DE1960526A1 - Tri-[p-(2-butenyl)-phenyl]-phosphat und -phosphit - Google Patents

Tri-[p-(2-butenyl)-phenyl]-phosphat und -phosphit

Info

Publication number: DE1960526A1
Authority: DE; Germany
Prior art keywords: parts; butenyl; phenol; phosphate; weight
Prior art date: 1968-12-03
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

Application number

DE19691960526

Other languages

German (de)

English (en)

Inventor

Howell Frederic Harold

Wilfried Pickles

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.)

Novartis AG

Original Assignee

JR Geigy 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.)

1968-12-03

Filing date

1969-12-02

Publication date

1970-06-18

1969-12-02 Application filed by JR Geigy AG filed Critical JR Geigy AG

1970-06-18 Publication of DE1960526A1 publication Critical patent/DE1960526A1/de

Status Pending legal-status Critical Current

Links

OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title description 4
ZJOIMDZWSFOIDQ-UHFFFAOYSA-N tris(4-but-2-enylphenyl) phosphate Chemical compound C1=CC(CC=CC)=CC=C1OP(=O)(OC=1C=CC(CC=CC)=CC=1)OC1=CC=C(CC=CC)C=C1 ZJOIMDZWSFOIDQ-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 8
239000011368 organic material Substances 0.000 claims description 2
230000006641 stabilisation Effects 0.000 claims description 2
238000011105 stabilization Methods 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 22
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 20
CHQPRDVSUIJJNP-UHFFFAOYSA-N 4-but-2-enylphenol Chemical compound CC=CCC1=CC=C(O)C=C1 CHQPRDVSUIJJNP-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
229910019142 PO4 Inorganic materials 0.000 description 10
238000000034 method Methods 0.000 description 10
239000010452 phosphate Substances 0.000 description 10
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 8
-1 [p- (2-butenyl) -phenyl] -phosphite Chemical compound 0.000 description 7
239000000654 additive Substances 0.000 description 7
238000006366 phosphorylation reaction Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
230000000996 additive effect Effects 0.000 description 6
229910052782 aluminium Inorganic materials 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
239000000376 reactant Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
FHQBZLCAJCGWKV-ZZXKWVIFSA-N 2-[(e)-but-1-enyl]phenol Chemical compound CC\C=C\C1=CC=CC=C1O FHQBZLCAJCGWKV-ZZXKWVIFSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000002841 Lewis acid Substances 0.000 description 4
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
238000013459 approach Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
238000004508 fractional distillation Methods 0.000 description 4
150000007517 lewis acids Chemical class 0.000 description 4
238000002156 mixing Methods 0.000 description 4
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
230000026731 phosphorylation Effects 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
229920000915 polyvinyl chloride Polymers 0.000 description 4
239000004800 polyvinyl chloride Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
239000012530 fluid Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
230000000865 phosphorylative effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000013112 stability test Methods 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
DYZTWZPITCRCGU-UHFFFAOYSA-N (4-but-2-enylphenyl) dihydrogen phosphate Chemical compound CC=CCC1=CC=C(C=C1)OP(=O)(O)O DYZTWZPITCRCGU-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
238000005194 fractionation Methods 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229920001059 synthetic polymer Polymers 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
229910052726 zirconium Inorganic materials 0.000 description 2
VOYINLLVQMIKBT-UHFFFAOYSA-N 2-but-2-enylphenol Chemical compound CC=CCC1=CC=CC=C1O VOYINLLVQMIKBT-UHFFFAOYSA-N 0.000 description 1
ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 1
241000566113 Branta sandvicensis Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
238000007664 blowing Methods 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000002816 fuel additive Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
NBWMRMKVMFMPQN-UHFFFAOYSA-N tris(4-but-2-enylphenyl) phosphite Chemical compound C1=CC(CC=CC)=CC=C1OP(OC=1C=CC(CC=CC)=CC=1)OC1=CC=C(CC=CC)C=C1 NBWMRMKVMFMPQN-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
- 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
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric 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
- C07F9/06—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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids

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)
Oil, Petroleum & Natural Gas (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Compositions Of Macromolecular Compounds (AREA)

DE19691960526 1968-12-03 1969-12-02 Tri-[p-(2-butenyl)-phenyl]-phosphat und -phosphit Pending DE1960526A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB57190/68A GB1242608A (en)	1968-12-03	1968-12-03	New phosphate and phosphite esters and their production

