CN1288142C - 3-substituted phenyl-benzo furanone stabilizer and preparing process thereof - Google Patents
3-substituted phenyl-benzo furanone stabilizer and preparing process thereof Download PDFInfo
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- CN1288142C CN1288142C CN 200410045039 CN200410045039A CN1288142C CN 1288142 C CN1288142 C CN 1288142C CN 200410045039 CN200410045039 CN 200410045039 CN 200410045039 A CN200410045039 A CN 200410045039A CN 1288142 C CN1288142 C CN 1288142C
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Abstract
The present invention relates to a 3-substituted phenyl-benzo furanone stabilizer and a preparation method thereof. A structural general formula of the 3-substituted phenyl-benzo furanone stabilizer is characterized in that the structural general formula is disclosed in a formula (1); in the formula (1), R1 stands for hydrogen, acyl, alkyl, aralkyl and allyl, R2 and R5 stand for hydrogen, C1 to C10 alkyl, C6 to C10 cycloalkyl or aryl, and aralkyl, and R3 and R4 stand for C1 to C10 alkyl, C6 to C10 cycloalkyl or aryl and aralkyl. 3-substituted phenyl-benzo furanone is used as a stabilizer for resisting degradation caused by heat, oxidation or photoinduction for organic polymers and organic substances.
Description
Technical field
The invention relates to 3-substituted-phenyl-benzofuranone stabilization agent and preparation thereof.
This type of 3-substituted-phenyl-benzofuranone causes the stablizer of degrading as organic polymer and organic substance opposing heat, oxidation or photoinduction.
Background technology
Indivedual 3-aryl-benzofuranones are openly reported the earliest:
M.H.Hubacher J.Org.Chem.24，1949(1959)；
J.Gripenberg Acta Chemica Scandinavia 23 2583(1969)
M.Auge Bull.Soc.Chim.Fr.1970 4024
J.Morvan Bull.Soc.Chim.Fr.1979 583
Some 3-aryl-benzofuranone starts from as the report of organic polymer and organic substance stablizer:
US4325863 1982
US4338224 1982
EP415887 1991 relevant same Patent: US5175312 1992
3-aryl-benzofuranone occurs in succession as the report of organic polymer and organic substance stablizer subsequently:
The DE4432732 same Patent of being correlated with: US6359148 B1 US6346630 B1 US5814692
US5773631 US5516920 CN1191229A CN1106809A
The CA2132132 same Patent of being correlated with: US5607624 CN1111627A
The EP0591102 same Patent of being correlated with: US5428162 CN1087906A
The DE4316611 same Patent of being correlated with: US5488117 US5369159
DE4316876 same Patent: the US5367008 that is correlated with
EP0589839 same Patent: the US5428177 that is correlated with
The EP0644190 same Patent of being correlated with: US5807505 US5693829 US5614572 CN1106032A
And industrialization product appears.
Disclosed by the invention is the class 3-aryl-benzofuranone different with above-mentioned bibliographical information, and this type of 3-substituted-phenyl-benzofuranone is especially suitable for use as heat, oxidation or photoinduction cause the degrading stablizer of organic polymer and organic substance.
Summary of the invention
The purpose of this invention is to provide a new class 3-aryl-benzofuranone, be especially suitable for use as heat, oxidation or photoinduction cause the degrading stablizer of responsive organic polymer and organic substance, and with this type of 3-aryl-benzofuranone succinct synthetic method accordingly.
The invention provides its general structure for this reason and be the 3-substituted-phenyl-benzofuranone shown in (1) formula.
(1) in the formula
R
1Be: hydrogen, acyl group, alkyl, aralkyl, allyl group;
R
2, R
5Be: hydrogen, C
1-C
10Alkyl, C
6-C
10Cycloalkyl or aryl, aralkyl.
R
3, R
4Be: C
1-C
10Alkyl, C
6-C
10Cycloalkyl or aryl, aralkyl.
R wherein
1Be: hydrogen; R
3, R
4Be: methyl; R
2, R
5Be: the tertiary butyl;
Structural formula shown in (2) formula, its called after:
5-methyl-7-the tertiary butyl-3-(the 5-methyl-3-tertiary butyl-2-hydroxy phenyl)-2 (3H)-benzofuranones.
R wherein
1Be: ethanoyl; R
3, R
4Be: methyl; R
2, R
5Be: the tertiary butyl;
Structural formula shown in (3) formula, its called after:
The acetate 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester.
