CA1136152A - Methode de preparation de polyphosphites aromatiques - Google Patents

Methode de preparation de polyphosphites aromatiques

Info

Publication number: CA1136152A
Authority: CA; Canada
Prior art keywords: bis; polyphosphites; alkylidene; phenolic; group
Prior art date: 1979-02-05
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

Application number

CA000343754A

Other languages

English (en)

Inventor

Ingenuin Hechenbleikner

Leo L. Valdiserri

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.)

GE Chemicals Inc

Original Assignee

Borg Warner Chemicals Inc

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.)

1979-02-05

Filing date

1980-01-16

Publication date

1982-11-23

1980-01-16 Application filed by Borg Warner Chemicals Inc filed Critical Borg Warner Chemicals Inc

1982-11-23 Application granted granted Critical

1982-11-23 Publication of CA1136152A publication Critical patent/CA1136152A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 6
125000003118 aryl group Chemical group 0.000 title abstract description 9
-1 pentaerythritol diphosphite compound Chemical class 0.000 claims abstract description 27
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 14
125000001118 alkylidene group Chemical group 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
239000002530 phenolic antioxidant Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 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
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
229920000642 polymer Polymers 0.000 abstract description 11
239000000654 additive Substances 0.000 abstract description 4
230000000996 additive effect Effects 0.000 abstract description 2
239000000047 product Substances 0.000 description 15
239000004743 Polypropylene Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229920001155 polypropylene Polymers 0.000 description 9
238000001125 extrusion Methods 0.000 description 8
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 description 8
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 description 7
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 5
235000006708 antioxidants Nutrition 0.000 description 5
239000000155 melt Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
YGPLZBDXFXBLMZ-UHFFFAOYSA-N 1,1-dichloro-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)C(O)(Cl)Cl YGPLZBDXFXBLMZ-UHFFFAOYSA-N 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
229940059574 pentaerithrityl Drugs 0.000 description 4
229920000098 polyolefin Polymers 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 3
PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
238000011109 contamination Methods 0.000 description 3
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
230000000087 stabilizing effect Effects 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
230000004580 weight loss Effects 0.000 description 3
UYUWMEGBJMKHFG-UHFFFAOYSA-N 1,1-dichloro-2,2-bis(hydroxymethyl)propane-1,3-diol phosphorous acid Chemical compound P(O)(O)O.P(O)(O)O.ClC(O)(C(CO)(CO)CO)Cl UYUWMEGBJMKHFG-UHFFFAOYSA-N 0.000 description 2
HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
235000013539 calcium stearate Nutrition 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug 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
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229940086542 triethylamine Drugs 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
WAOPGHCXGUXHKF-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-1,1-diphenylpropane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C1(=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=CC=CC=C1 WAOPGHCXGUXHKF-UHFFFAOYSA-N 0.000 description 1
PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
239000002656 Distearyl thiodipropionate Substances 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
JBTXGEJRJCNRLU-UHFFFAOYSA-N [2-(dihydroxyphosphanyloxymethyl)-3-hydroxy-2-(hydroxymethyl)propyl] dihydrogen phosphite Chemical class OP(O)OCC(CO)(CO)COP(O)O JBTXGEJRJCNRLU-UHFFFAOYSA-N 0.000 description 1
BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
238000005553 drilling Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010097 foam moulding Methods 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010030 laminating Methods 0.000 description 1
230000007775 late Effects 0.000 description 1
238000003754 machining Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000008259 solid foam Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000013112 stability test Methods 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000003856 thermoforming Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000003466 welding Methods 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
- 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
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

CA000343754A 1979-02-05 1980-01-16 Methode de preparation de polyphosphites aromatiques Expired CA1136152A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US903479A	1979-02-05	1979-02-05
US9,034		1979-02-05

Publications (1)

Publication Number	Publication Date
CA1136152A true CA1136152A (fr)	1982-11-23

Family

ID=21735205

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000343754A Expired CA1136152A (fr)	1979-02-05	1980-01-16	Methode de preparation de polyphosphites aromatiques

Country Status (5)

