CN102295499A - Polymerization inhibitor for inhibiting polymerization of vinyl compound - Google Patents
Polymerization inhibitor for inhibiting polymerization of vinyl compound Download PDFInfo
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Abstract
The invention provides a polymerization inhibitor for inhibiting polymerization of a vinyl compound. The polymerization inhibitor is a composition which comprises a component A and a component B, wherein the component A is one or a mixture of more than two of piperidine oxygen radical, nitrophenol or benzoquinone; the component B is one or a mixture of more than two of diethylene glycol monomethyl ether, diethylene glycol dimethyl ether or diethylene glycol monobutyl ether; and based on weight part, the ratio of the component A to the component B is 1:(0.5-2.0). The polymerization inhibitor also comprises solvent dimethylformamide, toluene or dimethylbenzene. Compared with the prior art, the polymerization inhibitor in the invention has the advantages that when the solvent is adopted to prepare the solution-like polymerization inhibitor, the amount of the solvent is reduced, the concentrations of effective components are improved, and the consumption amount of the solvent is reduced; and the polymerization inhibition property is better after the component A and the component B are compounded, thus a small amount of polymerization inhibitor is added in a vinyl compound system, so that the system can obtain an ideal polymerization inhibition effect.
Description
Technical field
The present invention relates to a kind of ethene suppressing based compound polymeric stopper that is used for, what particularly the poly-component of resistance comprised piperidines oxyradical, nitrophenol and/or benzoquinones is used for ethene suppressing based compound polymeric stopper.
Background technology
Vinyl compound mostly is broad-spectrum organic monomer greatly, is the raw material of making numerous organic materialss, more important vinyl compound such as isopentene, isoprene, divinyl, vinylbenzene, vinyl cyanide and (methyl) vinylformic acid and ester thereof etc.Vinyl compound common feature is to contain the very active vinyl group of chemical property; in the accumulating or the course of processing, be subjected to multiple factor affecting such as high temperature, superoxide, iron ion; chain radical polymerization very easily takes place and generate polymkeric substance; this not only causes material loss; also can be in device interior deposition or fouling; make equipment or line clogging, cause potential safety hazard or reduce the equipment cycle of operation and production efficiency.Therefore, no matter in the accumulating or the course of processing, contain in the system of vinyl compound and must add stopper, polymeric takes place and the formation of foulant to suppress.
In the prior art, ethene suppressing based compound polymeric stopper is of a great variety, and wherein good and highly versatile is employed more because of polymerization inhibition effect for piperidines oxyradical, nitrophenol and benzoquinones etc.As Chinese patent application 95115274.2 disclose a kind of under high temperature and no air conditions ethene suppressing base aromatics and alicyclic vinyl compounds of group polymeric method.Wherein, with 4-hydroxyl-2,2,6,6-tetramethyl piperidine-N-oxide compound or 4-acetylaminohydroxyphenylarsonic acid 2,2,6,6-tetramethyl piperidine-N-oxide compound separately or with the mixture of p-Nitrosophenol or 2-methyl-4-nitrosophenol as inhibitor.U.S. Pat 5,888,356 disclose a kind of prevention vinyl aromatic (as vinylbenzene, Vinylstyrene), vinyl fat family's (as vinylformic acid, methacrylic ester) polymeric method, it adopts 4-hydroxyl-2,2,6, the mixture of 6-tetramethyl piperidine oxyradical and p-Nitrosophenol or 2-methyl-4-nitrosophenol is a stopper.
Its main mechanism of action of ethene suppressing based compound polymeric stopper is by the living chain free radical reaction in stopper molecule and the system, generates non-free radical or low activity free radical that can not initiated polymerization, thereby polymerization is stopped.Stopper molecule and chain free radical are fully reacted, necessarily require stopper that very good dissolving dispersion state is arranged in system.The stopper that existing employing piperidines oxyradical, nitrophenol and/or benzoquinones etc. are mixed with in selectable solvent and the dissolution dispersity in the vinyl compound system can be all not very good, this makes the preparation stopper need more solvent on the one hand, causes the poly-effect of its resistance to weaken on the other hand.
