CN103360560B - Coating material - Google Patents
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- CN103360560B CN103360560B CN201310105853.7A CN201310105853A CN103360560B CN 103360560 B CN103360560 B CN 103360560B CN 201310105853 A CN201310105853 A CN 201310105853A CN 103360560 B CN103360560 B CN 103360560B
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Abstract
It is provided as organic material, can obtain the highly branched chain high-index material of appropriate refractive index.Highly branched chain high-index material of the invention, is reacted with diisocyanate cpd or aromatic dianhydride by triazine system or isocyanuric acid ester system triamine compound and obtained.
Description
Technical field
Highly branched chain high-index material on highly branched chain high-index material and organic-inorganic composition of the invention.
Background technology
In the past, in order to make resin bulk and coating material high index of refraction, known technology has, to the organic of low-refraction
The inorganic oxide particle and metal alkoxide of high index of refraction are added in material to improve refractive index.(with reference to patent document 1).
Prior art literature
Patent document
Patent document 1：Japanese Patent Laid-Open 2007-270099 publications
The content of the invention
But, in order to improve the refractive index of organic material, it is necessary to a large amount of addition inorganic oxide particles etc..This kind of inorganic oxygen
Compound particulate price general charged is very high, is the reason for causing fee of material to increase.
In view of the problem points of above-mentioned conventional art, technical task of the invention is provided as organic material, available
The highly branched chain high-index material of appropriate refractive index.Additionally, technical task is to provide by by this kind of high index of refraction of can obtain
Highly branched chain high-index material mixes with inorganic oxide particle, is preferably chemically bonded, and is suppressing adding for inorganic oxide particle
The highly branched chain high-index material of the organic-inorganic composition of appropriate refractive index can be obtained while dosage.
The present inventors have found after being studied repeatedly to solve above-mentioned problem, triazine system or the amine compounds of isocyanuric acid ester system three
The highly branched chain high-index material that thing and diisocyanate cpd or aromatic dianhydride reaction are obtained, it is organic relative to conventional
Material, can obtain refractive index (refractive index more than 1.6) higher.
The triazine system triamine compound used in highly branched chain high-index material of the invention herein, is following formula (1) table
The compound for showing.
【Change 5】
【Change 6】
In formula (1), R1, R2, R3 are the group that formula (2) or formula (3) are represented, in formula (2), formula (3), R4 and R5 represent divalent
Organic group.In addition, the organic group of divalent is referred to being generated by two hydrogen atoms except dealkylation, free valency is not joined
With the divalent group for forming double bond, i.e. alkylene (hydrocarbylene), the alkylene of such as carbon number 1~10 can be enumerated
Base, phenylene etc..Herein, the alkylidene of carbon number 1~10 can arbitrarily be chain, branched, ring-type.As this kind of triazine system
The specific example of triamine compound, can enumerate, 1,3,5- tri- (4- amino-benzene oxygens) triazines that following formula (6) is represented and with
Under formula (7) represent 1,3,5- tri- [(3- aminophenyls) amino] triazine.
【Change 7】
【Change 8】
Additionally, the isocyanuric acid ester system triamine compound used in highly branched chain high-index material of the invention is following formula
(4) compound for representing.
【Change 9】
【Change 10】
Formula（4）In, R6~R8 is formula（5）The group of expression, formula（5）In, R9 represents the organic group of divalent.
As the specific example of this kind of isocyanuric acid ester system triamine compound, can enumerate, formula below（8）1 for representing,
3,5- tri- (4- amino-benzene oxygens) -1,3,5- triazines -2,4,6 (1H, 3H, 5H)-triketone.
【Change 11】
Additionally, as the diisocyanate cpd used in highly branched chain high-index material of the invention, example can be enumerated
Such as, diphenyl methane 4,4'- diisocyanate（MDI）, PPDI, m-benzene diisocyanate, paraxylene two it is different
Cyanate, m xylene diisocyanate, 2,4 toluene diisocyanate, 2,6- toluene di-isocyanate(TDI)s, 4,4'- diphenylmethyls
The aromatic diisocyanate such as alkane isocyanates, naphthalene diisocyanate class, IPDI, the isocyanide of hexa-methylene two
Acid esters, 4,4'- dicyclohexyl methyl hydride diisocyanates, hydrogenated xylene diisocyanate, norbornene alkyl diisocyanate, bad ammonia
The diisocyanates of the aliphatic such as sour diisocyanate or alicyclic structure, more than one biuret body of isocyanate-monomer
Or the PIC such as the isocyanates body of above-mentioned isocyanate compound trimerizing etc..
Additionally, as the aromatic dianhydride used in highly branched chain high-index material of the invention, can enumerate for example, 4,
4'-（Hexafluoroisopropylidenyl）Two anhydride phthalic acids（6FAD）, pyromellitic acid anhydride（PMDA）, the double phthalic anhydrides of oxygen（ODPA）、
3,3', 4,4'- benzophenone tetracarboxylic dianhydride（BTDA）, 3,3', 4,4'- diphenyl tetracarboxylic acid dianhydrides（DSDA）, 2,2'- it is double
[(di carboxyl phenyloxy) phenyl] propane dianhydride（BSAA）Deng compound.
This kind of triazine system or isocyanuric acid ester system triamine compound and diisocyanate cpd or aromatic dianhydride it is anti-
Should, reaction temperature is 0~200 DEG C, preferably room temperature~100 DEG C, and the reaction time is 30 minutes~5 hours, preferably 1~3 hour.
Additionally, triazine system or isocyanuric acid ester system triamine compound（Monomer）With diisocyanate cpd（Monomer）Or virtue
Fragrant race's dianhydride（Monomer）Reaction mol ratio be 1.0：0.3 to 1.0：1.2, preferably 1.0：0.4 to 1.0：Can appoint in the range of 1.1
Meaning change.In addition, monomer order of addition is not particularly limited, it is desirable that when synthesis diisocyanate cpd or fragrance
During race's dianhydride monomer end multibranched polymer, to addition triazine system in the monomer of diisocyanate cpd or aromatic dianhydride
Or the monomer of isocyanuric acid ester system triamine compound, when synthesis triazine system or isocyanuric acid ester system triamine compound monomer end are more
During branch polymer, to addition diisocyanate cpd or virtue in the monomer of triazine system or isocyanuric acid ester system triamine compound
The monomer of fragrant race's dianhydride.
In addition, when manufacturing highly branched chain high-index material of the present invention, preferably being carried out in the solvent of regulation.As
This kind of solvent, can enumerate for example, MEK, methyl iso-butyl ketone (MIBK), cyclohexanone, benzene,toluene,xylene, methyl cellosolve, ethyl
Cellosolve, n-propyl cellosolve, methyl alcohol, ethanol, isopropanol, n-butanol, isobutanol, methyl iso-butyl ketone (MIBK), propylene glycol monomethyl ether,
Ethyl acetate, propyl acetate, propylene glycol monomethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, DMA etc.,
They can also be used in mixed way.
Make triazine system or isocyanuric acid ester system triamine compound be reacted with diisocyanate cpd or aromatic dianhydride,
During to highly branched chain high-index material of the invention, can be to make triazine system or isocyanuric acid ester system triamine compound be dissolved in above-mentioned
While solvent, diisocyanate cpd or aromatic dianhydride is made to be dissolved in above-mentioned solvent, both mix for order, in regulation temperature
After the lower reaction of degree, solvent is removed.
