CN107245058A - Stilbene-based compound, its intermediate, preparation method and application - Google Patents
Stilbene-based compound, its intermediate, preparation method and application Download PDFInfo
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- CN107245058A CN107245058A CN201710530572.4A CN201710530572A CN107245058A CN 107245058 A CN107245058 A CN 107245058A CN 201710530572 A CN201710530572 A CN 201710530572A CN 107245058 A CN107245058 A CN 107245058A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
-
- 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
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
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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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Coloring (AREA)
Abstract
The invention provides a kind of Stilbene-based compound, its intermediate, preparation method and application.The Stilbene-based compound of the present invention is used as brightening agent, in the pretreatment process of cotton, the whiteness of cotton after processing is higher than market product, washing is faded few, washing fastness is outstanding, and dyeing temperature is 60 DEG C or so, far below the dyeing temperature of conventional fluorescent brightening agent, therefore, it is possible to reduce energy consumption, dyeing cost is reduced.
Description
Technical field
The present invention relates to a kind of Stilbene-based compound, its intermediate, preparation method and application.
Background technology
Fluorescent whitening agent is widely used in the industries such as weaving, papermaking, washing powder, pigment.It is fine that fluorescent whitening agent is applied to cotton
Dimension, is used primarily in the pre-treatment of cotton, the problem of improving cotton whiteness and inadequate vividness.But conventional fluorescent brightening agent is in cotton
Mainly directly combined in the pretreatment process of cloth by brightening agent with fiber, so it is poor often to there is the fastness such as washing
Problem.Therefore, this area needs a kind of new fluorescent whitening agent badly, to solve above-mentioned technical problem.
The content of the invention
The technical problems to be solved by the invention are to overcome existing fluorescent whitening agent in the pretreatment process of cotton,
The whiteness for handling obtained cotton not enough, washes serious, the defect of the bad grade of washing fastness that fades, and there is provided a kind of hexichol second
Ene-type compound, its intermediate, preparation method and application.The Stilbene-based compound of the present invention is as brightening agent, in cotton
Pretreatment process in, the whiteness of the cotton after processing is higher than market product, and washing is faded few, and washing fastness is outstanding, and dyeing
Temperature is 60 DEG C or so, far below the dyeing temperature (generally 98 DEG C or so) of conventional fluorescent brightening agent, therefore, it is possible to reduce energy
Consumption, reduces dyeing cost.
The present invention mainly solves above-mentioned technical problem by the following technical programs.
The invention provides a kind of Stilbene-based compound shown in formula I：
Wherein, R1ForRaAnd RbIt independently is hydrogen, substituted or unsubstituted C1~C4Alkyl or, substitution or not
Substituted phenyl；Described substituted C1~C4Alkyl in substituent refer to be taken by one or more of following groups
Generation：Hydroxyl or carboxyl；Substituent in described substituted-phenyl refers to be replaced by one or more of following groups：-
SO3Na、-COCH3Or halogen；
R2For the structure as shown in Formulas I-a：
Wherein, R3For hydrogen, C1-C4Alkyl,OrN is 1,2 or 3；Represent
Phenyl ring or naphthalene nucleus.
Described substituted or unsubstituted C1~C4Alkyl preferably substituted or unsubstituted methyl, substituted or unsubstituted
Ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted normal-butyl, substitution or not
Substituted isobutyl group or, the substituted or unsubstituted tert-butyl group.
Described halogen preferred F, Cl, Br or I.
Described C1-C4The preferred methyl of alkyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group or the tert-butyl group.
In a preferred embodiment of the invention, R1It is preferred that-N (CH2CH2OH)2、-NHCH2CH2OH、-N(C2H5)2、-
NHCH2COOH、
In a preferred embodiment of the invention, R2It is preferred that following any structure：
Described Stilbene-based compound shown in formula I is preferably following any compound：
Present invention also offers a kind of preparation method of Stilbene-based compound shown in formula I, it includes following step
Suddenly：By the compound and R as shown in Formula II1H carries out following substitution reaction, you can；
Wherein, R1And R2Definition be the same as those described above.
