Heterocyclic amine terminated, lactone modified, aminated viscosity modifiers of improved dispersancy
First Claim
1. A process for preparing polymeric dispersant additives for lubricating oils and hydrocarbon fuels, which comprises:
- reacting a C5-C9 lactone at a temperature of from about 50°
to about 200°
C. with an aminoalkyl derivative having from 2 to about 60 total carbon atoms and from 2 to about 12 nitrogen atoms, said aminoalkyl derivative being terminated on one end thereof by a primary or secondary amino group and being terminated on the other end thereof with a tertiary amino-containing hetero-cyclic ring, to effect ring opening polymerization of said lactone and to form an adduct which contains a heterocyclic ring on one end and a hydroxyl group on the other end; and
reacting said adduct at a temperature of from about 100°
to about 250°
C. for a period of from about 10 minutes to about 30 hours with a copolymer of ethylene and at least one C3 to C28 alpha-olefin, which copolymer has been grafted with an ethylenically unsaturated carboxylic acid material prior to being reacted with said adduct, to form an ester- and amide-containing polymeric dispersant reaction product having a degree of polymerization of said lactone of from about 0.2 to about 100 said ethylenically unsaturated dicarboxylic acid material being selected from the group consisting of organic compounds which contain at least two carboxylic acid groups or anhydride groups or a polar group which is convertible into said carboxylic acid groups by oxidation or hydrolysis.
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Accused Products
Abstract
Polymer C5 -C9 derivatives are made by reacting a C5 -C9 lactone with an aminoalkyl derivative, e.g., N-(3-aminopropyl) morpholine, to form an adduct having a hydroxyl group on one end thereof and a tertiary amino nitrogen-containing heterocyclic ring group on the other end thereof, and then reacting the adduct with an ethylene-C3 to C28 alpha-olefin copolymer or terpolymer which has from about 0.2 to about 5 wt. % of ethylenically unsaturated carboxylic acid units grafted thereto, e.g., maleic anhydride ethylene-propylene copolymer. The resulting polymeric C5 -C9 lactone derivatives are usful per se as multifunctional oil soluble additives for fuel and lubricating oil compositions, including concentrates containing the additives.
71 Citations
43 Claims
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1. A process for preparing polymeric dispersant additives for lubricating oils and hydrocarbon fuels, which comprises:
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reacting a C5-C9 lactone at a temperature of from about 50°
to about 200°
C. with an aminoalkyl derivative having from 2 to about 60 total carbon atoms and from 2 to about 12 nitrogen atoms, said aminoalkyl derivative being terminated on one end thereof by a primary or secondary amino group and being terminated on the other end thereof with a tertiary amino-containing hetero-cyclic ring, to effect ring opening polymerization of said lactone and to form an adduct which contains a heterocyclic ring on one end and a hydroxyl group on the other end; andreacting said adduct at a temperature of from about 100°
to about 250°
C. for a period of from about 10 minutes to about 30 hours with a copolymer of ethylene and at least one C3 to C28 alpha-olefin, which copolymer has been grafted with an ethylenically unsaturated carboxylic acid material prior to being reacted with said adduct, to form an ester- and amide-containing polymeric dispersant reaction product having a degree of polymerization of said lactone of from about 0.2 to about 100 said ethylenically unsaturated dicarboxylic acid material being selected from the group consisting of organic compounds which contain at least two carboxylic acid groups or anhydride groups or a polar group which is convertible into said carboxylic acid groups by oxidation or hydrolysis. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)
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17. The process of forming a polymeric dispersant additive for lubricating oils and hydrocarbon fuels, which comprises the steps of:
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(a) forming a copolymer of ethylene and at least one C3 -C28 alpha-olefin and, optionally, a non-conjugated diolefin, wherein said copolymer comprises from 2 to about 98 wt. % of ethylene moieties, from 2 to about 98 wt. % alpha-olefin moieties, and up to about 20 mole % of non-conjugated diolefin moieties; (b) grafting onto the copolymer formed in step (a) from about 0.2 wt. % to about 5 wt. % of an ethylenically unsaturated carboxylic acid material, said acid material being selected from the group consisting of organic compounds which contain at least two carboxylic acid groups or anhydride groups or a polar group which is convertible into said carboxylic acid groups by oxidation or hydrolysis; (c) reacting a C5 -C9 lactone with an aminoalkyl derivative having from 2 to about 60 total carbon atoms and from 2 to about 12 nitrogen atoms at a temperature of from about 50 to about 200°
C. to effect ring opening polymerization of said lactone and to form an adduct which is terminated at one end thereof with a hydroxyl group and at the other end with a nitrogen-containing heterocyclic ring, said aminoalkyl derivative being terminated at one end thereof with a primary or secondary amino group and at the other end thereof with a nitrogen-containing heterocyclic ring, and said adduct having a degree of polymerization of said lactone of from about 0.2 to about 100; and(d) reacting the adduct formed in step (c) with the grafted ethylene-alpha-olefin copolymer formed in step (b) at a temperature of from about 100°
to about 250°
C. to form a polymeric dispersant additive exhibiting improved varnish performance, the amount of said adduct being reacted in step (d) being from about 0.01 to about 10 moles of adduct per mole of grafted ethylene-alpha-olefin copolymer. - View Dependent Claims (18)
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19. The process of forming a polymeric dispersant additive for lubricating oils and hydrocarbon fuels, which comprises the steps of:
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(a) reacting a C5 -C9 lactone with an aminoalkyl derivative having from 2 to about 60 total carbon atoms and from 2 to about 12 nitrogen atoms at a temperature of from about 50°
to about 200°
