CN105254517B - A kind of naphthalene cycle compound and preparation method thereof - Google Patents
A kind of naphthalene cycle compound and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of naphthalene cycle compound and preparation method thereof.The method for preparing azo-compound using the naphthalene cycle compound of the present invention is environmentally friendly, with low cost, and there is excellent washing fastness and higher lifting force using disperse dyes made from described azo-compound, and be dispersed through the requirement that the content of disabling aromatic amine in the cloth specimen after dyeing meets Oeko Tex Standard 100 2015.
Description
Technical field
The present invention relates to a kind of naphthalene cycle compound and preparation method thereof.
Background technology
In recent years, environmental problem is increasingly serious, and country is also more and more stricter to the requirement in terms of environmental protection.Each big city in the whole nation
The existing environmentally friendly sky-high price penalty note of frequency.Meanwhile, as environment increasingly deteriorates, people also gradually pay attention to environmental protection, environmental consciousness
Gradually strengthen, everybody has been basically formed in the whole society and paid attention to ecological environment, feel the well atmosphere preserved the ecological environment.Cause
This, the pressure of current dye industry and dyeing in terms of environmental protection is increasing, and situation is very severe.
Disperse dyes intermediate pollutes all than larger in process of production, and few enterprises can be up to standard and largely produced.Day
Before, because contamination accident takes place frequently, some dyes intermediate famine is directly resulted in, price straight line rises violently, so as to cause to disperse
Also straight line rises suddenly and sharply dyestuff price.Huge cost pressure directly so is produced to dye industry and dyeing.
So, with low cost, environmental friendly, function admirable a disperse dyes kind is dye industry and its market institute
In the urgent need to.
The content of the invention
The technical problems to be solved by the invention be in order to alleviate dye industry and the huge environmental protection pressure of dyeing, into
The problem of this pressure and improvement disperse dyes poor-performing, there is provided a kind of naphthalene cycle compound and preparation method thereof.Utilize this hair
The method that bright naphthalene cycle compound prepares azo-compound is environmentally friendly, with low cost.Using made from the azo-compound of the present invention
Disperse dyes have excellent washing fastness and higher lifting force, and are dispersed through in the cloth specimen after dyeing disabling fragrance
The content of amine meets Oeko-Tex Standard 100-2015 requirement.
The invention provides a kind of azo-compound as shown in Equation 1,
Wherein, R1For C1-4Alkyl or hydrogen；R2For C1-4Alkyl；
D is
Described R1And R2In C1-4Alkyl independently of one another preferred methyl, ethyl, n-propyl, isopropyl, normal-butyl,
Isobutyl group or the tert-butyl group.
Described D is preferredFurther preferably
When described D isWhen, described R1It is preferred that methyl or ethyl.
When described D isWhen, described R1It is preferred that hydrogen, methyl or ethyl.
When described D isWhen, described R1It is preferred that hydrogen, methyl or ethyl.
When described D isWhen, described R1It is preferred that hydrogen, methyl or ethyl.
When described D isWhen, described R1It is preferred that hydrogen, methyl or ethyl.
Described azo-compound preferably is selected from following any compound：
Present invention also offers a kind of preparation method of described azo-compound, it comprises the following steps：In a solvent,
Under conditions of acid is present, compound 3 and naphthalene cycle compound 2 are subjected to coupling reaction, you can,
Wherein, A is Cl-、CH2COO-、H2PO4 -、HSO4 -Or NO3 -。
In the preparation method of described azo-compound, described coupling reaction refers to the diazol (chemical combination of primary aromatic amine
Thing 3) reaction for generating azo-compound (compound 1), its specific reactions steps and bar are reacted with arylamine (naphthalene cycle compound 2)
Part can refer to such reaction in this area and be selected.
In the preparation method of described azo-compound, described solvent is the Conventional solvents of the such reaction in this area, excellent
Elect water as.
In the preparation method of described azo-compound, preferably 0 DEG C~5 DEG C of the reaction temperature of described coupling reaction.
In the preparation method of described azo-compound, in described acid preferably hydrochloric acid, acetic acid, phosphoric acid, nitric acid and sulfuric acid
One or more, the one or more in further preferred hydrochloric acid, acetic acid and sulfuric acid, still further preferably sulfuric acid and/or salt
Acid.
