The way the radical (co)polymerization

 

(57) Abstract:

The invention relates to a method of radical (co)polymerization of Monomeric vinyl ether, vinylchloride, diene, Acrylonitrile-olefin optionally with one or more Ethylenediamine monomers. In the way to hold the stage of polymerization of the specified monomer with a polymerization initiator in the presence of a quantity of at least one nadkislot regulator polymerization degree, effective to reduce the molecular weight (co)polymer in comparison with the molecular weight (co)polymer obtained in the same way without controller polymerization degree. The above nadcisnienie control degree of polymerization selected from the group of compounds that contain a fragment of the formula I

< / BR>
provided that neccisary control degree of polymerization is not initiated polymerization. The technical result - reduction of time of polymerization, a smaller regulators influence degree on the average particle size and obtain polymers of good quality with a low molecular weight. 7 C.p. f-crystals, 4 PL.

The invention relates to a method of radical (co)polymerization of Monomeric vinyl ether, blame the rich polymerization is carried out in the presence of nadkislot regulator polymerization degree, through which control is exercised over the molecular weight of the resulting (co)polymer, the invention relates to (co)polymers obtained by this method, and using nagkalat as a regulator of the molecular weight during polymerization of these monomers.

The General concept of the use of molecular weight regulators, known as the regulators of the degree of polymerization (or the vector of the kinetic chain) used in the polymerization reaction, are well known. However, such regulation of the degree of polymerization have a number of disadvantages. For example, they often delay the reaction of polymerization. In addition, many regulators degree of polymerization contain mercaptopropyl or other sulfur-containing functional groups, which make their use undesirable and work with them from the point of view of safety and ecology. And finally, many regulators polymerization degree well perform their function only when performing specific reaction and cannot be used in other reactions of polymerization or number of initiators.

When conducting (co)optimalisatie vinyl chloride monomers, it is often desirable to obtain low molecular weight products. This is whether the regulator polymerization degree. The first option is often undesirable, as in this case, special requirements to the reactor, and the type and amount of polymerization initiator to be used.

In the second case, when the regulator is used, the degree of polymerization selected from the group comprising 2-mercaptoethanol, 2-ethylhexylacrylate and 2 ethylhexanal, the disadvantage of this method is that the polymerization reaction is substantially delayed in such a regulator polymerization degree, and that some of these materials do not wish to use from the point of view of safety and environmental protection.

The purpose of the present invention is to overcome these disadvantages of the known regulators of the degree of polymerization by applying narcissitic regulators, which do not include undesirable sulfur-containing groups and which do not inhibit the polymerization reaction substantially, and, moreover, can speed it up.

The first object of the present invention is a method of radical (co)polymerization of monomers, vinyl ether, vinylchloride, diene, Acrylonitrile - olefin optionally with one or more SEEIT nadkislot regulator polymerization degree, which reduces molecular weight (co)polymer in comparison with the molecular weight (co)polymer obtained in a similar way without controller polymerization degree.

Control degree of polymerization, which is used in the method of the present invention, is selected from the group of compounds that contain a fragment of the formula I:

< / BR>
More specifically, the preferred nagkalat recommended for the method of the present invention, are selected from the group of compounds of the following formula:

< / BR>
where substituent R is chosen from the group comprising H, CH3C(O)OOH, C(O)OH, C(O)OCH3C(O)OR1C2-C20-alkyl, C3-C20-cycloalkyl, C6-C20-aryl, C7-C20-aralkyl or C7-C20-alkaryl, where the alkyl groups can be linear or branched and where alkyl, cycloalkyl, aryl, kalkilya and alarilla groups are optionally substituted by one or more groups Y, where Y is a group selected from among-C(O)OOH, hydroxy-, alkoxy-, aryloxy-, epoxy group, halogen atom, -C(O)OR1, -OC(O)R1, -C(O)OH, nitrile groups, nitro groups, -C(O)NR1R2, -C(O)OTHER1, -C(O)NH2, -N(R1)C(O)R2whether R1and R2independently from each other selected from the group comprising C2-C20-alkyl, where C3-C20-cycloalkyl, C6-C20-aryl, C7-C20-aralkyl and C7-C20-alkaryl, where the alkyl group can be linear or branched, and

