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The present invention generally relates to polymerization inhibitor blends and methods for their use. More specifically, the present invention relates to a composition to inhibit the polymerization of monomers comprising at least one hydroxylamine.

<p>5 of a nitroxide and at least one phenylenediamine.</p>

The pre-colored polymerization of ethylenically unsaturated monomers is a major denaturation mechanism in the monomer synthesis process. In general, two classes of compounds have been developed to prevent unwanted and precolored polymerization reactions, consisting of inhibitors and retarders. The inhibitors prevent polymerization reactions and are usually consumed quickly. and working

<p>10 Inhibitors slow down the rate of polymerization reactions but are not as effective as inhibitors. However, retarders are not consumed faster than inhibitors.</p>

And the formation of all the substances that make up the antipolymerants are the agents of inhibitors. And the materials that make up the crystal form in the form of a float, a gateway to help and a constant free radicals, and the twis become an effective and friendly agent.

Being strong or clothed in carbon-centered radicals

<p>15th coupling reactions. It is well known that antioxidants are considered impeding materials, and they are effective hydrogen donors. Well, you will have a strong Voyage effect by quenching the oxygen-mediated holes through the growth of hydrogen to the oxygen-mediated holes.</p>

The unsaturated ethylene monomers are reactive in nature and tend to polymerize via a polymerization mechanism

<p>20 Free traction, especially at high temperatures and when polymerization inhibitors are used. Unwanted polymerization reactions pose operational concerns and may pose serious operational problems when occurring from the distillation process, because high temperatures can accelerate the polymerization reaction.</p>

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The manufacture of monomers saturated with ethylene often consists of three stages of reaction, recovery, and purification. And it uses the sludge process of the evaporation process, such as rotation, wattage, high temperature, water, water, restoration, and purification. The process of polymerization of the monomer that is saturated with ethylene, during manufacturing, is desirable, and that the nucleolus allows the resulting polymer to be deposited from the process stream, and deposited on the process equipment, and the operation is invalid.

<p>5 Al Solim For Promises. In turn, the loss of a toothpick, the use of an upper blood pressure inhibitor, a water heater, and a practical solution</p>

Almoumunmer's photoshoot. So, what is the solution for the preparation, the requirements of the American phone number 02030202012, the technical assistance to confirm the desired effects of the blood, the amount of money, the amount of money, the amount of money, the amount of money, the amount of ethylene, the liquid, the liquid, the liquid, the liquid, the solution, etc.)

dialkyl/aryl hydroxylamine from the first to effectively convert 10 nitroxide into nitroxide hydroxylamine (b) an inhibitory component such as phenylenediamine.

American Tractor No. 0048820-2002 Aoun Mercoup 2, 2, 5, 5-tetramethyl-pyrrolidine-1-oxoyl 2,2,5,5-tetramethyl-pyrrolidine-1-oxyl and 3-hydroxyo-oxyl compound ,2,5,5-R-methioool-pyrroliodine-1-oxoooyl-5,2,2,5-3-hydroxy

<p>15th tetramethyl pyrrolidine-1-oxyl as a stable molecule</p>

polymerization inhibition;

However, the approximate inventiveness tends to create an unpredictable collaborative effect that makes the current invention work more effectively than the previous technology disincentives that do not accelerate the collaborative influence and discover the current inventors.

<p>20 Phenolic oxidants and phenylethylamine are used for oxidation</p>

phenylenediamine, fixed free radicals of nitroxide, and phenothiazine derivatives are commonly used as reagents to inhibit the polymerization process in industry. Hydroquinone HQ, phenothiazine PTZ, phenylenediamine PDA, and 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl are considered to be

<p>4 Examples of some inhibitors of polymerization-hydroxy-2,2,6,6-tetramethyl piperidinyl oxy HTMPO 25</p>

Most widely used in industry. However, conventional inhibitory treatment does not adequately protect against polymerization-induced denaturation. Furthermore, the use of conventional inhibitors poses logistical, economic and safety concerns.

General description of the invention

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You want to make a composition to inhibit the polymerization of monomart. In one aspect, the monomer polymerization inhibition composition comprises at least one hydroxylamine of the nitroxide compound and at least one phenylenediamine.

Any methods of inhibiting the polymerization of monamarte would be considered here. In one aspect, the method of inhibiting monomer polymerization consists in the addition of a fluid comprising an ethylene unsaturated monomer and the addition of an effective amount of the synthesis

Fluid-to-fluidic polymerization inhibitor. The polymerization inhibitor composition comprises at least one effective amount of the hydroxylamine of the nitroxide and at least one effective amount of phenylenediamine. However, adding the polymerization inhibitor composition to the fluid will result in inhibiting the polymerization of the ethylene unsaturated monomer.

