CN103044946A - Fluorescent pigment - Google Patents
Fluorescent pigment Download PDFInfo
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- CN103044946A CN103044946A CN2012102073864A CN201210207386A CN103044946A CN 103044946 A CN103044946 A CN 103044946A CN 2012102073864 A CN2012102073864 A CN 2012102073864A CN 201210207386 A CN201210207386 A CN 201210207386A CN 103044946 A CN103044946 A CN 103044946A
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- phenyl
- visibility pigment
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Abstract
The invention provides a fluorescent pigment which is expressed by the following molecular structural formula, wherein A is oxygen or secondary amine, B is sulfonyl or carbonyl, and R is phenyl or phenyl with a substituent group. In the structural formula of the fluorescent pigment, sixth and seventh substitution positions respectively adopt methoxyl to carry out substitution, fourth and fifth substitution positions of a phenyl substituent of the fluorescent pigment also adopt the methoxyl to carry out substitution, and H or halogen which is usually adopted on the substitution positions in the prior art is replaced by the methoxyl which is used as a substituent. The fluorescent pigment has the advantages of excellent organic solvent resistance, high melting point, strong luminescent intensity and good light resistance.
Description
Technical field
The present invention relates to a kind of high-visibility pigment, relate in particular to the high-visibility pigment that a kind of fusing point is high, organic solvent resistance is strong, belong to the pigment preparing technical field.
Background technology
High-visibility pigment function of dominant luminous pigment, be when with UV-light or radiation of visible light high-visibility pigment with the difference of general pigment, short wavelength's hertzian wave in ultraviolet or the visible light wave range is absorbed by high-visibility pigment, afterwards, discharges with the electromagnetic form of long wavelength.Long wavelength's hertzian wave drops in the visible-range usually, and itself and conventional optical superposition of reflecting show dazzling fluorescence color; And after light stopped irradiation, luminescence phenomenon namely disappeared, and therefore was called high-visibility pigment.
Benzoxazinone and quinazolinone all belong to high-visibility pigment, and be on the books in the prior art.The benzoxazinone high-visibility pigment is by anthranilic acid or with substituent anthranilic acid and benzene sulfonyl chloride, with substituent benzene sulfonyl chloride, Benzoyl chloride or with substituent Benzoyl chloride, in organic solvent, prepare through polycondensation.The quinazolinone high-visibility pigment is by benzoxazinone and ammoniacal liquor or ammonia, in the water miscible organic solvent of inertia, and in the presence of alkali metal hydroxide, further obtains after the reaction.The quinazolinone that benzoxazinone continues and ammonia react prepares with fluorescence property also has fluorescence property.
In the prior art, the fusing point of benzoxazinone high-visibility pigment generally all is lower than 240 ℃, and organic solvent resistance is relatively poor.And the fusing point that is further reacted the quinazolinone of generation by benzoxazinone generally can be higher than 60 ~ 90 ℃ of the fusing points of benzoxazinone, but the performance of its organic solvent-resistant is also relatively poor.For example, american documentation literature US3740402A discloses fluorescent substance of a kind of quinazolinone and its preparation method and application.In this patent documentation, quinazolinone is by benzoxazinone and ammoniacal liquor, in methylcyclohexane, and in the presence of sodium hydroxide, prepares through reaction.Wherein, the structural formula of benzoxazinone as shown in Equation 1, the structural formula of quinazolinone is as shown in Equation 2.In this technology, quinazolinone under the UV rayed, can send fluorescence at the visible region of 500 ~ 540nm in the presence of solid-state form.But, the fusing point of benzoxazinone only is 170 ~ 223 ℃ in this technology, and the fusing point of the quinazolinone that is prepared by its reaction is 231 ~ 318 ℃, namely the fusing point of benzoxazinone is lower, only up to 223 ℃, can limit like this benzoxazinone under hot conditions, especially prepare application in the anti-false fiber at melt-spinning, the temperature that melt-spinning prepares general requirement high-visibility pigment in the anti-false fiber is higher than 250 ℃.In addition, also all there are the relatively poor problem of organic solvent resistance in above-mentioned benzoxazinone and quinazolinone.
