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
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
  • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
  • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
  • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
  • C07C2/08—Catalytic processes
  • C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
  • C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
  • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
  • C09J123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
  • C09J123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
  • C09J123/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
  • C07C2527/06—Halogens; Compounds thereof
  • C07C2527/08—Halides
• • 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
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • C10M2205/026—Butene
• • 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

• Rhine, Germany assiznors to E. Farhe'nindusttie dirtiengeeellschatt, Frankfort cn themriain, Germany ,No Drawing. Originai application July 21, 1932,
• hydrocarbon mixtures in particular those having a boiling point above 200 C., and especially those boiling above about 325 C. at ordinary pressure, for example lubril0 eating oils or greases or hard or soft parafiln wax,
• the polymer- A 40 ized iso-olefines in an amount of from a fraction of one per cent up to about 10 per cent with reference to the hydrocarbon mixtures to be improved, but the amount added may also be much higher, as for example about 20 or 35 or even 545 per cent.
• oils are necessary which on the one hand still have a satisfactory viscosity at high tempera- 5'0 tures, as for example from to 150 C., and;
• the'present invention oils can be prepared which correspond to a great extent to these require ments and which are far superior to the special automobile oils hitherto in commerce.
• the effect of the addition of the said polymerized iso-olefines is shown in the following table of examples.
• the oils used in experiments A, B, C, D, and E are mineral oils of the type of the commercial light to medium machine oils.
• Experiments A, B, C, C", D, and E show the efiect of the addition of an iso-butylene polymerization product.
• Experiments F, G, and H are the tests of special automobile oils. In all cases the temperatures are given in degrees C.
• the viscosity index indicates the value of the oil in that as the index value increases, the qual ity of the oil improves.
• Viscosity Setting Flash- Density Ekpt' index point point at 20 From the table it can be seen that the addition of the highly polymerized isobutylene products considerably improves the oils.. The resulting improved oils have even a higher viscosity index than special automobile oils or high value.
• Polymerized isobutylene is added in an amount of from 1 to 4 per cent to paraffin wax having a strong tendency to form crystals and which when employed for casting candles causes the formation of fissures.
• the candles cast with the mixture thus obtained do not show fissures to a substantial degree and fissures or points of crystallization still formed disappear after 1 or 2 days.
• the candles are uniformly transparent.
• the production of the polymerized iso-olefines to be added to the hydrocarbon products is effected by polymerization of the iso-olefines in the presence of suitable catalysts, preferably Volatilizable inorganic halides, such as boron fluoride, boron fluoride charged with hydro fluoric acid, phosphorus tri-fluoride, phosphorus pentafluoride, aluminum chloride, preferably in statu nascendi, such as aluminum chloride as is formed by allowing hydrogen chloride to act on aluminium, or solutions or double compounds of the said halides, while cooling so strongly that no sudden substantial increase in temperature occurs.
• suitable catalysts preferably Volatilizable inorganic halides, such as boron fluoride, boron fluoride charged with hydro fluoric acid, phosphorus tri-fluoride, phosphorus pentafluoride, aluminum chloride, preferably in statu nascendi, such as aluminum chloride as is formed by allowing hydrogen chlor
• the said catalysts may be employed as such or together with substances such as phenol or cresol, in which they dissolve without decomposition, whether with the formation of real solutions, or with the formation of double compounds.
• the strong cooling prevents the undesired too rapid reaction, which leads to products not having the desired high molecular weight, and furthermore the loss in isobutylene which would occur by a It may be advantageous not to bring the catalyst into contact with the isobutylene at once but gradually.
• By moving the isobutylene for example by stirring, the removal of the reaction heat is favoured and local superheating is avoided;
• the polymerization of isobutylene is a strongly exothermic reaction.
• the cooling may be effected externally by means of cooling baths or internally by adding to the reacting substances cold materials which have no unfavourable influence on the reaction, as for example solid carbon dioxide.
• the catalysts may be employed in very small amounts; for example less than 1 per cent of catalyst is sufficient when boron fluoride is employed. It is, however, possible to use also higher percentages of catalysts, for example 3 or 5 per cent of aluminium chloride.
