US1962564A - Fluorescent hydrocarbon - Google Patents

Fluorescent hydrocarbon Download PDF

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Publication number
US1962564A
US1962564A US564716A US56471631A US1962564A US 1962564 A US1962564 A US 1962564A US 564716 A US564716 A US 564716A US 56471631 A US56471631 A US 56471631A US 1962564 A US1962564 A US 1962564A
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United States
Prior art keywords
fluorescence
oil
lubricating oils
imparting
primuline
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Expired - Lifetime
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US564716A
Inventor
Kuhrmann Friedrich
Siebert Otto
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/003—Marking, e.g. coloration by addition of pigments
    • 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
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/007—Coloured or dyes-containing lubricant compositions
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/04—Well-defined cycloaliphatic 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/08—Aldehydes; Ketones
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated 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
    • C10M2215/16—Nitriles
    • 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
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles

Definitions

  • Our present invention relates to a method of imparting a desired fluorescence to the commercial lubricating oils.
  • aminophenylbenzoxazole or of derivatives therer of impart to the liquids in question a desired fluorescence.
  • the stimuline bases as obtainable by heating paratoluidine or xylidine with sulfur
  • aminophenylbenzthiazoles such as 2-(metaaminophenyl) -benzthiazole, 2-phenyl-5- aminobenzthiazole, or 2-phenyl-6-aminobenzoxazole
  • 2 (para-aminophenyl) -5-aminobenzoxazole 2 (meta aminophenyl) -5-aminobenzoxazole, 2-phenyl-5amino-'7-methylbenzoxazole
  • 2-(metaaminophenyl) -benzthiazole) such as 2-(metaaminophenyl) -benzthiazole, 2-phenyl-5- aminobenzthiazole, or 2-phenyl-6-aminobenzoxazole
  • phenyl-5-methyl-7-aminobenzoxazole 2-(paraaminophenyl)-5-amino-7-methylbenzoxazole, 2- (meta-aminophenyl) -5-amino-7- methylbenzoxazole, 2 (para-chlorophenyl) -5aminobenzoxazole, or 2-phenyl-6.6'-diaminodibenzoxazole.
  • Example.'100 liters of parafline oil (boiling between 300 to 350 C.) are mixed with 500 com.
  • a process of imparting a desired fluorescence to lubricating oils which comprises commingling the oil with a compound of the group consisting of aminophenylbenzylthiazoles and aminophenylbenzyloxazoles.
  • a process of imparting a desired fluorescence to lubricating oils which comprises commingling the oil with a compound of the group consisting of aminophenylbenzylthiazoles and aminophenylbenzyloxazoles in an amount not surpassing 0.01%.
  • a process of imparting a desired fluorescence to lubricating oils which comprises commingling the oil with the primuline bases in an amount not surpassing 0.01%.
  • a process of imparting a desired fluorescence to lubricating oils which comprises commingling the oil with the primuline bases in addition with a solvent assistant.
  • Lubricating oils showing a distinct fluores- "ence and containing a compound of the group consisting of aminophenylbenzylthiazoles and aminophenylbenzyloxazoles.
  • Lubricating oils showing a distinct fluorescence and containing primuline bases in an amount not surpassing 0.01% and a hydrocarbon of the benzene series as a solvent assistant.

