GB728728A - Improvements in antioxidants - Google Patents

Improvements in antioxidants

Info

Publication number
GB728728A
GB728728A GB26074/53A GB2607453A GB728728A GB 728728 A GB728728 A GB 728728A GB 26074/53 A GB26074/53 A GB 26074/53A GB 2607453 A GB2607453 A GB 2607453A GB 728728 A GB728728 A GB 728728A
Authority
GB
United Kingdom
Prior art keywords
benzyloxy
rubber
alkoxy
incorporated
tetrahydroquinolines
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB26074/53A
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.)
Uniroyal Inc
Original Assignee
United States Rubber Co
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.)
Filing date
Publication date
Application filed by United States Rubber Co filed Critical United States Rubber Co
Publication of GB728728A publication Critical patent/GB728728A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C11B5/0064—Heterocyclic compounds containing nitrogen in the ring
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3437—Six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • 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
    • C10M2215/22—Heterocyclic nitrogen 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • 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
    • C10M2215/30—Heterocyclic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

6-Alkoxy and 6-benzyloxy-2 : 2 : 4-trimethyl-1 : 2 : 3 : 4-tetrahydroquinolines are incorporated in synthetic rubber for protection against heat, light and air. An example is given of a composition containing butadiene-styrene copolymer, zinc propionate-stearate mizture, carbon, tar, sulphur, mercaptobenzthiazole and one of the above quinolines. Butadieneacrylonitrile copolymers may be treated similarly. The material may be vulcanized or unvulcanized, and the antioxidant can be incorporated by milling or mastication, or applied to the surface of rubber goods, or added to rubber solutions or dispersions in powder, paste or solution form. Other ingredients such as accelerators and softeners may be present.ALSO:The invention comprises 6-alkoxy and 6-benzyloxy - 2 : 2 : 4 - trimethyl - 1 : 2 : 3 : 4 - tetrahydroquinolines. These are prepared by passing acetone through the corresponding p-alkoxy or p-benzyloxy-anilines and reducing the resulting dihydroquinolines with sodium and ethanol. Compounds mentioned are the methoxy, ethoxy, isopropoxy, butoxy, hexyloxy, heptyloxy, dodecyloxy and benzyloxy derivatives. They are used as antioxidants (see Groups III, IV (a) and V).ALSO:6-Alkoxy and 6-benzyloxy-2 : 2 : 4-trimethyl-1 : 2 : 3 : 4-tetrahydroquinolines are incorporated in unsaturated fatty oils (e.g. vegetable oils) and petroleum oils and their derivatives (e.g. gasolines) for protection against heat, light and air.ALSO:6-Alkoxy and 6-benzyloxy - 2:2:4 - trimethyl - 1:2:3:4 - tetrahydroquinolines are incorporated in rubber for protection against heat, light and air. The rubber may be either vulcanized or unvulcanized, and the antioxidant can be incorporated by milling or mastication, or applied to the surface of rubber goods, or added to rubber solutions or dispersions in powder, paste or solution form. Other ingredients such as accelerators and softeners may be present.
GB26074/53A 1952-11-12 1953-09-22 Improvements in antioxidants Expired GB728728A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US728728XA 1952-11-12 1952-11-12

Publications (1)

Publication Number Publication Date
GB728728A true GB728728A (en) 1955-04-27

Family

ID=22110253

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26074/53A Expired GB728728A (en) 1952-11-12 1953-09-22 Improvements in antioxidants

Country Status (1)

Country Link
GB (1) GB728728A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0072349A2 (en) * 1981-08-10 1983-02-16 Ciba-Geigy Ag Tetrahydroquinoline as an antioxidant for lubricants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0072349A2 (en) * 1981-08-10 1983-02-16 Ciba-Geigy Ag Tetrahydroquinoline as an antioxidant for lubricants
EP0072349A3 (en) * 1981-08-10 1984-07-25 Ciba-Geigy Ag Tetrahydroquinoline as an antioxidant for lubricants
US4692258A (en) * 1981-08-10 1987-09-08 Ciba-Geigy Corporation Tetrahydroquinolines as antioxidants for lubricants

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