< / BR>
where substituent R3is selected from the group comprising a hydrogen atom, a C1-C20-alkyl, C3-C20-cycloalkyl, C6-C20-aryl, C7-C20-aralkyl, C7-C20-alkaryl and radicals containing aminogroup, which can be linear or branched, Deputy R4is selected from the group comprising C1-C20-alkylene, C2-C20-albaniles, C6-C20-Allen, C7-C20-kalkeren, C7-C20-elkarren, C3-C20-cycloalkyl and C3-C20-cycloalkenyl where Allenova and alkenylamine group can be linear or branched, and the substituent R3and/or R4are not necessarily hosted by one or more groups Y as defined above, and Deputy X can be a simple bond or a group selected from: -SO2-, -N(R5)C(O)-, -C(O)N(R5)-, -C(O)N[C(O)(R5)]-, -NHC(O)N(H)-; where the substituent R5in the C7-C20-aralkyl and C7-C20-alkaryl, where the alkyl groups can be linear or branched and optionally substituted by one or more groups Y, the values of which are defined above, the substituents R3and R5can be combined with the formation of ring-containing substituents selected from the group including cycloalkyl, aryl, aralkyl or aralkyl, and the ring optionally substituted by one or more groups Y, the values of which are defined above.

The present invention also relates to (co)polymers obtained by this method (co)polymerization. The third object of the present invention is the use of at least one nagkalat formulas I and III as a regulator of the degree of polymerization with a radical polymerization of one or more Ethylenediamine monomers.

From U.S. patent 2813885 follows that nagkalat are known compounds and are used, for example, as the initiators of the polymerization reaction when the reaction of free-radical polymerization, such as, for example, polymerization of the vinyl monomers. In addition, inventor's certificate of the USSR 2140318 it is known that peroxide of IRN the AI polymerization, and that these peroxides have the ability to regulate molecular weight. However, unlike the present invention there is no separate initiator of the polymerization reaction and there is no assurance that the peroxide fatty acids really are nagkalat used in the method claimed in the present invention.

In the patent application PCT/EP93/03323 discloses the use as a regulator of the degree of polymerization of the partially unsaturated nagkalat. However, these unsaturated compounds is beyond the scope of the present invention. And finally, nagkalat, as it is known, for example, from U.S. patent 4866146, can also be used as initiators for the polymerization reaction of acrylates at 130-140oC. However, in this application does not specify the use of nagkalat as regulators polymerization degree.

Thus, the present invention provides a new method of (co)polymerization of Monomeric vinyl ether, vinylchloride, diene, Acrylonitrile-olefin optionally with one or more Ethylenediamine monomers, whereby can be obtained polymers with a low molecular weight without such defects as poymerization, which significantly slows down the reaction of polymerization and/or contains undesirable sulfur-containing group. In the present invention, the term "(co)polymer" should be understood as "polymers and/or copolymers".

Nagkalat of the present invention can be obtained by one or more methods that are well known to specialists in this field. For example, in many cases, the synthesis can be carried out by treating the corresponding carboxylic acid with hydrogen peroxide. Other methods of synthesis are described, for example, Organic Peroxides, Daniel Swern, Editor, John Wiley & Sons, Inc., New York (1970).

In the preferred embodiment of the present invention, nagkalat formulas II and III are limited nagkakamali, where the substituent R is selected from the group comprising C3-C20-alkyl, C5-C20-cycloalkyl, C7-C20-aralkyl, C7-C20-alkaryl, where all groups can be linear or branched, and where the substituent R4represents a C1-C20-alkylene, C5-C20-cycloalkyl, C6-C20-Allen, C7-C20-kalkeren, C7-C20-elkarren, and C3-C20-cycloalkenyl, X can be a simple link or a sulfon group, and the substituent R3is titlename to the present invention, are optionally substituted phthalimide radicals, including tetrahydropyrimido and hexahydrophthalic, succinimido, maleimido, citraconic and iacomini group.

