CN103044946B - Fluorescent pigment - Google Patents
Fluorescent pigment Download PDFInfo
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- CN103044946B CN103044946B CN201210207386.4A CN201210207386A CN103044946B CN 103044946 B CN103044946 B CN 103044946B CN 201210207386 A CN201210207386 A CN 201210207386A CN 103044946 B CN103044946 B CN 103044946B
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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 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 visible light wave range is absorbed by high-visibility pigment, afterwards, with the electromagnetic form of long wavelength, discharges.Long wavelength's hertzian wave drops in visible-range conventionally, and itself and conventional optical superposition of reflecting, show dazzling fluorescence color; And after light stops irradiating, luminescence phenomenon disappears, and is therefore called high-visibility pigment.
Benzoxazinone and quinazolinone all belong to high-visibility pigment, on the books in the prior art.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, through polycondensation, prepare.Quinazolinone high-visibility pigment is by benzoxazinone and ammoniacal liquor or ammonia, in the water miscible organic solvent of inertia, and under alkali metal hydroxide exists, further after reaction, obtains.The quinazolinone that benzoxazinone continues and ammonia react prepares with fluorescence property also has fluorescence property.
In prior art, the fusing point of benzoxazinone high-visibility pigment is generally all lower than 240 ℃, and organic solvent resistance is 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 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 under the existence of sodium hydroxide, through reaction, prepares.Wherein, as shown in Equation 1, the structural formula of quinazolinone as shown in Equation 2 for the structural formula of benzoxazinone.In this technology, quinazolinone, under solid-state form exists, under UV rayed, can send fluorescence in the visible region of 500～540nm.But, in this technology, the fusing point of benzoxazinone is only 170～223 ℃, and the fusing point of the quinazolinone being 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 at melt-spinning, prepare the application in anti-false fiber, melt-spinning is prepared the temperature of general requirement high-visibility pigment in anti-false fiber higher than 250 ℃.In addition also all there is the poor problem of organic solvent resistance in above-mentioned benzoxazinone and quinazolinone.
formula 1
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
2for 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 generation quinazolinone, it has higher fusing point, and benzoxazinone or quinazolinone also all have stronger organic solvent resistance, especially there is the performance of the organic solvents such as excellent resistance to ethyl acetate, acetone, toluene, but in prior art, could not obtain having the high-visibility pigment of this performance always.
Summary of the invention
Technical problem to be solved by this invention is benzoxazinone fluorescent material and all have the poor problem of organic solvent resistance by its quinazolinone fluorescent material that further reaction generates in prior art, and benzoxazinone fluorescent material also exists low-melting problem, and then provide a kind of and there is fusing point 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 representing with following molecular formula:
Wherein: A is oxygen (-O-) or secondary amine (NH-), and B is alkylsulfonyl
or carbonyl
r is 4-chloro-phenyl-or 4-fluorophenyl.
Described A is that oxygen, B are alkylsulfonyl, and R is 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 for the purposes of melt-spinning fiber, coloured or colourless anti-forgery ink.
The present invention compared with prior art tool has the following advantages:
(1) high-visibility pigment of the present invention, in the structural formula of described high-visibility pigment, on the 6th and the 7th replacement position, adopt respectively methoxyl group to replace, the the 4th and the 5th of phenyl in the structural formula of described high-visibility pigment replaces on position and also adopts the methoxyl group to replace, and has replaced in prior art at the described normal H adopting or the halogen of replacing on position as substituent situation.Its molecular volume of high-visibility pigment with structure of the present invention is greater than the molecular volume of this type of high-visibility pigment in routine techniques, and the variation of molecular structure makes high-visibility pigment of the present invention have 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 in the structural formula of described high-visibility pigment, A is O, its fusing point is higher than 260 ℃, and when A is secondary amine, its fusing point is higher than 340 ℃.In addition, the variation of this structure also makes high-visibility pigment of the present invention have 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 4-chloro-phenyl-; it has outstanding high-melting-point, high luminous intensity and organic solvent resistance; at wavelength, be under 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%.While being applied in melt-spinning fiber, coloured or colourless anti-forgery ink, there is excellent luminous intensity and organic solvent resistance.