R wherein
1Be: acryl;
R
3, R
4Be: methyl;
R
2, R
5Be: the tertiary butyl;
Structural formula shown in (4) formula, its called after:
The vinylformic acid 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester.
R wherein
1Be: methacryloyl;
R
3, R
4Be: methyl;
R
2, R
5Be: the tertiary butyl;
Structural formula shown in (5) formula, its called after:
The methacrylic acid 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester.
The disclosed need that the 3-aryl-the benzofuranone synthetic method has relate to aryl alcohol acid intermediate, and what have will be through 3-hydroxyl-benzofuranone intermediate, all quite loaded down with trivial details.
The synthetic method of 3-substituted-phenyl-benzofuranone provided by the invention is corresponding more succinct.
Compound shown in general structure (S1) formula, (S1) in the formula:
R
1Be hydrogen, R
2, R
5Be: hydrogen, C
1-C
10Alkyl, C
6-C
10Cycloalkyl or aryl, aralkyl.R
3, R
4Be: C
1-C
10Alkyl, C
6-C
10Cycloalkyl or aryl, aralkyl.
(S1) formula comprises compound shown in (2) formula
The synthetic method of compound shown in general structure (S1) formula is:
With 2,4-disubstituted benzenes phenol or 4-fortified phenol and oxoethanoic acid condensation, esterification cyclization subsequently makes, and two-step reaction is finished in same reactor.
2, the mol ratio of 4-disubstituted benzenes phenol or 4-fortified phenol and oxoethanoic acid is 1.80-2.20: 0.90-1.10.Catalyzer is: alkylsulphonic acid, aryl sulfonic acid contains sulfonic ion exchange resin, mineral acid example hydrochloric acid, sulfuric acid.
Reaction can be solvent-free, and 130-200 ℃ of fusion at high temperature carried out.
Solvent is used in reaction, temperature of reaction between 30-150 ℃,
Optional solvent: halogenated alkane is as 1, the 2-ethylene dichloride,
Aromatic hydrocarbons such as toluene, benzene, dimethylbenzene
Aliphatic carboxylic acid is as acetate, propionic acid, formic acid.
Compound shown in general structure (S2) formula, (S2) in the formula:
R
6Be: C
1-C
20Alkyl, C
1-C
20Contain unsaturated link(age) alkyl, C
6-C
10Cycloalkyl, aryl, aralkyl,
R
2, R
5Be: hydrogen, C
1-C
10Alkyl, C
6-C
10Cycloalkyl or aryl, aralkyl.
R
3, R
4Be: C
1-C
10Alkyl, C
6-C
10Cycloalkyl or aryl, aralkyl.
(S2) formula comprises compound shown in (3), (4), (5) formula
The synthetic method of compound shown in general structure (S2) formula is: with general structure
(S1) reaction of compound shown in the formula and corresponding acid anhydrides or carboxylic acid halides makes,
The mol ratio of the compound shown in general structure (S1) formula and corresponding acid anhydrides or carboxylic acid halides is 0.90-1.10: 0.90-1.10.
Phenolic hydroxyl group in the compound shown in general structure (S1) formula also can carry out the O-alkylation, and H is replaced by alkyl, aralkyl, allyl group; The O-alkylating reagent is as benzylic type, allyl type halogenide, tertiary olefin, epoxy compounds, sulfuric ester, aromatic sulfonic acid ester etc.
3-substituted-phenyl-benzofuranone provided by the invention is especially suitable for use as heat, oxidation or photoinduction cause the degrading stablizer of responsive organic polymer and organic substance.
These to heat, oxidation or photoinduction cause degrading responsive organic polymer and organic substance as:
1, various olefin homos, multipolymer, olefin polymer mixture and modified olefin polymer thing.
2, α, the homopolymer of beta-unsaturated acid and derivative thereof, or with other monomeric multipolymers.
3, by unsaturated alcohol, amine or its acyl derivative, acetal derivant resulting polymers.
4, the homopolymer of cyclic ethers and multipolymer.
5, polyacetal.
6, polyphenylene oxide, polyphenylene sulfide, or with other mixture of polymers.
7, polymeric amide.
8, polyimide, polyureas, polybenzimidazole.
9, polyester, unsaturated polyester.
10, polycarbonate.
11, polysulfones, polyethersulfone, polyetherketone.
12, phenolic aldehyde, urea-formaldehyde resin.
