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US2900345A - Dielectric composition containing a phenoxypropionitrile - Google Patents

  • ️Tue Aug 18 1959

US2900345A - Dielectric composition containing a phenoxypropionitrile - Google Patents

Dielectric composition containing a phenoxypropionitrile Download PDF

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Publication number
US2900345A
US2900345A US412225A US41222554A US2900345A US 2900345 A US2900345 A US 2900345A US 412225 A US412225 A US 412225A US 41222554 A US41222554 A US 41222554A US 2900345 A US2900345 A US 2900345A Authority
US
United States
Prior art keywords
phenoxypropionitrile
dielectric
chlorinated
weight
electrical
Prior art date
1954-02-24
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 - Lifetime
Application number
US412225A
Inventor
Heininger Samuel Allen
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
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.)
1954-02-24
Filing date
1954-02-24
Publication date
1959-08-18
1954-02-24 Application filed by Monsanto Chemicals Ltd filed Critical Monsanto Chemicals Ltd
1954-02-24 Priority to US412225A priority Critical patent/US2900345A/en
1959-08-18 Application granted granted Critical
1959-08-18 Publication of US2900345A publication Critical patent/US2900345A/en
1976-08-18 Anticipated expiration legal-status Critical
Status Expired - Lifetime legal-status Critical Current

Links

  • 239000000203 mixture Substances 0.000 title description 21
  • MBVIMYRMRHPFKN-UHFFFAOYSA-N 2-phenoxypropanenitrile Chemical compound N#CC(C)OC1=CC=CC=C1 MBVIMYRMRHPFKN-UHFFFAOYSA-N 0.000 title description 17
  • 239000003990 capacitor Substances 0.000 description 12
  • 239000007788 liquid Substances 0.000 description 9
  • 239000003208 petroleum Substances 0.000 description 8
  • 238000009413 insulation Methods 0.000 description 6
  • 238000000354 decomposition reaction Methods 0.000 description 5
  • 229930195733 hydrocarbon Natural products 0.000 description 5
  • 229910052751 metal Inorganic materials 0.000 description 5
  • 239000002184 metal Substances 0.000 description 5
  • 239000000123 paper Substances 0.000 description 5
  • 125000004432 carbon atom Chemical group C* 0.000 description 4
  • 150000001875 compounds Chemical class 0.000 description 4
  • 239000003989 dielectric material Substances 0.000 description 4
  • 150000002430 hydrocarbons Chemical class 0.000 description 4
  • 239000001257 hydrogen Substances 0.000 description 4
  • 229910052739 hydrogen Inorganic materials 0.000 description 4
  • 238000000034 method Methods 0.000 description 4
  • UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
  • YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
  • 239000004020 conductor Substances 0.000 description 3
  • 230000002939 deleterious effect Effects 0.000 description 3
  • ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
  • -1 hydrogen halides Chemical class 0.000 description 3
  • 239000002480 mineral oil Substances 0.000 description 3
  • 150000002896 organic halogen compounds Chemical class 0.000 description 3
  • 239000010802 sludge Substances 0.000 description 3
  • 239000004215 Carbon black (E152) Substances 0.000 description 2
  • UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
  • 150000001555 benzenes Chemical class 0.000 description 2
  • 230000015572 biosynthetic process Effects 0.000 description 2
  • 239000002826 coolant Substances 0.000 description 2
  • 230000006866 deterioration Effects 0.000 description 2
  • USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
  • 239000011888 foil Substances 0.000 description 2
  • 150000008282 halocarbons Chemical class 0.000 description 2
  • 239000011551 heat transfer agent Substances 0.000 description 2
  • 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
  • 239000002655 kraft paper Substances 0.000 description 2
  • 150000002790 naphthalenes Chemical class 0.000 description 2
  • 150000002894 organic compounds Chemical class 0.000 description 2
  • 230000003647 oxidation Effects 0.000 description 2
  • 238000007254 oxidation reaction Methods 0.000 description 2
  • JBLPFPMLHWDSFR-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-ethylbenzene Chemical class CCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl JBLPFPMLHWDSFR-UHFFFAOYSA-N 0.000 description 1
  • GFSFRNLLEZNVEF-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-ethylbenzene Chemical class C(C)C=1C(=C(C(=C(C1)Cl)Cl)Cl)Cl GFSFRNLLEZNVEF-UHFFFAOYSA-N 0.000 description 1
  • JRNXNDCCMJUMKK-UHFFFAOYSA-N 1,2,3-trichloro-4-ethylbenzene Chemical class CCC1=CC=C(Cl)C(Cl)=C1Cl JRNXNDCCMJUMKK-UHFFFAOYSA-N 0.000 description 1
  • RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
  • BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical class C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
  • FAOXVMBWOUDDHJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanenitrile Chemical compound N#CC(C)(C)OC1=CC=CC=C1 FAOXVMBWOUDDHJ-UHFFFAOYSA-N 0.000 description 1
  • QSEFOSJSLFCWJA-UHFFFAOYSA-N 2-phenoxydodecanenitrile Chemical compound CCCCCCCCCCC(C#N)OC1=CC=CC=C1 QSEFOSJSLFCWJA-UHFFFAOYSA-N 0.000 description 1
  • IXAUFLAHUXISCH-UHFFFAOYSA-N 3-phenoxypropanenitrile Chemical compound N#CCCOC1=CC=CC=C1 IXAUFLAHUXISCH-UHFFFAOYSA-N 0.000 description 1
  • 229920000742 Cotton Polymers 0.000 description 1
  • SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
  • ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
  • 239000002253 acid Substances 0.000 description 1
  • 150000007513 acids Chemical class 0.000 description 1
  • 230000002411 adverse Effects 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
  • 239000010775 animal oil Substances 0.000 description 1
  • 150000001491 aromatic compounds Chemical class 0.000 description 1
  • RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
  • 238000009835 boiling Methods 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
  • YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
  • 239000000110 cooling liquid Substances 0.000 description 1
  • 230000007797 corrosion Effects 0.000 description 1
  • 238000005260 corrosion Methods 0.000 description 1
  • 125000002704 decyl 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])* 0.000 description 1
  • CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
  • 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 1
  • 230000000694 effects Effects 0.000 description 1
  • 229920001971 elastomer Polymers 0.000 description 1
  • 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
  • 238000004880 explosion Methods 0.000 description 1
  • 239000002360 explosive Substances 0.000 description 1
  • 239000003925 fat Substances 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
  • 238000005470 impregnation Methods 0.000 description 1
  • 239000011810 insulating material Substances 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
  • 239000000463 material Substances 0.000 description 1
  • 125000001421 myristyl 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])[H] 0.000 description 1
  • 150000002825 nitriles Chemical class 0.000 description 1
  • 125000001400 nonyl 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])[H] 0.000 description 1
  • 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 1
  • 239000003921 oil Substances 0.000 description 1
  • 235000019198 oils Nutrition 0.000 description 1
  • 150000002926 oxygen Chemical class 0.000 description 1
  • 125000000913 palmityl 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])[H] 0.000 description 1
  • 125000002958 pentadecyl 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])[H] 0.000 description 1
  • 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
  • 239000003209 petroleum derivative Substances 0.000 description 1
  • 229920000642 polymer Polymers 0.000 description 1
  • 238000002360 preparation method Methods 0.000 description 1
  • FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
  • 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
  • 230000001681 protective effect Effects 0.000 description 1
  • 238000010791 quenching Methods 0.000 description 1
  • 230000000171 quenching effect Effects 0.000 description 1
  • 238000005096 rolling process Methods 0.000 description 1
  • 229920006395 saturated elastomer Polymers 0.000 description 1
  • 239000000126 substance Substances 0.000 description 1
  • 150000001911 terphenyls Chemical class 0.000 description 1
  • 238000005979 thermal decomposition reaction Methods 0.000 description 1
  • 150000003613 toluenes Chemical class 0.000 description 1
  • 125000002889 tridecyl 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])[H] 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
  • 235000015112 vegetable and seed oil Nutrition 0.000 description 1
  • 239000008158 vegetable oil Substances 0.000 description 1

Images

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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/16—Nitriles
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts

Definitions

  • the present invention relates to a method of insulating elements in electrical apparatus and conducting elements generally, and also to compositions therefor. specically the invention relates to the use of phenoxypropionitriles, particularly in electrical apparatus such as capacitors, transformers, circuit breakers, cables and the like containing the above composition.
  • a further object is the provision of liquids which are applicable in insulating electrical conductors in electrical equipment. Other objects will appear hereinafter.
  • dielectric used in certain electrical equipment for the purpose of removing heat and of allowing the making of electrical contact in the absence of air or of explosive mixtures.
  • the requirements for such dielectrics are, among other things, very high resistance to the ow of electric currents, high stability to atmospheric conditions at ordinary and at somewhat elevated temperatures, high resistance to thermal decomposition, low vapor pressure, low congealing temperature, low inflammability and high ash point.
  • the dielectric should be a mobile liquid even at relatively low temperatures and should be a good heat transfer agent.
  • Another disadvantage of the mineral oils is that they tend to form deposits generally known as sludge during the period of their use. This is due to oxidation and decomposition and also results to some extent in the formation of acids which is equally undesirable.
  • the sludging of delectrics during use is a serious disadvantage and requires either replacement of the oil or treatment to remove the sludge and revivify the dielectric.
  • a satisfactory dielectricY liquid should not sludge or undergo substantial deleterious changeiduring use and it is one of the objects of this invention to provide a liquid which does not possess this undesirable disadvantage characteristic of the mineral oils..
  • Halogenated organic compounds more particularly halogenated aromatic compounds such as chlorinated biphenyl and chlorinated naphthalene are also highly useful electrical insulating materials because of their high dielectric constants, thermal stability, resistance to oxidation, non-arnmability and other valuable properties.
  • More- ICC For example, in transformers, circuit breakers and other electrical devices in which arcing occurs, the development of hydrogen halides as a result of the above decomposition presents a serious problem as they decrease the dielectric strength of the composition containing same and cause considerable damage by attaching paper insulation and corroding metal parts of the apparatus in which the composition is used.
  • the undesirable effect of the above decomposition is ⁇ further manifested when the above halogenated organic compounds are used as capacitor impregnants.
  • capacitors impregnated therewith undergo a characteristic type of deterioration which results in an ever increasing leakage current, a short capaitor life, visible localized decomposition of the dielectric and corrosion of the electrodes.
  • the decomposition sometimes results in an excessive increase in power factor of the dielectric material.
  • an object of the present invention to provide a method for the insulation of elements in elecn trical apparatus wherein the above objectionable properties are either completely eliminated or substantially reduced.
  • An additional object is to provide transformers, capacitors, circuit breakers, cables and the like containing a phenoxypropionitrile, whereby the deleterious action common to the prior art dielectric materials such as the deterioration of paper insulation and metal parts is eliminated or materially reduced. In this Way, it is possible to operate such apparatus so as to have a longer, useful life and a greater dielectric stability than similar capacitors not containing the said phenoxypropionitriles.
  • R is selected from the group consisting of hydrogen and alkyl radicals having from l to 18 carbon atoms and n is a whole number from l to 3.
  • Illustrative examples of compounds of the present invention are phenoxypropionitrile, methyl phenoxypropionitrile (also known as cresoxy propionitrile), and the other alkyl-substituted phenoxypropionitriles in which the alkyl radical may be ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl radicals, which may be saturated or unsaturated and may also be straight chain or branched including cycloaliphatic radicals.
  • Fig. l is a front elevation partly in section of a transformer; Fig. 2 illustrates a switch in a similar manner; Fig. 3 represents a rolled capacitor; Fig. 4 shows a sectional view of a portion of the electrodes and dielectric sheets of Fig. 3; and Fig. 5 is a side view of a cable, the casing being partly removed to permit the interior of the ⁇ parts to be seen.
  • the transformer illustrated in Fig. 1 comprises a casing 1, core 2, coils 3 insulated with manila paper, kraft paper, cotton or other iibrous insulation, insulating and cooling medium 4, lead-in busuhings 5, and suitable leads 6 connected to the coil assembly.
  • the insulating and cooling medium may consist of a phenoxypropionitrile such as -nonyl phenoxypropionitrile which may be employed as such or in combination with a petroleum oil. These two components may be employed in any proportions, such as from 10% to 91% by weight of the phenoxypropionitrile.
  • liquid hydrocarbons or halogenated hydrocarbons or mixtures thereof may also be used in combination with the phenoxypropionitrile as the insulating and cooling liquid and various other halogenated organic compounds may constitute a part of such compositions, such as for example, halogenated compounds of naphthalene, toluene, benzene, nitrodiphenyl or diphenyl oxide. l
  • the switch shown in Fig. 2 comprises a casing 7, ixe contacts 8 and 9, and movable contacts 10 and 11 which cooperate therewith.
  • the movable contacts are mounted upon a support 12 which in turn is operatively connected to actuating levers 13.
  • a phenoxypropionitrile is illustrative of a suitable arc quenching liquid which may be used in this device, either as the sole dielectric, or in combination with a petroleum oil or a halogenated hydrocarbon as described above.
  • the capacitor shown in Fig. 3 is made up of alternate layers of metal foil such as aluminum or tin foil separated by sheets of dielectric material. It is produced by interleaving two dielectric sheets, such as linen or kraft paper, with the metal foil, and rolling the interleaved sheets in the conventional manner. The rolled capacitor is then impregnated with the dielectric composition by any suitable process, such as vacuum impregnation with a phenoxypropionitrile. The capacitor is then placed in a protective case or otherwise used as desired.
  • Fig. 4 shows a section of one turn of the nished rolled capacitor iilustrating the alternate electrodes and dielectric layers. In accordance with the present invention, the finished capacitor contains a phenoxypropionitrile.
  • the cable of Fig. comprises a core 14, cable conductors 15, insulation consisting of paper or other suitable material 16 and a casing 17.
  • the space between the insulated conductors and the casing is filled with a phenoxypropionitrile or with a mixture of the same with a hydrocarbon or a liquid chlorinated organic compound as described above.
  • the following table illustrates the electrical properties of beta-nonylphenoxypropionitrile and beta-phenoxypropionitrile.
  • nitriles may also be employed in combination with another dielectric liquid, such as a hydrocarbon or chlorinated biphenyl, trichlorobenzene, chlorinated naphthalene, chlorinated diphenyl ketone, chlorinated diphenyl oxide, chlorinated diphenyl methane, chlorinated diphenyl ethane, chlorinated benzene, chlorinated toluene, chlorinated nitrodiphenyl, chlorinated alkylated benzenes, chlorinated alkylated biphenyl, ethyl trichlorobenzene, ethyl tetrachlorobenzene, ethyl pentachlorobenzene, chlorinated terphenyls, chlorinated quaterphenyls, chlorinated parafiinic hydrocarbons, chlorinated alicyclic hydrocarbons, chlorinated oxygen-containing organic compounds, chlorinated rubber, chlorobutadiene
  • An electrical insulating composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of a phenoxypropionitrile lIlOlIl in which R is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 18 carbon atoms, and n is a whole number from 1 to 3.
  • An electrical insulating composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of -nonylphenoxypropionitrile.
  • An electrical insulating composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of a phenoxypropionitrile substituted by an alkyl radical having from 1 to 18 carbon atoms.
  • a dielectric composition comprising from 9% to by weight of a petroleum oil in combination with from 10% to 91% by Weight of phenoxypropionitrile.
  • a dielectric composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of -nonylphenoxypropionitrile.
  • a dielectric composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of a phenoxypropionitrile substituted by an alkyl radical having from 1 to 18 carbon atoms.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Insulating Materials (AREA)

