Concentrate, suitable for the production of functionalized polyolefin, the method of obtaining a concentrate, methods of functionalization of homopolymers and copolymers of olefins, functionalized polyolefin

 

(57) Abstract:

Describes a new concentrate, suitable for the production of functionalized polyolefins, in the form of particles of olefin polymer selected from homopolymers or copolymers of olefins with the formula RCH=CH2where R is H or an alkyl radical c 1 to 8 carbon atoms or aryl radical, or mixtures thereof, and these particles are coated on the surface and inside under a mixture of additives comprising: a) from 0.05 to 30% by weight relative to the total weight of the concentrate, of one or more vinyl monomer selected from the group comprising unsaturated cyclic anhydrides and aliphatic diesters or dicyclomine derivatives, and vinyl monomers are depolimerizuet, when they are mixed with particles of these olefin polymers at a temperature of 50 - 70°C, in the presence of an initiator of free radicals, which are inactive at temperatures below or equal to 70°C. also Describes a method of obtaining a concentrate, methods of functionalization of homopolymers and copolymers of olefins, functionalityand polyolefins. The obtained products are endowed with optimum adhesion to metals. 5 C. and 10 C.p. f-crystals.

The invention relates to laws, as well as the functionalization process using the above concentrates.

Known various processes by which changes apolar nature of olefin polymers by introducing polar groups in their macromolecular chains, such as carboxyl, hydroxyl, ether or amino groups.

The above processes include the reaction of olefin polymers in the presence of generators radicals with organic compounds which, in addition, that contain one or more of the above functional groups typically contain at least one double bond. The above-mentioned double bond, in addition, that enables the graft copolymerization of polar compounds in different places polyolefin chains, it is also susceptible to polymerization with the formation of homopolymer chains of polar compounds, which are connected, but also partly linked polyolefin. The above-mentioned reaction of the graft copolymerization, the formation of polyolefin chains with functional groups, i.e., the functionalization of polyolefins.

It was found that in many applications, such as metal coating, or providing mutual compatible with the new, reinforced glass where you must use appropriate amounts of the above functionalized polyolefin, the best performance is ensured by the functionalized polyolefins, in which the polar groups are present in many separate parts (educated single monomers or oligomerize chains) are grafted polyolefin chains along the entire length, instead of a small number of long chains attached.

The most simple and effective way of obtaining functionalized polyolefins, free long attached polymer chains, is the use of unsaturated polar compounds, such as maleic anhydride (or the corresponding acid or esters), which are unable to form homopolymers with high molecular weight in the presence of initiators, giving free radicals. The above-mentioned unsaturated polar compounds presented here relate to polimerizuet polar vinyl monomer.

There are various ways to obtain the aforementioned functionalized polyolefins. The above methods can be formulated in the following way:

A) grafting in solution: the, the AK xylene, Dean, Diisobutylene, chlorobenzene) at temperatures typically in the range from 130oC to 150oC;

C) inoculation in the solid state: a polyolefin, a polar monomer and initiator generating free radicals, mixed in dry form at room temperature, and the mixture is then heated to temperatures typically in excess of 130oC;

C) inoculation in the melt: the polar monomer and initiator generating free radicals is added to and mixed with the polyolefin, which is heated until complete melting, during the process in the respective mixers or extruders at temperatures of from 180oC to 150oC.

Method (A) gives functionalityand polyolefine with high homogeneity of the distribution of polar groups, but has the disadvantage of requiring the use and recycling of large amounts of solvents. In addition, the number of monomer, such as maleic anhydride, which can be grafted on the polyolefin is low, usually not more than 3% by weight. If the polyolefin is polypropylene, inoculation using this method associated with significant degradation due to the relatively high operating tempera high temperature vaccinations.

In the method (B) deficiency caused by the use of solvents is eliminated, but the distribution of polar groups in the functionalized polyolefin is less homogeneous. In addition, in the method (B) is also present above the degradation and/or the phenomenon of cross-linkage. In the method (C) high temperatures often cause partial volatilization of the polar monomer, as well as to the aforementioned secondary degradation and/or reaction of cross-linking olefin polymer.

