CN103897574A - Photochromic composition coating, photochromic composition coating product and preparation method of photochromic composition coating product - Google Patents
Photochromic composition coating, photochromic composition coating product and preparation method of photochromic composition coating product Download PDFInfo
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- CN103897574A CN103897574A CN201410119488.XA CN201410119488A CN103897574A CN 103897574 A CN103897574 A CN 103897574A CN 201410119488 A CN201410119488 A CN 201410119488A CN 103897574 A CN103897574 A CN 103897574A
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Abstract
The invention discloses a photochromic composition coating, a photochromic composition coating product and a preparation method of the photochromic composition coating product. The coating comprises at least one photochromic factor in a photochromic amount, polymeric polylol of which the number-average molecular weight is 200-2,000, at least one isocyanate group-containing substance of which the number-average molecular weight is 150-300, at least one vinyl-containing substance and auxiliary materials, wherein main chains of the polymeric polylol, isocyanate group-containing substance and vinyl-containing substance contain at least one of carbonic ester, aromatic series or aliphatic series. The coating product comprises a white sheet, dyed sheet or polarized sheet serving as a substrate. The preparation method of the coating product comprises the following steps: coating the substrate with the photochromic composition coating; fixing the coating by adopting thermocuring and photocuring. The photochromic composition coating has the advantages that air bubbles are not produced when the substrate is coated with the coating, and the coating is high in hardness and wear-resistant.
Description
Technical field
The present invention relates to a kind of optical material, relate in particular to the preparation method of a kind of photochromic composition coating and photochromic composition coated products and these goods.
Background technology
Existing photochromic plastics are in photochromic plastics, to add the photochromic factor (photochromic dyes), or add the photochromic factor by Surface absorption plavini.Under sunlight (having ultraviolet ray), the easy variable color of the photochromic plastics of this class (being colored), after keeping out of the sun, the photochromic plastics of this class recover original color (fading).But there is following shortcoming in current photochromic plastics: photochromic surface of plastic products easily produces bubble or sends out mist, or photochromic surface of plastic products hardness is high, easy to wear etc.
Summary of the invention
Goal of the invention: the first object of the present invention is to provide one and does not produce the higher and anti abrasive photochromic composition coating of bubble, hardness;
The second object of the present invention is to provide a kind of photochromic composition coated products;
The 3rd object of the present invention is to provide the preparation method of this photochromic composition coated products.
Technical scheme: photochromic composition coating of the present invention, it is characterized in that comprising following component: the material containing isocyanate group, at least one material and auxiliary material containing vinyl that the photochromic factor of at least one photochromic amount, the polymerized polyalcohol that number-average molecular weight (Mn) is 200-2000, at least one number-average molecular weight (Mn) are 150-300, wherein, described polymerized polyalcohol, containing containing at least one in carbonic ether, aromatic series or aliphatics on the material of isocyanate group and the main chain containing the material of vinyl.
Wherein, described polymerized polyalcohol is at least one in PAO and PO, PCDO; The described material containing isocyanate group is at least one in IPDI, HDI, H12MDI, TDI, MDI; The described material containing vinyl is polymethylmethacrylate; Described auxiliary material is solvent, initiator, catalyzer, ultra-violet stabilizer and tensio-active agent.
Said components is made by following weight proportion:
Described PAO is formed by the monomer polymerization with following general formula:
Wherein, R1 is H, CH3, OH or SH, and R2 is H, CH3, OH or SH, and R3 is H, CH3, C2H5, OH or SH, and R4 is C5H9, OH or SH.
Described PAO specifically makes by following reaction:
Wherein, temperature of reaction 90-110 DEG C, the reaction times is 3.8-4.2h, and in reaction process, uses initiator.
Above-mentioned reactant is made by following weight proportion:
Photochromic composition coated products of the present invention, comprises matrix and is coated in the photochromic composition coating on matrix.
Wherein, described matrix is white sheet, staining section or polaroid.
The preparation method of photochromic composition coated products of the present invention, is first coated in photochromic composition coating on matrix, then adopts the fixing coating of mode of thermofixation and photocuring simultaneously.
Wherein, the described photocuring time is more than 1h, and described thermal curing time is 1min.