Wherein, the method and condition of described substitution reaction can be the conventional method and condition of the such reaction in this area.
Wherein, described substitution reaction can preferably be carried out in water or under condition of no solvent.Described water and R1H volume mass
Than being preferably 5~10mL/g.Described compound II and R1H mol ratio is preferably 1:2~1:2.2.Described substitution
The pH of reaction is preferably 2.5~5.5.The temperature of described substitution reaction is preferably 80~100 DEG C.Described reaction when
Between preferably with detect reaction complete untill, generally 2~4 hours.
After the completion of reaction, Stilbene-based compound shown in described Formulas I can through oversalting, press filtration and drying process,
It can also be directly spray-dried, obtain the solid of the alkali metal salts such as sodium salt, sylvite or sour form, liquid can also be made
State form.
In the present invention, the compound as shown in Formula II can be made by following methods：By the chemical combination as shown in formula III
Thing and R2H carries out following substitution reaction, you can；
Wherein, R2It is as defined above described.
Wherein, the method and condition of described substitution reaction can be the conventional method and condition of the such reaction in this area.
Wherein, the preferred solvents of described substitution reaction for water.The solvent of described substitution reaction and compound III volume mass
Than being preferably 5~10mL/g.Described compound and R as shown in formula III2H mol ratio is preferably 1:2~1:2.2.
The pH of described substitution reaction is preferably 2.5~5.5.The temperature of described substitution reaction is preferably 25~60 DEG C.It is described
Reaction time preferably with detect reaction complete untill, generally 5~8 hours.
In the present invention, the compound as shown in formula III can be made by following methods：By compound IV and compound
V carries out following substitution reaction, you can；
Wherein, the method and condition of described substitution reaction can be the conventional method and condition of the such reaction in this area.
Present invention also offers a kind of compound as shown in Formula II：
Wherein, group R2It is as defined above described.
Locate present invention also offers a kind of Stilbene-based compound shown in formula I as fluorescent whitening agent before cotton
Improve the application in cotton whiteness and vividness in reason.
Without prejudice to the field on the basis of common sense, above-mentioned each optimum condition, can be combined, and produce the present invention each preferably
Example.
Agents useful for same and raw material of the present invention are commercially available.
The positive effect of the present invention is：The Stilbene-based compound of the present invention is as brightening agent, in cotton
In pretreatment process, the whiteness of the cotton after processing is higher than market product, and washing is faded less, and washing fastness is outstanding, and dyeing temperature
Spend for 60 DEG C or so, far below the dyeing temperature (generally 98 DEG C or so) of conventional fluorescent brightening agent, therefore, it is possible to reduce energy consumption,
Reduce dyeing cost.
Embodiment
The present invention is further illustrated below by the mode of embodiment, but does not therefore limit the present invention to described reality
Apply among a scope.The experimental method of unreceipted actual conditions in the following example, conventionally and condition, or according to business
Product specification is selected.
The compound I-1 of embodiment 1 preparation
Step a)：Prepare compound III
8mL sodium hydroxide solutions (100g/L) are added into 0.01mol 4,4- -2,2 '-disulfonic acid of diaminobenzil
In the 30mL aqueous solution, the pH value for making solution is 7, stand-by.Separately 0.02mol Cyanuric Chlorides (compound V) are beaten in 30mL water,
After after mashing fully, above-mentioned 4,4- diaminobenzil -2 are added thereto, 2 '-sodium disulfonate solution is added for about 1 hour,
Reacted 2~4 hours between pH value 1~7 after adding, obtain compound III crude product.
