DE1283514B - Process for changing the mechanical properties of molded vinyl chloride polymer bodies - Google Patents
Process for changing the mechanical properties of molded vinyl chloride polymer bodiesInfo
- Publication number
- DE1283514B DE1283514B DED28974A DED0028974A DE1283514B DE 1283514 B DE1283514 B DE 1283514B DE D28974 A DED28974 A DE D28974A DE D0028974 A DED0028974 A DE D0028974A DE 1283514 B DE1283514 B DE 1283514B
- Authority
- DE
- Germany
- Prior art keywords
- vinyl chloride
- weight
- changing
- mechanical properties
- parts
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/06—Sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08J2327/06—Homopolymers or copolymers of vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES WWW PATENTAMTFEDERAL REPUBLIC OF GERMANY GERMAN WWW PATENT OFFICE
Int. Cl.: Int. Cl .:
Deutsche Kl.: German class:
C08fC08f
39 M- 29/18 39 M- 29/18
45/7245/72
Nummer: 1283 514Number: 1283 514
Aktenzeichen: P 12 83 514.2-43 (D 28974)File number: P 12 83 514.2-43 (D 28974)
Anmeldetag: 17. September 1958 Filing date: September 17, 1958
Auslegetag: 21. November 1968Opening day: November 21, 1968
Es wurde bereits ein Verfahren zur Änderung der mechanischen Eigenschaften von Polyvinylchlorid-Formkörpern vorgeschlagen, nach welchem man Polyvinylchlorid oder Formkörper aus Polyvinylchlorid in der Wärme mit Schwefel und/oder organischen Schwefelverbindungen in Kombination mit primären Di- oder Polyaminen behandelt.There has already been a method for changing the mechanical properties of polyvinyl chloride molded articles proposed according to which one polyvinyl chloride or molded articles made of polyvinyl chloride in the heat with sulfur and / or organic sulfur compounds in combination with primary Treated diamines or polyamines.
Es wurde nun gefunden, daß man mit ausgezeichnetem Erfolg an Stelle der primären Di- oder Polyamine nunmehr auch Schiffsche Basen aus Ketonen ίο oder Aldehyden und aliphatischen Di- oder Polyaminen, die zwei primäre Aminogruppen aufweisen, in Kombination mit Schwefel und/oder organischen Schwefelverbindungen zur Änderung der mechanischen Eigenschaften von Vinylchloridpolymerisat-Formkörpern verwenden kann.It has now been found that in place of the primary di- or polyamines one can with excellent success now also Schiff bases from ketones ίο or aldehydes and aliphatic di- or polyamines, which have two primary amino groups, in combination with sulfur and / or organic Sulfur compounds for changing the mechanical properties of vinyl chloride polymer moldings can use.
Als Ausgangsstoffe für die als Vernetzungsmittel verwendbaren Schiffschen Basen kommen in Betracht einerseits beispielsweise Äthylendiamin, Propylendiamin, Butylendiamin, Hexamethylendiamin, Di- ao äthylentriamin, Tetraäthylenpentamin, Dipropylentriamin; andererseits beispielsweise Aceton, Methyläthylketon, Cyclohexanon, MethyldecylketonAo^-Trimethylundecanon-2, Acetaldehyd, Acrolein, Butyraldehyd, Benzaldehyd, Furfurol, Formaldehyd. asThe starting materials for the Schiff's bases which can be used as crosslinking agents are suitable on the one hand, for example, ethylenediamine, propylenediamine, butylenediamine, hexamethylenediamine, di- ao ethylene triamine, tetraethylene pentamine, dipropylene triamine; on the other hand, for example acetone, methyl ethyl ketone, Cyclohexanone, methyl decyl ketone Ao ^ -trimethylundecanone-2, Acetaldehyde, acrolein, butyraldehyde, benzaldehyde, furfural, formaldehyde. as
Wie bei dem Verfahren gemäß der Patentanmeldung D 28690 IVc/38b können der Schwefel oder die organische Schwefelverbindung und das Vernetzungsmittel in Form einer Lösung verwendet werden, wobei als Lösungsmittel für das Vernetzungsmittel vorteilhaft ein Lösungs- oder Quellungsmittel für das Polymerisat verwendet wird.As in the process according to patent application D 28690 IVc / 38b, the sulfur or the organic Sulfur compound and the crosslinking agent are used in the form of a solution, as Solvent for the crosslinking agent advantageously a solvent or swelling agent for the polymer is used.
Das Verfahren der Erfindung kann so durchgeführt werden, daß man den Schwefel oder die organische Schwefelverbindung und das Vernetzungsmittel gleichzeitig oder nacheinander in das Polymerisat einarbeitet. Man kann auch so vorgehen, daß man das Polymerisat, das auch Weichmacher enthalten kann, zunächst zu einem Formkörper verarbeitet und diesen Formkörper, z. B. in Folienform, mit Lösungen des Schwefels oder der organischen Schwefelverbindung und des Vernetzungsmittels behandelt.The process of the invention can be carried out using the sulfur or the organic The sulfur compound and the crosslinking agent are incorporated into the polymer simultaneously or one after the other. One can also proceed in such a way that the polymer, which can also contain plasticizer, is first added processed a shaped body and this shaped body, for. B. in film form, with solutions of sulfur or the organic sulfur compound and the crosslinking agent.
Als Vinylchloridpolymerisat im Sinne der Erfindung können beispielsweise Polyvinylchlorid, Polyvinylidenchlorid und Mischpolymerisate aus Vinylchlorid und Vinylacetat verarbeitet werden. Man kann auch Gemische verwenden, die Weichmacher, Pigmente, Farbstoffe, Stabilisatoren oder Füllstoffe enthalten.As vinyl chloride polymer for the purposes of the invention, for example polyvinyl chloride, polyvinylidene chloride and copolymers of vinyl chloride and vinyl acetate are processed. You can also use mixtures use that contain plasticizers, pigments, dyes, stabilizers or fillers.
Aus den so behandelten Ausgangsmischungen lassen sich Formkörper beliebiger Art herstellen, z. B. Folien, Rohre, Fäden und Kunstleder. Diese Formkörper haben kautschukelastische Eigenschaften.Moldings of any type can be produced from the starting mixtures treated in this way, e.g. B. Foils, pipes, threads and artificial leather. These moldings have rubber-elastic properties.
Verfahren zur Änderung der mechanischen
Eigenschaften von Vinylchloridpolymerisat-Formkörpern Method of changing the mechanical
Properties of vinyl chloride polymer moldings
Anmelder:Applicant:
Deutsche Gold- u. Silber-Scheideanstalt,German gold and silver refinery,
vormals Roessler, 6000 Frankfurtformerly Roessler, 6000 Frankfurt
Als Erfinder benannt:Named as inventor:
Rudolf Nagelschnidt, 6450 Hanau;Rudolf Nagelschnidt, 6450 Hanau;
Dipl.-Ing. Max Goecke, 6380 Bad HomburgDipl.-Ing. Max Goecke, 6380 Bad Homburg
Beispiel 1
Eine Polyvinylchloridfolie, die ausexample 1
A polyvinyl chloride film made from
65 Gewichtsteilen Polyvinylchlorid,
35 Gewichtsteile Dioctyladipat als Weichmacher, 12 Gewichtsteilen Farbpigmenten,
0,8 Gewichtsteilen Cadmium-stearat als Stabilisator 65 parts by weight of polyvinyl chloride,
35 parts by weight of dioctyl adipate as plasticizer, 12 parts by weight of color pigments,
0.8 parts by weight of cadmium stearate as a stabilizer
zusammengesetzt ist, wird 3 Minuten in eine 4°j^ge Lösung von Mercaptobenzothiazol in Schwefelkohlenstoff und Tetrahydrofuran getaucht, oberflächig abtrocknen gelassen und dann 4 Minuten in eine 2O°/oige Lösung einer Schiffschen Base aus Äthylendiamin und Benzaldehyd, hergestellt durch alkalische Kondensation und Entzug des Reaktionswassers mittels festem Natriumhydroxyd, in Tetrahydrofuran getaucht. is composed, is immersed for 3 minutes in a 4 ° J ^ ge solution of mercaptobenzothiazole in carbon disulfide and tetrahydrofuran, allowed to dry on the surface and then 4 minutes in a 20% solution of a Schiff base of ethylenediamine and benzaldehyde, produced by alkaline condensation and removal of the water of reaction using solid sodium hydroxide, immersed in tetrahydrofuran.
Zur Nachbehandlung wird die Folie 24 Stunden bei 8O0C getempert. Die Folie hat durch diese Behandlung infolge eingetretener Vernetzung weichgummiartigen Charakter erhalten.For the aftertreatment, the foil is annealed for 24 hours at 8O 0 C. As a result of this treatment, the film has acquired a soft rubber-like character as a result of the crosslinking that has occurred.
