DEF0011196MA - - Google Patents
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- Publication number
- DEF0011196MA DEF0011196MA DEF0011196MA DE F0011196M A DEF0011196M A DE F0011196MA DE F0011196M A DEF0011196M A DE F0011196MA
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- aldehydes
- terephthalic acid
- solvent
- polyester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 229920000728 polyester Polymers 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 239000004014 plasticizer Substances 0.000 claims description 5
- 241000790917 Dioxys <bee> Species 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N methylphenylketone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 229940095076 benzaldehyde Drugs 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- QPKOBORKPHRBPS-UHFFFAOYSA-N Bis(2-Hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N Salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N 1,3-Cyclohexadiene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- LTYLUDGDHUEBGX-UHFFFAOYSA-N 1-(cyclohexen-1-yl)ethanone Chemical compound CC(=O)C1=CCCCC1 LTYLUDGDHUEBGX-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-Formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatoms Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Tag der Anmeldung: 27. Februar 1953 Bekamntgemacht am 2. August 1956Date of registration: February 27, 1953 Published on August 2, 1956
Formstücke, wie Fäden, Folien u. ä., von Polyestern aus Terephthalsäure und aliphatischen Dioxyverbindungen, z. B.vonPolyäthylenglykolterephthalat, werden meistens aus dem Schmelzfluß hergestellt. Daneben interessiert auch die Formgebung aus Lösungen. Es ist zwar bekannt, daß Phenole und Nitrobenzol bei erhöhter Temperatur gute Lösungsmittel für solche Polyester sind, doch sind diese wegen ihrer nachteiligen physiologischen Eigenschaften nicht erwünscht. Es ist ferner bekannt (vgl. z. B. die britische Patentschrift 609 943),. daß ζ. Β. Acetophenon bei ioo° quellend auf Polyäthylenglykolterephthalat wirkt. Die Temperatur, bei der die hochpolymere Substanz in solchen aromatischen Ketonen gelöst wird, liegt aber nach eigenen Untersuchungen unerwünscht hoch (z. B. bei 125° für Acetophenon oder 1500 für Cyclohexenylmethylketon). Moldings, such as threads, foils and the like, of polyesters made from terephthalic acid and aliphatic dioxy compounds, e.g. B. of polyethylene glycol terephthalate, are mostly produced from the melt flow. In addition, the design from solutions is also of interest. Although it is known that phenols and nitrobenzene are good solvents for such polyesters at elevated temperatures, these are undesirable because of their disadvantageous physiological properties. It is also known (see e.g. British patent specification 609 943). that ζ. Β. Acetophenone swells at 100 ° on polyethylene glycol terephthalate. The temperature at which the high polymer substance is dissolved in such an aromatic ketones, but is according to our own investigations undesirably high (eg. As at 125 ° for acetophenone or 150 0 for Cyclohexenylmethylketon).
Es wurde nun gefunden, daß sich Aldehyde von aromatischen und partiell hydrierten aromatischen .Verbindungen sowie von solchen heterocyclischen Verbindungen, die im Ringsystem mindestens eine Kohlenstoffdoppelbindung und Stickstoff als Heteroatom enthalten, gut als Lösungsmittel für die PoIy-It has now been found that aldehydes are aromatic and partially hydrogenated aromatic .Verbindungen and of those heterocyclic compounds that have at least one in the ring system Carbon double bond and nitrogen as a hetero atom, good as a solvent for the poly
■ ■■ ■' 609 577/503■ ■■ ■ '609 577/503
F 11196 IVb/39bF 11196 IVb / 39b
ester aus Terephthalsäure und aliphatischen Dioxyverbindüngen verwenden lassen. Im einzelnen handelt es sich vor allem um die Aldehyde von Benzol, Cyclohexadien, Cyclohexen, Naphthalin, Tetrahydronaphthalin, Diphenyl, Pyridin und Chinolin.esters of terephthalic acid and aliphatic dioxy compounds let use. In particular, these are mainly the aldehydes of benzene, cyclohexadiene, Cyclohexene, naphthalene, tetrahydronaphthalene, diphenyl, pyridine and quinoline.
Die Moleküle können auch mehr als eine Aldehydgruppe enthalten. Sie können ferner noch durch andere Gruppen, besonders durch Hydroxyl-, niedrige Alkyl- niedrige Alkoxy-, Nitro- und/oder Halogengruppen substituiert sein.The molecules can also have more than one aldehyde group contain. You can also by other groups, especially by hydroxyl, low Alkyl, lower alkoxy, nitro and / or halogen groups can be substituted.
Einige der vorgenannten als Lösungsmittel dienende Verbindungen schmelzen erst oberhalb ioo°, so daß bei der Verarbeitung der Lösungen die Gefahr eines Auskristallisierens des Lösungsmittels besteht. In diesen Fällen kann durch Kombination von zwei oder mehreren Verbindungen der,beschriebenen 'Art der Schmelzpunkt erniedrigt werden.Some of the aforementioned compounds serving as solvents only melt above 100 °, so that there is a risk of the solvent crystallizing out when processing the solutions. In these cases can be achieved by combining two or more several compounds of the 'described' type of Melting point can be lowered.