Description

' Patented June 12, 1934 UNITED STATES PATENT OFFICE in Anh'alt, Germany, assignors to I. G. Farbenlndustrie Aktiengesellschaft, Frankfort on v the-Main, Germany No Drawing. Application September 23, 1931, Serial No. 564,716. In Germany September 30,
7 Claims.
Our present invention relates to a method of imparting a desired fluorescence to the commercial lubricating oils.
It is well known that it is desirable from a marketing point of view to impart a characteristic to these products, or to alter the genuine fluorescence of petroleum oils, since the trade has associated the fluorescence or an oil with quality.
We have found that certain bodies on solution 10 will impart to the liquid a fluorescence without in any way deleteriously affecting the quality of the finished oil. We have discovered that very small amounts of aminophenylbenzthiazole,
aminophenylbenzoxazole, or of derivatives therer of impart to the liquids in question a desired fluorescence. As such substances we enumerate, for instance, the following: the primuline bases as obtainable by heating paratoluidine or xylidine with sulfur, aminophenylbenzthiazoles, such as 2-(metaaminophenyl) -benzthiazole, 2-phenyl-5- aminobenzthiazole, or 2-phenyl-6-aminobenzoxazole, 2 (para-aminophenyl) -5-aminobenzoxazole, 2 (meta aminophenyl) -5-aminobenzoxazole, 2-phenyl-5amino-'7-methylbenzoxazole, 2-
phenyl-5-methyl-7-aminobenzoxazole, 2-(paraaminophenyl)-5-amino-7-methylbenzoxazole, 2- (meta-aminophenyl) -5-amino-7- methylbenzoxazole, 2 (para-chlorophenyl) -5aminobenzoxazole, or 2-phenyl-6.6'-diaminodibenzoxazole.
It is obvious that other equivalent products likewise may be used. The quantities we add to the oils may be varied in certain limits, generally 0.01% is sufllcient to obtain the desired effect. I A few simple comparative experiments should be made to determine the best kind of these products and the most suitable amount to employ with a particular oil. l
The following example illustrates the invention.
40 Example.'100 liters of parafline oil (boiling between 300 to 350 C.) are mixed with 500 com.
of a solution of fi-aminophenylbenzoxatole (cf.
Berichte der Deutschen Chemischen Gesellschaft,
vol. 32, page 1427) in benzene of 1% strength. A bluish fluorescence is obtained in the oil.
In imparting a fluorescence to the oils in question, it is not necessary to use the substances enumerated above in a chemically pure, state. The desired result is gained when using the raw products as obtained in their manufacture.
The compounds'mentioned above do not show a fluorescence in each organic liquid .and even when used with liquid hydrocarbons, a fluorescence is only gained when using the products in distinct proportions which, as stated above, generally are below 0.01%, and which easily are ascertainable in each case.
What we claim is:--
1. A process of imparting a desired fluorescence to lubricating oils, which comprises commingling the oil with a compound of the group consisting of aminophenylbenzylthiazoles and aminophenylbenzyloxazoles.
2. A process of imparting a desired fluorescence to lubricating oils, which comprises commingling the oil with a compound of the group consisting of aminophenylbenzylthiazoles and aminophenylbenzyloxazoles in an amount not surpassing 0.01%.
3. A process of imparting a desired fluorescence to lubricating oils, which comprises commingling the oil with the primuline bases in an amount not surpassing 0.01%.
4. A process of imparting a desired fluorescence to lubricating oils, which comprises commingling the oil with the primuline bases in addition with a solvent assistant.
5." Lubricating oils showing a distinct fluores- "ence and containing a compound of the group consisting of aminophenylbenzylthiazoles and aminophenylbenzyloxazoles.
6. Lubricating oils showing a distinct fluorescence and containing primuline bases. L
'7. Lubricating oils showing a distinct fluorescence and containing primuline bases in an amount not surpassing 0.01% and a hydrocarbon of the benzene series as a solvent assistant.
FRIEDRICH KUHRMA'NN. O'I'I'O SIEBERT.
US564716A 1930-09-30 1931-09-23 Fluorescent hydrocarbon Expired - Lifetime US1962564A (en)

Applications Claiming Priority (1)

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DE1962564X 1930-09-30

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FR (1) FR723380A (en)
GB (1) GB390188A (en)
NL (1) NL32931C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2508617A (en) * 1947-04-02 1950-05-23 Cities Service Oil Co Colored lubricating oil
US3076698A (en) * 1960-09-30 1963-02-05 Patent Chemicals Inc Fluidized petroleum additives
US3094488A (en) * 1959-11-23 1963-06-18 Exxon Research Engineering Co Radiation resistant mineral oils

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2508617A (en) * 1947-04-02 1950-05-23 Cities Service Oil Co Colored lubricating oil
US3094488A (en) * 1959-11-23 1963-06-18 Exxon Research Engineering Co Radiation resistant mineral oils
US3076698A (en) * 1960-09-30 1963-02-05 Patent Chemicals Inc Fluidized petroleum additives

Also Published As

Publication number Publication date
FR723380A (en) 1932-04-06
GB390188A (en) 1933-03-27
NL32931C (en) 1934-06-15

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