Currently, the method has been found which is suitable for vaccinations depolymerizing polar vinyl monomers, preferably maleic anhydride, homopolymers and copolymers of olefins having 2-10 carbon atoms, and the above-mentioned method involves mixing the above-mentioned homopolymers and copolymers with respectively prepared concentrate and extrusion of mixtures obtained in this way.

Therefore, the present invention provides concentrates in the form of particles of olefin polymer, coated at least on the surface, and possibly inside pores with a mixture of additives, including:

A) from 0.05 to 30% by weight, preferably from 0.2 to 10% by weight, relative to the total weight of the concentrate of about 0.5 to 5% in moles, per (A), the initiator generates free radicals, which are inactive at temperatures below or equal to 70% and perhaps

C) from 0.1 to 5% by weight relative to the total weight of the concentrate of the covering substance.

The above concentrates receive, using a process comprising the following stages:

1) mixing at temperatures in the range of 50oC to 70oC, preferably higher than or equal to 50oC and below 60oC olefin polymer in the form of particles, one or more depolymerizing polar vinyl monomers and initiator generating free radicals, which are inactive at temperatures below or equal to 70oC, and perhaps

2) add a covering substance at the same time or after stage (1).

For mixing in stage (1) you can use any mixer for solid products, such as faucets, operating at either low or high rpm. Components (A), (B) and (C) are introduced into the mixer in the proportions indicated above. When using the mixers with high speed (such as turbomixer), heat generated by the mixing process, it is often enough to achieve temperatures of 50-70oC.

So at the end of the functionalization process, if the polar monomer is maleic anhydride, obtained the best results from the point of view of the distribution of the polar monomer and good quality functionalized polyolefin for applications above.

You can also use other depolymerizing polar vinyl monomers, which are in liquid state at room temperature or have a melting point outside the range of 50-70oC, in combination with maleic anhydride or alternatively to him. Therefore, examples depolymerizing polar vinyl monomers, which can be advantageously used, and, in addition to maleic anhydride can be used monomers selected from C1-C10linear and branched dialkylamino, C1-C10linear and branched dialkylamino, taconova anhydride, C1-C10linear or branched dialkylamino basis of itaconic acid, maleic acid, fumaric acid, basis of itaconic acid and mixtures thereof.

As previously set, when the temperatures reached during stage (1), the initiator radicals inactive, i.e., it essentially does not react with the polyolefin polymer with the formation of radicals along the polymer chains. After stage (1) or at the same time it is possible to add substances which are intended to cover the polymer particles, such as paraffin wax, oil and epoxy resin. It is preferable to add the covering material after stage (1). The above-mentioned substances give the concentrates of the present invention better stability over time and act as solvents for polar vinyl monomers during stage functionalization, preventing thus the volatilization of the aforementioned monomers within the above-mentioned stage.

Specific examples of the above-mentioned substances is MICA, vaseline oil, epoxy resin EPIKOTE 882 supplied to the market by SHELL Chemical Company.

If the vinyl monomers and the generator radicals are at temperatures below or equal to 70oC is not in the liquid state, the adhesion of the above-mentioned additives to the polyolefin is provided covering the substances mentioned above. The concentrates thus obtained was then mixed with polyolefins intended for functionalization, preferably in dry mode and by using the previously described mixer. Polyolefins intended for functionalization, which can be the same as that used for concentrates or other, can be represented in the form of powder, flakes or granules. Functionalization occurs during extrusion of the resulting mixtures. However, the concentrates of the present invention can also be successfully added and in the case when the process uses molten polymers (i.e., when are the final products). In this case, the phase functionalization is carried out in situ. You can also ekstradiroval these concentrates in its pure form, i.e. without the introduction of additional polymer during the process, in particular, when the number of polar vinyl olefin polymer, present in the concentrate.

Stage functionalization can be carried out using any known apparatus suitable for extrusion and mixing of polymer powders or particles in a softened state. The extrusion is performed at temperatures preferably in the range from 180oC to 250oC.