Accompanying drawing explanation
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 pack the there-necked flask of 250ml into.Then, by 46.42g(0.22mol) parachloroben-zenesulfonyl chloride is dissolved in 80ml pyridine, by dropping funnel, is dropwise added drop-wise in there-necked flask and stirs, and control bath temperature and be less than 30 ℃.React sedimentation and filtration, separation 1-3 hours.Filter cake is successively with 100ml acetone, 100ml8wt% salt acid elution, then water washes away free acid, dry, pressed powder is recrystallization in chloroform, obtain micro-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 pack the there-necked flask of 250ml into.Then, by 42.79g(0.22mol) fluorobenzene SULPHURYL CHLORIDE is dissolved in 80ml pyridine, by dropping funnel, be dropwise added drop-wise in there-necked flask and stir, control bath temperature and be less than 30 ℃.React sedimentation and filtration, separation 1～3 hour.Filter cake is successively with 100ml acetone, 100ml8wt% salt acid elution, then water washes away free acid, dry, pressed powder is recrystallization in chloroform, obtain micro-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 amino)] phenyl-4-benzoxazinone
Get 19.7g(0.1mol) 4,5-dimethoxy anthranilic acid, be dissolved in the pyridine of 50ml, and pack the there-necked flask of 250ml into.Then, by 41.91g(0.22mol) p-methyl benzene sulfonic chloride is dissolved in 80ml pyridine, by dropping funnel, is dropwise added drop-wise in there-necked flask and stirs, and control bath temperature and be less than 30 ℃.React sedimentation and filtration, separation 1-3 hours.Filter cake is successively with 100ml acetone, 100ml8wt% salt acid elution, then water washes away free acid, dry, pressed powder is recrystallization in chloroform, obtain micro-yellow solid powder 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-Methyl benzenesulfonyl 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
By synthetic 10.66g(0.02mol) 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone is dissolved in 100ml methylcyclohexane, is placed in 500ml there-necked flask.At room temperature add 200ml ammoniacal liquor, stir half an hour, then with aqueous sodium hydroxide solution, process, temperature is elevated to 85 ℃, refluxes 1-2 hours.Cooling, with 18wt% dilute acetic acid, about 40ml carries out acidifying, until solution is neutral, has a large amount of precipitations to generate.Water, ethanol wash respectively, filter, be dried, 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 amino)] phenyl-4-benzoxazinone
Get 19.7g(0.1mol) 4,5-dimethoxy anthranilic acid, be dissolved in the pyridine of 50ml, and pack the there-necked flask of 250ml into.Then, by 38.5g(0.22mol) parachlorobenzoyl chloride is dissolved in 80ml pyridine, by dropping funnel, is dropwise added drop-wise in there-necked flask and stirs, and control bath temperature and be less than 30 ℃.React sedimentation and filtration, separation 1-3 hours.Filter cake is successively with 100ml acetone, 100ml8wt% salt acid elution, then water washes away free acid, dry, pressed powder is recrystallization in chloroform, obtain white solid powder 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzoyl 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 amino)] phenyl-4-(3H)-quinazolinone
By synthetic 9.94g(0.02mol) 6,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzoyl amino)] phenyl-4-benzoxazinone is dissolved in 100ml methylcyclohexane, is placed in 500Mml there-necked flask.At room temperature add 200ml ammoniacal liquor, stir half an hour, then with aqueous sodium hydroxide solution, process, temperature is elevated to 85 ℃, refluxes 1-2 hours.Cooling, with 18wt% dilute acetic acid, about 40ml carries out acidifying, until solution is neutral, has a large amount of precipitations to generate.Water, ethanol wash respectively, filter, be dried, 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 example
For further checking high-visibility pigment of the present invention has, fusing point is high, organic solvent resistance good, luminous intensity is extremely strong, and the present invention is also provided with comparative example, and the structural formula of high-visibility pigment is as follows described in comparative example:
Synthesizing of 2-[2-(4-Methyl benzenesulfonyl amino)] phenyl-4-benzoxazinones
Get 13.7g(0.1mol) anthranilic acid, be dissolved in the pyridine of 50ml, and pack the there-necked flask of 250ml into.Then, by 41.91g(0.22mol) p-methyl benzene sulfonic chloride is dissolved in 80ml pyridine, by dropping funnel, is dropwise added drop-wise in there-necked flask and stirs, and control bath temperature and be less than 30 ℃.React sedimentation and filtration, separation 1-3 hours.Filter cake is successively with 100ml acetone, 100ml8wt% salt acid elution, and then water washes away free acid, dries, and pressed powder is recrystallization in chloroform, obtains pale solid powder 2-[2-(4-Methyl benzenesulfonyl 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 for being 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.
performance evaluation example
Fusing point and solubility property evaluation:
By to the high-visibility pigment described in embodiment 1～6 with the high-visibility pigment described in comparative example carries out fusing point and organic solvent resistance is tested, wherein organic solvent comprises acetone, butanone and ethyl acetate, and test result is in Table 1.Wherein, the described fusing point testing method to high-visibility pigment adopts Stamford MELTING POINT TESTER test conventional in chemistry.