Description

Aug. 18, 1959 s. A. HEININGER .2,900,345

DIELECTRIC COMPOSITION CONTAINING A PHENOXYPROPIONITRILE Filed Feb. 24. 1954 United States Patent O P DIELECTRIC COB/[POSITION CONTAINING A PHENOXYPROPIONITRILE Samuel Allen Heininger, Dayton, Ohio, assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware Application February 24, 1954, Serial No. 412,225

7 Claims. (Cl. 252-63.'7)

The present invention relates to a method of insulating elements in electrical apparatus and conducting elements generally, and also to compositions therefor. specically the invention relates to the use of phenoxypropionitriles, particularly in electrical apparatus such as capacitors, transformers, circuit breakers, cables and the like containing the above composition.

It is an object of the present invention to provide new and improved methods of insulating elements and also to a dielectric composition therefor. A further object is the provision of liquids which are applicable in insulating electrical conductors in electrical equipment. Other objects will appear hereinafter.

The use of a dielectric is required in certain electrical equipment for the purpose of removing heat and of allowing the making of electrical contact in the absence of air or of explosive mixtures. The requirements for such dielectrics are, among other things, very high resistance to the ow of electric currents, high stability to atmospheric conditions at ordinary and at somewhat elevated temperatures, high resistance to thermal decomposition, low vapor pressure, low congealing temperature, low inflammability and high ash point. Preferably the dielectric should be a mobile liquid even at relatively low temperatures and should be a good heat transfer agent.