Beneficial effect: compared with prior art, its remarkable advantage is in the present invention: 1, photochromic composition coating of the present invention does not produce bubble after being coated on matrix, and coating hardness is higher, not easy to wear; 2, coating of the present invention can be used for specific refractory power 1.499,1.56, the common eyeglass of 1.60,1.67,1.74 grades, and variable color sheet and polaroid; 3, photochromic composition coated products long service life of the present invention, is used 1 year above almost without damaging; 4, the preparation method of coated products of the present invention adopts thermofixation and photocuring to carry out simultaneously, and solidification effect is good.
Embodiment:
Below technical scheme of the present invention is described further.
Photochromic composition coating (hereinafter to be referred as coating) is the photochromic factor is joined to preparation in corresponding lysate and obtain, the main component of this lysate is urethane or the material (being preferably acrylic) containing vinyl (band vinyl group), and in prior art, the two selects one.These two kinds of lysates respectively have quality, and wherein, urethane easily regulates physical property, but synthesis condition is comparatively harsh, and for example the reaction times is longer; Acrylic is compared with urethane, and it is synthetic easily carries out, and the reaction times is short, but is difficult to control its physical property.The present invention is mixed to get these two kinds of lysates (urethane and acrylic) composition of required physical property, and reaction easily carry out, consuming time shorter.
Urethane of the present invention is by polymerized polyalcohol (band OH group) and synthetic containing the material (band NCO group) of isocyanate group.Wherein, polymerized polyalcohol number-average molecular weight (Mn) through test of many times the present invention screening is 200-2000, preferably Mn is 200-1000, can ensure not send out mist and hardness and transparency after coating applies better, and this number-average molecular weight is measured (lower same) by polystyrene chromatography method; Meanwhile, the heterogeneity index of this polymerized polyalcohol, below 2.0, can ensure that coatingsurface is comparatively even.Polymerized polyalcohol is at least one in PAO and PO, PCDO, and the coating solution hardness making is better, is beneficial to the dissolving of the photochromic factor.
PO is polyvalent alcohol, and for example, purchased from the carbonate polyol (carbonate polyol) of Aldrich company, its number-average molecular weight (Mn) is 1000;
PCDO(polycarbonatediol) be polycarbonate diol, also can be purchased from Aldrich company, its number-average molecular weight (Mn) is 800;
PAO（Polyacrylol）
Structural formula:
Molecular formula: C14H24O5; Its number-average molecular weight (Mn): 273.
PAO of the present invention forms by following monomer polymerization:
r1:H, CH3, OH or SH,
R2:H, CH3, OH or SH,
R3:H, CH3, C2H5, OH or SH,
R4:C5H9, OH or SH.
PAO specifically makes by following reaction:
Wherein, temperature of reaction 90-110 DEG C, preferably temperature is 100 DEG C; Reaction times is 3.8-4.2h, and preferably the time is 4h, and in reaction process, uses initiator V-65(2,2'-Azobis(2,4-dimethylvaleronitrile)).
Reactant ratio and reaction conditions table specific as follows:
Table 1
The present invention is 150-300 containing the number-average molecular weight (Mn) of the material of isocyanate group, is specially at least one in IPDI, HDI, H12MDI, TDI, MDI.
Wherein,
IPDI(isophorone diisocyante), isophorone diisocyanate, C12H18N2O2, number-average molecular weight (Mn) is 222.3, purchased from Aldrich company.
Its molecular formula is
HDI(1,6-hexamethylene diisocyanate), hexamethylene diisocyanate, C8H12N2O2, number-average molecular weight (Mn) is 168.19, purchased from Aldrich company.
Its molecular formula is
TDI(toluene diisocyante), tolylene diisocyanate, C9H6N2O2, number-average molecular weight (Mn) is 174.2, purchased from Aldrich company.
Its molecular formula is
In addition, H12MDI and MDI are also purchased from Aldrich company.
The present invention, containing the material of vinyl (band vinyl group), is preferably acrylic (polymethylmethacrylate).
The present invention use solvent have NMP(n-Methylene-pyrrolidone), Toluene(toluene), methanol(methyl alcohol) or cyclohexanone(pimelinketone) etc., all can be purchased from Aldrich company.Wherein, we find NMP(Chinese name n-methylene pyrrolidine ketone through test of many times, and C5H9NCO5H, number-average molecular weight (Mn) is 99.13) solvability best, urethane and acrylic are organically combined.
