CN116553996A - Polymerization inhibitor and application thereof - Google Patents
Polymerization inhibitor and application thereof Download PDFInfo
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- CN116553996A CN116553996A CN202310825747.XA CN202310825747A CN116553996A CN 116553996 A CN116553996 A CN 116553996A CN 202310825747 A CN202310825747 A CN 202310825747A CN 116553996 A CN116553996 A CN 116553996A
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- polymerization inhibitor
- polymerization
- quinone methide
- phenylenediamine
- amine compound
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 82
- 239000003112 inhibitor Substances 0.000 title claims abstract description 63
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 62
- -1 amine compounds Chemical class 0.000 claims abstract description 40
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims abstract description 33
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims abstract description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical group CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 claims description 4
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 8
- 230000007613 environmental effect Effects 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- HIBWGGKDGCBPTA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 HIBWGGKDGCBPTA-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 239000004794 expanded polystyrene Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention belongs to the technical field of polymerization inhibitors, and particularly relates to a polymerization inhibitor and application thereof. The polymerization inhibitor provided by the invention comprises quinone methide and amine compounds; the quinone methide has a structure as shown in formula 1; the amine compound is one or more of phenylenediamine, N-substituted phenylenediamine, N' -substituted phenylenediamine and quinone diimide; the mass ratio of the quinone methide to the amine compound is 1-5:1-5. The polymerization inhibitor provided by the invention has good environmental protection and polymerization inhibition and inhibition effects, and can be widely applied.Formula 1.
Description
Technical Field
The invention belongs to the technical field of polymerization inhibitors, and particularly relates to a polymerization inhibitor and application thereof.
Background
Styrene (Styrene) is widely used as an important petrochemical base material as a polymer such as a synthetic resin, an ion exchange resin, and a synthetic rubber. For example, styrene can be polymerized to produce polystyrene resin (PS), expanded Polystyrene (EPS), etc., and is applied to the electronic and electric industry, the daily necessities industry, building materials, packaging materials, etc. For another example, styrene can also be copolymerized with other monomers to manufacture engineering materials with different purposes, such as ABS resin prepared by copolymerizing styrene, acrylonitrile and butadiene, and can be applied to automotive interiors and household appliances; SAN resin is prepared by copolymerization with acrylonitrile and is used for manufacturing transparent plastic products; styrene Butadiene Rubber (SBR) and Styrene Butadiene Latex (SBL) are produced by copolymerization with butadiene, and are used for producing tires, adhesive tapes, papermaking, paints, and the like.
Styrene has unsaturated double bond and forms conjugated system with benzene ring, so that it has strong reaction activity and is easy to produce self-polymerization reaction under the condition of heating. Therefore, the styrene generally has unexpected polymerization reaction in the production process, which can lead to monomer loss, and meanwhile, the generated polymer can be precipitated from the process fluid and deposited on the surface of equipment, thereby blocking tower plates, reboilers, pipelines, pump bodies and the like, and greatly influencing the stable operation of the production device. In order to reduce the polymerization of styrene, the most common method at present is to add an appropriate polymerization inhibitor during the production process to suppress the undesired polymerization reaction.
The polymerization inhibitor can be classified into a True inhibitor (True inhibitor) and a Retarder (Retarder) according to the inhibition effect. The true polymerization inhibitor has a certain polymerization induction period, and basically no polymer is generated during the induction period, but the polymer content is rapidly increased after the induction period is finished. The true polymerization inhibitor has short service life, but high polymerization inhibition efficiency although the dosage is small; typical true inhibitors include 4-hydroxy-2, 6-tetramethylpiperidine nitroxide radical (HTMPO) or diethylhydroxylamine. The polymerization retarder has no induction period, but can obviously reduce the polymerization speed, and the polymer content is slowly increased along with the extension of time. While the polymerization inhibition efficiency of the retarder is lower than that of the true polymerization inhibitor, the retarder is slower to consume in the system and tends to be more effective in the case of an emergency stop of the device. Most of the existing retarders are severely toxic and are environmentally hazardous, such as 2-sec-butyl-4, 6-Dinitrophenol (DNBP). In order to reduce the toxicity of the retarder, scientific researchers try the retarder and the true polymerization inhibitor in a matching way, but the true polymerization inhibitor is consumed too fast in a system, and the retarder performance of the complex is obviously inferior to that of a single retarder.
Therefore, there is a need to develop a polymerization inhibitor which can have good polymerization inhibition performance and high efficiency and environmental protection.