In formula 1 and formula 2, described R is the alkyl of hydrogen, 1 ~ 4 carbon atom or the alkoxyl group of 1 ~ 4 carbon atom; Described R
1And R
2Be the alkyl of hydrogen, 1 ~ 4 carbon atom, the alkoxy or halogen of 1 ~ 4 carbon atom; Described A is alkylene, phenylene or the naphthylidene of 1 ~ 18 carbon atom.
Those skilled in the art are striving to find a kind of high-visibility pigment always, when this high-visibility pigment is benzoxazinone, its fusing point is higher than 260 ℃, and when this benzoxazinone further reacts the generation quinazolinone, it has higher fusing point, and benzoxazinone or quinazolinone also all have stronger organic solvent resistance, especially have the performance of the organic solvents such as excellent anti-ethyl acetate, acetone, toluene, but the high-visibility pigment of always failing to obtain having this performance in the prior art.
Summary of the invention
Technical problem to be solved by this invention be in the prior art benzoxazinone fluorescent material and by its further quinazolinone fluorescent material of generating of reaction all have the poor problem of organic solvent resistance, and also there is low-melting problem in the benzoxazinone fluorescent material, and then provides a kind of and have fusing point and be higher than 260 ℃, high-visibility pigment that organic solvent resistance is strong.
In order to solve the problems of the technologies described above, the invention provides a kind of high-visibility pigment that represents with following molecular formula:
Wherein: A be oxygen (-O-) or secondary amine (
), B be alkylsulfonyl (
) or carbonyl (
), R be phenyl (
) or with substituent phenyl (
Or
Or
).
Described is phenyl with para-orienting group with substituent phenyl.
Described phenyl with para-orienting group is 4-chloro-phenyl-, 4-aminomethyl phenyl or 4-fluorophenyl.
Described A is that oxygen, B are alkylsulfonyl, and R is the 4-chloro-phenyl-.
The wavelength of fluorescence that described high-visibility pigment sends is 450 ~ 560nm.
The fusing point of described high-visibility pigment is 260 ~ 350 ℃.
The solubleness of described high-visibility pigment in organic solvent is less than 1wt%.
Described organic solvent is acetone, ethyl acetate or butanone.
Described high-visibility pigment is used for the purposes of melt-spinning fiber, coloured or colourless anti-forgery ink.
The present invention compared with prior art has following advantage:
(1) high-visibility pigment of the present invention, in the structural formula of described high-visibility pigment, adopt respectively methoxyl group to replace on the 6th and the 7th replacement position, the the 4th and the 5th of phenyl in the structural formula of described high-visibility pigment replaces on the position and also adopts methoxyl group to replace, and has replaced in the prior art at the described normal H that adopts or the halogen of replacing on the position as substituent situation.Has its molecular volume of high-visibility pigment of structure of the present invention greater than the molecular volume of this type of high-visibility pigment in the routine techniques, and the variation of molecular structure is so that high-visibility pigment of the present invention has excellent organic solvent resistance and the high performance of fusing point, it is at organic solvent, especially in the organic solvents such as ethyl acetate, acetone, toluene, the solubleness of described high-visibility pigment is all less than 1wt%; When A was O in the structural formula of described high-visibility pigment, its fusing point was higher than 260 ℃, and when A was secondary amine, its fusing point was higher than 340 ℃.In addition, the variation of this structure is also so that high-visibility pigment of the present invention has extremely strong luminous intensity and excellent light fastness, wherein, described benzoxazinone luminous intensity can reach the nearly twice of common benzoxazinone high-visibility pigment, has the characteristic of outstanding high luminous intensity.
(2) high-visibility pigment of the present invention; selection A is that oxygen, B are that alkylsulfonyl, R are the 4-chloro-phenyl-; it has outstanding high-melting-point, high luminous intensity and organic solvent resistance; it is lower to be at wavelength that 365nm illumination excites; main emission peak is near 507nm, and luminous intensity is high, and fusing point is up to 283 ℃; at organic solvent, especially the solubleness in ethyl acetate, acetone, toluene is less than 1wt%.Have excellent luminous intensity and organic solvent resistance when being applied in melt-spinning fiber, the coloured or colourless anti-forgery ink.