13, Synolac.
14, Resins, epoxy.
15, natural polymer.
16, natural or synthesis of organic substance.
17, natural or synthetic rubber.
18, photosensitive imaging emulsion.
3-substituted-phenyl-benzofuranone provided by the invention also can be shared with following other stablizer or polymer builder,
1, phenolic antioxidant.
2, UV light absorber and photostabilizer.
3, metal passivator.
4, phosphorous acid ester and phosphinate.
5, peroxide scavenger.
6, polymeric amide stablizer.
7, alkaline auxiliary stablizer.
8, transparent nucleator.
9, fill toughener.
This type of 3-substituted-phenyl-benzofuranone is suitable as the photosensitive imaging emulsion stablizer of being made up of polymkeric substance and organism; With the shared polyolefin stabilizers that is suitable as very much of phenolic antioxidant, phosphorous acid ester and phosphinate.
Stablizer of the present invention is caught the restraint except that having the basic parent 3-of benzofuranone strong carbon radicals of position tertiary carbon and oxygen radical, its 3-bit substituent part also has traditional hindered phenol antioxygen active structure unit, that have in addition also contain unsaturated link(age) [compound shown in (4), (5) formula] can with combined with radical in addition with the macromolecular chain bonding, thereby efficient is higher, and anti-transport property is better.
Description of drawings
Fig. 1, the 5-methyl-7-tertiary butyl-3-(5-methyl-3 tertiary butyls-2-hydroxy phenyl)-2 (3H)-benzofuranone infrared spectras
Fig. 2, the 5-methyl-7-tertiary butyl-3-(5-methyl-3 tertiary butyls-2-hydroxy phenyl)-2 (3H)-benzofuranone proton nmr spectras
Fig. 3, the acetate 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester infrared spectra
Fig. 4, the acetate 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester proton nmr spectra
Fig. 5, the vinylformic acid 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester infrared spectra
Fig. 6, the vinylformic acid 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester proton nmr spectra
The invention will be further described for embodiment below the embodiment, but the present invention is not limited to following examples.
The embodiment 1 5-methyl-7-tertiary butyl-3-(5-methyl-3 tertiary butyls-2-hydroxy phenyl)-2 (3H)-benzofuranones are synthetic
Add 83.0 gram 4-methyl-2-tert.-butyl phenols in 500 milliliters of round-bottomed flasks, 48.0 gram oxoethanoic acids, 40% aqueous solution, 200 milliliters of acetate, 2 milliliters of vitriol oils, 4 milliliters of concentrated hydrochloric acids; The dress prolong; under the argon shield; begin heating, earlier 90 ℃ of degree reactions 2 hours, after refluxing then about 8 hours; be chilled to room temperature; suction filtration, with 100 ml waters washing three times, purifying obtains white powder crystalline solid product: the 5-methyl-7-tertiary butyl-3-(5-methyl-3 tertiary butyls-2-hydroxy phenyl)-2 (3H)-benzofuranones 55.6 grams; productive rate 60.0%, fusing point 210-212 ℃.
Ultimate analysis C
24H
30O
3Theoretical value C 78.65%, and H 8.25%
Measured value C 78.46%, H 8.02%
Infrared spectra IR (KBr compressing tablet) ν cm
-1(referring to accompanying drawing 1)
1776.09cm
-1(benzofuranone carbonyl) 3434.20cm
-1(phenolic hydroxyl group)
Proton nmr spectra
1H-NMR (CDCl
3) δ ppm (referring to accompanying drawing 2)
1.411 (9H), 2.203 (3H) (5 ' methyl H of 3 ' tertiary butyl H of 3-substituted-phenyl),
1.452 (9H), 2.384 (3H) (5 methyl H of 7 tertiary butyl H of benzofuran-2-ones parent),
5.232 (1H) (the benzofuran-2-ones parent: 3 H),
(6.5856.581 1H is bimodal), 7.0787.074 (1H is bimodal) (6 ', 4 ' H of 3-substituted-phenyl),
6.962 (1H), 7.134 (1H) (benzofuran-2-ones parent: 4,6 H).
