CN104744273B - A kind of preparation method of N [2 (2 hydroxyl-oxethyl) 4 nitrobenzophenones] ethanolamine - Google Patents
A kind of preparation method of N [2 (2 hydroxyl-oxethyl) 4 nitrobenzophenones] ethanolamine Download PDFInfo
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Abstract
The present invention relates to a kind of preparation method of N [2 (2 hydroxyl-oxethyl) 4 nitrobenzophenones] ethanolamine, it is with 2 amino 5 nitrophenol as raw material, add hydroxyethylating agent after 2 amino 5 nitrophenol is mixed with alkali and solvent, carry out reacting generation 2 (3 nitro 6 amino-benzene oxygen) ethanol under certain pressure and temp；2 (3 nitro 6 amino-benzene oxygen) ethanol is reacted under catalyst action with ethyl chloroformate again, obtains N [2 (2 hydroxyl-oxethyl) 4 nitrobenzophenones] ethanolamine by condensation, hydrolysis.The present invention has a high income, and purity is high, and quality is good, and production technology is gentle, the advantages of the three wastes produce less；The present invention is not only economic and environment-friendly, and is suitable for industrialized production.
Description
Technical field
The present invention relates to a kind of preparation method of N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine.
Background technology
N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine is a kind of important hair dye intermediate, this product
It is nontoxic, permanent type hair dye intermediate, compared to the wound to human body for the hair dye as intermediate for the p-phenylenediamine is used on market
Evil is little, non-stimulated, and production method has the advantages that low cost, environmental pollution are little.This compound is by Ge great cosmetics company
Using usage amount is in cumulative year after year.But this material how obtaining high-purity high-yield is this production development and extension process
In the difficult problem that runs into.
It is less with regard to preparing the document of N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine method at present,
A kind of synthetic method is reported, the method is to react at ambient pressure, using 2- (3- nitro -6- aminobenzene oxygen in US4337061
Base) ethylate hydrochlorate is raw material, first carries out being acylated protection to amino, then reaction occurs hydroxyl under alkali effect with bromoethanol
Condensation reaction, is sloughed the protection of amino, is finally reacted with bromoethanol again, carry out hydroxyethylation on amino through hydrolysis,
Although patent considers protecting to amino, due to being possible to obtain the material of double hydroxyethyl on amino simultaneously, because
And the product purity that obtained by the method for this patent is relatively low, longer additionally, due to reaction scheme, yield is relatively low, relatively costly.
Content of the invention
In order to overcome the shortcomings of prior art presence, the invention provides one kind prepares N- [2- (2- under conditions of airtight
Hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine method；Using the method controlled syntheses N- [2- (2- hydroxyl-oxethyl) -4-
Nitrobenzophenone] ethanolamine, there is high income, purity is high, production technology is gentle, the three wastes produce less；Solve N- [2- (2- hydroxyl
Base oxethyl) -4- nitrobenzophenone] ethanolamine prepares that yield is low, the low problem of purity.
A kind of preparation method of N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine, comprises the steps：
（1）In certain solvent, after 2- Amino-5-nitrophenol is mixed, add a certain amount of hydroxyethylation examination with alkali
Agent, is reacted under certain pressure and temperature, post-treated obtains 2- (3- nitro -6- amino-benzene oxygen) ethanol；
（2）In certain solvent, 2- (3- nitro -6- amino-benzene oxygen) ethanol is made in catalyst with ethyl chloroformate again
With under reacted, by condensation, obtain N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] second through post processing after hydrolytic process
Hydramine.
Preferably, step（1）In, described solvent is water, DMF, dimethyl acetylamide, dimethyl ether
One of；Described hydroxyethylating agent is one of oxirane, 2- ethyl chloride, 2- bromoethane ethylene chlorhydrin；Described molten
The mass ratio of agent, hydroxyethylating agent and 2- amino -5 nitrophenol is 5～10：0.4～1.2：1.
