Plasticiser and polymer composition based thereon

FIELD: chemistry.

SUBSTANCE: polyvinyl chloride composition plasticiser is a product of reaction of dioxane alcohol in a mixture with ethers and formals thereof with toluene diisocyanate. Disclosed also is a polymer composition containing polyvinyl chloride and said plasticiser.

EFFECT: modification of dioxane alcohols of the plasticiser prevents its dewetting and, as a result, reduces weight loss of the plasticiser, and enables to improve plasticising properties of the composition, raise flash point, thermal stability and resistance to thermal-oxidative degradation.

4 cl, 4 tbl


The invention relates to the field of polymeric compositions based on vinyl chloride polymers which can be used in various sectors of the economy, for example, to obtain a film materials, artificial leather, adhesives, binders, coatings, structural materials, cable insulation, medical products, in particular, relates to polymeric compositions containing a plasticizer on the basis of dioxane alcohols and mixtures of these alcohols and their esters and formulae, which are waste products of isoprene.

Use of waste products of isoprene as a plasticizer during processing of emulsion and suspension of polyvinyl chloride (hereinafter PVC) is widely known in the industry. The disadvantage of using such a plasticizer is increased volatility and time variations of the operational properties of compounds, such as loss of elasticity or deterioration of heat resistance.

A mixture of derivatives of 1,3-dioxane, which represents a high-boiling by-product (hereinafter WFP), formed in obtaining 4,4-dimethyl-1,3-dioxane condensation of isobutylene with formaldehyde in the production of isoprene (see Ogorodnikova S. Kaliev, Idlis G.S. isoprene Production. - L.: Chemistry, 1973 p.47, 55-58; Gottlieb EM Waste and by-products of economic production is of funds - raw materials for organic synthesis. M.: Chemistry, 1989, pp.182-183).

Allocated from the runway dioxane alcohols and the fraction with a boiling point 115-160°C With 5-10 mm Hg, containing a mixture of dioxane alcohols, their ethers and formaly known as flotation OXAL (TU 2452-015-48158319-2009), and after further distillation dioxane alcohols are used as plasticizer, known under the trademark of EDOS (TU 2493-003-13004749-93), consisting of polyurethane and polyvinylchloride compositions in the manufacture of linoleum, footwear PVC, oilcloth, artificial leather and other materials.

Plasticizer ADOS and flotation OXAL are transparent oily liquid from yellow to brown color with a characteristic smell. Physico-chemical properties of ADOS and OXAL are shown in table 1.

The main disadvantage of the use of flotation reagent OXAL, ADOS as a plasticizer due to the presence of free dioxane alcohols in which the plasticizer has a high volatility and low thermal characteristics (flash point, thermal stability, resistance to thermal oxidative degradation). On these most important characteristics of these components are significantly inferior to the most widespread phtalates the plasticizer (dioctylphthalate (DOP), the temperature CI the value is 229°C at 4.5 mm Hg, and the flash point 205°C).

Low initial boiling point and low thermal stability polisportiva plasticizer leads to partial evaporation and decomposition of its processing with the formation of formaldehyde, acetaldehyde and somaclonal acid, which significantly impairs the sanitary-Toxicological conditions for the production of plasticized products.

Low flash point (130-140°C) prevents the application of plasticizer on the basis of dioxane alcohols in the processing of the suspension of PVC because of the danger of fire.

Over time, unbound components polisportiva plasticizer begin to migrate to the surface of the finished polymer products, breaking the chemical composition of the compound. In addition, at elevated temperatures or during storage and operation of the evaporation of alcohols leads to the loss in weight of plasticizer and deterioration of mechanical properties.

OXAL or ADOS cannot be used in polyvinyl chloride compositions as a separate plasticizer because it does not provide a sufficient level of operational properties of the obtained materials in terms of thermal stability, stiffness, resistance and environmental friendliness. Therefore, these products are used only as a secondary plasticizer in amounts of 5-30 wt.% from the primary square is tificate) in combination, for example, dioctylphthalate or other ester plasticizers.

Thus, to enable the application of the plasticizer based on the waste products of isoprene (WFP), containing dioxane alcohols, in PVC compositions necessary chemical modification, to stabilize the contents of the components in the finished film.

Known way to prevent sweating of ADOS [1], according to which, in the composition of the plasticizer is encouraged to enter ANTIMIGRAINE additives, for example, petroleum resin. However, the presence of resin adversely affects performance PVC compounds, and the proposed composition and technology of obtaining plasticizer significantly more expensive polymer composition.

There is a method of modifying the waste products of isoprene [2], which includes a mixture of dioxane alcohols and mixtures of these alcohols and their esters and formats by adding substances from the group of cyclic anhydrides, such as maleic anhydride, phthalic anhydride, succinic anhydride, phosphoric anhydride, caprolactam, butyrolactam. The reaction product of the above components is proposed to use as a plasticizer for PVC polymer compositions. This solution is the closest analogue.

