• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    This invention relates to the production of new high molecular weight polymers with nitrogen-containing functional groups. New polymers can be used as additives that lower the cloud point of middle distillates of petroleum hydrocarbons (heat, gas oil). The invention makes it possible to increase the effectiveness of the additive by 2-4 times by carrying out the copolymerization of an ester of the formula CH) C- where COORo L, R is H, R is C-C -alkyl, with maleic anhydride and ob-olefin containing 18 -40 carbon atoms, when heated in the presence of a radical initiator, followed by condensation of the resulting copolymer with a compound containing one primary amino group. As the latter, one or more compounds of the formulas R - NH - - (CH) -, - H are used, where t O or; R is a linear C, -C2-alkyl radical; BUT -, where R, is C5-C, o-alkylene radical; R4 is O-C (CH), -H, where n is I or 2, R C-Cr л alkyl radicals, and Rg-Isl- (CH2) Re where Rj, Rg are Cg-C, J-alkyl radicals. The copolymerization is carried out at a molar ratio of ester, maleic anhydride and olein 0.25 - 0.5: 0.5 - 0.75: 0.5. The condensation is carried out at an equimolar ratio of soy; 1, inen,. containing a primary amino group, and maleic anhydride. This effectiveness of the additive is also achieved by a second variant of the method - by radical copolymerization of 2-ethylhexylacrylate with the product of the interaction of maleic anhydride and an equimolar amount of a mixture of fatty amines RNHj, where R is a linear C, -C, g-alkyl radical, with a c6-olefin containing 22-30. carbon atoms; The copolymerization is carried out at an equimolar ratio of the reactants in the medium of the hydrocarbon solvent in the presence of a radical initiator with heating. 2 s, p. f-ly, 7 tab. § (Y) 4; i оо О5 00 СХ) CN
    公开号:SU1436884A3
    申请号:SU833607638
    申请日:1983-06-03
    公开日:1988-11-07
    发明作者:Гарапон Жак；Силльон Бернар；Дамен Бернар；Лежер Робер
    申请人:Энститю Франсэ Дю Петроль；Элф Франс (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to the field of high-molecular compounds, specifically to the preparation of new copolymers with nitrogen-containing, and their functional groups. The resulting compounds can be used as additives that lower the cloud point of middle distillates of petroleum hydrocarbons (fuels, gas oil).
    The aim of the invention is to increase the effectiveness of the additive.
    Example 1.a. 73.5 g (0.75 mol) of maleic anhydride, then 182 g (0.5 mol) of the alpha-olefins fraction 5 consisting of
    The solvent, up to a dry matter content of 50%, is the mother liquor of additive I.
    Example 2: Under conditions of example 16, the terpolymer prepared according to example 1a is condensed with a fraction of primary aliphatic amines, the alkyl part of which contains about 1% chains containing 14 carbon atoms, 5% chains containing 16 carbon atoms , 42% of chains containing 18 carbon atoms, 12% of chains containing 20 carbon atoms, and 40% of chains containing 22 carbon atoms. In this way, an additive solution II is obtained.
    Example Z. In the conditions of Example 16, the condensation of thermo
    approximately J% olefin, having 22 aro-jQ polymer, prepared according to the example of carbon, from 30% olefinj containing 24 carbon atoms, 39% olefin containing 26 carbon atoms, 20% olefin containing 28 carbon atoms, and 10% olefin containing 25–30 carbon atoms, and 200 ml of a solvent consisting of an oil fraction distilled at a temperature of from 120 to 250 ° C are added. The reaction mixture is kept at 80 ° C for 1 hour while stirring, and then slowly introduced 92 g (0.5 mol) of 2-ethylhexyl acrylate and .2.5 g of benzoyl peroxide. The heating
    thirty
    py 1a, with a fraction of N-alkyl-1,3-diaminopropanes, the alkyl parts of which contain on average 1% chains containing 14 carbon atoms, 28% chains containing 14 carbon atoms, 28% chains containing 16 carbon atoms, and 71% of chains, containing 18 carbon atoms. As a result of this reaction, additive III is obtained,
    Example 4 Under the conditions of example 16, a terpolymer prepared according to example 1a is condensed with a fraction of N-alkyl-1,3-diaminopropanes, the alkyl parts of which contain about 1% of chains containing 14 carbon atoms, 5% chains containing 16 carbon atoms, 42% chains containing 18 carbon atoms, 12.% chains containing 20 carbon atoms and 40% chains containing 22 carbon atoms. As a result of the reaction of this reaction, an IV is obtained.
