CN109369437A - Preparation method of antioxidant anti-aging agent N- (4-anilinophenyl) benzamide - Google Patents
Preparation method of antioxidant anti-aging agent N- (4-anilinophenyl) benzamide Download PDFInfo
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- CN109369437A CN109369437A CN201811373201.0A CN201811373201A CN109369437A CN 109369437 A CN109369437 A CN 109369437A CN 201811373201 A CN201811373201 A CN 201811373201A CN 109369437 A CN109369437 A CN 109369437A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
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- C07C231/24—Separation; Purification
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Abstract
The invention relates to the technical field of antioxidant antioxidants, and particularly relates to a preparation method of an antioxidant N- (4-anilinophenyl) benzamide. The method comprises the following steps: preparing an organic solvent, 4-aminodiphenylamine, sodium carbonate and benzoyl chloride according to a weight part ratio, sequentially adding the organic solvent, 4-aminodiphenylamine and sodium carbonate into a reactor with a stirrer, uniformly stirring and mixing, dropwise adding benzoyl chloride in a protective gas atmosphere, heating and stirring for reaction, carrying out reduced pressure distillation to recover the organic solvent, adding purified water-dispersed solid crystals into the solid, filtering, washing, drying and crushing to obtain the N- (4-anilinophenyl) benzamide product. The invention solves the problems of low efficiency and low product purity of the preparation process of the N- (4-anilinophenyl) benzamide. The N- (4-anilinophenyl) benzamide prepared by the method has the advantages of simple and easily obtained raw materials, scientific and reasonable process route, recyclable solvent and small environmental hazard.
Description
Technical field
The present invention relates to antioxygen anti-aging agent technical fields, and in particular to a kind of antioxygen anti-aging agent N- (4- aniiinophenyl) benzene
The preparation method of formamide.
Background technique
Rubber refers to the high elastic polymer material with reversible deformation, at room temperature high resilience, in the external force of very little
Effect is lower to generate larger deformation, remove resilient after external force.Rubber belongs to entirely without styling polymer, its vitrifying
Transition temperature (T g) is low, and molecular weight is often very big, is greater than hundreds of thousands.The rubber of early stage is taken from the plants such as rubber tree, kok-saghyz
Latex, after processing made of with elasticity, insulating properties, impermeable water and air material.Elastomeric high-molecular compound.Point
For natural rubber and two kinds of synthetic rubber.Natural rubber is made of the extraction colloid post-processing from the plants such as rubber tree, kok-saghyz；
Synthetic rubber is then obtained by the aggregated reaction of various monomers.Rubber product is widely used in all aspects of industry or life.
China has been rubber, plastics-production, using processing big country, and in order to make these materials from oxidation, the antioxygen is anti-
Old agent N- (4- aniiinophenyl) benzamide is the anti-aging agent newly developed and N- aromatic substituted acid amide compound amine
One new varieties of anti-aging agent.
Antioxidant is a kind of chemical substance, in the presence of it is only a small amount of in polymeric system, so that it may delay or inhibit poly-
The progress of object oxidation process is closed, to prevent the aging of polymer and prolong its service life, be otherwise known as " anti-aging agent ".Antioxygen
Anti-aging agent various types, the antioxygen anti-aging agent are the amine antioxygen anti-aging agents based on 4-ADPA for parent.
It is both at home and abroad the antioxygen anti-aging agent various types of parent, the common this kind of anti-aging agent in China based on 4-ADPA
There are N, N '-diphenyl-para-phenylene diamine's (antioxidant H), N- isopropyl-N '-diphenyl-para-phenylene diamine (antioxidant 4010NA), N- (1,3
One dimethylbutyl) -4-aminodiphenylamine (antioxidant 4020), N- cyclohexyl-N '-diphenyl-para-phenylene diamine (anti-aging agent
4010), N- (4- aniiinophenyl) Methacrylamide (anti-aging agent NAPM).
These antioxygen anti-aging agents are widely used in rubber and high molecular material, are such as used for rubber, have excellent anti-flexion
Be cracked performance, excellent to heat, oxygen, ozone, light aging protective action.
