DE1226578B - Process for the production of stabilizers for polyvinyl chloride and its copolymers - Google Patents
Process for the production of stabilizers for polyvinyl chloride and its copolymersInfo
- Publication number
- DE1226578B DE1226578B DES85221A DES0085221A DE1226578B DE 1226578 B DE1226578 B DE 1226578B DE S85221 A DES85221 A DE S85221A DE S0085221 A DES0085221 A DE S0085221A DE 1226578 B DE1226578 B DE 1226578B
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- acid
- stabilizers
- copolymers
- polyvinyl chloride
- 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
- 239000003381 stabilizer Substances 0.000 title claims description 27
- 229920001577 copolymer Polymers 0.000 title claims description 6
- 229920000915 polyvinyl chloride Polymers 0.000 title claims description 6
- 239000004800 polyvinyl chloride Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- -1 mercapto compounds Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- VSZSIEBALNXIFG-UHFFFAOYSA-N 2-hydroxyethyl 2,2-bis(sulfanyl)acetate Chemical compound OCCOC(=O)C(S)S VSZSIEBALNXIFG-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 10
- 239000005639 Lauric acid Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- RZBBHEJLECUBJT-UHFFFAOYSA-N 6-methylheptyl 2-sulfanylacetate Chemical compound CC(C)CCCCCOC(=O)CS RZBBHEJLECUBJT-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004801 Chlorinated PVC Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:Int. CL:
C07fC07f
Deutsche Kl.: 12 ο-26/03 German class: 12 ο -26/03
Nummer: 1226 578Number: 1226 578
Aktenzeichen: S 85221IV b/12 οFile number: S 85221IV b / 12 ο
Anmeldetag: 15. Mai 1963 Filing date: May 15, 1963
Auslegetag: 13. Oktober 1966Opening day: October 13, 1966
Die Erfindung betrifft die Herstellung eines Stabilisierungsmittels für Polyvinylchlorid und dessen Copolymere. The invention relates to the production of a stabilizing agent for polyvinyl chloride and its copolymers.
Das erfindungsgemäß hergestellte Stabilisierungsmittel ist auch geeignet für Copolymere von Vinylchlorid und Vinylacetat und Copolymere von Vinylacetat und Vinylidenchlorid und nachchloriertes Polyvinylchlorid. The stabilizing agent prepared according to the invention is also suitable for copolymers of vinyl chloride and vinyl acetate and copolymers of vinyl acetate and vinylidene chloride and post-chlorinated polyvinyl chloride.
Zur Herstellung des Stabilisierungsmittels setzt man erfindungsgemäß Dialkylzinnverbindungen mit Äthylenglykol-di-mercaptoacetat oder Mercaptoessigsäurealkylester und einer Alkansäure und einem Maleinsäuremonoalkylester in an sich bekannter Weise in solchen Mengenverhältnissen um, daß das Stabilisierungsmittel im wesentlichen ausAccording to the invention, dialkyltin compounds with ethylene glycol dimercaptoacetate are used to produce the stabilizing agent or alkyl mercaptoacetate and an alkanoic acid and a maleic acid monoalkyl ester in a manner known per se Convert in such proportions that the stabilizing agent essentially consists of
40 bis 70 % R2Sn(SCH2COOCH2)2 oder40 to 70% R 2 Sn (SCH 2 COOCH 2 ) 2 or
R2Sn(SCH2COOR')2,R 2 Sn (SCH 2 COOR ') 2 ,
15 bis 30% R2Sn(OOCR)2 und ·15 to 30% R 2 Sn (OOCR) 2 and
~ 15 bis 30% R2Sn(OOC · CH = CH · COOR)2 ao ~ 15 to 30% R 2 Sn (OOC • CH = CH • COOR) 2 ao
besteht, wobei in den obigen Formeln R einen Alkylrest und R' einen Alkylrest mit 8 bis 18 C-Atomen bedeutet.consists, where in the above formulas R is an alkyl radical and R 'denotes an alkyl radical having 8 to 18 carbon atoms.
