CN103483328B - A kind of toluylene white dyes and its preparation method and application - Google Patents
A kind of toluylene white dyes and its preparation method and application Download PDFInfo
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- CN103483328B CN103483328B CN201310390254.4A CN201310390254A CN103483328B CN 103483328 B CN103483328 B CN 103483328B CN 201310390254 A CN201310390254 A CN 201310390254A CN 103483328 B CN103483328 B CN 103483328B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/148—Stilbene dyes containing the moiety -C6H5-CH=CH-C6H5
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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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/07—Nitrogen-containing compounds
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses a kind of toluylene white dyes and its preparation method and application.The synthesis of described toluylene white dyes specifically comprises two reactions steps: the esterification of triethyl-phosphite and Wittig-Horner reaction.This synthesising method reacting condition is gentle, productive rate is high, be easy to separation, being applicable to industrialization and this white dyes is take toluylene as the non-ionic type whitening agent of " light wave transmodulator ", not only there is the character of optical whitening agent, also there is antibiotic and sterilizing effect, environmental protection, white dyes that is friendly for development environment, new high-efficiency has important using value.
Description
Technical field
The invention belongs to field of fine chemical, be specifically related to a kind of preparation method and application of toluylene white dyes.
Background technology
Present white dyes, known by people, is applied to many fields such as weaving, coating, plastics, washing and papermaking in a large number, and the fabric after being added or paper become and brighten, increase gorgeous and blast.Wherein, papermaking is one of topmost Application Areas of whitening agent, and continually developing the high performance white dyes being suitable for paper grade (stock) is study hotspot in recent years.
White dyes is that a class absorbs UV-light, launches blue or indigo fluorescent substance.The definition of standard GB/T/T6687-1986 to it is: white dyes is a kind of colourless fluorescence dye, under the irradiation of UV-light, can excite indigo plant, purple light, complementary and have whitening effect with the gold-tinted in matrix.Because brightening of white dyes is according to optics complementarity principle, when applying this kind of mass treatment white or light product, can obtain brighten, effect that blast, increasing are gorgeous.So white dyes is also called optical whitening agent usually.
As white dyes, its molecule all has the planar conjugate system formed by π-electron.White dyes is contaminated in the matrix having certain whiteness by upper someway, this matrix is under the irradiation of the light source of sunlight or UV-light, reflect visible light, absorb the energy of invisible UV-light (about 340nm-380nm), make molecular activation, revert back to ground state again, ultraviolet energy just disappears a part, then emits with bright fluorescent form in the visible region of royal purple light (410nm-480nm).This bluish voilet fluorescence mixes with the micro-sodium yellow in matrix, and (yellow is hepatic complementary color) obtains white light, and has whitening effect.
Stilbene-based Fluorescent Brighteners is the fluorescent bleaches that application is maximum at present, is widely used in weaving, papermaking and synthesis of detergent etc. industrial.Stilbene-based Fluorescent Brighteners is the most important chemical structural type of whitening agent, no matter is that output or kind number all occupy first of various structure.The country of every production white dyes and company produce the product of this class formation type invariably.Such white dyes accounts for absolute advantage at home with in the kind of external whitening agent.Paper industry also mainly uses such whitening agent.
Current Stilbene-based Fluorescent Brighteners building-up process is more complicated, and productive rate is general, uses a large amount of acid, cause environmental pollution in production process, and the white dyes fluorescence intensity of synthesis is lower, and whiteness is not high.
Summary of the invention
For above-mentioned prior art, a kind of preparation method and application with the toluylene white dyes of germicidal action that the invention provides.
A kind of containing toluylene white dyes, concrete structure formula is as follows:
The object of the present invention is to provide a kind of preparation method of toluylene white dyes, its synthetic route is as follows:
The preparation method of above-mentioned whitening agent, specifically comprises the following steps:
(1) esterification of triethyl-phosphite
Be 1:(1.1 ~ 1.5 by mol ratio) A and oily liquids triethyl-phosphite mixed dissolution after, stirring and refluxing 3 ~ 5h under temperature is 125 ~ 130 DEG C of conditions, after triethyl-phosphite excessive in decompression removing reaction system, while hot stir add normal hexane separate out solid product, then use 1:(1 ~ 4) tetrahydrofuran (THF) and normal hexane mixed solution recrystallization obtain product B.