More preferably, the regulators degree of polymerization are essentially soluble in oil, so they will dissolve in the suspension monomer phase or emulsion polymerization medium. More preferably, nagkalat of the present invention are also stable when stored at temperatures up to 40oC.

The substituents R, R3and R4can be selected depending on the specific method (co)polymerization with regard to their impact on the transport coefficient circuit nagkalat and its solubility in oil or to provide greater stability of nagkalat during storage. Taking this into consideration, the substituents R, R3and R4containing long (C10-C20) alkyl groups, preferred owing to the positive influence of alkyl groups such length on solubility in oil and the stability of nagkalat during storage.

Nagkalat of the present invention can be obtained, to transport, store and apply in the form in which they sushestvuete. Which of these forms is preferred, depends on the reaction of (co)polymerization, as well as other conditions of use, transportation and storage.

The method of the present invention can be carried out similarly and essentially in the same conditions as the normal way using known regulators of the degree of polymerization, such as 2-mercaptoethanol and 2-atransexual. More detailed information about the usual way can be found, for example, in the report "High Temperature Polymerization and Use of Chain Transfer Agents in Low Molecular Wight PVC Manyfacture", Hirose, Y. and Westmijze, H., PVC Seminar 1993, represented by Kayaku Akzo Corporation, as well as in canadian patent application 2077397. This method is especially suitable for (co)polymerization of Monomeric vinyl chloride in obtaining polymers with a low molecular weight used for the manufacture of bottles and special molded under pressure of the subject.

Also in this study are redox polymerization reactions, such as reactions described in the French patent application 2086635 and German patent applications 1915537 and 2006966. Usually such the polymerization reaction is carried out in the presence of a reducing agent in the emulsion polymerizate the EU ETS. First, they have unexpectedly good ability to control and reduce the molecular weight products standard methods of polymerization. Moreover, in applying this nakilat is no sharp slowdown in the polymerization reaction, which is observed in the case of conventional regulators degree of polymerization. In fact, some of the presented nagkalat essentially accelerate the polymerization reaction. Thirdly, the real regulators of the degree of polymerization does not contain unwanted serosoderjaschei groups, such as, for example, mercaptopropyl.

In addition, these regulators degree of polymerization not lower the degree of conversion of monomer. And finally, these reactions nagkalat give additional benefits consisting in the possibility of reducing the required amount of the polymerization initiator used in combination with nagkalat. This additional advantage is the fact that nagkalat in certain conditions can act as a regulator of the degree of polymerization and to some extent as an initiator.

This method differs from the conventional method of polymerization,however, are used in addition to standard initiators of polymerization. The number and type of nagkalat can be selected depending on the reaction temperature, the polymerized monomer, the polymerization initiator and the desired degree of reduction in molecular weight. In General, the method of the present invention is to use a number of nagkalat, which reduces the molecular weight of the final (co)polymer in comparison with the (co)polymer obtained in a similar way in the absence of the Governor polymerization degree.

Usually use from 0.001 to 30 wt.% (based on the weight of monomer) nadkislot regulator polymerization degree. More preferably from 0.01 to 5.0 wt.% nagkalat and most preferably from 0.02 to 2.0 wt.% nagkalat. In the framework of the present invention may also be used mixtures of two or more regulators polymerization degree.

It is preferable to choose a regulator of the degree of polymerization with a higher decomposition temperature than the temperature of the polymerization, as a significant decomposition of the regulator leads to diminished activity in the regulation of the degree of polymerization. However, this requirement is not always necessary. For example, it may be desirable to use nagkalat, the in this case, the partial decomposition of nagkalat during the polymerization reaction is desirable.

