CN110407481A - A kind of preparation method of multi-functional photochromic film - Google Patents

A kind of preparation method of multi-functional photochromic film Download PDF

Info

Publication number
CN110407481A
CN110407481A CN201910720335.3A CN201910720335A CN110407481A CN 110407481 A CN110407481 A CN 110407481A CN 201910720335 A CN201910720335 A CN 201910720335A CN 110407481 A CN110407481 A CN 110407481A
Authority
CN
China
Prior art keywords
film
light
base
functional
thickness
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.)
Pending
Application number
CN201910720335.3A
Other languages
Chinese (zh)
Inventor
蓝碧健
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Taicang Biqi New Material Research Development Co Ltd
Original Assignee
Taicang Biqi New Material Research Development Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Taicang Biqi New Material Research Development Co Ltd filed Critical Taicang Biqi New Material Research Development Co Ltd
Priority to CN201910720335.3A priority Critical patent/CN110407481A/en
Publication of CN110407481A publication Critical patent/CN110407481A/en
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/34Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
    • C03C17/3405Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions with at least two coatings of organic materials
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02Organic tenebrescent materials
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2217/00Coatings on glass
    • C03C2217/70Properties of coatings
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2218/00Methods for coating glass
    • C03C2218/10Deposition methods
    • C03C2218/15Deposition methods from the vapour phase
    • C03C2218/151Deposition methods from the vapour phase by vacuum evaporation
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1007Non-condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1011Condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1044Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1074Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1088Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

The invention belongs to optical technical field, specially a kind of preparation method of multi-functional photochromic film.Method proposed by the present invention is successively vacuum evaporation 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene, 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, (R)-[{ [1- (6- amino -9H- purine -9- base) propyl -1- base] oxygroup } methyl] phosphoric acid, N- (the chloro- 2- tolyl of 5-) adamantane amide on a glass, obtain multi-functional photochromic film, the light transmittance of the film is 88 ~ 92%, and mist degree is 90 ~ 94%;The ultraviolet light that the ultraviolet light and wavelength for being 365nm with white light, wavelength are 254nm irradiates multi-functional photochromic film 60 seconds respectively, and the color of illumination rear film is respectively red, yellow and blue.

Description

A kind of preparation method of multi-functional photochromic film
Technical field
The invention belongs to optical technical field, specially a kind of preparation method of multi-functional photochromic film.
Background technique
It is photochromic to refer to that certain compounds molecular structure under the light action of certain wavelength and intensity become Change, so as to cause its corresponding change of absorption peak, that is, color to light, and this change is generally reversible.Organic system It is photochromic to also tend to occur simultaneously along with many processes related with photochemical reaction, so as to cause certain of molecular structure Change, reactive mode specifically includes that valence link isomery, cis-trans isomerism, key fracture, polymerization, oxidationreduction, pericyclic reaction Deng.The important functional material in the fields such as organic light-scattering material has become illumination, optics is shown, Lighting Design, can both solve liquid The intrinsic visual angle asymmetry problem of crystal display, moreover it is possible to make illumination reach high effect with display system and mutually unite with visual uniformity One purpose, the illumination combined for efficient, low damage, high uniformity with perfect vision and display equipment provide guarantee.
Currently, photochromic material and light-scattering film material are more common, but have the film material of both the above characteristic concurrently Expect very rare.
Guo Haomo etc. is prepared for rhodamine beta-hydroxy naphthaldehyde hydrazone using rhodamine B hydrazides and 2- hydroxyl-1-naphthalene Formaldehyde as raw material (L), structure passes through1HNMR,13CNMR and mass spectral characteristi.Compound L and Zn2+Form the L- Zn that coordination ratio is 1: 12+Complex compound. Target compound L and Zn are had studied using ultraviolet spectra2+Photochromic characteristic in ethanol solution.The result shows that L- Zn2+ Complex compound 500nm or more is in substantially faint yellow without absorption, but under UV-365nm irradiation, complex compound can be fast in ethanol solution Speed is changed into red, and strong absorption is generated at 557nm, and after stopping irradiation, solution can be changed into faint yellow again, and has Good fatigue resistance (Leshan Teachers College's journal, the 4th phase 34-38 in 2019).
2,3- dihydroxy -5- nitrobenzaldehyde is being made using 2- hydroxy 3-methoxybenzene formaldehyde as raw material in Bao Lihong etc. On the basis of, it is reacted with 2,3,3- trimethyl-N-hydroxyethyl -3H indoles bromide, has synthesized double hydroxyl spiropyran compounds. Have studied the photochromic properties of obtained compound.As a result, it has been found that double hydroxyl spiro-pyrans ethanol solutions of 0.02g/L, maximum is inhaled Wavelength is received in 559nm, is extended with the ultraviolet lighting time, the absorbance of solution gradually increases, and light application time is more than variation after 480s It is unobvious;After removing ultraviolet lamp, under daylight light irradiation, double hydroxyl spiro-pyrans ethanol solution colors are gradually recovered, more than 600s Solution colour almost becomes primary colors again afterwards;Under condition of different pH, double hydroxyl spiro-pyrans ethanol solutions after 365nm ultraviolet light, Show different colors (New Chemical Materials, the 5th phase 137-139 in 2018,143).
Fu Liuwa etc. chooses lauryl sodium sulfate (SDS), and octyl phenyl polyoxyethylene ether (OP-10) is composite emulsifying Agent, potassium peroxydisulfate (KPS) is initiator, by 2-(perfluoro hexyl) ethylmethyl acrylate (PFM) and acrylic ester monomer Emulsion copolymerization is carried out using pre-emulsification-semi-continuous seed emulsion polymerization method, then hydroxyl spiro-pyrans (SPOH) and lotion are subjected to object Reason is blended, and photochromic fluorinated acrylate emulsion is made.By a variety of characterization methods research n-butyl acrylate (n-BA) and The mass ratio of methyl methacrylate (MMA) soft or hard monomer, influence of the dosage of SPOH to polymerization reaction and latex film properties.Knot Fruit shows that the contact angle of latex film and water, oil improves after fluorochemical monomer is added, and thermal stability improves;The quality point of SPOH is added When number is 1. 25%, latex film has preferable photochromic properties (applied chemistry, the 12nd phase 1434-1441 in 2018).
The polysiloxanes microballoon that partial size is 2-9 μm is dispersed in acrylic resin by Lu Xin etc. as light scattering agent, It is coated on polyethylene terephthalate (PET) film surface with a thickness of 180 μm, light-scattering film is made in solvent flashing. The thickness of the concentration of polysiloxanes microballoon, partial size and coating has been investigated to optical properties such as the light transmittance of light-scattering film and mist degrees Influence.The result shows that: it is thin that light scattering can be significantly increased in the case where keeping higher light transmittance in polysiloxanes microballoon The mist degree of film.When the addition mass percent for the polysiloxanes microballoon that partial size is 5 μm is 25%, coating layer thickness is 90 μm, light dissipates The light transmittance for penetrating film is 88%, and mist degree 90%, effective light scattering coefficient has optimal light scattering property East China up to 79% Polytechnics's journal: natural science edition, the 5th phase 699-703 in 2008).
In conclusion organic material can be used for constructing the optical thin film of multiple functions, including photochromic, light-scattering film Deng.The film of simple function has been studied relatively comprehensively, but multi-functional compound thin film development is still in the stage of fumbling, needs Constantly accumulation knowledge and experience.The common recognition of those skilled in the art is the multistable discoloration of multi-functional photochromic film, And light scattering property, it is not only related to the composition of film, the structure of film is additionally depended on, needs to cooperate with the group of optimization film Point and structure, to obtain multi-functional organic optical film.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of multi-functional photochromic film.
The preparation method of multi-functional photochromic film proposed by the present invention, the specific steps are as follows:
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene, the 25 ~ 40nm that 25 ~ 40nm thickness is successively deposited on plate are thick 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 25 ~ 40nm thickness (R)-[{ [(6- amino -9H- is fast by 1- Purine -9- base) propyl -1- base] oxygroup methyl] phosphoric acid, 25 ~ 40nm thickness N- (the chloro- 2- tolyl of 5-) adamantane amide, much Function photochromic film.
Reference literature (polymer material science and engineering, the 2nd phase 54-57 in 2010), with light transmittance/mist degree analyzer, The light transmittance for measuring multi-functional photochromic film is 88 ~ 92%, and mist degree is 90 ~ 94%.
The ultraviolet light that the ultraviolet light and wavelength for being 365nm with white light, wavelength are 254nm irradiates above-mentioned multifunctional light respectively Cause optically variable films 60 seconds, the color of the multi-functional photochromic film after being shone with colour photometer detection light be respectively red, yellow and Blue.
The organic layer of multi-functional photochromic film prepared by the present invention be by four kinds of layer-by-layer vacuum depositions of organic material and At if only using a kind of organic material prepares organic layer, the present invention provides following 4 technical solutions as a comparison:
(1) 5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 25nm thickness is deposited in glass plate, obtains organic film;With Light transmittance/mist degree analyzer, the light transmittance for measuring organic film is 91%, mist degree 6%.It is the ultraviolet of 365nm with white light, wavelength The ultraviolet light that light and wavelength are 254nm irradiates above-mentioned organic film 60 seconds respectively, organic thin after being shone with colour photometer detection light The color of film is respectively red, red and red.
It can be seen that the mist degree of 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene film is lower, Light scattering property is poor, does not also have multistable photochromic effect.
(2) 5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides of 40nm thickness is deposited on a glass, obtains organic film;With saturating Light rate/mist degree analyzer, the light transmittance for measuring organic film is 89%, mist degree 7%.The ultraviolet light for being 365nm with white light, wavelength And the ultraviolet light that wavelength is 254nm irradiates above-mentioned organic film 60 seconds respectively, the organic film after being shone with colour photometer detection light Color be respectively khaki, khaki and khaki.
It can be seen that the mist degree of 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides film is lower, light scattering Performance is poor, does not also have multistable photochromic effect.
(3) 5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, (R)-[{ [1- (6- amino -9H- purine -9- base) propyl -1- base] oxygroup } methyl] phosphoric acid of 30nm thickness is deposited on a glass, Obtain organic film;With light transmittance/mist degree analyzer, the light transmittance for measuring organic film is 95%, mist degree 4%.With white light, wavelength The ultraviolet light that ultraviolet light and wavelength for 365nm are 254nm irradiates above-mentioned organic film 60 seconds respectively, with colour photometer detection light The color of organic film according to after is respectively ecru, ecru and ecru.
It can be seen that (R)-[{ [1- (6- amino -9H- purine -9- base) propyl -1- base] oxygroup } methyl] phosphoric acid membranes Mist degree is lower, and light scattering property is poor, does not also have multistable photochromic effect.
(4) 5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, N- (the chloro- 2- tolyl of 5-) adamantane amide of 35nm thickness is deposited on a glass, obtains organic film;It is surveyed with light transmittance/mist degree Determine instrument, the light transmittance for measuring organic film is 93%, mist degree 5%.The ultraviolet light and wavelength for being 365nm with white light, wavelength be The ultraviolet light of 254nm irradiates above-mentioned organic film 60 seconds respectively, and the color of the organic film after being shone with colour photometer detection light is distinguished It is pink, pink and pink.
It can be seen that the mist degree of N- (the chloro- 2- tolyl of 5-) adamantane amide film is lower, light scattering property is poor, also not With multistable photochromic effect.
Four kinds of organic matters it can be seen from correlation technique scheme (1) ~ (4): 8- amino -4- oxo -2- (1H-TETRAZOLE -5- Base) -4H-1- chromene, 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, (R)-[{ [1- (6- amino - 9H- purine -9- base) propyl -1- base] oxygroup } methyl] phosphoric acid, N- (the chloro- 2- tolyl of 5-) adamantane amide, it cannot be independent As light-scattering film material or multistable photochromic material.
If four kinds of organic matters in the organic layer of the multi-functional photochromic film in the present invention lack one kind, the present invention Also provide following 4 technical solutions as a comparison:
(5) lack 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene in organic layer
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides of 25nm thickness, (R)-[{ [1- of 40nm thickness are successively deposited on plate (6- amino -9H- purine -9- base) propyl -1- base] oxygroup methyl] phosphoric acid, 40nm thickness N- (the chloro- 2- tolyl of 5-) adamantane Amide obtains compound organic film.
With light transmittance/mist degree analyzer, the light transmittance for measuring compound organic film is 91%, mist degree 23%.With white light, wave The ultraviolet light and wavelength of a length of 365nm is that the ultraviolet light of 254nm irradiates above-mentioned multi-functional photochromic film 60 seconds respectively, is used The color of compound organic film after colour photometer detection light photograph is respectively grass green, grass green and grass green.
It can be seen that the mist degree of compound organic film is promoted than single layer organic film, but can not show a candle to multi-functional photic Optically variable films, moreover, compound organic film do not have multistable photochromic effect.
(6) lack 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides in organic layer
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 30nm thickness, (R)-of 30nm thickness are successively deposited on plate The N- (the chloro- 2- tolyl of 5-) of [{ [1- (6- amino -9H- purine -9- base) propyl -1- base] oxygroup } methyl] phosphoric acid, 40nm thickness Adamantane amide obtains compound organic film.
With light transmittance/mist degree analyzer, the light transmittance for measuring compound organic film is 90%, mist degree 21%.With white light, wave The ultraviolet light and wavelength of a length of 365nm is that the ultraviolet light of 254nm irradiates above-mentioned multi-functional photochromic film 60 seconds respectively, is used The color of compound organic film after colour photometer detection light photograph is respectively light blue, light blue and light blue.
It can be seen that the mist degree of compound organic film is promoted than single layer organic film, but can not show a candle to multi-functional photic Optically variable films, moreover, compound organic film do not have multistable photochromic effect.
(7) lack (R)-[{ [1- (6- amino -9H- purine -9- base) propyl -1- base] oxygroup } methyl] phosphoric acid in organic layer
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 25nm thickness, the 2- of 40nm thickness are successively deposited on plate N- (the chloro- 2- tolyl of 5-) adamantane amide of (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 40nm thickness, obtains Compound organic film.
With light transmittance/mist degree analyzer, the light transmittance for measuring compound organic film is 88%, mist degree 26%.With white light, wave The ultraviolet light and wavelength of a length of 365nm is that the ultraviolet light of 254nm irradiates above-mentioned multi-functional photochromic film 60 seconds respectively, is used The color of compound organic film after colour photometer detection light photograph is respectively orange, orange and orange.
It can be seen that the mist degree of compound organic film is promoted than single layer organic film, but can not show a candle to multi-functional photic Optically variable films, moreover, compound organic film do not have multistable photochromic effect.
(8) lack N- (the chloro- 2- tolyl of 5-) adamantane amide in organic layer
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 35nm thickness, the 2- of 25nm thickness are successively deposited on plate (R)-[{ [1- (6- amino -9H- purine -9- base) of (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 40nm thickness Propyl -1- base] oxygroup } methyl] phosphoric acid, obtain compound organic film.
With light transmittance/mist degree analyzer, the light transmittance for measuring compound organic film is 89%, mist degree 25%.With white light, wave The ultraviolet light and wavelength of a length of 365nm is that the ultraviolet light of 254nm irradiates above-mentioned multi-functional photochromic film 60 seconds respectively, is used The color of compound organic film after colour photometer detection light photograph is respectively orange red, orange red and orange red.
It can be seen that the mist degree of compound organic film is promoted than single layer organic film, but can not show a candle to multi-functional photic Optically variable films, moreover, compound organic film do not have multistable photochromic effect.
By above-mentioned correlation technique scheme (5) ~ (8) once it can be seen from a certain component missing in organic layer, then what is prepared answers It is poor to close organic film light scattering property, and does not have multistable photochromic effect.
In conclusion the beneficial effects of the present invention are: it has used 4 kinds of light scattering properties poor, and itself has not had photic The organic material of color changeable effect has obtained the multistable light with high transparency and mist degree by optimization film composition and structure Cause optically variable films;Moreover, compound if lacking a certain material for not having photochromic properties itself in organic layer The mist degree decline of organic film, photochromic effect disappear.
Therefore, the technical solution of the claims in the present invention has marked improvement outstanding, produces unexpected technology Effect, the creativeness with patent statute.
Specific embodiment
The present invention is further described below by example.
Embodiment 1
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 25nm thickness, the 2- of 25nm thickness are successively deposited on plate (R)-[{ [1- (6- amino -9H- purine -9- base) of (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 25nm thickness Propyl -1- base] oxygroup methyl] phosphoric acid, 25nm thickness N- (the chloro- 2- tolyl of 5-) adamantane amide, obtain multi-functional photochromic Film.
With light transmittance/mist degree analyzer, the light transmittance for measuring multi-functional photochromic film is 92%, mist degree 90%.With The ultraviolet light that the ultraviolet light and wavelength that white light, wavelength are 365nm are 254nm irradiates above-mentioned multi-functional photochromic film respectively 60 seconds, the color of the multi-functional photochromic film after being shone with colour photometer detection light was respectively red, yellow and blue.
Embodiment 2
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 40nm thickness, the 2- of 40nm thickness are successively deposited on plate (R)-[{ [1- (6- amino -9H- purine -9- base) of (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 40nm thickness Propyl -1- base] oxygroup methyl] phosphoric acid, 40nm thickness N- (the chloro- 2- tolyl of 5-) adamantane amide, obtain multi-functional photochromic Film.
With light transmittance/mist degree analyzer, the light transmittance for measuring multi-functional photochromic film is 88%, mist degree 94%.With The ultraviolet light that the ultraviolet light and wavelength that white light, wavelength are 365nm are 254nm irradiates above-mentioned multi-functional photochromic film respectively 60 seconds, the color of the multi-functional photochromic film after being shone with colour photometer detection light was respectively red, yellow and blue.
Embodiment 3
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 30nm thickness, the 2- of 35nm thickness are successively deposited on plate (R)-[{ [1- (6- amino -9H- purine -9- base) of (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 30nm thickness Propyl -1- base] oxygroup methyl] phosphoric acid, 40nm thickness N- (the chloro- 2- tolyl of 5-) adamantane amide, obtain multi-functional photochromic Film.
With light transmittance/mist degree analyzer, the light transmittance for measuring multi-functional photochromic film is 89%, mist degree 91%.With The ultraviolet light that the ultraviolet light and wavelength that white light, wavelength are 365nm are 254nm irradiates above-mentioned multi-functional photochromic film respectively 60 seconds, the color of the multi-functional photochromic film after being shone with colour photometer detection light was respectively red, yellow and blue.
Embodiment 4
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 40nm thickness, the 2- of 25nm thickness are successively deposited on plate (R)-[{ [1- (6- amino -9H- purine -9- base) of (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 25nm thickness Propyl -1- base] oxygroup methyl] phosphoric acid, 25nm thickness N- (the chloro- 2- tolyl of 5-) adamantane amide, obtain multi-functional photochromic Film.
With light transmittance/mist degree analyzer, the light transmittance for measuring multi-functional photochromic film is 91%, mist degree 93%.With The ultraviolet light that the ultraviolet light and wavelength that white light, wavelength are 365nm are 254nm irradiates above-mentioned multi-functional photochromic film respectively 60 seconds, the color of the multi-functional photochromic film after being shone with colour photometer detection light was respectively red, yellow and blue.
Embodiment 5
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 37nm thickness, the 2- of 38nm thickness are successively deposited on plate (R)-[{ [1- (6- amino -9H- purine -9- base) of (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 29nm thickness Propyl -1- base] oxygroup methyl] phosphoric acid, 26nm thickness N- (the chloro- 2- tolyl of 5-) adamantane amide, obtain multi-functional photochromic Film.
With light transmittance/mist degree analyzer, the light transmittance for measuring multi-functional photochromic film is 89%, mist degree 94%.With The ultraviolet light that the ultraviolet light and wavelength that white light, wavelength are 365nm are 254nm irradiates above-mentioned multi-functional photochromic film respectively 60 seconds, the color of the multi-functional photochromic film after being shone with colour photometer detection light was respectively red, yellow and blue.

Claims (1)

1. a kind of preparation method of multi-functional photochromic film, which is characterized in that specific step is as follows:
5cm × 5cm × 0.5mm glass plate is placed in vacuum coating equipment, is 2 × 10 in vacuum degree-3Under Pa, in glass plate On that 8- amino -4- oxo -2- (1H-TETRAZOLE -5- base) -4H-1- chromene of 25 ~ 40nm thickness, 25 ~ 40nm is successively deposited is thick (R)-[{ [1- (6- amino -9H- purine-of 2- (the chloro- 3- sulfanilamide (SN) phenyl of 4-)-N- methylhydrazide thioamides, 25 ~ 40nm thickness 9- yl) propyl -1- base] oxygroup methyl] phosphoric acid, 25 ~ 40nm thickness N- (the chloro- 2- tolyl of 5-) adamantane amide, obtain multi-functional Photochromic film;
Wherein the performance of multi-functional photochromic film is that light transmittance is 88 ~ 92%, and mist degree is 90 ~ 94%;It is with white light, wavelength The ultraviolet light and wavelength of 365nm is that the ultraviolet light of 254nm irradiates multi-functional photochromic film 60 seconds respectively, more function after illumination The color of energy photochromic film is respectively red, yellow and blue.
CN201910720335.3A 2019-08-06 2019-08-06 A kind of preparation method of multi-functional photochromic film Pending CN110407481A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910720335.3A CN110407481A (en) 2019-08-06 2019-08-06 A kind of preparation method of multi-functional photochromic film