In the preparation method of described azo-compound, described sour volume ratio preferably 0.033 with described solvent~
0.042∶1。
In the preparation method of described azo-compound, the volume mass of described solvent and described naphthalene cycle compound 2
Than preferred 6mL/g.
In the preparation method of described azo-compound, described naphthalene cycle compound 2 and the mol ratio of compound 3 preferably 1.1
~1.2: 1.
In the preparation method of described azo-compound, the process of described coupling reaction can use conventional in this area
Monitoring method is monitored (such as filter paper oozes circle method), will typically react liquid spotting on filter paper, then point one drips beside sampling point
The solution of naphthalene cycle compound 2 is oozed with both and not developed the color for reaction end at circle common factor.Wherein, (described " naphthalene cycle compound 2
Solution " be using the solvent conventional in the art that naphthalene cycle compound 2 can be dissolved by naphthalene cycle compound 2 dissolve obtain it is molten
Liquid), the reaction time preferred 2h of the coupling reaction.
In the preparation method of described azo-compound, described coupling reaction can also be post-processed after terminating to product
Product is further purified.Described post processing preferably includes following steps：Reaction solution is cooled to after room temperature and filtered, filter cake water
Dried after washing, that is, obtain described azo-compound.Preferably 50~70 DEG C of described drying temperature.
In the preparation method of described azo-compound, the preparation method of described compound 3 may include following steps：Nothing
Under solvent condition, under conditions of acid is present, nitrosyl sulfuric acid and compound 8 are subjected to diazo-reaction, described change is obtained
Compound 3, you can,
Described diazo-reaction refers to primary aromatic amine (compound 8) and nitrosyl sulfuric acid under strong acid media, effect life
Into the reaction of diazol (compound 3), its specific reactions steps and condition can refer to the conventional choosing of such reaction in this area
Select.
In described diazo-reaction, the one or more in described acid preferably hydrochloric acid, acetic acid and sulfuric acid are further excellent
Select sulfuric acid.
In described diazo-reaction, the mol ratio of described compound 8 and described nitrosyl sulfuric acid is preferably 1: 1~
1.1。
In described diazo-reaction, the quality mol ratio of described sour and described compound 8 is 280: 1.
Preferably 10~20 DEG C, such as 15 DEG C of the reaction temperature of described diazo-reaction.
In described diazo-reaction, preferably by it is described it is sour mixed with described nitrosyl sulfuric acid after, then with it is described
The hybrid reaction of compound 8, you can.
In described diazo-reaction, described " being mixed with described compound 8 " is to delay described compound 8 excellently
Slow to be added in described " the described sour mixed liquor with described nitrosyl sulfuric acid ", the described time being slowly added to is 1
~1.5h.
The process of described diazo-reaction can be supervised by routine monitoring method in this area (such as TLC or HPLC)
Survey, as reaction end when typically being disappeared using described compound 8.Reaction time preferred 3h~4h of described diazo-reaction.
Described diazo-reaction is preferably directly used in the system of described azo-compound without post processing after terminating
In standby.
In the preparation method of described azo-compound, the preparation method of described naphthalene cycle compound 2 may include following step
Suddenly：Compound 4 is reacted with compound 5, described naphthalene cycle compound 2 is obtained, you can；
In the preparation method of described naphthalene cycle compound 2, specific reactions steps and condition can refer to such in this area
The conventional selection of reaction.
In the preparation method of described naphthalene cycle compound 2, described reaction can be solvent-free or under conditions of having a solvent
Carry out, preferably carry out in the absence of a solvent.
It is described when described reaction is being carried out under having solvent condition in the preparation method of described naphthalene cycle compound 2
Solvent is the conventional use of solvent of such reaction of this area, preferably absolute ethyl alcohol.Described solvent and described compound 4
Volume mass is than preferred 1.31mL/g.
In the preparation method of described naphthalene cycle compound 2, described reaction is preferably carried out in the presence of an inorganic base, described
Inorganic base such can react conventional use of inorganic base, preferably sodium hydroxide, potassium hydroxide, potassium carbonate, carbonic acid for this area
One or more in hydrogen sodium, saleratus and sodium carbonate, further preferred natrium carbonicum calcinatum.
In the preparation method of described naphthalene cycle compound 2, when adding inorganic base, described inorganic base and described chemical combination
The mol ratio of thing 4 preferably 0.5~0.6: 1.
