DE1020332B - Process for the production of new organotin compounds - Google Patents
Process for the production of new organotin compoundsInfo
- Publication number
- DE1020332B DE1020332B DEA17989A DEA0017989A DE1020332B DE 1020332 B DE1020332 B DE 1020332B DE A17989 A DEA17989 A DE A17989A DE A0017989 A DEA0017989 A DE A0017989A DE 1020332 B DE1020332 B DE 1020332B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- ester
- organotin
- mol
- tin
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 12
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 229910052718 tin Inorganic materials 0.000 description 8
- -1 heterocyclic radical Chemical class 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- DZXKSFDSPBRJPS-UHFFFAOYSA-N tin(2+);sulfide Chemical compound [S-2].[Sn+2] DZXKSFDSPBRJPS-UHFFFAOYSA-N 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- KBAYQFWFCOOCIC-GJTWTXHOSA-N [(1r,4ar,4bs,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methanol Chemical compound OC[C@]1(C)CCC[C@]2(C)[C@H]3CCC(C(C)C)CC3CC[C@H]21 KBAYQFWFCOOCIC-GJTWTXHOSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 230000002411 adverse Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FAMUPMBATZGWOV-UHFFFAOYSA-M bromo(triphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Br)C1=CC=CC=C1 FAMUPMBATZGWOV-UHFFFAOYSA-M 0.000 description 1
- DGAODIKUWGRDBO-UHFFFAOYSA-N butanethioic s-acid Chemical compound CCCC(O)=S DGAODIKUWGRDBO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- YREAYUWMESCMHJ-UHFFFAOYSA-L didodecyltin(2+);dichloride Chemical compound CCCCCCCCCCCC[Sn](Cl)(Cl)CCCCCCCCCCCC YREAYUWMESCMHJ-UHFFFAOYSA-L 0.000 description 1
- 238000002845 discoloration Methods 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
- 229920001971 elastomer Polymers 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- YEUAOTZWAWUYBH-UHFFFAOYSA-N hexanethioic s-acid Chemical compound CCCCCC(S)=O YEUAOTZWAWUYBH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OTIJNTWWDCIUNM-UHFFFAOYSA-N pentanethioic s-acid Chemical compound CCCCC(S)=O OTIJNTWWDCIUNM-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0078—Metal hydrides or organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon link
-
- 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
- C07F7/226—Compounds with one or more Sn-S linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
Description
Verfahren zur Herstellung von neuen Organozinnverbindungen Die Erfindung betrifft die Herstellung neuer organischer Derivate des vierwertigen Zinns und Mischungen, welche dieselben enthalten.Process for the preparation of novel organotin compounds The invention concerns the production of new organic derivatives of tetravalent tin and mixtures, which contain the same.
Die erfindungsgemäßen Produkte sind besonders wertvoll als Stabilisatoren für halogenhaltige Harze und andere halogenhaltige organische Verbindungen. Halogenhaltige Harze, die so stabilisiert werden, sind z. B. Polyvinylchlorid, andere Polyvinylhalogenide und Mischpolymerisate von Vinylchlorid mit Vinylacetat, Vinylidenchlorid, Styrol und ähnlichen Verbindungen. Andere hierher gehörige organische Verbindungen sind z. B. chlorierte Paraffine mit 10 bis 40 C-Atomen.The products according to the invention are particularly useful as stabilizers for halogen-containing resins and other halogen-containing organic compounds. Halogen containing Resins which are stabilized in this way are e.g. B. polyvinyl chloride, other polyvinyl halides and copolymers of vinyl chloride with vinyl acetate, vinylidene chloride, styrene and similar connections. Other organic compounds belonging to this subheading are z. B. chlorinated paraffins with 10 to 40 carbon atoms.