Preferably, step（1）In, described alkali is solid base, inorganic base or solid base and inorganic base complex, described solid
Body alkali is with aluminium sesquioxide or brucite as carrier, and loads the material of potassium hydroxide or sodium hydroxide；Described inorganic base
It is sodium hydroxide or potassium hydroxide；Described 2- Amino-5-nitrophenol, solid base, the mass ratio of inorganic base are 1：0～0.6：
0～0.8.
Preferably, step（1）In reaction carry out in confined conditions, reaction pressure controls in 0.1～1.0MPa, temperature
Degree controls at 100～145 DEG C.
Preferably, step（1）In, during according to nonaqueous solvent, described post processing is：After reaction completely, reactant liquor is dilute
Release in frozen water, the solid of precipitation obtains 2- (3- nitro -6- amino-benzene oxygen) ethanol through sucking filtration, washing, drying.
Preferably, step（2）In, described solvent is water, glycol dimethyl ether, DMF, dimethyl
One of acetamide, dimethyl ether；The consumption of described solvent is the 5～10 of 2- (3- nitro -6- amino-benzene oxygen) ethanol weight
Times；Described catalyst is one of solid base, Calcium Carbonate, calcium oxide, calcium hydroxide, sodium hydroxide, potassium hydroxide, described solid
Body alkali is with aluminium sesquioxide or brucite as carrier, and loads the material of potassium hydroxide or sodium hydroxide；Described 2- (3- nitre
Base -6- amino-benzene oxygen) ethanol, ethyl chloroformate, catalyst mass ratio be 1：1.0～3.0：0.2～1.5.
Preferably, step（2）Middle reaction is carried out in confined conditions, and reaction pressure controls in 0.1～1.0MPa, condensation
Reaction temperature controls at 60～100 DEG C, and hydrolysising reacting temperature controls at 50～90 DEG C.
Preferably, step（2）In, hydrolytic process carries out or adds aqueous alkali carrying out in condensation reaction solution；Add
Aqueous alkali be potassium hydroxide or sodium hydrate aqueous solution, the weight of 2- (3- nitro -6- amino-benzene oxygen) ethanol and alkali it
Than for 1：0.4～1.5, aqueous alkali mass concentration is 5～25%.
Preferably, step（2）In, when using nonaqueous solvent, post-reaction treatment is：Reaction adds a certain amount of completely afterwards
Water cooling dilution after separate out solid, washing drying obtain N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine, add
The weight of water be 5～10 times of raw material；When adopt use water as solvent when, post-reaction treatment is：Reactant liquor directly filters, water
Wash, dry and obtain N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine.
Preferably, the preparation method of described N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine, including under
State step：
（1）250.0g N,N-dimethylformamide, 25.0g 2- amino -5 nitre is sequentially added in the autoclave of 500ml
Base phenol, 9.6g sodium hydroxide and 19.3g ethylene chlorhydrin, stirring heat up, control pressure in 0.1～1.0MPa, 100～130
DEG C insulation reaction 3～8h；Control raw material HPLC content be less than 1.0%, stopped reaction, after being down to room temperature, reactant liquor is diluted in ice
In water, the solid of precipitation obtains 2- (3- nitro -6- amino-benzene oxygen) ethanol through sucking filtration, washing, drying.
（2）2- (3- nitro -6- amino-benzene oxygen) ethanol 23.2g is added in the autoclave of 500ml, adds
The dimethyl ether of 232.0g, 23.4g ethyl chloroformate and 12.0g Calcium Carbonate, stirring heats up, and control pressure is 0.1～1.0MPa,
In 60～100 DEG C of insulation reaction 4～9 h, the HPLC content of 2- (3- nitro -6- amino-benzene oxygen) ethanol is controlled to be less than 0.5%
When, add mass concentration to be 20% sodium hydrate aqueous solution into reactor, 50～90 DEG C of temperature control, insulation reaction 4～7 h, control
The HPLC content of intermediate be less than 1.0%, stopped reaction, reactant liquor is diluted in analysis of material in 232g water, filter, filter cake through washing, dry
N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine is obtained after dry.
Synthetic route of the present invention is as follows：
The present invention with 2- Amino-5-nitrophenol as raw material, with water or aprotic intensive polar solvent as solvent, airtight
Under the conditions of, add a certain amount of hydroxyethylating agent with compound alkali after 2- Amino-5-nitrophenol is mixed, in certain pressure
With at a temperature of carry out reacting post-treated and obtain 2- (3- nitro -6- amino-benzene oxygen) ethanol；By 2- (3- nitro -6- aminobenzene
Epoxide) ethanol under base catalyst effect with ethyl chloroformate with water or aprotic intensive polar solvent, airtight bar
Part, is reacted under certain pressure, and by condensation, in condensation reaction solution, the aqueous solution of continuation reaction or additional alkali carries out water
Solution reaction and post processing obtain N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine.The method being provided using this invention
Total recovery has reached more than 60%, and it is few to have three wastes, process is simple, catalyst can with recovery, the advantages of consumption of raw materials is little,
There is preferable practicality, through industrial experiment it was demonstrated that the present invention is suitable for industrialized production.
The beneficial effects are mainly as follows：
Method preparation N- [2- (2- the hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine being provided using the present invention has yield
Height, purity is high, and quality is good, and production technology is gentle, the features such as the three wastes produce less, effectively solves N- [2- (2- '-hydroxyethoxy
Base) -4- nitrobenzophenone] ethanolamine prepares that yield is low, and purity is low, a heavy-polluted difficult problem.
Specific embodiment
With reference to specific embodiment, the invention will be further described, but protection scope of the present invention is not limited to this.
Embodiment 1
250.0g DMF, 25.0g is sequentially added in the autoclave of 500ml（0.16mol）2- amino -5 nitrophenol,
9.6g（0.24mol）Sodium hydroxide and 19.3g（0.24mol）Ethylene chlorhydrin, stirring heats up, control pressure in 0.8MPa,
110～120 DEG C of insulation reaction 5h.Sample analysis, control the HPLC content of raw material to be less than 1.0%, i.e. stopped reaction.It is down to room temperature
Afterwards, reactant liquor is diluted in analysis of material in frozen water, and institute's water consumption and thrown DMF are converted into 30% DMF aqueous solution, filter, filter cake is through water
Wash, dry after obtain brown solid 2- (3- nitro -6- amino-benzene oxygen) ethanol 29.9g, HPLC purity 98.2%, yield is
94.3%.
HPLC testing conditions：Shimadzu LC-20AT or the chromatograph of liquid of equal accuracy
Chromatographic column：CLC-ODS-C18（Φ4.6×250mm）
Column temperature：40 DEG C of flow velocitys：1.0 ml/min
Detection wavelength：254 nm sample dissolvings：Mobile phase
Mobile phase：20% methanol buffer
Retention time：Raw material 8.4 min, 2- (3- nitro -6- amino-benzene oxygen) ethanol 14.0 min.
2- (3- nitro -6- amino-benzene oxygen) ethanol 23.2g by above-mentioned gained（0.12mol）It is added to the height of 500ml
In pressure kettle, add the DME of 232.0g, 23.4g（0.16mol）Ethyl chloroformate and 12.0g（0.12mol）Carbonic acid
Calcium, stirring heats up, and control pressure, between 0.7～0.8MPa, in 90～100 DEG C of insulation reaction 6h, sample analysis, controls 2-
Into reactor, when the HPLC content of (3- nitro -6- amino-benzene oxygen) ethanol is less than 0.5%, add the aqueous solution of sodium hydroxide,
The consumption of sodium hydroxide is 4eq, is made into and adds after 20% aqueous solution, temperature control between 50～60 DEG C, insulation reaction 5h,
Sample analysis, control the HPLC content of intermediate to be less than 1.0%, i.e. stopped reaction, and reactant liquor is diluted in a certain amount of water analysis
Expect, institute's water consumption is 10 times of the consumption of 2- (3- nitro -6- amino-benzene oxygen) ethanol, filters, filter cake obtains after washing, drying
To brown solid N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine 24.7g, HPLC purity is 99.4%, and yield is
85.0%.
