TWI285657B - Phosphite reactions in the presence of metal soaps for liquid stabilisers - Google Patents
Phosphite reactions in the presence of metal soaps for liquid stabilisers Download PDFInfo
- Publication number
- TWI285657B TWI285657B TW092114915A TW92114915A TWI285657B TW I285657 B TWI285657 B TW I285657B TW 092114915 A TW092114915 A TW 092114915A TW 92114915 A TW92114915 A TW 92114915A TW I285657 B TWI285657 B TW I285657B
- Authority
- TW
- Taiwan
- Prior art keywords
- phosphite
- group
- organic
- acid
- metal
- Prior art date
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- 239000003381 stabilizer Substances 0.000 title claims abstract description 54
- 239000007788 liquid Substances 0.000 title claims abstract description 34
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 25
- 239000002184 metal Substances 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 title description 3
- 239000000344 soap Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 239000002904 solvent Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 22
- -1 organophosphite esters Chemical class 0.000 claims abstract description 22
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- 239000004800 polyvinyl chloride Substances 0.000 claims abstract description 8
- 229920000915 polyvinyl chloride Polymers 0.000 claims abstract description 8
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 5
- 229910052788 barium Inorganic materials 0.000 claims abstract description 4
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 4
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 4
- 239000000654 additive Substances 0.000 claims abstract description 3
- 229910052793 cadmium Inorganic materials 0.000 claims abstract 2
- 229920000642 polymer Polymers 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 7
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004440 Isodecyl alcohol Substances 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
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- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
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- 150000002009 diols Chemical class 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 2
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 claims description 2
- NSENZNPLAVRFMJ-UHFFFAOYSA-N 2,3-dibutylphenol Chemical compound CCCCC1=CC=CC(O)=C1CCCC NSENZNPLAVRFMJ-UHFFFAOYSA-N 0.000 claims description 2
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 claims description 2
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920000388 Polyphosphate Polymers 0.000 claims description 2
- 239000001177 diphosphate Substances 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000001205 polyphosphate Substances 0.000 claims description 2
- 235000011176 polyphosphates Nutrition 0.000 claims description 2
- 229940087291 tridecyl alcohol Drugs 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- SWUYLUYFFADSNR-UHFFFAOYSA-N decyl phenyl hydrogen phosphite Chemical compound CCCCCCCCCCOP(O)OC1=CC=CC=C1 SWUYLUYFFADSNR-UHFFFAOYSA-N 0.000 claims 2
- XZZWOTQMUOIIFX-UHFFFAOYSA-N 1-(2-diphenoxyphosphanyloxypropoxy)propan-2-yl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC(C)COCC(C)OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 XZZWOTQMUOIIFX-UHFFFAOYSA-N 0.000 claims 1
- IJBWMYBRNPIXJT-UHFFFAOYSA-N 2,3-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC(O)=C(C(C)(C)C=2C=CC=CC=2)C=1C(C)(C)C1=CC=CC=C1 IJBWMYBRNPIXJT-UHFFFAOYSA-N 0.000 claims 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003708 ampul Substances 0.000 claims 1
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- 159000000032 aromatic acids Chemical class 0.000 claims 1
- 230000002950 deficient Effects 0.000 claims 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 239000002594 sorbent Substances 0.000 claims 1
- 229920006029 tetra-polymer Polymers 0.000 claims 1
- 150000008301 phosphite esters Chemical class 0.000 abstract description 10
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- 238000002360 preparation method Methods 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 5
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- 238000000926 separation method Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl 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
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08L57/06—Homopolymers or copolymers containing elements other than carbon and hydrogen