During stage functionalization polimerizuet polar vinyl monomers, already dispersed in the polymer matrix and therefore difficult evaporated imparted along polyolefin chains in the form of uniformly distributed single monomer unit. Since under these conditions the reaction of the grafted polymerization is very effective, you can limit the number of initiator radicals minimum required for the above reaction, thus greatly reducing secondary degradation, the branching circuit and/or cross-linking in the polymeric matrix. The product of the graft polymerization, obtained using the method of the present invention, showing in addition to the above-mentioned optimum adhesive properties and compatibility improved mechanical characteristics and is almost invisible yellow tint. In particular, in accordance with the present invention the floor is to metals and can be reinforced with fiberglass (or other mineral filler, such as talc, calcium carbonate, silicon dioxide and mica), thereby obtaining the product, endowed with good mechanical properties. In addition, the concentrates and/or olefinic polymers, functionalityand using concentrates of the present invention, applicable to obtain composite materials with polar polymers such as polyamides, polyesters and polycarbonates, are endowed with optimum mechanical properties and impact resistance.

Olefin polymers used to obtain concentrates of the present invention in the form of a mass, divided into particles, i.e., in the form of powders> flakes spherical or spheroidal particles, preferably having good or very good surface area (for example 20-300 m2)/g and porosity (e.g., pore volume is in the range from 7% to 50% of the total).

Summarizing, the above-mentioned olefin polymers are chosen from homopolymers and copolymers of olefins with the formula R-CH=CH2or mixtures thereof, where R is a hydrogen atom or an alkyl radical of 1-8 carbon atoms or aryl radical (in particular phenyl). Specifically, the above-mentioned homopolymers and copolymers include:

1) isotacticity crystalline copolymers of propylene with ethylene and/or other-olefins, such as, for example, 1-butene, 1-hexene, 1-octene and 4-methyl-1-penten containing preferably from 98 to 80% propylene by weight.

4) ethylene/ -olefin elastomers and ethylene/ -olefin-diene terpolymer containing small proportions of dienes, where the olefin is preferably selected from propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene and 3 - methyl-1-butene. As dienes most often present in the above-mentioned elastomeric copolymers of butadiene, ethylene-norbornene and 1,4-hexadiene.

5) heterophase polymers, obtained by sequential polymerization, comprising homopolymer fraction of propylene (A), or one of the copolymers of item (3) above, and copolymer fraction (B) obtained from elastomeric copolymers of paragraph (4) above.

The above polymers can be obtained using any known method under high or low pressure in the gas phase, in suspension or in solution in the presence of conventional or high-performance catalysts of the Ziegler-Natta or catalysts based on chromium compounds on the media - silicon dioxide or aluminium oxide, or initiator radicals.

Preferred olefin polymers are floor the volume of particles. The pore volume is determined by the method of mercury absorption, described in EP-A - 0395083.

Particles with a pore volume greater than or equal to 20% can be obtained by using high-performance catalyst of the Ziegler-Natta type, as described in examples 2, 3 and 4, published European patent application EP-A-0395083.

Also preferably, more than 40% of the pores of the polymer particles had a diameter of more than 1 μm. The size of individual polymer particles can be in a wide range from 0.1 to 10 mm, for example.

Polyolefins intended for functionalization with the addition of concentrates of the present invention, preferably selected from the above-mentioned homopolymers and copolymers, however, their morphological characteristics, surface area and porosity are not particularly critical.

To obtain concentrates of the present invention can use any initiator that generates free radicals, and is inactive at temperatures below or equal to 70oC, but preferred those initiators which are, in particular, peroxides or isoprostane having a half-life temperature of 90 to 240oC. time Value of half-life are predisposition, are benzoyl peroxide, peroxide determinable, Dicumyl peroxide, tert-butyl, perbenzoate, 2,5-dimethyl-2,5-bis (tert - BUTYLPEROXY) hexyne-3 or azobisisobutyronitrile.

The amount of concentrate that is added to the polyolefin used for functionalization, clearly depends on the number of vaccinated depolymerizing polar vinyl monomers, which are desirable in the final product. Usually above the number depolymerizing polar vinyl monomers is in the range from 0.03 to 5% by weight of the total weight of the polyolefin plus weight depolymerizing polar vinyl monomers. As an example, the amount of concentrate that you want to use to get above the level of functionalization, ranging from 0.1 to 30, preferably from 0.5 to 30% by weight of the total weight of the polyolefin plus concentrate.

Of course, depending on the concentration of the inoculated depolymerizing polar vinyl monomers, you want to get, and the number depolymerizing polar vinyl monomers present in the concentrates can also be used in some cases, the application of large quantities of the above concentrates.

