CN108929237A - A kind of new liquid antioxidant and preparation method thereof - Google Patents
A kind of new liquid antioxidant and preparation method thereof Download PDFInfo
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- CN108929237A CN108929237A CN201810660889.4A CN201810660889A CN108929237A CN 108929237 A CN108929237 A CN 108929237A CN 201810660889 A CN201810660889 A CN 201810660889A CN 108929237 A CN108929237 A CN 108929237A
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- 0 *c1cc(CCC(OCCN(*)CCOC(CCc(cc2*)cc(I)c2O)=O)=O)cc(*)c1O Chemical compound *c1cc(CCC(OCCN(*)CCOC(CCc(cc2*)cc(I)c2O)=O)=O)cc(*)c1O 0.000 description 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/10—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of a carbon skeleton containing rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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- 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
- C08K5/17—Amines; Quaternary ammonium compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of Liquid hindered phenol antioxidants, for the degradation problem of high molecular material in the process of processing and using, have the technical effect that dosage is few, antioxidant effect is good, reduces manipulation strength and environmental pollution.The general formula of molecular structure of the oxidant isWherein R1、R2It respectively can be hydrogen atom, the straight chain containing 1~6 carbon atom or the branched alkyl containing 3~6 carbon atoms, R3For the linear or branched alkyl group containing 2~18 carbon atoms.The compound for being 2.0~2.5:1 by molar ratioIt is being made with catalyst full of inert gas, vacuum degree of heating generation esterification in the confined reaction of 120mmHg to 2mmHg.Liquid-type hindered phenol antioxidant prepared by the present invention, convenient transportation, antioxygenic property is excellent, can be used in the high molecular materials such as lubricating oil, polyurethane, polyolefin, can significantly improve Polymer Processing stability and long-acting antioxygenic property.
Description
Technical field
The present invention relates to a kind of new liquid antioxidant and preparation method thereof, belong to technical field of fine.
Background technique
High molecular material can degrade in its processing and use process because of factors such as light, heat, and antioxidant is high score
The auxiliary agent being most widely used in sub- material has application in each stage of high molecular material life cycle.Currently on the market
Antioxidant mainly based on solid powdery, there is dust pollution, transport measuring difficulties in use in powdered antioxidant
The disadvantages of, especially powdered antioxidant is used for mixing difficulty, liquid antioxidant when liquid product has compared with powder antioxidant
Unique advantage, liquid antioxidant is easy to use, dosage is few, antioxidant effect is good, and can be reduced operation labor intensity and environment dirt
Dye, is especially widely used in the high molecular materials such as oil product, polyurethane, polyolefin.
A kind of preparation method of antioxidant 5057 is provided in patent CN103709046A, the antioxidant 5057 is
A kind of aromatic amine liquid antioxidant provides a kind of preparation side of liquid antioxidant 1135 in patent CN102030647A
Method, described in antioxidant 1135 be a kind of Hinered phenols liquid antioxidant, aforesaid liquid antioxidant lubricating oil, polyurethane,
Polyolefin etc. all has good application effect.
Summary of the invention
The first object of the present invention is to provide a kind of new liquid antioxidant, is a kind of Hinered phenols antioxidant, existing
The convenience that excellent antioxygenic property has liquid antioxidant available pump to convey again, is a kind of performance suitable for various polymer
Excellent liquid antioxidant can be used in the high molecular materials such as lubricating oil, polyurethane, polyolefin, can significantly improve polymer
Processing stability and long-acting antioxygenic property.
Second purpose of the invention is to provide the preparation method of aforesaid liquid antioxidant.
Third purpose of the present invention is to provide the purposes of aforesaid liquid antioxidant in the polymer.
Technical scheme is as follows:
The present invention provides a kind of new liquid antioxidant, the structure of compound I are as follows:
The present invention also provides the preparation methods of above-mentioned new liquid antioxidant, carry out ester using compound ii and compound III
New liquid antioxidant of the invention to obtain the final product is reacted in change, wherein compound ii structure are as follows:
The structure of compound III are as follows:
Ester exchange reaction equation are as follows:
Compound I, compound ii, R in compound III1、R2It respectively can be for hydrogen atom, the straight chain containing 1~6 carbon atom or containing 3
The branched alkyl of~6 carbon atoms, R3For the linear or branched alkyl group containing 2~18 carbon atoms.
Preferably, R1For methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, amyl or hexyl, R2For methyl, ethyl,
Propyl, isopropyl, butyl, tert-butyl, amyl or hexyl, R3For C16-C18Straight chained alkyl.
