CN104073036A - Active energy ray-curable composition and component with cured coating - Google Patents
Active energy ray-curable composition and component with cured coating Download PDFInfo
- Publication number
- CN104073036A CN104073036A CN201410114247.6A CN201410114247A CN104073036A CN 104073036 A CN104073036 A CN 104073036A CN 201410114247 A CN201410114247 A CN 201410114247A CN 104073036 A CN104073036 A CN 104073036A
- Authority
- CN
- China
- Prior art keywords
- methyl
- coating film
- active energy
- hardened coating
- energy ray
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymerisation Methods In General (AREA)
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Abstract
The invention provides an active energy ray-curable composition which can form a cured coating with excellent transparency, easy sliding and no easy damage, and a component with the cured coating. The active energy ray-curable composition of the invention comprises the components of: relative to 100 by mass percent of an active energy-ray-curable component (B), and more than 0.01 by mass percent and less than 3 by mass percent of paraffin wax or polyolefin (A) which has a number-average average molecular weight between 320 and 1000 and is liquid at a temperature below 25 DEG C.
Description
Technical field
The present invention relates to a kind of active energy ray curable adhensive compositions and possess the member of hardened coating film that uses said composition.
Background technology
Compare with heat embrittlement type film, the sclerosis of curable with actinic energy ray film is fast and productivity is good, and high rigidity and scuff resistance also excellent, therefore universal rapidly.
Following technology is for example disclosed: be that 125 DEG C of above and particle diameters are wax (wax) composition below 0.1 μ m by containing fusing point, and wish forms scoring resistance or traumatic resistance excellence and is difficult to the film (patent documentation 1) sliding.
In addition although technical field is different from curable with actinic energy ray film, the technology that contains specific paraffin (paraffin) in the means of dealing with problems in aftermentioned is disclosed in patent documentation 2.In more detail, can harden in air and the required performance of biaxiality film (the 6th section) in the polymerizable liquid crystal compound of problem such as front phase differential is fully large to provide, about an example of the preferred compound containing in order to obtain good planar orientation (planar orientation) rapidly in when coating (polyethylene, polypropylene, polyisobutene, paraffin, mobility paraffin, Chlorinated Polypropylene III, clorafin, imported the compound of fluorine atom), paraffin, mobility paraffin (the 90th section, the 92nd section) are recorded.
[prior art document]
[patent documentation]
[patent documentation 1] Japanese Patent Laid-Open 2002-121247 communique
No. 2010/095680th, [patent documentation 2] International Publication
In recent years, as the various indicating meters in smart mobile phone (smartphone), portable terminal, PC (personal computer), household appliances etc., touch-screen (touch screen panel) starts universal rapidly.Therefore,, for the most surface of touch-screen, require transparency excellence and there is the scuff resistance of height or high hardness, and further requiring the characteristic that finger sliding is good.
But although former curable with actinic energy ray film has the scuff resistance of height or high hardness, the frictional coefficient on hardening thing surface is high, has the problem of being obstructed while making finger sliding.
The object of the invention is to solve the problem of described prior art, a kind of active energy ray curable adhensive compositions is provided, and described active energy ray curable adhensive compositions can form that the transparency is excellent and finger sliding (the low characteristic of resistance while making finger sliding) excellent and the hardened coating film of easy damaged not.
Summary of the invention
The present invention relates to a kind of active energy ray curable adhensive compositions, with respect to active energy ray hardening compound (B) 100 mass parts, contain paraffin or polyolefine (A) with the scope more than 0.01 mass parts, below 3 mass parts, the number average molecular weight of described paraffin or polyolefine (A) is more than 320 and below 1000, and at 25 DEG C, is liquid.
The present invention relates to a kind of member with hardened coating film, it is being selected from least a portion of at least one member in glass, plastics, metal, Wood member and paper, the hardened coating film being formed is set forms by described active energy ray curable adhensive compositions of the present invention.
[effect of invention]
Active energy ray curable adhensive compositions of the present invention can form the excellent and also excellent hardened coating film of easy damaged and then finger sliding (low resistance while making finger sliding) not of the transparency.
Embodiment
To number average molecular weight used in the present invention be more than 320 and 1000 following and at 25 DEG C paraffin or the polyolefine (A) for liquid be illustrated.This paraffin or polyolefine (A) are as hardened coating film being given to the composition of good sliding, i.e. sliding imparting agent and bring into play function, therefore sometimes also referred to as sliding imparting agent (A).The number average molecular weight of sliding imparting agent (A) is 320～1000 (comprising higher limit, lower value (following identical)) preferably, more preferably 350～1000, and then preferably 400～1000.
Sliding imparting agent (A) is liquid at 25 DEG C, and number average molecular weight is in described scope, can form thus the hardened coating film of transparency excellence, not easy damaged and finger sliding excellence.
