WO2010045797A1 - 具有双变色图文的防伪薄膜及其制备方法 - Google Patents

具有双变色图文的防伪薄膜及其制备方法 Download PDF

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WO2010045797A1
WO2010045797A1 PCT/CN2009/072189 CN2009072189W WO2010045797A1 WO 2010045797 A1 WO2010045797 A1 WO 2010045797A1 CN 2009072189 W CN2009072189 W CN 2009072189W WO 2010045797 A1 WO2010045797 A1 WO 2010045797A1
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film
liquid crystal
exposure
crystal material
photoinitiator
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PCT/CN2009/072189
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English (en)
French (fr)
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徐良衡
董兰新
高芸
张智喜
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上海复旦天臣新技术有限公司
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Priority to JP2011532477A priority Critical patent/JP5565975B2/ja
Priority to EP09821518.9A priority patent/EP2351809B1/en
Priority to US13/125,749 priority patent/US8632849B2/en
Publication of WO2010045797A1 publication Critical patent/WO2010045797A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
    • C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
    • C09K2219/03—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used in the form of films, e.g. films after polymerisation of LC precursor
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24479—Structurally defined web or sheet [e.g., overall dimension, etc.] including variation in thickness

Definitions

  • the patent relates to a security film and a preparation method thereof, and particularly to an anti-counterfeiting film having a double color change pattern and a preparation method thereof.
  • the photochromic effect of the material can be obtained by forming a discontinuous layered structure of the material, and the thin layer obtained by co-extruding alternating metals and ceramic sheets has this effect (Dobrowolski, JA; Ho, RC. and Waldorf. A . Applied Optics, 1989, 28, P14), but this material is expensive and practically inconvenient.
  • cholesteric liquid crystals have certain limitations in application. Since small molecule bile liquid crystals are easy to flow, they must be packaged, sandwiched in a glass box, or made into microcapsules or other structures.
  • the polymerizable cholesteric liquid crystal solution is applied to a substrate film by a transfer roll as described in U.S. Patent No. 6,410,130, and the solvent is removed by drying in a drying tunnel to form a film having a photochromic color or pulverized into a pigment.
  • one drawback of this technique is that the realization of the photochromic pattern is obtained by adding the color-changing pigment obtained by the patent to the binder (or resin) to obtain ink printing, and the concentration of the color-changing pigment is lowered due to the presence of the binder. , the color change effect is not obvious enough, the color is not gorgeous.
  • the preparation method of the anti-counterfeit film with dual color change text of the invention comprises the following steps:
  • the product of the step (1) is locally exposed by an ultraviolet lamp, the exposure time is 5 to 30 seconds, and the exposure energy is 1.5 to 15 mW /cm 2 , so that the liquid crystal material after ultraviolet exposure is polymerized.
  • the structure is fixed, and then dried, and can be placed at a temperature of 80 to 120 for 0.5 to 2.5 minutes, so that the liquid crystal material that has not been exposed to ultraviolet light exhibits a different color from the original, such as green, and the angle is changed to a blue color.
  • the exposure time is 5 to 30 seconds, the exposure energy is 1.5 to 15 m W /cm 2 , and the color is fixed to obtain a security film having a double color image;
  • the polymerizable liquid crystal material containing a chiral structure is a bile phase siloxane liquid crystal, and its chemical structure is as follows:
  • R is the sulfhydryl group of Ci-do
  • Y 1 is a mercapto or alkenyl group containing a mesogenic element
  • Y 2 is an organic group containing at least one polymerizable group and at least one divalent ring group
  • the polymerizable liquid crystal material containing a chiral structure may be a commercially available product, such as a product of Wacker Chemical Co., Ltd., CC3767 or CC3939, and CC3767 and CC393 are cholesteric silicon. Oxygen ⁇ liquid crystal, the difference is that the ratio of the two mesogens in the material is different, that is, the P values of the two are different.