Description of drawings
Fig. 1 is the infrared spectrum of 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone.
Embodiment
Below in conjunction with embodiment, the present invention is further described in detail, but is not limited to this.
Embodiment 1
Synthesizing of 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone
Get 19.7g(0.1mol) 4,5-dimethoxy anthranilic acid, be dissolved in the pyridine of 50ml, and the there-necked flask of the 250ml that packs into.Then, with 46.42g(0.22mol) parachloroben-zenesulfonyl chloride is dissolved in the 80ml pyridine, dropwise is added drop-wise in the there-necked flask by dropping funnel and stirs, and the control bath temperature is less than 30 ℃.Reacted sedimentation and filtration, separation 1-3 hours.Filter cake is successively used 100ml acetone, 100ml 8wt% salt acid elution, then water flush away free acid, oven dry, pressed powder is recrystallization in chloroform, get little green solid powder 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone 22.65g.
Productive rate 85.0%, 281～284 ℃ of fusing points, maximum emission wavelength λ
Max=507nm, the solubleness in acetone, butanone and ethyl acetate is all less than 1wt%.
Ultimate analysis calculated value: C, 54.08; H, 3.98; N, 5.26; S, 6.02
Ultimate analysis measured value: C, 53.56; H, 3.83; N, 5.18; S, 5.89.
Embodiment 2
Synthesizing of 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-fluorobenzene sulfonamido)] phenyl-4-benzoxazinone
Get 19.7g(0.1mol) 4,5-dimethoxy anthranilic acid, be dissolved in the pyridine of 50ml, and the there-necked flask of the 250ml that packs into.Then, with 42.79g(0.22mol) the fluorobenzene SULPHURYL CHLORIDE is dissolved in the 80ml pyridine, dropwise being added drop-wise in the there-necked flask by dropping funnel and stirring, the control bath temperature is less than 30 ℃.Reacted sedimentation and filtration, separation 1 ~ 3 hour.Filter cake is successively used 100ml acetone, 100ml 8wt% salt acid elution, then water flush away free acid, oven dry, pressed powder is recrystallization in chloroform, get little green solid powder 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-fluorobenzene sulfonamido)] phenyl-4-benzoxazinone 21.44g.
Productive rate 83.0%, 273～276 ℃ of fusing points, maximum emission wavelength λ
Max=504nm, the solubleness in acetone, butanone and ethyl acetate is all less than 1wt%.
Ultimate analysis calculated value: C, 55.80; H, 4.11; N, 5.42; S, 6.21
Ultimate analysis measured value: C, 55.50; H, 4.01; N, 5.28; S, 6.09.
?
Embodiment 3
Synthesizing of 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-Methyl benzenesulfonyl is amino)] phenyl-4-benzoxazinone
Get 19.7g(0.1mol) 4,5-dimethoxy anthranilic acid, be dissolved in the pyridine of 50ml, and the there-necked flask of the 250ml that packs into.Then, with 41.91g(0.22mol) p-methyl benzene sulfonic chloride is dissolved in the 80ml pyridine, dropwise is added drop-wise in the there-necked flask by dropping funnel and stirs, and the control bath temperature is less than 30 ℃.Reacted sedimentation and filtration, separation 1-3 hours.Filter cake is successively used 100ml acetone, 100ml 8wt% salt acid elution, then water flush away free acid, oven dry, pressed powder is recrystallization in chloroform, get little yellow solid powder 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-Methyl benzenesulfonyl is amino)] phenyl-4-benzoxazinone 21.78g.
Productive rate 85.0%, 268～271 ℃ of fusing points, maximum emission wavelength λ
Max=544nm, the solubleness in acetone, butanone and ethyl acetate is all less than 1wt%.
Ultimate analysis calculated value: C, 58.58; H, 4.73; N, 5.47; S, 6.26
Ultimate analysis measured value: C, 58.22; H, 4.58; N, 5.33; S, 6.18.
