Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same
First Claim
1. A C5 -C9 lactone derived material useful as an oil additive and formed by (1) simultaneously reacting at a temperature of from about 100 to about 220°
- C. for a period of from about 1 to about 10 hours a hydrocarbyl substituted C4 -C10 dicarboxylic acid producing material with a C5 -C9 lactone and a member selected from the group consisting of (a) a polyamine having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (b) an aliphatic polyhydric alcohol containing up to about 100 carbon atoms and from about 2 to about 10 hydroxyl groups, (c) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, or (d) mixtures thereof, and (2) post-treating the reaction product formed in step (1) with a boron reactant, said hydrocarbyl substituted acid producing material being formed by reacting an olefin polymer of a C2 -C10 monoolefin having a number average molecular weight of about 300 to about 10,000 and a C4 -C10 monounsaturated dicarboxylic acid material selected from the group consisting of acids, esters and anhydrides and containing an average of about 0.7 to about 2.0 molar equivalents of dicarboxylic acid producing moieties per molar equivalent of said olefin polymer, said C5 -C9 lactone having undergone ring opening polymerization such that the degree of polymerization of said C5 -C9 lactone in the final C5 -C9 lactone derived material is from about 0.2 to about 100.
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Abstract
C5 -C9 lactone derived materials are made by simultaneously reacting (a) a C5 -C9 lactone with (b) a polyamine, a polyol or an amino alcohol and (c) a hydrocarbyl substituted C4 -C10 monounsaturated dicarboxylic acid producing material, e.g., a polyisobutenyl succinimide, which preferably was made by reacting a polymer of a C2 to C10 monoolefin, preferably polyisobutylene, having a molecular weight of about 300 to 10,000 with a C4 to C10 monounsaturated acid, anhydride or ester, preferably maleic anhydride, such that there are 0.7 to 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer used in the reaction mixture. The resulting lactone derived materials, which may be post-treated, for example, with a boron compound, are useful, per se, as oil soluble dispersant additives, and are useful in fuel and lubricating oil compositions including concentrates containing the additives.
104 Citations
90 Claims
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1. A C5 -C9 lactone derived material useful as an oil additive and formed by (1) simultaneously reacting at a temperature of from about 100 to about 220°
- C. for a period of from about 1 to about 10 hours a hydrocarbyl substituted C4 -C10 dicarboxylic acid producing material with a C5 -C9 lactone and a member selected from the group consisting of (a) a polyamine having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (b) an aliphatic polyhydric alcohol containing up to about 100 carbon atoms and from about 2 to about 10 hydroxyl groups, (c) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, or (d) mixtures thereof, and (2) post-treating the reaction product formed in step (1) with a boron reactant, said hydrocarbyl substituted acid producing material being formed by reacting an olefin polymer of a C2 -C10 monoolefin having a number average molecular weight of about 300 to about 10,000 and a C4 -C10 monounsaturated dicarboxylic acid material selected from the group consisting of acids, esters and anhydrides and containing an average of about 0.7 to about 2.0 molar equivalents of dicarboxylic acid producing moieties per molar equivalent of said olefin polymer, said C5 -C9 lactone having undergone ring opening polymerization such that the degree of polymerization of said C5 -C9 lactone in the final C5 -C9 lactone derived material is from about 0.2 to about 100.