(2) Wittig-Horner reaction
Respectively the product B obtained by equimolar piperonal and step (1) is dissolved in DMF and obtains lysate; In described lysate, add the ethanol solution that mass percent is the potassium tert.-butoxide of 15 ~ 30%, under 60 ~ 70 DEG C of conditions, stirring reaction 5h obtains reaction solution, cools and filters described reaction solution; Gained filter cake volume ratio is (2 ~ 3): dimethyl sulfoxide (DMSO) and the alcohol mixeding liquid recrystallization of 1 obtain final product, namely containing 1,3,4-oxadiazole toluylene white dyes.DMF is 10 ~ 15ml/g with the volume mass ratio of product B.
Compared with prior art, the present invention has following beneficial effect:
(1) toluylene white dyes provided by the invention has strong fluorescence intensity and whiteness.In paper-making process, carry out fluorescent brightening to paper pulp, pH value is at 6-8, and consumption is the 0.05-0.5% of paper pulp consumption.
(2) application of whitening agent of the present invention in papermaking.Whitening agent of the present invention also has anti-microbial effect, and it has bacteriostatic action to Candida albicans, and therefore, this whitening agent can also be used in sterilant.
Accompanying drawing explanation
Fig. 1 is the uv-visible absorption spectra figure of whitening agent of the present invention in different solvents.
Fig. 2 is the fluorescence emission spectrogram of whitening agent of the present invention in different solvents.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but the scope of protection of present invention is not limited thereto.
The fusing point of the final product obtained by embodiment and nuclear magnetic resonance data are recorded by RY-1 melting point apparatus (Tianjin analytical instrument factory) and BrukerAVANCE-400NMR nuclear magnetic resonance analyser (Brooker,Switzerland company) respectively.The raw materials used 2-naphthyl of the present invention-5-(4-(brooethyl) phenyl)-1,3,4-oxadiazoles are published on SoftMatter magazine by people such as ParulRungta, are published in the synthetic method preparation on DysandPigments magazine according to people such as LiXinwei.
The synthesis of embodiment 11,3,4-oxadiazole toluylene white dyes (I)
(1) by 0.0088mol2-naphthyl-5-(4-(brooethyl) phenyl)-1,3,4-oxadiazole is dissolved in 0.0132mol triethyl-phosphite, is heated to 130 DEG C, stirring and refluxing reaction 5h, after triethyl-phosphite excessive in pressure reducing and steaming reaction system, stir while hot and add 5ml normal hexane and separate out solid product, then obtain 3.32g4-(5-naphthyl-1,3 with the tetrahydrofuran (THF) of 1:1 and normal hexane mixed solution recrystallization, 4-oxadiazole-2-base) phenmethyl phosphonic acid ester, productive rate: 89.4%.Fusing point: 139-140 DEG C.Proton nmr spectra structural characterization data:
1hNMR (400MHz, CDCl
3) δ 9.30 (d, J=8.6Hz, 1H, naphthalene-H), 8.29 (d, J=7.2Hz, 1H, naphthalene-H), 8.18 (d, J=7.9Hz, 2H, C
6h
4, 2,6-H), 8.07 (d, J=8.2Hz, 1H, naphthalene-H), 7.97 (d, J=8.1Hz, 1H, naphthalene-H), 7.73 (t, J=7.7Hz, 1H, naphthalene-H), 7.63 (t, J=7.6Hz, 2H, naphthalene-H), 7.53 (d, J=7.9Hz, 2H, C
6h
4, 3,5-H), 4.08 (q, J=7.2Hz, 4H, CH
2), 3.27 (d, J=22.1Hz, 2H, CH
2), 1.30 (t, J=7.0Hz, 6H, CH
3).