Step b)：Compound II-1 preparation
By 0.02molR2H-1 10.6mL sodium carbonate liquors (100g/L) dissolve, and the pH value for making solution is 6~7, then,
In the crude product that this solution is added to the compound III-1 obtained by step a), 30~40 DEG C are warming up to, 5~7 hours are incubated, protected
PH value 4~7 is held, compound II-1 crude product is made.
Step c)：Compound I-1 preparation
In the crude product that 0.03mol diethanol amine is added to the compound II-1 obtained by step b), 80~100 are warming up to
DEG C, back flow reaction 4~8 hours in the temperature range, reaction terminates, and in 130~135 DEG C of spray drying, obtains compound I-
1, yield 85%, HPLC purity is about 95%.
It is 1733 to test its molecular weight by HPLC-MS, is consistent with its structure.
Embodiment 2-9
Operated according to the identical of embodiment 1, differ only in the R with corresponding construction2H and R1H, it is as a result as follows：
Effect example
The compound I of synthesis and convenience goods 4BK is subjected to cotton dyeing, and by GB/T 8424.2-2001 and GB/T
The whiteness value and washing fastness of 3921.3-1997 methods describeds test dyed fabric, are contrasted.After dyeing fastness grading according to
Standard GB/T/T 250-2008.
The consumption for synthesizing compound I is 0.3% (o.w.f), and sodium sulphate 20g/L is separately added into after weighing.Dissolving is added
After cotton immersion 5min, dye bath was warming up to 60 degree in 20 minutes, after maintaining 30 minutes, added sodium carbonate 5g/L.Continue to be incubated
30 minutes.Take out cold water wash.
Sell conventional cotton fluorescer 4BK (being purchased from Zhejiang Anoky Additives Co., Ltd.) dyeing consumption 0.3% in market
(o.w.f) sodium sulphate 10g/L, is added after weighing.Dissolving is added after cotton immersion 5min, and dye bath was warming up to 98 in 20 minutes
Degree, continues to be incubated 30 minutes.Take out cold water wash.
The lustful cloth specimen of above-mentioned dye is washed 15 minutes at 95 degree with soaping agent 2g/L.
As can be seen here：The present invention, which obtains a class, can improve the not enough fluorescent whitening agent of prior art, and its whiteness is higher than market
Product, washing is faded less, and washing fastness is outstanding.And due to being contaminated in middle temperature (60 degree), hence it is evident that than the 4BK of 98 degree of high-temperature dyeings
More to save the energy.
Claims (7)
1. a kind of Stilbene-based compound shown in formula I：
Wherein, R1ForRaAnd RbIt independently is hydrogen, substituted or unsubstituted C1~C4Alkyl or, substitution or it is unsubstituted
Phenyl；Described substituted C1~C4Alkyl in substituent refer to be replaced by one or more of following groups：Hydroxyl
Base or carboxyl；Substituent in described substituted-phenyl refers to be replaced by one or more of following groups：-SO3Na、-
COCH3Or halogen；
R2For the structure as shown in Formulas I-a：
Wherein, R3For hydrogen, C1-C4Alkyl,N is 1,2 or 3；Represent phenyl ring
Or naphthalene nucleus.
2. Stilbene-based compound shown in formula I as claimed in claim 1, it is characterised in that
Described substituted or unsubstituted C1~C4Alkyl for substituted or unsubstituted methyl, substituted or unsubstituted ethyl, take
It is generation or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted normal-butyl, substituted or unsubstituted different
Butyl or, the substituted or unsubstituted tert-butyl group；
And/or, described halogen is F, Cl, Br or I；
And/or, described C1-C4Alkyl is methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group or the tert-butyl group.
3. Stilbene-based compound shown in formula I as claimed in claim 1, it is characterised in that
R1For-N (CH2CH2OH)2、-NHCH2CH2OH、-N(C2H5)2、-NHCH2COOH、
And/or, R2For
4. the Stilbene-based compound shown in formula I as described in claim any one of 1-3, it is characterised in that it is such as
Under any compound：
5. a kind of preparation method of Stilbene-based compound shown in formula I as described in claim any one of 1-4, it is special
Levy and be, it comprises the following steps：By the compound and R as shown in Formula II1H carries out following substitution reaction, you can；
Wherein, R1And R2Definition as described in claim any one of 1-4.