Further, the R1With R2It is tert-butyl, R3For C16-C18Straight chained alkyl can greatly improve antioxidant
Antioxidant effect.
Contain R in the new liquid antioxidant3Group makes in liquid condition under its room temperature, and transport is convenient with metering, should
Contain in new liquid antioxidant molecular structure there are two hindered phenol group, there is more excellent antioxidant activity.
A kind of new liquid hindered phenol antioxygen compound I preparation method of the invention be by compound ii, compound III,
Catalyst is put into closed reaction vessel, and reaction is replaced air in reaction vessel using inert gas before starting, and is replaced
Heating carries out esterification after the completion, vacuumizes in esterification reaction process, reaction was completed after reaction to a period of time and it is simple after
Up to new liquid antioxidant of the present invention after processing.The usually described post-processing refers to unreacted compound ii from anti-
It answers and removal is evaporated in vacuo in system, concrete operation step those skilled in the art can select and determine according to common sense, herein not
It is described further.
The molar ratio of preferred compound II and compound III is 2.0~2.5:1 in method made above.
Preferred catalyst is organic tin catalyst, the catalysis of alkali or alkaline earth metal salt class in method made above
Agent, catalyst amount are compound with the 0.1% to 5% of II dosage；
Preferably, catalyst is more efficient using the transesterification of organic tin catalyst, and catalyst amount is II object of chemical combination use
The 0.25% of amount.
Inert gas used in method made above can be N2Or CO2。
Ester exchange reaction vacuum degree described in method made above is 120mmHg to 2mmHg, and reaction temperature is 100 DEG C
To 200 DEG C, preferred reaction scheme is that lower reaction temperature is used since reaction, be gradually increased instead with reaction
Answer temperature and vacuum degree.
The preferred reaction time is 4~10h in method made above.
The preferred reaction time is 6~8h in method made above, and reaction effect is more preferable.
This project product is added in polypropylene product and is squeezed out by double screw extruder 3 times, the 2nd extrusion is tested
Each extrusion sample melt index of oxidation induction period, this project product has excellent antioxygenic property as the result is shown.This project
It is 0.1~2.0% that product, which generally recommends dosage as the high molecular materials such as lubricating oil, polyurethane, polyolefin antioxidant,.
Detailed description of the invention
The accompanying drawings constituting a part of this application is used to provide further understanding of the present application, and the application's shows
Meaning property embodiment and its explanation are not constituted an undue limitation on the present application for explaining the application.
Fig. 1 is the liquid phase spectrogram of product in the embodiment of the present invention 1；
Wherein 1.688min is 3- (3,5- di-tert-butyl-hydroxy phenyl) methyl propionate, and 13.070min is that the present invention is special
Sharp target product.
Fig. 2 is the infrared spectrum of product in the embodiment of the present invention 1.
Fig. 3 is the mass spectrogram of product in the embodiment of the present invention 1.
Specific embodiment
The invention will be further described combined with specific embodiments below, but is not intended to limit patent protection of the invention
Range.Under the premise of without departing from technical solution of the invention, those of ordinary skill in the art made for the present invention hold
Any change easily realized is fallen within scope of patent protection of the invention.
Embodiment 1
By octadecyldiethanol amine 23.29g (0.065mol), 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid first
Ester 38.01g (0.130mol), dimethyl tin oxide 0.058g are added in 250mL four-hole boiling flask, use CO2Replace reaction system
In air, be replaced rear enclosed reaction system, vacuumized and temperature reaction with vacuum pump, be warming up to 120 DEG C, adjust vacuum
Degree be gradually increased reaction temperature and vacuum degree, end of a period reaction temperature 170 with reaction to 120mmHg, clock reaction 8h
DEG C, vacuum degree≤2mmHg.Be warming up to after reaction 210 DEG C, vacuum degree≤2mmHg unreacted 3- (the tertiary fourth of 3,5- bis- is evaporated off
Base -4- hydroxy phenyl) methyl propionate, 56.25g weak yellow liquid, yield 98.32% are obtained after cooling.