Embodiment 4
Synthesizing of 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-(3H)-quinazolinone
With synthetic 10.66g(0.02mol) 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone is dissolved in the 100ml methylcyclohexane, places the 500ml there-necked flask.At room temperature add 200ml ammoniacal liquor, stir half an hour, then process with aqueous sodium hydroxide solution, temperature is elevated to 85 ℃, refluxes 1-2 hours.Cooling, about 40ml carries out acidifying with the 18wt% dilute acetic acid, until solution is neutral, has a large amount of precipitations to generate.Water, ethanol wash respectively, filtration, drying, and powder is recrystallization in orthodichlorobenzene, obtains white solid 7.66g.
341～343 ℃ of productive rate 72% fusing points, maximum emission wavelength λ
Max=487nm, the solubleness in acetone, butanone and ethyl acetate is all less than 1wt%.
Ultimate analysis calculated value: C, 54.18; H, 4.18; N, 7.90; S, 6.03
Ultimate analysis measured value C, 53.94; H, 4.06; N, 7.68; S, 5.89
Embodiment 5
Synthesizing of 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzoyl is amino)] phenyl-4-benzoxazinone
Get 19.7g(0.1mol) 4,5-dimethoxy anthranilic acid, be dissolved in the pyridine of 50ml, and the there-necked flask of the 250ml that packs into.Then, with 38.5g(0.22mol) parachlorobenzoyl chloride is dissolved in the 80ml pyridine, dropwise is added drop-wise in the there-necked flask by dropping funnel and stirs, and the control bath temperature is less than 30 ℃.Reacted sedimentation and filtration, separation 1-3 hours.Filter cake is successively used 100ml acetone, 100ml 8wt% salt acid elution, then water flush away free acid, oven dry, pressed powder is recrystallization in chloroform, get white solid powder 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzoyl is amino)] phenyl-4-benzoxazinone 18.63g.
Productive rate 75.0%, 264～267 ℃ of fusing points, maximum emission wavelength λ
Max=455nm, the solubleness in acetone, butanone and ethyl acetate is all less than 1wt%.
Ultimate analysis calculated value: C, 60.42; H, 4.27; N, 5.64
Ultimate analysis measured value: C, 60.18; H, 4.18; N, 5.53.
Embodiment 6
Synthesizing of 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzoyl is amino)] phenyl-4-(3H)-quinazolinone
With synthetic 9.94g(0.02mol) 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzoyl is amino)] phenyl-4-benzoxazinone is dissolved in the 100ml methylcyclohexane, places the 500Mml there-necked flask.At room temperature add 200ml ammoniacal liquor, stir half an hour, then process with aqueous sodium hydroxide solution, temperature is elevated to 85 ℃, refluxes 1-2 hours.Cooling, about 40ml carries out acidifying with the 18wt% dilute acetic acid, until solution is neutral, has a large amount of precipitations to generate.Water, ethanol wash respectively, filtration, drying, and powder is recrystallization in orthodichlorobenzene, obtains white solid 7.24g.
324～327 ℃ of productive rate 73.0% fusing points, maximum emission wavelength λ
Max=440nm, the solubleness in acetone, butanone and ethyl acetate is all less than 1wt%.
Ultimate analysis calculated value: C, 60.54; H, 4.48; N, 8.48
Ultimate analysis measured value C, 60.17; H, 4.36; N, 8.39.
Comparative Examples
For further checking high-visibility pigment of the present invention has the fusing point height, organic solvent resistance is good, luminous intensity is extremely strong, the present invention also is provided with Comparative Examples, and the structural formula of the described high-visibility pigment of Comparative Examples is as follows:
Synthesizing of 2-[2-(4-Methyl benzenesulfonyl is amino)] phenyl-4-benzoxazinones
Get 13.7g(0.1mol) anthranilic acid, be dissolved in the pyridine of 50ml, and the there-necked flask of the 250ml that packs into.Then, with 41.91g(0.22mol) p-methyl benzene sulfonic chloride is dissolved in the 80ml pyridine, dropwise is added drop-wise in the there-necked flask by dropping funnel and stirs, and the control bath temperature is less than 30 ℃.Reacted sedimentation and filtration, separation 1-3 hours.Filter cake is successively used 100ml acetone, 100ml 8wt% salt acid elution, and then water flush away free acid is dried, and pressed powder is recrystallization in chloroform, gets pale solid powder 2-[2-(4-Methyl benzenesulfonyl is amino)] phenyl-4-benzoxazinone 14.72g.