HPLC testing conditions：Shimadzu LC-20AT or the chromatograph of liquid of equal accuracy
Chromatographic column：CLC-ODS-C18（Φ4.6×250mm）
Column temperature：40 DEG C of flow velocitys：1.0 ml/min
Detection wavelength：254 nm sample dissolvings：Mobile phase
Mobile phase：Methanol：Acetonitrile：Water=1：1：3
Retention time：2- (3- nitro -6- amino-benzene oxygen) ethanol 4.7 min, N- [2- (2- hydroxyl-oxethyl) -4- nitre
Base phenyl] ethanolamine 5.1 min.
Embodiment 2
Solvent DMAC, 50.0g of 250.0g is sequentially added in the autoclave of 1000ml（0.32mol）2- amino -5 nitre
Base phenol, 26.9g（0.48mol）Potassium hydroxide and 38.6g（0.48mol）Ethylene chlorhydrin, stirring heats up, and control pressure exists
Between 0.4～0.5MPa, in 110～120 DEG C of insulation reaction 8h.Sample analysis, control the HPLC content of raw material to be less than 1.0%, that is,
Stopped reaction.After being down to room temperature, reactant liquor is diluted in analysis of material in frozen water, and institute's water consumption and thrown DMAC convert into about 30%
DMAC aqueous solution, filters, and filter cake obtains brown solid 2- (3- nitro -6- amino-benzene oxygen) ethanol after washing, drying
58.9g, HPLC purity 98.9%, yield is 92.9%.
2- (3- nitro -6- amino-benzene oxygen) ethanol 50.3g by above-mentioned gained（0.25mol）It is added to the height of 1000ml
In pressure kettle, add the water of 503.0g, 52.9g（0.37mol）Ethyl chloroformate and 10.1g calcium oxide, stirring heat up,
Control pressure, between 0.5～0.6MPa, in 70～80 DEG C of insulation reaction 8 h, sample analysis, controls 2- (3- nitro -6- amino
Phenoxy group) ethanol HPLC content be less than 0.5% when, into reactor add sodium hydroxide aqueous solution, the consumption of sodium hydroxide
For 4.2eq, add after being made into 15% aqueous solution, temperature control between 50～60 DEG C, insulation reaction 4h, sample analysis, control
The HPLC content of intermediate be less than 1.0%, i.e. stopped reaction, filter, filter cake through washing, dry after obtain brown solid N- [2-
(2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine 49.6g, HPLC purity is 98.4%, and yield is 81.9%.
Embodiment 3
250.0g DMF, 25.0g is sequentially added in the autoclave of 500ml（0.16mol）2- amino -5 nitrophenol,
5.0g solid base（The brucite of load sodium hydroxide）And 19.3g（0.24mol）Ethylene chlorhydrin, stirring heat up, control pressure
Between 0.4～0.5MPa, in 105～110 DEG C of insulation reaction 5h.Sample analysis, control the HPLC content of raw material to be less than 1.0%,
I.e. stopped reaction.After being down to room temperature, reactant liquor is diluted in analysis of material in frozen water, and institute's water consumption and thrown DMF are converted into 30% DMF
Aqueous solution, filters, and filter cake obtains brown solid 2- (3- nitro -6- amino-benzene oxygen) ethanol 29.3g after washing, drying,
HPLC purity 97.6%, yield is 92.4%.
2- (3- nitro -6- amino-benzene oxygen) ethanol 22.3g by above-mentioned gained（0.11mol）It is added to the height of 500 ml
In pressure kettle, add 223.0g（10eq）Water, 23.4g（0.16mol）Ethyl chloroformate and 4.46g solid base, stir
Mix intensification, control pressure between 0.7～0.8MPa, in 80～90 DEG C of insulation reaction 3h, sample analysis, control 2- (3- nitro-
6- amino-benzene oxygen) ethanol HPLC content be less than 0.5% when, into reactor add potassium hydroxide aqueous solution, potassium hydroxide
Consumption be 4eq, be made into and added after 15% aqueous solution, temperature control between 50～60 DEG C, insulation reaction 4h, sample analysis,
Control intermediate HPLC content be less than 1.0%, i.e. stopped reaction, filter, filter cake through washing, dry after obtain brown solid N-
[2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine 22.2g, HPLC purity is 98.1%, and yield is 83.3%.