In the preparation method of described naphthalene cycle compound 2, described reaction is carried out preferably under the catalytic action of catalyst,
Described catalyst is the conventional catalyst of such reaction in this area, preferably sodium bromide and/or KI.
In the preparation method of described naphthalene cycle compound 2, when adding catalyst, described catalyst and described chemical combination
The mol ratio of thing 4 preferably 0.22~0.26: 1.
In the preparation method of described naphthalene cycle compound 2, the mol ratio of described compound 4 and described compound 5 is excellent
Select 1: 1.3~1.5.
In the preparation method of described naphthalene cycle compound 2, preferably 100 DEG C~120 DEG C of described reaction temperature.
The preparation method of described naphthalene cycle compound 2, after inorganic base and catalyst is added, preferably incite somebody to action " compound 4,
The mixture of inorganic base and catalyst ", which is added in compound 5, to be reacted.
In the preparation method of described naphthalene cycle compound 2, the reaction process of the reaction can be by conventional in this area
Monitoring method (such as TLC or HPLC) be monitored, as reaction end when typically being disappeared using described compound 4.
In the preparation method of described naphthalene cycle compound 2, described reaction may also include following last handling process after terminating：
Added water into reaction solution, be warming up to 70 DEG C and be layered while hot, collect organic phase, added water after regulation PH at room temperature to neutrality, heating
To 65~70 DEG C, it is layered while hot, collects organic phase, be evaporated, you can.In the last handling process of the reaction, preferably with 30%
The aqueous solution regulation PH of sodium hydroxide.
Present invention also offers a kind of naphthalene cycle compound 2,
Wherein, R1And R2It is as defined above described.
Described naphthalene cycle compound 2 preferably is selected from following any compound：
Present invention also offers a kind of preparation method of described naphthalene cycle compound 2, it comprises the following steps：By compound
4 are reacted with compound 5, obtain described naphthalene cycle compound 2, you can；
Its condition reacted and step are same as above.
Present invention also offers a kind of application of described azo-compound in stamp and/or dyeing.
Described application, is preferably the stamp to fabric and/or dyeing.
In the preferred acetate fiber of described fabric, Fypro, polyester fiber and polyester fiber blend fibre product
One or more, more preferably polyester fiber and/or polyester fiber blend fibre product.
Described polyester fiber blend fibre product refers to the natural fibers such as polyester fiber and cotton, hair, silk or fiber crops and mixes spinning
The product being made.
The preferred pet fiber of described polyester fiber.
The described preferred polyester/cotton blend fibre product of polyester fiber blend fibre product or polyester/wool blend fibre
Product.
Described polyester/cotton blend fibre product refers to the textile fabrics that polyester fiber is made with cotton fiber mix spinning.
Described polyester/wool blend fibre product refers to the weaving system that polyester fiber is made with wool fiber mix spinning
Product.
Described polyester fiber and the existence form of polyester fiber blend fibre product being conventionally present for this area
Form, preferably fiber, yarn, woven fabric, knitted fabric or non-woven fabric.
Described application, it preferably includes following steps；By described azo-compound according to this area conventional treatment side
Method (as being sanded) progress handles and obtains disperse dyes, is then used in stamp and/or the dyeing of the fabric.
Described application, it is more preferably further comprising the steps of：(1) it is described azo-compound is conventional according to this area
Processing method (as being sanded) progress handles and obtains disperse dyes；(2) described disperse dyes are mixed with water, in acid condition
Under, 70 DEG C are warming up to, fabric is put into, temperature is risen to 130 DEG C in 30 minutes, 50 minutes is incubated, is cooled to 90 DEG C, you can.
In described application, described acid condition is preferably adjusted by acetic acid, pH value preferably 4~5.
In described application, after the cooling, reduction clearing step is may also include, is preferably included：Fabric is put into and contained
In the aqueous solution for having 1 g/l of sodium hydroxide and 3 g/l of dithionic acid disodiums, cleaned at 80 DEG C, the time is 20 minutes.Institute
The consumption for the aqueous solution containing 1 g/l of sodium hydroxide and 3 g/l of dithionic acid disodiums stated is not particularly limited, as long as general
The described fabric of submergence is cleaned, you can.
Room temperature in the present invention is 10 DEG C~30 DEG C.