  • Said photoinitiator is selected from the group consisting of benzophenone, benzoyl peroxide, azobisisobutyronitrile, 2-hydroxy-methylphenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone Or one or more of 2-methyl-1-(4-methylthiophenyl)_ 2 morpholinyl _ ⁇ acetone, the weight of which is 2 ⁇ : 10% of the polymerizable liquid crystal material containing a chiral structure ;
  • the substrate film is selected from the group consisting of polycarbonate, polyester or polypropylene, preferably a polyester film, or a substrate film coated with a polyimide-based liquid crystal aligning agent or polyvinyl alcohol;
  • the ultraviolet light source is preferably a 300 ⁇ 2000W mercury xenon lamp, and the intensity at 280 nm to 350 nm is 1.5 to 15 mw/cm;
  • the polymerizable liquid crystal material containing a chiral structure is aligned and has a unique super-helical structure, which can reflect the selective reflection of circularly polarized light, and can selectively reflect light of a specific wavelength, and the macroscopic expression is a photochromic discoloration.
  • the effect that is, when changing the viewing angle, changes from one hue to another.
  • the film obtained by the preparation method of the invention has a double color change picture, and the typical picture is a red-green image when viewed vertically, and after tilting a certain angle, the original red color changes green, green turns blue, The color is obvious, easy to identify, practical and convenient, and easy to promote and apply.
  • Figure 1 shows the structure of a quartz glass cover.
  • Figure 1 is a schematic view showing the structure of a quartz glass cover.
  • the partial exposure of the ultraviolet lamp means that there is a quartz glass cover on the outside of the ultraviolet lamp, and a part of the quartz glass cover is provided with an aluminized layer, which is an opaque area 1.
  • the other part is a non-aluminized transparent area 2, and the transparent area 2 can be designed as In a specific image, the substrate film is subjected to localized partial exposure through the quartz glass cover after coating the polymerizable liquid crystal material, as shown in FIG.
  • the composite film printed with the cover layer pattern may be coated with the substrate film coated with the liquid crystal material, and the UV light is exposed from one side of the composite film, and the light-transmitting portion is UV-cured, and the portion having the cover layer pattern is not Exposure to achieve localized exposure.
  • the polymerizable liquid crystal material containing a chiral structure is a cholesteric silicon germanium liquid crystal, and CC3939 and CC3767 of Wacker Chemical Co., Ltd. can be used.
  • the light transmission part is set to the text "TECHSUN" Position the local exposure for 10 seconds, the exposure energy is 3mw/cm 2 , and then enter the drying tunnel with the set temperature of 105 °C for 60 seconds, then The whole exposure of the 800W mercury xenon lamp was carried out for 10 seconds, and the image with double color change effect was obtained (the text "TECHSUN” was observed vertically in red, the tilt was 45° in green, and the other part was observed in green, tilted at 45°. Blue).
  • the transmission spectrum method was used for the detection, and the results were as follows:
  • the coating film thickness is 12 ⁇
  • the drying tunnel temperature is set to 85 ° C, stay in the drying tunnel for 60 seconds, and covered with the PET composite film printed with black "TECHSUN", from 800W on the side of the PET composite film
  • the mercury xenon lamp was exposed for 10 seconds, the exposure energy was 3 m W /cm 2 , the PET composite film was removed, and the film was placed in a drying tunnel set at 105 ° C for 60 seconds, and then exposed to an 800 W mercury xenon lamp for 10 seconds.
  • a graphic with a double color effect is obtained (the text "TECHSU” is observed vertically in green, and is inclined at 45° to observe blue, while the remaining portion is observed in red, and inclined at 45° in green).
  • the PET composite film was removed, and then the temperature was set to 120 ° C for 60 seconds, and then the 800 W mercury lamp was used for overall exposure. In 10 seconds, the text of the double color change effect was obtained (the text "TECHSUN” was observed as green in a vertical direction, blue in a tilted 45°, and red in a vertical direction and green in a 45° tilt).