In addition, can be obtained by mixing with inorganic oxide particle by making highly branched chain high-index material of the invention
The highly branched chain high-index material of machine-inorganic composite, preferably by making highly branched chain high-index material and inorganic oxide micro-
Grain reaction, the highly branched chain high-index material of mixed type organic-inorganic composition is obtained by covalent bond.It is this kind of it is organic-
The highly branched chain high-index material of inorganic composite, compared to conventional, inorganic oxide particle necessary to refractive index adjustment
Addition reduce, while can obtain necessary refractive index.In addition, can be used for this kind of organic-inorganic composition of the invention
The inorganic oxide particle of highly branched chain high-index material, can be suitably submicron order using average grain diameter.It is preferred that 100nm with
Under, as long as with physical size, then its lower limit is not particularly limited.According to the particle diameter of retrievable inorganic oxide particle
Depending on.As usable inorganic oxide particle, can enumerate, be high index of refraction, can surface modification metal oxide
Colloidal sol.Can enumerate for example, aluminum oxide（Al2O3）, zirconium oxide（ZrO2）, titanium oxide（TiO2）、ITO（Tin-doped indium oxide）, oxidation
Tin（SnO2）, zinc oxide（ZnO）, antimony oxide（Sb2O3、Sb2O5Deng）And their composite particles etc..In addition, this kind of metal oxidation
The surface of thing particulate has hydroxyl.Additionally, as inorganic constituents, in addition to adding inorganic particles, also can be by sol-gel
Method imports inorganic constituents.In addition, can arbitrarily be that macromolecular chain end or surface of inorganic particles are modified by coupling agent.As
Coupling agent, can enumerate, the silane idol such as γ-glycidoxypropyltrimewasxysilane or γ-chloropropyl front three oxosilane
Connection agent, four（2,2- diene propoxy methyl -1- butyl）It is double（Double tridecyl）Phosphito titanate, two（Dioctylphyrophosphoric acid
Ester group）The titanate coupling agents such as ethylene titanate esters；The aluminium system coupling agents such as acetyl alkoxy aluminum-diisopropoxide；Acetylacetone,2,4-pentanedione zirconium network
The zirconium system coupling agents such as compound, methacrylic acid 2- isocyanatoethyls, acrylic acid 2- isocyanatoethyls, 1,1-（Double third
Alkene pivaloyloxymethyl）Ethyl isocyanate etc..The reaction ratio of modification, reaction condition are that temperature is 0 DEG C~200 DEG C, preferably 10 DEG C
~100 DEG C.Reaction ratio is that, in macromolecular chain end, it is 1.0 that macromolecular chain compares with the reaction of modification coupling agent：0.3~1.0：
1.2, preferably 1.0：0.4~1.0：1.1.Surface of inorganic particles it is modified, degree of modification is 1~100mol%, preferably 5~70mol%,
Reaction temperature is 0 DEG C~100 DEG C, preferably room temperature~50 DEG C, and the reaction time can arbitrarily change in the range of 1 minute~24 hours.
The amount of inorganic constituents can arbitrarily change in 1~90wt% in preferably 5~70%.
So obtained highly branched chain high-index material, can be used as resin bulk and coating material etc., can obtain more than 1.6
High index of refraction.By highly branched chain high-index material of the invention or the highly branched chain high-index material of organic-inorganic composition
Be made as solution using solvent, by by the solution optical component surfaces using spin coating, spraying, dip-coating, scrape rod coating, flow coat,
Cap is applied（キャップコート）, scraper for coating, die coating, roller coat, gravure coating process etc. and be only coated with solid after the thickness of regulation
Change, refractive index coating high can be formed on optical component.Additionally, by using Jet forming machine and extrusion shaping machine etc., this
It is good that the highly branched chain high-index material of invention or the highly branched chain high-index material of organic-inorganic composition can be obtained mechanical properties
Good membranaceous, sheet resin formed product.Particularly this kind of resin forming article is suitable for optical applications.
Highly branched chain high-index material of the invention, is considering to use the underload of environment as plant material
While the PLA of material, the mechanical properties such as marresistance and case hardness can be lifted.
Specific embodiment
The related embodiment of the present invention exemplified below is illustrated, but the present invention is not limited to this.
（Embodiment 1）
By triazine system triamine compound TAPOTZ (1,3,5-tris (4-aminophenoxy) triazine, 1,3,5- tri-
(4- amino-benzene oxygens) triazine)（Wakayama Seika Kogyo Co., Ltd.'s article made to order）4.0mmol is taken with there-necked flask, is dissolved in
DMAc (N, N-dimethylacetamide, DMA) 10ml.By the solution while stirring, slow on one side to drip
Under be dissolved in the MDI of DMAc15ml (methylenediphenyl4,4'-diisocyanate, diphenyl methane 4,4'- bis- be different
Cyanate)（Tokyo HuaCheng Industry Co., Ltd D0897）4.0mmol, stirs its reaction of 3 small seasons in 80 DEG C of oil bath.Stir
After mixing, by mixed solution instillation methyl alcohol, purified polymer reclaims the solid of white by suction filtration.It is made in true at 85 DEG C
Sky dries a Dinner, obtains target highly branched chain high-index material（The poly- urea of highly branched chain）Resin combination.The resin that will be obtained
Composition determines refractive index by the apparatus for measuring reflectance USPM-RUIII that Olympus is manufactured.Measurement result is as shown in table 1.
