make test film.For the composition of embodiment 2 ~ 7 and comparative example 1 ~ 7, also make test film in the same way.
[the various evaluations of adhesive layer]
Evaluation Example 1 ~ 7, comparative evaluation example 1 ~ 7
Use above-mentioned test film, implement following test.
< haze value, transmissivity >
Use colored haze meter (カ ラ ー へ イ ズ メ ー タ ー, in village, color technical institute manufactures), measure haze value and the transmissivity of above-mentioned test film according to Japanese JIS K5600.Show the result in table 3.It should be noted that, each haze value is the numerical value of the haze value of the glass comprised as base material.
< oven test >
In oven test, after above-mentioned test film is left standstill 500 hours in the constant temperature and humidity cabinet of temperature 85 DEG C, by measuring haze value and transmissivity with aforementioned same method.Show the result in table 3.It should be noted that, each haze value is the numerical value of the haze value of the glass comprised as base material.
In addition, weather resistance is evaluated based on following benchmark.
Zero: without stripping, the leaching of glue-free adhesion coating, bubble-free and breakage
×: there is stripping, have adhesive layer to leach, have bubble and breakage
< hot resistance test >
In hot resistance test, after above-mentioned test film is left standstill 500 hours in the constant temperature and humidity cabinet of temperature 85 DEG C, humidity 85%, by measuring haze value and transmissivity with aforementioned same method.Show the result in table 4.It should be noted that, each haze value is the numerical value of the haze value of the glass comprised as base material.
In addition, weather resistance is evaluated based on following benchmark.
Zero: without stripping, the leaching of glue-free adhesion coating, bubble-free and breakage
×: there is stripping, have adhesive layer to leach, have bubble and breakage
Table 3
Table 4
Claims (6)
1. an optics ultraviolet hardening adhesive compound, is characterized in that,
Comprise:
Make hydrogenated butadiene polymer polyvalent alcohol, aliphatic polyisocyante and there is (methyl) acrylate reactions of isocyanate group and multifunctional urethane (methyl) acrylate (A) obtained;
Make any at least one in hydrogenated butadiene polymer polyvalent alcohol and aliphatic polyisocyante reaction and the urethane (B1) that obtains and hydrogenated butadiene polymer polyvalent alcohol (B2), wherein, (B1) and (B2) merging is called (B);
The carbonatoms of alkyl is simple function (methyl) acrylate (C) of more than 8; And
Photoepolymerizationinitiater initiater (D), and,
Solvent is 100 ~ 10000mPas lower than the viscosity at 1 % by weight, 25 DEG C, and Gardner Color is less than 1.
2. optics ultraviolet hardening adhesive compound according to claim 1, wherein, the weight-average molecular weight of described (A) composition is 10000 ~ 100000, and described weight-average molecular weight is the polystyrene conversion value obtained by gel permeation chromatography.
3. optics ultraviolet hardening adhesive compound according to claim 1 and 2, wherein, the average functional group number of described (A) composition is 1.5 ~ 3.0.
4. the ultraviolet hardening adhesive compound of the optics according to any one of claims 1 to 3, wherein, each content of described (A), (B), (C) and (D) composition is followed successively by 10 ~ 50 % by weight, 5 ~ 30 % by weight, 5 ~ 74.9 % by weight and 0.1 ~ 10 % by weight, adds up to 100 % by weight.
5. an optics ultraviolet curing adhesive layer, is characterized in that, obtains by making the optics ultraviolet hardening adhesive compound generation ultraviolet curing according to any one of Claims 1 to 4.
6. an optical component, is characterized in that, comprises optics ultraviolet curing adhesive layer according to claim 5.
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| JP2014-021342 | 2014-02-06 | ||
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| JP (1) | JP6414479B2 (en) |
| KR (1) | KR102200661B1 (en) |
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| CN104830266B (en) | 2019-05-07 |
| JP2015165014A (en) | 2015-09-17 |
| KR102200661B1 (en) | 2021-01-08 |
| KR20150093120A (en) | 2015-08-17 |
| TW201531543A (en) | 2015-08-16 |
| JP6414479B2 (en) | 2018-10-31 |
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