Iny commercial practice, high boiling fractions of petroleum distillates have been largely used for this purpose. These liquids do not satisfy all of the above-stated requirements. They are relatively poor heat transfer agents and under the conditions of their use they gradually decompose with the formation of undesirable products which adversely influence the electrical properties. Some of these products are tarry, and others are appreciably volatile and may present lire and explosion hazards.

Another disadvantage of the mineral oils is that they tend to form deposits generally known as sludge during the period of their use. This is due to oxidation and decomposition and also results to some extent in the formation of acids which is equally undesirable. The sludging of delectrics during use is a serious disadvantage and requires either replacement of the oil or treatment to remove the sludge and revivify the dielectric. A satisfactory dielectricY liquid should not sludge or undergo substantial deleterious changeiduring use and it is one of the objects of this invention to provide a liquid which does not possess this undesirable disadvantage characteristic of the mineral oils..

Halogenated organic compounds, more particularly halogenated aromatic compounds such as chlorinated biphenyl and chlorinated naphthalene are also highly useful electrical insulating materials because of their high dielectric constants, thermal stability, resistance to oxidation, non-arnmability and other valuable properties.

vHowever, it has been found that exposure to elevated temperatures and/or high voltages partially decomposes these compounds, thus liberating hydrogen halides which have an exceedingly deleterious action on the paper insulation and metal parts of electrical apparatus..

More- ICC For example, in transformers, circuit breakers and other electrical devices in which arcing occurs, the development of hydrogen halides as a result of the above decomposition presents a serious problem as they decrease the dielectric strength of the composition containing same and cause considerable damage by attaching paper insulation and corroding metal parts of the apparatus in which the composition is used. The undesirable effect of the above decomposition is `further manifested when the above halogenated organic compounds are used as capacitor impregnants. Thus, under high operating temperatures and direct current voltages, capacitors impregnated therewith undergo a characteristic type of deterioration which results in an ever increasing leakage current, a short capaitor life, visible localized decomposition of the dielectric and corrosion of the electrodes. Moreover, in the case of capacitors operating on alternating current, the decomposition sometimes results in an excessive increase in power factor of the dielectric material.

It is, therefore, an object of the present invention to provide a method for the insulation of elements in elecn trical apparatus wherein the above objectionable properties are either completely eliminated or substantially reduced.

An additional object is to provide transformers, capacitors, circuit breakers, cables and the like containing a phenoxypropionitrile, whereby the deleterious action common to the prior art dielectric materials such as the deterioration of paper insulation and metal parts is eliminated or materially reduced. In this Way, it is possible to operate such apparatus so as to have a longer, useful life and a greater dielectric stability than similar capacitors not containing the said phenoxypropionitriles.

Other objects and advantages of the present invention will become apparent to those skilled in the art as the description proceeds.

It has been discovered that the operation of electrical apparatus While insulating the elements thereof may be greatly improved by the use of phenoxypropionitriles interposed between the elements. Such compounds may be represented generically by the following general formula:

in which R is selected from the group consisting of hydrogen and alkyl radicals having from l to 18 carbon atoms and n is a whole number from l to 3. Illustrative examples of compounds of the present invention are phenoxypropionitrile, methyl phenoxypropionitrile (also known as cresoxy propionitrile), and the other alkyl-substituted phenoxypropionitriles in which the alkyl radical may be ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl radicals, which may be saturated or unsaturated and may also be straight chain or branched including cycloaliphatic radicals. The preparation of certain of the said phenoxypropionitriles is set forth in greater detail in copending application, Serial No. 412,063, led February 23, 1954, now abandoned.

For a more complete understanding of the present invention, reference is made to the accompanying drawings and the experimental data hereinafter presented in the specific examples.

Fig. l is a front elevation partly in section of a transformer; Fig. 2 illustrates a switch in a similar manner; Fig. 3 represents a rolled capacitor; Fig. 4 shows a sectional view of a portion of the electrodes and dielectric sheets of Fig. 3; and Fig. 5 is a side view of a cable, the casing being partly removed to permit the interior of the `parts to be seen.

The transformer illustrated in Fig. 1 comprises a casing 1,

core

2,

coils

3 insulated with manila paper, kraft paper, cotton or other iibrous insulation, insulating and

cooling medium

4, lead-in busuhings 5, and suitable leads 6 connected to the coil assembly. The insulating and cooling medium may consist of a phenoxypropionitrile such as -nonyl phenoxypropionitrile which may be employed as such or in combination with a petroleum oil. These two components may be employed in any proportions, such as from 10% to 91% by weight of the phenoxypropionitrile. Other well-known liquid hydrocarbons or halogenated hydrocarbons or mixtures thereof may also be used in combination with the phenoxypropionitrile as the insulating and cooling liquid and various other halogenated organic compounds may constitute a part of such compositions, such as for example, halogenated compounds of naphthalene, toluene, benzene, nitrodiphenyl or diphenyl oxide. l

The switch shown in Fig. 2 comprises a casing 7,

ixe contacts

8 and 9, and movable contacts 10 and 11 which cooperate therewith. The movable contacts are mounted upon a support 12 which in turn is operatively connected to actuating

levers

13. A phenoxypropionitrile is illustrative of a suitable arc quenching liquid which may be used in this device, either as the sole dielectric, or in combination with a petroleum oil or a halogenated hydrocarbon as described above.

The capacitor shown in Fig. 3 is made up of alternate layers of metal foil such as aluminum or tin foil separated by sheets of dielectric material. It is produced by interleaving two dielectric sheets, such as linen or kraft paper, with the metal foil, and rolling the interleaved sheets in the conventional manner. The rolled capacitor is then impregnated with the dielectric composition by any suitable process, such as vacuum impregnation with a phenoxypropionitrile. The capacitor is then placed in a protective case or otherwise used as desired. Fig. 4 shows a section of one turn of the nished rolled capacitor iilustrating the alternate electrodes and dielectric layers. In accordance with the present invention, the finished capacitor contains a phenoxypropionitrile.

The cable of Fig. comprises a core 14,

cable conductors

15, insulation consisting of paper or other

suitable material

16 and a casing 17. The space between the insulated conductors and the casing is filled with a phenoxypropionitrile or with a mixture of the same with a hydrocarbon or a liquid chlorinated organic compound as described above.

The experimental data hereinafter presented illustrates in a striking manner the dielectric properties of the above dielectric composition and the improvement possible in insulating elements in electrical apparatus therewith.

The following table illustrates the electrical properties of beta-nonylphenoxypropionitrile and beta-phenoxypropionitrile.

100 kc., 25 C. 100 kc., 100 C.

Resis- Compound tivity,

Dielectric Power Dielectric Power u constant factor, constant factor, ohm-em percent percent B-nonylphenoxypropionitrile 10. 88 0. 54 8. 26 7. l 520 B-

phenoxypropionitrile

3 7. 8 21,000

nitriles may also be employed in combination with another dielectric liquid, such as a hydrocarbon or chlorinated biphenyl, trichlorobenzene, chlorinated naphthalene, chlorinated diphenyl ketone, chlorinated diphenyl oxide, chlorinated diphenyl methane, chlorinated diphenyl ethane, chlorinated benzene, chlorinated toluene, chlorinated nitrodiphenyl, chlorinated alkylated benzenes, chlorinated alkylated biphenyl, ethyl trichlorobenzene, ethyl tetrachlorobenzene, ethyl pentachlorobenzene, chlorinated terphenyls, chlorinated quaterphenyls, chlorinated parafiinic hydrocarbons, chlorinated alicyclic hydrocarbons, chlorinated oxygen-containing organic compounds, chlorinated rubber, chlorobutadiene polymers, chlorinated fats, chlorinated vegetable oils, chlorinated animal oils, chlorinated mineral oils or mixtures of one or more of these. In such mixtures and phenoxypropionitrile may be employed in all proportions with the additional dielectric component.

What is claimed is:

1. An electrical insulating composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of a phenoxypropionitrile lIlOlIl in which R is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 18 carbon atoms, and n is a whole number from 1 to 3.

3. An electrical insulating composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of -nonylphenoxypropionitrile.

4. An electrical insulating composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of a phenoxypropionitrile substituted by an alkyl radical having from 1 to 18 carbon atoms.

5. A dielectric composition comprising from 9% to by weight of a petroleum oil in combination with from 10% to 91% by Weight of phenoxypropionitrile.

