CA1072535A - Pour point depressant additive - Google Patents
Pour point depressant additiveInfo
- Publication number
- CA1072535A CA1072535A CA235,563A CA235563A CA1072535A CA 1072535 A CA1072535 A CA 1072535A CA 235563 A CA235563 A CA 235563A CA 1072535 A CA1072535 A CA 1072535A
- Authority
- CA
- Canada
- Prior art keywords
- olefins
- pour point
- copolymers
- oil
- mole
- 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
Links
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
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
ABSTRACT OF DISCLOSURE
An oil-soluble copolymer, useful as a pour point depressant for lubricating oils, is composed of about equimolar amounts of C20-C24 1-olefins and an athylenically unsaturated dicarboxylic anhydride. The pour point activity may be enhanced by the inclusion of up to 1 mole of C8-C14 1-olefins per mole of C20-C24 1-olefins.
The copolymers are essentially free of olefinic unsaturation and have a number average molecular weight of from 1,000 to 20,000.
The copolymers are usefully admixed with lubricants in an amount of from 0.01 to 3 wt. %, based on the total weight of admixture.
An oil-soluble copolymer, useful as a pour point depressant for lubricating oils, is composed of about equimolar amounts of C20-C24 1-olefins and an athylenically unsaturated dicarboxylic anhydride. The pour point activity may be enhanced by the inclusion of up to 1 mole of C8-C14 1-olefins per mole of C20-C24 1-olefins.
The copolymers are essentially free of olefinic unsaturation and have a number average molecular weight of from 1,000 to 20,000.
The copolymers are usefully admixed with lubricants in an amount of from 0.01 to 3 wt. %, based on the total weight of admixture.
Description
~7Z5~5 l This invention relates to a lubricating oil addi~
2 tive and lubricating oils incorporating a minor proportion
3 of said additive to depress the pour poin~ o said oil.
4 The additi~e is a copolymer of straight-chain 1-olefins of ~rom 50 mole % to 100 mole % having 20 ~o 24 car~
6 bons and from 0 to 50 mole % having 8 to 14 carbons and an 7 ethylenlcally unsaturated dicarboxylic anhydride, prefer~
8 ably maleic anhydride, said l~ol~fins and said anhydride 9 being present in a~out equimolar ~mounts.
A wid~ variety of compositions comprising poly-11 meric materials derived ~rom the addition reaction o~ ~ ~
12 olefins and dicarboxylic alkenes have been described in the 3 literature as dispersants for fuels and lubricants and as 14 viscosity index improvers for lubricants. For example:
15 U.S. Pate~t 2,615~845 teaches that the copolymer o~ maleic 6 anhydride and a straight~chain ~ ~olefin having up to 20 17 carbon atoms which is su~sequently esterified with long, 18 straigh~Qchain, sa~urat~d alcohols in oxder to make lt suit-19 ably oil-soluble, can be usefull~ added to a mine~al lubri~
20 cating oil for pour point depression; and9 21 UOSo Patent 2~542,542 discloses the general pre-22 paration of copolymers of ethylene~l~2 dicarbosylic acids 23 and their derlvatives and ~ ~oleins contai.ning f~om 8 to 24 24 straight chain carbon atoms and teaches ~hat only copoly~
mers derived from ~ octadecene were useful as lubricating .
26 oil pour point depressants.
27 U.S. Patent 2,65$~479 polnts out that a factor o 28 particularly g~eat effect on ~he pour depressant activity of 29 acrylic ester polymers is the length of the alkyl side chains (apparently a unction of the oil solubilizing effect 31 of the alkyl side chain). This a~tor~ however, is further 32 limited by the conslderation that the "polymers of single . ~,~
~7'~535 1 esters are rarely pour point depressants"O
2 It is the purpose of this disclosure to teach the 3 utility of polymeric additives derived from the reaction o~
4 an ethylenically unsaturated dicarboxylic anhydride and at least 50 mole % of C20~c24 l~olefi~s to depress the pour 6 point o mineral oil lubricants.
'~ 7 Oil~soluble addition copolymers particuLarly use~
3 ful as po~r point depressants when compounded in lubrlcating : 9 oils in a minor amount~ e.gO OoOl to 1.0 wt. %, usually 0.1 10 to 0O3 wt. % based on the total composition, have been pre-11 pared and com~rise l~olefins of from 50 mole % to 100 mole 12 % having 20 to 24 carbon atoms and ~rom 0 to 50 mole % hav~
:. 13 ing 8 to 14 carbons and a dicarboxylic anhydride, said 1-14 olefin and said anhydride being present in about equimolar amounts.