A disadvantage of the known is th solution is high, the temperature of the reaction (100-180°C) and long-term modification time (from 2 to 6 hours), that is unacceptable for mass production due to the complexity of the process and large energy consumption.

Objective of the claimed group of inventions is an expansion of the means of plastifitsirovanie polymers, as well as expanding the range of PVC compounds.

Achievable technical result is the elimination of the disadvantages of the known analogues, in particular the simplification of obtaining a plasticizer, reducing energy consumption and the elimination of component migration of plasticizer and losses in its mass. The polymer composition obtained using the proposed plasticizer, has improved performance characteristics, continued for long periods of time, such as thermal stability, elasticity, due to the lack of sweating plasticizer and, therefore, reduce the loss in weight of the compound.

This result is achieved by using a plasticizer for polyvinyl chloride compositions, representing the reaction product dioxane alcohols in the mixture with their ethers and formulae with diisocyanate.

The result is achieved in the polymer composition comprising polyvinyl chloride and a plasticizer containing the reaction product dioxane alcohols in the mixture with their ethers and formulae with toluylenediisocyanate the atom.

In the reaction of diisocyanate with dioxane alcohols formed a mixture of symmetrical and unsymmetrical 2-methyl-(I) and 4-methyl-1,3-phenylenecarbonyl (II)

where R1and R2mean (4,4-dimethyl-1,3-dioxane-5-yl)methyl and (2-(4-methyl-1,3-dioxane-4-yl)ethyl radicals. According to mass spectrometry (IHMS) the total content of these components of the mixture with a molecular weight of 466 may vary from 15 to 30 mass percent.

The possibility of binding of free alcohols can be used to obtain an effective plasticizer for PVC polymer compositions of the following products: waste production of isoprene runway: plasticizer "ADOS (TU 2493-003-13004749-93) and flotation OXAL (TU 2452-015-48158319-2009). As a result, the plasticizer can be used as the primary or sole plasticizer, i.e. without additional (primary) plasticizers without losing the desired properties.

The introduction of the isocyanate in the formulation polisportiva plasticizer leads not only to improvement of technological properties of the composition in comparison with the prototype, but also contributes to its mass. The addition of the plasticizer from 7.5 to 15% of the isocyanate reduces the loss in weight in 2-4 times and to improve the heat resistance of the components is the way peers.

In addition to the main components (PVC, plasticizer, stabilizers) polymer composition may contain various fillers.

Components of PVC and plasticizer according to the invention can be combined in different ratios depending on the requirements of the finished composition, in particular, the ratio may vary within the following limits: 1-100:1. The ratio of ingredients polymeric compositions with fillers can be when based on 100 wt.% PVC: 60-70% modified plasticizer and 30-35% of fillers.

To speed up interaction polisportiva component with the isocyanate can be used catalyst. The preferred catalyst is an aliphatic or aromatic amines. For example, when using 1,4-diazabicyclo[2.2.2]octane (DABCO, triethylenediamine) (TU 6-09-4234-77) reaction time at 100°C is reduced to 3-5 minutes. These conditions of the modification in the presence of a catalyst of triethylenediamine allow the process plastifitsirovanie directly in the processing chain to obtain abs plastic in a hot mixer.

Implementation of the invention can be confirmed by the following examples:

Example 1. In a heated reactor equipped with a stirrer, a load of 100 g of the product of EDOS content dioxane alcohol 15 wt.%, and 0.03 g Treaty is Indiamen. The mixture is heated to 100°C and add cent to 8.85 g of toluylene diisocyanate (TU 113-38-95-90) (the molar ratio of the alcohol and isocyanate is 2:1, mass ratio was 1.69:1). The mixture is stirred at the temperature for 5 minutes. The reaction product is a clear, homogenous, viscous liquid, light brown color, free of mechanical impurities with low specific smell.

Example 2. In a heated reactor equipped with a stirrer, a load of 100 g of flotation reagent OXAL content dioxane alcohol 28 wt.%, and 0.04 g of triethylenediamine. The mixture is heated to 100°C and added 16.5 g of diisocyanate (molar ratio of alcohol and isocyanate is 2:1, mass ratio was 1.69:1). The mixture is stirred at the temperature for 5 minutes. The reaction product is a clear, homogenous, viscous liquid, light brown color, free of mechanical impurities with low specific smell.

Comparative physico-chemical properties of DOP plasticizer, plasticizer, EDOS (contents dioxane alcohols 15 wt.%), the flotation reagent OXAL (contents dioxane alcohols 28 wt.%), and modified dioxane mixtures of alcohols and formula are shown in table 1.