Post obtaining polyolefins, functionalized in accordance with the present invention and are endowed with the properties of the optimal adhesion to metals (carbon steel). Example 5 relates to the composite reinforced with glass fibers. Example 7 and 8 illustrate the production of composite material based on polyamide and turned into high-impact through heterophase propylene/ethylene copolymers, functionalized in accordance with the present invention. Example 4 comparison shows that the adhesive properties to metals significantly lower, if the olefinic polymer functionalitywith using a different process, not the process of the present invention.

Example 1

The concentrate of the present invention will be received, using the following materials and technology mix:

a) a homopolymer of polypropylene VALTEC 7026/XOS (commercially available from HIMONT Italia S. r.l) with particles of spheroidal shape, with a pore volume equal to 20% of the total volume (defined by measuring the absorption of mercury), compacted to an apparent density = 0,38 g/cm3the fraction insoluble in xylene = 96% by weight, and the index of fusion M. I./L (ASTM D 1238-82) = 20 g/10 min,

(b) maleic anhydride,

C) Trigonox C tert-butylperbenzoate supplied to the market AKZO CHEMIE
oC, index melting M. I. /L = 9 g/10 min,

(e) an ethylene/propylene elastomer, completely soluble in xylene at 25oC, ethylene content = 56% by weight, Mooney viscosity ML+ 4 at 100oC = 40.

In turbomaster (2000 rpm) GENERAL/MEC GTM 110, equipped with submerged probe for continuous monitoring of temperature, introducing a stream of nitrogen 94 parts by weight of polypropylene homopolymer VALTEC 7026/XOS, 1 part by weight of peroxide and 5 parts by weight of maleic anhydride, with constant stirring of the contents in a stream of nitrogen until such time as the temperature due to the mixing reaches 60oC. and Then stirring is interrupted and content allow to cool, thus obtaining maleic anhydride and peroxide concentrate.

The functionalized polyolefin of the present invention receive the following process:

3 parts by weight of the concentrate obtained in the aforementioned manner, mix in the dry (at room temperature) with 97 parts by weight of granulated mixture obtained by extrusion 87 parts by weight of propylene/ethylene statistical copolymer and 10 parts by weight of ethylene/propylene elastomer. The dry composition, policenews and granularit.

The resulting product (Polypropylene adhesive = PPA) is used to cover the metal surface to protect it from corrosion by using the following materials:

- purified emery paper plate made of carbon steel,

- 12-04 Prododin liquid bicomponent epoxy primer, produced by T. I. B.,

- heterophase propylene/ethylene copolymer with an ethylene content = 8% by weight, 14% extracted in xylene at 25oC and M. I./ L = 0.8 g/10 min.

A steel plate was heated up to 80oC and covered with a layer of epoxy primer thickness of about 80 μm, the plate was then heated to 190-200oC and covered with a film of a PPA with a thickness of 400 μm, obtained as described above using plastometer of Brabender PLD 651, equipped with flat film matrix, when 200oC. Then 200oC and use the same methodology is applied heterophase propylene/ethylene copolymer film thickness of approximately 2000 microns. The obtained extruded product by rolling, to bond the various layers to one another and to avoid air bubbles.

Determination of adhesion at 23oC and at 120oC according to method 1 N 30670 (angle signal 90owas held OBR is not separated, but passed into a state of fluidity) and 10 H/mm

Example 2

Ingredients and method are the same as in example 1 except that the granulated mixture is obtained by extrusion of 67 parts by weight of propylene/ethylene statistical copolymer and 30 parts by weight of ethylene/propylene elastomer.