If sliding imparting agent (A) is solid at 25 DEG C, the tendency that has the finger sliding of hardened coating film to reduce.
If the number average molecular weight of sliding imparting agent (A) is less than 320, there is following tendency:, sliding imparting agent (A) too good with the consistency of aftermentioned active energy ray hardening compound (B) do not float up on the surface of hardened coating film, and finger sliding reduces.On the other hand, if the number average molecular weight of sliding imparting agent (A) exceedes 1000, may reduce with the consistency of aftermentioned active energy ray hardening compound (B), occur to separate and cannot obtain uniform masking liquid, or sliding imparting agent (A) floats to hardened coating film surface with " drop " shape.
This sliding imparting agent (A) possesses set molecular weight and structure and state, as long as can form the excellent and hardened coating film of easy damaged and then finger sliding excellence not of the transparency, is not particularly limited.
Number average molecular weight be more than 320 and 1000 following and at 25 DEG C paraffin or the polyolefine (A) for liquid for example can illustrate following material.
This paraffin can be enumerated: Song Cunbai (Moresco-White) P-80 (Song Cun (MORESCO) company manufactures: number average molecular weight is 400), Song Cunbai (Moresco-White) P-120 (Song Cun (MORESCO) company manufactures: number average molecular weight is 470), Song Cunbai (Moresco-White) P-260 (Song Cun (MORESCO) company manufactures: number average molecular weight is 550) etc.And then also can illustrate the hydrogenation iso-butylenes (isobutene) such as Pa Limu 6 (Parleam6) (You company manufacture: number average molecular weight is 350).
Polyolefine can be enumerated as not Lip river (Versaflow) LV (three leaf science and technology (Shamrock) companies manufacture: number average molecular weight is 890) etc. of poly Vaasa.
Particularly preferably polyvinyl compound of sliding imparting agent (A).
Sliding imparting agent (A) can use separately also can mix use two or more, also paraffin can be mixed to use with polyolefine.
In addition, about the number average molecular weight described in the present invention, use gel permeation chromatograph (gel permeation chromatograp hy, GPC) (HLC-8220GPC: Dong Cao company manufactures), 3 endowels (TSK-gel Super HM-H: Dong Cao company manufactures), by tetrahydrofuran (THF) (Tetrahydrofuran, THF) as developing solvent, under the condition that is 0.6mL/min at 40 degree Celsius, flow, measure, calculate the molecular weight that polystyrene standard converts.
Curable adhensive compositions of the present invention contains at least one sliding being selected from paraffin or polyolefine gives Liu (A) and active energy ray hardening compound (B) (being also denoted as simply below " hardening compound (B) ").Below, hardening compound (B) is illustrated.
Hardening compound (B) is the so-called polyfunctional compound of main use preferably, can form traumatic resistance (scuff resistance), solvent resistance excellence and tough hardened coating film, described polyfunctional compound has 2 above ethene unsaturated double-bonds that contribute to sclerosis, particularly preferably is and has 3 above ethene unsaturated double-bonds.In this case, also can assist the compound that uses simple function.The preferred acryl of ethene unsaturated double-bond, methacryloyl, particularly preferably acryl.Hardening compound (B) also can use following illustrative compound multiple combination.Below, active energy ray hardening compound (B) is illustrated.
In hardening compound (B), polyfunctional concrete example can be enumerated: dihydroxymethyl tristane diacrylate, (ethoxylation) bisphenol a diacrylate, (propoxylation) bisphenol a diacrylate, cyclohexane dimethanol diacrylate, (gathering) glycol diacrylate, (ethoxylation) 1,6 hexanediol diacrylate, (propoxylation) 1,6 hexanediol diacrylate, (ethoxylation) neopentylglycol diacrylate, (propoxylation) neopentylglycol diacrylate, 3-hydroxypivalic acid neopentylglycol diacrylate, tetramethylolmethane three (methyl) acrylate, tetramethylolmethane four (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, oxyethane upgrading trimethylolpropane tris (methyl) acrylate, propylene oxide upgrading trimethylolpropane tris (methyl) acrylate, three (acryloxy ethyl) isocyanuric acid ester, caprolactone upgrading three (acryloxy ethyl) isocyanuric acid ester, trimethylolethane trimethacrylate (methyl) acrylate, Dipentaerythritol four (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, alkyl upgrading Dipentaerythritol three (methyl) acrylate, alkyl upgrading Dipentaerythritol four (methyl) acrylate, alkyl upgrading Dipentaerythritol five (methyl) acrylate, caprolactone upgrading Dipentaerythritol six (methyl) acrylate, the polyvalent alcohols such as 1,2,3-hexanaphthene four (methyl) acrylate and (methyl) acrylic acid ester cpds,
Polyurethane(s) gathers (methyl) acrylate, polyester gathers (methyl) acrylate, polyethers gathers (methyl) acrylate, polyacrylic acid gathers (methyl) acrylate, poly-(methyl) acrylate of polyalcohols acid, poly-(methyl) acrylate of poly-epoxy, poly-(methyl) acrylate of poly-spiral shell acetal, polyhutadiene gathers (methyl) acrylate, polythiol polyenoid gathers (methyl) acrylate, polyfunctional poly-(methyl) acrylic compound such as poly-(methyl) acrylate of polysilicon,
By the ester cpds of polyvalent alcohol and polyprotonic acid and (methyl) vinylformic acid synthesized, for example, by ester cpds of trimethylolethane/succsinic acid/vinylformic acid=2/1/4 (mol ratio) synthesized etc.