Die vorangehend definierten Substituenten brauchen in den einzelnen Verbindungen nicht identisch zu sein.The substituents defined above need not be identical in the individual compounds.
Als Alkansäuren können besonders verwendet werden: Heptansäure, Stearinsäure, Palmitinsäure, Oleinsäure, Linolsäure, Linolensäure, Ricinolsäure, Behensäure, Myristinsäure und Laurinsäure.Particularly suitable alkanoic acids are: heptanoic acid, stearic acid, palmitic acid, Oleic acid, linoleic acid, linolenic acid, ricinoleic acid, behenic acid, myristic acid and lauric acid.
Erfindungsgemäß wird das Stabilisierungsmittel zwar dadurch hergestellt, daß die Ausgangsverbindungen für die Reaktionsprodukte der obenerwähnten allgemeinen Formeln gleichzeitig und zusammen zur Reaktion gebracht werden. Das Produkt der Umsetzungsreaktionen besteht aber nicht ausschließlich aus diesen Verbindungen.According to the invention, the stabilizing agent is produced in that the starting compounds for the reaction products of the general formulas mentioned above simultaneously and together for Reaction to be brought. However, the product of the conversion reactions is not exclusive from these compounds.
."Nach einer bevorzugten Ausführungsform der Erfindung wird das Stabilisierungsmittel durch gleich^ zeitige Reaktion von Dibutylzinnoxid mit ÄthylengJykolMi-mercaptoessigsäureester, Laurinsäure sowie Maleinsäuremono-2-äthylhexylester, wobei die Mengen der Reaktionspartner entsprechend der weiter oben definierten Mengenbedingung ausgewählt sind, hergestellt. Die für die Reaktion verwendete Organozdnnverbindung kann auch ein Halogenid oder Alkoxid sein.. "According to a preferred embodiment of the The invention is the stabilizing agent by simultaneous reaction of dibutyltin oxide with ethylene glycolMi-mercaptoacetic acid ester, Lauric acid and maleic acid mono-2-ethylhexyl ester, the amounts the reactants are selected according to the quantity condition defined above, manufactured. The organotin compound used for the reaction may also be a halide or an alkoxide be.
Das Stabilisierungsmittel hat nicht nur einen besonders guten Stabilisierungseffekt gegen thermische
Zersetzung, sondern ist auch selbst sehr lagerungsbeständig, d. h., es wird nicht leicht durch Hydrolyse
• oder Polymerisation zerstört und bildet auch keine Verfahren zur Herstellung von
Stabilisierungsmitteln für Polyvinylchlorid
und dessen CopolymereThe stabilizing agent not only has a particularly good stabilizing effect against thermal decomposition, but is also itself very stable in storage, ie it is not easily destroyed by hydrolysis or polymerization and also does not form a process for the production of
Stabilizers for polyvinyl chloride
and its copolymers
Anmelder:Applicant:
Harold Verity Smith,Harold Verity Smith,
La Conversion sur Lutry, Vaud (Schweiz)La Conversion sur Lutry, Vaud (Switzerland)
Vertreter:Representative:
Dr. K. R. Eikenberg und Dipl.-Chem. W. Rücker, Patentanwälte, Hannover, Am Klagesmarkt 10-11Dr. K. R. Eikenberg and Dipl.-Chem. W. Rücker, Patent Attorneys, Hanover, Am Klagesmarkt 10-11
Als Erfinder benannt:Named as inventor:
Harold Verity Smith, ;Harold Verity Smith,;
La Conversion sur Lutry, Vaud (Schweiz) : La Conversion sur Lutry, Vaud (Switzerland) :
Beanspruchte Priorität:Claimed priority:
Großbritannien vom 17. Mai 1962 (19 002)Great Britain dated May 17, 1962 (19 002)
Gele oder Niederschläge. Weiterhin ist es— trotz der bei der Reaktion verwendeten schwefelhaltigen Verbindungen — relativ geruchlos. Darüber hinaus besitzt das Mittel im Gegensatz zu den bekannten Stabilisatoren einen Gleiteffekt, so daß der Kunststoff während der Verarbeitung nicht an den Spritzdüsen oder an den Kalanderwalzen festklebt.Gels or precipitates. Furthermore, it is - despite the sulfur-containing ones used in the reaction Connections - relatively odorless. Furthermore In contrast to the known stabilizers, the agent has a sliding effect, so that the plastic Does not stick to the spray nozzles or the calender rollers during processing.
