CN113845469A - Road asphalt light stabilizer and preparation method thereof - Google Patents
Road asphalt light stabilizer and preparation method thereof Download PDFInfo
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- CN113845469A CN113845469A CN202111150362.5A CN202111150362A CN113845469A CN 113845469 A CN113845469 A CN 113845469A CN 202111150362 A CN202111150362 A CN 202111150362A CN 113845469 A CN113845469 A CN 113845469A
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- 239000010426 asphalt Substances 0.000 title claims abstract description 51
- 239000004611 light stabiliser Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 46
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 238000001816 cooling Methods 0.000 claims abstract description 20
- 238000001035 drying Methods 0.000 claims abstract description 20
- 238000001914 filtration Methods 0.000 claims abstract description 20
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 17
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001993 dienes Chemical class 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- 238000004090 dissolution Methods 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000008096 xylene Substances 0.000 claims description 9
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 7
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 239000001110 calcium chloride Substances 0.000 claims description 4
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000002045 lasting effect Effects 0.000 abstract description 2
- 230000006641 stabilisation Effects 0.000 abstract description 2
- 238000011105 stabilization Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000010992 reflux Methods 0.000 description 12
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000002105 nanoparticle Substances 0.000 description 4
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention relates to a road asphalt light stabilizer and a preparation method thereof. Dissolving maleic anhydride into a solvent, continuously stirring, gradually increasing the temperature to 60-90 ℃ after adding conjugated diene, and stirring at constant temperature for 1-3 h to obtain new anhydride. Adding new anhydride into a three-neck flask, adding a solvent, stirring and heating to 60-80 ℃, dropwise adding 2,2,6, 6-tetramethyl-4-piperidinol within 30min, reacting for 2-3 h, cooling to normal temperature, washing for 3 times by using absolute ethyl alcohol, filtering, and drying at 60 ℃ in a vacuum environment to obtain the o-diacid mono-tetramethyl piperidinol ester. Adding o-diacid mono-tetramethyl piperidinol ester into a three-neck flask, adding solid sodium hydroxide and a solvent, gradually heating to 50 ℃, continuously stirring, adding salt after complete dissolution, keeping the temperature and stirring for 1h, cooling to normal temperature, filtering, and drying to obtain a target product, i.e. o-diacid mono-tetramethyl piperidinol ester salt. The invention has lasting and effective light stabilization effect, safe and reliable raw materials, easy preparation control and simple operation.
Description
Technical Field
The invention belongs to the technical field of road materials, and particularly relates to a road asphalt light stabilizer and a preparation method thereof.
Background
The construction of high-grade roads in China tends to be gradually improved, wherein most high-grade pavements select asphalt with relatively better performance as a bonding material. Asphalt is used as a high polymer material mixture, the performance of the asphalt is greatly influenced by the external environment, particularly the influence of ultraviolet rays is most prominent, and particularly, the aging resistance of the asphalt pavement in northwest plateau areas of China is poorer, so that pavement diseases are frequent, and the normal service of the asphalt pavement is seriously influenced. At home and abroad, many research reports on asphalt aging exist, but research and development on asphalt light stabilizers are relatively few, and the following methods are mainly adopted: firstly, the asphalt is modified by adopting the layered montmorillonite, and the method has a certain effect on improving the thermal oxidation and the light stability of the asphalt. But the anti-aging performance of the asphalt is not obviously improved because the asphalt cannot be well and uniformly dispersed in the asphalt; and secondly, the nano material is adopted to modify the asphalt so as to improve the light stability of the asphalt. The method has the advantages that the anti-aging performance of the modified asphalt is improved obviously, but the problems of easy agglomeration and insufficient dispersibility of the nano particles after the nano particles are contacted with the asphalt still exist, and other solvents are mostly needed to dissolve the nano particles firstly or dissolve the nano particles into the asphalt after the surface treatment; thirdly, the existing light stabilizer is adopted to modify the asphalt, and the method has limited effect of improving the light stability of the asphalt and weak pertinence. The main reason is that the existing light stabilizer is widely applied to material systems with fixed molecular structures such as plastics, rubber or textiles, and the system with complex composition such as road asphalt has weak pertinence.