Je nach dem gewünschten Weichheitsgrad der Folie kann man der Lösung der Schiffschen Base aus dem Diamin und dem Aldehyd oder Keton zur Vermeidung einer zu starken Ausschwemmung des Weichmachers aus der Folie noch Weichmacher zusetzen.Depending on the desired degree of softness of the film, one can use the solution of the Schiff base from the Diamine and the aldehyde or ketone to avoid excessive washing out of the plasticizer add plasticizer from the film.
Ein Gewebe aus Polyvinylidenchlorid, das vollkommen von Fetten und Schlichte befreit wurde, wird gemäß dem Beispiel 1 zuerst in der 4°/0igen Mercaptobenzothiazollösung, jedoch doppelt so lange und dann in eine 50°l^ge Lösung der Schiffschen Base aus Tetraäthylenpentamin und Cyclohexanon, hergestellt nach an sich bekannten Verfahren, in Tetra-A fabric made of polyvinylidene chloride, which was completely freed from fats and size, according to Example 1, first in the 4 ° / 0 sodium Mercaptobenzothiazollösung, but twice as long, and then in a 50 ° l ^ ge solution of the Schiff base of tetraethylenepentamine and cyclohexanone , produced by processes known per se, in tetra
809 638/1633809 638/1633
hydrofuran etwa 10 Minuten getaucht. Durch Wärmebehandlung bei gleichzeitiger Streckung erhält man ein Gewebe, das in seinen Eigenschaften völlig verändert und neuartig ist. Bei gleichzeitiger Steigerung der Zugfestigkeit ist das Gewebe gummielastisch geworden.dipped hydrofuran for about 10 minutes. Heat treatment with simultaneous stretching gives a fabric that has completely changed its properties and is new. With a simultaneous increase the tensile strength, the fabric has become rubbery elastic.
Eine Mischung, die mittels eines Extruders im Spritzgußverfahren verarbeitet werden kann, wird folgendermaßen hergestellt:A mixture that can be processed by injection molding using an extruder is used manufactured as follows:
50 Gewichtsteile50 parts by weight
50 Gewichtsteile50 parts by weight
5 Gewichtsteile5 parts by weight
8 Gewichtsteile
1 Gewichtsteil
0,6 Gewichtsteile
0,3 Gewichtsteile8 parts by weight
1 part by weight
0.6 parts by weight
0.3 parts by weight
Polyvinylchlorid,Polyvinyl chloride,
Dinonyladipat als Weichmacher, lg Dinonyl adipate as a plasticizer, lg
eines in der Gasphase hergestellten Siliziumdioxydaerogels,a silica aerogel produced in the gas phase,
hochaktiver Ruß,highly active soot,
Schwefel,Sulfur,
Thiuramidsulfid,Thiuramide sulfide,
Ammonium-phenyl-äthyl-dithiocarbamat Ammonium phenyl ethyl dithiocarbamate
werden in einem Gummikneter bei einer Maximaltemperatur von 1000C höchstens 30 Minuten lang gemischt. Diese Mischung wird einem Extruder kontinuierlich zugeführt und dabei gleichzeitig eine Lösung bzw. Aufschlämmung von N,N'-Diphenyl-p-phenylendiamin und der Schiffschen Base aus Hexamethylendiamin und Benzaldehyd, wobei das Verhältnis von Hexamethylendiamin zu Benzaldehyd so gewählt wird, daß ein Überschuß des Hexamethylendiamine von mindestens einem halben Mol gegenüber dem Benzaldehyd vorhanden ist, in Weichmacher so zugegeben, daß die Menge der zugesetzten reaktionsfähigen Substanzen nicht mehr als 2 Gewichtsprozent und nicht weniger als 1,6 Gewichtsprozent der Gesamtmischung beträgt.are mixed in a rubber kneader at a maximum temperature of 100 0 C for a maximum of 30 minutes. This mixture is fed continuously to an extruder and at the same time a solution or slurry of N, N'-diphenyl-p-phenylenediamine and the Schiff base of hexamethylenediamine and benzaldehyde, the ratio of hexamethylenediamine to benzaldehyde being chosen so that an excess of the Hexamethylenediamine is present in at least half a mole relative to the benzaldehyde, added in plasticizer so that the amount of reactive substances added is not more than 2 percent by weight and not less than 1.6 percent by weight of the total mixture.
Die Temperatur des Extruders soll dabei in der Schnecke 16O0C nicht übersteigen, sie soll aber in der Düse zwischen 175 und 1800C liegen.The temperature of the extruder is intended to 16O 0 C in the screw not exceed, but should be in the nozzle 175 to 180 0 C.