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Polarising Elements (AREA)
  • Laminated Bodies (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Liquid Crystal (AREA)
  • Credit Cards Or The Like (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Description

具有双变色图文的防伪薄膜及其制备方法
技术领域
本专利涉及一种防伪薄膜及其制备方法， 具体涉及一种具有双变色图 文的防伪薄膜及其制备方法。
背景技术
随着商品经济的日趋发展， 出现了众多针对各种领域内名优企业品牌 产品的假冒、 仿制， 经济损失严重， 社会危害极大， 使得防伪技术引起了 人们的普遍重视。 能够产生光角变色效果的材料由于易于大众的识别而得 到了迅速发展， 在防伪和装饰材料领域得到了广泛应用。
材料的光角变色效果可以通过形成材料的间歇层状结构而获得， 将交 替的金属和陶瓷片共挤压得到的薄层就具有这种效果 （Dobrowolski, J.A.; Ho, RC. and Waldorf. A., Applied Optics, 1989,28,P14), 但这种材料造价较 高， 实用不便。
此外， 具有光的选择反射性的胆 型液晶在以前被考虑用作光学保密 设施， 如 GB 1387398所披露的技术， 但是小分子的胆 型液晶在应用上却 有一定的局限性。 由于小分子胆 型液晶易于流动， 在应用上必须将它们 封装起来， 夹在玻璃盒中， 或者制成微胶囊或别的结构。 而 US6410130中 提到的将可聚合胆 型液晶溶液通过转移辊涂布于基材膜上， 经烘道除去 溶剂后 UV 固化形成具有光角变色的薄膜， 或将其粉碎制成颜料。 但是， 该技术存在的一个缺陷是光角变色图案的实现是将由该专利得到的变色颜 料添加到连接料 （或树脂） 中制成油墨印刷得到的， 由于连接料的存在降 低了变色颜料的浓度， 使得变色效果不够明显， 颜色不够艳丽。
发明内容 本发明的目的是提供一种具有双变色图文的防伪薄膜及其制备方法， 以克服现有技术存在的上述缺陷。
本发明的具有双变色图文的防伪薄膜的制备方法， 包括如下歩骤：
( 1 ) 将含有手性结构的可聚合液晶材料与光敏引发剂混合， 加热至 80-120 °C , 刮涂于基材膜上， 控制涂膜厚度为 2〜15μπι， 然后烘干， 可置 于 80~120°C温度下 0.5〜2.5分钟， 此时， 垂直观察时呈现一特定的颜色， 如红色， 倾斜一定的角度变为绿色；
(2 ) 然后， 将歩骤 （1 ) 的产物， 采用紫外灯定位局部曝光， 曝光时 间为 5〜30秒钟， 曝光能量为 1.5〜15mW/cm2，使得经过紫外曝光部位的液 晶材料聚合， 结构固定下来， 然后烘干， 可置于 80~120温度下 0.5〜2.5分 钟， 使得未经过紫外曝光的液晶材料呈现与原来不同的颜色， 如绿色， 倾 斜一定的角度变为蓝色， 再通过紫外曝光， 曝光时间为 5〜30秒钟， 曝光 能量为 1.5〜15mW/cm2，将该颜色固定下来，得到具有双变色图文的防伪薄 膜；
所说的含有手性结构的可聚合液晶材料的为胆 相硅氧垸液晶， 其化 学结构通式如下：
Figure imgf000004_0001
其中， R是 Ci—do的垸基；