Productive rate 75.0%, 214～217 ℃ of fusing points, maximum emission wavelength λ
Max=521nm, the solubleness in acetone is greater than 20wt%.
Ultimate analysis calculated value: C, 64.26; H, 4.12; N, 7.14; S, 8.17
Ultimate analysis measured value: C, 63.92; H, 4.01; N, 7.03; S, 8.11.
The performance evaluation example
Fusing point and solubility property evaluation:
By to the high-visibility pigment described in the embodiment 1 ~ 6 with the high-visibility pigment described in the Comparative Examples carries out fusing point and organic solvent resistance is tested, wherein organic solvent comprises acetone, butanone and ethyl acetate, and test result sees Table 1.Wherein, described fusing point testing method to high-visibility pigment adopts Stamford MELTING POINT TESTER test commonly used in the chemistry.
Table 1
| The embodiment numbering | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | Comparative Examples |
| Fusing point (℃) | 281~284 | 273~276 | 268~271 | 341~343 | 264~267 | 324~327 | 214~217 |
| Solubility property | ＜1wt% | ＜1wt% | ＜1wt% | ＜1wt% | ＜1wt% | ＜1wt% | >20wt% |
By the above results as can be known, the fusing point of embodiment 1 ~ 3 and embodiment 5 described benzoxazinone high-visibility pigments all is higher than 260 ℃, the fusing point of the quinazolinone high-visibility pigment described in embodiment 4 and the embodiment 6 is higher than 320 ℃, and reach as high as 343 ℃, and the fusing point of the high-visibility pigment of benzoxazinone described in the Comparative Examples only has 214 ~ 217 ℃, the fusing point that high-visibility pigment of the present invention is described is high, and especially the benzoxazinone high-visibility pigment can be directly used in and prepare anti-false fiber in the melt-spinning fiber.In addition, embodiment 1 ~ 6 described high-visibility pigment also has excellent organic solvent resistance, and its solubleness in acetone, butanone and ethyl acetate is all less than 1wt%, and the solubleness of the high-visibility pigment described in the Comparative Examples in acetone is then greater than 20wt%.
The fluorescence intensity performance test:
Adopt Shimadzu RF-5301 spectrophotofluorometer that the high-visibility pigment described in above-described embodiment 1 ~ 6 and the high-visibility pigment described in the Comparative Examples are carried out the fluorescence intensity test, test result is as shown in table 2.
Table 2
Table 2
By above-mentioned fluorescence intensity the performance test results as can be known, high-visibility pigment of the present invention has extremely strong fluorescence intensity, especially the benzoxazinone high-visibility pigment described in the embodiment 1 ~ 3, its fluorescence intensity (representing with peak height) is up to more than 448, and 6 described in the embodiment 1,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] its fluorescence intensity of phenyl-4-benzoxazinone even up to 487.2 is 1.75 times of the fluorescence intensity of high-visibility pigment described in the Comparative Examples.The above results shows that high-visibility pigment of the present invention has extremely strong fluorescence intensity.
Examination of infrared spectrum:
Embodiment 1 described 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone is carried out examination of infrared spectrum, adopt the KBr pressed disc method to test, test gained infrared spectrum as shown in Figure 1.As shown in Figure 1,1606cm
-1, 1580 cm
-1And 1504cm
-1Charateristic avsorption band for phenyl ring; 1247cm
-1And 1212cm
-1Be the antisymmetric stretching vibration charateristic avsorption band of C-O-C, 1010 cm
-1And 1023cm
-1Symmetrical stretching vibration charateristic avsorption band for C-O-C has illustrated the existence of the methoxyl group that is connected with phenyl ring; 1278cm
-1Be the nonsymmetrical vibration absorption peak of sulphonamide, 1141cm
-1Symmetric vibration absorption peak for sulphonamide; 943cm
-1Be the charateristic avsorption band of oxazines ring structure, the existence of oxazines ring has been described; 754 cm
-1The strong peak at place is the stretching vibration absorption peak of C-Cl; Above-mentioned characteristic peak shows 4,5-dimethoxy anthranilic acid and parachloroben-zenesulfonyl chloride are through polycondensation, generated 6,7-dimethoxy of the present invention-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone.