Disclosure of Invention
In view of the above, the invention provides a polymerization inhibitor and application thereof, and the polymerization inhibitor provided by the invention has good polymerization inhibition performance and environmental protection.
In order to solve the technical problems, the invention provides a polymerization inhibitor, which comprises quinone methide and amine compounds;
the quinone methide has a structure as shown in formula 1:
formula 1;
wherein R is 1 And R is 2 Independently is C4-C18 alkyl, C5-C12 cycloalkyl or C7-C15 phenylalkyl;
R 3 and R is 4 independently-H, C1-C18 alkyl, phenyl, substituted phenyl, C5-C12 cycloalkyl, -CN, -COOH, -C=CR 5 、-C≡CR 5 、-COOR 5 、-COR 5 、-OCOR 5 or-CONR 5 ；R 5 is-H, C alkyl of C18, cycloalkyl of C5-C12 or phenylalkyl of C7-C15;
the amine compound is one or more of phenylenediamine, N-substituted phenylenediamine, N' -substituted phenylenediamine and quinone diimide;
the mass ratio of the quinone methide to the amine compound is 1-5:1-5.
Preferably, the quinone methide is a 7-phenyl quinone methide or a 7-carboxylic acid quinone methide.
Preferably, the N, N ' -substituted phenylenediamine is N, N ' -di-sec-butyl-p-phenylenediamine or N, N ' -diphenyl-p-phenylenediamine.
Preferably, the mass ratio of the quinone methide to the amine compound is 2-5:1.
The invention also provides application of the polymerization inhibitor in polymerization inhibition of styrene.
The invention provides a polymerization inhibitor, which comprises quinone methide and amine compounds; the quinone methide has a structure as shown in formula 1:formula 1;
wherein R is 1 And R is 2 Independently is C4-C18 alkyl, C5-C12 cycloalkyl or C7-C15 phenylalkyl; r is R 3 And R is 4 independently-H, C1-C18 alkyl, phenyl, substituted phenyl, C5-C12 cycloalkyl, -CN, -COOH, -C=CR 5 、-C≡CR 5 、-COOR 5 、-COR 5 、-OCOR 5 or-CONR 5 ；R 5 is-H, C alkyl of C18, cycloalkyl of C5-C12 or phenylalkyl of C7-C15; the amine compound is one or more of phenylenediamine, N-substituted phenylenediamine, N' -substituted phenylenediamine and quinone diimide; the mass ratio of the quinone methide to the amine compound is 1-5:1-5. The invention can effectively improve the polymerization inhibition efficiency of the polymerization inhibitor by combining the quinone methide and the amine compound, and has better polymerization inhibition and polymerization inhibition effects, thereby ensuring the stable operation of the styrene preparation device. The polymerization inhibitor provided by the invention has good environmental protection and polymerization inhibition and inhibition effects, and can be widely applied.
Drawings
FIG. 1 is a graph showing the comparison of the polymer content in dotted lines at various times in the systems containing the polymerization inhibitors of example 1 and comparative example 2.
Detailed Description
The invention provides a polymerization inhibitor, which comprises quinone methide and amine compounds.
In the present invention, the quinone methide has a structure as shown in formula 1:
formula 1.
In the present invention, R 1 And R is 2 Independently is a C4-C18 alkyl group, a C5-C12 cycloalkyl group or a C7-C15 phenylalkyl group, preferably independently is a C4-C18 alkyl group, more preferably independently is a tert-butyl group.
In the present invention, R 3 And R is 4 independently-H, C1-C18 alkyl, phenyl, substituted phenyl, C5-C12 cycloalkyl, -CN, -COOH, -C=CR 5 、-C≡CR 5 、-COOR 5 、-COR 5 、-OCOR 5 or-CONR 5 Preferably independently-H or phenyl. In the present invention, R 5 is-H, C alkyl of C18, cycloalkyl of C5-C12 or phenylalkyl of C7-C15.
In the present invention, the quinone methide is preferably 7-phenyl quinone methide or 7-carboxylic acid quinone methide, more preferably 7-phenyl quinone methide.
In the present invention, the amine compound is one or more of phenylenediamine, N-substituted phenylenediamine, N '-substituted phenylenediamine and quinone diimide, more preferably N, N' -substituted phenylenediamine. In the present invention, the N, N ' -substituted phenylenediamine is preferably N, N ' -di-sec-butyl-p-phenylenediamine or N, N ' -diphenyl-p-phenylenediamine.