Disclosure of Invention
The invention aims to provide a road asphalt light stabilizer and a preparation method thereof, which aim to solve the problems that in the prior art, ultraviolet rays have great influence on an asphalt pavement, so that pavement diseases are frequent and the normal service of the asphalt pavement is seriously influenced.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a preparation method of a road asphalt light stabilizer comprises the following steps:
(1) dissolving maleic anhydride into a solvent, continuously stirring, adding conjugated diene, gradually increasing the molar ratio of the maleic anhydride to the conjugated diene to 60-90 ℃ at a ratio of 1.02-1.15: 1, stirring at a constant temperature for 1-3 h, cooling to room temperature, filtering, and drying to obtain new anhydride;
(2) adding new anhydride into a three-neck flask, adding a solvent, stirring and heating to 60-80 ℃, dropwise adding 2,2,6, 6-tetramethyl-4-piperidinol within 30min, cooling to normal temperature after reacting for 2-3 h, washing with absolute ethyl alcohol for several times, filtering, and drying at 60 ℃ in a vacuum environment to obtain mono-tetramethyl piperidinol ortho-diacid;
(3) adding o-diacid mono-tetramethyl piperidinol ester into a three-neck flask, adding solid sodium hydroxide and a solvent, gradually heating to 50 ℃, continuously stirring, adding salt after complete dissolution, keeping the temperature and stirring for 1h, cooling to normal temperature, filtering, and drying to obtain a target product, i.e. o-diacid mono-tetramethyl piperidinol ester salt.
In the step (1), the conjugated diene is furan, anthracene, butadiene or isoprene with 4-18 carbon atoms.
In the step (1), the solvent is toluene, xylene, acetone or the like or a mixture thereof.
In the step (2), the solvent is a mixed solution of xylene and N-methylpyrrolidine with a mass ratio of 3: 1.
In the step (3), the solvent is acetone or methanol.
In the step (3), the added salt is chloride, nitrate or acetate containing calcium, magnesium and zinc.
In the step (3), the salt added is calcium chloride.
The road asphalt light stabilizer prepared by the preparation method.
Compared with the prior art, the invention has the following advantages:
1. the road asphalt light stabilizer obtained by the invention is synthesized by adopting raw materials with better asphalt solubility, and simultaneously, chloride, nitrate or acetate containing calcium, magnesium and zinc are added in the preparation process, so that the light stabilizer can be hydrated into organic salt, and the light stabilizer can be uniformly dispersed in asphalt to obtain a lasting and effective light stabilization effect.
2. Aiming at the research of the composition structure of the road asphalt, the invention adopts the raw materials with better asphalt solubility, namely 4-18 carbon conjugated diene and maleic anhydride, and the optically sensitive substance 2,2,6, 6-tetramethyl-4-piperidinol to carry out chemical synthesis, and simultaneously introduces metal ions to prepare the specific organic salt asphalt light stabilizer. The hindered amine structure asphalt light stabilizer can form a stable and uniform blending system with asphalt, so that the light stability of the asphalt is durably and obviously improved. The light stability effect is good, and the aging resistance of the pavement is improved.
3. The preparation method has the advantages of safe and reliable raw materials, easy control of preparation and simple operation. The product of the invention is particularly suitable for being used on asphalt pavements in northwest plateau areas in China, effectively reduces pavement diseases, prolongs the normal service of the asphalt pavements, and has great popularization and application significance.
Detailed Description
The present invention will be described in detail with reference to specific embodiments.
The preparation method of the road asphalt light stabilizer provided by the invention comprises the following three steps of reaction:
example 1: a preparation method of a road asphalt light stabilizer comprises the following steps:
the first step of reaction:
the conjugated diene adopts furan, the molar ratio of maleic anhydride to furan is 1.02:1.0, and the solvent adopts dimethylbenzene.