- C08L57/08—Homopolymers or copolymers containing elements other than carbon and hydrogen containing halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03076007 | 2003-04-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200420645A TW200420645A (en) | 2004-10-16 |
| TWI285657B true TWI285657B (en) | 2007-08-21 |
Family
ID=33104136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092114915A TWI285657B (en) | 2003-04-04 | 2003-06-02 | Phosphite reactions in the presence of metal soaps for liquid stabilisers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20060106155A1 (enExample) |
| EP (1) | EP1611142A1 (enExample) |
| JP (1) | JP2006522185A (enExample) |
| KR (1) | KR20060002899A (enExample) |
| CN (1) | CN1768068A (enExample) |
| TW (1) | TWI285657B (enExample) |
| WO (1) | WO2004087722A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20042464A1 (it) * | 2004-12-23 | 2005-03-23 | Baerlocher Italia S P A | Composizione stabilizzante contenente esteri fosfito |
| US8412338B2 (en) * | 2008-11-18 | 2013-04-02 | Setpoint Medical Corporation | Devices and methods for optimizing electrode placement for anti-inflamatory stimulation |
| CN103412486A (zh) * | 2013-07-23 | 2013-11-27 | 沈阳化工大学 | 一种聚氯乙烯汽提过程智能控制方法 |
| EP2886594A1 (en) * | 2013-12-18 | 2015-06-24 | Baerlocher GmbH | Liquid zinc salt preparation as stabilizer for halogenated polymers |
| CN103980537B (zh) * | 2014-06-03 | 2016-10-19 | 江苏联盟化学有限公司 | 复配有酸式亚磷酸酯的新型液体稳定剂及制备工艺 |
| CN106751064B (zh) * | 2016-12-10 | 2019-04-05 | 包头稀土研究院 | 一种磷或膦酸脂类稀土化合物pvc热稳定剂 |
| CN109054082B (zh) * | 2018-07-23 | 2020-04-28 | 浙江锦润生物科技有限公司 | 一种含有亚磷酸有机酯稳定剂及其合成方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2307075A (en) * | 1940-08-02 | 1943-01-05 | Carbide And Carbon Chemicais C | Vinyl resin composition |
| US2564646A (en) * | 1950-02-08 | 1951-08-14 | Argus Chemical Lab Inc | Haze resistant vinyl chloride polymers |
| US2867594A (en) * | 1957-03-21 | 1959-01-06 | Vinyl chloride resin stabilized with | |
| US2997454A (en) * | 1959-05-18 | 1961-08-22 | Argus Chem | Polyvinyl chloride stabilizer combinations of phosphorus acid with triphosphites andheavy metal salts |
| US3519584A (en) * | 1966-12-05 | 1970-07-07 | Synthetic Products Co | Vinyl halide polymers stabilized with mixtures comprising a metal phenatephosphite and a metal carboxylate-phosphite |
| US4102839A (en) * | 1975-01-10 | 1978-07-25 | Rhone-Poulenc Industries | Stabilization of vinyl chloride polymers |
| JPS5448848A (en) * | 1977-09-26 | 1979-04-17 | Adeka Argus Chem Co Ltd | Halogen-containing resin compostion |
| US4446061A (en) * | 1979-10-25 | 1984-05-01 | Monsanto Company | Composition containing reaction products of metal oxides and salts with phosphorus compounds |
| EP0047894B2 (en) * | 1980-09-05 | 1990-09-05 | Argus Chemical Corporation | Homogeneous storage-stable liquid barium-cadmium-triphosphite stabilizer systems for polyvinyl chloride resins |
| US4401779A (en) * | 1981-12-31 | 1983-08-30 | Argus Chemical Corporation | Homogeneous liquid barium carbonate-barium alkyl phenate-cadmium carboxylate stabilizer systems for rigid polyvinyl chloride resins |
| US4482506A (en) * | 1982-10-04 | 1984-11-13 | Fmc Corporation | Process for the manufacture of alkyl diaryl phosphate esters |
| JPS59100153A (ja) * | 1982-11-30 | 1984-06-09 | Dainippon Ink & Chem Inc | ポリ塩化ビニル樹脂組成物 |
| JPS60219246A (ja) * | 1984-04-16 | 1985-11-01 | Nissan Fuero Yuki Kagaku Kk | 含ハロゲン樹脂組成物 |
| US4614756A (en) * | 1985-08-01 | 1986-09-30 | Borg-Warner Chemicals, Inc. | Stabilization composition for clear, impact-modified PVC |
| FR2633293B1 (fr) * | 1988-06-24 | 1991-03-22 | Rhone Poulenc Chimie | Nouveaux polyphosphites et leur utilisation comme stabilisants des polymeres halogenes |
| EP0792317B1 (en) * | 1994-11-14 | 2004-02-18 | Crompton Corporation | Liquid pvc stabilizers and lubricants |
-
2003
- 2003-06-02 TW TW092114915A patent/TWI285657B/zh not_active IP Right Cessation
-
2004
- 2004-03-23 WO PCT/EP2004/003067 patent/WO2004087722A1/en not_active Ceased
- 2004-03-23 JP JP2006504821A patent/JP2006522185A/ja active Pending
- 2004-03-23 US US10/546,249 patent/US20060106155A1/en not_active Abandoned
- 2004-03-23 KR KR1020057018549A patent/KR20060002899A/ko not_active Withdrawn
- 2004-03-23 CN CNA2004800088106A patent/CN1768068A/zh active Pending
- 2004-03-23 EP EP04722561A patent/EP1611142A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060002899A (ko) | 2006-01-09 |
| TW200420645A (en) | 2004-10-16 |
| JP2006522185A (ja) | 2006-09-28 |
| WO2004087722A1 (en) | 2004-10-14 |
| CN1768068A (zh) | 2006-05-03 |
| US20060106155A1 (en) | 2006-05-18 |
| EP1611142A1 (en) | 2006-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |