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US4604221A Expired / Lapsed US ⏱️ 0.0 years remaining

Nitrogen-containing esters and lubricants containing them

Assignee: Lubrizol Corp
•
Filing: 1985-04-03
•
Granted: 1986-08-05
•
Expires: 2005-04-03
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Abstract

Abstract A nitrogen-containing ester of a carboxy-containing interpolymer which is particularly useful as a pour point depressant is disclosed. The interpolymer has a reduced specific viscosity of from about 0.05 to about 1 and is derived from at least two monomers, one of said monomers being a low molecular weight aliphatic olefin or styrene and the other of said monomers being an alpha, beta-unsaturated aliphatic acid, anhydride or ester thereof. The nitrogen-containing ester is substantially free of titratable acidity and is characterized by the presence within its polymeric structure of at least one of each of the following groups which are derived from the carboxy groups of said interpolymer: (A) a carboxylic ester group, said carboxylic ester group having at least eight aliphatic carbon atoms in the ester radical, and (B) a carbonyl-polyamino group derived from a polyamino compound having one primary or secondary amino group and at least one monofunctional 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 (B) is in the range of about 85:15 to about 99:1. Lubricant compositions and additive concentrates comprising the foregoing nitrogen-containing ester as well as a process for making such ester are also disclosed.

Inventors

  • 👤 Charles P. Bryant
  • 👤 Harold M. Gerdes

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 21:48
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/30; C08F8/32