Adding 20g of maleic anhydride into 250ml of three-neck flask provided with a reflux and stirring device, pouring 100g of dimethylbenzene, continuously stirring, adding 13.6g of furan, gradually raising the temperature to 60 ℃, stirring at constant temperature for 2h, cooling to room temperature, filtering, and drying to obtain the new anhydride.
The second step of reaction:
the molar ratio of the novel acid anhydride to the 2,2,6, 6-tetramethyl-4-piperidinol in the first step is 1.1: 1; xylene and N-methylpyrrolidine are used as solvents according to the mass ratio of 3: 1.
Adding newly prepared 11g of anhydride into a 250ml three-neck flask provided with a reflux and stirring device, adding 100g of mixed solvent, stirring and heating to 60 ℃, dropwise adding 9.4g of 2,2,6, 6-tetramethyl-4-piperidinol within 30min, reacting for 2h, cooling to normal temperature, washing for 3 times by using absolute ethyl alcohol, filtering, and drying at 60 ℃ in a vacuum environment to obtain the o-diacid mono-tetramethyl piperidinol ester.
The third step of reaction:
adding 16g of o-diacid mono-tetramethyl-piperidinol ester into a 100ml three-neck flask provided with a reflux and stirring device, adding 2.1g of solid sodium hydroxide and 40g of methanol, gradually heating to 50 ℃, continuously stirring, adding 2.78g of calcium chloride after complete dissolution, keeping the temperature and stirring for 1h, cooling to normal temperature, filtering, and drying to obtain a target product, i.e. o-diacid mono-tetramethyl-4-piperidinol ester calcium salt.
Example 2
The first step of reaction:
the conjugated diene adopts 1, 3-butadiene, the molar ratio of maleic anhydride to 1, 3-butadiene is 1.08:1.0, and the solvent adopts toluene.
Adding 10.6g of maleic anhydride into 250ml of three-neck flask provided with a reflux and stirring device, pouring 100g of toluene, continuously stirring, adding 5.4g of 1, 3-butadiene, gradually raising the temperature to 60 ℃, stirring at constant temperature for 1h, cooling to room temperature, filtering, and drying to obtain the new anhydride.
The second step of reaction:
the molar ratio of the novel anhydride to 2,2,6, 6-tetramethyl-4-piperidinol in the first step is 1.08: 1; xylene and N-methylpyrrolidine are used as solvents according to the mass ratio of 3: 1.
Adding 9.85g of newly prepared anhydride into 250ml of three-neck flask provided with a reflux and stirring device, adding 100g of mixed solvent, stirring and heating to 60 ℃, dropwise adding 9.4g of 2,2,6, 6-tetramethyl-4-piperidinol within 30min, reacting for 2.5h, cooling to normal temperature, washing for 3 times by using absolute ethyl alcohol, filtering, and drying at 60 ℃ in a vacuum environment to obtain the o-diacid mono-tetramethyl-piperidinol ester.
The third step of reaction: the same as in example 1.
Example 3
The first step of reaction:
the conjugated diene adopts anthracene, the molar ratio of maleic anhydride to anthracene is 1.15:1.0, and the solvent adopts dimethylbenzene.
Adding 11.3g of maleic anhydride into a 250ml three-neck flask provided with a reflux and stirring device, adding 100g of dimethylbenzene, continuously stirring, adding 17.8g of anthracene, gradually raising the temperature to 80 ℃, stirring at constant temperature for 2 hours, cooling to room temperature, filtering, and drying to obtain the new anhydride.
The second step of reaction:
the molar ratio of the novel acid anhydride to the 2,2,6, 6-tetramethyl-4-piperidinol in the first step is 1.12: 1.0; xylene and N-methylpyrrolidine are used as solvents according to the mass ratio of 3: 1.