Country	Link
JP (1)	JPS55104321A (fr)
CA (1)	CA1136152A (fr)
DE (1)	DE3003984A1 (fr)
FR (1)	FR2447927B1 (fr)
GB (1)	GB2041938B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3036391A1 (de) *	1980-09-26	1982-05-13	Bayer Ag, 5090 Leverkusen	Neue hydroxyphenylgruppen enthaltende phosphorigsaeureester, verfahren zur ihrer herstellung und ihre verwendung als stabilisatoren fuer thermoplastische polyester
US4413077A (en) *	1981-06-22	1983-11-01	Borg-Warner Chemicals, Inc.	Oligomeric aromatic polyphosphites
US5652282A (en) *	1995-09-29	1997-07-29	Minnesota Mining And Manufacturing Company	Liquid inks using a gel organosol
US5919966A (en) *	1998-03-26	1999-07-06	General Electric Company	Process for the preparation of spiro bis-phosphites
WO2003097720A1 (fr)	2002-05-20	2003-11-27	Toray Industries, Inc.	Resine, compositions de resine, procede de production associe et moulages correspondants
EP2909213A4 (fr) *	2012-10-18	2016-06-08	Reliance Ind Ltd	Composés tétraoxa-diphosphaspiro

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3053878A (en) *	1961-05-23	1962-09-11	Weston Chemical Corp	Pentaerythritol phosphite esters
NL298956A (fr) *	1962-10-08
FR1384809A (fr) *	1963-11-28	1965-01-08	Kuhlmann Ets	Nouveaux esters phosphoreux, procédé pour leur fabrication et applications desdits esters
GB1505044A (en) *	1976-09-20	1978-03-22	Borg Warner	Process for preparing dialkyl pentaerythritol diphosphite

1980
- 1980-01-16 CA CA000343754A patent/CA1136152A/fr not_active Expired
- 1980-01-29 GB GB8002969A patent/GB2041938B/en not_active Expired
- 1980-01-31 FR FR8002093A patent/FR2447927B1/fr not_active Expired
- 1980-02-04 DE DE19803003984 patent/DE3003984A1/de not_active Ceased
- 1980-02-05 JP JP1294880A patent/JPS55104321A/ja active Pending

Also Published As

Publication number	Publication date
GB2041938B (en)	1983-04-27
FR2447927A1 (fr)	1980-08-29
JPS55104321A (en)	1980-08-09
FR2447927B1 (fr)	1985-12-20
DE3003984A1 (de)	1980-08-07
GB2041938A (en)	1980-09-17

Legal Events

Date	Code	Title	Description
1999-11-23	MKEX	Expiry

Publication	Publication Date	Title
US4305866A (en)	1981-12-15	Polyolefins stabilized with cyclic diphosphites
CA1303624C (fr)	1992-06-16	Fluorophosphites aromatiques antioxydants
US3006885A (en)	1961-10-31	Stabilized polyolefin compositions
EP2944644B1 (fr)	2017-11-01	Composé à base de spiro bis-phosphite et utilisations de celui-ci
CA1117963A (fr)	1982-02-09	Stabilisateurs
EP0516006A1 (fr)	1992-12-02	Composés de 4,4'-biphénylènediphosphonite et leur utilisation
US4739000A (en)	1988-04-19	Antioxidant aromatic tetraphosphites
US4882374A (en)	1989-11-21	Dioxaphosphorinane compounds and polyolefin compositions sabilized therewith
US4724247A (en)	1988-02-09	Antioxidant aromatic diphosphites
US4427813A (en)	1984-01-24	Polycarbonate containing a bis(cyclic phosphate) as a thermal stabilizer
GB2041938A (en)	1980-09-17	Process for Preparing Aromatic Polyphosphites
EP0363270A1 (fr)	1990-04-11	Phosphites cycliques et compositions stables de polymères
CA1157035A (fr)	1983-11-15	Diphosphites stabilisees hydrolytiquement utilises comme anti-oxydants
US4104217A (en)	1978-08-01	Carbonate ester stabilizers for polymers
EP0033395B1 (fr)	1986-05-28	Phosphites de 2,6-butylephényle ditertiaire et compositions de résines synthétiques contenant ces phosphites
US4413077A (en)	1983-11-01	Oligomeric aromatic polyphosphites
US3560434A (en)	1971-02-02	Enhancement of resistance of olefin polymers to copper-catalyzed oxidative degradation
CA2119319A1 (fr)	1994-09-23	Esters cycliques d'acide phosphoreux et procedes pour leur production
WO2014043203A1 (fr)	2014-03-20	Ignifugeant à base de polyphosphonate fonctionnalisé stable à l'hydrolyse
EP0234915B1 (fr)	1993-07-21	Compositions de polyester aromatique stabilisées
US3859236A (en)	1975-01-07	Stabilized vinyl halide polymer compositions
CA1240691A (fr)	1988-08-16	Dioxaphosphepines et dioxaphosphocines dibenzo substituees
US3686367A (en)	1972-08-22	3-hydroxy-4-benzoyphenyl cyclic phosphates
CA1200038A (fr)	1986-01-28	Polyethylene lineaire stabilise de faible densite
US4130540A (en)	1978-12-19	Olefin polymers stable to copper