CN109400816A - A kind of discoloration, the colour fading method of change colour gel resin and its synthetic method and the gel of uV curable - Google Patents
A kind of discoloration, the colour fading method of change colour gel resin and its synthetic method and the gel of uV curable Download PDFInfo
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- CN109400816A CN109400816A CN201810971778.5A CN201810971778A CN109400816A CN 109400816 A CN109400816 A CN 109400816A CN 201810971778 A CN201810971778 A CN 201810971778A CN 109400816 A CN109400816 A CN 109400816A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F261/00—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00
- C08F261/02—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols
- C08F261/04—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols on to polymers of vinyl alcohol
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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Abstract
A kind of discoloration, the colour fading method of change colour gel resin and its synthetic method and the gel of uV curable, the present invention relates to discoloration gel and its synthetic method and discolorations, colour fading method.Slow, time length technical problem that the present invention is to solve the process for preparing sol-gel gelation rates of existing discoloration gel.Discoloration gel resin of the invention is made of 1 polyvinyl alcohol, amino acid, catalyst, modifying agent, photoactive monomer, photoinitiator and solvent.Polyvinyl alcohol is added in solvent, with amino acid graft reaction, then sequentially adds catalyst, modifying agent, photoinitiator and photoactive monomer is added after dialysis, obtains the discoloration gel resin of uV curable.Resin ultraviolet light irradiation can be solidified into gel, and gel impregnates i.e. changeable colour in metal ion solution, impregnate in colour fading liquid, can fade, can be used as camouflage material.
Description
Technical field
The present invention relates to discoloration gel and its synthetic method and discolorations, colour fading method.
Background technique
Off-color material refers to as external environmental condition changes and occur the substance of color change.According to cause discoloration because
The difference of element, off-color material can be divided into photochromic, electrochromism, thermochromism and soda acid mutagens color, humectation color and pressure and cause
Off-color material etc..That is off-color material have can with intensity of illumination different, atmospheric environment temperature are different, atmospheric humidity not
Together, pressure difference etc., reversible change occurs for structure, so as to cause its reversible change to visible absorption spectrum, color
The characteristic of reversible change occurs.It is very widely used as a kind of intelligent colour development material, as instrument thermal recording medium,
Thermally indicating material etc..Furthermore off-color material high-technology field application it is also very much, such as in terms of play the part of emphatically
The role wanted.
Gel change colour as a kind of emerging off-color material, it has all characteristics of off-color material.Existing discoloration is solidifying
Glue has electrochromism gel, thermochromism gel etc., and preparation method is sol-gel method, but this preparation method is taken
Between it is long, gelation rate is slow.
Summary of the invention
Slow, time length skill that the present invention is to solve the process for preparing sol-gel gelation rates of existing discoloration gel
Art problem, and discoloration, the colour fading method of change colour gel resin and its synthetic method and the gel of a kind of uV curable are provided.
The discoloration gel resin of uV curable of the invention is by mass parts ratio by 100 parts of polyvinyl alcohol (PVA), 30
~50 parts of amino acid, 0.5~1 part of catalyst, 15~50 parts of modifying agent, 1~5 part of photoactive monomer, 1~5 part of photoinitiator and
1000~1300 parts of solvents are made.
The preparation method of the discoloration gel resin of above-mentioned uV curable, sequentially includes the following steps:
One, by mass parts ratio weigh 100 parts of polyvinyl alcohol (PVA), 30~50 parts of amino acid, 0.5~1 part of catalyst,
15~50 parts of modifying agent, 1~5 part of photoactive monomer, 1~5 part of photoinitiator and 1000~1300 parts of solvents;
Two, PVA and solvent are added in reactor, 3~5h is stirred under conditions of temperature is 50~70 DEG C, is then existed
It is stored at room temperature 12~24 hours, obtains PVA dispersion liquid;
Three, the concentrated sulfuric acid is added into PVA dispersion liquid and adjusts pH value to 3~4, then heats to 115~120 DEG C, adds
Amino acid, and stir 6~10h;Then 45~50 DEG C are cooled to, the PVA dispersion liquid of grafted amino group carboxylic acid is obtained;
Four, into the PVA dispersion liquid of grafted amino group carboxylic acid be added 1~2mol/L sodium hydroxide solution adjust pH to 6~
7, catalyst is then added, stirs evenly, obtains dispersion liquid A;
Five, modifying agent is added into dispersion liquid A, stirs evenly, then heat to 55~60 DEG C and continue 5~10h of stirring, obtain
To dispersion liquid B;
Six, it by bag filter 48~72h of dialysis of dispersion liquid B Mv500, obtains, dispersion liquid C;
Seven, photoinitiator and photoactive monomer are added into dispersion liquid C, stirs evenly, obtains the change of uV curable
Color gel resin.
Discoloration gel resin of the invention, 10s can be solidified into gel under ultraviolet light.
The color changing method of gel is: gel being placed in colour developing metal ion solution and is impregnated, is i.e. changeable colour.
The colour fading method of gel is: first pressing the hydrochloric acid solution that concentration is 1~1.2mol/L with saturation triacetamide solution
Volume ratio 1:(3.5~4) ratio mixing, obtain colour fading liquid;Foxed gel is placed in colour fading liquid again and is impregnated, can be taken off
Color.
The present invention is using polyvinyl alcohol as backbone material, by the grafted amino group carboxylic acids functional group on polyvinyl alcohol backbones,
Achieve the purpose that colour developing by the chelation between amino carboxylic acid functional group and colour developing metal cation, then in polyvinyl alcohol master
It is grafted upper unsaturated activity double key on chain, ultraviolet light curing reaction can be carried out with crosslinking agent and photoinitiator.
The discoloration gel resin of uV curable of the invention can be by metals such as copper ion, cobalt ions or iron ions
Soaking time is that 10~30s realizes discoloration, fast response time, and color stability in solion.The gel of discoloration is fading
Liquid is impregnated 8~10 minutes and can be faded.Colour developing, colour fading can be alternately.
Discoloration gel resin discoloration gel resin of the invention is at low cost, and preparation method is simple, and discoloration gel is applicable as
Camouflage material.
Detailed description of the invention
Fig. 1 is photo of the discoloration gel resin of uV curable prepared by embodiment 1 after photocuring;
Fig. 2 is that discoloration gel resin prepared by embodiment 1 impregnates the photo after changing colour through copper chloride solution;
Fig. 3 is photo of the discoloration gel resin of uV curable prepared by embodiment 2 after photocuring;
Fig. 4 is the discoloration gel resin of the preparation of embodiment 2 through CoCl3Solution impregnates the photo after discoloration.
Specific embodiment
Specific embodiment 1: the discoloration gel resin of the uV curable of present embodiment by mass parts ratio by
100 parts of polyvinyl alcohol (PVA), 30~50 parts of amino acid, 0.5~1 part of catalyst, 15~50 parts of modifying agent, 1~5 part of photolytic activity
Monomer, 1~5 part of photoinitiator and 1000~1300 parts of solvents are made.
Specific embodiment 2: the present embodiment is different from the first embodiment in that the amino acid is paddy ammonia
Acid, lysine, aspartic acid or arginine;Other are same as the specific embodiment one.
Specific embodiment 3: the present embodiment is different from the first and the second embodiment in that the catalyst is N-
Dimethylamino naphthyridine, pyridine or dicyclohexylcarbodiimide;Other are the same as one or two specific embodiments.
Specific embodiment 4: the modifying agent unlike one of present embodiment and specific embodiment one to three is
Maleic anhydride, acryloyl chloride or methacrylate;Other are identical as one of specific embodiment one to three.
Specific embodiment 5: photolytic activity described unlike one of present embodiment and specific embodiment one to four
Monomer is N,N methylene bis acrylamide, allyl methacrylate, Diallyl Itaconate propyl diester or methacrylate
Glycol ester;Other are identical as one of specific embodiment one to four.
Specific embodiment 6: described light-initiated unlike one of present embodiment and specific embodiment one to five
Agent is the mixture of one or both of photoinitiator 1173, photoinitiator TPO-L, photoinitiator 819;Other and specific reality
It is identical to apply one of mode one to five.
Specific embodiment 7: solvent described unlike one of present embodiment and specific embodiment one to six is
Dimethyl sulfoxide, N,N-dimethylformamide or dimethyl adipate;Other are identical as one of specific embodiment one to six.
Specific embodiment 8: the preparation side of the discoloration gel resin of uV curable described in specific embodiment one
Method sequentially includes the following steps:
One, by mass parts ratio weigh 100 parts of polyvinyl alcohol (PVA), 30~50 parts of amino acid, 0.5~1 part of catalyst,
15~50 parts of modifying agent, 1~5 part of photoactive monomer, 1~5 part of photoinitiator and 1000~1300 parts of solvents;
Two, PVA and solvent are added in reactor, 3~5h is stirred under conditions of temperature is 50~70 DEG C, is then existed
It is stored at room temperature 12~24 hours, obtains PVA dispersion liquid;
Three, the concentrated sulfuric acid is added into PVA dispersion liquid and adjusts pH value to 3~4, then heats to 115~120 DEG C, adds
Amino acid, and stir 6~10h;Then 45~50 DEG C are cooled to, the PVA dispersion liquid of grafted amino group carboxylic acid is obtained;
Four, into the PVA dispersion liquid of grafted amino group carboxylic acid be added 1~2mol/L sodium hydroxide solution adjust pH to 6~
7, catalyst is then added, stirs evenly, obtains dispersion liquid A;
Five, modifying agent is added into dispersion liquid A, stirs evenly, then heat to 55~60 DEG C and continue 5~10h of stirring, obtain
To dispersion liquid B;
Six, it by bag filter 48~72h of dialysis of dispersion liquid B Mv500, obtains, dispersion liquid C;
Seven, photoinitiator and photoactive monomer are added into dispersion liquid C, stirs evenly, obtains the change of uV curable
Color gel resin.
Specific embodiment 9: present embodiment is from the mixing speed unlike specific embodiment eight in step 2
300~500r/min;Other are identical as specific embodiment eight.
Specific embodiment 10: present embodiment in step 3, stirs speed unlike specific embodiment eight or nine
Degree is 300~500r/min;Other are identical as specific embodiment eight or nine.
Specific embodiment 11: it is stirred in step 4 unlike one of present embodiment and specific embodiment eight to ten
Mixing speed is 300~500r/min, and mixing time is 10~20min;Other are identical as one of specific embodiment eight to ten.
Specific embodiment 12: present embodiment from unlike specific embodiment eight to one of 11 in step 5
Mixing speed is 300~500r/min, 10~20min of mixing time;Other are identical as specific embodiment eight to one of 11.
Specific embodiment 13: present embodiment from unlike specific embodiment eight to one of 12 in step 7
Mixing speed is 300~500r/min, 5~10min of mixing time;Other are identical as specific embodiment eight to one of 12.
Specific embodiment 14: after the discoloration gel resin of the uV curable of present embodiment is solidified into gel,
The color changing method of gel is to be placed on gel in colour developing metal ion solution to impregnate, i.e. changeable colour.
Solidification described in present embodiment be by the discoloration gel resin of uV curable under ultraviolet light 10s,
It is i.e. curable, obtain gel.
Specific embodiment 15: present embodiment wherein metal ion solution unlike specific embodiment 14
Concentration be 0.1~0.5mol/L;It is other identical as specific embodiment 14.
Specific embodiment 16: present embodiment and metal ion unlike specific embodiment 14 or 15 are molten
Liquid is copper ion solution, cobalt ions solution or ferric ion solutions;It is other identical as specific embodiment 14 or 15.
Specific embodiment 17: when present embodiment is impregnated unlike specific embodiment 14 to one of 16
Between be 10~30s;It is other identical as specific embodiment 14 to one of 16.
Specific embodiment 18: the colour fading method of present embodiment gel is: the salt for being first 1~1.2mol/L by concentration
Acid solution and saturation triacetamide solution 1:(3.5~4 by volume) ratio mix, obtain colour fading liquid;It again will be foxed
Gel, which is placed in colour fading liquid, to be impregnated, and can be faded.
Specific embodiment 19: present embodiment is when impregnating from soaking time unlike specific embodiment 18
Between be 8~10min;It is identical as specific embodiment 18.
Beneficial effects of the present invention are verified with embodiment below:
Embodiment 1: the uV curable of the present embodiment discoloration gel resin preparation method, according to the following steps into
Row:
One, 100 parts of polyvinyl alcohol (PVA), 50 parts of glutamic acid, 0.8 part of catalyst n-diformazan ammonia are weighed by mass parts ratio
Yl pyridines, 16 parts of modifying agent maleic anhydrides, 5 parts of photoactive monomer N,N methylene bis acrylamides, 3 parts of photoinitiators
1173 and 1300 parts of solvent dimethyl sulfoxides;
Two, PVA and dimethyl sulfoxide are added in reactor, using oil bath heating, under conditions of temperature is 60 DEG C,
5h is stirred with the mixing speed of 400r/min, is then being stored at room temperature 18 hours, is obtaining PVA dispersion liquid;
Three, the concentrated sulfuric acid is added into PVA dispersion liquid and adjusts pH value to 4, then heats to 118 DEG C, adds glutamic acid, with
The mixing speed of 400r/min stirs 10h;Then 50 DEG C are cooled to, the PVA dispersion liquid of grafted amino group carboxylic acid is obtained;
Four, the sodium hydroxide solution that 2mol/L is added into the PVA dispersion liquid of grafted amino group carboxylic acid adjusts pH to 6.5, so
Catalyst n-dimethylamino naphthyridine is added afterwards, 10min is stirred with the mixing speed of 400r/min, obtains dispersion liquid A;
Five, modifying agent maleic anhydride is added into dispersion liquid A, 10min is stirred with the mixing speed of 400r/min, so
It is warming up to 60 DEG C afterwards to continue to stir 5h with the mixing speed of 400r/min, obtains dispersion liquid B;
Six, it by the bag filter dialysis 48h of dispersion liquid B Mv500, obtains, dispersion liquid C;
Seven, photoinitiator 1173 and photoactive monomer N, N- methylene-bisacrylamide are added into dispersion liquid C, with
The mixing speed of 300r/min stirs 10min, obtains the discoloration gel resin of uV curable.
The ultraviolet light 10s that the discoloration gel resin of uV curable manufactured in the present embodiment is utilized to 365nm, obtains
Curing rate to gel, the resin is fast, and solidification can be completed in 10s or so.The photo of the gel is as shown in Figure 1.
The gel obtained after solidification is immersed in after impregnating 30s in the copper chloride solution that concentration is 0.5mol/L and is taken out, it can
Observing gel uniformly becomes blue, and photo is as shown in Fig. 2, its rgb value is 153,172,150.It is hereby understood that the gel
Color change quickly.
The hydrochloric acid solution that concentration is 1mol/L is mixed with the ratio for being saturated triacetamide solution 2:7 by volume first, is obtained
To colour fading liquid;Foxed gel is placed in colour fading liquid again and is impregnated, the color change of gel is directly observed, after impregnating 8min,
Gel fades completely, and transparence is presented, that is, realizes the colour fading of gel.
The gel obtained after solidification is immersed in the CoCl that concentration is 0.5mol/L3It takes out, can be observed after 30s in solution
Gel becomes red.Gel after discoloration is immersed in the hydrochloric acid solution of 1mol/L and is saturated triacetamide solution by volume
In the colour fading liquid mixed for 2:7, the color change of gel is directly observed, after impregnating 7min, gel fades completely, presents saturating
Bright shape realizes the colour fading of gel.