In the invention, the mass ratio of the quinone methide to the amine compound is preferably 1-5:1-5, more preferably 2-5:1.
The invention has no special requirement on the preservation mode of the polymerization inhibitor, and can preserve the quinone methide and the amine compound in a form of independent package or can preserve the quinone methide and the amine compound in a form of mixture. The invention has no special requirement on the mixing, and the mixing can be uniformly carried out.
The invention also provides application of the polymerization inhibitor in polymerization inhibition of styrene. The invention has no special requirements for the application, and can be realized by adopting a conventional mode in the field. In the present invention, the addition amount of the polymerization inhibitor is preferably 10 to 10000ppm, more preferably 50 to 5000ppm, still more preferably 300ppm, when the polymerization inhibitor is used as a polymerization inhibitor in the synthesis of styrene.
The technical solutions provided by the present invention are described in detail below in conjunction with examples for further illustrating the present invention, but they should not be construed as limiting the scope of the present invention.
Example 1
7-phenyl quinone methide and N, N' -di-sec-butyl-p-phenylenediamine with the mass ratio of 2:1 are used as polymerization inhibitors.
Examples 2 to 3
Polymerization inhibitors were prepared as in example 1, except for referring to Table 1.
Table 1 Condition parameters for preparing efficient environmentally friendly polymerization inhibitor in examples 1-3
Comparative example 1
7-phenyl quinone methide as polymerization inhibitor as comparative example
Comparative example 2
4-hydroxy-2, 6-tetramethylpiperidine nitroxide radical (HTMPO) and 2-sec-butyl-4, 6-Dinitrophenol (DNBP) in a mass ratio of 1:20 are mixed to give a polymerization inhibitor.
The polymerization inhibitors in examples 1-3 and comparative examples 1-2 were added to a styrene experimental apparatus to evaluate the dynamic polymerization inhibition performance of the polymerization inhibitor and examine the control ability of the polymerization inhibitor to the polymer content in a rectifying apparatus. The method comprises the following specific steps:
to 1000g of styrene (TBC removed) was added 300ppm of a polymerization inhibitor; 100mL of the above sample was poured into a polytetrafluoroethylene reaction vessel and a stirring magnet was added, and the remaining sample was poured into a three-necked flask. Connecting a gas guide pipe connected with nitrogen with a flask mouth and placing the gas guide pipe below the liquid level, opening a gas valve to introduce nitrogen into the system, keeping introducing nitrogen in the whole subsequent experimental process, and starting a pump to convey liquid into the reaction kettle; heating was started while stirring, when heated to 125 ℃, timing was started and 10mL of sample was taken at the top of the reaction vessel outlet line, and 10mL of sample was taken every half an hour thereafter for measuring the polymer content until the polymer content reached a steady state, the results of which are shown in table 2.
TABLE 2 polymerization inhibitor Properties of examples 1 to 3 and comparative examples 1 to 2
From Table 2, the polymerization inhibition effect of the high-efficiency environment-friendly polymerization inhibitor is obviously better than that of 7-phenyl quinone methide under the same concentration; the polymerization inhibitor provided by the invention has similar polymerization inhibition effect with the polymerization inhibitor of the comparative example 2, can achieve the combined use effect of the traditional true polymerization inhibitor (HTMPO) and the polymerization inhibitor (DNBP), but the polymerization inhibitor of the comparative example 2 contains 2-sec-butyl-4, 6-Dinitrophenol (DNBP) with higher toxicity.
The polymerization inhibitors in example 1 and comparative example 2 were added to a styrene laboratory apparatus to evaluate the polymerization retarder performance of the polymerization inhibitor and the protection ability of the polymerization inhibitor to the apparatus when the styrene apparatus was accidentally stopped in an emergency. The method comprises the following specific steps:
600ppm of polymerization inhibitor was added to 300g of styrene (TBC removed), the solution was poured into a 500 mL three-neck flask and stirred with a stirrer; then the air duct, the condensing pipe and the reverse plug which are connected with nitrogen are respectively connected with the flask mouth; and opening a gas valve to introduce nitrogen into the system, and keeping introducing nitrogen in the whole subsequent experimental process. Heating was started while stirring, and when heated to 125 ℃, timing was started and about 10mL of the sample was taken out of the flask mouth with a syringe. 10mL of the sample was taken every half hour later for measuring the polymer content, and the results are shown in Table 3.
TABLE 3 polymerization inhibitor Properties of the polymerization inhibitors of example 1 and comparative example 2 at different times
A dotted line versus graph of polymer content at various times in the systems containing the polymerization inhibitors of example 1 and comparative example 2 is plotted according to Table 3, as shown in FIG. 1.