Die gebräuchlichen organischen Zinnstabilisatoren sind Verbindungen wie z. B. Dibutylzinnmaleat und -laurat. Jedoch sind diese Stabilisatoren nicht genügend wirksam. Sie haben ferner den Nachteil, für sich selbst bei den hohen Temperaturen der Verarbeitung von Vinylharzen nicht ganz stabil zu sein, wodurch Verfärbungen der plastischen Massen bewirkt werden. Überdies verursachen sie häufig Ausblühungen auf der Oberfläche. Dibutylzinnmaleat macht auch noch Schwierigkeiten in der Verarbeitung durch Kleben auf den Kalanderflächen.The common organic tin stabilizers are compounds such as B. dibutyl tin maleate and laurate. However, these stabilizers are not sufficiently effective. They also have the disadvantage of themselves at the high temperatures The processing of vinyl resins is not entirely stable, causing discoloration the plastic masses are effected. In addition, they often cause efflorescence on the surface. Dibutyltin maleate also causes difficulties in processing by gluing on the calender surfaces.
Es wurde gefunden, daß eine bestimmte Art von Zinnderivaten weitaus bessere Resultate als Stabilisatoren gibt, und zwar solche Derivate des vierwertigen Zinns, in welchen das Zinn mit einem Teil seiner Valenzen direkt mit Schwefel verbunden ist.It has been found that a certain type of tin derivative far gives better results than stabilizers, namely such derivatives of the tetravalent Tin, in which the tin, with part of its valences, is directly connected to sulfur is.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Organozinnverbindungen der allgemeinen Formel R. Sn X4 _ n,, worin R Alkyl, Aryl, ein hydroaromatischer oder heterocyclischer Rest und X ein Esterrest einer einbasischen Mercaptosäure ist, deren Schwefelatom an Zinn gebunden ist, und wobei n eine ganze Zahl von 1 bis 3 bedeutet, dadurch gekennzeichnet, daß man einen Ester aus einer einbasischen Mercaptosäure mit 2 bis 6 Kohlenstoffatomen und einem einwertigen Alkohol mit einem Organozinnhalogenid, Organozinnoxyd oder einer Organostannonsäure in den entsprechenden Mengenverhältnissen umsetzt.The invention relates to a process for the production of organotin compounds of the general formula R. Sn X4 _ n ,, where R is alkyl, aryl, a hydroaromatic or heterocyclic radical and X is an ester radical of a monobasic mercapto acid whose sulfur atom is bonded to tin, and where n is an integer of 1 to 3 means, characterized in that one is an ester from a monobasic Mercapto acid with 2 to 6 carbon atoms and a monohydric alcohol with a Organotin halide, organotin oxide or an organostannonic acid in the corresponding Implements quantitative proportions.
Die Verbindungen gemäß der Erfindung leiten sich somit vom vierwertigen Zinn ab. Mindestens mit einer und höchstens mit drei Valenzen bindet das Zinn direkt den Schwefel des Esters einer Mercaptosäure, während die restlichen Valenzen durch Alkyl, Aryl, hydroaromatische oder heterocyclische Radikale abgesättigt sind.The compounds according to the invention are thus derived from the tetravalent Tin off. The tin binds directly with at least one and at most three valences the sulfur of the ester of a mercapto acid, while the remaining valences through Alkyl, aryl, hydroaromatic or heterocyclic radicals are saturated.
Beispiele für R sind CH", C,H5, C4H9, C8H", C12H25; Aryl, wie C, H" C H3 C, H4, (C H3)2 C, H3; Furfuryl und Tetrahydrofurfuryl.Examples of R are CH ", C, H5, C4H9, C8H", C12H25; Aryl such as C, H " C H3 C, H4, (C H3) 2 C, H3; furfuryl and tetrahydrofurfuryl.