(2) by 0.002mol4-(5-naphthyl-1,3,4-oxadiazole-2-base) phenmethyl phosphonic acid ester and 0.002mol piperonal be dissolved in 15mlN, in dinethylformamide, then in solution, drip the ethanol solution 3ml that mass ratio is the potassium tert.-butoxide of 30%, at 70 DEG C, stirring reaction 5h obtains reaction solution, cools and filters, gained solid volume ratio is that the dimethyl sulfoxide (DMSO) of 3:1 and alcohol mixeding liquid recrystallization obtain 0.77g, productive rate: 92.0%.Fusing point: 184-186 DEG C.Proton nmr spectra structural characterization data:
1hNMR (400MHz, CDCl
3) δ 9.30 (d, J=8.6Hz, 1H, naphthalene-H), 8.28 (dd, J=10.4,3.9Hz, 1H, naphthalene-H), 8.17 (d, J=8.3Hz, 2H, C
6h
4, 2,6-H), 8.06 (d, J=8.1Hz, 1H, naphthalene-H), 7.95 (d, J=8.1Hz, 1H, naphthalene-H), 7.71 (t, J=7.1Hz, 1H, naphthalene-H), 7.68-7.58 (m, 4H, C
6h
4, 2,6-H, naphthalene-H), 7.16 (d, J=16.2Hz, 1H, CH=CH), 7.10 (d, J=1.4,1H, C
6h
3, 2-H), 7.00-6.96 (m, 2H, C
6h
3, 6-H, CH=CH), 6.82 (d, J=8.0Hz, 1H, C
6h
3, 5-H), 6.00 (s, 2H, CH
2).Carbon-13 nmr spectra structural characterization data:
13cNMR (101MHz, CDCl
3) δ 164.48,164.11,148.30,147.90,140.95,133.90,132.56,131.29,130.74,130.15,128.68,128.36,128.19,127.39,126.83,126.74,126.29,125.70,124.89,122.31,122.12,120.59,108.52,105.66,101.28.
Embodiment 2
The synthesis of 1,3,4-oxadiazole toluylene white dyes (I)
(1) by 0.0088mol2-naphthyl-5-(4-(brooethyl) phenyl)-1,3,4-oxadiazole is dissolved in 0.0097mol triethyl-phosphite, is heated to 125 DEG C, stirring and refluxing reaction 3h, after triethyl-phosphite excessive in pressure reducing and steaming reaction system, stir while hot and add 5ml normal hexane and separate out solid product, then obtain 2.98g4-(5-naphthyl-1,3 with the tetrahydrofuran (THF) of 1:4 and normal hexane mixed solution recrystallization, 4-oxadiazole-2-base) phenmethyl phosphonic acid ester, productive rate: 80.2%.
(2) by 0.0020mol4-(5-naphthyl-1,3,4-oxadiazole-2-base) phenmethyl phosphonic acid ester and 0.0020mol piperonal be dissolved in 10mlN, in dinethylformamide, then in solution, drip the ethanol solution 4ml that mass ratio is the potassium tert.-butoxide of 15%, at 60 DEG C, stirring reaction 5h obtains reaction solution, cools and filters, gained solid volume ratio is that the dimethyl sulfoxide (DMSO) of 2:1 and alcohol mixeding liquid recrystallization obtain 0.71g, productive rate: 84.9%.
Embodiment 3
1, the mensuration of 1,3,4-oxadiazole toluylene white dyes ultraviolet
By compound (I) solution (DMSO, THF, CHCl with opposed polarity
3) be made into same concentrations 1 × 10
-5the solution of mol/L, it is that 200-500nm measures uv-absorbing that ultraviolet-visible spectrophotometer is got range of wavelengths, obtains its uv-visible absorption spectra (Fig. 1).
As can be seen from Figure 1, the uv-absorption maximum wavelength of white dyes in opposed polarity solution is respectively 363nm, 358nm and 350nm, there is red shift along with the increase of solution polarity and between the ultraviolet region all dropping on 340-380nm, illustrate that this white dyes can absorb the UV-light dropped in interval.
2, the mensuration of 1,3,4-oxadiazole toluylene white dyes fluorescence intensity
By compound (I) solution (DMSO, THF, CHCl with opposed polarity
2) be made into same concentrations 1 × 10
-5the solution of mol/L, measures its fluorescence with fluorescence analyser, obtains fluorescence emission spectrum (Fig. 2).