Außerdem zeigen die Verfahrensprodukte einen inneren Schmiereffekt, durch den Reibungswärme während der Verarbeitung des Kunststoff es stark ver* ringert wird, so daß auch dadurch die thermische Zersetzung herabgesetzt wird. Dies ist von besonderes Bedeutung bei unplastifizierten Vinylchloridpolymeren. - Die Erfindung wird nachfolgend in Ausführungsbeispielen näher beschrieben: : ·.;;'■: In addition, the process products show an internal lubricating effect due to the frictional heat During the processing of the plastic it is greatly reduced, so that the thermal Decomposition is reduced. This is special Significance in unplasticized vinyl chloride polymers. - The invention is described in more detail below in exemplary embodiments:: ·. ;; '■:
.,,.:· B ei spiel 1.,,.:· Example 1
Zur Herstellung des Stabilisierungsmittels werden 505,4 g Di-n-octylzinnoxid, 210 g Äthylenglykol-dimercaptoacetat, 91,2 g Maleinsäure-mono-2-äthylhexylester und 86 g Laurinsäure in 51 Toluol zur Reaktion gebracht. 25,2 g Wasser werden durch azeotrope Destillation entfernt, das Toluol wird durch Vakuumdestillation abgetrieben. Es ergibt sich eine leichtgelbe Flüssigkeit.To prepare the stabilizer, 505.4 g of di-n-octyltin oxide, 210 g of ethylene glycol dimercaptoacetate, 91.2 g of maleic acid mono-2-ethylhexyl ester and 86 g of lauric acid in 51 toluene for Brought reaction. 25.2 g of water are removed by azeotropic distillation, the toluene is by Vacuum distillation driven off. The result is a light yellow liquid.
> :■ : :·■?:.■:■'■< :;; 609670/443>: ■: · ■: ■: ■ '■ <:. ; 609670/443
Zur Herstellung des Stabilisierungsmittels werden 400 g Di-n-butylzinnoxid, 245 g Mercaptoessigsäureisooctylester, 144 g 2-Äthylhexansäure und 228 g Maleinsäure-mono-(2-äthylhexyl)-ester iff 41 Toluol zur Reaktion gebracht. 28,8 g Wasser werden durch azeotrope Destillation entfernt, und das Toluol wird durch Vakuumdestillation abgetrieben.'Es ergibt sich eine leichtgelbe Flüssigkeit.To prepare the stabilizing agent, 400 g of di-n-butyltin oxide, 245 g of isooctyl mercaptoacetate, 144 g of 2-ethylhexanoic acid and 228 g of maleic acid mono- (2-ethylhexyl) ester iff 41 toluene brought to reaction. 28.8 g of water are removed by azeotropic distillation and the toluene becomes driven off by vacuum distillation. A light yellow liquid results.
