CN1039649C - Photochromic anti-counterfeiting printing ink and manufacturing method thereof - Google Patents
Photochromic anti-counterfeiting printing ink and manufacturing method thereof Download PDFInfo
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- CN1039649C CN1039649C CN 93106107 CN93106107A CN1039649C CN 1039649 C CN1039649 C CN 1039649C CN 93106107 CN93106107 CN 93106107 CN 93106107 A CN93106107 A CN 93106107A CN 1039649 C CN1039649 C CN 1039649C
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- Prior art keywords
- ink
- printing
- photochromic
- low
- forging
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000007639 printing Methods 0.000 title abstract description 22
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920001400 block copolymer Polymers 0.000 claims abstract 2
- 238000002844 melting Methods 0.000 claims description 12
- 238000005242 forging Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical group C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 16
- 238000000034 method Methods 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 abstract description 8
- 239000011347 resin Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 3
- 230000002441 reversible effect Effects 0.000 abstract description 2
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- TZNCLYJRGCYJHE-UHFFFAOYSA-N benzene butane Chemical compound CCCC.CCCC.C1=CC=CC=C1.C1=CC=CC=C1 TZNCLYJRGCYJHE-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- -1 4Be hydrogen Chemical class 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Chemical class CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical group CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical class CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001219 Polysorbate 40 Polymers 0.000 description 1
- NWGKJDSIEKMTRX-MDZDMXLPSA-N Sorbitan oleate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(O)C1OCC(O)C1O NWGKJDSIEKMTRX-MDZDMXLPSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229940101027 polysorbate 40 Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
本发明公开了一种光致变色防伪印刷油墨及其制作方法，本发明的光致变色防伪油墨主要包括螺吲哚啉萘并嗪类光致变色染料、苯丁嵌段共聚树脂、硫代双酚型抗氧剂以及其它辅助成分，其中螺吲哚啉萘并嗪类染料的化学结构式为：
本发明适用于名优商品商标及重要票据证件的防伪标记印刷。本发明在紫外线或太阳光的照射下可使颜色发生改变(无色-蓝色)，具有变色速度快，变色过程可逆，使用寿命长，印刷效果好等特点。
The invention discloses a photochromic anti-counterfeit printing ink and a production method thereof. The photochromic anti-counterfeit ink of the invention mainly comprises spiroindoline naphthoazine photochromic dyes, benzene butane block copolymer resin, thio Bisphenol type antioxidant and other auxiliary components, wherein the chemical structural formula of spiroindoline naphthoazine dyes is:
The present invention is suitable for the anti-counterfeiting mark printing of famous commodity trademarks and important bills and certificates. The invention can change the color (colorless-blue) under the irradiation of ultraviolet light or sunlight, and has the characteristics of fast color changing speed, reversible color changing process, long service life, good printing effect and the like.
Description
The present invention relates to a kind of anti-counterfeit printing material and manufacture method thereof, particularly a kind of photochromism anti-forging printing-ink and manufacture method thereof.
Photochromic material is that a kind of material indoline spiro-pyrans class that can change color under UV-light or other radiation exposure rapidly is the photochromic compound of fully studying, and such material is very limited on the purposes owing to the resistance to fatigue deficiency.The Luo oxazine is another kind of photochromic organism.Recently studies show that this type organic has superior chemical stability and resistance to fatigue than spiro-pyrans, so application potential is very big.Several patents (day disclosure special permission communique 87-172,075/88-196,673/88-305,181 are arranged; 90-20,576; 91-81,378) relate to and utilize the Luo oxazine to make pen or garden pearl board pen ink, or be used for the heat transfer printing of textiles, when being used for the printing of paper, because the influence of factors such as viscosity, flowability, meeting generation inadaptability photochromic compound more or less is used to make the anti-counterfeit printing material also report (EP279,600; WO88-01,288; CN1,044,860A), but used dyestuff is a fulgides, preparation process is many, processed complex, printing is still needed special light sources could variable color.
The purpose of this invention is to provide a kind of photochromism anti-forging printing-ink and manufacture method thereof, can overcome the deficiencies in the prior art part, make not only changeable colour under ultraviolet ray or other radiation exposure of printed pattern, and under common sunlight also changeable colour.
Implementation procedure of the present invention:
1, photochromism anti-forging printing-ink provided by the invention mainly is made up of photochromic dyes, low-melting ink vehicle and ancillary component thereof.