As can be seen from a combination of table 3 and fig. 1, the retarder performance of example 1 is significantly better than the combined use of the true inhibitor (HTMPO) and retarder (DNBP) of comparative example 2, providing longer protection for the styrene unit in the event of an unexpected emergency stop of the unit.
Although the foregoing embodiments have been described in some, but not all, embodiments of the invention, it should be understood that other embodiments may be devised in accordance with the present embodiments without departing from the spirit and scope of the invention.
Claims (5)
1. A polymerization inhibitor, characterized by comprising quinone methide and amine compound;
the quinone methide has a structure as shown in formula 1:
formula 1;
wherein R is 1 And R is 2 Independently is C4-C18 alkyl, C5-C12 cycloalkyl or C7-C15 phenylalkyl;
R 3 and R is 4 independently-H, C1-C18 alkyl, phenyl, substituted phenyl, C5-C12 cycloalkyl, -CN, -COOH, -C=CR 5 、-C≡CR 5 、-COOR 5 、-COR 5 、-OCOR 5 or-CONR 5 ；R 5 is-H, C alkyl of C18, cycloalkyl of C5-C12 or phenylalkyl of C7-C15;
the amine compound is one or more of phenylenediamine, N-substituted phenylenediamine, N' -substituted phenylenediamine and quinone diimide;
the mass ratio of the quinone methide to the amine compound is 1-5:1-5.
2. The polymerization inhibitor according to claim 1, wherein the quinone methide is 7-phenyl quinone methide or 7-carboxylic acid quinone methide.
3. The polymerization inhibitor according to claim 1, wherein the N, N ' -substituted phenylenediamine is N, N ' -di-sec-butyl-p-phenylenediamine or N, N ' -diphenyl-p-phenylenediamine.
4. The polymerization inhibitor according to any one of claims 1 to 3, wherein the mass ratio of the quinone methide to the amine compound is 2 to 5:1.
5. The polymerization inhibitor according to any one of claims 1 to 4, wherein the polymerization inhibitor is used for inhibiting polymerization of styrene.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024064515A1 (en) * | 2022-09-19 | 2024-03-28 | Bl Technologies, Inc. | Polymerization inhibitors for high temperature ethylene fractionation trains |
Citations (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355515A (en) * | 1964-05-13 | 1967-11-28 | Bayer Ag | Secondary aromatic amines as storage stabilizers for unsaturated polyesters containing hydroperoxides |
| CN1139094A (en) * | 1995-04-14 | 1997-01-01 | 希巴-盖吉股份公司 | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| US20040034247A1 (en) * | 2002-08-16 | 2004-02-19 | Sherif Eldin | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| WO2004083156A1 (en) * | 2003-03-17 | 2004-09-30 | Hakuto Co., Ltd. | Polymerization inhibitor for aromatic vinyl compounds and method for inhibiting the polymerization of the compounds |
| JP2004300307A (en) * | 2003-03-31 | 2004-10-28 | Hakuto Co Ltd | Polymerization inhibitor composition of aromatic vinyl compound |
| CN101054335A (en) * | 2002-05-06 | 2007-10-17 | 弗纳技术股份有限公司 | A method for stabilizing vinyl aromatic monomers using selected polymerization inhibitors and polymers prepared therewith |
| US20110297878A1 (en) * | 2010-06-03 | 2011-12-08 | General Electric Company | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
| CN103502194A (en) * | 2011-06-13 | 2014-01-08 | 纳尔科公司 | Synergistic combination for inhibiting polymerization of vinyl monomers |
| CN103619797A (en) * | 2011-06-13 | 2014-03-05 | 纳尔科公司 | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
| CN103764686A (en) * | 2011-08-26 | 2014-04-30 | 多尔夫凯塔尔化学制品（I）私人有限公司 | Additive composition for control and inhibition of polymerization of styrene, and method of preparation and use thereof |
| CN104718181A (en) * | 2012-08-24 | 2015-06-17 | 多尔夫凯塔尔化学制品（I）私人有限公司 | Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof |
| US20160289147A1 (en) * | 2015-03-31 | 2016-10-06 | Ecolab Usa Inc. | Use of quinone methides as antipolymerants for vinylic monomers |