The foregoing has shown somewhat in general the technical features and benefits of the present invention in order to better understand the following detailed description of the invention. Additional features and the following will be described below which constitute the subject matter of the claims for the present application. Those skilled in the technique should be aware that the readily disclosed particular concept and embodiments may be used as a basis for modifying or designing other embodiments for the same purposes according to the present invention. Those skilled in the technique should realize that equivalent embodiments of this kind do not deviate from the meaning and scope of the invention as set forth in

Attached Protection Elements.

Brief explanation of the drawings

A detailed description of the invention is described hereafter by referring to the drawings, where

Figure 1 shows laboratory returns that can be used. Wooooooooooooooooooooooooooooooo

20 currently disclosed;

Figure 2 A bio-analytical agent that compares the guanine and according to the inhibitory electrolyte of the exposed polymer

than currently with traditional inhibitors; And

Figure 3

currently disclosed.

25 Detailed description:

Various embodiments of the present invention are described below. The relationship between the function of the various elements of embodiments can be better understood by referring to the following detailed description. However,

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embodiments are not limited to those expressly described herein and it should be understood that in some cases, certain details not necessary to understand the embodiments disclosed herein may be omitted, for example the combination of

and traditional manufacturing method.

The present invention relates to synthesized polymerization inhibitor mixtures and methods for inhibiting the polymerization of uninhibited monomers.

5 Saturated Ethylene. The recombinant mixture/composition of the polymerization inhibitor according to the present invention may be a recombinant mixture/composition comprising multiple components. In one aspect, the blend/inhibited formulation comprises at least one hydroxylamine of the nitroxide and at least one phenylenediamine. All of the polymerization inhibitor combinations/mixtures currently disclosed are effective in scavenging free radicals involved in the inhibition of

<p>10 and diffusion polymerization reaction.</p>

According to the present invention, the hydroxylamine of the nitroxide compound may comprise the hydroxylamine

<img file="SA6470B1_D0001.tif" />

Where R3, R2, R1, or R4 are individually selected from the alkyl group. For

<p>15th For example, you might choose R3, R2, R1, or R4 individually from the group formed from the C1 - C8 alkyl group R. And for you, in some respects, you may choose R3, R2, R1, or R4 individually from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptanyl, and octyl. R is selected separately from the group consisting of hydrogen, oxygen, alkyl, hydroxyl, and hydroxyl.</p>

<p>20 alkoxyl, amino, amido and carboxylate.</p>

The following represent general structures of hydroxylamines for six-vessel ring nitroxides that can be used according to the present invention.

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<img file="SA6470B1_D0002.tif" />

Where R3, R2, R1, or R4 are individually selected from the alkyl group. For

For example, you might choose R3, R2, R1, or R4 individually from the group made up of the C1 - C8 alkyl group R alkyl group. And for you, in some aspects, you may choose R3, R2, R1, or R4 separately

From the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptanyl, and octyl. R and 'R are selected separately from the group consisting of hydrogenalkyl and aryl .aryl

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Accordingly, in specific aspects of the present invention, the hydroxylamine of the nitroxide compound may be selected from the group consisting of 4-hydroxy-2,2,6,6-tetramethylpiperidinol,4-hydroxy-2,2,6, 6-tetramethyl piperidinol-oxo-2,2,6,6-tetramethyl piperidinol-4,4-oxo-2,2,6,6-tetramethyl piperidinol-methoxy-2,2,

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6,6-tetramethyl piperidinol-4,4-methoxy-2,2,6,6-tetramethyl piperidinol-acetate-2,2,6,6-tetramethyl piperidinol-4,4-acetate-2,2,6,6 -tetramethyl piperidinol-amino-2,2,6,6-tetramethyl piperidinol-4,4-amino-2,2,6,6-tertrmethyl piperidinol-acetamido-2,2,6,6-tetramethyl piperidinol 2,1 4-acetamido-2,2,6,6-tetramethyl piperidinol,

5 3,6-Tetrahydro-2,2,6,6-Tetramethylpiperidinol-2,2,6,6-1,2,3,6-tetrahydro

tetramethyl piperidinol, bis(2,2,6,6-tetramethylpiperidinol) sebacate and a combination thereof. In a specific way, the hydroxylamine of the nitroxide compound is 4-hydroxy-2,2,6,6-tetramethyl piperidinol.4-hydroxy-2,2,6,6-tetramethyl piperidinol