Embodiment 4
250.0g water, 25.0g is sequentially added in the autoclave of 500ml（0.16mol）2- amino -5 nitrophenol,
9.68g solid base（The brucite of load sodium hydroxide）And 19.3g（0.24mol）Ethylene chlorhydrin, stirring heat up, control pressure
Between 0.2～0.3MPa, in 115～125 DEG C of insulation reaction 8h.Sample analysis, control the HPLC content of raw material to be less than 1.0%,
I.e. stopped reaction.23.4g is added into kettle（0.16mol）Ethyl chloroformate, stirring heats up, control pressure 0.3～
Between 0.4MPa, in 70～80 DEG C of insulation reaction 7h, sample analysis, control 2- (3- nitro -6- amino-benzene oxygen) ethanol
Into reactor, when HPLC content is less than 0.5%, add the aqueous solution of sodium hydroxide, the consumption of sodium hydroxide is 4eq, is joined
Become 20% aqueous solution after add, temperature control between 50～60 DEG C, insulation reaction 6h, sample analysis, control intermediate HPLC contain
Amount be less than 1.0%, i.e. stopped reaction, filter, filter cake through washing, dry after obtain brown solid N- [2- (2- hydroxyl-oxethyl)-
4- nitrobenzophenone] ethanolamine 27.3g, HPLC purity is 98.3%, and yield is 70.4%.
Embodiment 5
Solvent DME, 50.0g of 500.0g is sequentially added in the autoclave of 1000ml（0.32mol）2- amino -5 nitre
Base phenol, 20.0g solid base（The brucite of load potassium hydroxide）And 38.6g（0.48mol）Ethylene chlorhydrin, stirring heat up,
Control pressure between 0.8～0.9MPa, in 110～120 DEG C of insulation reaction 5h.Sample analysis, control the HPLC content of raw material
Less than 1.0%, i.e. stopped reaction.Add 55.8g into kettle（0.39mol）Ethyl chloroformate, stirring heat up, control pressure
Power, between 0.8～0.9MPa, in 70～80 DEG C of insulation reaction 8h, sample analysis, controls 2- (3- nitro -6- amino-benzene oxygen)
When the HPLC content of ethanol is less than 0.5%, temperature control, between 50～60 DEG C, is incubated hydrolysis 6h, sample analysis, controls middle
The HPLC content of body is less than 1.0%, i.e. stopped reaction, and reactant liquor is diluted in analysis of material in frozen water, and institute's water consumption is equivalent with thrown DME
DME aqueous solution for 30%, filters, and filter cake obtains brown solid N- [2- (2- hydroxyl-oxethyl) -4- nitro after washing, drying
Phenyl] ethanolamine 64.1g, HPLC purity is 99.1%, and yield is 82.6%.
Embodiment 6
Solvent DMF, the 50.0g of 500.0g is sequentially added in the autoclave of 1000ml（0.32mol）2- amino -5 nitre
Base phenol, 20.0g solid base（The aluminium sesquioxide of load potassium hydroxide）, 20g potassium hydroxide and 21.14g（0.48mol）Ring
Oxidative ethane, stirring heats up, and control pressure, between 0.9～1.0MPa, in 110～120 DEG C of insulation reaction 5h, sample analysis, is controlled
The HPLC content of raw material processed is less than 1.0%, i.e. stopped reaction.Add 55.8g into kettle（0.39mol）Ethyl chloroformate,
Stirring heats up, and control pressure, between 0.9～1.0MPa, in 80～90 DEG C of insulation reaction 7h, sample analysis, controls 2- (3- nitre
Base -6- amino-benzene oxygen) ethanol HPLC content be less than 0.5% when, temperature control between 50～60 DEG C, be incubated hydrolysis 5h, take
Sample analyze, control intermediate HPLC content be less than 1.0%, i.e. stopped reaction, reactant liquor is diluted in analysis of material in frozen water, water used
Amount and thrown DMF are converted into 30% DMF aqueous solution, filter, and filter cake obtains brown solid N- [2- (2- hydroxyl after washing, drying
Base oxethyl) -4- nitrobenzophenone] ethanolamine 58.3g, HPLC purity is 98.7%, and yield is 75.2%.
