DE1232739B - Stabilization of polymers or mixed polymers of halogenated vinyl compounds or of chlorinated paraffins - Google Patents
Stabilization of polymers or mixed polymers of halogenated vinyl compounds or of chlorinated paraffinsInfo
- Publication number
- DE1232739B DE1232739B DEA21572A DEA0021572A DE1232739B DE 1232739 B DE1232739 B DE 1232739B DE A21572 A DEA21572 A DE A21572A DE A0021572 A DEA0021572 A DE A0021572A DE 1232739 B DE1232739 B DE 1232739B
- Authority
- DE
- Germany
- Prior art keywords
- polymers
- vinyl compounds
- chlorinated paraffins
- stabilization
- halogenated vinyl
- 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
- 229920000642 polymer Polymers 0.000 title claims description 5
- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title description 2
- 229920001577 copolymer Polymers 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- CEAVWKAXWLZMFB-UHFFFAOYSA-N dibutyl 2-sulfanylbutanedioate Chemical compound CCCCOC(=O)CC(S)C(=O)OCCCC CEAVWKAXWLZMFB-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000006253 efflorescence Methods 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
Classifications
-
- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
- C08K5/58—Organo-tin compounds containing sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Stabilisieren von Polymerisaten oder Mischpolymerisaten halogenhaltiger Vinylverbindungen oder von chlorierten Paraffinen Chlorhaltige hochmolekulare organische Produkte, insbesondere Polyvinylchlorid und seine Mischpolymerisate, neigen zur Verfärbung in der Hitze und zur Abscheidung kleiner Teilchen an der Oberfläche der aus diesen Produkten hergestellten Formkörper, Erscheinungen, die als Ausblühungen bezeichnet werden.Stabilization of polymers or copolymers containing halogen Vinyl compounds or chlorinated paraffins containing high molecular weight organic chlorine Products, especially polyvinyl chloride and its copolymers, tend to Discoloration in the heat and the deposition of small particles on the surface of the Moldings produced from these products, phenomena that appear as efflorescence are designated.
Gewisse organische Derivate des vierwertigen Zinns, wie Dibutylzinnmaleat und das analoge -laurat, sind bereits als Stabilisatoren für Polyvinylchlorid bekannt, jedoch sind sie nicht genügend wirksam. Sie haben ferner den Nachteil, bei den hohen Temperaturen der Verarbeitung von Polyvinylchlorid nicht ganz stabil zu sein, wodurch Verfärbungen der plastischen Massen bewirkt werden. Dibutylzinnmaleat führt außerdem noch zu Schwierigkeiten bei der Verarbeitung durch Kleben auf den Kalanderflächen. Certain organic derivatives of tetravalent tin, such as dibutyltin maleate and the analogous laurate, are already known as stabilizers for polyvinyl chloride, however, they are not sufficiently effective. They also have the disadvantage of high Processing temperatures of polyvinyl chloride are not quite stable, which means Discoloration of the plastic masses are caused. Dibutyltin maleate also performs still to difficulties in processing due to gluing on the calender surfaces.
Es wurde nun gefunden, daß bestimmte Derivate des vierwertigen Zinns weitaus bessere Stabilisatoren sind. Erfindungsgemäß werden Organozinnverbindungen der allgemeinen Formel R-Sn-X4-worin R eine Alkyl- oder Arylgruppe oder einen hydroaromatischen oder heterocyclischen Rest bedeutet und n für die Zahlen 1 oder 2 oder 3 steht und X den Rest eines Diesters einer Merkaptodicarbonsäure, deren Schwefelatom direkt an das Zinnatom gebunden ist, darstellt, zum Stabilisieren von Polymerisaten oder Mischpolymerisaten halogenhaltiger Vinylverbindungen oder von chlorierten Paraffinen verwendet. It has now been found that certain derivatives of tetravalent tin are far better stabilizers. Organotin compounds are according to the invention of the general formula R-Sn-X4-in which R is an alkyl or aryl group or a hydroaromatic group or heterocyclic radical and n stands for the numbers 1 or 2 or 3 and X is the residue of a diester of a mercaptodicarboxylic acid, the sulfur atom of which is directly is bonded to the tin atom, represents to stabilize polymers or Copolymers of halogenated vinyl compounds or of chlorinated paraffins used.