In hardening compound (B); from the viewpoint of obdurability, scuff resistance; can suitably use and there is poly-(methyl) esters of acrylic acid such as poly-(methyl) acrylate of polyurethane(s) of 6 above functional groups, poly-(methyl) acrylate of poly-epoxy, and in molecule, there is the polyfunctional acrylic ester class of 4 above acryls.
Poly-(methyl) acrylate of described poly-epoxy is for example to make the epoxy reaction of (methyl) acrylic acid carboxyl and epoxy resin and import (methyl) acryl and form, and can enumerate (methyl) vinylformic acid affixture of phenolic resin varnish type epoxy resin etc.
Poly-(methyl) acrylate of described polyurethane(s) for example has: (i) make polymeric polyisocyanate react poly-(methyl) acrylate of polyurethane(s) of gained with (methyl) esters of acrylic acid with hydroxyl; And (ii) polyvalent alcohol is reacted under the condition of isocyanato surplus with polymeric polyisocyanate, form the urethane polymer of isocyanato group containing, (methyl) esters of acrylic acid that makes to have hydroxyl reacts with the urethane polymer of described isocyanato group containing and the polyurethane(s) that obtains gathers (methyl) acrylate.In addition, (iii) also can make polyvalent alcohol react under the condition of hydroxyl surplus with polymeric polyisocyanate and form the urethane polymer of hydroxyl, (methyl) esters of acrylic acid that makes to have isocyanato reacts with the urethane polymer of described hydroxyl and obtains poly-(methyl) acrylate of polyurethane(s).
Described polyvalent alcohol can be enumerated: ethylene glycol, propylene glycol, Diethylene Glycol, dipropylene glycol, butyleneglycol, 1,6-hexylene glycol, 3-methyl isophthalic acid, the polycondensate of 5-pentanediol, neopentyl glycol, hexanetriol, TriMethylolPropane(TMP), polytetramethylene glycol, hexanodioic acid and ethylene glycol etc.
Described polymeric polyisocyanate can be enumerated: tolylene diisocyanate, Xylene Diisocyanate, hydrogenated xylene diisocyanate, ditan-4,4 '-vulcabond, hydrogenation ditan-4,4 '-vulcabond, norbornane-vulcabond, isophorone diisocyanate, hexamethylene diisocyanate etc.In addition, also can use the trimethylolpropane adduct of described diisocyanate cpd, react with water gained biuret (biuret) body, there is trimer of isocyanuric acid ester ring etc.
Described (methyl) esters of acrylic acid with hydroxyl can be enumerated: 2-Hydroxy ethyl acrylate, 2-hydroxypropyl acrylate, vinylformic acid-4-hydroxyl butyl ester, pentaerythritol triacrylate, Dipentaerythritol five acrylate, two-trimethylolpropane tetra-acrylate etc.
Described (methyl) esters of acrylic acid with isocyanato can be enumerated: (methyl) acryloxy ethyl isocyanate, (methyl) acryloxy propyl group isocyanic ester, (methyl) acryl isocyanic ester etc.
Curable adhensive compositions of the present invention is as follows: with respect to hardening compound (B) 100 mass parts, contain sliding imparting agent (A) with the scope of 0.01 mass parts～3 mass parts, be preferably and contain 0.02 mass parts～1.5 mass parts, more preferably contain 0.1 mass parts～0.5 mass parts.If be less than 0.01 mass parts, effect deficiency that may finger sliding, if exceed 3 mass parts, can be detrimental to as fundamental propertys such as the traumatic resistance of hardened coating film, the transparency, adhesions.
Curable adhensive compositions of the present invention is to harden by irradiation ultraviolet radiation, electron beam isoreactivity energy line.In the situation that hardening by uviolizing, curable adhensive compositions contains photopolymerization initiator.