Zur Herstellung des Stabilisierungsmittels wurden 350 g Di-n-butylzinnoxid, 210 g Äthylenglykol-dimercaptoacetatj 91,2 g Maleinsäure-mono-2-(äthylhexyl)-ester und 80 g Laurinsäure in einem Wasserauskreiser auf 115O,C erhitzt, wobei 25,2 g Wasser entfernt werden. Es ergibt sich eine leichtgelbe Flüssigkeit. ■"'■-'■ -'"'■■■■ ■-'-■■For the preparation of the stabilizing agent, 350 g of di-n-butyltin oxide and heated 210 g Ethylene glycol 91.2 g dimercaptoacetatj maleic acid mono-2- (ethylhexyl) ester and 80 g of lauric acid in a water separator to 115 O, C, wherein 25 2 g of water are removed. The result is a light yellow liquid. ■ "'■ -' ■ - '"' ■■■■ ■ -'- ■■
Beispiel 4 ^ ::- ""5 ■ 'Example 4 ^ :: - "" 5 ■ '
Zur Herstellung des Stabilisierungsmittels werden 350 g Di-n-butylzinnoxid, 204 g Mercaptoessigsäureisooctylester, 105 g Äthylenglykol-di-mercaptoacetat, 80 g Laurinsäure und 91,2 g Maleinsäure-mono-(2-äthylhexyl)-ester in einem Wasserauskreiser erhitzt, wobei 25(2^gcWassei entfernt rwerdem- ,:::. To prepare the stabilizer, 350 g of di-n-butyltin oxide, 204 g of isooctyl mercaptoacetate, 105 g of ethylene glycol di-mercaptoacetate, 80 g of lauric acid and 91.2 g of mono- (2-ethylhexyl) maleic ester are heated in a water separator, with 25 (2 ^ gcWassei removed rwerdem- , :::.
Vergleichsversuche ., ■ - -Comparative experiments., ■ - -
fr:J&rf0lgendeniKQBDtp.QQenteni.100,0 gPVG-Eiunststoff,{Vinnol iYrlöO/55 d®), .0,5. g Stearinsäuremonoglyzerinester und 2,0 g Stabilisierungsmittel, wurden in einem Walzenwerk oder Mischwalzwerk bei 165 0C so lange gemahlen, bis ein Festkleben der Mischung an den Walzen beobachtet wurde. Die Zeitdauer ergab sich für verschiedene Stabilisierungsmittel gemäß der ■--■ nachfolgenden Aufstellung: for : J & rf0lgendiKQBDtp.QQenteni.100.0 gPVG-egg plastic, {Vinnol iYrlöO / 55 d®), .0.5. g of stearic acid monoglycerol ester and 2.0 g of stabilizing agent were ground in a roller mill or mixing roller mill at 165 ° C. until the mixture was observed to stick to the rollers. The period of time for various stabilizing agents resulted from the ■ - ■ following list:
4040
4545
Die Verbindungen wurden weiterhin hinsichtlich ihrer Wärmestabilität durch Alterung in einem Ofen bei 175° C miteinander verglichen. Nach einer Stunde war Mittel Nr. 2 etwas gelber als Mittel Nr. 1 und Mittel Nr. 4 etwas gelber als Mittel Nr. 3.The compounds were further tested for their thermal stability by aging in an oven at 175 ° C compared with each other. After one hour, Agent No. 2 was slightly more yellow than Agent No. 1 and Remedy No. 4 a little more yellow than Remedy No. 3.
Die Verbindungen wurden ebenfalls hinsichtlich ihrer Wärmestabilität in einem Walzwerk in dem folgenden Ansatz miteinander verglichen:The compounds were also tested for their thermal stability in a rolling mill in the compared the following approach:
100,0 g PVC-Runststoff(Geonl01<si),;::i i .
0,75 g Stearinsäuremonoglyzerinester,
0,25 g Behensäure,
1,0 g .. Stabilisierungsmittel. .100.0 g PVC plastic (Geonl01 <si),; :: ii. 0.75 g stearic acid monoglycerol ester,
0.25 g behenic acid,
1.0 g .. stabilizer. .
Die Mischungen wurden bei 1650C vermählen und die Farbentwicklung verglichen. Stabilisierungsmittel Nr. 1 führte zu einem Festkleben nach 45 Minuten, wobei es dann beträchtlich gelber als Nr. 2 war. Nach einer Stunde Bearbeitungszeit war Nr. 3 beträchtlich gelber als Nr. 4.The mixtures were ground at 165 ° C. and the color development compared. Stabilizer # 1 caused sticking after 45 minutes at which point it was considerably more yellow than # 2. After an hour of processing, No. 3 was considerably more yellow than No. 4.