Table 1
From the above results, the fusing point of the benzoxazinone high-visibility pigment described in embodiment 1～3 and embodiment 5 is all higher than 260 ℃, the fusing point of the quinazolinone high-visibility pigment described in embodiment 4 and 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 comparative example only has 214～217 ℃, the fusing point that high-visibility pigment of the present invention is described is high, and especially benzoxazinone high-visibility pigment can be directly used in and in melt-spinning fiber, prepare anti-false fiber.In addition, the high-visibility pigment described in embodiment 1～6 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 comparative example in acetone is greater than 20wt%.
Fluorescence intensity performance test:
Adopt Shimadzu RF-5301 spectrophotofluorometer to carry out fluorescence intensity test to the high-visibility pigment described in above-described embodiment 1～6 and the high-visibility pigment described in comparative example, test result is as shown in table 2.
Table 2
Table 2
From above-mentioned fluorescence intensity the performance test results, high-visibility pigment of the present invention has extremely strong fluorescence intensity, especially the benzoxazinone high-visibility pigment described in embodiment 1～3, its fluorescence intensity (representing with peak height) is up to more than 448, and 6 described in embodiment 1,7-dimethoxy-2-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] its fluorescence intensity of phenyl-4-benzoxazinone is even up to 487.2, is 1.75 times of the fluorescence intensity of high-visibility pigment described in comparative example.The above results shows that high-visibility pigment of the present invention has extremely strong fluorescence intensity.
Examination of infrared spectrum:
6,7-dimethoxy-2 described in embodiment 1-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone is carried out to examination of infrared spectrum, adopt KBr pressed disc method to test, test gained infrared spectrum as shown in Figure 1.As shown in Figure 1,1606cm
-1, 1580cm
-1and 1504cm
-1for the charateristic avsorption band of phenyl ring; 1247cm
-1and 1212cm
-1for the antisymmetric stretching vibration charateristic avsorption band of C-O-C, 1010cm
-1and 1023cm
-1for the symmetrical stretching vibration charateristic avsorption band of C-O-C, the existence of the methoxyl group being connected with phenyl ring has been described; 1278cm
-1for the nonsymmetrical vibration absorption peak of sulphonamide, 1141cm
-1for the symmetric vibration absorption peak of sulphonamide; 943cm
-1for the charateristic avsorption band of oxazines ring structure, the existence of oxazines ring has been described; 754cm
-1the stretching vibration absorption peak that the strong peak at place is C-Cl; Above-mentioned characteristic peak shows 4,5-dimethoxy anthranilic acid and parachloroben-zenesulfonyl chloride are through polycondensation, generated 6,7-dimethoxy-2 of the present invention-[4,5-dimethoxy-2-(4-chlorobenzene sulfonamido)] phenyl-4-benzoxazinone.
Obviously, above-described embodiment is only for example is clearly described, and the not 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 exhaustive without also giving all embodiments, and the apparent variation of being extended out thus or variation are still among the protection domain in the invention claim.
Claims (7)
1. the high-visibility pigment representing with following structural:
Wherein: A is oxygen or secondary amine, B is alkylsulfonyl or carbonyl, and R is 4-chloro-phenyl-or 4-fluorophenyl.
2. high-visibility pigment according to claim 1, is characterized in that, described A is that oxygen, B are alkylsulfonyl, and R is 4-chloro-phenyl-.
3. according to high-visibility pigment described in claim 1 or 2, it is characterized in that, the wavelength of fluorescence that described high-visibility pigment sends is 450～560nm.
4. according to high-visibility pigment described in claim 1 or 2, it is characterized in that, the fusing point of described high-visibility pigment is 260～350 ℃.
5. according to high-visibility pigment described in claim 1 or 2, it is characterized in that, the solubleness of described high-visibility pigment in organic solvent is less than 1wt%.
6. high-visibility pigment according to claim 5, is characterized in that, described organic solvent is acetone, ethyl acetate or butanone.
7. the arbitrary described high-visibility pigment of claim 1～6 is for the purposes of melt-spinning fiber, coloured or colourless anti-forgery ink.
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| WO1996005266A1 (en) * | 1994-08-08 | 1996-02-22 | Hoechst Aktiengesellschaft | Organic electroluminescent device |
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| WO1996005266A1 (en) * | 1994-08-08 | 1996-02-22 | Hoechst Aktiengesellschaft | Organic electroluminescent device |
Non-Patent Citations (2)
| Title |
|---|
| 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;张文官,赵生敏;《精细化工》;20030731;第20卷(第7期);第390页左栏第1行-第391页左栏第2行 * |
| 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》.2003,第20卷(第7期), |
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