EP0000746A1 - Composés d'organoétain, leur préparation et leur application - Google Patents

Composés d'organoétain, leur préparation et leur application Download PDF

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Publication number: EP0000746A1
Authority: EP; European Patent Office
Prior art keywords: alkyl; radical; radicals; aryl; stabilizers
Prior art date: 1977-08-09
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.): Granted

Application number

EP7878100532A

Other languages

German (de)

English (en)

Other versions

EP0000746B1 (fr

Inventor

Helmut Dr. Korbanka

Franz Dr. Scheidl

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.)

1977-08-09

Filing date

1978-07-28

Publication date

1979-02-21

1978-07-28 Application filed by Hoechst AG filed Critical Hoechst AG

1979-02-21 Publication of EP0000746A1 publication Critical patent/EP0000746A1/fr

1981-01-28 Application granted granted Critical

1981-01-28 Publication of EP0000746B1 publication Critical patent/EP0000746B1/fr

Status Expired legal-status Critical Current

Links

-1 Organo tin compounds Chemical class 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title description 4
239000000203 mixture Substances 0.000 claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 21
239000003381 stabilizer Substances 0.000 claims abstract description 18
229920000642 polymer Polymers 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
239000012760 heat stabilizer Substances 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
150000003568 thioethers Chemical class 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
238000010137 moulding (plastic) Methods 0.000 claims 1
150000002148 esters Chemical class 0.000 abstract description 9
150000004820 halides Chemical class 0.000 abstract description 8
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 3
150000001735 carboxylic acids Chemical class 0.000 abstract description 3
239000002253 acid Substances 0.000 abstract description 2
150000007513 acids Chemical class 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 6
230000000087 stabilizing effect Effects 0.000 description 6
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
229920000915 polyvinyl chloride Polymers 0.000 description 5
239000004800 polyvinyl chloride Substances 0.000 description 5
229910052718 tin Inorganic materials 0.000 description 5
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 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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 3
150000003839 salts Chemical class 0.000 description 3
125000004079 stearyl 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])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])[H] 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
235000013539 calcium stearate Nutrition 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
229910052751 metal Chemical class 0.000 description 2
239000002184 metal Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
FBIVKLDWLAMJMB-UHFFFAOYSA-N propyltin Chemical compound CCC[Sn] FBIVKLDWLAMJMB-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 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
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
MQKUWGMWXVSSDB-UHFFFAOYSA-N 4-ethyl-2-sulfanyloctanoic acid Chemical compound CCCCC(CC)CC(S)C(O)=O MQKUWGMWXVSSDB-UHFFFAOYSA-N 0.000 description 1
101000623895 Bos taurus Mucin-15 Proteins 0.000 description 1
WGPUSCCKMVTXRB-UHFFFAOYSA-L C(CC)[Sn](Cl)Cl Chemical compound C(CC)[Sn](Cl)Cl WGPUSCCKMVTXRB-UHFFFAOYSA-L 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
239000004709 Chlorinated polyethylene Substances 0.000 description 1
229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
229920001328 Polyvinylidene chloride Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001336 alkenes 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
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000001769 aryl amino group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-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
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical class [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
229940089960 chloroacetate Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002960 margaryl 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])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])[H] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000005033 polyvinylidene chloride Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical class [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
NFJGHYXSHMSYFA-UHFFFAOYSA-K trichloro(propyl)stannane Chemical compound CCC[Sn](Cl)(Cl)Cl NFJGHYXSHMSYFA-UHFFFAOYSA-K 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Chemical class 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions 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; Compositions of derivatives of such polymers
- C08L27/02—Compositions 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; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions 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; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
- 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
- C07F7/2224—Compounds having one or more tin-oxygen linkages
- 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
- 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