Embodiment 7
200.0g water, 25.0g is sequentially added in the autoclave of 500ml（0.16mol）2- amino -5 nitrophenol,
15g sodium hydroxide and 14.2g（0.22mol）Ethyl chloride, stirring heat up, control pressure between 0.6～0.7MPa, 115
～125 DEG C of insulation reaction 7h, sample analysis, control the HPLC content of raw material to be less than 1.0%, i.e. stopped reaction.Add into kettle
26.3g（0.18mol）Ethyl chloroformate, stirring heat up, control pressure between 0.6～0.7MPa, 90～100 DEG C protect
Temperature reaction 5h, sample analysis, when controlling the HPLC content of 2- (3- nitro -6- amino-benzene oxygen) ethanol to be less than 0.5%, to reaction
Add the aqueous solution of sodium hydroxide in kettle, the consumption of sodium hydroxide is 4eq, add after being made into 20% aqueous solution, temperature control is extremely
Between 70～80 DEG C, insulation reaction 5h, sample analysis, control intermediate HPLC content be less than 1.0%, i.e. stopped reaction, mistake
Filter, filter cake obtains brown solid N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine 27.8g after washing, drying,
HPLC purity is 96.8%, and yield is 71.7%.
Claims (1)
1. a kind of preparation method of N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine is it is characterised in that include following
Step：
(1) sequentially add 2- amino -5 Nitrobenzol of 250.0g N,N-dimethylformamide, 25.0g in the autoclave of 500ml
The ethylene chlorhydrin of phenol, 9.6g sodium hydroxide and 19.3g, stirring heats up, and control pressure, in 0.8MPa, is incubated anti-at 110～120 DEG C
Answer 5h, sample analysis, control the HPLC content of raw material to be less than 1.0%, i.e. stopped reaction；After being down to room temperature, reactant liquor is diluted in
Analysis of material in frozen water, institute's water consumption and thrown DMF are converted into 30% DMF aqueous solution,
Filter, filter cake obtains brown solid 2- (3- nitro -6- amino-benzene oxygen) ethanol 29.9g, HPLC purity after washing, drying
98.2%, yield is 94.3%；(2) 2- (3- nitro -6- amino-benzene oxygen) the ethanol 23.2g of above-mentioned gained is added to
In the autoclave of 500ml, add the dimethyl ether of 232.0g, the ethyl chloroformate of 23.4g and the Calcium Carbonate of 12.0g, stirring
Heat up, control pressure between 0.7～0.8MPa, in 90～100 DEG C of insulation reaction 6h, sample analysis, control 2- (3- nitro-
6- amino-benzene oxygen) ethanol HPLC content be less than 0.5% when, into reactor add sodium hydroxide aqueous solution, hydroxide
The consumption of sodium is 4eq, is made into and adds after 20% aqueous solution, temperature control between 50～60 DEG C, insulation reaction 5h, sampling point
Analysis, control intermediate HPLC content be less than 1.0%, i.e. stopped reaction, reactant liquor is diluted in analysis of material in a certain amount of water, used
The water yield is 10 times of the consumption of 2- (3- nitro -6- amino-benzene oxygen) ethanol, filters, and filter cake obtains brown after washing, drying
Solid N- [2- (2- hydroxyl-oxethyl) -4- nitrobenzophenone] ethanolamine 24.7g, HPLC purity is 99.4%, and yield is 85.0%.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4337061A (en) * | 1974-11-05 | 1982-06-29 | Societe Anonyme Dite: L'oreal | Hair dye compositions and new compounds useful therein |
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| US4337061A (en) * | 1974-11-05 | 1982-06-29 | Societe Anonyme Dite: L'oreal | Hair dye compositions and new compounds useful therein |
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| A2和B3型单体缩聚合成超支化偶氮聚氨酯研究;车鹏超等;《高分子学报》;20070131;21-25 * |
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