10 Hydroxylamines should not be confused with nitrous oxides

The currently disclosed nitroxides and the corresponding nitroxides. The hydroxylamines of the nitroxides have advantages over the corresponding nitroxides, for example the ability to support EV inhibition of the polymerization process, as will be explained in more detail below. A general manufacturing pathway is the product of hydroxylamines

15th of a nitroxide compound in the sister of the corresponding nitroxide compound using a reducing reactant as follows

<img file="SA6470B1_D0003.tif" />

The hydroxylamine of a nitroxide compound is capable of supporting

Adequate inhibition of the polymerization process compared to the corresponding nitroxide compound when carbon-mediated and oxygen-mediated LgR20 inhibitors are present. It is explained as follows

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<img file="SA6470B1_D0004.tif" />

The hydroxylamine of the nitroxide compound is an excellent mano-hydrogen because of my weak NO-H bonds in the compound, but it is an effective antioxidant. As an antioxidant, the hydroxylamine of 5-nitroxide readily reacts with oxygen, such as peroxide radicals, while being converted to the corresponding nitroxide. Nitroxides are generally recognized as the most effective inhibitors due to their superior ability to inhibit via carbon-mediated free radical scavenging at an approximately pi-controlled rate of diffusion. This rate is much faster than the phenolic compounds. However, its kinetic superiority 10 is not always useful. For example, it may lose its supremacy at the presence of oxygen-mediated voids as the dominant free radical. Another concern of nitroxide is that it is consumed through uninhibited and undesirable interactions with process stream components or other inhibitory additives. As a consequence, the use of high doses of a nitroxide inhibitor is often blamed for obtaining the respective inhibitory efficacy,15 and thus makes its use uneconomical or even unviable.

In fact, each hydroxylamine of the nitroxide compound is equivalent to one manohydrogen plus one substance for polymerizing the nitroxide compound at each of the oxygen-mediated and carbon-mediated radicals, which provide edges via hydroxylamines. Hydroxylamines for 20 nitroxides. With it, one hydroxylamine of the nitroxide compound enables the removal of one R-mediated oxygen and R-one-mediated carbon while

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The nitroxide compound is only able to remove the carbon-mediated radical.

The phenylenediamine according to the present invention has the following general structure:

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melt down

5 Where R1 or each selects individually from the group consisting of hydrogen, alkyl, alkylaryl, aryl, aryl alkyl, arylalkyl, hydroxyl-containing alkyl groups, ethoxylate-containing alkyl groups, and alkyl groups containing amino

Amino-containing alkyl groups

10 Thus, in specific aspects of the present invention, phenylenediamine is selected from the group consisting of 1,2-phenylenediamine,[,1,4-phenylenediamine-1,4-phenylenediamine,L1,Ν-di-methyl Para-phenylenediamine -Ν,Ν'-di-methyl-p phenylenediamine, L1,7E-di-then-butyl-1,4-phenylenediamine -Ν,Ν'-di-sec-butyl 4- phenylenediamine,[,L1,7E-di-1,4-dimethylpentyl-1,4-phenylenediamine

15th N,N,N'-di-l,4-dimethylpentyl-],4-phenylenediamine, 'Cy-acetyl-1, 4-phenylenediamine Ν,Ν'-di-acetyl-l,4-phenylenediamine, No- Th-butyl-(7E-phenyl-1,4-N-phenylenediamine,N-tert-butyl-N'-phenyl-],4-phenylenediamine,7E-diphenyl-1,4-phenylenediamine Ν, Ν'-di-phenyl-l,4-phenylenediamine, and any combination thereof.In one aspect, phenylenediamine is L1,7E-di-then-butyl-1,4-phenylene.

20 Diamine Ν,Ν'-di-sec-butyl-l,4-phenylenediamine or L1,7E-di-1,4-dimethylpentyl-1,4-phenylenediamine 0N,N'-di-l, 4-dimethylpenty!-l,4-phenylenediamine

Any aspect of the polymerization inhibitor currently disclosed may comprise a combination of two or more components, eg at least one hydroxylamine of the nitroxide and at least one phenylenediamine. The polymerization inhibitor may contain any amount of each of the 25 components. For example, in some respects it may contain a greater amount of the hydroxylamine of the nitroxide than of phenylenediamine In another aspect it may contain a greater amount of phenylenediamine than the hydroxylamine of the nitroxide and in additional aspects, may include equal amounts of hydroxylamine for nitroxide and diphenylene

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phenylenediamine amine. However, in some respects, the ratio of at least one hydroxylamine of a nitroxide compound to at least one phenylenediamine is from about 1 10 to about 1 10 by weight, or from about 1 5 to about 1

5, or about 11.