• Solvents such as pentane, may be present during the reaction.
• the resulting product is very viscous and of a from sticky to semi-solid or solid or rubber-like consistency; it is colorless and clear, soluble in liquid hydrocarbons in any proportion and may easily be depolymerized, without the formation of coke, to form gaseous and lower boiling hydrocarbons by heating, for example to a temperature of 300 C.
• the polymerized products having a molecular weight of more than 2000, as for example up to 10000 and more.
• the Coni'adsoncoke-test of these products is very low and not far from zero; it amounts for example to 0.01.
• Example 1 About 0.5 part of boron fluoride is led into 100 parts of liquid isobutylene which is cooled by a bath of carbon dioxide at 80 below zero 0. The polymerization soon sets in vigorously. By in tense stirring while maintaining the cooling, the considerable heat of reaction is led away so well that the temperature does not rise above 20 below zero C.
• the reaction product has a mean molecular weight of 3500. It is extremely viscous, may be drawn out into threads and, even at 200 C., it is still not liquid.
• Example 2 The process is similar to that in Example 1 except that before and during the leading in of boron fluoride solid carbon dioxide is thrown into the reaction material in order to maintain the temperature below from 60 to 70 below zero C. A product having a mean molecular weight of about 5000 is obtained. The product is as viscous as normal rubber masticated at 70 C. It is slightly sticky, colorless and clear.
• Example 3 A 20 per cent solution of isobutylene in pentane is kept at 40 below zero C. while leading in boron fluoride. After expelling volatile constituents with steam the product has a molecular weight of 2500. The product is much more soft and more sticky than that obtained according to Ex ample 2; it is colorless and clear and may be drawn into long threads.
• Example 4 A mixture of grams of isobutylene and 110 grams of normal butylene (mainly a-butylene) is polymerized as described in Example 2. After distilling off the normal butylene grams of a residue having a molecular weight of about 4000 are obtained.
• normal butylene mainly a-butylene
• Example -6 A mixture consisting of 900 grams of natural gas gasoline (distilling almost completely up to 60C., 60 grams of isobutylene and 290 grams of normal butylene. which mixture is liquid under a slight, super-atmospheric pressure, is polymerized as described in Example 2.
• the molecular weight may be increased by dc densable vapors evolved from the heating zone to return.
• the resulting isobutylene, when polymerized as described in Example 2 furnishes a polymerization product having a molecular weight of more than 5000.
• composition of matter comprising an un- For example the said polymerized hydrocarbon product boiling above 200 C. and an iso-oleiinic hydrocarbon polymer having a molecular weight of at least 1000 in. a viscosity improving amount.
• composition of matter comprising a petroleum lubricating oil and an iso-olefinic hydrocarbon polymer having a molecular weight of at least 3000 in a viscosity improving amount.
• composition of matter comprising an unpolymerized hydrocarbon product boiling about 200 C. and an isobutylene polymer having a molecular weight in excess oi 1000 in a viscosity improving amount.
• composition of matter comprising a pctroleum lubricating oil and a polymer of isobutylene having a molecular weight in excess of 5000 in a viscosity improving amount.
• a composition of matter comprising troleum lubricating oil and a polymer of isobutylene having a molecular weight between about 2000 and 10,000 in a viscosity improving amount.
• a composition of matter comprising an unpolymerized hydrocarbon product boiling above 200 C. and a polymer oi isobutylene having a molecular-weight between 2000 and 10,000 in a viscosity improving amount.
• composition of matter essentially comprising a parailln wax and a small amount 01 isobutylene polymer having a molecular weight of at least 1000.
• composition of matter essentially comprising a hydrocarbon insulating oil and a small amount of an isobutylene polymer having a molecular weight of at least 1000.
• a composition of matter essentially comprising a wax selected from the group consisting 01 hard and soft paraflln waxes. and a polymer oi" iso-olefine having a molecular weight oif at least 1,000, the amount of polymer not exceeding that of the wax.
• composition according to claim 9 in which the iso-oleiine polymer is a polymer .0! isobutylene.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Inorganic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• General Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Compositions Of Macromolecular Compounds (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

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Cited By (12)

• 0
  • NL NL35995D patent/NL35995C/xx active
• 1933
  • 1933-06-20 US US676680A patent/US2084501A/en not_active Expired - Lifetime

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