Determination of adhesion at 23oC and 120oC gave the following results, respectively: > 25 H/mm and 9 H/mm

Example 3

Ingredients and method are the same as in example 1, except that the peroxide is Trigonox 101-50 Dpd 2,5-dimethyl-2,5-bis (tert-BUTYLPEROXY)hexane and instead of the ethylene/propylene elastomer is used heterogeneous ethylene/propylene copolymer containing 23oC by weight ethylene and 25% by weight of extractables in xylene at 25oC and with M. I./L = 10 g/10 min. in Addition, the granulated mixture used in this test (97% by weight) obtained by extrusion 48.5 parts by weight of the same statistical copolymer as in example 1 and to 48.5 parts by weight of the above-mentioned heterophase copolymer. The results of adhesion at 23oC and 120oC are respectively the following: > 30 H/mm (strip crossed the example 1, except that the mixing in turbometal performed without exceeding the 25oC. Determination of adhesion at 23oC and 120oC gave very low values, i.e., lower than 1 H/mm

Example 5

0.5 wt parts of the concentrate of the same ingredients as in example 1, except that it is obtained in a high speed mixer at 60oC, was mixed with 30 weight parts of glass fibers CP 713 and 69.5 weight parts of polypropylene homopolymer with index isosymmetric of 96.5% and M. I./L = 11 g/10 min. the mixture is Then ekstragiruyut at 250oC using the Bandera extruder 19 with one screw. The obtained product was analyzed for the following physical and mechanical properties: tensile strength at break (ASTM D 638) = 70,7 MPa HDT (the onset temperature of thermal deformation) at 1820 KPa (ASTM D 648) = 146oC impact strength Izod notched at -20oC (ASTM D 256) = 74,4 j/m, the creep deformation of Flexural (ASTM D 2990) = 1,8% (distance between the supports 4 cm at 120oC for 8 hours with a pressure of 100 kg/cm2).

Example 6

The concentrate obtained by the method of example 1, except that used 92 parts by weight VALTEC 7026/XOS, 5 weight parts of maleic amerimacka W 835 and the mixing continued for a few minutes, then the stirring is stopped and the mixture allowed to cool. to 3.6 parts by weight of thus prepared concentrate is mixed directly into the extruder with 96,4 weight parts of Rigidex HD 6070 HDPE produced by BP with MIE = 3.6 g/10 min (ASTM D 1238), a twin-screw extruder Berstorff, with two supply openings. In the first feeding port which is located at the beginning of the auger, loaded HDPE and the second supply port which is located at a distance approximately equal to 15 times the diameter of the screw, is inserted concentrate and comes into direct contact with molten polyethylene. Screw rotation speed is 250 rpm, and the temperature of the molten polymer is 240oC. Receive adhesive polyethylene in pellet form. The above-mentioned adhesive polyethylene is used for coating a metal surface to protect it from corrosion, using the following materials:

- purified emery paper plates, carbon steel,

- the bi-component liquid epoxy primer OLE produced Veneziani

- adhesive polyethylene

- polyethylene HDPE TNL 6060 produced by Neste with MIE = 0.3 g/10 min.

A steel plate was heated to 70-80oC and covered what about the polyethylene, obtained as described above, a thickness of 300 μm. Plate, coated with adhesive, is heated to about 225oC, and using the same extruder at 250oC get three layers of molten HDPE strips HCPE 6060 thickness of 800 μm, and then applied to the above-mentioned plate. Coated steel plate was pressed by rolling, to bond different layers and to remove air bubbles.

Determination of adhesion is performed on the sample obtained in this way, when the 23oC and 100oC, using the methods described above and obtain the following results: 23 H/mm and 6 H/mm, respectively.

Example 7

The concentrate containing 94 weight parts of heterophase propylene/ethylene copolymer (ethylene content: 22% by weight, the index melting M. I./L = 0.7 g/10 min), 5 parts by weight of maleic anhydride and 1 part by weight of 2,5-dimethyl-2,5-bis(t-BUTYLPEROXY)hexane, get on the technology of example 1. Then 6 weight parts of the above concentrate and 24 weight parts of the above-mentioned heterophase copolymer is introduced into the first hopper, located in the initial part of the extruder BUSS-70, while 70 weight parts of polyamide PA 6 RADILON 6, supplied to the market Radici, having a tensile located in the middle of the extruder. The temperature in the extruder is 200oC between the first and second feeding hopper and 250oC between the second feeding hopper and the output.