Publications (1)

Publication Number	Publication Date
DE1960526A1 true DE1960526A1 (de)	1970-06-18

Family

ID=10478580

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19691960526 Pending DE1960526A1 (de)	1968-12-03	1969-12-02	Tri-[p-(2-butenyl)-phenyl]-phosphat und -phosphit

Country Status (4)

Country	Link
BE (1)	BE742531A (nl)
DE (1)	DE1960526A1 (nl)
FR (1)	FR2025087A1 (nl)
GB (1)	GB1242608A (nl)

1968
- 1968-12-03 GB GB57190/68A patent/GB1242608A/en not_active Expired
1969
- 1969-12-02 FR FR6941471A patent/FR2025087A1/fr not_active Withdrawn
- 1969-12-02 DE DE19691960526 patent/DE1960526A1/de active Pending
- 1969-12-02 BE BE742531D patent/BE742531A/xx unknown

Also Published As

Publication number	Publication date
BE742531A (nl)	1970-06-02
GB1242608A (en)	1971-08-11
FR2025087A1 (nl)	1970-09-04

Publication	Publication Date	Title
DE1618479C3 (de)	1974-11-21	Phosphorsäurearylestergemische und deren Verwendung als Weichmacher
DE1793689B2 (de)	1977-09-15	Gemisch von fluessigen triarylphosphorsaeureestern
DE2908439A1 (de)	1979-09-13	Stabilisatormischungen, verfahren zu ihrer herstellung und ihre verwendung
DE1270278B (de)	1968-06-12	Stabilisieren von Vinylchloridpolymerisaten
DE2135238B2 (de)	1978-06-08	Hydrolysebeständige Triarylphosphite und Verfahren zu ihrer Herstellung
DE2209102A1 (de)	1972-09-07	Metallderivate von 3,5-Di-tert.-butyl-4-hydroxyphenylpropionsäure
DE2747758C3 (de)	1982-04-29	Verfahren zur Herstellung von Isophthaloyldichlorid oder Terephthaloyldichlorid
DE2027443B2 (de)	1974-02-14	Verfahren zur Reinigung von Hydroxyalkylacrylaten oder Hydroxyalkylmethacrylaten
DE1960526A1 (de)	1970-06-18	Tri-[p-(2-butenyl)-phenyl]-phosphat und -phosphit
DE1493222A1 (de)	1969-04-10	Verfahren zur Herstellung von Diorganozinkverbindungen
DE2525120C2 (de)	1983-03-10	Verfahren zur Gewinnung von Dialkylaluminiumhalogeniden
DE2116355C3 (de)	1979-05-31	Verfahren zur Herstellung von Trialkylphosphoniumhalogeniden
DE1223383B (de)	1966-08-25	Verfahren zur Herstellung von Pentafluorophenylmagnesiumchlorid
DE2308817A1 (de)	1973-09-06	Feuerbestaendige polymere zusammensetzung
DE2522693C2 (de)	1982-10-14	Verfahren zur Herstellung von Bromarylphosphaten
DE1059450B (de)	1959-06-18	Verfahren zur Herstellung von Alkylaluminiumsesquichloriden
DE1801277C3 (de)	1978-05-24	Basische Organozinnverbindungen und ihre Verwendung als Stabilisatoren für Vinylhalogenid-Polymermassen
DD271331A5 (de)	1989-08-30	Verfahren zur Herstellung von zinnorganischen Stabilisatoren
AT237299B (de)	1964-12-10	Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen
DE1174315B (de)	1964-07-23	Verfahren zur Herstellung von Dialkylaluminiumhalogeniden
DE1920690C (de)	1971-09-09	Verfahren zur Herstellung von Biallyl verbindungen
AT213391B (de)	1961-02-10	Verfahren zur Herstellung von Carbonsäuren
DE2022357A1 (de)	1970-11-19	Neue polycyclische ungesaettigte Kohlenwasserstoffe und Verfahren zur Herstellung derselben
DE2112705C3 (de)	1976-03-11	Stabilisierung von Isopren in Lösungsmitteln
DE2111444B2 (de)	1974-01-10	Substituierte Dibenzofurane bzw. Dibenzothiophene und Verfahren zu deren Herstellung sowie deren Verwendung als Stabilisatoren