16 Such sys~ems ~xhibit highly useful pour point de~
17 pressant characteristics when admixed with lubricants.
18 Thes~ copolym~rs can be ully esterified with al~
19 cohols of up to and including 8 carbon atoms to improve the pour point depressant ac~ yO
21 It has fur~her been found that oil~soluble copoly~
22 me~s of a mi~ture of at least 50 mol percent of l-olefins 23 having from 20 to X4 carbon atoms and the balance l-hexene ; 24 olefins and maleic anhydride, said l~oleins and maleic an-hydride being present in a~out equlmolar amounts9 upon es~i 26 fication with an alcohol o up to and including 8 carbons 27 exhi~its pour polnt depressant activity.
28 The copolymers of the invention result from the 29 addition reaction o~ abou~ equimolar amounts of l~olefins and an ethylenically unsaturated dicarboxyl.ic anhydride such 31 as maleic and itaconicO Maleic anhydride or a derivative is 32 preferredO
~ 3 .' "
~L~72535 1Such deriva~ives include those of the generic 2 formula~
4 Rl R2 S C ~C
6 l l 8 \ X
9 wherein Rl and R2 are hydrogen9 or a halogen and X is oxy~
gen, NX~ or NR3, wherein R3 is an alkyl group~ preferably 11 a Cl to C40 alkylO Suitable example~ of such derivatives 12 include itaconic anhydride, Nethyl male-imide, N hexyl male-13 imide, N-dodecyl maleimide, N~tetradecyl maleimide, N~eico-14 syl malei~ide9 Ntetxacosyl maleimide, chloromaleic anhy-dride and dichloro maleic anhydride~ The copolymers have 16 number average molecular weights in the range of about 17 1,000 to 30,000 and are more frequently in the range of 18 about 2,000 to 6,0000 19 A suitablP source for the C20~C24 1olefins is a commercial fraction consisting of about 90~95~/0 monoolefins 21 and with the typical composition 22 ~ Ye~ AEE~
23 ~ ~olefin 70 24 vinyLidene 20 Alternatively, the individual l~olefins~l-eicosene;
26 Z~methyl~l~eicosene; 3 methyl~l eicosene; l~heneicosene, 1-27 docosene; l~tricosene, l~tetracosene; and mix~ures thereo 23 as ~sired can be employed.
29 A suitable source for the C~C14 1ole~ins may be the individual l;olefins; l-oc~ene; 20me~hyl-l-heptene; 2,~, 31 4~trimethyl~1pentene; l~nonene; l~decene; l~dodecene; 1~
32 tridecene; l~tetradecene; l~undecene and mi~tures thereof 33 can be employedO
34The l-olefin content of the copolymer of the ~ ~ 7'~ 5 ~ S
1 invention has a range of S0 to 100 mole % C20~c24 l~olefin 2 and 0 to S0 mole ~/3 C~c~ olefinO
3 The reaction between the maleic anhydride and 1-4 olefins mixture can conveniently be carried out by mixing the olefins and maleic anhydride in about equal amounts, 6 and heating the mixture to a temperature of at least 50C., 7 preferably at leas~ 80~Co A free radical polymeriza~ion 8 promoter such as azo isobutylnitrile, benzoyl peroxide, t-9 butyl hydroperoxide or di~t~butyl peroxide is uscd.
The oil~soluble reactiQn products of this inven-11 tion can be incorporated in lubricating oil compositions, 12 e.gO automotive crankcase lubricating oils, in concentra-13 tions within the range of about OoOl to 200 wt. %, prefer-14 ably 0~1 to 0.5 w~. %, of the total composi~ion. The lubricants t~which the poiymeric products o~ this invention 16 can be added include not only hydrocarbon oils derived from 17 petroleum, tar sand or shale but also include synthetic 9ils 18 of the hydrocarbon or polyester variety and mixtures thçreof.
19 The additive may be conveniently dispensed as a concentrate comprising 20~60 par~s by weight, preerred 21 about 50 parts by weight o the additive dissolved in from 22 40 to 80 parts by weight of a mineral lubricating oil with 23 or without other additives being present.
24 The copolymers of the invention can be esterified with saturated alipha~ic alcohols of up to 8 carbon atoms to 26 impro~e the pour point depressant acti~ity o~ the copolymer.