Das Herstellungsverfahren für diese Verbindungen ist in den Unterlagen des deutschen Patents 1020 337 beschrieben. The manufacturing process for these compounds is in the documents of German patent 1020 337.
Ein Beispiel einer solchen Verbindung ist das Reaktionsprodukt von Dibutylthiomalat und Dibutylzinn oxyd, das der folgenden Formel entspricht: Beispiel 1 100 Gewichtsteile eines Mischpolymerisats aus Vinylchlorid und Vinylacetat, 50 Gewichtsteile Dioctylphthalat und 2 Gewichtsteile der oben als Beispiel erwähnten Verbindung werden 1 Stunde gemischt.An example of such a compound is the reaction product of dibutyl thiomalate and dibutyltin oxide, which corresponds to the following formula: Example 1 100 parts by weight of a copolymer of vinyl chloride and vinyl acetate, 50 parts by weight of dioctyl phthalate and 2 parts by weight of the compound mentioned above as an example are mixed for 1 hour.
Die ganze Masse wird sodann in einen Banburymischer gebracht und 10 Minuten lang auf 150"C erhitzt. Von dort wird sie Walzen, die gleichfalls auf 150"C erhitzt sind, und dann einem Kalander mit drei oder vier Walzen zugeführt. Die Temperatur des Kalanders liegt zwischen 138 und 172"C. Das Mischpolymerisat wird zu einer Folie von 0,1 mm Stärke oder einer anderen Stärke verarbeitet. Diese Folie kann 1 Stunde lang auf 170"C erwärmt werden, ohne daß irgendwelche Verfärbung auftritt; er zeigt gute Lichtbeständigkeit.The whole mass is then placed in a Banbury mixer and 10 Heated to 150 "C for minutes. From there it is rolled, which is also heated to 150" C are heated, and then fed to a calender with three or four rolls. The temperature of the calender is between 138 and 172 "C. The copolymer becomes a film 0.1 mm thick or another thickness processed. This slide can last 1 hour be heated to 170 "C for a long time without any discoloration; it shows good lightfastness.
Beispiel 2 Chloriertes Paraffin mit einem Chlorgehalt von 40°/0 wird 12 Stunden auf 66"C erhitzt und Stickstoff durchgeblasen. Das Paraffin verliert 100/, Chlor. Example 2 Chlorinated paraffin with a chlorine content of 40 ° / 0 is Heated to 66 "C for 12 hours and blown nitrogen through. The paraffin looses 100 /, chlorine.
Wenn demselben Paraffin 301, des im Beispiel 1 erwähnten Stabilisators zugefügt werden, beträgt der Chlorverlust unter sonst gleichen Bedingungen nur etwa 10/,.If the same paraffin 301, the stabilizer mentioned in Example 1 are added, the chlorine loss is only approximately under otherwise identical conditions 10 / ,.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1232739XA | 1952-09-08 | 1952-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1232739B true DE1232739B (en) | 1967-01-19 |
Family
ID=22407697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA21572A Pending DE1232739B (en) | 1952-09-08 | 1953-08-24 | Stabilization of polymers or mixed polymers of halogenated vinyl compounds or of chlorinated paraffins |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1232739B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270799B (en) * | 1953-01-02 | 1968-06-20 | Advance Produktion G M B H Deu | Stabilizing halogen-containing polymers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2606169A (en) * | 1951-02-23 | 1952-08-05 | Ansul Chemical Co | Stabilization of sulfone resins |
| US2618625A (en) * | 1949-08-09 | 1952-11-18 | Advance Solvents & Chemical Co | Resins stabilized with organotin-sulfonamides |
-
1953
- 1953-08-24 DE DEA21572A patent/DE1232739B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618625A (en) * | 1949-08-09 | 1952-11-18 | Advance Solvents & Chemical Co | Resins stabilized with organotin-sulfonamides |
| US2606169A (en) * | 1951-02-23 | 1952-08-05 | Ansul Chemical Co | Stabilization of sulfone resins |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270799B (en) * | 1953-01-02 | 1968-06-20 | Advance Produktion G M B H Deu | Stabilizing halogen-containing polymers |
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