Number in the present invention refers both to mass fraction unless otherwise specified.
Agents useful for same and raw material of the present invention are commercially available.
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.
The positive effect of the present invention is：The method ring of azo-compound is prepared using the naphthalene cycle compound of the present invention
Protect, it is with low cost.There is excellent washing fastness and higher using disperse dyes made from the azo-compound of the present invention
Lifting force, and be dispersed through in the cloth specimen after dyeing disable aromatic amine content meet Oeko-Tex Standard 100-
2015 requirement.
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.
Heretofore described LC-MS data be by Waters UPLC-SQD LC-MSs instrument (mobile phase be acetonitrile/
Aqueous systems, 60%-90% acetonitrile V/V, 40 DEG C of column temperature) test gained.
HPLC of the present invention test condition is：Methanol: water (V/V)=40: 60, flow velocity：1ml/min, detects ripple
It is long：254nm.
Naphthalene cycle compound 2-1 (the R of embodiment 11For hydrogen, R2For methyl) preparation
Under room temperature condition, 21.7g methyl chloroacetate (compounds 5, R are added in the 100ml three-necked flasks dried2For
Methyl), 19.09g naphthalidines, 8.5g natrium carbonicum calcinatums and 3.46g sodium bromides are then added in stirring, is stirred, then
It is to slowly warm up to 100 DEG C of insulation reactions.HPLC monitoring reaction is until naphthalidine reaction is complete.Adding about 70ml water makes solid molten
Solution, be to slowly warm up to 70 DEG C and be layered while hot, collect organic phase, add water 50ml, at room temperature with 30% sodium hydrate aqueous solution
PH is adjusted to neutrality, 70 DEG C is then to slowly warm up to, is layered while hot, organic phase is collected, vacuum distillation removes moisture, obtains naphthalene nucleus
Compound 2-1 (R1For hydrogen, R2For methyl) 27.35g, yield 95.3%, the purity that HPLC is determined is 96.5%, LC-MS measure naphthalene nucleus
Compound 2-1 (R1For hydrogen, R2For methyl) result be [M+H]+216.3, [M+Na]+238.4。
Naphthalene cycle compound 2-4 (the R of embodiment 21For methyl, R2For ethyl) preparation
Under room temperature condition, 24.51g ethyl chloroacetate (compounds 5, R are added in the 100ml three-necked flasks dried2For
Ethyl), 24.19g N- methyl naphthalidine, 8.5g natrium carbonicum calcinatums and 3.46g sodium bromides are then added in stirring, stirring is equal
It is even, then it is to slowly warm up to 120 DEG C of insulation reactions.HPLC monitoring reaction is until the reaction of N- methyl naphthalidine is complete.Add about
70ml water makes solid dissolving, is to slowly warm up to 70 DEG C and is layered while hot, collects organic phase, 50ml is added water, at room temperature with 30%
Sodium hydrate aqueous solution adjusts PH to neutrality, is then to slowly warm up to 65 DEG C, is layered while hot, collects organic phase, and vacuum distillation is removed
Moisture is removed, naphthalene cycle compound 2-4 (R are obtained1For methyl, R2For ethyl) 35.14g, yield 94%, HPLC determine purity be
94.9%, LC-MS determine naphthalene cycle compound 2-4 (R1For methyl, R2For ethyl) result be [M+H]+244.4, [M+Na]+
266.3。
Naphthalene cycle compound 2-6 (the R of embodiment 31For ethyl, R2For ethyl) preparation
Under room temperature condition, 30ml absolute ethyl alcohols, 21.26g ethyl chloroacetates are added in the 100ml four-hole boiling flasks dried
(compound 5, R2For ethyl), 22.83g N- ethyls naphthalidine, 8.5g natrium carbonicum calcinatums and 3.46g are then added in stirring
Sodium bromide, stirs, and is then to slowly warm up to 100 DEG C of backflow insulation reactions.HPLC monitoring reactions are until N- ethyl naphthalidines
Reaction is complete.Room temperature is cooled to, vacuum distillation removes ethanol and excessive ethyl chloroacetate.Adding about 70ml water makes solid molten
Solution, be to slowly warm up to 70 DEG C and be layered while hot, collect organic phase, add water 50ml, at room temperature with 30% sodium hydrate aqueous solution
PH is adjusted to neutrality, 70 DEG C is then to slowly warm up to, is layered while hot, organic phase is collected, vacuum distillation removes moisture, obtains naphthalene nucleus
Compound 2-6 (R1For ethyl, R2For ethyl) 27.5g, yield 80.15%, the purity that HPLC is determined is 91.3%, LC-MS measure naphthalenes
Cycle compound 2-6 (R1For ethyl, R2For ethyl) result be [M+H]+258.1, [M+Na]+280.3。
Method according to embodiment 1-2 prepares naphthalene cycle compound 2-1~2-6, its relevant experimental data and Structural Identification number
According to being shown in Table 1.