Beispiele für X sind Ester von Thioglycolsäure mit Butyl-, Hexyl-, Octyl-, Dodecyl-, Benzyl-, Cyclohexyl-, Tetrahydrofurfuryl- und Tetrahydroabietylalkohol. Anstatt Thioglycolsäure können Ester von Thiopropionsäure, Thiobuttersäure, Thiovaleriansäure und Thiocapronsäure verwendet werden. Nimmt man als Beispiel die Butylzinnthioglycolsäurebutylester, so sind folgende drei Verbindungen herstellbar C,H,Sn(SCH,COOC,H9)s (C4 H9)2Sn(SCH,COOC,H9)2 (C,H9)sSn(SCH,COOC,H9) Die neuen Zinnverbindungen sind ölige Flüssigkeiten von hoher Viskosität, die in vielen organischen Lösungsmitteln, wie Äther, Benzol, Toluol, Chloroform, löslich sind.Examples of X are esters of thioglycolic acid with butyl, hexyl, Octyl, dodecyl, benzyl, cyclohexyl, tetrahydrofurfuryl and tetrahydroabietyl alcohol. Instead of thioglycolic acid you can use esters of thiopropionic acid, thiobutyric acid, thiovaleric acid and thiocaproic acid can be used. If one takes the butyltin thioglycolic acid butyl ester as an example, the following three compounds can be produced C, H, Sn (SCH, COOC, H9) s (C4 H9) 2Sn (SCH, COOC, H9) 2 (C, H9) sSn (SCH, COOC, H9) The new tin compounds are oily liquids of high Viscosity, which in many organic solvents, such as ether, benzene, toluene, Chloroform, are soluble.
Beispiel 1 (C,H9)ZSn(SCH,COOC,H11)a 92 g Thioglycolsäure (1 Mol), 100 g Cyclohexanol (1 Mol) und 150 cm3 Benzol, enthaltend 0,3 g p-Toluolsulfonsäure, werden unter Rückfluß gekocht, bis 18 cm3 Wasser azeotropisch abdestilliert sind. Sodann werden 124 g (1/2 Mol) Dibutylzinnoxyd zugefügt und das Sieden fortgesetzt, bis weitere 9 cm' Wasser abdestilliert werden. Das Dibutylzinnoxyd geht hierbei in Lösung. Nach Filtrieren von kleinen Verunreinigungen und Abdestillieren des Benzols verbleibt ein öliger, sehr viskoser Rückstand von leicht gelblicher Farbe, der in den üblichen organischen Lösungsmitteln löslich ist.Example 1 (C, H9) ZSn (SCH, COOC, H11) a 92 g thioglycolic acid (1 mol), 100 g cyclohexanol (1 mol) and 150 cm3 benzene, containing 0.3 g p-toluenesulfonic acid, are refluxed until 18 cm3 of water are azeotropically distilled off. Then 124 g (1/2 mol) of dibutyltin oxide are added and the boiling is continued, until another 9 cm 'of water is distilled off. The dibutyltin oxide goes here in solution. After filtering off small impurities and distilling off the benzene remains an oily, very viscous residue of a slightly yellowish color, which in is soluble in common organic solvents.
Analvse
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA17989A DE1020332B (en) | 1953-05-09 | 1953-05-09 | Process for the production of new organotin compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA17989A DE1020332B (en) | 1953-05-09 | 1953-05-09 | Process for the production of new organotin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1020332B true DE1020332B (en) | 1957-12-05 |
Family
ID=6924036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA17989A Pending DE1020332B (en) | 1953-05-09 | 1953-05-09 | Process for the production of new organotin compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1020332B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1226578B (en) * | 1962-05-17 | 1966-10-13 | Harold Verity Smith | Process for the production of stabilizers for polyvinyl chloride and its copolymers |
| DE1276643B (en) * | 1966-03-04 | 1968-09-05 | Greiz Doelau Chemie | Process for the preparation of mercapto compounds containing tin or antimony |
-
1953
- 1953-05-09 DE DEA17989A patent/DE1020332B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1226578B (en) * | 1962-05-17 | 1966-10-13 | Harold Verity Smith | Process for the production of stabilizers for polyvinyl chloride and its copolymers |
| DE1276643B (en) * | 1966-03-04 | 1968-09-05 | Greiz Doelau Chemie | Process for the preparation of mercapto compounds containing tin or antimony |
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