1. photochromic dyes of the present invention is the key component of anti-counterfeit printing printing ink, and it belongs to spiral shell indoline Nai Bing oxazine compounds, and its chemical structural formula is:
R wherein
1Be C
1-C
18Alkyl, aralkyl ， oxazine alkyl; R
2, R
3Be methyl; R
4Be hydrogen, methyl or methoxy; R
5Be hydrogen or ethoxycarbonyl; R
6Be hydrogen hydroxyl, chlorine or bromine.Such dyestuff is low-melting white or faint yellow solid, to light, heat, air-stable, but weak acid resistant or weakly alkaline environment.Its solution changes blueness or bluish voilet rapidly under UV-light or direct sunlight, when removing ultraviolet source or breaking away from direct sunlight, restore to the original state again, and above variable color process can be carried out repeatedly, does not lose efficacy for a long time.
2. low-melting ink vehicle of the present invention is the main component of anti-counterfeit printing printing ink, and it belongs to polyolefin resin, as if the multipolymer of polyethylene, polypropylene, polystyrene and vinylbenzene and divinyl.For adapting to requirement of the present invention, several resins can be used with certain proportioning sometimes.Wherein as low-melting ink vehicle of the present invention best be styrene-butadiene block copolymer, this resin appearance colorless is transparent, good film-forming property is good with above-mentioned dyestuff intermiscibility.In order to make anti-forgery ink, these resins need to be dissolved earlier as low-melting ink vehicle.Solvent commonly used has aromatic hydrocarbons, as benzene,toluene,xylene or chlorobenzene; The ester class is as ethyl acetate, butylacetate, pentyl acetate or phthalic acid ester class; Also have paraffin hydro carbons, ethers and ketone in addition.All be to form mixed solvent as a rule, to satisfy the requirement of solvability and volatility coupling with several organism.
3. auxiliary composition of the present invention has tensio-active agent, photostabilizer and filler etc.Tensio-active agent commonly used is a non-ionic type, as sorbester p17, polysorbate40, peregal 0 etc.; Photostabilizer is thiobisphenol and nickel complex thereof, steric hindrance amine; Filler is the vitriol of calcium, magnesium or the oxide compound of carbonate and some metal etc.
2, in manufacture craft of the present invention, at first be that dyestuff and photostabilizer are mixed with dissolved low-melting ink vehicle with above-mentioned solvent solution-forming, add other ancillary component again and process.Dye dosage is the 0.1-1.0% of low-melting ink vehicle weight, and the consumption of tensio-active agent and photostabilizer and dyestuff quite or slightly lack in the ancillary component, and the add-on of filler requires to decide according to the viscosity of printing ink.Each ancillary component should be even with dyestuff, low-melting ink vehicle thorough mixing, preferably grinds on three-roller or ball mill, so far can obtain photochromism anti-forging printing-ink of the present invention.
Anti-forgery ink provided by the invention is applicable to the printing of various stocks, and as the enamelled paper of different size, newsprinting paper, gelatine printing paper, and polyethylene film and textiles etc. are most convenient with the screen printing mode.Be mainly used in trade mark, security and vital document false proof.When differentiating the true and false of these printed matters, as long as the pattern secret mark that will utilize the present invention to print places under common sunlight or the UV-light, as rapid generation variable color, very fast again recovery when leaving illumination then is a genuine piece, then is counterfeit as above-mentioned phenomenon not occurring.
Advantage of the present invention is: 1. use the pattern secret mark of ink printing of the present invention not only under specific light source such as UV-light, can develop the color, and under sunlight also changeable colour; 2. its variable color process is a reversible, and variable color speed is fast, long service life, and printed matter can be preserved more than 1 year; 3. the fastness of printed matter, sharpness etc. all can make the user satisfied; 4. starting material required for the present invention are easy to get, and the photochromic dyes manufacture method is simple, and the printing ink manufacturing is also more convenient.
The invention will be further described below by example:
Example 1, with 10 parts of benzene fourth block resin＜research institute of Lan Hua company products〉be dissolved in 20 parts of mixed solvents (being lower than 250 ℃ ink oil 8 by boiling point, dimethylbenzene 6,1 part of composition of diethyl phthalate 5 and paraffin wax), obtain water white transparency heavy-gravity low-melting ink vehicle (A), with dyestuff SP-0-5 (R among the formula @
1-4Be CH
3-, R
5-6Be H), photostabilizer (thiobisphenol type) and peregal 0 each portion are dissolved in the suitable N-BUTYL ACETATE jointly, obtain the transparent liquid of oyster (B).To fully grind below 30 ℃ in A and B and 5 parts of Place grinding machines of light calcium carbonate, get white uniform jelly, anti-forgery ink promptly of the present invention.The pattern secret mark that obtains with silk screen printing is difficult for differentiating, but when placing under ultraviolet lamp or the sunlight, just demonstrates the blue marking of analysing clearly immediately.Leave light source, color disappears in can be in several seconds.Printing was preserved under usual condition more than 1 year, and its painted and colour killing performance does not have considerable change.