The naphthalene cycle compound 2-1 of table 1~2-6 experimental data and Structural Identification data
Azo-compound 1-3 (the R of embodiment 41For methyl, R2It is for methyl, D) preparation
Under room temperature condition, in the 100ml three-necked flasks dried, 11.2g 98% sulfuric acid, 13.34g 40% is added
Nitrosyl sulfuric acid sulfuric acid solution, ice bath is cooled to 10-15 DEG C after stirring, and is slowly added to 7.32g 2,4- dinitro benzenes
Amine, about adds 1h, and being incubated 3h under the conditions of 10-15 DEG C after adding obtains transparent diazo liquid.Then equipped with 60ml water, the sulphur of 2ml 98%
In in 1h in the 2000ml beakers of acid, progress is added dropwise in obtained diazo liquid and 10.05g naphthalene cycle compounds 2-3 simultaneously and is coupled instead
Should, 0-5 DEG C of controlling reaction temperature on the rocks, and 2h completion couplings are incubated at 0-5 DEG C, stir to room temperature, filter naturally, washing, 50
DEG C drying, obtains azo-compound 1-3 dyestuff filter-cakes 21.3g, yield 92.37%, the purity 94.5% of HPLC tests.LC-MS
The result for determining azo-compound -13 is [M+H]+424.4, [M+Na]+446.6。
Azo-compound 1-8 (the R of embodiment 51For hydrogen, R2It is for ethyl, D) preparation
Under room temperature condition, in the 100ml three-necked flasks dried, 11.2g 98% sulfuric acid, 12.7g 40% is added
The sulfuric acid solution of the nitrosyl sulfuric acid of (0.04mol), ice bath is cooled to 10-15 DEG C after stirring, and is slowly added to 10.48g 2,
The bromaniline of 4- dinitros -6 (0.04mol), about adds 1-1.5h, and 4h is incubated under the conditions of being warming up to 15-20 DEG C after adding and obtains transparent heavy
Nitrogen liquid.Then in equipped with 60ml water, the 2000ml beakers of 2.5ml98% sulfuric acid in 1h with 10.47g naphthalene cycle compounds 2-2
Dropwise addition simultaneously carries out coupling reaction, 0-5 DEG C of controlling reaction temperature on the rocks, and is incubated 2h completion couplings at 0-5 DEG C, stirs naturally extremely
Room temperature, is filtered, washing, 70 DEG C of drying, obtains azo-compound 1-8 dyestuff filter-cakes 18.84g, yield 93.8%, HPLC tests
Purity 96.2%.The result that LC-MS determines azo-compound 1-8 is [M+H]+503.3, [M+Na]+525.2。
According to the method for embodiment 1~5, reactant is correspondingly replaced, azo-compound 1-1~1-30 is prepared.It is related real
Test data and Structural Identification data are shown in Table 2.
The azo-compound 1-1 of table 2~1-30 experimental data and Structural Identification data
Effect example 1
Take 5 grams of azo-compound 1-3 (R as made from embodiment 21For methyl, R2For methyl, D is
), commodity disperse dye is made after grinding, the disperse dyes prepared are dispersed in 500 milliliters of water, draw 20 milliliters with
80 milliliters of water mixing, adjusts dye bath pH to be 4~5, is warming up to 70 DEG C and is dyed while being put into 5 grams of polyester fiber cloths with acetic acid,
In being warming up to 130 DEG C in 30 minutes by 70 DEG C, 50 minutes are incubated, less than 90 DEG C draining cleanings are cooled to.Cloth specimen is put into again and contained
Cleaned in 100 milliliters of reduction cleaning aqueous solution for having 1 g/l of sodium hydroxide and 3 g/l of sodium dithionites in 80 DEG C,
Time is 20 minutes.