Many new varieties are had also appeared both at home and abroad based on the antioxygen anti-aging agent that 4-ADPA is parent, and the country is just like N-
(4- aniiinophenyl) acetamide, N- (4- aniiinophenyl) spy are at amide, N- (4- aniiinophenyl) benzamide, N- (4-
Aniiinophenyl) maleimide.Also there is the product of the more extensive more complex series of purposes in foreign countries, such as N- (4- aniline
Base phenyl) -3- [(3- aminopropyl)-(alkyl) amino] butyramide, 3- amino-N- (4- aniiinophenyl)-butyramide,
3- amino-N- (aniiinophenyl)-N- butanamide etc..The knot of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide
Structure formula is as follows:
Summary of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide a kind of antioxygen anti-aging agent N- (4- aniiinophenyl)
The preparation method of benzamide solves antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide preparation process in the prior art
Low efficiency, the problem of product purity is low.
The purpose of the present invention is achieved through the following technical solutions:
A kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, includes the following steps:
Step 1: organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are followed successively by according to weight
80-100 parts, 35-50 parts, 15-22 parts and 30-42 parts preparations, for use；
Step 2: the organic solvent prepared in step 1,4-ADPA and sodium carbonate are sequentially added belt stirrer
Reactor in, be uniformly mixed, be added dropwise chlorobenzoyl chloride in the atmosphere of protection gas, heating stirring reaction is evaporated under reduced pressure back
Organic solvent is received, it is stand-by to obtain solids；
Step 3: purifying water dispersible solid object crystallization, filtering washing 2-3 times, drying is added in the solids into step 2
Crushing up to product is N- (4- aniiinophenyl) benzamide.
The preparation of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, raw material simplicity are easy to get, and process route is scientific and reasonable,
Solvent can be applied repeatedly, and a small amount of three wastes are easily processed, small to environmental hazard.
Antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide provides novel amines antioxidants for rubber industry, mentions
High rubber product quality, improving production efficiency has more choices in the use of anti-aging agent.
Sodium carbonate and pivaloyl chloride can wash removing；During material proportion, the mole of 4-ADPA
Less than chlorobenzoyl chloride, so that 4-ADPA reacts with chlorobenzoyl chloride as far as possible, remaining extra chlorobenzoyl chloride is used
Washing removes, and obtained product purity is high, and purification process is simple.
Further, in the step 1 organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride according to parts by weight
Proportion is followed successively by 90-100 parts, 35-40 parts, 20-22 parts and 40-42 parts.
It is further preferred that organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are according to weight in the step 1
Amount part proportion is followed successively by 100 parts, 35 parts, 22 parts and 42 parts.
Further, the organic solvent is toluene or dichloroethanes；It is nitrogen or helium that gas is protected in the step 2.
It is further preferred that the organic solvent is toluene；It is nitrogen that gas is protected in the step 2.
Further, rate of addition is 5-20ml/min in the step 2, and dropping temperature is 20-30 DEG C；The step
It is 40-45 DEG C, reaction time 3-6h, stirring rate 500-800r/min that reaction temperature is heated in two.
Further, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 40-45 DEG C, and vacuum distillation pressure is
0.60-0.70MPa。
The temperature being added dropwise during the preparation process is controlled in room temperature, low to technique requirement, does not need to carry out under cryogenic
Dropwise addition avoids side reaction from excessively yield being caused to reduce；During the preparation process by vacuum distillation recovered solvent, material utilization is more
Height has saved production cost；The temperature control of vacuum distillation avoids during recycling design that temperature is excessively high to be led in reaction temperature
Cause side reaction.
It is further preferred that the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 45 DEG C, vacuum distillation pressure
Power is 0.70MPa.
Further, it is to carry out fluid-tight using organic solvent that device of air outlet end is protected in the step 2.It had been added dropwise
Cheng Caiyong protection gas is protected, so that side reaction is reduced during being added dropwise, improves yield and purity；It can be produced during dropwise addition
Raw carbon dioxide carries out fluid-tight using organic solvent in the outlet end of protection device of air, it is possible to prevente effectively from the entrance of air,
It is avoided that the possible resorption of other liquid fluid-tights remaining impurity occurs or influences the yield of reaction.
Further, drying temperature is 80-90 DEG C in the step 3, drying time 1-2h.