Photopolymerization initiator is not particularly limited, for example, can enumerate: acetophenones, st-yrax class, benzophenone, phosphine oxide class, ketal class, Anthraquinones, thioxanthones etc.Specifically can enumerate: benzoin methyl ether, Benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, diethoxy acetophenone, benzil dimethyl ketal, 2-hydroxy-2-methyl Propiophenone (2-hydroxy-2-methylpropiophenone), 1-hydroxycyclohexylphenylketone, benzophenone, 2; 4; 6-trimethylbenzoyl diphenyl phosphine oxide, meter Qi Le ketone, N; N-dimethylaminobenzoic acid isopentyl ester, 2-chlorothiaxanthenone, 2,4-diethyl thioxanthone etc.Photopolymerization initiator can be used alone also can be used together two or more.
From guaranteeing suitable cross-linking density and the viewpoint of painting property firmly, in the total amount 100 quality % of described sliding imparting agent (A), active energy ray hardening compound (B) and photopolymerization initiator, be preferably the described photopolymerization initiator that contains 0.1 quality %～20 quality %, more preferably 1 quality %～15 quality %.
In view of the convenience of coating, curable adhensive compositions of the present invention can contain solvent.; drying property when solvent is viscosity in order to adjust curable adhensive compositions (also referred to as masking liquid or coating composition) or leveling property (leveling) or coating and using, as long as according to optionally appropriate allotments such as the coating processes of curable adhensive compositions.Therefore, the solids component of curable adhensive compositions is not particularly limited, for example, can be set as 20 quality %～100 quality %.
The kind of solvent is not particularly limited, and can illustrate following solvent.Solvent can be used singly or in combination multiple.
Ether series solvent can be enumerated: dibutyl ether, glycol dimethyl ether, diethoxyethane, propylene oxide, Isosorbide-5-Nitrae-dioxan, 1,3-dioxolane, 1,3,5-trioxane, tetrahydrofuran (THF), methyl-phenoxide, phenyl ethyl ether etc.
Ketone series solvent can be enumerated: acetone, methyl ethyl ketone, metacetone, butyrone, diisobutyl ketone, methyl iso-butyl ketone (MIBK), methyln-hexyl ketone, 2 pentanone, methyl-n-butyl ketone, cyclopentanone, pimelinketone, methylcyclohexanone, methyl ethyl diketone, 1,2-diacetoxy acetone etc.
Ester series solvent can be enumerated: ethyl formate, propyl formate, pentyl formate, methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate, gamma-butyrolactone, 2-methoxy menthyl acetate, 2-ethoxy acetate, 2-ethoxy ethyl acetate, 2-ethoxyl ethyl propionate, isobutyl acetate, methyl acetoacetate, methyl aceto acetate etc.
Alcohol series solvent can be enumerated: methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, hexalin, 2-methyl cellosolve, 2-propoxy-ethanol, butoxy ethanol, diacetone alcohol etc.
Stable hydrocarbon series solvent can be enumerated: hexane, heptane, octane, hexanaphthene, methylcyclohexane, ethylcyclohexane etc.
Aromatic series series solvent can be enumerated: benzene,toluene,xylene etc.
Glycol series solvent can be enumerated: ethylene glycol ethyl ether, glycol isopropyl ether, butyl glycol ether, propylene glycol monomethyl ether, ethyl carbitol, diethylene glycol monobutyl ether etc.
In curable adhensive compositions of the present invention, optionally can, not hindering in the scope of effect of the present invention, further suitably add more than one of light sensitizer, photostabilizer, UV light absorber, catalyzer, tinting material, leveling agent, defoamer, polymerization promotor, antioxidant, fire retardant, infrared absorbent, interfacial agent, surface modifier, thixotropic agent etc.
Curable adhensive compositions of the present invention is applied on various members, after being dried, irradiates active energy ray in the situation that containing organic solvent, can form thus hardened coating film.
From guaranteeing pencil hardness and wearability, avoid in addition reducing with the adhesion of member or hardened coating film in produce the viewpoint in crack, the thickness of hardened coating film is 3 μ m～20 μ m preferably, more preferably 4 μ m～15 μ m, and then preferred 4 μ m～10 μ m.
The member that is used for arranging hardened coating film is not particularly limited, for example, can from the cohort being made up of glass, plastics, metal, Wood member, paper and pottery, carbon fiber, suitably select.And then, also can select the composite component being formed by multiple members.These members can be film, paper smooth shape like that, also can be three-dimensional shape.
Preferably transparent film of plastic film.
The starting material of described plastics for example can be enumerated: the transparent polymers such as polyester based polymer, cellulose-based polymkeric substance, polycarbonate based polymer, acrylic acid polymer.
Described polyester based polymer can be enumerated polyethylene terephthalate (Polyethylene terephthalate, PET), Polyethylene Naphthalate etc.Cellulose-based polymkeric substance can be enumerated diacetyl cellulose, triacetyl cellulose (Triacetyl cellulose, TAC) etc.Acrylic acid polymer can be enumerated polymethylmethacrylate etc.
The starting material of described plastics also can be enumerated: the transparent polymers such as styrenic, olefin polymer, vinyl chloride-based polymer and acid amides based polymer.