    the reaction mixture is conducted for 12 hours at 80 ° C, resulting in a terpolymer in solution in the form of a light yellow viscous liquid,
    b. In the TOT, however, to the previously obtained solution of 210 g (which corresponds to 0.75 molar equivalents of the primary amine) fractions of primary aliphatic amines, the alkyl parts of which contain on average 1% of chains containing 14 carbon atoms, 28% of chains containing 16 carbon atoms, and 71% of chains containing 18 carbon atoms, then 150 ml of the solvent used in step a are added so that the content in the dry matter solution is in the order of 60%,
    After heating at 90 ° C for 2 hours, a light yellow solution is obtained, which has a high viscosity, the IR spectrum of which indicates the presence of imide absorption bands.
    This solution, which by the addition of the same solution
    jQ of polymer prepared according to example 25
    thirty
    35
    4o
    45
    55.
    50
    py 1a, with a fraction of N-alkyl-1,3-diaminopropanes, the alkyl parts of which contain on average 1% chains containing 14 carbon atoms, 28% chains containing 14 carbon atoms, 28% chains containing 16 carbon atoms, and 71% of chains, containing 18 carbon atoms. As a result of this reaction, additive III is obtained,
    Example 4 Under the conditions of example 16, a terpolymer prepared according to example 1a is condensed with a fraction of N-alkyl-1,3-diaminopropanes, the alkyl parts of which contain about 1% of chains containing 14 carbon atoms, 5% chains containing 16 carbon atoms, 42% chains containing 18 carbon atoms, 12.% chains containing 20 carbon atoms and 40% chains containing 22 carbon atoms. As a result of the reaction of this reaction, an IV is obtained.
    Example 5. The terpolymer prepared according to Example 1a is condensed with 1-amino hexanol-b according to the procedure of Example 16. As a result of this condensation, additive V is obtained,
    Example 6 The operation is carried out according to example 16, replacing the fraction of aliphatic amines with an equimolar amount of 1,3-H-3- (2,4,6-trimethyl deeth:) - 3-hydroxypropyl-diaminopropane. The resulting product is an additive VI.
    Example 7, Work according to example 16, replacing the fraction of aliphatic-.
    comic amino v at an equimolar amount of 1,3-, VD-didodecylaminopropane. The condensation product is an additive VII.
    Example 8. According to the conditions described in Example 1a, two thermopolymers are prepared using an alpha-olefin fraction consisting of about 1% olefin containing 18 carbon atoms, 49% olefin containing 20 carbon atoms, 42 % olefin containing 22 carbon atoms, and 8% olefin containing 24 carbon atoms.
    2% alcohols containing 14 atoms in lerode, 51% alcohols containing 16 carbon atoms, 14% alcohols containing 20 carbon atoms, and 3% alcohols containing 22 carbon atoms. As a result of condensation with amines according to example 16, an additive XII is obtained.
    Example 13. The operation is carried out according to Example 10, but to obtain polymer ter, an equivalent of a semi-molar fraction of methacrylate alcohols of the following approximate 20 is introduced into the reaction.
    25
    thirty
    35
    C. With these two new copolymers 15tava: 13% containing 8 atoms with coal, the same fraction of aliphatic amines as used in example 16 is condensed, according to the method described in example 16. After condensation, additive VIII is obtained.
    Example 9 The operation is carried out according to example 8, but to obtain a terpolymer, a fraction of olefins containing about 22% olefins containing 28 or less carbon atoms and 7% olefins containing up to 40 carbon atoms is used. As a result of condensation with the said copolymer of the amine fraction described in Example 16, additive IX is obtained.
    Example 10. Under the same experimental conditions as described in. Sanaas in Example 1a are obtained with terpolymers using the long chain acrylate fraction consisting of approximately 7% alcohols containing 18 carbon atoms, 58% alcohols containing 20 carbon atoms, 30% alcohols containing 22 atoms carbon, and 3% alcohols containing 24 carbon atoms in an amount equivalent to 0.25 mol by weight. After condensation, which is described in Example 16, additive X is obtained.