Summary of the invention
The invention provides a kind of ethene suppressing based compound polymeric stopper that is used for, the poly-component of resistance comprises piperidines oxyradical, nitrophenol and/or benzoquinones, by add a kind of auxiliary component in stopper, dissolution dispersity can not ideal enough this technical problem in solvent and in the vinyl compound system to solve stopper.
Below be that the present invention solves the problems of the technologies described above concrete technical scheme:
A kind of ethene suppressing based compound polymeric stopper that is used for, this stopper is a composition, comprises component A and B component.Wherein:
Component A is a kind of in piperidines oxyradical, nitrophenol or the benzoquinones, or two or more mixtures;
B component is a kind of in two methyl ethers of diethylene glycol monomethyl ether, glycol ether or the diethylene glycol monobutyl ether, or two or more mixtures;
In weight part, component A: B component=1: (0.5～2.0).
Also can comprise solvent in the stopper, solvent is a kind of in dimethyl formamide, toluene or the dimethylbenzene, in weight part, (component A+ B component): solvent=(2～8): 10.
Above-mentioned vinyl compound is mainly isopentene, isoprene, divinyl, vinylbenzene, vinyl cyanide, vinylformic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl propenoate or Jia Jibingxisuanyizhi.
In the stopper, component A is preferably piperidines oxyradical or nitrophenol, or both mixtures; B component is preferably diethylene glycol monomethyl ether or diethylene glycol monobutyl ether.
Above-mentioned piperidines oxyradical is generally 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical, 2,2,6,6-tetramethyl piperidine oxyradical or 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical; Nitrophenol is generally 2,2, 4-dinitrophenol, 2,6-dinitro-p-cresol, o-nitrophenol or 2-sec-butyl-4,6-dinitrophenol(DNP).
In weight part, the preferred proportioning of stopper is:
Component A: B component=1: (1.0～1.5);
When adding solvent, (component A+ B component): solvent=(4～6): 10.
Essence of the present invention is to have added auxiliary component, i.e. B component in the stopper.This is a kind of pure ether compound, the contriver finds in experiment, this type of pure ether compound is in organic solvents such as dimethyl formamide, toluene or dimethylbenzene, perhaps in a lot of vinyl compound systems, piperidines oxyradical, nitrophenol and/or benzoquinones etc. there is good solublization, make they in solvent and the dissolution dispersity in the vinyl compound system be greatly improved, stopper contacts more fully with the chain free radical and even reaction more fully, more effectively stop chain radical polymerization, inhibition obviously strengthens.On the other hand, this type of pure ether compound also has certain solvency action for the polymkeric substance of the vinyl compound that has generated, can prevent that polymer molecule knot combinate form from becoming the viscosity decorating film, reduces the generation of polymkeric substance in the fouling of equipment inwall deposition.
In the present invention, the proportioning when selection of the compound of component A or two or more compound are used etc. are all basic identical with prior art, do not cause new or special requirement because of the adding of B component; And B component determine that also be not limited by the selection of component A compound or two or more compound uses the time proportioning.B component is selectable to be two methyl ethers of diethylene glycol monomethyl ether, glycol ether or diethylene glycol monobutyl ether, and the proterties of these compounds is essentially identical, so can be used alone or as a mixture.When mixing use, because selected compounds does not exist synergy, dependence or restricting relation each other, any proportioning that can infer between the selected compounds all is feasible.
On the other hand, with regard to single just " resistance is poly-", solvent is also nonessential, for no other reason than that need being dissolved in the solvent usually, component A and B component add again in the vinyl compound system, and the stopper that directly is mixed with the solution shape use of being more convenient for.In principle, as long as solvent is abundant dissolved constituent A of energy and B component, and the minimum that influences that they and vinyl compound system are produced detrimentally affect or generation all is not suitable, for example when the course of processing that be used to use solvent, should select the identical solvent that is adopted with the course of processing usually.The described solvent of technique scheme only is that the present invention recommends, and they are applicable to most vinyl compound system.