The embodiment 2 acetate 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester is synthetic
150 milliliters of round-bottomed flasks add the 18.3 gram 5-methyl-7-tertiary butyl-3-(5-methyl-3 tertiary butyls-2-hydroxy phenyl)-2 (3H)-benzofuranones, 50 milliliters of dimethylbenzene, and under 50 ℃ of degree, Dropwise 5 .3 restrains diacetyl oxide, adds back insulation 2 hours; Washing then removes removal xylene, and purifying gets white powder crystalline solid product: the acetate 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-cumarone ketone group) phenyl ester 13.3 grams, productive rate 65.0%, fusing point 166-169 ℃.
Ultimate analysis C
26H
32O
4Theoretical value C 76.44%, and H 7.90%
Measured value C 76.27%, H 7.63%
Infrared spectra IR (KBr compressing tablet) ν cm
-1(referring to accompanying drawing 3)
1798.48cm
-1(benzofuranone carbonyl) 1758.40cm
-1(acetyl carbonyl)
Proton nmr spectra
1H-NMR (CDCl
3) δ ppm (referring to accompanying drawing 4)
1.357 (9H), 2.247 (3H) (5 ' methyl H of 3 ' tertiary butyl H of 3-substituted-phenyl),
1.428 (9H), 2.283 (3H+3H) (7 tertiary butyl H of benzofuran-2-ones parent
Methyl H in 5 methyl H and the ethanoyl),
4.687 (1H) (the benzofuran-2-ones parent: 3 H),
(6.549 1H broad peak), 7.059 (1H) (6 ', 4 ' H of 3-substituted-phenyl),
(6.919 1H broad peak), 7.193 (1H) (benzofuran-2-ones parent: 4,6 H).
The embodiment 3 vinylformic acid 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester is synthetic
150 milliliters of round-bottomed flasks add the 18.3 gram 5-methyl-7-tertiary butyl-3-(5-methyl-3 tertiary butyls-2-hydroxy phenyl)-2 (3H)-benzofuranones, 50 milliliters of dimethylbenzene, 5.3 gram triethylamine, under 50 ℃ of degree, drip 4.8 gram acrylate chlorides, add back insulation 2 hours: washing then, remove removal xylene, purifying gets white powder crystalline solid product: the vinylformic acid 4-methyl-2-tertiary butyl-6-(5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-cumarone ketone group) phenyl ester 12.6 grams, productive rate 60.0%, fusing point 160-163 ℃.
Ultimate analysis C
27H
32O
4Theoretical value C 77.11%, and H 7.67%
Measured value C 76.92%, H 7.41%
Infrared spectra IR (KBr compressing tablet) ν cm
-1(referring to accompanying drawing 5)
1812.88cm
-1(benzofuranone carbonyl) 1736.03cm
-1(acryloyl carbonyl)
Proton nmr spectra
1H-NMR (CDCl
3) δ ppm (referring to accompanying drawing 6)
1.349 (9H), 2.248 (3H) (5 ' methyl H of 3 ' tertiary butyl H of 3-substituted-phenyl),
1.410 (9H), 2.284 (3H) (5 methyl H of 7 tertiary butyl H of benzofuran-2-ones parent),
4.670 (1H) (the benzofuran-2-ones parent: 3 H),
(6.049 1H broad peak), 7.036 (1H) (6 ', 4 ' H of 3-substituted-phenyl),
(6.629 1H broad peak), 7.199 (1H) (the benzofuran-2-ones parent: 4,6 H),
(6.356 1H broad peak) (relative carbonyl is at two key opposite side H in the acryl),
(6.526 1H broad peak) (in acryl with carbonyl adjacent carbons on H),
(6.949 1H broad peak) (in acryl with carbonyl at two keys the same side H).
Proton nmr spectra: benzofuran-2-ones parent: 4,6 H,
6 ', 4 ' H particular location of 3-substituted-phenyl is referring to (1) formula
Infrared spectra IR instrument model Perkin-Elmer Spectrum One
Nuclear magnetic resonance nmr instrument model Bruker-400
Embodiment 4 polypropylene are extruding pelletization stability experiment A repeatedly
1.5 kilogram polypropylene powder
(the polypropylene powder 075-1 of plastic molding and processing plant of Jinling Petrochemical Co. of China Petrochemical Corporation)
(230 ℃, 2.16 kilograms of melting index measured values 11.0),
Do not add stablizer of the present invention,
Or only add one of 0.03% embodiment, 1,2,3 products used as stabilizers,
With twin screw extruder at 260 ℃ of three extruding pelletizations,
(the parallel parallel dual-screw extruding machine SJSH-30 of Nanjing Rubber-Plastic Machinery Plant)
Survey melting index (230 ℃, 2.16 kilograms) then,
(melt flow rate (MFR) instrument XNR-400 Chengde gold is built detecting instrument company limited)
Melting index raises, and chain degradation takes place meaning, and stability degenerates.