27 l~ese alcohols can be eitheP straight or branched chain and 28 include methanol, ethanol, propanol, butanol, pentanol, 29 hexanol, heptanol, octanol, 2~ethyl hexanol, etc.
. .
For purposes of this disclosure a l~olefin is a 31 hydrocarbon which had a double bond between the Cl and C2 32 carbons and may or may not have another substituent on the w 5 -~7Z~35 1 C2 carbon, e.g. l~hexene and 2~methyl l-pentene.
2 This invention will be further understood by ref-3 erence to the following examples, which include preferred 4 embodiments of ihe invention.
6 A copolymer of (C20~G24) lDolef-Lns and maleic an-7 hydride was prepare~ by mixing 108 g. of maleic anhydride, 8 320 g. of C20~C2~ l~olefins3 400 mlO of ethylene dichloride, 9 and 2.4 g of Lucidol 70 (70% benzoyl peroxide and 30 wt. %
water) in a liter r~sin pot which was fitted with an agi~
11 tator, condens~r, thermometer3 nitrogen sparging tube and 12 heating mant~e. The mixture was heated to 38C.3 sparged 13 slightly with nitrogen and then heated to 72Co where it was 14 maintained for 3 hours with agitationO Therea~ter 0.9 g. of Lucidol 70 was added and polymerization continued for an ad-16 ditional 18 hours by maintenance at 72~80C~
17 The polymer may be fr ed of raw materials by pre~
18 cipitation in cold isopropanol or by dialysis against a rub~
19 ber membrane for thr~e hours with toluene.
21 A copolymer of ~C20l~2~) ~ C6 l~olefins and maleic 22 acid anhydride was p~epared by the procedure of Example 1 23 except that 182 g~ maleic anhydride9 324 gO of C20-c24 1-24 olefins and 68 g. of hexene~l was used. The copolymer prod-uct was insoluble in ~il at room temperature.
27 A copolymer of (C20~C2~) ~ C8 l olefins and maleic 28 anhydride was prepared by the procedure of Example 2 except 2~ that 92 g. of octene-l was used Ln place o~ hexeneol.
. .
31 A copolymer of (C20-C24) ~ C10 l-olefins and mal~ic 32 anhydride was prep~red by the procedure o~ Example 2 except *Trade Mark ~72~35 1 that 115 g. of decene l was used in place of hexene-l.
3 The product of Example 1, i.e. thP copolymer of 4 C20 C24 l~olefins and maleic anhydride was fully esterified with 2~ethyl hexanol using p~toluene sulfonic acid as the 6 catalyst and azeotxoping of~ the water of esteri~ication `7 with toluene.
8 EXAMPI~ 6 ; . 9 The product o~ Example 2, i.e. the copolymer of (C20-C24) ~ C6 l olefins and maleic anhydride, was fully 11 esterified with 2~ethyl hexanol using the procedure of 12 Example 5.
13 The copolymers prepared în Examples 1-6 had the 14 following properties~
Product Example Yield % Mol.Wt.*Mn %C %H
16 1 6~ ~00 71.511.6 - 17 2 67 5~00 71o 710~ 9 l8 3 ~7-~ ~7~0 71.~10.6 19 ~ 3000 72.7 7.5 ,~ 20 5 21 6 68 7000 74.511.6 22 *number average molecular weight determined by vapor 23 phase osmometry on Mechrolab Vapor Phase Osmometer 24 Model 310A.
The various copolymers described above were admix i 26 ed at room temperature by stirring with a lubricating oil 27 and subjected to an ASTM test which demonstrates the copoly-28 mers o~ the invention be highly e~fective pour point depres-29 sants as is apparent from ~he following table.
*Trade Mark ,; ~ .
7Z53~
TABL;E
2 Pour De ressan~ Activit 3 Product of ~i~u~
4 Ex~mple~dditivetD-e D~e-~cd 0-1 1 0.2 -15 6 2 insolubla 0 7 3 0.2 o20 8 4 0.2 ~20 9 5 0,2 ~25 6 0.2 ~25 11 *ASTM Test D~97. The treated oil is a mineral lubricat-:. 12 ing oil having a pour point of 0F. and a viscosity 13@210F. o about 44. 0SUSO
6 bons and from 0 to 50 mole % having 8 to 14 carbons and an 7 ethylenlcally unsaturated dicarboxylic anhydride, prefer~
8 ably maleic anhydride, said l~ol~fins and said anhydride 9 being present in a~out equimolar ~mounts.