（Embodiment 2）
The highly branched chain high-index material that embodiment 1 is obtained is dissolved in DMAc again, is modified to solution addition GTMS
Colloidal zirconia（Surface modification rate 25mol%）（Nissan Chemical Ind Ltd）, make it relative to highly branched chain high index of refraction material
Expect to be 10wt%, stir 15 minutes at room temperature.The solution-cast that will be obtained（cast）In PET（Polyethylene terephthalate）
On piece, dried 3 hours by 85 DEG C, the highly branched chain high index of refraction material of target organic-inorganic composition is obtained on PET sheet
Material.The refractive index of the highly branched chain high-index material for obtaining is determined similarly to Example 1.Measurement result is as shown in table 1.
（Embodiment 3）
Except addition GTMS modification colloidal zirconias（Surface modification rate 25mol%）, make what it was obtained relative to embodiment 1
Highly branched chain high-index material be 30wt% beyond, carry out operation similarly to Example 2, obtained on PET sheet target it is organic-
The highly branched chain high-index material of inorganic composite.The highly branched chain high-index material that obtains is determined similarly to Example 1
Refractive index.Measurement result is as shown in table 1.
（Embodiment 4）
Except addition GTMS modification colloidal zirconias（Surface modification rate 50mol%）, make what it was obtained relative to embodiment 1
Highly branched chain high-index material be 10wt% beyond, carry out operation similarly to Example 2, obtained on PET sheet target it is organic-
The highly branched chain high-index material of inorganic composite.The highly branched chain high-index material that obtains is determined similarly to Example 1
Refractive index.Measurement result is as shown in table 1.
（Embodiment 5）
Except addition GTMS modification colloidal zirconias（Surface modification rate 50mol%）, make what it was obtained relative to embodiment 1
Highly branched chain high-index material be 30wt% beyond, carry out operation similarly to Example 2, obtained on PET sheet target it is organic-
The highly branched chain high-index material of inorganic composite.The highly branched chain high-index material that obtains is determined similarly to Example 1
Refractive index.Measurement result is as shown in table 1.
（Embodiment 6）
Except addition GTMS modification colloidal zirconias（Surface modification rate 50mol%）, make what it was obtained relative to embodiment 1
Highly branched chain high-index material be 50wt% beyond, carry out operation similarly to Example 2, obtained on PET sheet target it is organic-
The highly branched chain high-index material of inorganic composite.The highly branched chain high-index material that obtains is determined similarly to Example 1
Refractive index.Measurement result is as shown in table 1.
（Embodiment 7）
Except addition GTMS modification colloidal titanias（Day waves catalyst chemical conversion industry surface modification type commercially available product）, make its relative
Beyond the highly branched chain high-index material that embodiment 1 is obtained is 30wt%, operation similarly to Example 2 is carried out, in PET sheet
On obtain the highly branched chain high-index material of target organic-inorganic composition.The highly branched chain for obtaining is determined similarly to Example 1
The refractive index of high-index material.Measurement result is as shown in table 1.
（Embodiment 8）
Except addition GTMS modification colloidal titanias（Day waves catalyst chemical conversion industry surface modification type commercially available product）, make its relative
Beyond the highly branched chain high-index material that embodiment 1 is obtained is 50wt%, operation similarly to Example 2 is carried out, in PET sheet
On obtain the highly branched chain high-index material of target organic-inorganic composition.The highly branched chain for obtaining is determined similarly to Example 1
The refractive index of high-index material.Measurement result is as shown in table 1.