    Example 11. The procedure according to Example 10 is performed, but 0.5 mol of butyl acrylate is used to prepare the terpolymer, and a slight excess inert gas is maintained during the polymerization reaction in order to avoid butyl acrylate evaporation. As a result of condensation with amines according to Example 16, additive XI is obtained.
    Example 12. The operation is carried out according to example 10, but to obtain a terpolymer i, an equivalent of 0.5 mol of methacrylates fraction of various alcohols is used, containing on average
    40
    Lerode, 15%, containing 10 carbon atoms, 20%, containing 14 carbon atoms, 14%, containing 16 carbon atoms, and 7%, containing 18 carbon atoms. As a result of the condensation of this new terpolymer with a fraction of amines used in Example 16, an additive XIII is obtained.
    The additives described are obtained in a solution in an oil fraction distilled at a temperature ranging from 120 to 250 ° C. Their concentration in said solution is usually 50% based on the solid product. The solutions obtained are the mother solutions of these additives, which are examined for the presence of activity, and added to the gas oils at the rate of 0.1% by weight of the mother liquor of the additive. Two fractions of the gas-oil company ARAMCO are used as gas oil, designated as G-1 and G-2.
    Characteristics of these fractions are given in table. one.
    Table I
    45
    50
    55
    2% alcohols containing 14 carbon atoms, 51% alcohols containing 16 carbon atoms, 14% alcohols containing 20 carbon atoms, and 3% alcohols containing 22 carbon atoms. As a result of condensation with amines according to example 16, an additive XII is obtained.
    Example 13. The operation is carried out according to Example 10, but to obtain a terpolymer, the equivalent of a semi-molar fraction of methacrylates of alcohols of the following example is introduced
    tava: 13% containing 8 carbon atoms
    Lerode, 15%, containing 10 carbon atoms, 20%, containing 14 carbon atoms, 14%, containing 16 carbon atoms, and 7%, containing 18 carbon atoms. As a result of the condensation of this new terpolymer with a fraction of amines used in Example 16, an additive XIII is obtained.
    The additives described are obtained in solution in an oil fraction distilled at a temperature ranging from 120 to 250 ° C. Their concentration in said solution is usually 50% based on the solid product. The resulting solutions are mother liquors of these additives, which are examined for activity, and added to the gas oils at the rate of 0.1% by weight of the mother liquor of the additive. Two fractions of the gas-oil company ARAMCO are used as gas oil, designated as G-1 and G-2.
    Characteristics of these fractions are given in table. one.
    Table I
    45
    50
    55
    For each composition obtained in this way, the values of two indicators are determined: cloud point and discharge temperature.
    The results of the determination of these values are given below in table. 2. Table 2
    Without notice; Additives are introduced at a concentration of 0.1% by weight of gas oil.
    Example 14. a. The same operations were carried out in the same sequence as in Example 1a, obtaining a terpolymer from 49 g (0.5 mol) maleic anhydride, 148 g (approximately 0.5 mol) of the alpha-olefin fraction, of 1% olefin containing 18 carbon atoms, 49% olefin containing 20 carbon atoms, 42% feline containing 22- carbon atoms, and 8% olefin containing 24 carbon atoms, and 169 g
    (0.5 mol) stearyl methacrylate,
    b. With the previously obtained terpolymer, 140 g (0.5 mol equivalent in primary amine) fractions of aliphatic primary amines, the alkyl part of which contains on average 1% of chains containing 14 carbon atoms, 28% of chains containing 16 atoms, described according to example b in the example b of the method 140 g (0.5 mol equivalent in primary amine) carbon, and 71% of chains containing 18 carbon atoms.
    The resulting solution is brought to a concentration equal to 50% of the dry product by means of a solvent consisting of an oil fraction distilled at a temperature ranging from 120 to 250 ° C. In this way, an XIV supplement stock solution is obtained.
    Example 15 A terpolymer was prepared according to the method described in example 14a using a 1,3-N-alkylaminopropane fraction consisting of amines having alkyl parts, containing on average 1% of alkyl chains containing 14 carbon atoms, 28% of chains containing 16 carbon atoms and 71% chains containing 18 carbon atoms,
    The resulting copolymer is introduced into condensation with a compound having primary amine functional groups according to the method described in example 16, in molar proportions described in example 14b. As a result of the reaction, an additive XV is obtained,
    Example 16, work according to example 15, but with terpolymer
    1-aminoundecanol-1 is condensed to give additive XVI,
    Example 17, The operation is carried out according to Example 15, but 3-docosyloxypropylamine is condensed with a thermolymer, resulting in additive XVII,
    Example 18 The operation is carried out according to Example 15, but 1,3-N, N, -dioctyl-diaminopropane is used as a compound containing a primary amino group. Additive XVIII is obtained from the reaction product,
    The activity of the additives obtained according to examples 14-18, defined 7143688ч
    by adding them to three fractions of m-characteristics of which are given in
    Zoyle, designated G-3, G-4-and G-5, table. 3,
    Table3
    Additives are introduced at concentrations of 0.2% (in some cases, 0.1%) by weight of gas oil.