C. to effect ring opening polymerization of said lactone and to form an adduct which is terminated at one end thereof with a hydroxyl group and at the other end with a nitrogen-containing heterocyclic ring, said aminoalkyl derivative being terminated at one end thereof with a primary or secondary amino group and at the other end thereof with a nitrogen-containing heterocyclic ring;(b) forming a copolymer of ethylene and at least one C3 -C28 alpha-olefin and, optionally, a non-conjugated diolefin, wherein said copolymer comprises from 2 to about 98 wt. % of ethylene moieties, from 2 to about 98 wt. % alpha-olefin moieties, and up to about 20 mole % of non-conjugated diolefin moieties; (c) grafting onto the copolymer formed in step (b) from about 0.2 wt. % to about 5 wt. % of an ethylenically unsaturated carboxylic acid material, said material being selected from the group consisting of organic compounds which contain at least two carboxylic acid groups or anhydride groups or a polar group which is convertible into said carboxylic acid groups by oxidation or hydrolysis; and (d) reacting the adduct formed in step (a) with the grafted ethylene-alpha-olefin copolymer formed in step (c) at a temperature of from about 100°
to about 250°
C. to form a polymeric dispersant additive exhibiting improved varnish performance, the amount of said adduct being reacted in step (d) being from about 0.01 to about 10 moles of adduct per mole of grafted ethylene-alpha-olefin copolymer, said polymeric dispersant additive having a degree of polymerization of said lactone of from about 0.2 to about 100. - View Dependent Claims (20)
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21. A polymeric lactone derivative useful as an oil additive having improved dispersancy and formed by reacting together at a temperature of from about 100°
- to about 250°
C.;(a) an adduct of a C5 -C9 lactone and an aminoalkyl derivative, and (b) a copolymer of ethylene, at least one C3 -C28 alpha-olefin, and, optionally, a non-conjugated diolefin, said aminoalkyl derivative having from 2 to about 60 total carbon atoms and from 2 to about 12 nitrogen atoms and being terminated at one end thereof with a primary or secondary amino group and at the other end thereof with a tertiary amino-containing heterocyclic ring, said copolymer of ethylene having moieties derived from an ethylenically unsaturated carboxylic acid material grafted thereto, said acid material being selected from the group consisting of organic compounds which contain at least two carboxylic acid groups or anhydride groups or a polar group which is convertible into said carboxylic acid groups by oxidation or hydrolysis, and said adduct of said C5 -C9 lactone and said aminoalkyl derivative being formed by reacting together said C5 -C9 lactone with said aminoalkyl derivative at a temperature of from about 50°
to about 200°
C., said adduct being terminated at one end thereof with a hydroxyl group and at the other end with said tertiary amino-containing heterocyclic ring, and said polymeric lactone derivative having a degree of polymerization of said lactone of from about 0.2 to about 100. - View Dependent Claims (22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35)
- to about 250°
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36. An oil soluble dispersant useful as an oil additive, comprising the product of a reaction mixture comprising:
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(I) an ethylene-C3 to C28 alpha-olefin copolymer or an ethylene-C3 to C28 alpha-olefin-non-conjugated diolefin terpolymer, wherein said copolymer or terpolymer contains from about 2.0 to about 5 wt. % of ethylenically unsaturated carboxylic acid material-derived units grafted thereto, said unsaturated carboxylic acid material being selected from the group consisting of organic compounds which contain at least two carboxylic acid groups or anhydride groups or a polar group which is convertible into said carboxylic acid groups by oxidation or hydrolysis, and (II) a C5 -C9 lactone adduct having a hydroxyl group on one end thereof and an N-heterocyclic ring on the other end thereof, wherein said adduct was formed by reacting at a temperature of from about 50°
to about 200°
C. (a) a C5 -C9 lactone with (b) an aminoalkyl derivative having a terminal primary or secondary amino group on one end thereof and said N-heterocyclic ring of the other end thereof, said adduct having a degree of polymerization of said lactone of from about 0.2 to about 100, and said aminoalkyl derivative having from 2 to about 60 total carbon atoms and from 2 to about 12 nitrogen atoms,wherein said product of said reaction mixture is prepared by reacting components (I) and (II) at a temperature of about 100°
to about 250°
C. - View Dependent Claims (37, 38, 39)
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40. An oil soluble reaction product useful as an oil additive having varnish performance of:
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(a) polymer consisting essentially of an ethylene-C3 to C28 alpha-olefin backbone or an ethlyene-C3 to C8 alpha-olefin-non-conjugated diolefin backbone, said backbone having a number average molecular weight of about 700 to about 500,000 and having grafted thereto from about 0.2 to about 5 wt. % of ethylenically unsaturated carboxylic acid material units, based on the weight of the grafted polymer, said carboxylic acid material being selected from the group consisting of organic compounds which contain at least two carboxylic acid groups or anhydride groups or a polar group which is convertible into said carboxylic acid groups by oxidation or hydrolysis, (b) an aminoalkyl derivative selected from the group consisting of aminoalkyl morpholines and heterocyclic nitrogen compounds of the general formula;
##STR23## wherein G is hydrogen or an omega-aminoalkylene radical of from 1 to 3 carbon atoms, and p is a number of from 1 to 4, and,(c) a C5 -C9 lactone, wherein (b) is first reacted with (c) at a temperature of from about 50°
to about 200°
C. to form an adduct which is terminated on one end thereof with a hydroxyl group and on the other end thereof with a nitrogen-containing heterocyclic ring, wherein said adduct is then reacted with (a) at a temperature of from about 100°
to about 250°
C. to form said oil soluble reaction product, and wherein the degree of polymerization of said C5 -C9 lactone in said adduct is from about 0.2 to about 100. - View Dependent Claims (41, 42, 43)
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Specification