Definitions

the invention relates to new organotin compounds, a process for their preparation and their use as stabilizers for halogen-containing polymers.
heat stabilizers When processing halogen-containing polymers, in particular polymers and copolymers of vinyl chloride and vinylidene chloride, heat stabilizers must be added in order to prevent or largely delay decomposition, which leads to discoloration, embrittlement and deterioration in the mechanical properties.
lead salts of organic and / or inorganic acids barium, cadmium, calcium, strontium, zinc and other metal salts of organic acids or other H-acidic compounds, such as e.g. Phenols and acid esters, as well as organotin compounds are used.
the most effective heat stabilizers include organotin compounds such as organotin mercaptides, thioglycolates and carboxylates.
the alkyl radical may optionally also contain -0-, -S- or -CO 2 groups and OH substituents, and the radicals R 1 to R 5 corresponding in the two mixture components I and II are always the same.
-O 2 C-CH CH-CO 2 -alkyl, where m is the number 1 or 2 and the alkyl radical can optionally also contain -O-, -S- or -CO 2 groups and OH substituents.
R 1 examples are OH, NH 2 , alkyl and arylamino residues such as -NH (CH 3 ), 0-alkyl radicals such as -OCH 3 , -OC 2 H 5 , -OC 8 H 17 , -O-CH 2 -CH 2 -OC 4 H 9 , O-CH 2 -CH 2 -O 2 CC 8 H 17 and O - aryl residues such as
R 2 to R 4 are at least one radical: with R 1 as mentioned above, besides: H, methyl, ethyl, propyl, hexyl, dodecyl, octadecyl, etc.
R 5 examples of R 5 are known residues which are always used in tin stabilizer chemistry.
radicals R 5 are in DT-OSS 1 418 001, 1 418 017, 1 418 019, 1 494 332, 1 544 729, 1 569 070, 1 569 136, 1 569 170, 1 694 936, 1 801 274 and 2 006 711, GB-PS 1 439 752 and US-PS 3 925 309.
Organotin halide mixtures of the formulas are used the meaning of the symbols R 1 to R 4 is given above;
Hal is Cl, Br, J - which, according to the German patent application P 27 357 57, are accessible by reacting certain substituted olefins with metallic tin and hydrogen chloride and sets them at temperatures between about 0 and 150, preferably 15 to 80 ° C.
organotin halides are hydrolyzed to organotin oxides and the latter is reacted with the -SH or -C0 2 H compounds with elimination of water.
Preferred organotin halides are those according to the above formula in which R 0 -alkyl having 1 to 30, preferably 1 to 20 and in particular 1 to 10 carbon atoms, R 3 and R 4 are hydrogen and R 2 with the preferred meanings given for R 1 .
Preferred reaction components representing in the process products of the radical R 5 are esters of thioglycolic acid, esters of T hiopro- propionic acid, alkyl mercaptans having preferably 8 to 18 carbon atoms, such as octyl, dodecyl or stearyl, fatty acids with 8-34 C Atoms, for example lauric acid, 2-ethylhexanoic acid, stearic acid, montanic acid and maleic acid monoesters.
organotin halides used are mixtures of tri and dihalides (ratio of organotin dichloride / organotin trichloride depending on the production process between 1: 0.01 to 1: 4), the organotin compounds according to the invention are also mixtures, which is not disadvantageous for the claimed use, because it is known from the practice of organotin stabilizers that mixtures of diaalkyl and monoalkyltin stabilizers in chlorine-containing polymers such as polyvinyl chloride have a synergistic stabilizing effect.
organotin stabilizers according to the invention show very good stabilizing properties in halogen-containing polymers, for example chlorinated polyethylene, hard and soft polyvinyl chloride, polyvinylidene chloride, polyvinyl chloroacetate and vinyl chloride- ⁇ -olefin copolymers Effect which corresponds to that of known compounds, for example dibutyltin stabilizers.
halogen-containing polymers for example chlorinated polyethylene, hard and soft polyvinyl chloride, polyvinylidene chloride, polyvinyl chloroacetate and vinyl chloride- ⁇ -olefin copolymers Effect which corresponds to that of known compounds, for example dibutyltin stabilizers.
thermoplastic compositions stabilized with the new compounds have improved transparency.
the new stabilizers are generally used together with other known stabilizers, such as calcium stearate or other stabilizing metal salts, stabilizing aids (epoxides, organophosphites), antioxidants such as phenols, UV-stabilizing compounds, lubricants, plasticizers, pigments, fillers and auxiliaries and the like. ⁇ . used. They are used in amounts of 0.1 to 10, preferably 0.2 to 5 and in particular 0.5 to 3 parts by weight, based on 100 parts by weight of polymer.
Examples 1 to 10 describe the preparation of the new organotin compounds
Examples 11 to 32 show the polyvinyl chloride stabilizing effect compared to known organotin compounds.
Example 1 a number of further organotin stabilizers were prepared using the reactants listed in Table 1 below. 0.2 equivalent of the organotin halide, 0.2 mol of the reaction component, 0.2 mol of triethylamine as hydrogen chloride were always used. Acceptor and used a total of 350 ml of toluene as solvent. In all cases, approximately 27.5 g of triethylamine hydrochloride were isolated as a precipitate. As in Example 1, the organotin compounds obtained contained practically no chlorine. Table 2 shows the results in detail, Table 1 lists the starting materials and their amounts.
the mixtures are applied to a 180 ° C heated laboratory two-roll mill and rolled to a skin within one minute at a speed of 20 rpm. Samples are taken from this at intervals of 5 minutes, the colors of which are compared with those of an internal color scale. The individual tests run until the rolled skin takes on a dark brown to black color.
a rolled skin is first produced from the mixtures, as described above, and this is then rolled on the rolling mill at 180 ° C. for 10 minutes. About 0.5 mm thick platelets with a diameter of 30 mm are then punched from the fur drawn by the roller. The platelets are wrapped with an aluminum foil and annealed at 180 ° C in a heated cabinet with air circulation. At intervals of 10 minutes, one plate is removed and the color of the plate compared to the color scale.
the new stabilizers have a comparable PVC-stabilizing effect compared to the known dibutyltin stabilizers (examples 21 to 24 and 32) with the same amounts of tin in the formulation and corresponding residues, but have less influence on the transparency of the test specimens.