    The yields of the compositions thus prepared are determined by the volume of Example 19. In this example, the anticorrosive effect of the additive according to example 1 is investigated.
    25
    Cloudiness, filterability limit and outflow temperature.
    The results are shown in Table. four.
    Table 4
    The product according to Example -1 is used in two gas oils D-1 and D-2 at a concentration of 0.01 wt.%.
    The corrosion resistance tests consist in the study of corrosion as a result of the action of synthetic seawater on cylindrical tubes made of grinding steel and iron, according to the standards of ASTM, test temperature 32.2 ° C, test duration 20 hours.
    In the case of both G-1 and G-2 gas oils, in the absence of additives, the test tubes are rusted to 100% of their surface, and in the case of both gas oils containing 0.01% by weight of additives, the test tubes are affected by 0% rust.
    Example 20 (claim 2).
    but. To a reactor equipped with a system
    mixing
    49 g (0.5 mol) are added
    500 cm of solvent is introduced into the reactor, consisting of a petroleum fraction distilled between 120 and 250 ° C, then 182 g (0.5 mol) of the ot-olefin fraction containing about 1% Cj olefins, 30% olefins C , .39% olefins C
    GB
    20% olefins and 10% oleic / maleic anhydride, 20 cm of dimethyne – fins Cj, 92 g (0.5 mol) of 2-ethylhexyltylformamide, and then 2.5 g of benzoyl peroxide in small por-strengthcrylate.
    Heating is maintained for 6 hours at 100 ° C. The compound obtained has
    Qi mi 140 g (0.5 mol) fractions of fatty | amines, the alkyl chains of which contain about 1% 0.4, 28% C, and
    .vir, light yellow solution, content of 71% C, g, addition, amine fraction — about 50% by weight of active
    18ths last 30 min. Reagents
    stir while stirring at ambient temperature for 30 minutes.
    Then, the same reactor, equipped with a condenser, is fed 51 g (0.5 mol) of acetic anhydride and 41 g of sodium acetate and held at 70 ° C with stirring for 2 hours. Degeneration results in the formation of a mixture of N-substituted imides
    thirty
    substances (Supplement XIX).
    b. The effectiveness of this additive, used at a concentration of 0.1% by weight, is determined by the cloud point, the limiting temperature of the filtration capacity and the pour point of the two gas oils G, and G, which have already been used in other examples.
    The results of measurements carried out according to standard methods are given in. Table. five.
    35
    -I
    +2
    -7
    To compare the effect of lowering the cloud point of middle distillates, achieved by the introduction of additives according to the invention, with the effect of the closest known products, comparative tests have been carried out
    Example 21 Comparative Testing Preparation 1, In the reactor VB-od t 243 g (1.0 mol) fractions
    five
    maleic acid and obtaining acetic acid. The contents of the reactor are poured into I l of water with stirring. N-substituted imides of maleic acid precipitate. They are filtered, washed in water and sutaat. 170 g of compound are obtained.
    b. The compound obtained in step a is reintroduced into the reactor, equipped with a stirring system, a condenser and an inert gas feed.
    500 cm of solvent is introduced into the reactor, consisting of a petroleum fraction distilled between 120 and 250 ° C, then 182 g (0.5 mol) of the ot-olefin fraction containing about 1% Cj olefins, 30% olefins C , .39% olefins C
    GB
    20% olefins and 10% olefins Cj, 92 g (0.5 mol) 2-ethylhexag of silcrylate 2.5 g of benzoyl peroxide.
    .vir, a light yellow solution containing about 50% by weight of active
    thirty
    substances (Supplement XIX).
    b. The effectiveness of this additive, used at a concentration of 0.1% by weight, is determined by the cloud point, the limiting temperature of the filtration capacity and the pour point of the two gas oils G, and G, which have already been used in other examples.