The beneficial effects of the present invention are:
1. prepared by antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, raw material simplicity is easy to get, and process route science is closed
Reason, solvent can be applied repeatedly, and a small amount of three wastes are easily processed, small to environmental hazard；
Antioxygen anti-aging agent N- 2. (4- aniiinophenyl) benzamide provides novel amines antioxidants for rubber industry,
Rubber product quality is improved, improving production efficiency there are more choices in the use of anti-aging agent；
3. the temperature control being added dropwise during the preparation process in room temperature, technique is required it is low, do not need under cryogenic into
Row, which is added dropwise, avoids side reaction from excessively yield being caused to reduce；Pass through vacuum distillation recovered solvent, material utilization during the preparation process
It is higher, save production cost；The temperature of vacuum distillation is controlled in reaction temperature, avoids temperature during recycling design excessively high
Lead to side reaction；
4. being protected in dropwise addition process using protection gas, so that side reaction is reduced during being added dropwise, yield and pure is improved
Degree；Carbon dioxide can be generated during dropwise addition, and fluid-tight, Ke Yiyou are carried out using organic solvent in the outlet end of protection device of air
Effect avoids the entrance of air, is also avoided that the possible resorption of other liquid fluid-tights remaining impurity occurs or influences the yield of reaction；
5. sodium carbonate and pivaloyl chloride can wash removing；During material proportion, mole of 4-ADPA
Amount is less than chlorobenzoyl chloride, so that 4-ADPA reacts with chlorobenzoyl chloride as far as possible, remaining extra chlorobenzoyl chloride is adopted
Removing is washed with water, obtained product purity is high, and purification process is simple.
Specific embodiment
Technical solution of the present invention is described in further detail combined with specific embodiments below, but protection scope of the present invention is not
It is confined to as described below.
Embodiment 1
A kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, includes the following steps:
Step 1: organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are followed successively by 80 according to weight
Part, 35 parts, 15 parts and 30 parts of preparations, for use；
Step 2: the organic solvent prepared in step 1,4-ADPA and sodium carbonate are sequentially added belt stirrer
Reactor in, be uniformly mixed, be added dropwise chlorobenzoyl chloride in the atmosphere of protection gas, protection device of air outlet end is using having
Solvent carries out fluid-tight, heating stirring reaction, and it is stand-by to obtain solids for vacuum distillation recycling organic solvent；
Step 3: purifying water dispersible solid object crystallization, filtering washing 2 times, ovendry power is added in the solids into step 2
Broken product to obtain the final product is N- (4- aniiinophenyl) benzamide.
Specifically, the organic solvent is toluene；It is nitrogen that gas is protected in the step 2.
Specifically, rate of addition is 5ml/min in the step 2, and dropping temperature is 20 DEG C；It is heated in the step 2
Reaction temperature is 40 DEG C, reaction time 6h, stirring rate 500r/min.
Specifically, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 40 DEG C, and vacuum distillation pressure is
0.70MPa。
Specifically, drying temperature is 80 DEG C in the step 3, drying time 2h.
N- (4- aniiinophenyl) the benzamide fusing point that above-described embodiment is prepared is 160 DEG C, and yield is with 4- amino
The conversion ratio of diphenylamines is calculated as 97%, and appearance is grey powder, purity 99%.
Embodiment 2
A kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, includes the following steps:
Step 1: organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are followed successively by according to weight
100 parts, 35 parts, 22 parts and 42 parts preparations, for use；
Step 2: the organic solvent prepared in step 1,4-ADPA and sodium carbonate are sequentially added belt stirrer
Reactor in, be uniformly mixed, be added dropwise chlorobenzoyl chloride in the atmosphere of protection gas, protection device of air outlet end is using having
Solvent carries out fluid-tight, heating stirring reaction, and it is stand-by to obtain solids for vacuum distillation recycling organic solvent；
Step 3: purifying water dispersible solid object crystallization, filtering washing 3 times, ovendry power is added in the solids into step 2
Broken product to obtain the final product is N- (4- aniiinophenyl) benzamide.
Specifically, the organic solvent is dichloroethanes；It is helium that gas is protected in the step 2.
Specifically, it is 10ml/min that rate of addition, which is rate of addition, in the step 2, and dropping temperature is 30 DEG C；The step
It is 45 DEG C, reaction time 3h, stirring rate 500r/min that reaction temperature is heated in rapid two.
Specifically, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 45 DEG C, and vacuum distillation pressure is
0.65MPa。
Specifically, drying temperature is 90 DEG C in the step 3, drying time 1.5h.
N- (4- aniiinophenyl) the benzamide fusing point that above-described embodiment is prepared is 160 DEG C, and yield is with 4- amino
The conversion ratio of diphenylamines is calculated as 98%, and appearance is grey powder, purity 99%.