A wid~ variety of compositions comprising poly-11 meric materials derived ~rom the addition reaction o~ ~ ~
12 olefins and dicarboxylic alkenes have been described in the 3 literature as dispersants for fuels and lubricants and as 14 viscosity index improvers for lubricants. For example:
15 U.S. Pate~t 2,615~845 teaches that the copolymer o~ maleic 6 anhydride and a straight~chain ~ ~olefin having up to 20 17 carbon atoms which is su~sequently esterified with long, 18 straigh~Qchain, sa~urat~d alcohols in oxder to make lt suit-19 ably oil-soluble, can be usefull~ added to a mine~al lubri~
20 cating oil for pour point depression; and9 21 UOSo Patent 2~542,542 discloses the general pre-22 paration of copolymers of ethylene~l~2 dicarbosylic acids 23 and their derlvatives and ~ ~oleins contai.ning f~om 8 to 24 24 straight chain carbon atoms and teaches ~hat only copoly~
mers derived from ~ octadecene were useful as lubricating .
26 oil pour point depressants.
27 U.S. Patent 2,65$~479 polnts out that a factor o 28 particularly g~eat effect on ~he pour depressant activity of 29 acrylic ester polymers is the length of the alkyl side chains (apparently a unction of the oil solubilizing effect 31 of the alkyl side chain). This a~tor~ however, is further 32 limited by the conslderation that the "polymers of single . ~,~
~7'~535 1 esters are rarely pour point depressants"O
2 It is the purpose of this disclosure to teach the 3 utility of polymeric additives derived from the reaction o~
4 an ethylenically unsaturated dicarboxylic anhydride and at least 50 mole % of C20~c24 l~olefi~s to depress the pour 6 point o mineral oil lubricants.
'~ 7 Oil~soluble addition copolymers particuLarly use~
3 ful as po~r point depressants when compounded in lubrlcating : 9 oils in a minor amount~ e.gO OoOl to 1.0 wt. %, usually 0.1 10 to 0O3 wt. % based on the total composition, have been pre-11 pared and com~rise l~olefins of from 50 mole % to 100 mole 12 % having 20 to 24 carbon atoms and ~rom 0 to 50 mole % hav~
:. 13 ing 8 to 14 carbons and a dicarboxylic anhydride, said 1-14 olefin and said anhydride being present in about equimolar amounts.
16 Such sys~ems ~xhibit highly useful pour point de~
17 pressant characteristics when admixed with lubricants.
18 Thes~ copolym~rs can be ully esterified with al~
19 cohols of up to and including 8 carbon atoms to improve the pour point depressant ac~ yO
21 It has fur~her been found that oil~soluble copoly~
22 me~s of a mi~ture of at least 50 mol percent of l-olefins 23 having from 20 to X4 carbon atoms and the balance l-hexene ; 24 olefins and maleic anhydride, said l~oleins and maleic an-hydride being present in a~out equlmolar amounts9 upon es~i 26 fication with an alcohol o up to and including 8 carbons 27 exhi~its pour polnt depressant activity.
28 The copolymers of the invention result from the 29 addition reaction o~ abou~ equimolar amounts of l~olefins and an ethylenically unsaturated dicarboxyl.ic anhydride such 31 as maleic and itaconicO Maleic anhydride or a derivative is 32 preferredO
~ 3 .' "
~L~72535 1Such deriva~ives include those of the generic 2 formula~
4 Rl R2 S C ~C
6 l l 8 \ X
9 wherein Rl and R2 are hydrogen9 or a halogen and X is oxy~
gen, NX~ or NR3, wherein R3 is an alkyl group~ preferably 11 a Cl to C40 alkylO Suitable example~ of such derivatives 12 include itaconic anhydride, Nethyl male-imide, N hexyl male-13 imide, N-dodecyl maleimide, N~tetradecyl maleimide, N~eico-14 syl malei~ide9 Ntetxacosyl maleimide, chloromaleic anhy-dride and dichloro maleic anhydride~ The copolymers have 16 number average molecular weights in the range of about 17 1,000 to 30,000 and are more frequently in the range of 18 about 2,000 to 6,0000 19 A suitablP source for the C20~C24 1olefins is a commercial fraction consisting of about 90~95~/0 monoolefins 21 and with the typical composition 22 ~ Ye~ AEE~
23 ~ ~olefin 70 24 vinyLidene 20 Alternatively, the individual l~olefins~l-eicosene;
26 Z~methyl~l~eicosene; 3 methyl~l eicosene; l~heneicosene, 1-27 docosene; l~tricosene, l~tetracosene; and mix~ures thereo 23 as ~sired can be employed.