The polymerized monomers that can be used in the method of the present invention, are vinyl ether, vinylchloride, Acrylonitrile - olefin, which may not necessarily be copolymerizable with one or more ethyleneamines monomer. In the conditions of the polymerization reaction, the monomers are not easily epoxidase. The preferred monomers are vinyl chloride, vinylidenechloride, viniferin and vinylidenefluoride. The comonomers may be selected preferably from the group comprising acrylates, methacrylates, styrene, derivatives of styrene, vinyl ethers, vinylchloride, dieny, Acrylonitrile and - olefins. Preferably, the comonomers not been easy epoxydecane under standard polymerization conditions.

As the polymerization initiator can be used the usual polymerization initiators, which are well known in this field. The preferred polymerization initiator for a particular reaction will depend on the polymerized monomer used and the reaction temperature. Preferred for use in the us.

The present invention also relates to (co)polymers and oligomers obtained by the method of the present invention and used to produce products that are made from one or more (co)polymers produced in accordance with the method of the present invention. The articles of manufacture can be, for example, bottles or molded under pressure of the subject. Finally, the present invention relates also to the use of nagkalat as a regulator of the degree of polymerization in the way of radical polymerization.

The following examples are provided for further explanation of the present invention.

Examples 1-10 and comparative examples A-G

Polyvinyl alcohol (0.29 grams Gohsenol KP-08 ex. Nippon Gohsei) dissolved in 520 g of water in a one litre Buchi autoclave made of stainless steel with three-bladed stirrer and an air baffle (about 735./min) and a temperature sensor. To the resulting solution was added phosphate buffer system consisting of 0.2 g of Na2HPO4and 0.2 g of NaH2PO4controller polymerization degree, the type and amount of which are shown in table 1, and 0,573 g of polymerization initiator peroxide bis(3,5,5-trimethylhexanoyl) (sample 90,8%).

Then from the reactor otka the temperature of the reaction 62oC for 60 minutes and then kept at this temperature for 6 hours. Then the remaining monomer vinyl chloride otdovat, polyvinyl chloride is filtered off and washed with water, dried over night at 50oC in a drying Cabinet.

Then polyvinylchloride analyzed to determine the weight of the conversion of vinyl chloride monomer. Additionally determine the average particle size using a Coulter Counter Muifisizer, bulk density and dry fluidity using Erichen Din Cup 243/11.8 in accordance with the method of ASTM D1895. The molecular weight is given in the form of K-values, which are measured in accordance with DIN 53726. The results are shown in table 1. In the tables, the abbreviation "C. P. D.," is a time constant pressure".

These examples show that regulators degree of polymerization of the present invention reduce the molecular weight of the polymer compared with the molecular weight control of the polymer (examples A, E and G). In addition, the curing time significantly more for regulators degree of polymerization known level than for regulators degree of polymerization of the present invention, which in most cases provide the same, or more briefly the penalties polymerization of the present invention have a smaller impact on the average particle size. Therefore when using the controls, the degree of polymerization of the present invention can be polymers of good quality with a low molecular weight.

Example 11 and comparative examples H-K

For these examples use the method and the procedure of examples 1-10 except that controls the degree of polymerization in accordance with the present invention compared to some other commercially available controls the degree of polymerization. The results are presented in table 2.

The data in table 2 clearly show significant advantages from the point of view of the reaction time, which can be achieved using the preferred regulators degree of polymerization of the present invention instead of the commercially available regulators polymerization degree PVC used at the present time.

Examples 12-14 and comparative examples 1 to N

In these examples, use the methods of the previous examples except that changing the polymerization initiator to indicate that the controller of the degree of polymerization of the present invention works with a number of different polymerization initiators. Initiator concentration and regulalry in table 3.

These experiments show that aglaonema acid works well as a regulator of the degree of polymerization with three different free radical initiators.

Examples 15-18 and comparative examples O-R

In these examples, use the methods of the previous examples except that the change and the temperature of polymerization and the initiator, to indicate that the controller is the degree of polymerization of the present invention can be used in a wide temperature range. The results are shown in table 4.

The above examples are given only for explanation and characteristics of the invention and should not be construed as limiting the present invention. The amount of the claims of the present invention is defined by the following claims.