Obviously, above-described embodiment only is for example clearly is described, and is not the restriction to embodiment.For those of ordinary skill in the field, can also make other changes in different forms on the basis of the above description.Here need not also can't give all embodiments exhaustive, and the apparent variation of being extended out thus or the change still be among the protection domain of the invention claim.
Claims (9)
1. high-visibility pigment that represents with following structural:
Wherein: A is oxygen or secondary amine, and B is alkylsulfonyl or carbonyl, and R is phenyl or with substituent phenyl.
2. described high-visibility pigment according to claim 1 is characterized in that, described is phenyl with para-orienting group with substituent phenyl.
3. described high-visibility pigment according to claim 2 is characterized in that described phenyl with para-orienting group is 4-chloro-phenyl-, 4-aminomethyl phenyl or 4-fluorophenyl.
4. arbitrary described high-visibility pigment is characterized in that according to claim 1 ~ 3, and described A is that oxygen, B are alkylsulfonyl, and R is the 4-chloro-phenyl-.
5. arbitrary described high-visibility pigment is characterized in that according to claim 1 ~ 4, and the wavelength of fluorescence that described high-visibility pigment sends is 450 ~ 560nm.
6. arbitrary described high-visibility pigment is characterized in that according to claim 1 ~ 5, and the fusing point of described high-visibility pigment is 260 ~ 350 ℃.
7. arbitrary described high-visibility pigment is characterized in that according to claim 1 ~ 6, and the solubleness of described high-visibility pigment in organic solvent is less than 1wt%.
8. described high-visibility pigment according to claim 7 is characterized in that described organic solvent is acetone, ethyl acetate or butanone.
9. the arbitrary described high-visibility pigment of claim 1 ~ 8 is used for the purposes of melt-spinning fiber, coloured or colourless anti-forgery ink.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108164708A (en) * | 2017-12-19 | 2018-06-15 | 济南大学 | A kind of preparation method of-benzoxazinyl selfreparing elastomeric material of novel fluorescence polysiloxanes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996005266A1 (en) * | 1994-08-08 | 1996-02-22 | Hoechst Aktiengesellschaft | Organic electroluminescent device |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996005266A1 (en) * | 1994-08-08 | 1996-02-22 | Hoechst Aktiengesellschaft | Organic electroluminescent device |
Non-Patent Citations (1)
| Title |
|---|
| 张文官,赵生敏: "6-甲氧基-2-[5-甲氧基-2-(4-甲基苯磺酰氨基)]苯基-4-苯并恶嗪酮的合成及荧光性能", 《精细化工》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108164708A (en) * | 2017-12-19 | 2018-06-15 | 济南大学 | A kind of preparation method of-benzoxazinyl selfreparing elastomeric material of novel fluorescence polysiloxanes |
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Effective date of registration: 20210416 Address after: 100070 8th floor, building 2, No.5 Zhonghe Road, Fengtai Science City, Fengtai District, Beijing Patentee after: China Banknote Printing Technology Research Institute Co.,Ltd. Patentee after: CHINA BANKNOTE PRINTING AND MINTING Corp. Address before: 100070 science Road 5, Beijing, Fengtai District Patentee before: SECURITY PRINTING INSTITUTE OF PEOPLE'S BANK OF CHINA Patentee before: CHINA BANKNOTE PRINTING AND MINTING Corp. |
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Address after: 100070 8th floor, building 2, No.5 Zhonghe Road, Fengtai Science City, Fengtai District, Beijing Patentee after: China Banknote Printing Technology Research Institute Co.,Ltd. Patentee after: China Banknote Printing and Minting Group Co.,Ltd. Address before: 100070 8th floor, building 2, No.5 Zhonghe Road, Fengtai Science City, Fengtai District, Beijing Patentee before: China Banknote Printing Technology Research Institute Co.,Ltd. Patentee before: CHINA BANKNOTE PRINTING AND MINTING Corp. |
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