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910720335.3A CN110407481A (en) 2019-08-06 2019-08-06 A kind of preparation method of multi-functional photochromic film

Publications (1)

Publication Number Publication Date
CN110407481A true CN110407481A (en) 2019-11-05

Family

ID=68366067

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910720335.3A Pending CN110407481A (en) 2019-08-06 2019-08-06 A kind of preparation method of multi-functional photochromic film

Country Status (1)

Country Link
CN (1) CN110407481A (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1226267A (en) * 1996-06-17 1999-08-18 光学转变公司 Noval photochromic indeno-fused naphthopyrans
CN1842580A (en) * 2003-07-01 2006-10-04 光学转变公司 Photochromic compounds
CN107502863A (en) * 2017-08-11 2017-12-22 太仓碧奇新材料研发有限公司 The preparation method of blood orange Huang three-stable state photochromic film

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1226267A (en) * 1996-06-17 1999-08-18 光学转变公司 Noval photochromic indeno-fused naphthopyrans
CN1842580A (en) * 2003-07-01 2006-10-04 光学转变公司 Photochromic compounds
CN107502863A (en) * 2017-08-11 2017-12-22 太仓碧奇新材料研发有限公司 The preparation method of blood orange Huang three-stable state photochromic film

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
余丽霞: "N-取代2-(5-氯-2-(金刚基-1-基)-1H-吲哚-3-基)-2-氧代乙酰胺衍生物的合成及其细胞毒活性", 《合成化学》 *
奚同庚: "《带翼的金属 科学发现之旅》", 31 August 2018, 上海科学技术文献出版社 *
安敏: "普仑司特中间体的8-氨基-4-氧代-2-(1H-四唑-5-基)-4H-1-苯并吡喃的合成", 《合成化学》 *
尹洪峰等编著: "《普通高等教育十二五规划教材 功能复合材料》", 30 August 2013, 北京冶金工业出版社 *
张春红: "《高分子材料》", 29 February 2016, 北京航空航天大学出版社 *
李善君: "《高分子光化学原理及应用》", 31 January 1993, 上海复旦大学出版社 *
陈明桂: "含有苯磺酰胺基团1,2,4-三唑和噻二唑类化合物的设计、合成及抑菌活性", 《应用化学》 *
黄小光: "富马酸替诺福韦二吡呋酯杂质的合成", 《合成化学》 *

Similar Documents

Publication Publication Date Title
DE60020609T2 (en) CORROSION-RESISTANT LIGHT-CONTROLLING ELEMENT
CN105425327B (en) A kind of cholesteric liquid crystal and its reflective circular polarizing disk and preparation method
DE3105342A1 (en) "METHOD FOR PRODUCING A PRESSURE-SENSITIVE ADHESIVE TAPE FROM A PHOTOACTIVE MIXTURE OF ACRYLOMONERS AND A MULTINUINED CHROMOPHOR-SUBSTITUTED HALOGENMETHYL-S-TRIAZINE AND THIS ADHESIVE TAPE"
CN103635837B (en) Polarization photochromic article
CN109721692A (en) A kind of optical thin film and preparation method thereof of the Liquid Crystal/Polymer composite material containing quantum dot
CN107637174B (en) Luminescent film
JP3451281B2 (en) UV blocking fluoropolymer film
CN110095896A (en) A kind of preparation method of the light modulation film based on Liquid Crystal/Polymer composite material
EP1629309A1 (en) Polymer film with a helical molecular structure
KR20210057549A (en) UV Self-healing polymer and manufacturing method of the same
CN105062504B (en) A kind of brightness enhancement film polymerizability liquid-crystal composition
JP2004504474A (en) Manufacturing method of photochromic molded product
CN110407481A (en) A kind of preparation method of multi-functional photochromic film
JPH09508158A (en) Acrylic latex capable of forming photocrosslinkable film
JP5243826B2 (en) Optical film absorption band control method, optical film manufacturing method, optical film, color purity improving sheet, and image display device
JP2007171891A (en) Backlight structure of liquid crystal display device
CN104212463B (en) Orientation and smoothing material composition, display unit and Show Color inflation method
CN103881038B (en) Containing the Preparation method and use of the triblock copolymer of spiropyran groups
TW201728921A (en) Optical film for eyewear, and functional film for eyewear, optical laminate for eyewear, and eyewear which have same
JP2009227866A (en) Method for controlling absorption zone of optical film, method for producing optical film, optical film, color purity-improved sheet, and image display device
CN105216390B (en) A kind of novel pressure color-changing flexible membrane material
DE10105278A1 (en) Adhesives containing polyvinyl alkyl ethers
TW200533732A (en) Barrier coating composition containing a liquid crystalline polymer as well as a device containing this barrier coating composition
WO2024070771A1 (en) Laminated body, and virtual reality display device
DE19946898A1 (en) Adhesives for frozen substrates

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication

Application publication date: 20191105

RJ01 Rejection of invention patent application after publication