6. a kind of compound as shown in Formula II：
Wherein, group R2Definition as described in claim any one of 1-3.
7. a kind of Stilbene-based compound shown in formula I as described in claim any one of 1-4 is used as fluorescent whitening agent
Improve the application in cotton whiteness and vividness in being handled before cotton.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710530572.4A CN107245058A (en) | 2017-07-03 | 2017-07-03 | Stilbene-based compound, its intermediate, preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201710530572.4A CN107245058A (en) | 2017-07-03 | 2017-07-03 | Stilbene-based compound, its intermediate, preparation method and application |
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| CN107245058A true CN107245058A (en) | 2017-10-13 |
Family
ID=60013723
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| CN201710530572.4A Withdrawn CN107245058A (en) | 2017-07-03 | 2017-07-03 | Stilbene-based compound, its intermediate, preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111909536A (en) * | 2020-09-01 | 2020-11-10 | 浙江闰土染料有限公司 | Black direct dye composition, black direct dye and preparation method and application thereof |
| CN112480707A (en) * | 2020-10-30 | 2021-03-12 | 苏州澳缘盛新材料科技有限公司 | Reactive dye yellow and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1133322A (en) * | 1994-06-20 | 1996-10-16 | 希巴-盖吉股份公司 | Azo-dye, preparation process and application thereof |
| CN101735658A (en) * | 2009-11-16 | 2010-06-16 | 天津德凯化工股份有限公司 | Reactive navy blue dye suitable for dyeing nylon and preparation method thereof |
| CN102993111A (en) * | 2011-06-30 | 2013-03-27 | 上海安诺其纺织化工股份有限公司 | Preparation method of 4,4'-diaminostilbene-2,2'-disulfonic acid derivative |
-
2017
- 2017-07-03 CN CN201710530572.4A patent/CN107245058A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1133322A (en) * | 1994-06-20 | 1996-10-16 | 希巴-盖吉股份公司 | Azo-dye, preparation process and application thereof |
| CN101735658A (en) * | 2009-11-16 | 2010-06-16 | 天津德凯化工股份有限公司 | Reactive navy blue dye suitable for dyeing nylon and preparation method thereof |
| CN102993111A (en) * | 2011-06-30 | 2013-03-27 | 上海安诺其纺织化工股份有限公司 | Preparation method of 4,4'-diaminostilbene-2,2'-disulfonic acid derivative |
| CN102993112A (en) * | 2011-06-30 | 2013-03-27 | 上海安诺其纺织化工股份有限公司 | 4,4'-diaminostilbene-2,2'-disulfonic acid derivative |
Non-Patent Citations (3)
| Title |
|---|
| BAKSHI, DAPINDER K. ET AL: "Genotoxicity of Textile Dyes Evaluated with Ames Test and rec-Assay", 《JOURNAL OF ENVIRONMENTAL PATHOLOGY, TOXICOLOGY AND ONCOLOGY》 * |
| 美国化学会: "101453-66-1/RN", 《STNEXT》 * |
| 齐晶晶，等: "三嗪氨基二苯乙烯型荧光增白剂改性及其应用前景", 《化工技术与开发》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111909536A (en) * | 2020-09-01 | 2020-11-10 | 浙江闰土染料有限公司 | Black direct dye composition, black direct dye and preparation method and application thereof |
| CN111909536B (en) * | 2020-09-01 | 2022-04-05 | 浙江闰土染料有限公司 | Black direct dye composition, black direct dye and preparation method and application thereof |
| CN112480707A (en) * | 2020-10-30 | 2021-03-12 | 苏州澳缘盛新材料科技有限公司 | Reactive dye yellow and preparation method and application thereof |
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