    The results of measurements carried out according to standard methods are given in. Table. five.
    one
    Table5.
    35
    -7
    -12
    -12
    50 C, 5-Cgo paraffin olefins, 98 g (1.0 mol) of maleic anhydride and 341 g of benzene. The mixture is stirred at 60 ° C and 9.7 g (0.04 mol) of benzoyl peroxide in the minimum amount of benzene are added. Heat the solution to 85 seconds for 10 hours. The reaction product is precipitated with methane. Hume and again dissolved in benzene. 290 g of copolymer are obtained.
    341 g of a 50% aqueous solution of a boiled copolymer in copolymer, 324 g (1.0 mol) of N-octadecenylpropylene diamine and 306 g of xylene are introduced into the reactor. The mixture is stirred at 180 ° C for 6 hours. Filter the mixture through celite. The resulting product will be referred to below as Additive A.
    Preparation 2. 0.5 g of azobisiso-butyronitrile are introduced into a solution of 32 g of stearyl acrylate, II g of maleic anhydride and 10 g of diisobutylene in 250 ml of toluene and the mixture is stirred at 90 ° C for 6 hours.
    From 100 ml of the solution obtained, the reaction product is precipitated with excess methanol and the precipitate is separated by filtration. The resulting terpolymer contains 48% stearylacrylate, 32% maleic anhydride and 20% diisobutylene,
    3.8 g of dimethylaminopropylamine are introduced into 100 ml of the obtained solution and stirred for 4 hours at 150 ° C. The obtained terpolymer will be referred to as Additive B.
    The additives L and B thus obtained are introduced at the rate of 0.05 wt.


    two gas oils, G, and G, used in the examples of the invention. Cloud points are measured by the standard method.
    The results are shown
    in tab. 6
    Table 6
    Additive
    Without additives
    + 2
    +6
    + 1
    +4
    20
    AT
    L
    +4,
    These results show that the effects of the known additives A and B 25 on the cloud point of the two gas oils G and Gj are very weak in contrast to the proposed additives.
    In tab. 7 shows the components
    to obtain the proposed additives
    Tavl chi
    0.5 I 0.75 I 0.5
    12
    12
    0.25 "0.75 I OpS 0.5 I 0 | G5 1 0.5 0.5 1 0.75 I 0.5
    0.5 I 0.75 I 0.5 0.5 I 0.5 I O,)
    -
    -h
    Formula
    13 and 3 about b
    1436884
    14
    reteen and where n 1 or 2;
    Kf). A method for producing an additive for lowering the cloud point of a middle petroleum distillate, comprising radical copolymerizing an ester of the general formula
     IS
    .R1
     With ROORСН2
    h
    where R is H, CH
    RI 3
    C | C - lk is the radical, maleic anhydride and olefin in a hydrocarbon solvent when heated in the presence of a radical initiator, followed by condensation to form a copolymer with a compound containing one primary amino group in an organic solvent when heated, due to the fact that effectiveness of the additive, as an olefin, use one or more linear (A-olefins containing 18-40 carbon atoms, as a compound containing one Lerva's amino group , - one or more compounds of general formulas
    R - NHfcCHj), - H,
    where ha O or 1;
    R - linear / C -C kilo radical;
    BUT - CHj, - Rj-NHi, where Rj is Su-gC, p-alkylene radical;
     ofCCHj), - H,
    1436884
    14
    e p 1 or 2;
    Cf C, j-C-VPKilny
    radicals.
    R5- J- {CH2)
    RS
    where R and R
    - Cd-C, 2-alkaline feces.
    for the sake of
    the copolymerization is carried out at a molar ratio of ester: maleic anhydride: olefin, respectively, 0.25-0.5: 0.5-0.75: 0.5, and condensation is carried out using compounds containing the primary amino group, amounts equivalent to maleic anhydride. 2. A method for preparing an additive for lowering the cloud point of a middle petroleum distillate, including radical copolymerization of 2-ethyl hexyl acrylate, maleic acid derivative and olefin when heated in a hydrocarbon solvent in the presence of a radical initiator, which is The goal is to increase the effectiveness of the additive; a mixture of linear olefins containing 22–30 carbon atoms is used as an olefin; the derivative of maleic acid is the product of the reaction of maleic olefins An anhydride with an equivalent amount of fatty amines of the general formula RNH, where R is a linear, g-alkyl radical, while sopstamimerizing is carried out at an equimolar ratio of 2-ethylhexyl acrylate, maleic acid derivative and olefin.