Example 2, not existing together with example 1 is that dyestuff is BSP-0 (R in the formula
2-3Be CH
3-, R
4-6Be H, R
1Wei the oxazine butyl, consumption is 0.5% of an amount of resin, and with N-BUTYL ACETATE/dimethylbenzene (1: 1) dissolving with preparation B, the performance of gained printing ink and printing is consistent with example 1.
Example 3, with example 1 difference be the resin polystyrene, dyestuff is with SP-0-16 (R among the formula @
1=C
16H
33, R
2-3=CH
3, R
4-6=H), dye dosage is 1% of a resin.Gained printing ink is consistent with example 1 with the printing performance
Claims (4)
1, a kind of photochromism anti-forging printing-ink comprises:
A, photochromic compound, structural formula is:
R in the formula
1Be methyl, sec.-propyl, C
16H
33, aralkyl Huo oxazine butyl, R
2, R
3Be CH
3, R
4Be methyl or methoxy, R
5Be ethoxycarbonyl, R
6Be OH, Cl or Br.
B, polyolefine low-melting ink vehicle, and its nickel complex photostabilizer of thiobisphenol.
2, the printing-ink of photochromism anti-forging as claimed in claim 1 wherein also comprises nonionogenic tenside, solvent and filler.
3, photochromism anti-forging printing-ink as claimed in claim 1 or 2, wherein low-melting ink vehicle is vinylbenzene-butadiene block copolymer.
4, a kind of preparation method of photochromism anti-forging printing-ink, comprise: at first low-melting ink vehicle is dissolved with mixing solutions, with solvent photochromic compound and photostabilizer are dissolved again, then these two kinds of components are mixed, add tensio-active agent and filler again, and put into three-roller or grinding in ball grinder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93106107 CN1039649C (en) | 1993-05-22 | 1993-05-22 | Photochromic anti-counterfeiting printing ink and manufacturing method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93106107 CN1039649C (en) | 1993-05-22 | 1993-05-22 | Photochromic anti-counterfeiting printing ink and manufacturing method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1095734A CN1095734A (en) | 1994-11-30 |
| CN1039649C true CN1039649C (en) | 1998-09-02 |
Family
ID=4986073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 93106107 Expired - Fee Related CN1039649C (en) | 1993-05-22 | 1993-05-22 | Photochromic anti-counterfeiting printing ink and manufacturing method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1039649C (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1064046C (en) * | 1997-11-12 | 2001-04-04 | 南开大学戈德防伪技术公司 | Photochromic spiro-compound and its preparation |
| JP3732469B2 (en) * | 2002-09-04 | 2006-01-05 | 独立行政法人産業技術総合研究所 | Optical recording medium, manufacturing method thereof, and optical recording method |
| JP4174393B2 (en) * | 2002-10-30 | 2008-10-29 | パイロットインキ株式会社 | Tactile color memory photochromic toy |
| CN103911877B (en) * | 2014-04-17 | 2016-01-13 | 傅科杰 | A kind of colour-changing agent for weaving face fabric |
| CN106046241B (en) * | 2016-06-01 | 2018-06-08 | 山西精华永昌科技有限公司 | A kind of preparation method of double pyrans thiophene photochromic polymers and its color varying counterfeit-proof ink |
| CN110698923A (en) * | 2019-07-12 | 2020-01-17 | 湖北中北工贸有限责任公司 | Optically variable ink |
| CN112208237A (en) * | 2020-10-14 | 2021-01-12 | 深圳市深龙杰科技有限公司 | Method for printing multicolor pattern by adopting photochromic principle |
| CN114561124B (en) * | 2022-04-11 | 2023-01-17 | 辽宁大学 | Anti-counterfeiting ink with controllable color development time and anti-counterfeiting printed matter containing it |
-
1993
- 1993-05-22 CN CN 93106107 patent/CN1039649C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1095734A (en) | 1994-11-30 |
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