Adding 18.5g of newly prepared anhydride into a 250ml three-neck flask provided with a reflux and stirring device, adding 100g of mixed solvent, stirring and heating to 70 ℃, dropwise adding 9.4g of 2,2,6, 6-tetramethyl-4-piperidinol within 30min, reacting for 2.5h, cooling to normal temperature, washing for 3 times by using absolute ethyl alcohol, filtering, and drying at 60 ℃ in a vacuum environment to obtain the o-diacid mono-tetramethyl-piperidinol ester.
The third step of reaction:
same as example 1
Example 4
The first step of reaction:
the conjugated diene adopts 2, 4-hexadiene, the molar ratio of maleic anhydride to 2, 4-hexadiene is 1.12:1.0, and the solvent adopts acetone.
Adding 11g of maleic anhydride into a 100ml three-neck flask provided with a reflux and stirring device, adding 40g of acetone, stirring to dissolve, adding 8.2g of 2, 4-hexadiene, gradually raising the temperature to 75 ℃, stirring at a constant temperature for 1.5h, cooling to room temperature, filtering, and drying to obtain the new anhydride.
The second step of reaction:
the molar ratio of the novel acid anhydride to the 2,2,6, 6-tetramethyl-4-piperidinol in the first step is 1.05: 1.0; xylene and N-methylpyrrolidine are used as solvents according to the mass ratio of 3: 1.
Adding 11.3g of newly prepared anhydride into a 250ml three-neck flask provided with a reflux and stirring device, adding 100g of mixed solvent, stirring and heating to 75 ℃, dropwise adding 9.4g of 2,2,6, 6-tetramethyl-4-piperidinol within 30min, reacting for 2h, cooling to normal temperature, washing for 3 times by using absolute ethyl alcohol, filtering, and drying at 60 ℃ in a vacuum environment to obtain the o-diacid mono-tetramethyl piperidinol ester.
The third step of reaction:
adding 16.9 of the o-diacid mono-tetramethyl-piperidinol ester prepared in the previous step into a 100ml three-neck flask provided with a reflux and stirring device, adding 40g of acetone, adding 2.1g of solid sodium hydroxide, continuously stirring, gradually raising the temperature to 50 ℃, adding 2.78g of calcium chloride after complete dissolution, keeping the temperature and stirring for 1h, cooling to the normal temperature, filtering, and drying to obtain the target product, i.e. the o-diacid mono-tetramethyl-4-piperidinol ester calcium salt.
Example 5
The first step of reaction:
the conjugated diene adopts 1, 3-cyclohexadiene, the molar ratio of maleic anhydride to 1, 3-cyclohexadiene is 1.06:1.0, and the solvent adopts acetone.
Adding 10.4g of maleic anhydride into a 100ml three-neck flask provided with a reflux and stirring device, adding 40g of acetone, adding 8.0g of 1, 3-cyclohexadiene while continuously stirring, gradually raising the temperature to 80 ℃, stirring at constant temperature for 3 hours, cooling to room temperature, filtering, and drying to obtain the new anhydride.
The second step of reaction:
the molar ratio of the novel acid anhydride to the 2,2,6, 6-tetramethyl-4-piperidinol in the first step is 1.1: 1.0; xylene and N-methylpyrrolidine are used as solvents according to the mass ratio of 3: 1.
Adding 11.7g of newly prepared anhydride into a 100ml three-neck flask provided with a reflux and stirring device, adding 40g of mixed solvent, stirring and heating to 70 ℃, dropwise adding 9.4g of 2,2,6, 6-tetramethyl-4-piperidinol within 30min, reacting for 2.5h, cooling to normal temperature, washing for 3 times by using absolute ethyl alcohol, filtering, and drying at 60 ℃ in a vacuum environment to obtain the o-diacid mono-tetramethyl-piperidinol ester.
The third step of reaction:
the same as in example 4.