Described styrenic can be enumerated polystyrene, acrylonitritrile-styrene resin etc.Olefin polymer can be enumerated: polyethylene, polypropylene, have polyolefine, the ethylene-propylene copolymer etc. of ring-type or norbornylene structure.Acid amides based polymer can be enumerated nylon or aromatic polyamide etc.
And then the starting material of described plastics also can be enumerated: the transparent polymers such as the adulterant of imide series polymkeric substance, sulfone based polymer, polyethersulfone based polymer, polyetherketone based polymer, polyphenylene sulfide (polyphenyl sulfide) based polymer, vinyl alcohol system polymer, vinylidene chloride based polymer, polyvinyl butyral based polymer, aromatic ester based polymer, polyoxymethylene (polyoxymethylene) based polymer and epoxy based polymer and described polymkeric substance etc.Especially can suitably use the polymkeric substance that double refraction is few.
In the situation that using plastic film as member, also can use the so-called easily film of adhesion type,, forming on the face of hardened coating film, being provided with and being selected from acrylic resin, polyester copolymerization is that resin, polyurethane(s) are the film of the resin layer in the cohort of resin, styrene-maleic acid grafted polyester resin and acrylic acid series grafted polyester resin etc.
In member, the thickness of the member of even shape can suitably determine, in the situation of plastic film, and conventionally from the aspect such as workability, thin layer of intensity or operation etc., preferably 10 μ m～500 μ m left and right.Particularly preferably 20 μ m～300 μ m, more preferably 30 μ m～200 μ m.In the situation that member is three-dimensional shape, thickness indefinite.
As long as the coating of curable adhensive compositions utilizes usual method, as long as for example utilize, excellent painting method (bar coat method), cutter painting method (knife coat method), rolling method (roll coat method), scraper for coating method (blade coat method), mould are coated with method (die coat method), intaglio plate coating method (gravure coat method) is coated with.In the situation that containing solvent, preferably, after coating curable adhensive compositions, make film dry under 50 DEG C～150 DEG C left and right.
As mentioned above, the sclerosis of the curable adhensive compositions after coating can be undertaken by irradiating active energy ray.Active energy ray can be enumerated ultraviolet ray, electron beam etc.Using in ultraviolet situation, use the light sources such as high pressure mercury vapour lamp, electrodeless lamp, xenon lamp, ultraviolet irradiation amount is preferred 100mJ/cm for example
2～2000mJ/cm
2left and right.The finger sliding excellence of the hardened coating film of gained.
According to active energy ray curable adhensive compositions of the present invention, can provide the hardened coating film that has finger sliding (low resistance while making finger sliding) and scuff resistance and high rigidity concurrently.
[embodiment ］
Below, by embodiment, the present invention is illustrated.In addition,, in embodiment, " part ", " % " refer to respectively " mass parts ", " quality % ".
(embodiment 1)
With respect to (the trade(brand)name: " sub-Luo Nisi (Aronix) M305 " of the pentaerythritol triacrylate as hardening compound (B), East Asia Synesis Company manufactures) 100 parts, mix 0.5 part of the hydrogenation iso-butylene that is 350 as the number average molecular weight of paraffin (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufactures), as 5 parts of the Yi Luka (Irgacure) 184 (manufacture of Ciba (Ciba Specialty Chemicals) company) of photopolymerization initiator, and as 101.5 parts of the ethyl acetate of solvent, the curable adhensive compositions (also referred to as coating composition or masking liquid) that acquisition nonvolatile component is 50%.
Use excellent painting machine that said composition is coated on to the polyethylene terephthalate film through the easy bonding processing in surface that thickness is approximately 100 μ m (trade(brand)name: " Coase is (Cosmoshine) A4100 not still ", Japan spin company manufacture) easy to be bonding treated side on, utilize hot-air oven by after removal of solvents, use and be output as 80W/cm
2high pressure mercury vapour lamp with 400mJ/cm
2irradiation ultraviolet radiation, makes to be coated with membrane fussion sclerosis, obtains and has the member with hardened coating film that dry film thickness is the coating of approximately 6 μ m.
(embodiment 2～embodiment 3)
The hydrogenation iso-butylene that is 350 by the number average molecular weight that uses 0.5 part in embodiment 1 (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufactures) uses 1.5 parts of (embodiment 2), 3 parts (embodiment 3), in addition, obtain similarly to Example 1 curable adhensive compositions, similarly obtain the member with hardened coating film.
(embodiment 4～embodiment 6)
Being used as polyolefinic number average molecular weight is 890 polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) LV not ", three leaf science and technology (Shamrock) companies manufacture) 0.02 part of (embodiment 4), 0.1 part (embodiment 5), 0.2 part (embodiment 6) replace the hydrogenation iso-butylene that number average molecular weight is 350 (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufactures), in addition, obtain similarly to Example 1 the member with hardened coating film.
