# US 5,707,943 A · Mixtures of esterified carboxy-containing interpolymers and lubricants containing them

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- Number: US 5,707,943 A
- Document ID: US5707943A
- Status: Granted
- Kind: A
- Application number: 08/767,399
- Filed: 1996-12-16
- Granted: 1998-01-13
- Earliest claimed: 1996-12-16
- Assignees: The Lubrizol Corporation
- Inventors: Michael J. Covitch
- Web page: https://patentgrep.com/patent/US5707943A

## CPC

- C10M 145/16: polycarboxylic
- C10M 129/95: Esters
- C10M 133/12: having amino groups bound to a carbon atom of a six-membered aromatic ring
- C10M 133/56: Amides; Imides
- C10M 135/04: Hydrocarbons
- C10M 137/10: Thio derivatives
- C10M 143/04: containing propene
- C10M 145/14: Acrylate; Methacrylate
- C10M 149/06: containing monomers having an unsaturated radical bound to an amido or imido group
- C10M 149/10: containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
- C10M 159/20: Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M 159/24: containing sulfonic radicals
- C10M 167/00: Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
- C10M 2205/00: Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M 2205/024: Propene
- C10M 2207/123: polycarboxylic
- C10M 2207/129: having hydrocarbon chains of thirty or more carbon atoms
- C10M 2207/22: Acids obtained from polymerised unsaturated acids
- C10M 2207/26: Overbased carboxylic acid salts
- C10M 2207/34: Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
- C10M 2209/084: Acrylate; Methacrylate
- C10M 2209/086: polycarboxylic, e.g. maleic acid
- C10M 2215/04: having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 2215/06: having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M 2215/064: Di- and triaryl amines
- C10M 2215/065: Phenyl-Naphthyl amines
- C10M 2215/066: Arylene diamines
- C10M 2215/067: Polyaryl amine alkanes
- C10M 2215/068: having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
- C10M 2215/086: Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2215/26: Amines
- C10M 2215/28: Amides; Imides
- C10M 2217/024: containing monomers having an unsaturated radical bound to an amido or imido group
- C10M 2217/028: containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
- C10M 2217/046: Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
- C10M 2217/06: Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
- C10M 2219/022: of hydrocarbons, e.g. olefines
- C10M 2219/046: Overbased sulfonic acid salts
- C10M 2223/045: Metal containing thio derivatives
- C10M 2223/047: Thioderivatives not containing metallic elements
- C10N 2010/04: Groups 2 or 12
- C10N 2070/02: {Concentrating of additives}
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

Mixtures of esterified carboxy-containing interpolymers and additive concentrates and lubricating oil compositions containing same. Residual acidity of the esterified interpolymers may be neutralized by reaction with an amine.

## Claims

### Claim 1

A composition comprising a mixture of esterified carboxy-containing interpolymers, said interpolymers having a reduced specific viscosity (RSV) of from about 0.05 to about 2 and being derived from at least two monomers comprising (i) an aliphatic olefin containing from 2 to about 30 carbon atoms or a vinyl aromatic monomer and (ii) an alpha, beta-unsaturated acylating agent, said mixture being characterized by the presence therein of at least two members of the group consisting of
(I) an ester which within its polymeric structure consists essentially of
(A) pendant carboxylic ester groups which are derived from the carboxy groups of said interpolymers, said carboxylic ester groups containing at least 8 carbon atoms;
(II) an ester which is a mixed ester of said carboxy-containing interpolymers and being characterized by the presence within its polymeric structure of at least one of each of two ester groups:
(B) relatively high molecular weight pendant carboxylic ester groups containing at least eight aliphatic carbon atoms, and
(C) relatively low molecular weight pendant carboxylic ester groups containing no more than seven aliphatic carbon atoms, wherein the molar ratio of (B):(C): is (70-95):(5-30);
(III) an ester which is a nitrogen-containing ester, and which within its polymeric structure consists essentially of
(A) pendant carboxylic ester groups which are derived from the carboxy groups of said interpolymers, said carboxylic ester groups containing at least 8 carbon atoms, and
(D) pendant carbonyl-amino groups derived from amino compounds having an average of from 1 to about 1.1 primary or secondary amino group, wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups of said interpolymer neutralized to provide (D) is in the range of from about 85:15 to about 99:1; and
(IV) an ester which is a nitrogen-containing ester, which is a mixed ester of said carboxy-containing interpolymers and being characterized by the presence within its polymeric structure of at least one of each of three groups:
(B) relatively high molecular weight pendant carboxylic ester groups containing at least eight aliphatic carbon atoms,
(C) relatively low molecular weight pendant carboxylic ester groups containing no more than seven aliphatic carbon atoms, and
(E) pendant carbonyl-amino groups derived from amino compounds having an average of from 1 to about 1.1 primary or secondary amino group,
wherein the molar ratio of(B):(C):(E) is (60-94):(5-30):(1-15);
and wherein the at least two members include at least one ester having the carboxylic ester group (A) and at least one ester having the carboxylic ester groups (B) and (C).

### Claim 2 (depends on 1)

The composition of claim 1 wherein the interpolymers have RSV ranging from about 0.08 to about 1.2.

### Claim 3 (depends on 2)

The composition according to claim 2 wherein the RSV range from 0.08 to about 0.9.

### Claim 4 (depends on 1)

The composition of claim 1 wherein the aliphatic olefin is an alpha olefin.

### Claim 5 (depends on 1)

The composition of claim 1 wherein the vinyl aromatic monomer is styrene or a substituted styrene.