Other auxiliary material that the present invention uses:
Initiator, V-65(2,2'-Azobis(2,4-dimethylvaleronitrile)), purchased from Wakco chemicals(Wakco chemical);
Catalyzer, purchased from sankyo organic chemicals-Stann BDC (Dibuthyltin dichloride);
Ultra-violet stabilizer (UV stablizer), purchased from seesorb709;
Tensio-active agent, purchased from BYK company-BYK301.
The photochromic factor (or being called photochromic dyes) that the present invention uses, purchased from vivimed company,
Can be for example:
1, Spirooxazine(spirooxazine), its chemical formula is
2, Spiropyrans(spiro-pyrans), its chemical formula is
3, Chromenes(chromene), its chemical formula is
Each raw material weight proportioning that the present invention prepares coating sees the following form 2:
Table 2
Coating of the present invention is to adopt conventional technique means to make, and all pours glass reaction machine into by all raw materials in table 2, mixes, stirs, and controls various parameters, reaction.
The above-mentioned coating making, its number-average molecular weight, between 500-50000, preferably, between 800-15000, has 5 DEG C of above second-order transition temperatures simultaneously.
The coating making is coated on matrix, be specially: the coating solution (or being called photochromic hardening solution) that drips about 1-2g on the lens surface rotating in the speed of 400-500rpm, drip after upper 5-10 second again the photocuring that carries out the thermofixation (being preferably 1min) of 0.5-1.5min and 1h after the speed rotation 10-20 second with 800-2000rpm and be no more than above 2h, finally obtain photochromic composition coated products (hereinafter to be referred as coated products).
Thermofixation is the method evaporating solvent by physical heating, makes coating sclerosis; Thereby photocuring is to utilize UV-light to cause material generation crosslinking reaction in coating to form new chemical bond and realize coating sclerosis, and therefore these two kinds of methods respectively have quality.And existing coating system can only adopt above-mentioned a kind of curing mode; And the present invention can adopt above-mentioned two kinds of curing modes simultaneously, coating is coated on matrix equably, and after coating curing, hardness is better, partially not soft hard only, lower, the curing speed of power consumption is comparatively fast, easily realize simultaneously.
Above-mentioned matrix is white sheet, staining section or polaroid, and its specific refractory power is between 1.499-1.74; Also can from process thermoset and thermoplastic material, choose organic or inorganic aggretion type substrate.
The coated products that 12 groups of embodiment in table 1 are obtained detects as follows, and detected result is in table 3:
1, the transmitance before the variable color of detection coated products and after variable color
Equipment: Simitsu UV spectrometer;
Colour-change light source: 350nm, 24 DEG C of temperature, 15 seconds time, transmitance is measured wavelength: 490nm.
2, detect bubble and the blue mist situation of coated products
In table 3, X represents do not have, and 0 indicates, △ indicates a bit.
The coating that embodiment 5,6,7,9,10,11,12 makes does not produce bubble and blue mist, and this is the cause that has added urethane and acryl due to lysate.
3, surface hardness is measured
Equipment: the Fisherscope HCV of Fisher Technology Inc. company, model H-100
Method: lens surface is at 10N/mm
2pressure under adhere to after 15 seconds, make measurement of hardness in its 2 μ m degree of depth, get each eyeglass do measure for 2～5 times after the data mean value that obtains.
As shown in Table 3, the coated products surface hardness that embodiment 6,9,10,11,12 makes is very high, and the coated products surface hardness that embodiment 7 makes is higher.
Table 3
Claims (10)
1. a photochromic composition coating, it is characterized in that comprising following component: the material containing isocyanate group, at least one material and auxiliary material containing vinyl that the photochromic factor of at least one photochromic amount, polymerized polyalcohol, at least one number-average molecular weight that number-average molecular weight is 200-2000 are 150-300, wherein, described polymerized polyalcohol, containing containing at least one in carbonic ether, aromatic series or aliphatics on the material of isocyanate group and the main chain containing the material of vinyl.
2. photochromic composition coating according to claim 1, is characterized in that: described polymerized polyalcohol is at least one in PAO and PO, PCDO; The described material containing isocyanate group is at least one in IPDI, HDI, H12MDI, TDI, MDI; The described material containing vinyl is polymethylmethacrylate; Described auxiliary material is solvent, initiator, catalyzer, ultra-violet stabilizer and tensio-active agent.