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 64, 65, 66, 67)
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29. An oleaginous composition comprising (I) a lubricating oil and (II) a C5 -C9 lactone derived material which has been prepared by first simultaneously reacting at a temperature of from about 100°
- to about 220°
C. for a period of from about 1 to about 20 hours (i) a C5 -C9 lactone, with (ii) a member selected from the group consisting of (a) a polyamine having from about 2 to about 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (b) an aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and (c) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to 15 hydroxyl groups, and (d) mixtures of (a), (b) and (c), and with (iii) a hydrocarbyl substituted C4 -C10 dicarboxylic acid producing material, and then post-treating the product obtained by reacting (i), (ii) and (iii) with a boron reactant;
said hydrocarbyl substituted C4 -C10 dicarboxylic acid producing material being formed by reacting an olefin polymer of a C2 -C10 monoolefin having a number average molecular weight of from about 300 to about 10,000 with a C4 -C10 monounsaturated dicarboxylic acid material and containing an average of from about 0.7 to about 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer, said C5 -C9 lactone having undergone ring opening polymerization such that the degree of polymerization of said lactone in said final lactone derived material is from about 0.2 to about 100. - View Dependent Claims (30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45)
- to about 220°
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57. An oil soluble dispersant useful as an oil additive, comprising the product of a reaction mixture comprising:
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(i) a hydrocarbyl substituted C4 -C10 monounsaturated dicarboxylic acid producing material formed by reacting olefin polymer of C2 to C10 monoolefin having a number average molecular weight of about 300 to 10,000 and a C4 to C10 monounsaturated acid material, wherein said hydrocarbyl substituted dicarboxylic acid producing material contains an average of from about 0.7 to about 2.0 molar equivalents of dicarboxylic acid producing moieties per molar equivalent of said olefin polymer; (ii) a C5 -C9 lactone; and (iii) at least one member selected from the group consisting of (a) a polyamine having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (b) an aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and (c) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, wherein said reaction mixture has been heated at a temperature of from about 100 to about 220°
C., for a period of from about 1 to about 10 hours, wherein the product of (i), (ii) and (iii) has been post-treated with a boron reactant, and wherein the degree of polymerization of said C5 -C9 lactone in the product of (i), (ii) and (iii) is from about 0.5 to about 20. - View Dependent Claims (58, 59, 60, 61, 62, 63, 68, 69, 70, 71)
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72. An oil soluble reaction product useful as an oil additive comprising:
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(a) polymer consisting essentially of C2 to C10 monoolefin, said polymer being of 300 to 10,000 number average molecular weight and being substituted with succinic moieties selected from the group consisting of acid, anhydride and ester groups, wherein there are from about 0.7 to about 2.0 molar proportions of succinic moieties per molar proportion of said polymer, (b) amine containing 2 to 60 carbon atoms and 2 to 12 nitrogen groups, (c) C5 -C9 lactone, wherein (a) (b) and (c) are reacted simultaneously at a temperature of from about 100 to about 220°
C. for a period of from about 1 to about 10 hours, wherein there are about 0.2 to 100 molar proportions of (c) per molar proportion of said oil soluble reaction product, and,(d) boron, wherein said boron has been introduced into said reaction product subsequent to the simultaneous reaction of (a), (b) and (c). - View Dependent Claims (73, 74, 77)
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75. An oil soluble reaction product useful as an oil additive having improved dispersancy and viscosity characteristics of:
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(a) polymer consisting essentially of C2 to C10 monoolefin said polymer being of 300 to 10,000 number average molecular weight and being substituted with succinic moieties selected from the group consisting of acid, anhydride and ester groups wherein there are from about 0.7 to about 2.0 molar proportions of succinic moieties per molar proportion of said polymer, (b) aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from 2 to about 10 hydroxyl groups, (c) C5 -C9 lactone, wherein (a) (b) (c) are reacted simultaneously at a temperature of from about 100 to about 220°
C. for a period of from about 1 to about 10 hours and wherein there are about 0.2 to 100 molar proportions of (c) per molar proportion of said reaction product, and,(d) boron, wherein said boron has been introduced into said reaction product subsequent to the simultaneous reaction of (a), (b) and (c). - View Dependent Claims (76)