Embodiment 2: the uV curable of the present embodiment discoloration gel resin preparation method, according to the following steps into
Row:
One, 100 parts of polyvinyl alcohol (PVA), 40 parts of glutamic acid, 0.64 part of catalyst n-diformazan ammonia are weighed by mass parts ratio
Yl pyridines, 25 parts of modifying agent maleic anhydrides, 3 parts of photoactive monomer N,N methylene bis acrylamides, 5 parts of photoinitiators
1173 and 1300 parts of solvent dimethyl sulfoxides;
Two, PVA and dimethyl sulfoxide are added in reactor, using oil bath heating, under conditions of temperature is 60 DEG C,
5h is stirred with the mixing speed of 400r/min, is then being stored at room temperature 18 hours, is obtaining PVA dispersion liquid;
Three, the concentrated sulfuric acid is added into PVA dispersion liquid and adjusts pH value to 4, then heats to 118 DEG C, adds glutamic acid, with
The mixing speed of 400r/min stirs 10h;Then 50 DEG C are cooled to, the PVA dispersion liquid of grafted amino group carboxylic acid is obtained;
Four, the sodium hydroxide solution that 2mol/L is added into the PVA dispersion liquid of grafted amino group carboxylic acid adjusts pH to 6.5, so
Catalyst n-dimethylamino naphthyridine is added afterwards, 10min is stirred with the mixing speed of 400r/min, obtains dispersion liquid A;
Five, modifying agent maleic anhydride is added into dispersion liquid A, 10min is stirred with the mixing speed of 400r/min, so
It is warming up to 60 DEG C afterwards to continue to stir 5h with the mixing speed of 400r/min, obtains dispersion liquid B;
Six, it by the bag filter dialysis 48h of dispersion liquid B Mv500, obtains, dispersion liquid C;
Seven, photoinitiator 1173 and photoactive monomer N, N- methylene-bisacrylamide are added into dispersion liquid C, with
The mixing speed of 300r/min stirs 10min, obtains the discoloration gel resin of uV curable.
The ultraviolet light 10s that the discoloration gel resin of uV curable manufactured in the present embodiment is utilized to 365nm, obtains
Curing rate to gel, the resin is fast, and solidification can be completed in 10s or so.The photo of the gel is as shown in Figure 3.
The gel obtained after solidification is immersed in after impregnating 30s in the copper chloride solution that concentration is 0.5mol/L and is taken out, it can
Observe that gel becomes blue.It is hereby understood that the color change of the gel is quickly.Gel after discoloration is immersed in 1mol/L
Hydrochloric acid solution and saturation triacetamide solution be by volume the direct face of observation gel in colour fading liquid that 2:7 is mixed
Color change, after impregnating 8min, gel fades completely, and transparence is presented, that is, realizes the colour fading of gel.
The gel obtained after solidification is immersed in the CoCl that concentration is 0.5mol/L3It takes out, can be observed after 30s in solution
Gel equably becomes red, and photo is as shown in figure 4, its rgb value is 201,166,146.By after discoloration gel immerse with
The hydrochloric acid solution and saturation triacetamide solution of 1mol/L is in the colour fading liquid that 2:7 is mixed by volume, and directly observation is solidifying
The color change of glue, after impregnating 8min, gel fades completely, and transparence is presented, that is, realizes the colour fading of gel.
Claims (10)
1. a kind of discoloration gel resin of uV curable, it is characterised in that the discoloration gel resin by mass parts ratio by
100 parts of polyvinyl alcohol, 30~50 parts of amino acid, 0.5~1 part of catalyst, 15~50 parts of modifying agent, 1~5 part of photoactive monomer, 1
~5 parts of photoinitiators and 1000~1300 parts of solvents are made.