Die Formlinge sind gummielastisch.The moldings are rubber-elastic.
Benutzt man eine Düse, die ein Granulat erzeugt, so muß dieses innerhalb von 24 Stunden etwa durch Pressen zu Platten oder mit einem Kalander zu einer Folie weiterverarbeitet werden. Vor der Weiterverarbeitung fügt man dem Granulat noch 0,7 Gewichtsteile Bleistearat zur Stabilisierung bei.If you use a nozzle that produces granules, this must be done within 24 hours Pressing them into sheets or using a calender to make a film. Before further processing 0.7 parts by weight of lead stearate are added to the granules for stabilization.
Zur Hersteüung einer Streichpaste für Kunstleder werdenFor the production of a coating paste for artificial leather
60 Gewichtsteüe eines Mischpolymerisats von
Vinylchlorid und Vinylacetat
(97,5:2,5),60 parts by weight of a copolymer of
Vinyl chloride and vinyl acetate
(97.5: 2.5),
40 Gewichtsteüe Dioctylsebacat als Weichmacher,40 parts by weight of dioctyl sebacate as plasticizer,
8 Gewichtsteile Farbpigmente und inerte Füllstoffe, 8 parts by weight of color pigments and inert fillers,
0,6 Gewichtsteüe Schwefel,0.6 parts by weight of sulfur,
0,3 Gewichtsteüe 2-Mercaptobenzothiazol,0.3 parts by weight of 2-mercaptobenzothiazole,
0,2 Gewichtsteüe Ammonium-äthyl-xanthogenat,0.2 part by weight of ammonium ethyl xanthate,
2,2 Gewichtsteüe der Schiffschen Base aus Methyläthylketon und Äthylendiamin2.2 parts by weight of the Schiff base from methyl ethyl ketone and ethylenediamine
0,3 Gewichtsteüe der Schiffschen Base aus Hexamethylendiamin und Butyraldehyd 0.3 parts by weight of the Schiff base from hexamethylenediamine and butyraldehyde
homogen gemischt und etwa 2 Stunden reifen gelassen. Anschließend gibt man noch 1 Gewichtsteü Cadmiumstearat als Stabilisator zu und streicht die Paste auf einen Träger (Gewebe, Vlies, Filz, Papier oder Schaumstoffe). Die Masse wird bei einer Temperatur von bis 18O0C zum Gelieren gebracht. Nach einer kurzen Verweilzeit bei 1000C ist die Beschichtung gummielastisch.mixed homogeneously and left to mature for about 2 hours. Then 1 part by weight of cadmium stearate is added as a stabilizer and the paste is spread on a carrier (fabric, fleece, felt, paper or foam). The mass is brought at a temperature of up to 18O 0 C for gelation. After a short dwell time at 100 ° C., the coating is rubber-elastic.
Claims (1)
USA.-Patentschrift Nr. 2 600 414.Considered publications:
U.S. Patent No. 2,600,414.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED28974A DE1283514B (en) | 1958-08-05 | 1958-09-17 | Process for changing the mechanical properties of molded vinyl chloride polymer bodies |
| CH242062A CH456139A (en) | 1958-08-05 | 1959-07-31 | Process for the production of molded articles of a non-textile type, starting from halogen-containing polyvinyl compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED28690A DE1283513B (en) | 1958-08-05 | 1958-08-05 | Process for changing the mechanical properties of molded polyvinyl chloride articles |
| DED28974A DE1283514B (en) | 1958-08-05 | 1958-09-17 | Process for changing the mechanical properties of molded vinyl chloride polymer bodies |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1283514B true DE1283514B (en) | 1968-11-21 |
Family
ID=25970876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED28974A Pending DE1283514B (en) | 1958-08-05 | 1958-09-17 | Process for changing the mechanical properties of molded vinyl chloride polymer bodies |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1283514B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387305A (en) * | 2014-10-21 | 2015-03-04 | 陕西延长石油矿业有限责任公司 | Preparation method and application of ore dressing collecting agent for multi-metal sulphide ore |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2600414A (en) * | 1947-08-22 | 1952-06-17 | William C Mast | Vulcanization of acrylic resins |
-
1958
- 1958-09-17 DE DED28974A patent/DE1283514B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2600414A (en) * | 1947-08-22 | 1952-06-17 | William C Mast | Vulcanization of acrylic resins |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387305A (en) * | 2014-10-21 | 2015-03-04 | 陕西延长石油矿业有限责任公司 | Preparation method and application of ore dressing collecting agent for multi-metal sulphide ore |
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