Table 1.
While ately The dioctylphthalate GOST 8728-77Plasticizer "ADOS" THE 2493-003-13004749-93Flotation OXAL THE 2452-015-48158319-2009Examples
AppearanceTransparent colorless liquidClear liquid yellow to brownClear liquid yellow to brownTransparent liquid brownTransparent liquid brown
The flash point in open crucible °C205130-140130150155
Mass fraction of volatile impurities, wt.%0,10,61-30,10,2
Density at 20°C, g/cm30,991,08-1,101,02-1,12 1,081,1
Acid number, mg KOH/g0,10,20,30,10,1

Obtaining polymeric composition without fillers and filled polymer composition is produced in a standard way. First, you mix all powder components (PVC, stabilizers chemical resistance and, optionally, fillers) in a standard mixer with jacket for coolant at 35-40°C for 5 minutes. Then enter the plasticizer - modified mixture of dioxane alcohols and their esters and formulae. All components are mixed at 80-90°C for 15 minutes. Next, the resulting mass "ripen" without stirring at 90°C for 1 hour. Finished weight is recycled or extrusion method (the temperature of the material of the cylinder 120°C, the forming head 75°C), or rolling at 150±2°C for 10 minutes.

The approximate compositions of the polymer composition and polymer-filled compositions are shown in tables 2, 3.

Table 2.
The composition of the polymer composition
ComponentContent, wt.%
PVC brand-7059-M (GOST-14332-78)57,6
The plasticizer on the basis of the modified mixture runway (the content of dioxane alcohols 15%)39,3
Rejonowy sulfate lead (Tossa) (Germany)1,7
Calcium stearate (Germany)1,2
The diphenylolpropane (Suite) (Germany)0,2

Table 3
The composition of the filled polymer composition
ComponentContent, wt.%
PVC brand-7059-M (GOST-14332-78)46,8
The plasticizer on the basis of the modified mixture runway (the content of dioxane alcohols 15%)of 31.8
Rejonowy sulfate lead (Tossa) (Germany)1,4
Calcium stearate (Germany)1,0
The diphenylolpropane (Suite) (Germany)0,2
Mel M-60 THAT 5743-001-22242270-200218,8

Table 4 shows the comparative assessment of physico-chemical properties of filled polymer compositions on the basis of the modified mixture of dioxane alcohols and their esters and formulae (contents dioxane alcohols 15%) with industrial plasticizers.

Table 4.
Physico-chemical properties of polymer compositions on the basis of various plasticizersThe dioctylphthalate GOST 8728-77Plasticizer "ADOS" THE 2493-003-13004749-93The plasticizer on the basis of the modified mixture runway
Volume resistivity, Ohm·cm1,0·10111·1091,5·1010
Weight of plasticizer absorption, g / 100 g PVC (suspension)24-272422
The tensile strength, MPa18 2022
Elongation at break, %280320300
The loss in mass at 160°C for 6 hours, %1,55-72
The preservation of the relative elongation at break after aging at 100°C for 7 days, %957090

The proposed invention in comparison with the prototype allows to reduce the cost of modifying additive synthesis by eliminating costly raw materials, reduce the temperature of the process, to reduce the acid number of the product and the content of volatile (unbound) impurities (see table 1, 4). When chemical modification of dioxane alcohols directly in a mixture of alcohols, their ethers and formulae the proposed solution allows to increase the flash point, thermal stability, resistance to thermal oxidative degradation.

The proposed solution provides the ability to use a plasticizer EDOS in the processing of major brands of PVC (emulsion, suspension) as the primary plasticizer, as well as in combination with other what plastificator.

Polymer composition characterized by a minimal set of features needed to provide a specific result, but not excluding the presence of any other components. This composition can be considered as the basis and to be useful in the production of polyvinyl chloride polymer compositions for various purposes. Products made using the proposed composition, due to the property of the plasticizer, more elastic and have high strength characteristics by maintaining the structure of the material without destroying the high elastic deformation.

Sources of information

1. EN 2177966, publ. 10.01.2002, C08L 27/06, SC 5/04.

2. EN 2263120, publ. 27.10.2005 St, C08F 8/46, C08L 27/06.

1. Plasticizer for polyvinyl chloride compositions, representing the reaction product dioxane alcohols in the mixture with their ethers and formulae with diisocyanate.

2. Polymer composition comprising polyvinyl chloride and a plasticizer, characterized in that the plasticizer contains a reaction product according to claim 1.

3. Polymer composition according to claim 2, characterized in that it contains a filler.

4. Polymer composition according to claim 3, characterized in that it contains components in the following ratio: 100 wt.% PVC contains 70% of the modified plasticizer and 30-35% of the floor is of Italy.


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15 cl, 2 dwg, 2 tbl, 2 ex

FIELD: carbon materials.

SUBSTANCE: invention concerns production of polymer material, which can be employed to manufacture construction-destination porous carbon articles. Polymer composition is filled with hardened phenol-formaldehyde resin and powder-like vanadium complex VO(C36H49O5N2) formed when vanadium is recovered from exhausted process solutions produced in processing of ferrous-metallurgy charge slags as product of reaction between metavanadate and bis-amino-phenol-formaldehyde oligomer. Composition also includes lubricant. Proportions of constituents are the following, wt %: pulverized bakelite 36-43.8, hardened phenol-formaldehyde resin 36-43.8, vanadium complex 10-25, and lubricant 2.4-3.0.

EFFECT: increased strength of porous carbon articles.

1 tbl, 7 ex