Embodiment 3
A kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, includes the following steps:
Step 1: organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are followed successively by 90 according to weight
Part, 40 parts, 20 parts and 40 parts of preparations, for use；
Step 2: the organic solvent prepared in step 1,4-ADPA and sodium carbonate are sequentially added belt stirrer
Reactor in, be uniformly mixed, be added dropwise chlorobenzoyl chloride in the atmosphere of protection gas, protection device of air outlet end is using having
Solvent carries out fluid-tight, heating stirring reaction, and it is stand-by to obtain solids for vacuum distillation recycling organic solvent；
Step 3: purifying water dispersible solid object crystallization, filtering washing 2 times, ovendry power is added in the solids into step 2
Broken product to obtain the final product is N- (4- aniiinophenyl) benzamide.
Specifically, the organic solvent is toluene；It is nitrogen that gas is protected in the step 2.
Specifically, rate of addition is 20ml/min in the step 2, and dropping temperature is 30 DEG C；It is heated in the step 2
Reaction temperature is 40 DEG C, reaction time 5h, stirring rate 700r/min.
Specifically, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 42 DEG C, and vacuum distillation pressure is
0.65MPa。
Specifically, drying temperature is 85 DEG C in the step 3, drying time 1.5h.
N- (4- aniiinophenyl) the benzamide fusing point that above-described embodiment is prepared is 160 DEG C, and yield is with 4- amino
The conversion ratio of diphenylamines is calculated as 97%, and appearance is grey powder, purity 98%.
Embodiment 4
A kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, includes the following steps:
Step 1: organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are followed successively by 95 according to weight
Part, 38 parts, 21 parts and 41 parts of preparations, for use；
Step 2: the organic solvent prepared in step 1,4-ADPA and sodium carbonate are sequentially added belt stirrer
Reactor in, be uniformly mixed, be added dropwise chlorobenzoyl chloride in the atmosphere of protection gas, protection device of air outlet end is using having
Solvent carries out fluid-tight, heating stirring reaction, and it is stand-by to obtain solids for vacuum distillation recycling organic solvent；
Step 3: purifying water dispersible solid object crystallization, filtering washing 3 times, ovendry power is added in the solids into step 2
Broken product to obtain the final product is N- (4- aniiinophenyl) benzamide.
Specifically, the organic solvent is toluene；It is nitrogen that gas is protected in the step 2.
Specifically, rate of addition is 15ml/min in the step 2, and dropping temperature is 20 DEG C；It is heated in the step 2
Reaction temperature is 40 DEG C, reaction time 6h, stirring rate 600r/min.
Specifically, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 42 DEG C, and vacuum distillation pressure is
0.68MPa。
Specifically, drying temperature is 85 DEG C in the step 3, drying time 1.5h.
N- (4- aniiinophenyl) the benzamide fusing point that above-described embodiment is prepared is 160 DEG C, and yield is with 4- amino
The conversion ratio of diphenylamines is calculated as 98%, and appearance is grey powder, purity 99%.
Embodiment 5
A kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, includes the following steps:
Step 1: organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are followed successively by 80 according to weight
Part, 50 parts, 22 parts and 42 parts of preparations, for use；
Step 2: the organic solvent prepared in step 1,4-ADPA and sodium carbonate are sequentially added belt stirrer
Reactor in, be uniformly mixed, be added dropwise chlorobenzoyl chloride in the atmosphere of protection gas, protection device of air outlet end is using having
Solvent carries out fluid-tight, heating stirring reaction, and it is stand-by to obtain solids for vacuum distillation recycling organic solvent；
Step 3: purifying water dispersible solid object crystallization, filtering washing 3 times, ovendry power is added in the solids into step 2
Broken product to obtain the final product is N- (4- aniiinophenyl) benzamide.
Specifically, the organic solvent is toluene；It is nitrogen that gas is protected in the step 2.
Specifically, rate of addition is 20ml/min in the step 2, and dropping temperature is 30 DEG C；It is heated in the step 2
Reaction temperature is 45 DEG C, reaction time 4h, stirring rate 600r/min.
Specifically, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 45 DEG C, and vacuum distillation pressure is
0.70MPa。
Specifically, drying temperature is 90 DEG C in the step 3, drying time 1.5h.
N- (4- aniiinophenyl) the benzamide fusing point that above-described embodiment is prepared is 160 DEG C, and yield is with 4- amino
The conversion ratio of diphenylamines is calculated as 96%, and appearance is grey powder, purity 98%.