The results are shown in Table 1:
Three extruding pelletization stability experiments of table 1 polypropylene powder A
| The compounds of this invention | Melting index restrains/10 fens 230 ℃, 2.16 kilograms |
| ----------------- | 100.0 11.1 9.8 9.3 |
1.5 kilogram polypropylene powder
(the polypropylene powder 075-1 of plastic molding and processing plant of Jinling Petrochemical Co. of China Petrochemical Corporation)
(230 ℃, 2.16 kilograms of melting index measured values 11.0),
Add 0.05% antioxidant 3114 earlier:
1,3,5-(3,5-di-t-butyl-4 hydroxybenzyl) guanamine, 4,6-(1H, 3H, 5H) triketone
With 0.02% oxidation inhibitor 168: tricresyl phosphite (2, the 4-di-tert-butyl) ester
Add one of 0.01% embodiment, 1,2,3 products used as stabilizers again,
With twin screw extruder at 260 ℃ of three extruding pelletizations,
(the parallel parallel dual-screw extruding machine SJSH-30 of Nanjing Rubber-Plastic Machinery Plant)
Survey melting index (230 ℃, 2.16 kilograms) then,
(melt flow rate (MFR) instrument XNR-400 Chengde gold is built detecting instrument company limited)
Melting index raises, and chain degradation takes place meaning, and stability degenerates.
The results are shown in Table 2:
Three extruding pelletization stability experiments of table 2 polypropylene powder B
(having added earlier 0.05% antioxidant 3114 and 0.02% oxidation inhibitor 168)
| The compounds of this invention | Melting index restrains/10 fens 230 ℃, 2.16 |
| Embodiment | |
| 1 product 0.01 | 11.8 10.9 10.2 |
Claims (4)
1,3-substituted-phenyl-Benzopyranone kind stabilizer, its name is called the acetate 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester, and structural formula is characterized as shown in the formula (3):
2,3-substituted-phenyl-cumarone stablizer, its name is called the vinylformic acid 4-methyl-2-tertiary butyl-6-(the 5-methyl-7-tertiary butyl-2,3-dihydro-2-oxo--3-benzofuryl) phenyl ester, and structural formula is characterized as shown in the formula (4):
3, the purposes of claim 1 or 2 described 3-substituted-phenyl-benzofuranones is used for organic polymer and organic substance opposing heat, oxidation or photoinduction and causes degraded.
4, the purposes of claim 1 or 2 described 3-substituted-phenyl-benzofuranones is shared with phenolic antioxidant, phosphorous acid ester and phosphinate, is used for polyolefine opposing heat, oxidation or photoinduction and causes degraded.
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|---|---|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586404A (en) * | 2018-06-12 | 2018-09-28 | 湖南大学 | A kind of synthetic method of N- aryl naphtho- furanone imine compound |
| CN108947948A (en) * | 2018-06-12 | 2018-12-07 | 湖南大学 | A kind of N- aryl naphtho- furanone imine compound and its synthetic method |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100345836C (en) * | 2005-10-17 | 2007-10-31 | 湘潭大学 | Benzopyranone kind stabilizer and its application |
| CN100439350C (en) * | 2006-10-16 | 2008-12-03 | 湘潭大学 | Benzofuranone-like stabilizer and its use |
| JP6559224B2 (en) * | 2014-08-05 | 2019-08-14 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 3-Phenyl-benzofuran-2-one diphosphite derivatives as stabilizers |
| CN109694362B (en) * | 2017-10-23 | 2023-05-09 | 江苏裕事达新材料科技有限责任公司 | 3-arylbenzofuranone propionamide compound, composition formed by same, preparation method and application thereof |
-
2004
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586404A (en) * | 2018-06-12 | 2018-09-28 | 湖南大学 | A kind of synthetic method of N- aryl naphtho- furanone imine compound |
| CN108947948A (en) * | 2018-06-12 | 2018-12-07 | 湖南大学 | A kind of N- aryl naphtho- furanone imine compound and its synthetic method |
| CN108947948B (en) * | 2018-06-12 | 2021-07-20 | 湖南大学 | N-aryl naphthofuranone imine compound and synthetic method thereof |
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