3. photochromic composition coating according to claim 2, is characterized in that described component makes by following weight proportion:
4. photochromic composition coating according to claim 2, is characterized in that: described PAO is formed by the monomer polymerization with following general formula:
Wherein, R1 is H, CH3, OH or SH, and R2 is H, CH3, OH or SH, and R3 is H, CH3, C2H5, OH or SH, and R4 is C5H9, OH or SH.
5. photochromic composition coating according to claim 4, is characterized in that: described PAO makes by following reaction:
Wherein, temperature of reaction 90-110 DEG C, the reaction times is 3.8-4.2h, and in reaction process, uses initiator.
6. photochromic composition coating according to claim 5, is characterized in that: described reactant is made by following weight proportion:
7. a photochromic composition coated products, is characterized in that: comprise matrix and be coated in the photochromic composition coating on matrix.
8. photochromic composition coated products according to claim 7, is characterized in that: described matrix is white sheet, staining section or polaroid.
9. a preparation method for photochromic composition coated products, is characterized in that: first photochromic composition coating is coated on matrix, then adopts the fixing coating of mode of thermofixation and photocuring simultaneously.
10. the preparation method of photochromic composition coated products according to claim 9, is characterized in that: the described photocuring time is 1-2h, described thermal curing time is 0.5-1.5min.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106634533A (en) * | 2016-12-26 | 2017-05-10 | 北京东方雨虹防水技术股份有限公司 | Thermochromatic polyurethane waterproof paint |
| CN109535888A (en) * | 2018-10-25 | 2019-03-29 | 广州市科涵实业有限责任公司 | A kind of one pack system photochromic coating and preparation method thereof |
| CN110323263A (en) * | 2019-07-10 | 2019-10-11 | 京东方科技集团股份有限公司 | Polaroid, display device |
| CN112708344A (en) * | 2021-01-06 | 2021-04-27 | 光易科技(无锡)有限公司 | Photochromic composition of hyperbranched polyurethane vinyl ether, product and preparation method |
| CN114335894A (en) * | 2021-12-21 | 2022-04-12 | 惠州锂威新能源科技有限公司 | Diaphragm with photochromic coating, preparation method thereof and secondary battery |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1251116A (en) * | 1997-02-21 | 2000-04-19 | Pp工业俄亥俄公司 | Photochromic polyurethane coating and articles having such coating |
| CN1829780A (en) * | 2003-08-06 | 2006-09-06 | Lg化学株式会社 | Photochromic primer composition having high impact resistance and transparent material coated with the same |
| CN101120034A (en) * | 2005-02-18 | 2008-02-06 | 旭化成化学株式会社 | Polycarbonate diol |
-
2014
- 2014-03-27 CN CN201410119488.XA patent/CN103897574B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1251116A (en) * | 1997-02-21 | 2000-04-19 | Pp工业俄亥俄公司 | Photochromic polyurethane coating and articles having such coating |
| CN1829780A (en) * | 2003-08-06 | 2006-09-06 | Lg化学株式会社 | Photochromic primer composition having high impact resistance and transparent material coated with the same |
| CN101120034A (en) * | 2005-02-18 | 2008-02-06 | 旭化成化学株式会社 | Polycarbonate diol |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106634533A (en) * | 2016-12-26 | 2017-05-10 | 北京东方雨虹防水技术股份有限公司 | Thermochromatic polyurethane waterproof paint |
| CN106634533B (en) * | 2016-12-26 | 2019-04-16 | 北京东方雨虹防水技术股份有限公司 | A kind of thermochromism polyurethane water-proof paint |
| CN109535888A (en) * | 2018-10-25 | 2019-03-29 | 广州市科涵实业有限责任公司 | A kind of one pack system photochromic coating and preparation method thereof |
| CN110323263A (en) * | 2019-07-10 | 2019-10-11 | 京东方科技集团股份有限公司 | Polaroid, display device |
| CN112708344A (en) * | 2021-01-06 | 2021-04-27 | 光易科技(无锡)有限公司 | Photochromic composition of hyperbranched polyurethane vinyl ether, product and preparation method |
| CN112708344B (en) * | 2021-01-06 | 2022-01-11 | 光易科技(无锡)有限公司 | Photochromic composition of hyperbranched polyurethane vinyl ether, product and preparation method |
| CN114335894A (en) * | 2021-12-21 | 2022-04-12 | 惠州锂威新能源科技有限公司 | Diaphragm with photochromic coating, preparation method thereof and secondary battery |
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