2. a kind of discoloration gel resin of uV curable according to claim 1, it is characterised in that the amino
Acid is glutamic acid, lysine, aspartic acid or arginine.
3. a kind of discoloration gel resin of uV curable according to claim 1 or 2, it is characterised in that described urges
Agent is N- dimethylamino naphthyridine, pyridine or dicyclohexylcarbodiimide.
4. a kind of discoloration gel resin of uV curable according to claim 1 or 2, it is characterised in that the modification
Agent is maleic anhydride, acryloyl chloride or methacrylate.
5. a kind of discoloration gel resin of uV curable according to claim 1 or 2, it is characterised in that the light
Activated monomer is N,N methylene bis acrylamide, allyl methacrylate, Diallyl Itaconate propyl diester or double methyl-props
Olefin(e) acid glycol ester.
6. a kind of discoloration gel resin of uV curable according to claim 1 or 2, it is characterised in that the light
Initiator is the mixture of one or both of photoinitiator 1173, photoinitiator TPO-L, photoinitiator 819.
7. a kind of discoloration gel resin of uV curable according to claim 1 or 2, it is characterised in that described is molten
Agent is dimethyl sulfoxide, N,N-dimethylformamide or dimethyl adipate.
8. a kind of uV curable discoloration gel resin preparation method, it is characterised in that this method according to the following steps into
Row:
One, by mass parts ratio weigh 100 parts of polyvinyl alcohol, 30~50 parts of amino acid, 0.5~1 part of catalyst, 15~50 parts change
Property agent, 1~5 part of photoactive monomer, 1~5 part of photoinitiator and 1000~1300 parts of solvents;
Two, PVA and solvent are added in reactor, 3~5h are stirred under conditions of temperature is 50~70 DEG C, then in room temperature
12~24 hours are stood, PVA dispersion liquid is obtained;
Three, the concentrated sulfuric acid is added into PVA dispersion liquid and adjusts pH value to 3~4, then heats to 115~120 DEG C, adds amino
Acid, and stir 6~10h;Then 45~50 DEG C are cooled to, the PVA dispersion liquid of grafted amino group carboxylic acid is obtained;
Four, the sodium hydroxide solution that 1~2mol/L is added into the PVA dispersion liquid of grafted amino group carboxylic acid adjusts pH to 6~7, so
After catalyst is added, stir evenly, obtain dispersion liquid A;
Five, modifying agent is added into dispersion liquid A, stirs evenly, then heat to 55~60 DEG C and continue 5~10h of stirring, divided
Dispersion liquid B;
Six, it by bag filter 48~72h of dialysis of dispersion liquid B Mv500, obtains, dispersion liquid C;
Seven, photoinitiator and photoactive monomer are added into dispersion liquid C, stirs evenly, the discoloration for obtaining uV curable is solidifying
Gum resin.
9. uV curable discoloration gel color changing method, it is characterised in that this method be gel is placed on colour developing metal from
It is impregnated in sub- solution, i.e. changeable colour.
10. uV curable discoloration gel colour fading method, it is characterised in that this method is: first by concentration be 1~
The hydrochloric acid solution of 1.2mol/L and saturation triacetamide solution 1:(3.5~4 by volume) ratio mix, obtain colour fading liquid;
Foxed gel is placed in colour fading liquid again and is impregnated, can be faded.
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CN113388052A (en) * | 2021-06-28 | 2021-09-14 | 绍兴迪飞新材料有限公司 | Intelligent dynamic dimming film, preparation process thereof, dimming glass and dimming glass system |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN113388052A (en) * | 2021-06-28 | 2021-09-14 | 绍兴迪飞新材料有限公司 | Intelligent dynamic dimming film, preparation process thereof, dimming glass and dimming glass system |
CN113388052B (en) * | 2021-06-28 | 2022-09-02 | 绍兴迪飞新材料有限公司 | Intelligent dynamic dimming film, preparation process thereof, dimming glass and dimming glass system |
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