(embodiment 7～embodiment 8)
Usage quantity molecular-weight average is 400 paraffin (trade(brand)name: " Song Cunbai (Moresco-White) P-80 ", Song Cun (MORESCO) company manufactures) 0.02 part (embodiment 7), 0.3 part (embodiment 8) replace the hydrogenation iso-butylene that number average molecular weight is 350 (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufactures), in addition, obtain similarly to Example 1 curable adhensive compositions, similarly obtain the member with hardened coating film.
(embodiment 9～embodiment 10)
Usage quantity molecular-weight average is 550 paraffin (trade(brand)name: " Song Cunbai (Moresco-White) P-260 ", Song Cun (MORESCO) company manufactures) 0.02 part (embodiment 9), 0.3 part (embodiment 10) replace the hydrogenation iso-butylene that number average molecular weight is 350 (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufactures), in addition, obtain similarly to Example 1 curable adhensive compositions, similarly obtain the member with hardened coating film.
(comparative example 1)
In not using embodiment 1, paraffin used, obtain similarly to Example 1 the member with hardened coating film.
(comparative example 2)
It is 280 hydrogenation iso-butylene (trade(brand)name " Pa Limu (Parleam) 4 ": You company manufactures) that the hydrogenation iso-butylene that is 350 by number average molecular weight (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufacture) changes to number average molecular weight, in addition, obtain similarly to Example 2 the member with hardened coating film.
(comparative example 3)
It is 1200 hydrogenation iso-butylene (trade(brand)name " Pa Limu (Parleam) 18 ": You company manufactures) that the hydrogenation iso-butylene that is 350 by number average molecular weight (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufacture) changes to number average molecular weight, in addition, obtain similarly to Example 2 the member with hardened coating film.
(comparative example 4)
Usage quantity molecular-weight average is 2150 polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) EV not ", three leaf science and technology (Shamrock) companies manufacture) 0.1 part replace the polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) LV not " that in embodiment 5, number average molecular weight used is 890, three leaf science and technology (Shamrock) companies manufacture), in addition, obtain similarly to Example 5 curable adhensive compositions, similarly obtain the member with hardened coating film.
(comparative example 5)
Usage quantity molecular-weight average is 3200 polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) HV not ", three leaf science and technology (Shamrock) companies manufacture) 0.1 part replace the polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) LV not " that in embodiment 5, number average molecular weight used is 890, three leaf science and technology (Shamrock) companies manufacture), in addition, obtain similarly to Example 3 curable adhensive compositions, similarly obtain the member with hardened coating film.
(comparative example 6)
Want the polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) BASE not " that usage quantity molecular-weight average is 2500, three leaf science and technology (Shamrock) companies manufacture) 0.1 part replace the polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) LV not " that in embodiment 5, number average molecular weight used is 890, three leaf science and technology (Shamrock) companies manufacture) acquisition coating agent, but do not form uniform solution, cannot obtain the member with hardened coating film.
(comparative example 7)
Usage quantity molecular-weight average is 900, fusing point is the solid polyethylene compound (trade(brand)name: " polymer wax (Hi-wax) 100P HP10A " of 118 DEG C, Mitsui Chemicals, Inc. manufactures) 0.1 part replace the polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) LV not " that in embodiment 5, number average molecular weight used is 890, three leaf science and technology (Shamrock) companies manufacture), in addition, obtain similarly to Example 5 curable adhensive compositions, similarly obtain the member with hardened coating film.
(comparative example 8)
Except using 5 parts of hydrogenation iso-butylenes that number average molecular weight used is 350 in embodiment 1 (trade(brand)name " Pa Limu (Parleam) 6 ": You company manufactures), obtain similarly to Example 1 curable adhensive compositions, similarly obtain the member with hardened coating film.
(comparative example 9)
Except using the polyethylene (trade(brand)name: " Vaasa is Lip river (Versaflow) LV not " that in embodiment 2, number average molecular weight used is 890, three leaf science and technology (Shamrock) companies manufacture) beyond 5 parts, obtain similarly to Example 2 curable adhensive compositions, similarly obtain the member with hardened coating film.
The member with hardened coating film of embodiment 1～embodiment 10 and comparative example 1～comparative example 10 is carried out to following evaluation of physical property, will the results are summarized in table 1.
(pencil hardness)
To the hardened coating film face of the member with hardened coating film, use Ke Limensi (Klemens) formula scratch hardness test machine (pattern: HA-301, machines industry (Tester Sangyo) company manufactures) measure with load 750g according to the K5400 of Japanese Industrial Standards (Japanese Industrial Standards, JIS).
(scuff resistance)
The square pad (pad) of 1 square centimeter of Steel Wool (steel wool) that #0000 has been installed is placed on the hardened coating film face with the member of hardened coating film, come and go after 10 times with load 500g, visual assessment outward appearance, the number of mensuration scar.