### Claim 6 (depends on 1)

The composition of claim 1 wherein the alpha,beta-unsaturated acylating agent is an aliphatic carboxylic acid, anhydride, or esters thereof.

### Claim 7 (depends on 1)

The composition of claim 1 wherein the alpha, beta-unsaturated acid, anhydride or ester is at least one member selected from the group consisting of maleic acid or anhydride, itaconic acid or anhydride, fumaric acid, .alpha.-methylene glutaric acid, acrylic acid, methacrylic acid or an ester of any of these.

### Claim 8 (depends on 1)

The composition of claim 1 wherein the ester groups of (A) have from 8 to about 30 carbon atoms.

### Claim 9 (depends on 8)

The composition of claim 8 wherein the ester groups of (A) are selected from the group of ester groups having from 12 to 18 carbon atoms or mixtures of ester groups having from 12 to 18 carbon atoms.

### Claim 10 (depends on 1)

The composition of claim 1 wherein the relatively high molecular weight carboxylic ester groups of (B) have from 8 to about 30 carbon atoms and the relatively low molecular weight carboxylic ester groups of (C) have from 3 to 5 carbon atoms.

### Claim 11 (depends on 1)

The composition of claim 1 wherein each interpolymer is derived from styrene and maleic anhydride.

### Claim 12 (depends on 11)

The composition of claim 11 wherein each interpolymer is further derived from a methacrylic acid ester.

### Claim 13 (depends on 1)

The composition of claim 1 wherein the mole ratios of (i):(ii) range from about 1:2 to about 3:1.

### Claim 14 (depends on 1)

The composition of claim 1 wherein at least one amino compound is a polyamino compound.

### Claim 15 (depends on 14)

The composition of claim 14 wherein the polyamino compound has one primary or secondary amino group and at least one tertiary amino group.

### Claim 16 (depends on 1)

The composition of claim 1 wherein the mixture of esters comprises at least none of esters (I) and (II) and at least one of nitrogen-containing esters (III) and (IV).

### Claim 17 (depends on 1)

The composition of claim 1 wherein the mixture of esters comprises (I) and (II).

### Claim 18 (depends on 1)

The composition of claim 1 wherein the mixture of esters comprises nitrogen-containing esters (III) and (IV).

### Claim 19 (depends on 1)

The composition of claim 1 comprising from about 1 to about 99% by weight of esters having carboxylic ester group (A) and from about 99 to about 1% by weight of esters having carboxylic ester groups (B) and (C).

### Claim 20 (depends on 19)

The composition of claim 19 comprising from about 1 to about 99% by weight of (I) and from about 99% to about 1% by weight of (II).

### Claim 21 (depends on 19)

The composition of claim 19 comprising from about 1 to about 99% by weight of (III) and from about 99% to about 1% by weight of (IV).

### Claim 22 (depends on 1)

An additive concentrate composition comprising a substantially inert normally liquid organic diluent and from about 0.01 to about 90% by weight of the composition of claim 1.

### Claim 23 (depends on 1)

A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of the composition of claim 1.

### Claim 24 (depends on 22)

A lubricating oil composition comprising a major mount of an oil of lubricating viscosity and a minor amount of the composition of claim 22.

### Claim 25 (depends on 1)

The additive concentrate of claim 1 further containing a viscosity improver, and optionally, at least one oxidation inhibiting agent.

### Claim 26

A composition useful as a pour point depressant for hydrocarbon based liquids, prepared by a process comprising mixing together two or more esterified carboxy-containing interpolymers having a reduced specific viscosity of from about 0.05 to about 2, said interpolymers being derived from at least two monomers comprising (i) an aliphatic olefin containing from 2 to about 30 carbon atoms or a vinyl aromatic monomer and (ii) an alpha, beta-unsaturated acylating agent, said mixture being characterized by the presence therein of at least two members of the group consisting of
(I) an ester which within its polymeric structure consists essentially of
(A) pendant carboxylic ester groups which are derived from the carboxy groups of said interpolymers, said carboxylic ester groups containing at least 8 carbon atoms;
(II) an ester which is a mixed ester of said carboxy-containing interpolymers and being characterized by the presence within its polymeric structure of at least one of each of two ester groups:
(B) relatively high molecular weight pendant carboxylic ester groups containing at least eight aliphatic carbon atoms, and
(C) relatively low molecular weight pendant carboxylic ester groups containing no more than seven aliphatic carbon atoms, wherein the molar ratio of (B):(C) is (70-95):(5-30);
(III) an ester which is a nitrogen-containing ester, and which within its polymeric structure consists essentially of
(A) pendant carboxylic ester groups which are derived from the carboxy groups of said interpolymers, said carboxylic ester groups containing at least 8 carbon atoms, and
(D) pendant carbonyl-amino groups derived from amino compounds having an average of from 1 to about 1.1 primary or secondary amino group, wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups of said interpolymer neutralized to provide (D) is in the range of from about 85:15 to about 99:1; and
(IV) an ester which is a nitrogen-containing ester, which is mixed ester of said carboxy-containing interpolymers and being characterized by the presence within its polymeric structure of at least one of each of three groups:
(B) relatively high molecular weight pendant carboxylic ester groups containing at least eight aliphatic carbon atoms,
(C) relatively low molecular weight pendant carboxylic ester groups containing no more than seven aliphatic carbon atoms, and
(E) pendant carbonyl-amino groups derived from amino compounds having an average of from 1 to about 1.1 primary or secondary amino group, wherein the molar ratio of(B):(C):(E) is (60-94):(5-30):(1-15),
and wherein the at least two members include at least one ester having the carboxylic ester group (A) and at least one ester having the carboxylic ester groups (B) and (C).