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78. An oil soluble reaction product useful as an oil additive which comprises:
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(a) polymer consisting essentially of C2 to C10 monoolefin said polymer being of 300 to 10,000 number average molecular weight and being substituted with succinic moieties selected from the group consisting of acid, anhydride and ester groups wherein there are from about 0.7 to about 2.0 molar proportions of succinic moieties per molar proportion of said polymer, (b) amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, (c) C5 -C9 lactone, wherein (a) (b) and (c) are reacted simultaneously at a temperature of from about 100 to about 220°
C. for a period of from about 1 to about 10 hours, and wherein there are about 0.2 to 100 molar proportions of (c) per molar proportion of said oil soluble reaction product, and,(d) boron, wherein said boron has been introduced into said reaction product subsequent to the simultaneous reaction of (a), (b) and (c). - View Dependent Claims (79, 80)
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81. A lubricating crankcase motor oil composition for automotive vehicles and trucks comprising a major amount of lubricating oil;
- from about 0.01 to 15 wt. % of a dispersant formed by first simultaneously reacting at a temperature of from about 100°
to about 220°
C. for a period of from about 1 to about 10 hours (a) polyolefin substituted with a succinic acid or anhydride moieties with (b) a C5 -C9 lactone and (c) at least one member selected from the group consisting of (i) polyamines having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (ii), aliphatic polyhydric alcohols containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and (iii) amino alcohols containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, and then reacting the product of (a), (b) and (c) with a boron reactant, wherein said substituted succinic acid or anhydride has from about 0.7 to about 2.0 molar proportions of succinic moieties per molar proportion of polyolefin, wherein said polyolefin is a polymer of C2 to C10 monoolefin having a number average molecular weight of about 300 to 10,000 and wherein said dispersant has about 0.2 to 100 molar proportions of lactone moieties per molar proportion of polyolefin; and
about 3 to 25 wt. % of metal containing detergent additive. - View Dependent Claims (82, 83)
- from about 0.01 to 15 wt. % of a dispersant formed by first simultaneously reacting at a temperature of from about 100°
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84. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and 20 to 80 wt. % of a dispersant which is a C5 -C9 lactone derived material formed by first simultaneously reacting at a temperature of from about 100 to about 220°
- C. for a period of from about 1 to about 10 hours (a) 0.2 to 100 molar proportions of a C5 -C9 lactone per molar proportion of (b) at least one member selected from the group consisting of (i) polyamines having from about 2 to 60 total carbon atoms an from about 2 to about 12 nitrogen atoms, (ii) aliphatic polyhydric alcohols containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and (iii) amino alcohols containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, and (c) a hydrocarbyl substituted C4 -C10 monounsaturated dicarboxylic acid producing material which was formed by reacting an olefin polymer of a C2 to C10 monoolefin having a number average molecular weight of about 300 to 10,000 with a C4 to C10 monounsaturated acid material and containing an average of from about 0.7 to about 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer, and then reacting the product of (a), (b) and (c) with a boron reactant.
- View Dependent Claims (85, 86, 87)
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88. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and about 20 to about 80 wt. % of an oil soluble reaction product of (a) caprolactone (b) a hydrocarbyl substituted C4 to C10 monounsaturated dicarboxylic acid producing material, (c) at least one member selected from the group consisting of polyamines having from about 2 to 60 total carbon atoms and form about 2 to about 12 nitrogen atoms, aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and amino alcohols containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups,and (d) boron, wherein said reaction product has been prepared by first reacting (a), (b) and (c), at a temperature of from about 100°
- to about 220°
C. for a period of from 1 to about 10 hours, followed by reaction with (d), wherein said hydrocarbyl substituted material has been formed by reacting an olefin polymer of a C2 to C10 monoolefin having a number average molecule weight of about 500 to 3,000 and a C4 to C10 monounsaturated acid or anhydride and containing an average of from about 0.7 to about 2.0 molar equivalents of dicarboxylic acid producing moieties per molar equivalent of said olefin polymer, and wherein there are from 0.5 to 20 molar proportions of caprolactone per molar proportion of said olefin polymer present in said reaction product. - View Dependent Claims (89, 90)
- to about 220°
Specification