Schließlich können diese Verbindungen auch mit anderen Substanzen, die für sich allein die Polyester nicht oder schlecht lösen, verdünnt werden. Als Verdünnungsmittel· kommen vor allem aromatische oder partiell hydrierte aromatische Verbindungen in Betracht. . ... .Finally, these compounds can also be used with other substances that are alone the polyester do not dissolve or dissolve poorly, be diluted. As a diluent there are mainly aromatic or partially hydrogenated aromatic compounds. . ...
Die so erhaltenen Lösungen eignen sich besonders zur Herstellung von Folien aus den Polyestern, Die Verarbeitung erfolgt' in der üblichen Weise, z. B. durch Verwendung einer Foliengießmaschine.The solutions obtained in this way are particularly suitable for the production of films from the polyesters, Die Processing takes place in the usual way, e.g. B. by using a film casting machine.
Höher als 2500 bei Normaldruck siedende Verbindungen der genannten Art können auch als Weichmachungsmittel für die Polyester verwendet werden. Das Einbringen des Weichmachers in den Polyester erfolgt'zweckmäßigerweise mit einer auf ioo° oder höher geheizten Walze.Compounds of the type mentioned which boil higher than 250 ° at normal pressure can also be used as plasticizers for the polyesters. The plasticizer is expediently introduced into the polyester using a roller heated to 100 ° or higher.
Die Löslichkeitsversuche wurden in der Weise ausgeführt, daß ι g Polyäthylenglykolterephthalat in 100 cm3 Lösungsmittel oder Lösungsmittelgemisch gelöst und sodann die Temperatur, bei der beim Abkühlen die Wiederausscheidung des Polyesters erfolgt, bestimmt wurde. Diese Temperatur wird als Löslichkeitstemperatur bezeichnet. Bei Mischungen beziehen sich die Mischungsverhältnisse auf Gewichtsteile.The solubility tests were carried out in such a way that ι g of polyethylene glycol terephthalate was dissolved in 100 cm 3 of solvent or solvent mixture and then the temperature at which the polyester precipitated again on cooling was determined. This temperature is called the solubility temperature. In the case of mixtures, the mixing ratios are based on parts by weight.
Die spezifische Viskosität des verwendeten Polyesters beträgt in i°/oiger Lösung in Phenol 0,64 bei 500.The specific viscosity of the polyester used is in i ° / o by weight solution in phenol at 50 0.64 0th
Lösungsmittel . LösungstemperaturSolvents. Solution temperature
Benzaldehyd .■."." . 100°Benzaldehyde. ■. "." . 100 °
Salicylaldehyd .. ~<-<?i*'['" 100°Salicylaldehyde .. ~ <- <? I * '['" 100 °
2-Methoxybenzaldehyd 1200 2-methoxybenzaldehyde 120 0
o-Nitrobenzaldehyd . .. ...... ■■·■:■· ■ 50°. ■o-nitrobenzaldehyde. .. ...... ■■ · ■: ■ · ■ 50 °. ■
i-Naphthaldehyd "..... ■■ ■ ioo°i-naphthaldehyde "..... ■■ ■ 100 °
Pyridinaldehyd 8o°Pyridine aldehyde 80 °
Benzaldehyd + Mesitylen, 1:1 1300 Benzaldehyde + mesitylene, 1: 1 130 0
i-Naphthaldehyd + Tetrahydro-i-naphthaldehyde + tetrahydro-
naphthalin, 1:1 i6o°naphthalene, 1: 160 °
3-Oxybenzaldehyd + Acetophenon, 1:1 .;...-:,. 1.. Λ· 8ö°
Terephthaläldehyd + ,Benz- ■3-oxybenzaldehyde + acetophenone, 1: 1.; .. .-: ,. 1 .. Λ · 8ö °
Terephthalaldehyde +, Benz- ■
aldehyd, 1:1 900 aldehyde, 1: 1 90 0
Bei Erhöhung der Konzentration des Polyesters steigt die Löslichkeitstemperatur an. Sie beträgt z. B. bei Benzaldehyd als Lösungsmittel ioo° für i°/oige, iio° für. 5%ige und 130°. für 20°/Oige Lösungen.As the concentration of the polyester increases, the solubility temperature increases. It amounts to z. B. with benzaldehyde as a solvent ioo ° for i ° / o ige, iio ° for. 5% and 130 °. for 20 ° / o solutions.
Eine eventuelle Oxydation der Aldehyde zu den entsprechenden Säuren bei Luftzutritt zu den Lösungen hat keinen großen Einfluß auf die Löslichkeitstemperatur. Zum Beispiel beträgt die Löslichkeitstemperatur einer aus 1 g Polyester, 49,5 g Benzaldehyd und 49,5 g' Benzoesäure bestehenden Lösung iio° oder einer aus 5 g Polyester, 9 g Benzoesäure und 86 g Benzaldehyd bestehende Lösung 1300.A possible oxidation of the aldehydes to the corresponding acids in the presence of air to the solutions has no great influence on the solubility temperature. For example, the solubility of a polyester prepared from 1 g, 49.5 g benzaldehyde and 49.5 g 'is existing benzoic acid solution iio ° or from 5 g Polyester, 9 g of benzoic acid and 86 g of benzaldehyde existing solution 130 0th
Claims (2)
Britische Patentschrift Nr. 609 943.Considered publications:
British Patent No. 609,943.
Family
ID=
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