Y1是含有介晶基元的垸基或链烯基 ·，
Y2是含有至少一个可聚合基团和至少一个二价环基的有机基 团；
P和 q为大于 0小于 1的正数， p+q=l ; m为 3〜10的整数。 含有手性结构的可聚合液晶材料可采用市售的产品， 如采用瓦克化学 公司牌号为 CC3767或 CC3939的产品， CC3767和 CC393均为胆甾相硅 氧垸液晶， 其区别在于： 两者介晶基元在材料中所占的比例不同， 即两者 的 P值不同。
所说的光敏引发剂选自二苯甲酮、 过氧化苯甲酰、 偶氮二异丁腈、 2- 羟基-甲基苯基丙垸 -1-酮、 1-羟基环己基苯基甲酮或 2-甲基 -1-(4-甲硫基苯 基 )_2_吗啉基 _μ丙酮中的一种以上，重量用量为含有手性结构的可聚合液晶 材料的 2〜： 10 % ;
所说的基材膜选自聚碳酸酯、 聚酯或聚丙烯， 优选聚酯膜， 或者是涂 布了聚酰亚胺类液晶取向剂或聚乙烯醇等处理了的基材膜；
紫外光源优选采用 300〜2000W汞氙灯， 280nm〜350nm处的强度为 1.5〜15mw/cm；
含有手性结构的可聚合液晶材料经过排列取向后， 含有一种独特的超 级螺旋结构， 可体现出类似圆偏振光的选择反射性， 可选择性反射特定波 长的光， 宏观表现为光角变色效果， 即当改变观察角度时， 会从一个色相 转变为另一个色相。
采用本发明的方法制备方法得到的薄膜， 具有双变色图文， 比较典型 的图文是垂直观察时呈现红绿图像， 而倾斜一定的角度后， 原来的红色变 色绿色， 绿色变为蓝色， 变色明显， 容易识别， 实用方便， 便于推广应用。 附图说明
图 1为石英玻璃罩结构。
具体实施方式
图 1 为石英玻璃罩结构示意图， 所说的紫外灯定位局部曝光， 是指在 紫外灯的外面有一个石英玻璃罩， 该石英玻璃罩的一部分设有镀铝层， 为 不透光区域 1， 而另一部分则为不镀铝透光区域 2， 透光区域 2可以设计成 特定的图文， 基材膜在涂布可聚合液晶材料后经过此石英玻璃罩实现定位 局部曝光， 如图 1 所示。 亦或将印刷有遮盖层图案的复合膜与涂布液晶材 料的基材膜覆合， 由复合膜的一侧进行 UV曝光， 则透光部位被 UV固化， 而有遮盖层图案的部位未经曝光， 从而实现定位局部曝光。
实施例 1
含有手性结构的可聚合液晶材料为胆 相硅氧垸液晶， 可采用的瓦克 化学公司的 CC3939和 CC3767。
将 7.0克 CC3767和 3.0克 CC3939及 0.4克 2-甲基 -1-(4-甲硫基苯基) -2- 吗啉基 -1-丙酮混合均匀， 加热至 85°C用刮刀涂布于 PET聚酯膜上， 涂膜厚 度为 5μπι， 通过红外烘道， 烘道温度设定为 85°C， 在烘道内停留 60秒钟， 用 800W的汞氙灯， 外套如图 1所示的局部透光的石英玻璃罩， 透光部位设 定为文字" TECHSUN") 定位局部曝光 10秒钟， 曝光能量为 3mw/cm2， 再 进入设定温度为 105°C的烘道停留 60秒钟， 再用 800W的汞氙灯整体曝光 10秒钟，由此得到了双变色效果的图文（文字 "TECHSUN"垂直观察为红色， 倾斜 45°观察为绿色， 而其余部分垂直观察为绿色， 倾斜 45°观察为蓝色）。
采用透射光谱法进行检测， 结果如下:
Figure imgf000006_0001
实施例 2