29 A suitable source for the C~C14 1ole~ins may be the individual l;olefins; l-oc~ene; 20me~hyl-l-heptene; 2,~, 31 4~trimethyl~1pentene; l~nonene; l~decene; l~dodecene; 1~
32 tridecene; l~tetradecene; l~undecene and mi~tures thereof 33 can be employedO
34The l-olefin content of the copolymer of the ~ ~ 7'~ 5 ~ S
1 invention has a range of S0 to 100 mole % C20~c24 l~olefin 2 and 0 to S0 mole ~/3 C~c~ olefinO
3 The reaction between the maleic anhydride and 1-4 olefins mixture can conveniently be carried out by mixing the olefins and maleic anhydride in about equal amounts, 6 and heating the mixture to a temperature of at least 50C., 7 preferably at leas~ 80~Co A free radical polymeriza~ion 8 promoter such as azo isobutylnitrile, benzoyl peroxide, t-9 butyl hydroperoxide or di~t~butyl peroxide is uscd.
The oil~soluble reactiQn products of this inven-11 tion can be incorporated in lubricating oil compositions, 12 e.gO automotive crankcase lubricating oils, in concentra-13 tions within the range of about OoOl to 200 wt. %, prefer-14 ably 0~1 to 0.5 w~. %, of the total composi~ion. The lubricants t~which the poiymeric products o~ this invention 16 can be added include not only hydrocarbon oils derived from 17 petroleum, tar sand or shale but also include synthetic 9ils 18 of the hydrocarbon or polyester variety and mixtures thçreof.
19 The additive may be conveniently dispensed as a concentrate comprising 20~60 par~s by weight, preerred 21 about 50 parts by weight o the additive dissolved in from 22 40 to 80 parts by weight of a mineral lubricating oil with 23 or without other additives being present.
24 The copolymers of the invention can be esterified with saturated alipha~ic alcohols of up to 8 carbon atoms to 26 impro~e the pour point depressant acti~ity o~ the copolymer.
27 l~ese alcohols can be eitheP straight or branched chain and 28 include methanol, ethanol, propanol, butanol, pentanol, 29 hexanol, heptanol, octanol, 2~ethyl hexanol, etc.
. .
For purposes of this disclosure a l~olefin is a 31 hydrocarbon which had a double bond between the Cl and C2 32 carbons and may or may not have another substituent on the w 5 -~7Z~35 1 C2 carbon, e.g. l~hexene and 2~methyl l-pentene.
2 This invention will be further understood by ref-3 erence to the following examples, which include preferred 4 embodiments of ihe invention.
6 A copolymer of (C20~G24) lDolef-Lns and maleic an-7 hydride was prepare~ by mixing 108 g. of maleic anhydride, 8 320 g. of C20~C2~ l~olefins3 400 mlO of ethylene dichloride, 9 and 2.4 g of Lucidol 70 (70% benzoyl peroxide and 30 wt. %
water) in a liter r~sin pot which was fitted with an agi~
11 tator, condens~r, thermometer3 nitrogen sparging tube and 12 heating mant~e. The mixture was heated to 38C.3 sparged 13 slightly with nitrogen and then heated to 72Co where it was 14 maintained for 3 hours with agitationO Therea~ter 0.9 g. of Lucidol 70 was added and polymerization continued for an ad-16 ditional 18 hours by maintenance at 72~80C~
17 The polymer may be fr ed of raw materials by pre~
18 cipitation in cold isopropanol or by dialysis against a rub~
19 ber membrane for thr~e hours with toluene.
21 A copolymer of ~C20l~2~) ~ C6 l~olefins and maleic 22 acid anhydride was p~epared by the procedure of Example 1 23 except that 182 g~ maleic anhydride9 324 gO of C20-c24 1-24 olefins and 68 g. of hexene~l was used. The copolymer prod-uct was insoluble in ~il at room temperature.
27 A copolymer of (C20~C2~) ~ C8 l olefins and maleic 28 anhydride was prepared by the procedure of Example 2 except 2~ that 92 g. of octene-l was used Ln place o~ hexeneol.
. .
