CN103897574B - 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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- CN103897574B CN103897574B CN201410119488.XA CN201410119488A CN103897574B CN 103897574 B CN103897574 B CN 103897574B CN 201410119488 A CN201410119488 A CN 201410119488A CN 103897574 B CN103897574 B CN 103897574B
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- 238000000576 coating method Methods 0.000 title claims abstract description 53
- 239000011248 coating agent Substances 0.000 title claims abstract description 52
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 20
- 239000000758 substrate Substances 0.000 claims abstract description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000016 photochemical curing Methods 0.000 claims abstract description 8
- 238000001029 thermal curing Methods 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 12
- 150000003077 polyols Chemical class 0.000 claims description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000000326 ultraviolet stabilizing agent Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229920013639 polyalphaolefin Polymers 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 8
- 229920002554 vinyl polymer Polymers 0.000 abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- -1 acryl Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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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 invention relates to an optical material, in particular to a photochromic composition coating, a photochromic composition coated product and a preparation method of the photochromic composition coated product.
Background
In the conventional photochromic plastic product, a photochromic factor (photochromic dye) is added to the photochromic plastic product, or the photochromic factor is added by a surface absorption swelling method. Such photochromic plastic articles are susceptible to discoloration (staining) in sunlight (in the presence of ultraviolet light) and, upon leaving the sunlight, such photochromic plastic articles recover their original color (fading). However, current photochromic plastic articles suffer from the following disadvantages: the surface of the photochromic plastic product is easy to generate bubbles or fog, or the surface of the photochromic plastic product is not high in hardness and easy to wear.
Disclosure of Invention
The purpose of the invention is as follows: the first object of the present invention is to provide a photochromic composition coating layer which does not generate bubbles, has high hardness and is abrasion-resistant;
it is a second object of the present invention to provide a photochromic composition coated article;
the third object of the present invention is to provide a method for preparing the photochromic composition-coated article.
The technical scheme is as follows: the photochromic composition coating is characterized by comprising the following components: at least one photochromic amount of photochromic factor, polymeric polyol with the number average molecular weight (Mn) of 200-2000, at least one substance containing isocyanate groups with the number average molecular weight (Mn) of 150-300, at least one substance containing vinyl groups and auxiliary materials, wherein the polymeric polyol, the substance containing isocyanate groups and the substance containing vinyl groups contain at least one of carbonate, aromatic or aliphatic in the main chain.
Wherein the polymeric polyol is at least one of PAO and PO, PCDO; the substance containing the isocyanate group is at least one of IPDI, HDI, H12MDI, TDI and MDI; the vinyl-containing substance is polymethyl methacrylate; the auxiliary materials are solvent, initiator, catalyst, ultraviolet stabilizer and surfactant.
The components are prepared according to the following weight ratio:
the PAO is polymerized from monomers having the general formula:
wherein R1 is H, CH3, OH or SH, R2 is H, CH3, OH or SH, R3 is H, CH3, C2H5, OH or SH, and R4 is C5H9, OH or SH.
The PAO is prepared by the following reaction:
wherein the reaction temperature is 90-110 ℃, the reaction time is 3.8-4.2h, and an initiator is used in the reaction process.
The reactants are prepared according to the following weight ratio:
the photochromic composition coated product comprises a substrate and a photochromic composition coating coated on the substrate.
Wherein, the matrix is a white sheet, a dyed sheet or a polaroid.
The preparation method of the photochromic composition coating product comprises the steps of firstly coating the photochromic composition coating on a substrate, and then fixing the coating by adopting a thermal curing and photocuring mode.
Wherein the photocuring time is more than 1h, and the thermocuring time is 1 min.
Has the advantages that: compared with the prior art, the invention has the following remarkable advantages: 1. the photochromic composition coating does not generate bubbles after being coated on a substrate, and has higher hardness and is not easy to wear; 2. the coating of the invention can be used for common lenses with refractive indexes of 1.499,1.56,1.60,1.67,1.74 and the like, as well as color changing sheets and polarizers; 3. the photochromic composition coating product has long service life and almost no damage after being used for more than one year; 4. the preparation method of the coating product of the invention adopts simultaneous thermal curing and photocuring, and has excellent curing effect.
The specific implementation mode is as follows:
the technical solution of the present invention is further explained below.
