DE1014321B - Process for the production of moldings, coatings and putties made of modified polyesters that are resistant to alkalis and solvents - Google Patents

Process for the production of moldings, coatings and putties made of modified polyesters that are resistant to alkalis and solvents

Info

Publication number
DE1014321B
DE1014321B DEF18824A DEF0018824A DE1014321B DE 1014321 B DE1014321 B DE 1014321B DE F18824 A DEF18824 A DE F18824A DE F0018824 A DEF0018824 A DE F0018824A DE 1014321 B DE1014321 B DE 1014321B
Authority
DE
Germany
Prior art keywords
alkalis
solvents
hydroxyl groups
coatings
resistant
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.)
Pending
Application number
DEF18824A
Other languages
German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE552520D priority Critical patent/BE552520A/xx
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DEF18824A priority patent/DE1014321B/en
Priority to CH3938256A priority patent/CH370919A/en
Priority to FR1160217D priority patent/FR1160217A/en
Priority to GB3456656A priority patent/GB845529A/en
Publication of DE1014321B publication Critical patent/DE1014321B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6858—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/68—Unsaturated polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/06—Unsaturated polyesters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

DEUTSCHESGERMAN

Die Herstellung von ungesättigten Polyestern und deren Polymerisationsprodukten mit Styrol unter dem Einfluß von Peroxydkatalysatoren ist bekannt, ebenso die Herstellung von freien Isocyanatgruppen aufweisenden modifizierten Polyestern und deren Polymerisationsprodukten mit Styrol unter dem Einfluß von Peroxydkatalysatoren.The production of unsaturated polyesters and their polymerization products with styrene under the The influence of peroxide catalysts is known, as is the production of free isocyanate groups modified polyesters and their polymerization products with styrene under the influence of Peroxide catalysts.

Es wurde nun gefunden, daß Mischungen von an sich bekannten ungesättigten, nicht isocyanatmodifizierten Polyestern und an sich bekannten freie Isocyanatgruppen aufweisenden, isocyanatmodifizierten, ungesättigten Polyestern in den üblichen Lösungen in Styrol bei der durch Peroxyde katalysierten Polymerisation unter folgenden Voraussetzungen zu chemisch besonders resistenten Produkten führen.It has now been found that mixtures of unsaturated, non-isocyanate-modified, known per se Polyesters and isocyanate-modified, unsaturated polyesters known per se and containing free isocyanate groups in the usual solutions in styrene in the polymerization catalyzed by peroxides among the following Conditions lead to products that are particularly chemically resistant.

Die Mischungen der ungesättigten Polyester müssen entweder äquimolar, bezogen auf freie OH-Gruppen des ungesättigten Polyesters und die freien Isocyanatgruppen des Isocyanatgruppen aufweisenden Polyesters, oder mit einem bis zu 33°/0igen Überschuß von Isocyanatgruppen ao oder mit einem bis zu 200°/0igen Überschuß an Hydroxylgruppen vorliegen. Der Carboxylgruppengehalt soll dabei an sich so gering wie möglich sein.The mixtures of the unsaturated polyester must either in equimolar amounts, based on free OH groups of the unsaturated polyester and the free isocyanate groups of the isocyanate group-containing polyester, or with an up to 33 ao ° / 0 by weight excess of isocyanate groups or with an up to 200 ° / 0 igen excess of hydroxyl groups are present. The carboxyl group content should be as low as possible.

Die chemische Widerstandsfähigkeit der erfindungsgemäß erhaltenen Produkte gegen Alkalien und Lösungsmittel ist besonders hoch, ohne daß die gute Resistenz normaler Polyester-Styrol-Polymerisationsprodukte gegen Säuren und Oxydantien verringert wird. Dies war nicht zu erwarten, da sowohl die Polymerisate ungesättigter Polyester mit Styrol wie diejenigen isocyanatgruppenhaltiger Polyester mit Styrol für sich allein weder gegen Lösungsmittel, insbesondere Aceton, noch gegen Alkalien gut beständig sind. Am besten sind die Resultate, wenn man ungesättigte Polyester verwendet, in denen sowohl die Zahl der freien Hydroxylgruppen als auch die der freien Isocyanatgruppen 0,01 bis 5% des Polyestergewichtes ausmachen. Jedoch können diese Mengenverhältnisse auch über- oder unterschritten werden.The chemical resistance of the products obtained according to the invention to alkalis and solvents is particularly high without the good resistance of normal polyester-styrene polymerization products against Acids and oxidants is reduced. This was not to be expected, as both the polymers were more unsaturated Polyester with styrene such as those polyesters containing isocyanate groups with styrene alone neither against Solvents, especially acetone, still have good resistance to alkalis. The results are best when one uses unsaturated polyester in which both the number of free hydroxyl groups and that of the free isocyanate groups make up 0.01 to 5% of the weight of the polyester. However, these proportions can can also be exceeded or undercut.

Ferner ist es vielfach zweckmäßig, dem Polymerisationsgemisch noch chemisch inerte Füllstoffe, wie Quarzmehl, Schwerspat, Koksmehl, Graphit, Siliciumcarbid, Titandioxyd, zuzusetzen, mit deren Hilfe sich z. B. die Wärmeleitfähigkeit und die Ausdehnung von Überzügen, Kittstellen oder Formkörpern, wie Rohre, Platten, Schalen, die sich nach bekannten Methoden erhalten lassen, aus den erfindungsgemäßen Massen regeln läßt. In den folgenden Beispielen 1 bis 3, sind die bekannten Produkte (Beispiel 1) und die nach einem älteren nicht zum Stande der Technik gehörenden Verfahren (Beispiel 2) den erfindungsgemäß erhaltenen Produkten (Beispiel 3) gegenübergestellt.Furthermore, it is often expedient to add chemically inert fillers, such as Quartz powder, barite, coke powder, graphite, silicon carbide, titanium dioxide, to be added, with the help of which z. B. the thermal conductivity and the expansion of coatings, putty or molded bodies, such as pipes, Plates, dishes, which can be obtained by known methods, regulate from the compositions according to the invention leaves. In the following Examples 1 to 3, the known products (Example 1) and those according to a older processes not belonging to the state of the art (Example 2) the products obtained according to the invention (Example 3) compared.

Beispiel 1
30 Teile einer Lösung, die 30 Teile Styrol und 70 Teile Verfahren zur Herstellungexample 1
30 parts of a solution containing 30 parts of styrene and 70 parts of method of preparation

von gegen Alkalien und Lösungsmittel widerstandsfähigen Formkörpern,of moldings resistant to alkalis and solvents,

Überzügen und KittstellenCoatings and putties

aus modifizierten Polyesternmade of modified polyesters

Anmelder:Applicant:

Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft

vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,

Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45

eines ungesättigten Polyesters, aufgebaut aus Phthalsäure, Maleinsäure und 1, 3-Butylenglykol, enthält und bei der die Zahl der freien Hydroxylgruppen festliegt und die Zahl der freien Carboxylgruppen verschwindend gering ist, werden unter Zusatz von 2 °/0 einer Paste, bestehend aus gleichen Teilen Dibutylphthalat und Benzoylperoxyd und 0,01 % Dimethylanilin, mit 100 Teilen Quarzmehl gemischt. Die Mischung wird in Glasrohre von 25 mm Höhe und 25 mm Durchmesser gefüllt. Sie ist nach 2 Stunden völlig erhärtet und wird nach Entfernen aus dem Glasrohr noch 6 Stunden im Ofen bei 60° auspolymerisiert. Kocht man die so erhaltenen Körper 8 Stunden in folgenden Agenzien am Rückflußkühler, so ergeben sich die nachstehend aufgeführten Gewichtsverluste :an unsaturated polyester composed of phthalic acid, maleic acid, and 1, 3-butylene glycol contains, and in which is fixed, the number of free hydroxyl groups and the number of free carboxyl groups is negligible, are the same with the addition of 2 ° / 0 of a paste consisting of Parts of dibutyl phthalate and benzoyl peroxide and 0.01% dimethylaniline, mixed with 100 parts of quartz flour. The mixture is poured into glass tubes 25 mm high and 25 mm in diameter. It is completely hardened after 2 hours and, after being removed from the glass tube, polymerized for a further 6 hours in an oven at 60 °. If the bodies obtained in this way are boiled for 8 hours in the following agents on the reflux condenser, the following weight losses result:

Natronlauge 12 %Caustic soda 12%

Aceton 8 %Acetone 8%

Salzsäure 1,2%Hydrochloric acid 1.2%

Salpetersäure 4 °/0 Nitric acid 4% / 0

Beispiel 2Example 2

30 Teile einer Lösung, die erhalten wurde durch Vermischen von 30 Teilen Styrol und 70 Teilen eines Polyesters, der neben Resten gesättigter und ungesättigter Säuren solche von Urethanen enthält, die durch Umsetzen von einfachen Glykolen mit Diisocyanaten, beispielsweise30 parts of a solution obtained by mixing 30 parts of styrene and 70 parts of a polyester, which contains, in addition to residues of saturated and unsaturated acids, those of urethanes that are produced by reaction of simple glycols with diisocyanates, for example

709 658/436709 658/436

IOIO

2,6-Toluylendiisocyanat, entstanden sind und die so viel freie Isocyanatgruppen enthalten, um die freien Hydroxydgruppen des normalen Polyesters in äquimolaren Mengen zu binden, werden mit 2% einer Paste von der gleichen Zusammensetzung wie in Beispiel 1 angegeben, versetzt, diese Mischung ebenfalls nach den Angaben im Beispiel 1 weiterbehandelt und auf ihre Chemikalienfestigkeit und Lösungsmittelbeständigkeit untersucht. Dabei wurden folgende Gewichtsverluste erhalten:2,6-tolylene diisocyanate, and which are so much Contain free isocyanate groups to the free hydroxide groups of normal polyester in equimolar amounts To bind quantities are indicated with 2% of a paste of the same composition as in Example 1, added, this mixture is also treated further according to the information in Example 1 and its chemical resistance and solvent resistance investigated. The following weight losses were obtained:

Natronlauge 8 %Caustic soda 8%

: Aceton , 7,8%: Acetone, 7.8%

Salzsäure 1,2%Hydrochloric acid 1.2%

Salpetersäure 4 %Nitric acid 4%

Beispiel 3Example 3

15 Teile der im Beispiel 1 beschriebenen Lösung des Polyesters in Styrol und 15 Teile einer Lösung, bestehend aus 30 Teilen Styrol und 70 Teilen eines Polyesters, der neben Resten gesättigter und ungesättigter Säuren solche von Urethanen, die durch Urr.sstzen von einfachen Glykolen mit Diisocyanaten (etwa Toluylen-di-isocyanat) entstanden sind, und der so viel freies Diisocyanat (etwa 2, 6 Toluylen-di-iso-cyanat) enthält, um die freien Hydroxylgruppen des normalen Polyesters in äquimolaren Mengen zu binden, werden mit 100 Teilen Quarzmehl gemischt, wie im Beispiel 1 beschrieben mit Katalysatoren versetzt, polymerisiert und zur Prüfung der Beständigkeit in den im Beispiel 1 angegebenen Agenzien 8 Stunden15 parts of the solution of the polyester in styrene described in Example 1 and 15 parts of a solution, consisting from 30 parts of styrene and 70 parts of a polyester, which in addition to residues of saturated and unsaturated acids such of urethanes, which are produced by the original composition of simple glycols with diisocyanates (e.g. toluene di-isocyanate) have arisen, and the so much free diisocyanate (about 2.6 toluene di-iso-cyanate) contains the free hydroxyl groups to bind the normal polyester in equimolar amounts, are mixed with 100 parts of quartz flour, As described in Example 1, added with catalysts, polymerized and to test the resistance in the agents given in Example 1, 8 hours

am Rückfluß gekocht. Man stellt nachfolgende Gewichtsverluste fest:refluxed. The following weight losses are observed:

Natronlauge 0,3 %Caustic soda 0.3%

Aceton 0,9%Acetone 0.9%

Salzsäure 0,8%Hydrochloric acid 0.8%

Salpetersäure 1.5%Nitric acid 1.5%

Claims (3)

Patentansprüche-Patent claims 1. Verfahren zur Herstellung von gegen Alkalien und Lösungsmittel widerstandsfähigen Formkörpern, Überzügen und Kittstellen aus modifizierten Polyestern, dadurch gekennzeichnet, daß man die Lösung eines Gemisches aus Umsetzungsprodukten ungesättigter Polyester mit einem Überschuß an Di- oder Polyisocyanaten und ungesättigten Polyestern mit freien Hydroxylgruppen in Styrol verwendet, in dem ein äquimolares Mengenverhältnis von nicht umgesetzten Isocyanat- zu Hydroxylgruppen oder ein Verhältnis mit einem bis zu 33%igen Überschuß an Isocyanat- oder einem bis zu 200%igen Überschuß an Hydroxylgruppen vorliegt.1. Process for the production of moldings resistant to alkalis and solvents, Coatings and putties made from modified polyesters, characterized in that the solution a mixture of reaction products of unsaturated polyester with an excess of di- or Polyisocyanates and unsaturated polyesters with free hydroxyl groups in styrene are used in the an equimolar quantitative ratio of unreacted isocyanate to hydroxyl groups or a Ratio with up to 33% excess of isocyanate or up to 200% excess present on hydroxyl groups. 2. Ausführungsform nach Anspruch 1, dadurch gekennzeichnet, daß die freien Hydroxylgruppen und die freien Isocyanatgruppen je zwischen 0,01 und 5% der eingesetzten ungesättigten Polyester betragen.2. Embodiment according to claim 1, characterized in that the free hydroxyl groups and the free isocyanate groups are each between 0.01 and 5% of the unsaturated polyesters used. 3. Ausführungsform nach Anspruch 1 und 2, dadurch gekennzeichnet, daß dem Gemisch noch chemisch inerte Füllstoffe zugesetzt werden.3. Embodiment according to claim 1 and 2, characterized in that the mixture is still chemically inert fillers are added. In Betracht gezogene Druckschriften:
Deutsche Patentschrift Nr. 940 018.Considered publications:
German patent specification No. 940 018. © 709 658/436 8.57© 709 658/436 8.57
DEF18824A 1955-11-10 1955-11-10 Process for the production of moldings, coatings and putties made of modified polyesters that are resistant to alkalis and solvents Pending DE1014321B (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE552520D BE552520A (en) 1955-11-10
DEF18824A DE1014321B (en) 1955-11-10 1955-11-10 Process for the production of moldings, coatings and putties made of modified polyesters that are resistant to alkalis and solvents
CH3938256A CH370919A (en) 1955-11-10 1956-11-08 Process for the production of polyester-styrene copolymers
FR1160217D FR1160217A (en) 1955-11-10 1956-11-09 Compositions capable of curing and their manufacture
GB3456656A GB845529A (en) 1955-11-10 1956-11-12 Compositions capable of hardening and a process of preparing hardened products therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF18824A DE1014321B (en) 1955-11-10 1955-11-10 Process for the production of moldings, coatings and putties made of modified polyesters that are resistant to alkalis and solvents

Publications (1)

Publication Number Publication Date
DE1014321B true DE1014321B (en) 1957-08-22

Family

ID=7089097

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF18824A Pending DE1014321B (en) 1955-11-10 1955-11-10 Process for the production of moldings, coatings and putties made of modified polyesters that are resistant to alkalis and solvents

Country Status (5)

Country Link
BE (1) BE552520A (en)
CH (1) CH370919A (en)
DE (1) DE1014321B (en)
FR (1) FR1160217A (en)
GB (1) GB845529A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1126602B (en) * 1960-05-11 1962-03-29 Hoechst Ag Process for the production of molded bodies, coatings and putties by curing solutions of unsaturated polyester urethanes in styrene
DE1153160B (en) * 1959-04-17 1963-08-22 Beck & Co G M B H Dr Process for the production of elastic to tough plastics with shaping
DE1290714B (en) * 1965-06-02 1969-03-13 Asea Ab Method for producing a molding compound for the production of molded bodies

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE940018C (en) * 1954-04-13 1956-03-08 Bayer Ag Process for the production of copolymers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE940018C (en) * 1954-04-13 1956-03-08 Bayer Ag Process for the production of copolymers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1153160B (en) * 1959-04-17 1963-08-22 Beck & Co G M B H Dr Process for the production of elastic to tough plastics with shaping
DE1126602B (en) * 1960-05-11 1962-03-29 Hoechst Ag Process for the production of molded bodies, coatings and putties by curing solutions of unsaturated polyester urethanes in styrene
DE1290714B (en) * 1965-06-02 1969-03-13 Asea Ab Method for producing a molding compound for the production of molded bodies

Also Published As

Publication number Publication date
FR1160217A (en) 1958-07-09
BE552520A (en)
GB845529A (en) 1960-08-24
CH370919A (en) 1963-07-31

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