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Plasticizing of aliphatic polyesters with alkyl esters of dianhydrohexitols

a technology of dianhydrohexitol and polyester, which is applied in the field of plasticizing aliphatic or semialiphatic polyester composition, can solve the problems of increasing the volume of waste and environmental problems, increasing the volume of polyesters, and insufficient mechanical properties for certain uses, and achieves the effect of improving the mechanical properties of aliphati

Inactive Publication Date: 2015-09-01
ROQUETTE FRERES SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The amounts of plastic which are produced and used worldwide have thus significantly increased in recent years, resulting in an increase in the volume of waste and in environmental problems.
However, these polyesters can exhibit a number of disadvantages.
In particular, their mechanical properties may be insufficient for certain uses.
For example, PLA, in particular highly crystalline PLA, exhibits a very low elongation at break at ambient temperature (of the order of a few percent only) and is thus very brittle.
However, a plasticizer used for a certain type of polymer is not necessarily suitable for another type of polymer.
Glycerol trioleate, glycerol decanoate, propylene glycol, glycerol trihexanoate, glycerol, triacetin, lactates and citrates, which are known plasticizers for polyvinyl chloride (PVC), do not or insufficiently plasticize PLA, are not compatible with PLA or have an insufficient plasticizing effect.
Furthermore, these esters are not very stable thermally and exhibit a high volatility, which brings a significant loss of the plasticizer during the preparation of the plasticized PLA composition.
Thus, none of the current solutions is entirely satisfactory for the plasticization of aliphatic or semi-aliphatic polyesters.
Furthermore, another problem of the products manufactured from these polyesters is the level of sound nuisance which can accompany their use.
This is because, during the handling of the product by the final consumer, the noise created can be very loud, this particularly being the case when said product comprises sheets or films of these polyesters, which are generally the case with packagings.
By way of example, as a result of the dissatisfaction of consumers, Frito Lay® in 2010 had to withdraw bags of chips which they had placed on the American market and which were packaged in material produced from PLA because the noise was too great when the consumer of the chips opened or handled the bag.
Similar problems could also be observed in plants for the manufacture of articles made of PLA, in particular when these objects are obtained by extrusion.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Plasticization of the Aliphatic and Semi-Aliphatic Polymers: Sensory Evaluation and Change in the Glass Transition Temperature

[0157]Products Used

[0158]Polymers Used[0159]PLA 1: Poly(lactic acid), grade 6302D (NatureWorks), Mw=170 000 g / mol[0160]PCL: Polycaprolactone, Capa® 650 (Solvay)[0161]PBAT: Poly(butylene adipate terephthalate), Ecoflex FBX 7011 (BASF)[0162]PBS: Poly(butylene succinate), EnPol G4560J (IRe Chemical)[0163]PET: Poly(ethylene terephthalate), Lighter C93 (Equipolymers)[0164]PBT: Poly(butylene terephthalate), Valox 325F (Sabic)[0165]PS: Crystal polystyrene, PS 500 (Sabic)

[0166]Plasticizers:[0167]IDE (plasticizer used in the invention): isosorbide dialkyl ester (C7 alkyl groups)[0168]DINP: Diisononyl phthalate (Sigma-Aldrich)[0169]Jayflex Dina Z: Diisononyl adipate (Exxon-Mobil)[0170]Diplast TM ST: Trimellitate (Polynt)

[0171]Preparation of the Compositions

[0172]A Rheomix 600 (Haake) kneader with a capacity of 120 cm3 equipped with cylindrical rotors is used to prepare...

example 2

Plasticization of PLA: Determination of the Mechanical Properties

[0191]Products Used[0192]Polymer used[0193]PLA 2: Poly(lactic acid), grade 3051 D (NatureWorks), Mw=95 000 g / mol[0194]Plasticizers:[0195]IDE (plasticizer used in the invention): Isosorbide di(C7)ester;[0196]PEG 400: Polyethylene glycol with a molecular weight of 400 g / mol (Sigma-Aldrich);[0197]Triacetin (Sigma-Aldrich).

[0198]Preparation of the Compositions

[0199]Use is made, in preparing these compositions, of a TSA EMP 26-40 corotating twin-screw extruder (TSA Industriale Srl), the extrusion being carried out with a die with a diameter of 3 cm.

[0200]The different plasticizers are blended with the PLA in proportions by weight of table 4.

[0201]The preparation conditions are as follows:[0202]Temperature profile: 170° C. (for the 8 heating zones)[0203]Die head temperature: 170° C.[0204]Introduction of the plasticizer via a metering pump into the inlet zone and then introduction of the polymer into zone 3 via a side feeder[...

example 3

Plasticization of Aliphatic and Semi-Aliphatic / Semi-Aromatic Polyester Blends: Determination of the Mechanical Properties

[0229]Products Used[0230]Blend of polyesters: Ecovio® (BASF), consisting of a blend of PBAT (55% by weight) and of PLA (45% by weight);[0231]IDE (plasticizer used in the invention): isosorbide di(C7)ester.

[0232]The compositions are prepared according to the same protocol as that of example 2. In the same way, the properties are measured using the same measurement conditions as example 2.

[0233]The properties obtained for the blends of polyester with IDE are presented in table 5.

[0234]

TABLE 5Effect of the incorporation of a plasticizer on the mechanicalproperties and the glass transition temperature of the blends of polyestersYoung's Elongation Tensile PlasticizerflexuralatstrengthTgcontentmodulus (MPa)break (%)(Mpa)(2nd heating)0%1100.23403.3620.9−34° C. and 56° C.12.5% IDE464.30655.0817.11−40° C. and 40° C.

[0235]These tests show that IDE indeed has a plasticizing ...

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Abstract

A composition includes: at least one aliphatic or semi-aliphatic polyester containing at least 70 mol % of saturated aliphatic units, whereby the units can be obtained by polycondensation of monomers selected from among saturated hydroxyalkanoic acids having formula HO—CxH2x—COOH, saturated dicarboxylic acids having formula HOOC—CxH2x—COOH, and saturated diols having formula HO—CxH2x—OH, wherein x=1-20, preferably 1-6, the rest of the units being formed by aromatic units; and at least one alkyl ester of 1,4:3,6-dianhydro hexitol selected from among alkyl monoesters and alkyl diesters of isosorbide, isomannide and isoidide. A a method for producing one such composition and to the different uses of one such composition are also described.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]A subject matter of the invention is an aliphatic or semi-aliphatic polyester composition plasticized by a specific diol ester. Another subject matter of the invention is a process for manufacturing said composition and uses of this composition. Another subject matter of the invention is the use of this diol ester as plasticizer for an aliphatic or semi-aliphatic polyester.[0003]2. Description of the Related Art[0004]The use of plastics has become widespread in numerous applications. The amounts of plastic which are produced and used worldwide have thus significantly increased in recent years, resulting in an increase in the volume of waste and in environmental problems.[0005]In order to facilitate the removal of this plastic waste, biodegradable polymers are forming the subject of very particular interest.[0006]Mention may be made, as an example of biodegradable polymer, of “biodegradable polyethylene”, which is in rea...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08K5/11C08K5/12C08K5/1535
CPCC08K5/12C08K5/11C08K5/1535
Inventor COUDYSER, LAURIESABRE, PHILIPPE
Owner ROQUETTE FRERES SA