The photochromic composition coating (hereinafter referred to as coating) is prepared by adding photochromic factors into corresponding dissolving solution, wherein the main component of the dissolving solution is polyurethane or a substance (preferably acrylic) containing vinyl (with vinyl group), and one of the two is selected in the prior art. The two solutions have advantages and disadvantages, wherein the physical properties of polyurethane are easy to adjust, but the synthesis conditions are harsh, such as long reaction time; acryl is easily synthesized and has a short reaction time as compared with polyurethane, but it is difficult to control physical properties thereof. The invention mixes the two solutions (polyurethane and acrylic) to obtain the composition with required physical properties, and the reaction is easy to carry out and takes short time.
The polyurethanes of the invention are synthesized by polymerizing polyols (with OH groups) and isocyanate-containing substances (with NCO groups). Wherein, the number average molecular weight (Mn) of the polymer polyol screened by the invention is 200-2000, preferably 200-1000 after a plurality of tests, which can ensure that the coating does not fog after being coated and has better hardness and transparency, and the number average molecular weight is determined by polystyrene chromatography (the same below); meanwhile, the polydispersity index of the polymeric polyol is below 2.0, so that the surface of the coating is ensured to be uniform. The polymeric polyol is at least one of PAO, PO and PCDO, and the prepared coating solution has good hardness and is beneficial to the dissolution of photochromic factors.
PO is a polyol, for example a carbonate polyol (Mn) from Aldrich, having a number average molecular weight (Mn) of 1000;
PCDO (polycarbonatediol) is a polycarbonate diol, also available from Aldrich, having a number average molecular weight (Mn) of 800;
PAO（Polyacrylol）
structural formula (xvi):
the molecular formula is as follows: C14H24O 5; number average molecular weight (Mn): 273.
the PAO of the present invention is polymerized from the following monomers:
r1: H, CH3, OH or SH,
r2: H, CH3, OH or SH,
r3: H, CH3, C2H5, OH or SH,
R4C 5H9, OH or SH.
The PAO is prepared by the following reaction:
wherein the reaction temperature is 90-110 ℃, and the preferable temperature is 100 ℃; the reaction time is 3.8-4.2h, preferably 4h, and initiator V-65 (azobisisoheptonitrile) is used in the reaction process.
The reactant ratios and reaction conditions are specifically as follows:
TABLE 1
The number average molecular weight (Mn) of the substance containing isocyanate groups is 150-300, and specifically at least one of IPDI, HDI, H12MDI, TDI and MDI.
Wherein,
IPDI (isophorone diisocyanate), isophorone diisocyanate, C12H18N2O2, number average molecular weight (Mn) 222.3, available from Aldrich.
Having a molecular formula of
HDI (1, 6-hexamethylene diisocyanate), 1,6-hexamethylene diisocyanate, C8H12N2O2, number average molecular weight (Mn) 168.19, available from Aldrich.
Having a molecular formula of
TDI (tolumen diisocyante), toluene diisocyanate, C9H6N2O2, number average molecular weight (Mn) 174.2, available from Aldrich.
Having a molecular formula of
In addition, H12MDI and MDI are also available from Aldrich.
The vinyl group-containing substance according to the present invention is preferably acrylic (polymethyl methacrylate).
The solvent used in the present invention is NMP (n-methyl-pyrollidone), Toluene (Toluene), methanol (methanol) or cyclohexoxane (cyclohexanone), which are all available from Aldrich. Among them, through a plurality of experiments, NMP (Chinese name n-methylene pyrrolidone, C5H9NCO5H, number average molecular weight (Mn) of 99.13) is found to have the best solubility, so that polyurethane and acrylic are organically combined together.
Other auxiliary materials used in the invention:
initiator, V-65 (azobisisoheptonitrile), available from Wakco chemicals (Wakco Chemicals);
catalyst, available from sankyo organic chemicals-Stann BDC (dibutyltin dichloride);
ultraviolet light stabilizers (UV stabilizers) available from seesorb 709;
surfactant, available from BYK company-BYK 301.
The photochromic factors, otherwise known as photochromic dyes, used in the present invention are available from the vivimed company,
for example, it may be:
1. spirooxazines of the formula
2. Spiropyrans of the formula
3. Chromenes (benzopyrans) of the formula
The weight ratio of the raw materials for preparing the coating is shown in the following table 2:
TABLE 2
The coating is prepared by adopting a conventional technical means, namely all the raw materials in the table 2 are poured into a glass reactor, mixed and stirred, and various parameters are controlled to react.
The coating prepared by the method has the number average molecular weight of 500-50000, preferably 800-15000 and the glass transition temperature of more than 5 ℃.
