GB1011839A - Phosphorus stabilizers - Google Patents
Phosphorus stabilizersInfo
- Publication number
- GB1011839A GB1011839A GB1838363A GB1838363A GB1011839A GB 1011839 A GB1011839 A GB 1011839A GB 1838363 A GB1838363 A GB 1838363A GB 1838363 A GB1838363 A GB 1838363A GB 1011839 A GB1011839 A GB 1011839A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorothiolothionate
- bis
- acid
- neopentylene
- hexylene
- 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.)
- Expired
Links
- 239000003381 stabilizer Substances 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 abstract 6
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- -1 alkaline earth metal salts Chemical class 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract 2
- 125000002524 organometallic group Chemical group 0.000 abstract 2
- IUONZAZXFRWPFL-UHFFFAOYSA-N (dihexoxyphosphinothioyldisulfanyl)-dihexoxy-sulfanylidene-lambda5-phosphane Chemical compound C(CCCCC)OP(=S)(OCCCCCC)SSP(=S)(OCCCCCC)OCCCCCC IUONZAZXFRWPFL-UHFFFAOYSA-N 0.000 abstract 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 abstract 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 abstract 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 abstract 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003490 Thiodipropionic acid Substances 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- YXJLCFOMIVREPX-UHFFFAOYSA-M acetic acid diethoxy-sulfanylidene-tributylstannylsulfanyl-lambda5-phosphane Chemical compound C(C)(=O)O.C(C)OP(=S)(S[Sn](CCCC)(CCCC)CCCC)OCC YXJLCFOMIVREPX-UHFFFAOYSA-M 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- CVAGYCLEIYGJQT-UHFFFAOYSA-N dichloro(dioctyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)CCCCCCCC CVAGYCLEIYGJQT-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- LNKLQXXAPWJCPZ-UHFFFAOYSA-N dioctylsilicon Chemical compound CCCCCCCC[Si]CCCCCCCC LNKLQXXAPWJCPZ-UHFFFAOYSA-N 0.000 abstract 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000002530 phenolic antioxidant Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 235000019303 thiodipropionic acid Nutrition 0.000 abstract 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1658—Esters of thiopolyphosphoric acids or anhydrides
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/5398—Phosphorus bound to sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
A polymer of a C2 to C4 olefin is stabilized with a phosphorothiolothionic acid or a salt, ester or a disulphide derivative thereof. Other stabilizers which may be present are esters of thiodipropionic acid, alkaline earth metal salts of fatty acids, and phenolic antioxidants. Example 22 describes the preparation of dioctylsilicon bis-(o,o-1,3-neopentylene phosphorothiolothionate <FORM:1011839/C3/1> by heating sodium neopentylene phosphorothiolothionate and dioctyl silicon dichloride in acetonitrile.ALSO:Various dithiophosphoric esters are obtained by reacting 2 moles of alcohol or 1 mole of glycol with 0.5 mole of P2S5 in benzene and then isolating the products by removing the benzene under reduced pressure. Metal derivatives or organometallic derivates of the dithiophosphoric esters may be obtained by reaction of the ester/benzene solution with metal oxide or organo-metallic oxide. The products obtained are:-(1) o,o-di-n-hexyl phosphorothiolothionic acid, (2) o,o-1,3-butylene phosphorothiolothionic acid, <FORM:1011839/C2/1> (3) o,o - 2 - ethyl - 1,3 - hexylene phosphorothiolothionic acid, <FORM:1011839/C2/2> (4) o,o - di - p - cresyl phosphorothiolothionic acid, (5) o,o - di - (2,2,4 - trimethylpentyl) phosphorothiolothionic acid, (6) o,o-1,3-neopentylene phosphorothiolothionic acid, <FORM:1011839/C2/3> (7) barium bis - (o.o - di - n - butyl phosphorothiolothionate), <FORM:1011839/C2/4> (8) zinc bis-(o,o-diisooctyl phosphorothiolo thionate), (9) dibutyltin bis - (o,o - dibutyl phosphorothiolothionate), <FORM:1011839/C2/5> (10) dibutyltin bis - (o,o - di - n - hexyl phosphorothiolothionate), (11) dibutyltin bis - (o,o-di - (2,2,4 - triMepentyl) phosphorothiolothionate), (12) dibutyltin - bis - (o o - 2 - ethyl-1,3 - hexylene phosphorothiolothionate), (13) dibutyltin bis - (o,o - 1,3 - neo - pentylene phosphorothiolothionate), <FORM:1011839/C2/6> (14) dibutyltin bis - (o,o - di - p - cresyl phosphorothiolothionate), (15) dioctyltin bis - (o,o-di - n - hexyl phosphorothiolothionate), (16) dioctyl tin bis - (o,o - 1,3 - butylene phosphorothiolothionate), (17) dioctyltin bis - (o,o - 2-ethyl - 1,3 - hexylene phosphorothiolothionate), (18) dioctyl tin bis - (o,o - di - (2,2,4 - triMepentyl) phosphorothiolothionate), (19) dioctyl tin bis - (o,o - 1,3 - neopentylene phosphorothiolothionate), (20) tributyl tin (o,o - diethyl phosphorothiolothionate, (21) (diethoxyphosphinothioyl) thio-(tributyltin) acetate. <FORM:1011839/C2/7> In Examples (23) o,o-1,3-neopentylene-S-(1,2 - dicarboethoxyethyl) - phosphorothiolothionate <FORM:1011839/C2/8> is obtained from o,o-1,3-neopentylene phosphorothiolothioni acid and diethyl maleate. (24) o,o - 2 - ethyl - 1,3 - hexylene S - lauryl phosphorothiolothionate is prepared from o,o-2 - ethyl - 1,3 - hexylene phosphorothiolothionic acid by treatment with sodium methoxide followed by dodecyl iodide; (25), (26) and (27) bis - [di - (2,2,4 - triMepentoxy) phosphinothioyl)] disulphide, <FORM:1011839/C2/9> bis - (di - n - hexoxy phosphinothioyl) disulphide, and bis-(1,3-oxybutylene phosphinothioyl) disulphide are prepared by hydrogen peroxide oxidation of the corresponding thiolothionic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19472262A | 1962-05-14 | 1962-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1011839A true GB1011839A (en) | 1965-12-01 |
Family
ID=22718677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1838363A Expired GB1011839A (en) | 1962-05-14 | 1963-05-09 | Phosphorus stabilizers |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT251868B (en) |
| CH (1) | CH440691A (en) |
| GB (1) | GB1011839A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107312031A (en) * | 2017-06-22 | 2017-11-03 | 新乡市瑞丰新材料股份有限公司 | A kind of preparation method of di-isooctyl dithio zinc phosphate salt |
| CN107556339A (en) * | 2016-07-01 | 2018-01-09 | 新乡市瑞丰新材料股份有限公司 | A kind of preparation method of di-isooctyl dithio zinc phosphate |
-
1963
- 1963-05-09 GB GB1838363A patent/GB1011839A/en not_active Expired
- 1963-05-14 AT AT391463A patent/AT251868B/en active
- 1963-05-14 CH CH602663A patent/CH440691A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107556339A (en) * | 2016-07-01 | 2018-01-09 | 新乡市瑞丰新材料股份有限公司 | A kind of preparation method of di-isooctyl dithio zinc phosphate |
| CN107312031A (en) * | 2017-06-22 | 2017-11-03 | 新乡市瑞丰新材料股份有限公司 | A kind of preparation method of di-isooctyl dithio zinc phosphate salt |
Also Published As
| Publication number | Publication date |
|---|---|
| CH440691A (en) | 1967-07-31 |
| AT251868B (en) | 1967-01-25 |
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