    权利要求:
    Claims (2)
    [1]
    Claim
    1. The method of producing additives to reduce the cloud point of a middle petroleum distillate, including radical copolymerization of an ester of the General formula
    ROORj where R <- H, CH 3 ; ''
    R 4 - C 4 -C g 4 -alkyl radical, maleic anhydride and olefin in a hydrocarbon solvent when heated in the presence of a radical initiator, followed by condensation of the resulting copolymer with a compound containing one primary amino group in an organic solvent with heating, characterized in that, in order to increase the effectiveness of the additive, one or more linear L-olefins containing 18-40 carbon atoms are used as an olefin, as a compound containing one primary amino group y, - one or more compounds of general formulas
    R is NH [(CH x ) 9 - NH] M - H, where m = 0 or 1;
    R is linear .s <4 - C 1g ~ alkyl or ene radical;
    BUT - CH 2 - R 3 - NH 2 , where R - C y T C, O ~ alkylene radical; ! r4- о [(sn 2 ) e - νη] π - And, where η = 1 or 2; g r
    R + - C |} -C 2r ~ alkyl radicals,
    5 R 5 -N- (CH 2 ) 3 -NH 2
    R 6 .
    where R 5 and R g are C 8 -C 1g alkyl radicals, the copolymerization being carried out at a molar ratio of ester: maleic anhydride: olefin, respectively 0.25-0.5: 0.5-0.75: 0.5 , a
    15, condensation is carried out using compounds containing a primary amino group in amounts equivalent to maleic anhydride.
    [2]
    2. A method of producing additives for
    20 lowering the cloud point of the middle petroleum distillate, including radical copolymerization of 2 ethylhexyl acrylate, a derivative of maleic acid and olefin when heated in a hydrocarbon solvent in the presence of a radical initiator, characterized in that, in order to increase the effectiveness of the additive, as
    30 olefins use a mixture of linear obolefins containing 22-30 carbon atoms as a maleic acid derivative - the product of the interaction of maleic anhydride with an equivalent amount of fatty amines of 35 new formulas of the general formula RNH 2 , where R is linear C, l -C ( b-alkyl radical while copolymerization is carried out at an equimolar ratio of 2-ethyl 4 0 hexyl acrylate, a derivative of maleic acid and olefin ^.
    类似技术:
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    同族专利:
    公开号 | 公开日
    DE3364705D1|1986-08-28|
    NO164109B|1990-05-21|
    EP0100248B1|1986-07-23|
    DK251983A|1983-12-05|
    EP0100248A1|1984-02-08|
    AU1537183A|1983-12-08|
    AU560249B2|1987-04-02|
    JPH0643453B2|1994-06-08|
    US4731095A|1988-03-15|
    CA1201722A|1986-03-11|
    FR2528066A1|1983-12-09|
    DK164114B|1992-05-11|
    ES522949A0|1984-10-16|
    DK164114C|1992-10-12|
    ES8500317A1|1984-10-16|
    NO164109C|1990-08-29|
    DK251983D0|1983-06-02|
    BR8302962A|1984-02-07|
    FR2528066B1|1985-02-22|
    JPS59131602A|1984-07-28|
    ZA834031B|1984-04-25|
    NO831997L|1983-12-05|
    引用文献:
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    FR1459497A|1964-12-10|1966-11-18|Chevron Res|Fuel oil additive|
    NL148099B|1966-03-17|1975-12-15|Shell Int Research|PROCEDURE FOR REDUCING THE FLOOD POINT OF A FUEL MIXTURE.|
    GB1268089A|1966-10-14|1972-03-22|Exxon Research Engineering Co|Method for preparing a petroleum residual fuel having improved flow characteristics|
    GB1317899A|1969-10-14|1973-05-23|Exxon Research Engineering Co|Liquid hydrocarbon compositions|
    US4160739A|1977-12-05|1979-07-10|Rohm And Haas Company|Polyolefinic copolymer additives for lubricants and fuels|
    US4320019A|1978-04-17|1982-03-16|The Lubrizol Corporation|Multi-purpose additive compositions and concentrates containing same|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR8209908A|FR2528066B1|1982-06-04|1982-06-04|
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