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Preparation method of double-pyran thiophene photochromic polymer and color-changing anti-counterfeiting printing ink thereof

An anti-counterfeiting ink and color-changing technology, which is applied in inks, applications, household appliances, etc., can solve the problems of limiting the application range and service life of color-changing compounds, slow color changing speed, poor fatigue resistance, etc., and achieves light-changing ability without weakening. Simple, non-yellowing effect

Active Publication Date: 2016-10-26
山西精华永昌科技有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional photochromic compounds mainly have disadvantages such as low solubility, slow discoloration speed, and poor fatigue resistance, which limit the application range and service life of color-changing compounds

Method used

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  • Preparation method of double-pyran thiophene photochromic polymer and color-changing anti-counterfeiting printing ink thereof
  • Preparation method of double-pyran thiophene photochromic polymer and color-changing anti-counterfeiting printing ink thereof
  • Preparation method of double-pyran thiophene photochromic polymer and color-changing anti-counterfeiting printing ink thereof

Examples

Experimental program
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preparation example Construction

[0042] The preparation of the photochromic dye of the present invention refers to the existing technology (Xiuhong Lu, Qian Dong, Xiaochun Dong, Weili Zhao, Synthesis and sequential photochromism of thiophene-linkedbis-pyrans. Tetrahedron 71 (2015) 4061-4069).

[0043] In Examples 1-4, the bispyranthiophene photochromic dye used was prepared by the following method:

[0044] S1. Under an ice-water bath, add 10mmol thiophene, dichloroethane, and 3-8mmol tin tetrachloride into the reaction kettle in turn, stir evenly, and slowly add 20-22mmol benzoyl chloride or alkoxybenzoyl chloride within 30min , reacted for 48h, rotary steamed and purified;

[0045] S2. Dissolve the product of step S1 in 3-10ml tetrahydrofuran, pass N 2 , under an ice-water bath, add 35-45 mmol of trimethylsilylacetylene and 20-35 mmol of n-butyllithium to react for 8 hours;

[0046] S3. At room temperature, slowly add 30-40 mmol tetrabutylammonium fluoride tetrahydrofuran solution dropwise, react for 20-30 ...

Embodiment 1

[0055] S1. Dissolve 10mmol bispyranothiophene photochromic dye A and 18-22mmol acetyl chloride in 60-80mL nitrobenzene, slowly add 28-32mmol aluminum trichloride dropwise, and react at room temperature for 4-8 hours; Acetyl bis-pyranothiophene photochromic dye;

[0056] S2. Dissolve 8 mmol of the product in step S1 in 25-30 mL of dioxane, add dropwise 0.15-0.2 mmol of sodium hypochlorite dissolved in 15-20 mL of dioxane at 50°C, and react at 70-80°C for 2-3 hours; Purified to obtain the photochromic dye of bispyranothiophene with carboxyl groups;

[0057] S3. Dissolve 5 mmol of the product in step S2 in 20 to 30 mL of dichloromethane, add 5 to 6 mmol of hydroxyethyl methacrylate, 5 to 7 mmol of dicyclohexylcarbodiimide, and 0.2 to 0.6 mmol of catalyst 4-dimethylamino Pyridine, reacted at room temperature for 5-8 hours; purified to obtain bis-pyranothiophene photochromic dye with double bond;

[0058] S4.N 2 Under protection, blend 11.5g of the product of step S3 with 29.5g ...

Embodiment 2

[0062] The bispyranothiophene photochromic dye A described in Example 1 was replaced with the bispyranothiophene photochromic dye B, and the bispyranothiophene photochromic dye with a double bond was prepared according to the method described in S1 to S3 in Example 1 dye;

[0063] S4.N 2 Under protection, blend 5g of the product of step S3 with 36g of butyl acrylate, 8g of methyl methacrylate, 1g of acrylic acid, and 49.8g of tetrahydrofuran, raise the temperature to 50°C, add 0.2g of the initiator azobisisoheptanonitrile, and react for 5h , and the solvent was removed by rotary evaporation to obtain bis-thiopyranophotochromic polymer 2.

[0064] Dissolve the linking resin in xylene, dissolve the bispyranothiophene photochromic polymer 2 in xylene, mix, add UV absorber, hindered amine stabilizer and antioxidant dissolved in butyl acetate, and stir After uniformity, the photochromic anti-counterfeiting ink is obtained. See Table 1 for specific models and dosages.

[0065] T...

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Abstract

The invention discloses a preparation method of a double-pyran thiophene photochromic polymer and color-changing anti-counterfeiting printing ink thereof. The preparation method of the double-pyran thiophene photochromic polymer includes the following steps that a double-pyran thiophene photochromic dye is subjected to acetylation to introduce acetyl, then a carboxylation reaction is further conducted, and an intermediate with carboxyl is obtained; the intermediate and hydroxyl acrylate matter are subjected to an esterification reaction to introduce double bonds, then copolymerization with acrylic monomers is further conducted, and the double-pyran thiophene photochromic polymer is prepared. The color-changing anti-counterfeiting printing ink prepared based on the double-pyran thiophene photochromic polymer can be changed to be yellow rapidly and then gradually changed to be blue or purple under illumination of sunlight or ultraviolet light, and after illumination is removed, the printing ink recovers to be colorless. The anti-counterfeiting performance of the prepared color-changing printing ink is improved, authenticity can be recognized without any instrument, and universality of anti-counterfeiting means can be improved.

Description

technical field [0001] The invention relates to a preparation method of bispyranthiophene photochromic polymer and color-changing anti-counterfeit ink, which can be used for anti-counterfeit products and packaging printing, and belongs to the product printing industry. technical background [0002] Counterfeit and shoddy goods and counterfeit tickets are extremely harmful, not only infringing on the legitimate interests of businesses, destroying corporate image and market order, but also damaging the economic interests of consumers, and even their lives, seriously endangering social harmony and stability. In order to protect the rights and interests of consumers and the economic benefits of businesses, various anti-counterfeiting methods and products have emerged as the times require. In recent years, new types of anti-counterfeiting inks have been emerging. The use of a single anti-counterfeiting ink or a combination of multiple anti-counterfeiting inks has been widely used...

Claims

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Application Information

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IPC IPC(8): C08F220/18C08F222/24C08F220/14C08F220/06C09D11/50C09D11/037C09D11/107C09D11/104C09D11/103C09D11/102
CPCC09D11/037C09D11/102C09D11/103C09D11/104C09D11/107C09D11/50C08F220/18C08F220/1804C08F222/245C08F220/1812C08F220/1802C08F220/1808C08F220/14C08F220/06
Inventor 何国雄伍雪芬
Owner 山西精华永昌科技有限公司
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