Embodiment 2
By octadecyldiethanol amine 23.29g (0.065mol), 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid first
Ester 41.81g (0.143mol), Dibutyltin oxide 0.058g are added in 250mL four-hole boiling flask, with nitrogen displacement reaction system
In air, nitrogen is replaced rear enclosed reaction system, is vacuumized with vacuum pump and temperature reaction, is warming up to 140 DEG C, adjusts
Vacuum degree be gradually increased reaction temperature and vacuum degree with reaction, end reaction temperature to 120mmHg, clock reaction 6h
190 DEG C of degree, vacuum degree≤2mmHg.Be warming up to after reaction 210 DEG C, vacuum degree≤2mmHg unreacted 3- (3,5- is evaporated off
Di-tert-butyl-hydroxy phenyl) methyl propionate, 56.40g weak yellow liquid, yield 98.58% are obtained after cooling
Embodiment 3
By octadecyldiethanol amine 23.29g (0.065mol), 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid first
Ester 40.00g (0.1625mol), dioctyl tin oxide 0.058g are added in 250mL four-hole boiling flask, replace reaction system with nitrogen
Air in system, nitrogen are replaced rear enclosed reaction system, vacuumize simultaneously temperature reaction with vacuum pump, are warming up to 160 DEG C, adjust
Vacuum degree is saved to 120mmHg, clock reaction 7h, be gradually increased reaction temperature and vacuum degree with reaction, end reaction
180 DEG C of temperature, vacuum degree≤2mmHg.Be warming up to after reaction 210 DEG C, vacuum degree≤2mmHg be evaporated off unreacted 3- (3,
5- di-tert-butyl-hydroxy phenyl) methyl propionate, 56.45g weak yellow liquid, yield 98.67% are obtained after cooling.
Embodiment 4
By 1,2,3 products obtained therefrom 0.5g of embodiment be dissolved in 20mL methanol and with 500gPP powder (middle petrochemical industry (Qingdao) 040
Powder) it is sufficiently mixed the uniformly rear removal methanol of volatilization naturally, above-mentioned material is carried out to 3 times on SHJ-20 double screw extruder and is squeezed
It tests out, tests the 2nd extrusion sample oxidation induction period and each extrusion sample melt index, while test is not added with any help
For the blank sample of agent for comparing, it is shown that test result is as follows:
The test of 1 oxidation induction period of table
Note: 190 DEG C of test temperature
The test of 2 melt index of table
Note: 230 DEG C of test temperature, 2.16kg
It is added in polymer from 1,2,3 sample of the embodiment of the present invention in terms of table 1,2 data of table and significantly increases polymer
Oxidation induction period has preferable protective effect, liquid antioxidant of the present invention to polymer repeated processing processing melt index
With excellent antioxygenic property.
The foregoing is merely preferred embodiment of the present application, are not intended to limit this application, for the skill of this field
For art personnel, various changes and changes are possible in this application.Within the spirit and principles of this application, made any to repair
Change, equivalent replacement, improvement etc., should be included within the scope of protection of this application.
Claims (10)
1. a kind of Liquid hindered phenol anti-oxidant compounds I, which is characterized in that its general formula of molecular structure are as follows:
Wherein, R1And R2Respectively one of hydrogen atom, the straight chain containing 1~6 carbon atom, branched alkyl containing 3~6 carbon atoms,
R3For the linear or branched alkyl group containing 2~18 carbon atoms.
2. Liquid hindered phenol antioxidant as described in claim 1, which is characterized in that R1For methyl, ethyl, propyl, isopropyl
Base, butyl, tert-butyl, amyl or hexyl, R2For methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, amyl or hexyl, R3
For C16-C18Straight chained alkyl.
3. Liquid hindered phenol antioxidant of any of claims 1 or 2, which is characterized in that the R1With R2It is tert-butyl, R3
For C16-C18Straight chained alkyl.
4. a kind of preparation method of Liquid hindered phenol antioxidant, which comprises the steps of:
(1) by compound ii and compound III, catalyst investment closed reaction vessel, reaction will using inert gas before starting
Air is replaced in reaction vessel, and heating carries out esterification after the completion of displacement, and the structural formula of the compound ii isThe structural formula of compound III isThe compound ii and compound
III molar ratio is 2.0~2.5:1；
(2) it is vacuumized in esterification reaction process, reacts after 4~10h that reaction was completed, by unreacted compound ii from reaction system
Up to new liquid antioxidant of the present invention after middle vacuum distillation removal.
5. preparation method as claimed in claim 4, which is characterized in that catalyst is organic tin catalyst, alkali metal or alkali
Earth metal saline catalyst, catalyst amount are compound with the 0.1% to 5% of II dosage.
6. preparation method as claimed in claim 4, which is characterized in that catalyst is organic tin catalyst, catalyst amount
It is the 0.25% of II object dosage of chemical combination.