| JP2020132678A (en) * | 2019-02-13 | 2020-08-31 | 栗田工業株式会社 | Method for suppressing polymerization of unsaturated aromatic monomer |
| CN112513005A (en) * | 2018-07-13 | 2021-03-16 | 埃科莱布美国股份有限公司 | Amine oxide and methylated quinone combination as an antifoulant for ethylene monomers |
| CN112533902A (en) * | 2018-07-13 | 2021-03-19 | 埃科莱布美国股份有限公司 | Compositions comprising nitroxide inhibitors, quinone methide blockers and amine stabilizers to inhibit polymerization of monomers |
| CN112739725A (en) * | 2018-09-28 | 2021-04-30 | 埃科莱布美国股份有限公司 | Amino quinone anti-polymerization agents and methods of use thereof |
| CN114502522A (en) * | 2019-10-11 | 2022-05-13 | 埃科莱布美国股份有限公司 | Methylated quinone and ammonium salt anti-polymerization agent compositions and methods |
| WO2022182612A1 (en) * | 2021-02-26 | 2022-09-01 | Bl Technologies, Inc. | Composition and method for inhibiting the formation and growth of popcorn polymers |
-
2023
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Patent Citations (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355515A (en) * | 1964-05-13 | 1967-11-28 | Bayer Ag | Secondary aromatic amines as storage stabilizers for unsaturated polyesters containing hydroperoxides |
| CN1139094A (en) * | 1995-04-14 | 1997-01-01 | 希巴-盖吉股份公司 | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| CN101054335A (en) * | 2002-05-06 | 2007-10-17 | 弗纳技术股份有限公司 | A method for stabilizing vinyl aromatic monomers using selected polymerization inhibitors and polymers prepared therewith |
| US20040034247A1 (en) * | 2002-08-16 | 2004-02-19 | Sherif Eldin | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| WO2004083156A1 (en) * | 2003-03-17 | 2004-09-30 | Hakuto Co., Ltd. | Polymerization inhibitor for aromatic vinyl compounds and method for inhibiting the polymerization of the compounds |
| CN1761638A (en) * | 2003-03-17 | 2006-04-19 | 伯东株式会社 | Polymerization inhibitor for aromatic vinyl compounds and method for inhibiting the polymerization of the compounds |
| JP2004300307A (en) * | 2003-03-31 | 2004-10-28 | Hakuto Co Ltd | Polymerization inhibitor composition of aromatic vinyl compound |
| US20110297878A1 (en) * | 2010-06-03 | 2011-12-08 | General Electric Company | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
| CN103502194A (en) * | 2011-06-13 | 2014-01-08 | 纳尔科公司 | Synergistic combination for inhibiting polymerization of vinyl monomers |
| CN103619797A (en) * | 2011-06-13 | 2014-03-05 | 纳尔科公司 | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
| CN103764686A (en) * | 2011-08-26 | 2014-04-30 | 多尔夫凯塔尔化学制品（I）私人有限公司 | Additive composition for control and inhibition of polymerization of styrene, and method of preparation and use thereof |
| CN104718181A (en) * | 2012-08-24 | 2015-06-17 | 多尔夫凯塔尔化学制品（I）私人有限公司 | Composition of quinone methide derivatives and amines for control and inhibition of polymerization of monomers, and method of preparation and use thereof |
| US20160289147A1 (en) * | 2015-03-31 | 2016-10-06 | Ecolab Usa Inc. | Use of quinone methides as antipolymerants for vinylic monomers |
| CN112513005A (en) * | 2018-07-13 | 2021-03-16 | 埃科莱布美国股份有限公司 | Amine oxide and methylated quinone combination as an antifoulant for ethylene monomers |
| CN112533902A (en) * | 2018-07-13 | 2021-03-19 | 埃科莱布美国股份有限公司 | Compositions comprising nitroxide inhibitors, quinone methide blockers and amine stabilizers to inhibit polymerization of monomers |
| CN112739725A (en) * | 2018-09-28 | 2021-04-30 | 埃科莱布美国股份有限公司 | Amino quinone anti-polymerization agents and methods of use thereof |
| JP2020132678A (en) * | 2019-02-13 | 2020-08-31 | 栗田工業株式会社 | Method for suppressing polymerization of unsaturated aromatic monomer |
| CN114502522A (en) * | 2019-10-11 | 2022-05-13 | 埃科莱布美国股份有限公司 | Methylated quinone and ammonium salt anti-polymerization agent compositions and methods |
| WO2022182612A1 (en) * | 2021-02-26 | 2022-09-01 | Bl Technologies, Inc. | Composition and method for inhibiting the formation and growth of popcorn polymers |
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