将 7.0克 CC3767和 3.0克 CC3939及 1.0克 2-甲基 -1-(4-甲硫基苯基) -2- 吗啉基 -1-丙酮混合均匀， 加热至 85°C用刮刀涂布于 PET聚酯膜上， 涂膜厚 度为 12μπι， 通过红外烘道， 烘道温度设定为 85°C， 在烘道内停留 60秒钟， 与印刷有黑色 "TECHSUN"的 PET复合膜覆合，从 PET复合膜一侧用 800W的 汞氙灯曝光 10秒钟， 曝光能量为 3mW/cm2， 揭去 PET复合膜， 再进入设定 温度为 105°C的烘道停留 60秒钟， 再用 800W的汞氙灯整体曝光 10秒钟， 由此得到了双变色效果的图文（文字 "TECHSU "垂直观察为绿色，倾斜 45° 观察为蓝色， 而其余部分垂直观察为红色， 倾斜 45°观察为绿色）。
Figure imgf000007_0001
实施例 3
将 10.0克 CC3767及 0.2克 2-甲基 -1-(4-甲硫基苯基) -2-吗啉基 -1-丙酮混 合均匀， 加热至 85°C用刮刀涂布于 PET聚酯膜上， 涂膜厚度为 8μπι， 通过 红外烘道， 烘道温度设定为 105°C， 在烘道内停留 60秒钟， 与印刷有黑色 "TECHSUN"的 PET复合膜覆合， 从 PET复合膜一侧用 800W的汞氙灯曝光 10秒钟， 曝光能量为 3mw/cm2， 揭去 PET复合膜， 再进入设定温度为 120°C 的烘道停留 60秒钟， 再用 800W的汞氙灯整体曝光 10秒钟， 由此得到了双 变色效果的图文（文字 "TECHSUN"垂直观察为绿色， 倾斜 45°观察为蓝色， 而其余部分垂直观察为红色， 倾斜 45°观察为绿色）。
Figure imgf000007_0002

Claims

权利要求
1. 具有双变色图文的防伪薄膜的制备方法， 其特征在于， 包括如下歩 骤：
( 1 )将含有手性结构的可聚合液晶材料与光敏引发剂混合， 刮涂于基 材膜上， 然后烘干；
(2 ) 然后， 将歩骤 （1 ) 的产物， 采用紫外灯定位局部曝光， 然后烘 干， 再通过紫外曝光， 得到具有双变色图文的防伪薄膜；
所说的含有手性结构的可聚合液晶材料为胆 相硅氧垸液晶。
2. 根据权利要求 1所述的方法， 其特征在于， 所说的光敏引发剂选自 二苯甲酮、 过氧化苯甲酰、 偶氮二异丁腈、 2-羟基-甲基苯基丙垸 -1-酮、 1- 羟基环己基苯基甲酮或 2-甲基 -1-(4-甲硫基苯基) -2-吗啉基 -1-丙酮中的一种 以上。
3. 根据权利要求 2所述的方法， 其特征在于， 光敏引发剂重量用量为 含有手性结构的可聚合液晶材料的 2〜10 %。
4. 根据权利要求 1所述的方法， 其特征在于， 所说的基材膜选自聚碳 酸酯、 聚酯或聚丙烯。
5. 根据权利要求 1所述的方法， 其特征在于， 所说的基材膜是涂布了 聚酰亚胺类液晶取向剂或聚乙烯醇处理了的基材膜。
6. 根据权利要求 1所述的方法， 其特征在于， 将含有手性结构的可聚 合液晶材料与光敏引发剂混合， 加热至 80~120°C， 刮涂于基材膜上。
7. 根据权利要求 6 所述的方法， 其特征在于， 控制涂膜厚度为 2〜
8. 根据权利要求 1所述的方法， 其特征在于， 将歩骤（1 ) 的产物， 采 用紫外灯定位局部曝光， 曝光时间为 5〜30 秒钟， 曝光能量为 1.5〜 15mw/cm2, 然后置于 80~120温度下 0.5〜2.5分钟， 再通过紫外曝光， 曝光 时间为 5〜30秒钟， 曝光能量为 1.5〜15mw/cm2，得到具有双变色图文的防 伪薄膜。
9. 根据权利要求 1~8任一项所述的方法制备的具有双变色图文的防伪
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