Schließlich wurde auch folgender Versuch ausgeführt: Finally, the following experiment was also carried out:
Die Komponenten 100 g PVC-Kunststoff (Solvic 223®), 0,5 g Stearinsäure und 2 g Stabilisierungsmittel wurden in einem Walzwerk bei 155°C so lange bearbeitet,, bis ein. Festkleben der -Mischung an· den Walzen beobachtet wurde. Für die folgenden Stabil· sierungsmittel betrug die Zeitdauer: .:·. .The components 100 g PVC plastic (Solvic 223®), 0.5 g stearic acid and 2 g stabilizer were processed in a rolling mill at 155 ° C for so long until a. Adhesion of the mixture to · the Rolling was observed. The duration for the following stabilizers was:.: ·. .
StabilisierungsmittelStabilizers
Nr. 1 Stabilisierungsmittel gemäß Beispiel 3 ..."""..'. Λ .,.,.....No. 1 stabilizer according to example 3 ... "" ".. '. Λ.,., .....
Nr. 2 Dibutylzinn -' di - isooctylmer-'"
: captoessigsäureester ..-].'... v..No. 2 dibutyltin - 'di - isooctylmer-'"
: captoacetic acid ester ..-] .'... v ..
Walz. .,. Zeitdauer in-MinutenWaltz. .,. Duration in minutes
Claims (1)
R2Sn(SCH2COORO2,40 to 70 ° / 0 R 2 Sn (SCH 2 COOCH 2 ) 2 or
R 2 Sn (SCH 2 COORO 2 ,
Deutsche Auslegeschriften Nr. 1 020 331,1 020 332, 1 020 333, 1 020 334, 1 020 335, 1 020 336, 1 020 337, 338;Considered publications:
German Auslegeschriften Nos. 1 020 331, 020 332, 1 020 333, 1 020 334, 1 020 335, 1 020 336, 1 020 337, 338;
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19002A GB1008845A (en) | 1962-05-17 | 1962-05-17 | Polymer stabilizer and polymer composition stabilized therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1226578B true DE1226578B (en) | 1966-10-13 |
Family
ID=10122102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES85221A Pending DE1226578B (en) | 1962-05-17 | 1963-05-15 | Process for the production of stabilizers for polyvinyl chloride and its copolymers |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1226578B (en) |
| GB (1) | GB1008845A (en) |
| NL (2) | NL134429C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988750A (en) * | 1981-07-17 | 1991-01-29 | Schering Ag | Non-toxic stabilizer for halogenated polymer |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3067234D1 (en) * | 1979-02-22 | 1984-05-03 | Ciba Geigy Ag | Mixtures consisting of an organo-tin alcoholate and an organo-tin mercaptide; their use as stabilizers for chlorinated polymers |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1020333B (en) * | 1952-05-14 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020332B (en) * | 1953-05-09 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020338B (en) * | 1952-10-16 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020336B (en) * | 1952-05-20 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020334B (en) * | 1952-05-14 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020331B (en) * | 1953-01-02 | 1957-12-05 | Advance Produktion G M B H Deu | Process for the production of new organotin compounds |
| DE1020335B (en) * | 1952-05-23 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020337B (en) * | 1952-09-08 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
-
0
- NL NL292845D patent/NL292845A/xx unknown
- NL NL134429D patent/NL134429C/xx active
-
1962
- 1962-05-17 GB GB19002A patent/GB1008845A/en not_active Expired
-
1963
- 1963-05-15 DE DES85221A patent/DE1226578B/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1020333B (en) * | 1952-05-14 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020334B (en) * | 1952-05-14 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020336B (en) * | 1952-05-20 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020335B (en) * | 1952-05-23 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020337B (en) * | 1952-09-08 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020338B (en) * | 1952-10-16 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020331B (en) * | 1953-01-02 | 1957-12-05 | Advance Produktion G M B H Deu | Process for the production of new organotin compounds |
| DE1020332B (en) * | 1953-05-09 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988750A (en) * | 1981-07-17 | 1991-01-29 | Schering Ag | Non-toxic stabilizer for halogenated polymer |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1008845A (en) | 1965-11-03 |
| NL134429C (en) | |
| NL292845A (en) |
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