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(12) Patent Application Publication (10) Pub. No.: US 2017/004.4352 A1 STORZUM Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2017/004.4352 A1 STORZUM Et Al US 2017004.4352A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2017/004.4352 A1 STORZUM et al. (43) Pub. Date: Feb. 16, 2017 (54) PLASTICIZER COMPOSITION WHICH (30) Foreign Application Priority Data CONTAINS FURAN DERVATIVES AND Apr. 24, 2014 (EP) .................................... 1416766.8 TEREPHTHALIC ACID DALKYL ESTERS Publication Classification (71) Applicant: BASF SE, Ludwigshafen (DE) (51) Int. Cl. CSK 5/535 (2006.01) (72) Inventors: Uwe STORZUM, League City, TX CSK 5/12 (2006.01) (US); Boris BREITSCHEIDEL, (52) U.S. Cl. Waldsee (DE) CPC ............... C08K 5/1535 (2013.01); C08K 5/12 (2013.01); C08K 2201/014 (2013.01) (21) Appl. No.: 15/305,888 (57) ABSTRACT (22) PCT Filed: Apr. 22, 2015 The invention relates to a plasticizer composition which contains at least one furan derivative and at least one (86). PCT No.: PCT/EP2015/058631 terephthalic acid dialkyl ester, moulding compounds which contain a thermoplastic polymer or an elastomer and said S 371 (c)(1), type of plasticizer composition, and to the use of said (2) Date: Oct. 21, 2016 plasticizer compositions and moulding compounds. Patent Application Publication Feb. 16, 2017. Sheet 1 of 6 US 2017/004.4352 A1 {{}}? ft § {}{}{}& s is edit AssessiAxed go Patent Application Publication Feb. 16, 2017. Sheet 3 of 6 US 2017/004.4352 A1 §.§§ § Patent Application Publication Feb. 16, 2017. Sheet 4 of 6 US 2017/004.4352 A1 Patent Application Publication Feb. 16, 2017. Sheet 5 of 6 US 2017/004.4352 A1 s :gtôi: n ' sis Feb. 16, 2017. Sheet 6 of 6 US 2017/004.4352 A1 :9(613 2. US 2017/004.4352 A1 Feb. 16, 2017 PLASTICZER COMPOSITION WHICH plasticizer only on heating to relatively high temperatures. CONTAINS FURAN DERVATIVES AND The individual isolated polymer aggregates here Swell and TEREPHTHALIC ACID DALKYL ESTERS fuse to give a three-dimensional high-viscosity gel. This procedure is termed gelling, and begins at a certain mini BACKGROUND TO THE INVENTION mum temperature which is termed gel point or salvation 0001. The present invention relates to a plasticizer com temperature. The gelling step is not reversible. position which comprises at least one furan derivative and at 0008 Since plastisols take the form of liquids, these are least one dialkyl terephthalate, to molding compositions very often used for the coating of a very wide variety of which comprise a thermoplastic polymer or an elastomer materials, e.g. textiles, glass nonwovens, etc. This coating is and this plasticizer composition, and to the use of these very often composed of a plurality of sublayers. plasticizer compositions and molding compositions. 0009. In a procedure often used in the industrial process ing of plastisols, a layer of plastisol is therefore applied and then the plastic, in particular PVC, with the plasticizer is PRIOR ART Subjected to incipient gelling above the salvation tempera 0002. Desired processing properties or desired perfor ture, thus producing a solid layer composed of a mixture of mance characteristics are achieved in many plastics by gelled, partially gelled, and ungelled polymer particles. The adding what are known as plasticizers in order to render the next Sublayer is then applied to this incipiently gelled layer, plastics softer, more flexible and/or more extensible. The and once the final layer has been applied the entire structure addition of plasticizers generally serves to shift the thermo is processed in its entirety to give the fully gelled plastics plastic region of plastics to lower temperatures, so as to product by heating to relatively high temperatures. obtain the desired elastic properties at lower processing 0010. Another possibility, alongside production of plas temperatures and lower usage temperatures. tisols, is production of dry pulverulant mixtures of plasti 0003 Production quantities of polyvinyl chloride (PVC) cizer and polymers. These dry blends, in particular based on are among the highest of any plastic. Because this material PVC, can then be further processed at elevated temperatures is versatile, it is nowadays found in a wide variety of for example by extrusion to give pellets, or processed products used in everyday life. PVC therefore has very great through conventional shaping processes, such as injection economic importance. PVC is intrinsically a plastic that is molding, extrusion, or calendering, to give the fully gelled hard and brittle up to about 80°C., and is used in the form plastics product. of rigid PVC (PVC-U) by adding heat stabilizers and other 0011 Plasticizers with good gelling properties are addi additives. Flexible PVC (PVC-P) is obtained only by adding tionally required because of increasing technical and eco Suitable plasticizers, and can be used for many applications nomical demands on the processing of thermoplastic poly for which rigid PVC is unsuitable. mers and elastomers. 