Effect example 2
Azo-compound 1-1~1-30 disperse dyes prepared are dyed according to the method for effect example 1, and adopted
Tested respectively with national standard GB/T 3921-2008 [C (3) method], GB/T 2394-2013, GB/T 2397-2012 its washing fastness,
Staining power and lifting force.And its disabling aromatic amine is tested using Oeko-Tex Standard 100-2015 to dyeing cloth specimen
Content, its test result is shown in Table 3 and table 4.
Washing fastness effect data after the dyeing of disperse dyes prepared by -1~1-30 of azo-compound of table 3
Note：In addition to 2- naphthylamines, remaining disabling aromatic amine is not detected.
The data display of table 3：Disperse dyes of the present invention, not only with higher washing fastness, can effectively solve water
Wash the problem of fastness is poor；And cloth specimen disabling aromatic amine meets Oeko-Tex after disperse dyeing of the present invention
It is less than 20mg/kg requirement in Standard 100-2015.
The lifting force of disperse dyes prepared by the azo-compound 1-1 of table 4~1-30
The data display of table 4：Disperse dyes of the present invention have excellent lifting force.
Contrast on effect example 1
Method of testing according to effect example 2 test respectively C.I. disperse reds 6 and C.I. disperse blues 85 washing fastness,
Staining power and lifting force.Its test result is shown in Table 5.
(C.I. disperse reds 6)
(C.I. disperse blues 85)
Table 5.C.I. disperse reds 6 and the wash water fastness of C.I. disperse blues 85 and lifting force
The data display of table 5：C.I. the washing fastness of disperse red 6 and C.I. disperse blues 85 is below disperse dyes of the present invention
Washing fastness；Lifting force is also far away from the lifting force of disperse dyes of the present invention.
Claims (6)
1. a kind of naphthalene cycle compound 2,
Wherein, R1For C1-4Alkyl or hydrogen；R2For C1-4Alkyl；Described R1And R2In C1-4Alkyl be each independently
Methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group or the tert-butyl group；
Described naphthalene cycle compound 2 is not
2. naphthalene cycle compound 2 as claimed in claim 1, it is characterised in that：Described naphthalene cycle compound 2 is selected from following anyization
Compound：
3. the preparation method of naphthalene cycle compound 2 as claimed in claim 1 or 2, comprises the following steps：By compound 4 and chemical combination
Thing 5 is reacted, and obtains described naphthalene cycle compound 2, you can；
4. the preparation method of naphthalene cycle compound 2 as claimed in claim 3, it is characterised in that：
Described reaction is solvent-free or have progress under conditions of solvent；
And/or, described reaction is to carry out in the presence of an inorganic base, and described inorganic base is sodium hydroxide, potassium hydroxide, carbon
One or more in sour potassium, sodium acid carbonate, saleratus and sodium carbonate；
And/or, described reaction is carried out under the catalytic action of catalyst, and described catalyst is sodium bromide and/or iodate
Potassium；
And/or, described compound 4 and the mol ratio of described compound 5 are 1：1.3~1.5；
And/or, the reaction temperature of the reaction is 100 DEG C~120 DEG C.
5. the preparation method of naphthalene cycle compound 2 as claimed in claim 4, it is characterised in that：
When described reaction is being carried out under conditions of having solvent, described solvent is absolute ethyl alcohol；Described solvent and institute
The volume mass ratio for the compound 4 stated is 1.31mL/g；
And/or, described inorganic base is natrium carbonicum calcinatum；
And/or, described inorganic base and the mol ratio of described compound 4 are 0.5~0.6：1；
And/or, described catalyst and the mol ratio of described compound 4 are 0.22~0.26：1.
6. the preparation method of naphthalene cycle compound 2 as claimed in claim 3, it is characterised in that including following last handling process：To
Added water in reaction solution, be warming up to 70 DEG C and be layered while hot, collect organic phase, added water and, to neutrality, be warming up to after regulation PH at room temperature
65~70 DEG C, it is layered while hot, collects organic phase, be evaporated, you can.
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| US20030082547A1 (en) * | 2001-08-27 | 2003-05-01 | Ewing Gregory J. | Non-fluorescent quencher compounds and biomolecular assays |
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