Compared with prior art, the invention has the advantages that solvent load reduces when being mixed with solution shape stopper with solvent, active principle concentration improves, and has reduced the consumption of solvent; Have better polymerization inhibition performance after the composite use of component A and B component, the less stopper of adding just can obtain the ideal polymerization inhibition effect in the vinyl compound system thereby make.
Below will the invention will be further described by specific embodiment.As previously mentioned, proportioning and prior art when the selection of component A or two or more compound are used are basic identical, and the variation of its proportioning does not influence the embodiment of invention effect when B component is the mixture of two or more compounds, embodiment or comparative example will be paid attention to enumerating of proportioning between B component and it and the component A, and for the ease of carrying out the investigation of polymerization inhibition performance, stopper is mixed with the solution shape with solvent.
Embodiment
[embodiment 1～12]
Component A and B respectively get suitable compound, drop in the desired amount in the solvent, impose to be stirred to fully dissolving to be mixed with solution shape stopper standby.Concrete component A, B component and the solvent that adopts of each embodiment sees Table 1, and the mutual proportioning of component A, B component and solvent sees Table 2.
[comparative example 1～4]
Component A gets suitable compound, drops in the desired amount in the solvent, imposes to be stirred to fully dissolving to be mixed with solution shape stopper standby.Concrete component A and the solvent that adopts of each comparative example sees Table 1, and the mutual proportioning of component A and solvent sees Table 2.
Table 1.
| Component A | B component | Solvent | |
| Embodiment 1 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical 2,2, 4-dinitrophenol | Diethylene glycol monobutyl ether | Dimethyl formamide |
| Embodiment 2 | 2,2,6,6-tetramethyl piperidine oxyradical o-nitrophenol | The two methyl ethers of glycol ether | Dimethyl formamide |
| Embodiment 3 | 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | The two methyl ethers of diethylene glycol monobutyl ether glycol ether | Toluene |
| Embodiment 4 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | The diethylene glycol monomethyl ether diethylene glycol monobutyl ether | Dimethyl formamide |
| Embodiment 5 | 2,6-dinitro-p-cresol para benzoquinone | Diethylene glycol monobutyl ether | Dimethylbenzene |
| Embodiment 6 | 2, the 6-dinitro-p-cresol | Diethylene glycol monobutyl ether | Toluene |
| Embodiment 7 | 2-sec-butyl-4, the adjacent benzoquinones of 6-dinitrophenol(DNP) | Diethylene glycol monomethyl ether | Toluene |
| Embodiment 8 | 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | The diethylene glycol monomethyl ether diethylene glycol monobutyl ether | Dimethyl formamide |
| Embodiment 9 | 2-sec-butyl-4, the 6-dinitrophenol(DNP) | The diethylene glycol monomethyl ether diethylene glycol monobutyl ether | Toluene |
| Embodiment 10 | 2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | Diethylene glycol monobutyl ether | Dimethyl formamide |
| Embodiment 11 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | Diethylene glycol monomethyl ether | Toluene |
| Embodiment 12 | 2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | Diethylene glycol monobutyl ether | Dimethyl formamide |
| Comparative example 1 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | - | Dimethyl formamide |
| Comparative example 2 | 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | - | Dimethyl formamide |
| Comparative example 3 | 2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | - | Dimethyl formamide |
| Comparative example 4 | 2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | - | Dimethyl formamide |
Table 2.