（Embodiment 9）
By pyromellitic acid anhydride（PMDA）（Tokyo HuaCheng Industry Co., Ltd：B0040）Taken with there-necked flask
3.0mmol, is dissolved in DMAc.By the solution while stirring, slowly drips be dissolved in DMAc's in advance on one side
TAPOTZ1.6mmol, then stir about 3 hours at room temperature.After stirring, by the mixed solution instill methyl alcohol in, purified polymer,
The solid of white is reclaimed by suction filtration.Make it in a Dinner is vacuum dried at 85 DEG C, obtain the resin of highly branched chain high-index material
Composition.The apparatus for measuring reflectance USPM- that the resin combination that will be obtained is manufactured by Olympus similarly to Example 1
RUIII determines refractive index.Measurement result is as shown in table 1.
（Embodiment 10）
By the double phthalic anhydrides of oxygen（ODPA）（Tokyo HuaCheng Industry Co., Ltd：O0237）Taken with there-necked flask
3.0mmol, is dissolved in DMAc.By the solution while stirring, slowly drips be dissolved in DMAc's in advance on one side
TAPOTZ1.6mmol, then stir about 3 hours at room temperature.After stirring, by the mixed solution instill methyl alcohol in, purified polymer,
The solid of white is reclaimed by suction filtration.Make it in a Dinner is vacuum dried at 85 DEG C, obtain the resin of highly branched chain high-index material
Composition.The highly branched chain high-index material that will be obtained is dissolved in DMAc again, and colloidal titania is added to the solution（Day waves tactile
Matchmaker's chemical conversion industry commercially available product）, make it be 10wt% relative to highly branched chain high-index material, stir 15 minutes at room temperature.To obtain
Solution-cast in PET（Polyethylene terephthalate）On piece, dried 3 hours by 85 DEG C, had on PET sheet
The highly branched chain high-index material of machine-inorganic composite.Then, polyamic acid-titanium oxide hybrid films are peeled from PET sheet, Gu
Heating under 1 hour, blanket of nitrogen after metal framework, are respectively carried out at 100 DEG C, 200 DEG C, 300 DEG C, obtains highly branched chain
The film of polyimides-titanium oxide mixing.The highly branched chain of the composite organic-inorganic material for obtaining is determined similarly to Example 1
The refractive index of high-index material.Measurement result is as shown in table 1
（Embodiment 11）
Except addition GTMS modification colloidal titanias（Day waves catalyst chemical conversion industry surface modification type commercially available product）, make its relative
Beyond the highly branched chain high-index material that embodiment 10 is obtained is 30wt%, operation similarly to Example 10 is carried out, obtain mesh
Mark the highly branched chain high-index material of organic-inorganic composition.The highly branched chain high index of refraction for obtaining is determined similarly to Example 1
The refractive index of material.Measurement result is as shown in table 1.
（Embodiment 12）
By isocyanuric acid ester system triamine compound TAATZ（1,3,5- tri- (4- amino-benzene oxygens) -1,3,5- triazines -2,4,6
(1H, 3H, 5H)-triketone）（Wakayama Seika Kogyo Co., Ltd.'s article made to order）4.0mmol is taken with there-necked flask, DMAc is dissolved in
(N, N-dimethylacetamide, DMA) 10ml.By the solution while stirring, slowly drips molten on one side
Solution is in MDI (methylenediphenyl4,4'-diisocyanate, diphenyl methane 4, the isocyanic acids of 4'- bis- of DMAc15ml
Ester)（Tokyo HuaCheng Industry Co., Ltd D0897）4.0mmol, stirs its reaction of 3 small seasons in 80 DEG C of oil bath.After stirring,
By in mixed solution instillation methyl alcohol, purified polymer reclaims the solid of white by suction filtration.It is made in vacuum drying at 85 DEG C
One Dinner, obtains target highly branched chain high-index material（The poly- urea of highly branched chain）Resin combination.The resin combination that will be obtained
The apparatus for measuring reflectance USPM-RUIII manufactured by Olympus determines refractive index.Measurement result is as shown in table 1.
【Table 1】
The refractive index of the highly branched chain high-index material that embodiment 1~12 is obtained has exceeded 1.65, and display is had
There is the material of high index of refraction.