31 A copolymer of (C20-C24) ~ C10 l-olefins and mal~ic 32 anhydride was prep~red by the procedure o~ Example 2 except *Trade Mark ~72~35 1 that 115 g. of decene l was used in place of hexene-l.
3 The product of Example 1, i.e. thP copolymer of 4 C20 C24 l~olefins and maleic anhydride was fully esterified with 2~ethyl hexanol using p~toluene sulfonic acid as the 6 catalyst and azeotxoping of~ the water of esteri~ication `7 with toluene.
8 EXAMPI~ 6 ; . 9 The product o~ Example 2, i.e. the copolymer of (C20-C24) ~ C6 l olefins and maleic anhydride, was fully 11 esterified with 2~ethyl hexanol using the procedure of 12 Example 5.
13 The copolymers prepared în Examples 1-6 had the 14 following properties~
Product Example Yield % Mol.Wt.*Mn %C %H
16 1 6~ ~00 71.511.6 - 17 2 67 5~00 71o 710~ 9 l8 3 ~7-~ ~7~0 71.~10.6 19 ~ 3000 72.7 7.5 ,~ 20 5 21 6 68 7000 74.511.6 22 *number average molecular weight determined by vapor 23 phase osmometry on Mechrolab Vapor Phase Osmometer 24 Model 310A.
The various copolymers described above were admix i 26 ed at room temperature by stirring with a lubricating oil 27 and subjected to an ASTM test which demonstrates the copoly-28 mers o~ the invention be highly e~fective pour point depres-29 sants as is apparent from ~he following table.
*Trade Mark ,; ~ .
7Z53~
TABL;E
2 Pour De ressan~ Activit 3 Product of ~i~u~
4 Ex~mple~dditivetD-e D~e-~cd 0-1 1 0.2 -15 6 2 insolubla 0 7 3 0.2 o20 8 4 0.2 ~20 9 5 0,2 ~25 6 0.2 ~25 11 *ASTM Test D~97. The treated oil is a mineral lubricat-:. 12 ing oil having a pour point of 0F. and a viscosity 13@210F. o about 44. 0SUSO
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51556374A | 1974-10-17 | 1974-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072535A true CA1072535A (en) | 1980-02-26 |
Family
ID=24051850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA235,563A Expired CA1072535A (en) | 1974-10-17 | 1975-09-16 | Pour point depressant additive |
Country Status (3)
| Country | Link |
|---|---|
| CA (1) | CA1072535A (en) |
| FR (1) | FR2330702A1 (en) |
| GB (1) | GB1525114A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3046714A1 (en) * | 1979-12-13 | 1981-08-27 | Institut Français du Pétrole, 92502 Rueil-Malmaison, Hauts-de-Seine | TERPOLYMERS, THEIR PRODUCTION AND USE AS ADDITIVES FOR IMPROVING THE FLOW PROPERTIES OF VARIOUS PETROLEUM PRODUCTS |
| US4358573A (en) * | 1981-05-29 | 1982-11-09 | S. C. Johnson & Son, Inc. | Waxy maleic anhydride alpha olefin terpolymers |
| US4859752A (en) * | 1987-09-11 | 1989-08-22 | S. C. Johnson & Son, Inc. | Alkene/excess maleic anhydride polymer manufacture |
| TW291486B (en) * | 1992-12-17 | 1996-11-21 | Exxon Chemical Patents Inc | |
| US6100224A (en) * | 1997-10-01 | 2000-08-08 | Exxon Chemical Patents Inc | Copolymers of ethylene α-olefin macromers and dicarboxylic monomers and derivatives thereof, useful as additives in lubricating oils and in fuels |
| CA3188369A1 (en) * | 2020-09-14 | 2022-03-17 | Ecolab Usa Inc. | Cold flow additives for plastic-derived synthetic feedstock |
| CN114524889B (en) * | 2022-01-07 | 2024-01-09 | 国家能源集团宁夏煤业有限责任公司 | Method and system for synthesizing T803 pour point depressant from coal-based olefin and T803 pour point depressant |
-
1975
- 1975-09-16 CA CA235,563A patent/CA1072535A/en not_active Expired
- 1975-09-19 GB GB3853875A patent/GB1525114A/en not_active Expired
- 1975-10-16 FR FR7531686A patent/FR2330702A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2330702B1 (en) | 1980-04-30 |
| FR2330702A1 (en) | 1977-06-03 |
| GB1525114A (en) | 1978-09-20 |
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