| Component A: B component (weight ratio) | (component A+ B component): solvent (weight ratio) | |
| Embodiment 1 | 1∶0.5 | 2.0∶10 |
| Embodiment 2 | 1∶1.0 | 4.0∶10 |
| Embodiment 3 | 1∶2.0 | 5.0∶10 |
| Embodiment 4 | 1∶1.2 | 5.0∶10 |
| Embodiment 5 | 1∶1.5 | 6.0∶10 |
| Embodiment 6 | 1∶1.0 | 6.0∶10 |
| Embodiment 7 | 1∶1.2 | 8.0∶10 |
| Embodiment 8 | 1∶1.1 | 4.5∶10 |
| Embodiment 9 | 1∶1.4 | 7.0∶10 |
| Embodiment 10 | 1∶1.0 | 5.5∶10 |
| Embodiment 11 | 1∶1.3 | 6.0∶10 |
| Embodiment 12 | 1∶1.2 | 7.0∶10 |
| Comparative example 1 | - | 1.8∶10 |
| Comparative example 2 | - | 1.7∶10 |
| Comparative example 3 | - | 2.1∶10 |
| Comparative example 4 | - | 2.3∶10 |
Annotate: in the foregoing description or the comparative example, when component A or B component were the mixture of two kinds of compounds, the proportioning of two kinds of compounds was 1: 1.
The inhibitor solution of each embodiment and comparative example preparation is applied to the polymerization of ethene suppressing based compound respectively.At volume is that 500mL has in the carbon steel material reactor of chuck heating unit, and dropping into 350mL purity is the vinyl compound of 99wt.%, adds inhibitor solution more in the desired amount and mixes nitrogen filled protection in the still.Under the probe temperature of setting, leave standstill, take a sample after the test duration through setting, adopt HP-6890 gas chromatograph analyzing polymers growing amount.
The add-on of stopper is benchmark with the vinyl compound, in the amount of component A.Test condition and test result see Table 3～5, and the vinyl compound of table 3,4 and 5 tests is respectively isoprene, methacrylic acid and vinylbenzene.
Table 3.
| Component A add-on (wt. ‰) | Probe temperature (℃) | Test duration (hr) | Polymkeric substance growing amount (wt.%) | |
| Embodiment 1 | 0.3 | 130 | 24 | 4.2 |
| Embodiment 2 | 0.6 | 130 | 24 | 3.5 |
| Embodiment 3 | 0.8 | 130 | 24 | 2.5 |
| Embodiment 4 | 1.8 | 130 | 24 | 0.8 |
| Embodiment 5 | 1.0 | 130 | 24 | 1.7 |
| Embodiment 6 | 3.0 | 130 | 24 | 1.0 |
| Embodiment 7 | 0.9 | 130 | 24 | 1.6 |
| Embodiment 8 | 1.5 | 130 | 24 | 0.9 |
| Embodiment 9 | 1.2 | 130 | 24 | 1.6 |
| Embodiment 10 | 1.2 | 130 | 24 | 1.0 |
| Embodiment 11 | 1.0 | 130 | 24 | 1.4 |
| Embodiment 12 | 1.8 | 130 | 24 | 0.8 |
| Comparative example 1 | 1.8 | 130 | 24 | 18.2 |
| Comparative example 2 | 1.5 | 130 | 24 | 19.3 |
| Comparative example 3 | 1.2 | 130 | 24 | 25.6 |
| Comparative example 4 | 1.8 | 130 | 24 | 17.6 |
Table 4.
| Component A add-on (wt. ‰) | Probe temperature (℃) | Test duration (hr) | Polymkeric substance growing amount (wt.%) | |
| Embodiment 1 | 0.3 | 120 | 24 | 3.2 |
| Embodiment 2 | 0.6 | 120 | 24 | 2.0 |
| Embodiment 3 | 0.8 | 120 | 24 | 2.0 |
| Embodiment 4 | 1.8 | 120 | 24 | 0.9 |
| Embodiment 5 | 1.0 | 120 | 24 | 2.5 |
| Embodiment 6 | 3.0 | 120 | 24 | 1.5 |
| Embodiment 7 | 0.9 | 120 | 24 | 2.6 |
| Embodiment 8 | 1.5 | 120 | 24 | 1.3 |
| Embodiment 9 | 1.2 | 120 | 24 | 2.0 |
| Embodiment 10 | 1.2 | 120 | 24 | 1.5 |
| Embodiment 11 | 1.0 | 120 | 24 | 1.8 |
| Embodiment 12 | 1.8 | 120 | 24 | 1.0 |
| Comparative example 1 | 1.8 | 120 | 24 | 16.2 |
| Comparative example 2 | 1.5 | 120 | 24 | 20.9 |
| Comparative example 3 | 1.2 | 120 | 24 | 23.5 |
| Comparative example 4 | 1.8 | 120 | 24 | 18.3 |
Table 5.
| Component A add-on (wt. ‰) | Probe temperature (℃) | Test duration (hr) | Polymkeric substance growing amount (wt.%) | |
| Embodiment 1 | 0.3 | 110 | 24 | 3.6 |
| Embodiment 2 | 0.6 | 110 | 24 | 2.2 |
| Embodiment 3 | 0.8 | 110 | 24 | 1.8 |
| Embodiment 4 | 1.8 | 110 | 24 | 0.7 |
| Embodiment 5 | 1.0 | 110 | 24 | 1.6 |
| Embodiment 6 | 3.0 | 110 | 24 | 1.2 |
| Embodiment 7 | 0.9 | 110 | 24 | 2.0 |
| Embodiment 8 | 1.5 | 110 | 24 | 1.0 |
| Embodiment 9 | 1.2 | 110 | 24 | 1.7 |
| Embodiment 10 | 1.2 | 110 | 24 | 1.1 |
| Embodiment 11 | 1.0 | 110 | 24 | 1.5 |
| Embodiment 12 | 1.8 | 110 | 24 | 0.7 |
| Comparative example 1 | 1.8 | 110 | 24 | 16.2 |
| Comparative example 2 | 1.5 | 110 | 24 | 20.6 |
| Comparative example 3 | 1.2 | 110 | 24 | 21.6 |
| Comparative example 4 | 1.8 | 110 | 24 | 15.9 |
Claims (9)
1. one kind is used for ethene suppressing based compound polymeric stopper, and this stopper is a composition, comprises component A and B component, wherein:
Component A is a kind of in piperidines oxyradical, nitrophenol or the benzoquinones, or two or more mixtures;
B component is a kind of in two methyl ethers of diethylene glycol monomethyl ether, glycol ether or the diethylene glycol monobutyl ether, or two or more mixtures;
In weight part, component A: B component=1: (0.5～2.0).
2. stopper according to claim 1 is characterized in that also comprising in the stopper solvent, and solvent is a kind of in dimethyl formamide, toluene or the dimethylbenzene, in weight part, (component A+ B component): solvent=(2～8): 10.
3. stopper according to claim 1 and 2 is characterized in that described vinyl compound is isopentene, isoprene, divinyl, vinylbenzene, vinyl cyanide, vinylformic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl propenoate or Jia Jibingxisuanyizhi.
4. stopper according to claim 1 and 2 is characterized in that described component A is piperidines oxyradical or nitrophenol, or both mixtures.
5. stopper according to claim 1 and 2 is characterized in that described B component is diethylene glycol monomethyl ether or diethylene glycol monobutyl ether.
6. stopper according to claim 1 and 2 is characterized in that described piperidines oxyradical is a 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical, 2,2,6,6-tetramethyl piperidine oxyradical or 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical.
7. stopper according to claim 1 and 2 is characterized in that described nitrophenol is 2,2, 4-dinitrophenol, 2,6-dinitro-p-cresol, o-nitrophenol or 2-sec-butyl-4,6-dinitrophenol(DNP).
8. stopper according to claim 1 and 2 is characterized in that described component A: B component=1: (1.0～1.5).
9. stopper according to claim 2 is characterized in that described (component A+ B component): solvent=(4～6): 10.
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