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)

EP78100532A 1977-08-09 1978-07-28 Composés d'organoétain, leur préparation et leur application Expired EP0000746B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2735810		1977-08-09
DE2735810A DE2735810B2 (de)	1977-08-09	1977-08-09	Gemische aus Organozinnverbindungen und ihre Verwendung als Stabilisatoren für chlorhaltige Polymere

Publications (2)

Publication Number	Publication Date
EP0000746A1 true EP0000746A1 (fr)	1979-02-21
EP0000746B1 EP0000746B1 (fr)	1981-01-28

Family

ID=6015962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP78100532A Expired EP0000746B1 (fr)	1977-08-09	1978-07-28	Composés d'organoétain, leur préparation et leur application

Country Status (6)

Country	Link
US (1)	US4237043A (fr)
EP (1)	EP0000746B1 (fr)
JP (1)	JPS5430119A (fr)
CA (1)	CA1116625A (fr)
DE (2)	DE2735810B2 (fr)
IT (1)	IT1098005B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2457298A1 (fr) *	1979-05-23	1980-12-19	Elf Aquitaine	Compositions de stabilisants organostanniques pour resines halogeno-vinyliques
US4988750A (en) *	1981-07-17	1991-01-29	Schering Ag	Non-toxic stabilizer for halogenated polymer
FR2758141A1 (fr) *	1997-01-09	1998-07-10	Atochem North America Elf	Composition a base de maleates d'organoetain de poids moleculaire eleve utilisable pour stabiliser des polymeres thermoplastiques. procede d'obtention de ladite composition
FR2758142A1 (fr) *	1997-01-09	1998-07-10	Atochem North America Elf	Composition a base de maleates d'organoetain utilisable pour stabiliser et lubrifier des polymeres thermoplastiques. procede d'obtention de ladite composition

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4360619A (en) *	1981-02-26	1982-11-23	Carstab Corporation	Stabilizer compositions and polymers containing same
US4314934A (en) *	1981-02-26	1982-02-09	Carstab Corporation	Organohalide polymers stabilized with an organotin compound and an ortho mercapto phenol compound
PL147517B1 (en) *	1985-09-25	1989-06-30	Politechnika Warszawska	Method of obtaining cyanoorganic compounds
GB8724049D0 (en) *	1987-10-14	1987-11-18	Kodak Ltd	Organotin compounds as anionic ionophores
US5470995A (en) *	1993-06-29	1995-11-28	Morton International, Inc.	Continuous process for making a dialkyltin thiocarboxylic acid ester
EP2123659A1 (fr) *	2008-05-15	2009-11-25	Arkema France	Composés de monoalkyltine à pureté élevée et utilisations associées