(mist value, full light transmittance)
Use haze meter (Haze Meter) (pattern: NDH2000, Japanese electricity Se company manufactures) to measure mist value (Hz) and the full light transmittance (T.t.) with the member of hardened coating film.
(mensuration of kinetic friction coefficient)
For the hardened coating film face of the member with hardened coating film, at load for 200g, draw speed being that 500mm/min, minute are 60 seconds, to measure temperature be 25 degree, measuring number of times is under the condition of 5 times, measure the kinetic friction coefficient of plane pressure head and hardened coating film face, obtain the simple mean value of 5 measured values.
(sliding of finger)
Forefinger put down gently on the hardened coating film face of the member with hardened coating film and come and go friction 10 times, evaluating sliding.
Zero: the resistance to finger is few, can easily slide.
×: finger is had to resistance, be difficult to slide.
Result by table 1 shows, for use embodiment 1～embodiment 10 curable adhensive compositions with for the member of hardened coating film, the excellences such as the transparency, scuff resistance, pencil hardness, sliding and balance are good.Therefore, these members with hardened coating film can suitably need the purposes of hard painting property, the transparency and sliding for indicating meter, touch-screen, building materials etc.
With respect to this, not containing in the comparative example 1 of sliding imparting agent (A), although the hard painting property of scuff resistance, the pencil hardness etc. of hardened coating film is good, frictional coefficient is high, the sliding deficiency of finger.
Contain number average molecular weight and be in 280 the comparative example 2 of Parleam, although the hard painting property of scuff resistance, the pencil hardness etc. of hardened coating film is good, frictional coefficient is high, the sliding deficiency of finger.
Contain number average molecular weight and be in 1200 the comparative example 3 of Parleam, on the surface of the member with hardened coating film, confirm drop, cannot evaluate.
Contain respectively number average molecular weight and be 2100,2500 poly comparative example 4, comparative example 5 also identical with comparative example 3, on the surface of the member with hardened coating film, confirm drop, cannot evaluate.
Contain number average molecular weight and be in 3200 the situation of poly comparative example 6, curable adhensive compositions separates, and cannot make the member with hardened coating film.
Contain number average molecular weight and be in 900 the comparative example 7 of solid polyethylene compound, although the hard painting property of scuff resistance, the pencil hardness etc. of hardened coating film is good, mist value is high and opaque, and frictional coefficient is high, and the sliding of finger is also not enough.
The comparative example 8 that contains 5 parts of Parleams, contain in 5 parts of poly comparative examples 9, all similarly on the surface of the member with hardened coating film, confirm drop with comparative example 3, cannot evaluate.
Learn, meet (i) by the paraffin as sliding imparting agent (A) and alkene is the condition of liquid at 25 DEG C, and meet (ii) and be set as specific mass range with respect to active energy ray hardening compound (B) 100 mass parts, and then (iii) number average molecular weight is set as to all conditions of specific scope, can provide the transparency excellent and easy damaged and then have the hardened coating film of excellent finger sliding concurrently not.
［ utilizability in industry ］
Active energy ray curable adhensive compositions of the present invention can be for wanting to give all purposes of sliding.For example, can be suitably for giving sliding to blooming member.In addition, can give identical function for window glass and the various print surface separately of eyeglass, buildings or the vehicle etc. of the camera lens of the most surface portion to various plastic molded articles, photographic camera, glasses.And then, also can be for giving sliding to Wood member surface.
Claims (2)
1. an active energy ray curable adhensive compositions, with respect to active energy ray hardening compound (B) 100 mass parts, contain paraffin or polyolefine (A) with the scope more than 0.01 mass parts, below 3 mass parts, the number average molecular weight of described paraffin or polyolefine (A) is more than 320 and below 1000, and at 25 DEG C, is liquid.