The polymerization inhibitor compositions currently disclosed represent more improved compositions compared to the conventional polymerization inhibitor compounds. For example, polymerization inhibitor formulations according to the present invention have more improved efficacy, safety/handling, environmental impact, dosage requirements, and processing costs. Many, if not all, of the improvements depend entirely on the synergies unexpectedly discovered by the present inventors between the various components of the presently disclosed polymerization inhibitor formulations.

According to the present invention, various methods of inhibiting the polymerization of monomart are disclosed. In one aspect, there is a method for inhibiting the polymerization of ethylene unsaturated monomer. Monomart is considered unsaturated

Ethelenia is well-known for its technical know-how, meaning all the monograms

Unsaturated Ethylene B n is covered

By the current patent. With it, the polymerization inhibitor compositions currently disclosed can inhibit the polymerization of ethylene unsaturated monomer.

In some aspects of the invention, the unsaturated monomer selects ethylene from the group consisting of acrylic acid, methacrylic acid, acrylonitrile, methacrylonitrile, acrolein, methacrylon.

methacrolein, acrylate, methacrylate, acrylamide, acrylamide

Methacrylamide, vinyl acetate, butadiene, ethylene, propylene, and styrene.

According to one of the methods of the present invention, a method for inhibiting the polymerization of unsaturated ethylene monomer is disclosed. Again, the unsaturated ethylene monomer can be represented as an unsaturated monomer

Ethylene. The method comprises a step for a fluid weeding comprising an unsaturated ethylene monomer. The fluid is not limited to specific fluids and can represent fluids that are present in the monomer manufacturing process. The fluid may represent the process stream comprising the monomers to which the polymerization inhibitor composition is added.

An effective amount of one or more of the currently disclosed polymerization inhibitory compositions is then applied to the fluid. For example, an effective amount of a composition comprising at least one hydroxylamine of a nitroxide and at least one phenylenediamine may be added to the fluid.

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The hydroxylamine nitroxide and/or phenylenediamine, and/or other components of the polymerization inhibitor composition currently disclosed may be manually or automatically added to the fluid. It may either be destroyed continuously and/or intermittently. A can be completed. Automatic removal through the use of chemical injection pumps. The chemical injection pumps may be programmed. Add specified amounts of the polymerization inhibitor composition, or components thereof, at specified intervals to the fluid. Alternatively, the chemical injection pumps can be controlled manually. Add specified amounts of the polymerization inhibitor composition, or components thereof, to the fluid. Furthermore, phenylenediamine and hydroxylamine of the nitroxide, or other components of the polymerization inhibitor composition, may be added together in one solution to the fluid or may be added separately to the fluid. However, the addition of the currently disclosed polymerization inhibitory compositions will result in the fluid embedding on the unsaturated monomers.

Saturated Ethylene inhibits the polymerization of the unsaturated Ethylene monomer.

The effective amount of at least one hydroxylamine of the nitroxide compound can be the largest amount of the nitroxide that will effectively inhibit the polymerization of the monomers. For example, the effective amount of hydroxylamine may vary

The nitroxide compound varies from about 1 ppm to about 2000 ppm, based on the weight of the monomers. In one aspect, the effective amount may range from about 5 ppm to about 500 ppm. In other words, the effective amount may vary from y yyyy

The hydroxylamine of the nitroxide compound is from about 10 A in 20 million to about 200 A in a million.

The effective amount of at least one phenylenediamine can be the largest amount of the R that will effectively inhibit the polymerization of the monomers. For example, the effective amount of phenylenediamine may range from about 1 ppm to about 2000 ppm, based on the weight of the monomers. In one aspect, the effective amount may range from about 5 ppm to about 500 ppm. and in

In another way, the effective amount of phenylenediamine may range from about 10 ppm to about 200 ppm.

Examples

The performance of the polymerization inhibitor formulations was evaluated using a continuous-flow distillation column over a wide range

30 A laboratory (Figure 1). In the laboratory structure, the column (1) contains a three-necked flask (2).

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The column represents the column chamber and the boiling broth, the (3) insertion assembly with perforated flyer plates represents the distillation column tray section, and the condenser (4) represents the upper condenser to supply the distillation reflux. Feeding, outlet moderation function maintains the liquid level in the sump.

5 heating mantle to the contents of the flask at a temperature between about 85°C and about 95°C. The device simulates the operating environment and dirtiness of a typical distillation process. Acrylate production.

Methyl methacrylate MMA was obtained from the commercially inhibited grade Po 10-35 ppm from mono methyl MEHQ ether hydroquinone. An uninhibited methyl methacrylate was obtained

10 MEHQ alo removal with a tilt to the inhibitor. And use Benzoyl peroxide BPO

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As a polymerization inhibitor in experiments.

And dregs of polymerization inhibitor were administered to uninhibited MMA monomer solution NP to NP with Alo-BPO. The resulting solution was poured into a three-necked flask and heated. The remaining solution from the polymerization inhibitor/uninhibited monomer was poured into the feeding chamber (6). During the experiment, the polymerization/uninhibited monomer inhibitor solution in the feeding chamber was drained to the distillation column from the feeding chamber while The contents of the three-necked flask were squeezed out continuously.

In a first set of experiments, a comparison was made between polymerase inhibitor compositions according to the present invention and conventional polymerization inhibitors. In the first experiment, a dose of 100 ppm of phenothiazine PTZ was iodized to the uninhibited monomer solution. In the second experiment,

A dose of 100 ppm was supplemented by 4-hydroxy-2,2,6,6-tetramethyl

4 to a solution of-hydroxy-2,2,6,6-tetramethyl piperidinyl oxy HTMPO piperidinyl oxy

The monomer is uninhibited. In a third experiment, a velocity of 100 ppm was supplemented with

hydroquinone HQ to an uninhibited monomer solution and in a four-experiment, a dose of

25 Its amount is about 18 ppm of N',N-di-then-butyl-1,4-phenylenediamine

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N,N'-di-sec-butyl-1,4-phenylenediamine and about 18 ppm of 4-hydroxy-2,2,6,6-tetramethylpiperidinol HTMPOH 4-hydroxy-2,2,6,6- tetramethyl piperidinol

into an uninhibited monomer solution. Each experiment was dealt with according to the experimental instructions described above, for example, Saba from the solution into the three-necked flask, pouring the remaining material into a tank

Feeding, draining the solution from the feeding chamber into the distillation column, etc.

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And to test a typical performance, the polymer Turkey yade in the basin with security as a result of polymer formation. An effective polymerization inhibitor can be expected to reduce polymer formation in the distillation column and to slow the rise of the polymer turkey in the tub.

As can be seen in Figure 2, the polymerization inhibitor according to the present invention outperforms all 5 conventional polymerization inhibitors by producing the lowest relative polymer turkey.

The same experimental methods described previously were used in the second set of experiments. To show the bioavailable effect of the aspect related to the polymerization inhibitor structure according to the present invention. In one experiment, a dose of 10 ppm of N',N-di-then-butyl-1,4-phenylenediamine N,N'-di-sec-butyl-1,4-phenylenediamine was euthanized to a solution of The monomer is uninhibited. and in

10 A second experiment, a dose of about 10 ppm of HTMPOH was upgraded to the uninhibited monomer solution and in a third experiment, a dose of about 10 ppm of N',N-di-then-butyl-1,4-phenylene was wedded Diamine N,N'-di-sec-butyl-1,4-phenylenediamine

Ba. Add about 10 ppm of HTMPOH to the uninhibited monomer solution.

The results of these experiments are shown in Figure 3, which, according to F and F, indicate a strong balance between

15th HTMPOH and N',N-di-then-butyl-1,4-phenylenediamine-1,4-N,N'-di-sec-butyl phenylenediamine. It can be expected that this tension in rabbits is due to the polymerization inhibitor compositions currently disclosed.

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Each of the structures and methods disclosed and claimed herein may be used and negated without giving undue experience in the light of the present invention. While this invention may be embodied in many different forms, specific embodiments according to the invention are described in detail here. The present invention is an example of the basics of the invention and is not intended to define the invention with the specific embodiments shown. And ba. In addition, unless expressly indicated otherwise, the . tool is used indefinite article “a” to include “at least one” or “one or more”. For example, the term “polymerization inhibitor” means to include “at least one polymerase inhibitor” or “one or more polymerase inhibitors”.

The terms involved in either an absolute or an approximate value are intended to come from both, and the definitions used here are just u and are not specific to me. However, the numerical ranges and the variable factors that determine the broad scope of the invention are approximate, and the numerical values ​​given in the given examples are calculated as precisely as possible. However, a numerical value is mainly subject to specific errors that necessarily result from the standard deviation resulting from the particular test measurements. Furthermore, it should be understood that all of the ranges disclosed herein come from all sub-ranges (including

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All integer and integer values) shown here.

And yes, all of the above, that's all about the best possible combinations of some or all of the different embodiments described here. It should also be understood that many of the changes and modifications that are made to the currently available embodiments described herein will be made to the person skilled in the technology.

5 Changes and modifications can be made without deviating from the principle and scope of the invention and without detracting from the intended points. However, it is intended that the changes and adjustments be included in the attached protection elements.

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