0004 Examples of other important thermoplastic poly 0012. In particular in the production and processing of mers in which plasticizers are usually used are polyvinyl PVC plastisols, for example for producing PVC coatings, it butyral (PVB), homo- and copolymers of styrene, polyacry is inter alia desirable to have available, as fast fuser, a lates, polysulfides, and thermoplastic polyurethanes (PUs). plasticizer with low gelling point and low viscosity, these 0005. The suitability of any substance for use as plasti materials being known as fast fusers. High storage stability cizer for a particular polymer depends Substantially on the of the plastisol is moreover also desirable, i.e. the ungelled properties of the polymer to be plasticized. Desirable plas plastisol is intended to exhibit no, or only a slight, viscosity ticizers are generally those which have high compatibility rise over the course of time at ambient temperature. As far with the polymer to be plasticized, give this good thermo as possible, these properties are intended to be achieved by plastic properties, and have only low Susceptibility to loss by addition of a suitable plasticizer with rapid-gelling proper evaporation and/or by exudation (have high permanence). ties, with no need for the use of other viscosity-reducing 0006. There are many different compounds marketed for additives and/or of solvents. plasticizing PVC and other plastics. Phthalic diesters with 0013 However, fast fusers generally often have unsatis alcohols of different chemical structure have in the past often factory compatibility with the polymer/additive mixtures, been used as plasticizers because they have good compat and likewise have unsatisfactory permanence. Another ibility with PVC and advantageous performance character known method for establishing the desired plasticizer prop istics, examples being diethylhexyl phthalate (DEHP). erties is therefore to use mixtures of plasticizers, e.g. at least disononyl phthalate (DINP) and diisodecyl phthalate one plasticizer which provides good thermoplastic proper (DIDP). Short-chain phthalates, e.g. dibutyl phthalate ties but provides relatively poor gelling, in combination with (DBP), diisobutyl phthalate (DIBP), benzylbutyl phthalate at least one fast fuser. (BBP) or diisoheptyl phthalate (DIHP), are also used as fast 0014. There is moreover a requirement to replace at least fusers, for example in the production of what are known as Some of the phthalate plasticizers mentioned in the intro plastisols. It is also possible to use dibenzoic esters, such as duction because these are suspected of being hazardous to dipropylene glycol dibenzoates, for the same purpose along health. This applies specifically to sensitive application side the short-chain phthalates. Phenyl and cresyl esters of sectors such as toys, packaging for food or drink, and alkylsulfonic acids are examples of another class of plasti medical items. cizers with good gelling properties, and are obtainable with 0015 The prior art discloses various alternative plasti trademark MesamollR). cizers with different properties for a variety of plastics and 0007 Plastisols initially are a suspension of finely pull specifically for PVC. Verulant plastics in liquid plasticizers. The Salvation rate of 0016 A plasticizer class that is known from the prior art the polymer in the plasticizer here is very low at ambient and that can be used as alternative to phthalates is based on temperature. The polymer is noticeably solvated in the the cyclohexanepolycarboxylic acids described in WO US 2017/004.4352 A1 Feb. 16, 2017 99/32427. Unlike their unhydrogenated aromatic analogs, 0030 in which these compounds give rise to no toxicological concerns, and 0031 X is *-(C=O)-O-, *-(CH), O , or can be used even in sensitive application sectors. The *—(CH), O (C=O)—, where * represents the corresponding lower alkyl esters generally have rapid-gell point of linkage to the furan ring, and n has the value ing properties. 0, 1, or 2; 0017 WO 00/78704 describes selected dialkylcyclo 0032 and hexane-1,3- and 1,4-dicarboxylic esters for the use as plas 0033 R' and R are mutually independently an ticizer in synthetic materials. unbranched or branched C-alkyl moiety, 0018 U.S. Pat. No. 7,973,194 B1 teaches the use of 0034 b) at least one compound of the general formula dibenzyl cyclohexane-1,4-dicarboxylate, benzyl butyl (II), cyclohexane-1,4-dicarboxylate, and dibutyl cyclohexane-1, 4-dicarboxylate as rapid-gelling plasticizers for PVC. 0019. Another class of plasticizers known from the prior (II) art which may be used as alternatives to phthalates is that of R- O terephthalic esters as described for example in WO 2009/ O95126. 0020. The esters of 2,5-urandicarboxylic acid (FDCA) O O-R are another plasticizer class. 0021 WO 2012/113608 describes C-dialkyl esters of 0035 in which 2.5-furandicarboxylic acid and use of these as plasticizers. I0036) R and R are selected mutually independently These short-chain esters are specifically also suitable for from branched and unbranched C-C2-alkyl moieties. producing plastisols. 0037. The invention further provides molding composi 0022 WO 2012/113609 describes C-dialkyl esters of tions which comprise at least one thermoplastic polymer or 2.5-furandicarboxylic acid and use of these as plasticizers.
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