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2285392A1 (fr) *	1974-09-16	1976-04-16	Akzo Nv	Composes organostanniques, stabilisants pour polymeres les renfermant, leur procede de preparation et intermediaires necessaires a leur preparation
FR2306208A1 (fr) *	1975-03-17	1976-10-29	Akzo Nv	Procede pour preparer des dihalogenures organostanniques utiles comme intermediaires dans la preparation des stabilisants pour polymeres

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3440255A (en) *	1967-09-28	1969-04-22	Sumio Matsuda	Process for preparing organotin halides
US4105684A (en) *	1974-09-16	1978-08-08	Akzo N.V.	Process for the preparation of organotin trihalides
US4080363A (en) *	1975-03-17	1978-03-21	Akzo N.V.	Process for making organotin dihalides and trihalides and stabilizers prepared therefrom

1977
- 1977-08-09 DE DE2735810A patent/DE2735810B2/de not_active Withdrawn
1978
- 1978-07-28 EP EP78100532A patent/EP0000746B1/fr not_active Expired
- 1978-07-28 DE DE7878100532T patent/DE2860371D1/de not_active Expired
- 1978-08-07 IT IT26560/78A patent/IT1098005B/it active
- 1978-08-08 CA CA000308882A patent/CA1116625A/fr not_active Expired
- 1978-08-08 JP JP9587878A patent/JPS5430119A/ja active Pending
- 1978-08-08 US US05/931,897 patent/US4237043A/en not_active Expired - Lifetime

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2285392A1 (fr) *	1974-09-16	1976-04-16	Akzo Nv	Composes organostanniques, stabilisants pour polymeres les renfermant, leur procede de preparation et intermediaires necessaires a leur preparation
FR2306208A1 (fr) *	1975-03-17	1976-10-29	Akzo Nv	Procede pour preparer des dihalogenures organostanniques utiles comme intermediaires dans la preparation des stabilisants pour polymeres

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2457298A1 (fr) *	1979-05-23	1980-12-19	Elf Aquitaine	Compositions de stabilisants organostanniques pour resines halogeno-vinyliques
EP0021033A1 (fr) *	1979-05-23	1981-01-07	Societe Nationale Elf Aquitaine	Compositions stabilisatrices contenant des composés monoorgano tris-thioalkyl étain et leur application à la stabilisation de polymères halogéno-vinyliques
US4988750A (en) *	1981-07-17	1991-01-29	Schering Ag	Non-toxic stabilizer for halogenated polymer
FR2758141A1 (fr) *	1997-01-09	1998-07-10	Atochem North America Elf	Composition a base de maleates d'organoetain de poids moleculaire eleve utilisable pour stabiliser des polymeres thermoplastiques. procede d'obtention de ladite composition
FR2758142A1 (fr) *	1997-01-09	1998-07-10	Atochem North America Elf	Composition a base de maleates d'organoetain utilisable pour stabiliser et lubrifier des polymeres thermoplastiques. procede d'obtention de ladite composition
WO1998030531A1 (fr) *	1997-01-09	1998-07-16	Elf Atochem S.A.	Composition a base de maleates d'organoetain utilisable pour stabiliser et lubrifier des polymeres thermoplastiques. procede d'obtention de ladite composition

Also Published As

Publication number	Publication date
DE2735810B2 (de)	1981-01-29
DE2860371D1 (en)	1981-03-19
IT1098005B (it)	1985-08-31
DE2735810A1 (de)	1979-02-15
US4237043A (en)	1980-12-02
JPS5430119A (en)	1979-03-06
CA1116625A (fr)	1982-01-19
IT7826560A0 (it)	1978-08-07
EP0000746B1 (fr)	1981-01-28

Legal Events

Date	Code	Title	Description
1979-01-02	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
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