Obtained is a composite material having a tensile strength = 42 MPa and impact strength Izod notched at 0oC = 280 j/m

Example 8

6 parts by weight of the concentrate obtained as in example 7, 24 weight parts of heterophase propylene/ethylene copolymer (ethylene content: 22% by weight, the index melting M. I./L = 0.7 g/10 min), and 70 parts by weight of polyamide PA 6 RADILON 6 is introduced into the first hopper of the extruder used in example 7, where they are mixed and extruded at 250oC. Obtained is a composite material having a tensile strength = 43 MPa and impact strength Izod notched at 0oC = 320 j/m

1. Concentrate, suitable for the production of functionalized polyolefins, in the form of particles of olefin polymer selected from homopolymers or copolymers of olefins with the formula R-C=CH2where R is a hydrogen atom or alkyl radical with 1 to 8 carbon atoms, or aryl radical, or mixtures thereof, and these particles are coated on the surface and inside innovage monomer, selected from the group comprising unsaturated cyclic anhydrides and aliphatic diesters or dicyclomine derivatives, and vinyl monomers are depolimerizuet, when they are mixed with particles of these olefin polymers at 50 - 70oSince, in the presence of an initiator of free radicals, which are inactive at temperatures below or equal to 70oC; C) from 0.05 to 30% in moles, per (A), initiator of free radicals, which are inactive at temperatures below or equal to 70oC.

2. Concentrate on p. 1, characterized in that it further comprises from 0.1 to 5% by weight relative to the total weight of the concentrate, covering the substance (S) selected from the group consisting of paraffin waxes, oils and epoxy resins, if (a) and (b) are not liquid at a temperature below or equal to 70oC.

3. Concentrate on p. 1, wherein the olefinic polymer is in the form of spherical particles having a pore volume greater than or equal to 7% of the total volume of particles.

4. Concentrate on p. 3, wherein the olefinic polymer is selected from the group consisting of isotactic or mainly isotactic polypropylene, crystalline copolymers propyl and, linear low density polyethylene or low density polyethylene.

5. Concentrate on p. 1, characterized in that polimerizuet polar vinyl monomer is maleic anhydride.

6. Concentrate on p. 1, characterized in that the initiator radicals has a half-life period of 1 to 60 minutes at a temperature of 90 - 240oC.

7. Concentrate on p. 1, characterized in that the initiator of free radicals chosen from peroxides and isoprostane.

8. Concentrate on p. 2, characterized in that the initiator of free radicals chosen from the group consisting of benzoyl peroxide, tert-butyl of perbenzoate, 2,5-dimethyl-2,5-bis(tert-BUTYLPEROXY)hexane, 2,5-dimethyl-2,5-bis (tert-BUTYLPEROXY)-3-hexyne and azobisisobutyronitrile, di-tert-butylperoxide, dicumylperoxide.

9. A method of obtaining a concentrate on p. 1, namely, that conduct (1): mixing at 50 - 70oWith particles of olefin polymer selected from homopolymers or copolymers of olefins with the formula R-CH=CH2where R is a hydrogen atom or alkyl radical with 1 to 8 carbon atoms, or aryl radical, or mixtures thereof, with (A) 0.05 to 30% by weight relative to the total weight of the concentrate, of one or Eskie anhydrides, their aliphatic diesters or dicyclomine derivatives and (C) 0.05 to 30% in moles, per (A), initiator of free radicals, which are inactive at 50 - 70oC.

10. The method according to p. 9, characterized in that it further adds covering substance selected from the group consisting of paraffin waxes, oils and epoxy resins during or after stage (I).

11. The way functionalization of homopolymers and copolymers of olefins having 2 to 10 carbon atoms, wherein said homopolymers and copolymers are mixed with concentrate on p. 1 and thus obtained mixture ekstragiruyut.

12. The method according to p. 11, characterized in that the concentrate is added to the polyolefin used for functionalization, in an amount of 0.1 - 30% by weight of the total weight of the polyolefin plus concentrate.

13. The way functionalization of homopolymers and copolymers of olefins having 2 to 10 carbon atoms, characterized in that exercise extrusion concentrate on p. 1 in pure form.

14. Functionalized polyolefin obtained by the method of p. 12 and containing 0.03 - 5% by weight of grafted polar vinyl monomers.

15. Functionalized polyolefin under item 14, selected from the grove of propylene with ethylene and/or other olefins, containing 80 to 98% by weight of propylene, high density polyethylene, linear low density polyethylene or low density polyethylene, containing 0.03 - 5% by weight of grafted polar vinyl monomers.

 

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