As can be seen from Figure 2, white dyes all shows stronger fluorescence intensity in opposed polarity solution, at THF and CHCl
2in solution, fluorescence intensity is greater than 1000, and maximum emission wavelength is respectively 490nm, 457nm and 449nm, along with the reduction of polarity, blue shift occurs.
Embodiment 4
Containing the application of the white dyes of 1,3,4-oxadiazole toluylene
Accurately take a certain amount of white dyes (I), be mixed with the different concns solution of 0.1 ~ 0.8g/L, carry out Coloration experiment: the qualitative fast grade filter paper of dyeing Ф 7 specification, and the uniform quality (0.320 ± 0.001g) of filter paper is often opened in adjustment, bath raio is 1:150, pH value range controls 6 ~ 8, dyeing 30min, dye finishes, and filter paper is suspended on shady and cool ventilation place and dries, whiteness is measured with whiteness instrument, with conventional fluorescent whitening agent VBL in contrast after dry.
Table 1 white dyes (I) whiteness under different concns
Experimental result shows, the whitening effect of product in lower concentration situation effect better and be better than conventional whitening agent VBL, along with the increase of concentration, whitening effect is fallen after rising, and whitening effect is best when 0.20g/L.Product uses under being applicable to low consistency conditions.
Embodiment 5
1,3,4-oxadiazole toluylene white dyes Determination of Antibacterial Activity.
1. experiment purpose
Test new white dyes and supply the bacteriostatic activity to Candida albicans under examination concentration.
2. experimental strain and material
This experiment use bacterial classification: Candida albicans is provided by Guangdong Province's microbial species resources bank.Material has Sharpe liquid nutrient medium and sabouraud's agar, 1%DMSO solution and antimicrobial drug fluconazole.
3. experimental technique
Odontothrips loti: accompanying dilution method to be configured to concentration with two white dyes (I) is 0.5mg/ml, 0.25mg/ml, the 1%DMSO solution [people such as Cui Guangfu has confirmed that 1%DMSO solution does not have bacteriostatic action to Candida albicans in " different concns dimethyl sulfoxide (DMSO) is to the bacteriostatic action research of Candida albicans "] of 0.125mg/ml, 0.0625mg/ml and 0.03125mg/ml.Get the Candida albicans after activation, be inoculated in liquid nutrient medium, at 27 DEG C, 12h cultivated by the shaking table of 200r/h, measures bacterium liquid OD value by microplate reader (OD600), and dilution bacterium liquid, make its OD value be in 0.1 ~ 0.2, namely bacteria suspension concentration is 10
5~ 10
6cFU/ml.Pipette above-mentioned bacteria suspension 100 μ l in containing on the flat board of solid medium with liquid-transfering gun, be coated with evenly, place Oxford cup, get above-mentioned liquid respectively in the cup of Oxford, culture dish is placed in 27 DEG C of incubators cultivation 24h, surveys inhibition zone size.Often group establishes three parallel laboratory tests, and 0.2g/L fluconazole solution in contrast.
4. test result
The bacteriostatic diameter (mm) of table 2 different concns white dyes
Drug sensitive experiment result criterion: antibacterial circle diameter >20 is extremely quick, 15-20 is quick during to be Gao Min, 10-14 be, <10 is muting sensitive, and 0 is unwise.
As can be seen from Table 1, white dyes (I) has obvious bacteriostatic action to Candida albicans, and concentration fungistatic effect when 0.25g/L is best, and when being greater than 0.25g/L, fungistatic effect have dropped.
Claims (9)
1. a toluylene white dyes, its chemical structure is as follows:
2. the preparation method of whitening agent described in claim 1, is characterized in that, comprises the following steps:
(1) be 1:(1.1 ~ 1.5 by mol ratio) 2-naphthyl-5-(4-(brooethyl) phenyl)-1,3, after 4-oxadiazole and oily liquids triethyl-phosphite mixed dissolution, stirring and refluxing 3 ~ 5h under temperature is 125 ~ 130 DEG C of conditions, after triethyl-phosphite excessive in removing reaction system, stir while hot and add normal hexane precipitation solid product, use the mixed solution recrystallization of tetrahydrofuran (THF) and normal hexane again, i.e. obtained product B, described product B is 4-(5-naphthyl-1,3,4-oxadiazole-2-base) phenmethyl phosphonic acid ester;
(2) respectively equimolar piperonal and product B are dissolved in DMF and obtain lysate; In described lysate, add the ethanol solution that mass percent is the potassium tert.-butoxide of 15 ~ 30%, carry out Wittig-Horner reaction, reaction terminates rear cooling and filters gained reaction solution; Gained filter cake volume ratio is (2 ~ 3): the dimethyl sulfoxide (DMSO) of 1 and alcohol mixeding liquid recrystallization, obtained toluylene white dyes.
3. preparation method according to claim 2, is characterized in that, in step (2), DMF is 10 ~ 15ml/g with the volume mass ratio of product B.
4. preparation method according to claim 2, is characterized in that, in step (2), the condition of Wittig-Horner reaction is: 60 ~ 70 DEG C of stirring reaction 5h.
5. the preparation method according to Claims 2 or 3 or 4, is characterized in that, described in step (1), the volume ratio of tetrahydrofuran (THF) and normal hexane is 1:(1 ~ 4).
6. the preparation method according to Claims 2 or 3 or 4, is characterized in that, carries out at reduced pressure conditions in step (1) during removing reaction system phosphorous acid triethyl.
7. the preparation method according to Claims 2 or 3 or 4, is characterized in that, the ethanol solution of potassium tert.-butoxide described in step (2) is 3 ~ 4ml/g with the volume mass ratio of product B.
8. the application of whitening agent in papermaking according to claim 1.
9. the application of whitening agent in sterilant according to claim 1.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853583A (en) * | 1971-04-12 | 1974-12-10 | T Langstroth | Fluorescent whitening compositions |
| WO1990010001A1 (en) * | 1989-03-01 | 1990-09-07 | Eastman Kodak Company | Process for the preparation of stilbene derivatives |
| CN102001949A (en) * | 2010-10-20 | 2011-04-06 | 华南理工大学 | 3,5-dimethoxystilbene derivative, preparation method and application thereof in anti-drug resistant bacteria |
| CN102161646A (en) * | 2011-03-11 | 2011-08-24 | 华南理工大学 | Stilbene derivative with 1,3,4-oxadiazole and preparation method and application thereof |
| CN102311657A (en) * | 2011-06-25 | 2012-01-11 | 山东大学 | Low-water-solubility fluorescent whitening agent with bactericidal action as well as synthesis method and application thereof |
| CN102408742A (en) * | 2011-09-26 | 2012-04-11 | 山东大学 | Double ether-containing triazinyl stilbene fluorescent whitening agent, its synthesis method and application |
-
2013
- 2013-08-30 CN CN201310390254.4A patent/CN103483328B/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853583A (en) * | 1971-04-12 | 1974-12-10 | T Langstroth | Fluorescent whitening compositions |
| WO1990010001A1 (en) * | 1989-03-01 | 1990-09-07 | Eastman Kodak Company | Process for the preparation of stilbene derivatives |
| CN102001949A (en) * | 2010-10-20 | 2011-04-06 | 华南理工大学 | 3,5-dimethoxystilbene derivative, preparation method and application thereof in anti-drug resistant bacteria |
| CN102161646A (en) * | 2011-03-11 | 2011-08-24 | 华南理工大学 | Stilbene derivative with 1,3,4-oxadiazole and preparation method and application thereof |
| CN102311657A (en) * | 2011-06-25 | 2012-01-11 | 山东大学 | Low-water-solubility fluorescent whitening agent with bactericidal action as well as synthesis method and application thereof |
| CN102408742A (en) * | 2011-09-26 | 2012-04-11 | 山东大学 | Double ether-containing triazinyl stilbene fluorescent whitening agent, its synthesis method and application |
Non-Patent Citations (2)
| Title |
|---|
| 二苯乙烯基苯类荧光增白剂;竹百均，等;《印染助剂》;20060228;第23卷(第2期);第15-18页 * |
| 含1,3,4-噁二唑二苯乙烯衍生物合成、荧光性质及生物活性研究;李新伟;《华南理工大学硕士学位论文》;20130115;第44页表3-2，第22，30-31页，第47页表4-3，4-4 * |
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