Claims (3)
1. a kind of coating material, is the coating material for forming coating on optical component, it is characterised in that include：
The isocyanuric acid ester system triamine compound and two that the triazine system triamine compound or following formula (4) represented by following formula (1) are represented
Isocyanate compound or aromatic dianhydride reaction obtain the highly branched chain high-index material with more than 1.6 refractive index,
With
Coupling agent and
Surface has the metal oxide microparticle of hydroxyl
The highly branched chain high-index material of the organic-inorganic composition being made up of covalent bond integration；
【Change 1】
【Change 2】
Wherein, in formula (1), R1, R2, R3 are the groups that formula (2) or formula (3) are represented, in formula (2), formula (3), R4 and R5 represent divalent
Organic group；
【Change 3】
【Change 4】
Wherein, in formula (4), R6~R8 is the group that formula (5) is represented, in formula (5), R9 represents the organic group of divalent.
2. coating material according to claim 1, it is characterised in that the diisocyanate cpd is that aromatic series two is different
The diisocyanates of cyanate, aliphatic diisocyanate or alicyclic structure.
3. the coating material according to claim 1 or claim 2, it is characterised in that the aromatic dianhydride be selected from
The anhydride phthalic acids of 4,4'- (hexafluoroisopropylidenyl) two, pyromellitic acid anhydride, oxygen double phthalic anhydride, 3,3', 4,4'- hexichol first
Ketone tetracarboxylic acid dianhydride, 3,3', double [(di carboxyl phenyloxy) phenyl] propane dianhydrides of 4,4'- diphenyl tetracarboxylic acid dianhydride, 2,2'-
Compound.
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| JP2012-079934 | 2012-03-30 | ||
| JP2012079934A JP6010316B2 (en) | 2012-03-30 | 2012-03-30 | Coating material |
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| CN103360560A CN103360560A (en) | 2013-10-23 |
| CN103360560B true CN103360560B (en) | 2017-06-09 |
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| CN (1) | CN103360560B (en) |
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| KR102490028B1 (en) | 2017-02-24 | 2023-01-18 | 삼성전자주식회사 | Organic-inorganic hybrid composition, and article and optical component including the same |
| CN110078888B (en) * | 2019-04-04 | 2020-07-28 | 华南理工大学 | Porous organic polymer connected by thiourea structure and preparation method and application thereof |
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| JPS6021647B2 (en) * | 1979-03-02 | 1985-05-29 | アレクセイ・ヤコフレウイツチ・チエルニホフ | heat resistant composition |
| JPS5941320A (en) * | 1982-09-01 | 1984-03-07 | Nisshinbo Ind Inc | Heat-resistant thermosetting resin |
| JPS62116635A (en) * | 1985-11-15 | 1987-05-28 | Nisshinbo Ind Inc | Production of fire-proof board |
| JPH10319204A (en) * | 1997-05-20 | 1998-12-04 | Nippon Polyurethane Ind Co Ltd | Production of plastic lens |
| JP3906013B2 (en) * | 2000-07-06 | 2007-04-18 | 大日本印刷株式会社 | Gas barrier laminate and method for producing the same |
| EP1172425A1 (en) * | 2000-07-11 | 2002-01-16 | Dsm N.V. | Outdoor durable coating composition |
| WO2006025327A1 (en) * | 2004-08-30 | 2006-03-09 | National University Corporation Nagoya Institute Of Technology | Multibranched polyimide hybrid material |
| JP2006131706A (en) * | 2004-11-04 | 2006-05-25 | Nagoya Institute Of Technology | Low-dielectric polyimide material and high-efficiency separation membrane |
| JP2008231170A (en) * | 2007-03-19 | 2008-10-02 | Nagoya Industrial Science Research Inst | Photosensitive multi-branched polyimide hybrid precursor |
| JP4866774B2 (en) * | 2007-03-30 | 2012-02-01 | 富士フイルム株式会社 | Planographic printing plate precursor and lithographic printing plate preparation method |
| JP2012082248A (en) * | 2010-10-07 | 2012-04-26 | Autonetworks Technologies Ltd | Moisture-curing liquid composition, and cured material using the same |
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| JP6010316B2 (en) | 2016-10-19 |
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| JP2013209490A (en) | 2013-10-10 |
| TWI582148B (en) | 2017-05-11 |
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