2. the member with hardened coating film, it is being selected from least a portion of at least one member in glass, plastics, metal, Wood member and paper, the hardened coating film being formed is set forms by active energy ray curable adhensive compositions as claimed in claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013071124A JP5374761B1 (en) | 2013-03-29 | 2013-03-29 | Active energy ray-curable composition |
| JP2013-071124 | 2013-03-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104073036A true CN104073036A (en) | 2014-10-01 |
| CN104073036B CN104073036B (en) | 2016-01-20 |
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| CN201410114247.6A Expired - Fee Related CN104073036B (en) | 2013-03-29 | 2014-03-25 | Active energy ray curable adhensive compositions and the component with hardened coating film |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP5374761B1 (en) |
| KR (1) | KR101437093B1 (en) |
| CN (1) | CN104073036B (en) |
| TW (1) | TWI470045B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI602866B (en) * | 2013-04-09 | 2017-10-21 | Toagosei Co Ltd | Active energy ray-curable resin composition |
| JP6674736B2 (en) * | 2014-12-01 | 2020-04-01 | Ｄｉｃグラフィックス株式会社 | Active energy ray-curable composition |
| EP3865301B1 (en) | 2015-03-18 | 2024-06-12 | Riken Technos Corporation | Hard coat laminated film |
| US11433651B2 (en) | 2015-03-18 | 2022-09-06 | Riken Technos Corporation | Hard coat laminated film |
| WO2016147716A1 (en) | 2015-03-18 | 2016-09-22 | リケンテクノス株式会社 | Adhesive film |
| EP3272513B1 (en) | 2015-03-18 | 2022-06-01 | Riken Technos Corporation | Molded body |
| CN109130410B (en) | 2015-03-18 | 2021-02-05 | 理研科技株式会社 | Hard coating laminated film and method for producing the same |
| EP3272527B1 (en) | 2015-03-18 | 2022-05-11 | Riken Technos Corporation | Anti-glare hard coat laminated film |
| EP3272529B1 (en) | 2015-03-18 | 2022-05-04 | Riken Technos Corporation | Hard coat laminated film |
| TWI745316B (en) | 2015-11-25 | 2021-11-11 | 日商理研科技股份有限公司 | Door |
| US11774166B2 (en) | 2015-11-25 | 2023-10-03 | Riken Technos Corporation | Door body |
| JP6644534B2 (en) | 2015-12-08 | 2020-02-12 | リケンテクノス株式会社 | Hard coat laminated film |
| EP3808800B1 (en) | 2016-09-14 | 2022-01-05 | Riken Technos Corporation | Hard coat laminated film |
| JP7064313B2 (en) | 2016-11-25 | 2022-05-10 | リケンテクノス株式会社 | Hardcourt laminated film |
| JP6676870B1 (en) * | 2019-12-24 | 2020-04-08 | 東洋インキＳｃホールディングス株式会社 | Active energy ray-curable ink composition and printed matter |
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| CN1649734A (en) * | 2002-05-02 | 2005-08-03 | 帝人杜邦菲林日本株式会社 | Laminated film for optical use |
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| JP2013014729A (en) * | 2011-07-06 | 2013-01-24 | Daicel Corp | Transparent film, method for manufacturing the same and method of using the same |
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| JP3539678B2 (en) * | 2000-06-16 | 2004-07-07 | 株式会社日本触媒 | Method for producing spherical particles |
| JP3827617B2 (en) * | 2002-06-25 | 2006-09-27 | 積水化成品工業株式会社 | Resin particles and method for producing the same |
| JP5098355B2 (en) * | 2006-02-17 | 2012-12-12 | Ｄｉｃ株式会社 | Polymerizable liquid crystal composition |
| JP2008007595A (en) * | 2006-06-28 | 2008-01-17 | Mitsubishi Rayon Co Ltd | Curable resin composition and coating material |
| TWI659091B (en) * | 2009-02-20 | 2019-05-11 | 迪愛生股份有限公司 | Polymeric liquid crystal composition |
| JP2010229287A (en) | 2009-03-27 | 2010-10-14 | Aica Kogyo Co Ltd | Curable resin composition and film |
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2013
- 2013-03-29 JP JP2013071124A patent/JP5374761B1/en active Active
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2014
- 2014-03-13 KR KR1020140029432A patent/KR101437093B1/en active IP Right Grant
- 2014-03-25 CN CN201410114247.6A patent/CN104073036B/en not_active Expired - Fee Related
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1649734A (en) * | 2002-05-02 | 2005-08-03 | 帝人杜邦菲林日本株式会社 | Laminated film for optical use |
| CN102206439A (en) * | 2010-03-24 | 2011-10-05 | Dic株式会社 | Inorganic particle dispersoid, energy ray-curable resin composition and film |
| JP2012062364A (en) * | 2010-09-14 | 2012-03-29 | Toppan Printing Co Ltd | Hardcoat film and touch panel using the same |
| JP2013014729A (en) * | 2011-07-06 | 2013-01-24 | Daicel Corp | Transparent film, method for manufacturing the same and method of using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101437093B1 (en) | 2014-09-03 |
| CN104073036B (en) | 2016-01-20 |
| JP5374761B1 (en) | 2013-12-25 |
| TWI470045B (en) | 2015-01-21 |
| JP2014193978A (en) | 2014-10-09 |
| TW201437304A (en) | 2014-10-01 |
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Effective date of registration: 20180306 Address after: Japan Tokyo central Beijing two chome 2 No. 1 Co-patentee after: TOYOCHEM Co.,Ltd. Patentee after: TOYO INK SC HOLDINGS Co.,Ltd. Address before: Japan Tokyo central Beijing three chome 7 No. 1 Co-patentee before: TOYO INK Co.,Ltd. Patentee before: TOYO INK SC HOLDINGS Co.,Ltd. |
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