Claims (8)
1. A preparation method of a road asphalt light stabilizer comprises the following steps:
(1) dissolving maleic anhydride into a solvent, continuously stirring, adding conjugated diene, gradually increasing the molar ratio of the maleic anhydride to the conjugated diene to be 1.04-1.15: 1 to 60-90 ℃, stirring at a constant temperature for 1-3 h, cooling to room temperature, filtering, and drying to obtain new anhydride;
(2) adding new anhydride into a three-neck flask, adding a solvent, stirring and heating to 60-80 ℃, dropwise adding 2,2,6, 6-tetramethyl-4-piperidinol within 30min, cooling to normal temperature after reacting for 2-3 h, washing with absolute ethyl alcohol for several times, filtering, and drying at 60 ℃ in a vacuum environment to obtain mono-tetramethyl piperidinol ortho-diacid;
(3) adding o-diacid mono-tetramethyl piperidinol ester into a three-neck flask, adding solid sodium hydroxide and a solvent, gradually heating to 50 ℃, continuously stirring, adding salt after complete dissolution, keeping the temperature and stirring for 1h, cooling to normal temperature, filtering, and drying to obtain a target product, i.e. o-diacid mono-tetramethyl piperidinol ester salt.
2. The method for preparing the road asphalt light stabilizer according to claim 1, wherein in the step (1), the conjugated diene is a conjugated diene with 4-18 carbons such as furan, anthracene, butadiene or isoprene.
3. The method for preparing a road asphalt light stabilizer according to claim 1 or 2, wherein in the step (1), the solvent is toluene, xylene, acetone or a mixture thereof.
4. The method for preparing the road asphalt light stabilizer according to claim 3, wherein in the step (2), the solvent is a mixed solution of xylene and N-methylpyrrolidine with a mass ratio of 3: 1.
5. The method for preparing the road asphalt light stabilizer according to claim 4, wherein in the step (3), the solvent is acetone or methanol.
6. The method for preparing a road asphalt light stabilizer as claimed in claim 5, wherein in the step (3), the added salt is chloride, nitrate or acetate containing calcium, magnesium and zinc.
7. The method for preparing a road asphalt light stabilizer according to claim 6, wherein in the step (3), the salt added is calcium chloride.
8. The road asphalt light stabilizer prepared by the method for preparing the road asphalt light stabilizer according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111150362.5A CN113845469A (en) | 2021-09-29 | 2021-09-29 | Road asphalt light stabilizer and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111150362.5A CN113845469A (en) | 2021-09-29 | 2021-09-29 | Road asphalt light stabilizer and preparation method thereof |
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| US4139520A (en) * | 1975-06-30 | 1979-02-13 | Ciba-Geigy Corporation | Compositions stabilized with hindered piperidine carboxylic acids or metal salts thereof |
| JPH10265458A (en) * | 1997-03-24 | 1998-10-06 | Nippon Shokubai Co Ltd | Production of partial ester of aromatic polycarboxylic acid |
| CN106916335A (en) * | 2016-12-28 | 2017-07-04 | 北京化工大学 | A kind of PVC stabilizer for having light and heat stability concurrently and preparation method thereof |
| CN110527413A (en) * | 2019-09-25 | 2019-12-03 | 广东衡光新材料科技有限公司 | A kind of acrylic acid modified water alcohol acid dispersion and its preparation method and application |
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2021
- 2021-09-29 CN CN202111150362.5A patent/CN113845469A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139520A (en) * | 1975-06-30 | 1979-02-13 | Ciba-Geigy Corporation | Compositions stabilized with hindered piperidine carboxylic acids or metal salts thereof |
| JPH10265458A (en) * | 1997-03-24 | 1998-10-06 | Nippon Shokubai Co Ltd | Production of partial ester of aromatic polycarboxylic acid |
| CN106916335A (en) * | 2016-12-28 | 2017-07-04 | 北京化工大学 | A kind of PVC stabilizer for having light and heat stability concurrently and preparation method thereof |
| CN110527413A (en) * | 2019-09-25 | 2019-12-03 | 广东衡光新材料科技有限公司 | A kind of acrylic acid modified water alcohol acid dispersion and its preparation method and application |
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| K. ALDER，等: "Über die Konstitution der Methyl‐benzol‐tetracarbonsäure aus Ergosterin", CHEMISCHE BERICHTE, vol. 151, no. 08, pages 986 * |
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