The above is only a preferred embodiment of the present invention, it should be understood that the present invention is not limited to described herein
Form should not be regarded as an exclusion of other examples, and can be used for other combinations, modifications, and environments, and can be at this
In the text contemplated scope, modifications can be made through the above teachings or related fields of technology or knowledge.And those skilled in the art institute into
Capable modifications and changes do not depart from the spirit and scope of the present invention, then all should be in the protection scope of appended claims of the present invention
It is interior.
Claims (10)
1. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide, which is characterized in that including walking as follows
It is rapid:
Step 1: organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride are followed successively by 80-100 according to weight
Part, 35-50 parts, 15-22 parts and 30-42 parts of preparations, for use；
Step 2: the organic solvent prepared in step 1,4-ADPA and sodium carbonate are sequentially added the anti-of belt stirrer
It answers in device, is uniformly mixed, chlorobenzoyl chloride, heating stirring reaction are added dropwise in the atmosphere of protection gas, vacuum distillation recycling has
It is stand-by to obtain solids for solvent；
Step 3: purifying water dispersible solid object crystallization, filtering washing 2-3 times, dries pulverizing is added in the solids into step 2
It is N- (4- aniiinophenyl) benzamide up to product.
2. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide according to claim 1,
Be characterized in that, in the step 1 organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride according to weight successively
It is 90-100 parts, 35-40 parts, 20-22 parts and 40-42 parts.
3. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide according to claim 1 or 2,
It is characterized in that, in the step 1 organic solvent, 4-ADPA, sodium carbonate and chlorobenzoyl chloride according to weight according to
Secondary is 100 parts, 35 parts, 22 parts and 42 parts.
4. according to claim 1 or a kind of 2 described in any item systems of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide
Preparation Method, which is characterized in that the organic solvent is toluene or dichloroethanes；It is nitrogen or helium that gas is protected in the step 2
Gas.
5. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide according to claim 4,
It is characterized in that, the organic solvent is toluene；It is nitrogen that gas is protected in the step 2.
6. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide according to claim 1 or 5,
It is characterized in that, rate of addition is 5-20ml/min in the step 2, dropping temperature is 20-30 DEG C；Add in the step 2
Thermal response temperature is 40-45 DEG C, reaction time 3-6h, stirring rate 500-800r/min.
7. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide according to claim 1 or 5,
It is characterized in that, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 40-45 DEG C, vacuum distillation pressure is 0.60-
0.70MPa。
8. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide according to claim 4,
It is characterized in that, the temperature that organic solvent is evaporated under reduced pressure in the step 2 is 45 DEG C, and vacuum distillation pressure is 0.70MPa.
9. a kind of according to claim 1,5,8 described in any item systems of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide
Preparation Method, which is characterized in that it is to carry out fluid-tight using organic solvent that device of air outlet end is protected in the step 2.
10. a kind of preparation method of antioxygen anti-aging agent N- (4- aniiinophenyl) benzamide according to claim 1,
It is characterized in that, drying temperature is 80-90 DEG C in the step 3, drying time 1-2h.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002028820A1 (en) * | 2000-10-05 | 2002-04-11 | Merck Patent Gmbh | Nitroso diphenylamine derivatives |
-
2018
- 2018-11-19 CN CN201811373201.0A patent/CN109369437A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002028820A1 (en) * | 2000-10-05 | 2002-04-11 | Merck Patent Gmbh | Nitroso diphenylamine derivatives |
Non-Patent Citations (3)
| Title |
|---|
| JOHNSON, ROBERT E.ETAL: "Synthesis and antibacterial activity of 1-(arylamino)-1H-pyrroles and 4-(1H-pyrrol-1-ylimino)-2,5-cyclohexadienes", 《JOURNAL OF MEDICINAL CHEMISTRY》, 31 December 1981 (1981-12-31), pages 1314 - 19 * |
| LITVINENKO, L. M. ETAL: "Capacity of the bridge link in binuclear systems for electron-donor conjugation and electron conductivity", 《REAKTSIONNAYA SPOSOBNOST ORGANICHESKIKH SOEDINENII》, 31 December 1968 (1968-12-31), pages 774 - 92 * |
| SHIGEMITSU ETAL: "Antioxidation activities of amine antioxidants substituted with sulfonylamide group for low density polyethylene", 《NIPPON GOMU KYOKAISHI》, 31 December 1995 (1995-12-31), pages 2 * |
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