6. A dielectric composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of -nonylphenoxypropionitrile.

7. A dielectric composition comprising from 9% to 90% by weight of a petroleum oil in combination with from 10% to 91% by weight of a phenoxypropionitrile substituted by an alkyl radical having from 1 to 18 carbon atoms.

References Cited in the iile of this patent UNITED STATES PATENTS 1,856,186 Hofmann et al May 3, 1932 1,994,911 Ford Mar. 19, 1935 2,041,594 Clark May 19, 1936 2,143,685 Clark Jan. l0, 1939 2,377,689 Hyde lune 5, 1945 2,407,493 Hart Sept. 10, 1946 2,445,563 Clark July 20, 1948 2,450,650 Flowers Oct. 5, 1948 2,682,024 Kohman June 22, 1954

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Publication number Priority date Publication date Assignee Title
US3113993A (en) * 1961-05-17 1963-12-10 Monsanto Res Corp Electrical devices comprising biphenylyl silicate
US3129277A (en) * 1961-05-17 1964-04-14 Monsanto Res Corp Dielectric medium containing tercyclohexyl
EP2036582A1 (en) 1994-07-22 2009-03-18 United States Surgical Corporation Biobsorbable branched polymers containing units derived from dioxanone and medical/surgical devices manufactured therefrom
US20090312835A1 (en) * 2008-06-17 2009-12-17 Greatbatch Ltd. Dielectric fluid filled active implantable medical devices

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US1856186A (en) * 1925-11-24 1932-05-03 Ig Farbenindustrie Ag Preservation of oils
US1994911A (en) * 1933-02-15 1935-03-19 Westinghouse Electric & Mfg Co Corrosion-resisting product
US2041594A (en) * 1931-08-06 1936-05-19 Gen Electric Electrical capacitor
US2143685A (en) * 1935-05-25 1939-01-10 Gen Electric Electric device and dielectric materials therefor
US2377689A (en) * 1943-05-17 1945-06-05 Corning Glass Works Dielectric composition
US2407493A (en) * 1942-05-16 1946-09-10 Gen Electric Electric apparatus
US2445563A (en) * 1946-07-10 1948-07-20 Gen Electric Dielectric composition
US2450650A (en) * 1945-12-13 1948-10-05 Gen Electric Electric capacitor
US2682024A (en) * 1950-08-30 1954-06-22 Bell Telephone Labor Inc Electrical condenser and dielectric composition useful therein

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Publication number Priority date Publication date Assignee Title
US1856186A (en) * 1925-11-24 1932-05-03 Ig Farbenindustrie Ag Preservation of oils
US2041594A (en) * 1931-08-06 1936-05-19 Gen Electric Electrical capacitor
US1994911A (en) * 1933-02-15 1935-03-19 Westinghouse Electric & Mfg Co Corrosion-resisting product
US2143685A (en) * 1935-05-25 1939-01-10 Gen Electric Electric device and dielectric materials therefor
US2407493A (en) * 1942-05-16 1946-09-10 Gen Electric Electric apparatus
US2377689A (en) * 1943-05-17 1945-06-05 Corning Glass Works Dielectric composition
US2450650A (en) * 1945-12-13 1948-10-05 Gen Electric Electric capacitor
US2445563A (en) * 1946-07-10 1948-07-20 Gen Electric Dielectric composition
US2682024A (en) * 1950-08-30 1954-06-22 Bell Telephone Labor Inc Electrical condenser and dielectric composition useful therein

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3113993A (en) * 1961-05-17 1963-12-10 Monsanto Res Corp Electrical devices comprising biphenylyl silicate
US3129277A (en) * 1961-05-17 1964-04-14 Monsanto Res Corp Dielectric medium containing tercyclohexyl
EP2036582A1 (en) 1994-07-22 2009-03-18 United States Surgical Corporation Biobsorbable branched polymers containing units derived from dioxanone and medical/surgical devices manufactured therefrom
EP2301597A1 (en) 1994-07-22 2011-03-30 United States Surgical Corporation Bioabsorbable branched polymers containing units derived from dioxanone and medical/surgical devices manufactured therefrom
US20090312835A1 (en) * 2008-06-17 2009-12-17 Greatbatch Ltd. Dielectric fluid filled active implantable medical devices

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