1. The way the radical (co)polymerization of at least one monomer selected from vinyl ether, vinylchloride, diene, Acrylonitrile-olefin optionally with one or more Ethylenediamine monomers, characterized in that the conducting phase polymerization of the specified monomer with a polymerization initiator in the presence of a quantity of at least one nadkislot the controller with many brand is popular weight (co)polymer, in the same way without controller polymerization degree, and the above nadcisnienie control degree of polymerization selected from the group of compounds that contain a fragment of the formula I

< / BR>
provided that neccisary control degree of polymerization is not initiated polymerization.

2. The method according to p. 1, characterized in that the above nadcisnienie control degree of polymerization selected from the group of compounds having the formula II

< / BR>
where substituent R is selected from the group comprising H, CH3C(O)OOH, C(O)OH, C(O)OCH3C(O)OR1C2-C20-alkyl, C3-C20-cycloalkyl, C6-C20-aryl, C7-C20-aralkyl and C7-C20-alkaryl, where the alkyl groups can be linear or branched and where alkyl, cycloalkyl, aryl, kalkilya and alarilla groups are optionally substituted by one or more groups Y, where Y is a group selected from among - C(O)OOH, hydroxy-, alkoxy-, aryloxy-apachegroup, halogen atom, -C(O)OR1, -OC(O)R1, -C(O)OH, nitrile group, nitro, -C(O)NR1R2, -C(O)OTHER1, -C(O)NH2, -N(R1)C(O)R2, -SO2NR1R2, -S from each other are selected from the group including C2-C20-alkyl, C3-C20-cycloalkyl, C6-C20-aryl, C7-C20-aralkyl and C7-C20-alkaryl, where the alkyl group can be linear or branched, and

< / BR>
where substituent R3selected from the group comprising a hydrogen atom, a C1-C20-alkyl, C3-C20-cycloalkyl, C6-C20-aryl, C7-C20-aralkyl, C7-C20-alkaryl and radicals containing aminogroup, where the alkyl groups can be linear or branched;

Deputy R4selected from the group including C1-C20-alkylene, C2-C20-albaniles, C6-C20-Allen, C7-C20-kalkeren, C7-C20-elkarren, C3-C20-cycloalkyl and C3-C20-cycloalkenyl where Allenova and alkenylamine group can be linear or branched, and the substituents R3and/or R4are optionally substituted by one or more groups Y as defined above;

Deputy X is selected from a simple communication or group-SO2-, -N(R5)C(O)-, -C(O)N(R5)-, -C(O)N[C(O)(R5)], and-NHC(O)N(H)-, where the substituent R5selected from the group including C2-C20-alkyl, C3-C3and R5can be combined with the formation of ring-containing substituents selected from the group including cycloalkyl, aryl, aralkyl or alkaryl, and the ring optionally substituted by one or more groups Y, the values of which are defined above.

3. The method according to p. 2, characterized in that in the above controller polymerization degree substituent R is chosen from the group comprising C3-C20-alkyl, C5-C20-cycloalkyl, C7-C20-aralkyl and C7-C20-alkaryl, where the alkyl groups can be linear or branched.

4. The method according to p. 2, characterized in that in the above controller polymerization degree substituent R3choose from the group of radicals containing aminogroup, Deputy X represents a simple bond or sulfon, and the substituent R4selected from the group including C1-C20-alkylene, C6-C20-Allen, C7-C20-kalkeren, C7-C20-elkarren.

5. The method according to any of paragraphs.1 to 4, characterized in that the above control degree of polymerization is essentially soluble in oil.

6. Spomer above nadkislot regulator polymerization degree.

7. The method according to p. 6, characterized in that the above-mentioned monomer is a vinyl chloride.

8. The method according to any of paragraphs.1 to 7, characterized in that the above-mentioned polymerization initiator is chosen from the group comprising azo-initiators, paroxetine, diarilpirimido and PEROXYDICARBONATE.

 

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