7. preparation method as claimed in claim 4, which is characterized in that the inert gas is N2Or CO2。
8. preparation method as claimed in claim 4, which is characterized in that the vacuum degree of the ester exchange reaction be 120mmHg extremely
2mmHg, reaction temperature be 100 DEG C to 200 DEG C, reaction begin with lower reaction temperature, with reflection progress gradually
Promote reaction temperature and vacuum degree.
9. preparation method as claimed in claim 4, which is characterized in that the reaction time is 6~8h.
10. Liquid hindered phenol antioxidant as described in claim 1 is in the application of high molecular material anti-oxidation field.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201810660889.4A CN108929237A (en) | 2018-06-25 | 2018-06-25 | A kind of new liquid antioxidant and preparation method thereof |
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| CN201810660889.4A CN108929237A (en) | 2018-06-25 | 2018-06-25 | A kind of new liquid antioxidant and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110305366A (en) * | 2019-07-29 | 2019-10-08 | 山东省临沂市三丰化工有限公司 | A kind of antioxidative stabilizer composition and modified butadiene rubber |
| CN110423397A (en) * | 2019-08-29 | 2019-11-08 | 山东三丰新材料有限公司 | A kind of antioxidative stabilizer composition and its application in polyethylene coating materials |
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| JPS505437A (en) * | 1973-05-17 | 1975-01-21 | ||
| US3920729A (en) * | 1973-05-10 | 1975-11-18 | Sumitomo Chemical Co | Isopropanolamine esters of 3-(3,5 di-t-butyl-4-hydroxyphenyl)propanoic acid |
| US5023283A (en) * | 1986-12-24 | 1991-06-11 | Ciba-Geigy Corporation | N,N-bis(acyloxyethyl)hydroxylamine derivatives |
| JPH06206266A (en) * | 1992-10-13 | 1994-07-26 | Skc Ltd | Polyester film and its production |
| WO2006110311A2 (en) * | 2005-03-28 | 2006-10-19 | The Lubrizol Corporation | Lubricant and concentrate compositions comprising hindered-phenol-containing diester antioxidant and method thereof |
| CN101346136A (en) * | 2005-10-24 | 2009-01-14 | 西巴控股公司 | Protection of oxidizable agents |
| CN104140556A (en) * | 2014-08-13 | 2014-11-12 | 北京天罡助剂有限责任公司 | Triazine compound with photooxidation resistance and heat oxidation resistance and synthesis method thereof |
| CN107827921A (en) * | 2017-11-02 | 2018-03-23 | 山东三丰新材料有限公司 | A kind of Hinered phenols antioxidant of novel siliceous and preparation method thereof |
-
2018
- 2018-06-25 CN CN201810660889.4A patent/CN108929237A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1001098A (en) * | 1963-04-29 | 1965-08-11 | Geigy Ag J R | Esters containing alkylhydroxyphenyl groups and their use in the stabilisation of organic compounds |
| US3920729A (en) * | 1973-05-10 | 1975-11-18 | Sumitomo Chemical Co | Isopropanolamine esters of 3-(3,5 di-t-butyl-4-hydroxyphenyl)propanoic acid |
| JPS505437A (en) * | 1973-05-17 | 1975-01-21 | ||
| US5023283A (en) * | 1986-12-24 | 1991-06-11 | Ciba-Geigy Corporation | N,N-bis(acyloxyethyl)hydroxylamine derivatives |
| JPH06206266A (en) * | 1992-10-13 | 1994-07-26 | Skc Ltd | Polyester film and its production |
| WO2006110311A2 (en) * | 2005-03-28 | 2006-10-19 | The Lubrizol Corporation | Lubricant and concentrate compositions comprising hindered-phenol-containing diester antioxidant and method thereof |
| CN101346136A (en) * | 2005-10-24 | 2009-01-14 | 西巴控股公司 | Protection of oxidizable agents |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110305366A (en) * | 2019-07-29 | 2019-10-08 | 山东省临沂市三丰化工有限公司 | A kind of antioxidative stabilizer composition and modified butadiene rubber |
| CN110305366B (en) * | 2019-07-29 | 2021-03-12 | 山东省临沂市三丰化工有限公司 | Antioxidant stabilizer composition and modified butadiene rubber |
| CN110423397A (en) * | 2019-08-29 | 2019-11-08 | 山东三丰新材料有限公司 | A kind of antioxidative stabilizer composition and its application in polyethylene coating materials |
| CN110423397B (en) * | 2019-08-29 | 2022-04-01 | 山东三丰新材料有限公司 | Antioxidant stabilizer composition and application thereof in polyethylene film material |
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