Coating the prepared coating on a substrate, and specifically comprises the following steps: dropping 1-2g of coating solution (or named as photochromic hardening liquid) on the surface of the lens rotating at the speed of 400-500rpm, after dropping 5-10 seconds, rotating at the speed of 800-2000rpm for 10-20 seconds, carrying out thermal curing for 0.5-1.5min (preferably 1 min) and photocuring for more than 1h and less than 2h, and finally obtaining the photochromic composition coating product (hereinafter named as coating product).
The thermal curing is to evaporate the solvent by physical heating to harden the coating; the photo-curing is to use ultraviolet light to initiate the substances in the coating to generate cross-linking reaction so as to form new chemical bonds to realize the hardening of the coating, so that the two methods have advantages and disadvantages respectively. The existing coating system can only adopt one curing mode; the invention can simultaneously adopt the two curing modes to uniformly coat the coating on the substrate, and the coating has better hardness after curing, is not soft or too hard, and has lower energy consumption, higher curing speed and easy realization.
The matrix is a white sheet, a dyed sheet or a polaroid, and the refractive index of the matrix is between 1.499 and 1.74; the organic or inorganic polymeric substrate may also be selected from thermosetting and thermoplastic materials.
The coated articles obtained from 12 groups of examples in table 1 were tested as follows, and the test results are shown in table 3:
1. transmittance before and after discoloration of the coated article was measured
Equipment: simitsu UV spectrometer;
color-changing light source: 350nm, temperature 24 ℃, time 15 seconds, transmittance measurement wavelength: 490 nm.
2. Detection of bubbles and blue fog in coated articles
In table 3, X indicates none, 0 indicates presence, and Δ indicates a little.
The coatings obtained in examples 5, 6, 7, 9, 10, 11, 12 did not generate bubbles and blue haze due to the addition of polyurethane and acryl to the solution.
3. Measurement of surface hardness
Equipment: fisherscope HCV model H-100 from Fisher Technology Inc., Inc
The method comprises the following steps: the surface of the lens is 10N/mm2After the lens is kept under the pressure of (1) for 15 seconds, the hardness of the lens is measured at the depth of 2 mu m, and the average value of data obtained after 2-5 times of measurement is taken for each lens.
As can be seen from Table 3, the coated articles obtained in examples 6, 9, 10, 11 and 12 had high surface hardness, and the coated article obtained in example 7 had high surface hardness.
TABLE 3
Claims (7)
1. A photochromic composition coating comprising the following components: at least one photochromic amount of photochromic factor, polymeric polyol with the number average molecular weight of 200-1000, at least one isocyanate group-containing substance with the number average molecular weight of 150-300, polymethyl methacrylate and auxiliary materials;
wherein the polymeric polyol is at least one of PAO and polyol and polycarbonate diol, the substance containing isocyanate group is at least one of IPDI, HDI and TDI, and the auxiliary materials are solvent, initiator, catalyst, ultraviolet stabilizer and surfactant;
the PAO is polymerized from monomers having the general formula:
wherein R1 is H, CH3OH or SH, R2 is H, CH3OH or SH, R3 is H, CH3、C2H5OH or SH, R4 is C5H9OH or SH;
the weight ratio of each component is as follows:
2. the photochromic composition coating of claim 1, wherein the PAO is prepared by the reaction of:
wherein the reaction temperature is 90-110 ℃, the reaction time is 3.8-4.2h, and an initiator of azobisisoheptonitrile is used in the reaction process.
3. The photochromic composition coating of claim 2, wherein the reactants are present in the following proportions by weight:
4. a photochromic composition coated article characterized by: comprising a substrate and a coating of a photochromic composition according to any one of claims 1 to 3 applied on the substrate.
5. The coated article of photochromic composition of claim 4 wherein: the matrix is a white sheet, a dyed sheet or a polaroid.
6. A method of making an article coated with a photochromic composition, comprising: a coating of a photochromic composition according to any one of claims 1 to 3 is first applied to a substrate and then the coating is fixed by both thermal and photo-curing.
7. A method of making an article coated with a photochromic composition according to claim 6 wherein: the photocuring time is 1-2h, and the thermocuring time is 0.5-1.5 min.
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| 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 |
| 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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| CN1251116A (en) * | 1997-02-21 | 2000-04-19 | Pp工业俄亥俄公司 | Photochromic polyurethane coating and articles having such coating |
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| JP5068159B2 (en) * | 2005-02-18 | 2012-11-07 | 旭化成ケミカルズ株式会社 | Polycarbonate diol |
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| CN1251116A (en) * | 1997-02-21 | 2000-04-19 | Pp工业俄亥俄公司 | Photochromic polyurethane coating and articles having such coating |
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