Claims Analysis

Total Claims: 54
Claim 1
Independent Claim 174 words
A nitrogen-containing ester consisting essentially of a carboxy-containing interpolymer, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1 and being derived from at least two monomers, one of said monomers being a low molecular weight aliphatic olefin or styrene and the other of said monomers being an alpha, beta-unsaturated aliphatic acid, anhydride or ester thereof, said nitrogen-containing ester being substantially free of tritratable acidity and being characterized by the presence within its polymeric structure of each of the following groups which are derived from the carboxy groups of said interpolymer: (A) a carboxylic ester group, said carboxylic ester group having at least eight aliphatic carbon atoms in the ester radical, and (B) a carbonyl-polyamino group derived from a polyamino compound having one primary or secondary amino group and at least one monofunctional heterocyclic 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 (B) is in the range of about 85:15 to about 99:1.
Claim 2
Dependent Claim 174 words
A nitrogen-containing ester consisting essentially of a carboxy-containing interpolymer, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1 and being derived from at least two monomers, one of said monomers being a low molecular weight aliphatic olefin or styrene and the other of said monomers being an alpha, beta-unsaturated aliphatic acid, anhydride or ester thereof, said nitrogen-containing ester being substantially free of tritratable acidity and being characterized by the presence within its polymeric structure of each of the following groups which are derived from the carboxy groups of said interpolymer: (A) a carboxylic ester group, said carboxylic ester group having at least eight aliphatic carbon atoms in the ester radical, and (B) a carbonyl-polyamino group derived from a polyamino compound having one primary or secondary amino group and at least one monofunctional heterocyclic 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 (B) is in the range of about 85:15 to about 99:1.
Claim 3
Dependent Claim 21 words
The nitrogen-containing ester of claim 1 wherein said reduced specific viscosity is in the range of about 0.2 to about 0.8.
Claim 4
Dependent Claim 21 words
The nitrogen-containing ester of claim 1 wherein said reduced specific viscosity is in the range of about 0.35 to about 0.8.
Claim 5
Dependent Claim 21 words
The nitrogen-containing ester of claim 1 wherein said reduced specific viscosity is in the range of about 0.35 to about 0.50.
Claim 6
Dependent Claim 21 words
The nitrogen-containing ester of claim 1 wherein said reduced specific viscosity is in the range of about 0.65 to about 0.75.
Claim 7
Dependent Claim 24 words
The nitrogen-containing ester of claim 1 wherein said low molecular weight aliphatic olefin is selected from the group consisting of ethylene, propylene or isobutene.
Claim 8
Dependent Claim 35 words
The nitrogen-containing ester of claim 1 wherein said alpha, beta-unsaturated aliphatic acid, anhydride or ester is selected from the group consisting of maleic acid or anhydride, itaconic acid or anhydride, or acrylic acid or ester.
Claim 9
Dependent Claim 21 words
The nitrogen-containing ester of claim 1 wherein each of the ester radicals of (A) have from 8 to 24 carbon atoms.
Claim 10
Dependent Claim 39 words
The nitrogen-containing ester of claim 1 wherein the ester radicals of (A) are selected from the group of ester radicals having from 12 to 18 carbon atoms or mixtures of ester radicals having from 12 to 18 carbon atoms.
Claim 11
Dependent Claim 36 words
The nitrogen-containing ester of claim 1 wherein the ester radicals of (A) are selected from the group of ester radicals having 14 or 15 carbon atoms or mixtures ofester radicals having 14 and 15 carbon atoms.
Claim 12
Dependent Claim 30 words
The nitrogen-containing ester of claim 1 wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups neutralized to provide (B) is about 95:5.
Claim 13
Dependent Claim 35 words
The nitrogen-containing ester of claim 1 wherein said interpolymer is a terpolymer of one molar proportion of styrene, one molar proportion of maleic anhydride, and less than about 0.3 molar proportion of a vinyl monomer.
Claim 14
Dependent Claim 13 words
The nitrogen-containing ester of claim 1 wherein said polyamino compound is N-aminoalkyl-substituted morpholine.
Claim 15
Dependent Claim 13 words
The nitrogen-containing ester of claim 1 wherein said polyamino compound is aminopropyl morpholine.
Claim 16
Dependent Claim 180 words
A nitrogen-containing ester consisting essentially of a carboxy-containing interpolymer having pour point depressant improving properties, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1 and being derived from at least two monomers, one of said monomers being a low molecular weight aliphatic olefin or styrene and the other of said monomers being an alpha, beta-unsaturated aliphatic acid, anhydride or ester thereof, said nitrogen-containing ester being substantially free of titratable acidity and being characterized by the presence within its polymeric structure of at least one of each of the following groups which are derived from the carboxy groups of said interpolymer: (A) a carboxylic ester group, said carboxylic ester group having at least eight aliphatic carbon atoms in the ester radical, and (B) a carbonyl-polyamino group derived from a polyamino compound having one primary or secondary amino group and at least one heterocyclic amino group, wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups neutralized to provide (B) is in the range of about 85:15 to about 99:1.
Claim 17
Dependent Claim 180 words
A nitrogen-containing ester consisting essentially of a carboxy-containing interpolymer having pour point depressant improving properties, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1 and being derived from at least two monomers, one of said monomers being a low molecular weight aliphatic olefin or styrene and the other of said monomers being an alpha, beta-unsaturated aliphatic acid, anhydride or ester thereof, said nitrogen-containing ester being substantially free of titratable acidity and being characterized by the presence within its polymeric structure of at least one of each of the following groups which are derived from the carboxy groups of said interpolymer: (A) a carboxylic ester group, said carboxylic ester group having at least eight aliphatic carbon atoms in the ester radical, and (B) a carbonyl-polyamino group derived from a polyamino compound having one primary or secondary amino group and at least one heterocyclic amino group, wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups neutralized to provide (B) is in the range of about 85:15 to about 99:1.
Claim 18
Dependent Claim 21 words
The nitrogen-containing ester of claim 15 wherein said reduced specific viscosity is in the range of about 0.2 to about 0.8.
Claim 19
Dependent Claim 21 words
The nitrogen-containing ester of claim 15 wherein said reduced specific viscosity is in the range of about 0.35 to about 0.8.
Claim 20
Dependent Claim 21 words
The nitrogen-containing ester of claim 15 wherein said reduced specific viscosity is in the range of about 0.35 to about 0.50.
Claim 21
Dependent Claim 21 words
The nitrogen-containing ester of claim 15 wherein said reduced specific viscosity is in the range of about 0.65 to about 0.75.
Claim 22
Dependent Claim 24 words
The nitrogen-containing ester of claim 15 wherein said low molecular weight aliphatic olefin is selected from the group consisting of ethylene, propylene or isobutene.
Claim 23
Dependent Claim 35 words
The nitrogen-containing ester of claim 15 wherein said alpha, beta-unsaturated aliphatic acid, anhydride or ester is selected from the group consisting of maleic acid or anhydride, itaconic acid or anhydride, or acrylic acid or ester.
Claim 24
Dependent Claim 39 words
The nitrogen-containing ester of claim 15 wherein the ester radicals of (A) are selected from the group of ester radicals having from 12 to 18 carbon atoms or mixtures of ester radicals having from 12 to 18 carbon atoms.
Claim 25
Dependent Claim 37 words
The nitrogen-containing ester of claim 15 wherein the ester radicals of (A) are selected from the groups of ester radicals having 14 or 15 carbon atoms or mixtures of ester radicals having 14 and 15 carbon atoms.
Claim 26
Dependent Claim 29 words
The nitrogen-containing ester of claim 15 wherein the ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups neutralized to provide (B) is about 95:5.
Claim 27
Dependent Claim 13 words
The nitrogen-containing ester of claim 15 wherein said polyamino compound is N-aminoalkyl-substituted morpholine.
Claim 28
Dependent Claim 13 words
The nitrogen-containing ester of claim 15 wherein said polyamino compound is aminopropyl morpholine.
Claim 29
Dependent Claim 152 words
A nitrogen-containing ester consisting essentially of a carboxy-containing interpolymer, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1 and being derived from at least two monomers, one of said monomers being styrene and the other of said monomers being maleic anhydride, said nitrogen-containing ester being substantially free of titratable acidity and being characterized by the presence within its polymeric structure of at least one of each of the following groups which are derived from the carboxy groups of said interpolymer: (A) a carboxylic ester group, said carboxylic ester group having from about 12 to about 18 aliphatic carbon atoms in the ester radical, and (B) a carbonyl-polyamino group derived from an N-aminoalkyl-substituted morpholine, wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups of said interpolymer neutralized to provide (B) is in the range of about 85:15 to about 99:1.
Claim 30
Dependent Claim 152 words
A nitrogen-containing ester consisting essentially of a carboxy-containing interpolymer, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1 and being derived from at least two monomers, one of said monomers being styrene and the other of said monomers being maleic anhydride, said nitrogen-containing ester being substantially free of titratable acidity and being characterized by the presence within its polymeric structure of at least one of each of the following groups which are derived from the carboxy groups of said interpolymer: (A) a carboxylic ester group, said carboxylic ester group having from about 12 to about 18 aliphatic carbon atoms in the ester radical, and (B) a carbonyl-polyamino group derived from an N-aminoalkyl-substituted morpholine, wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups of said interpolymer neutralized to provide (B) is in the range of about 85:15 to about 99:1.
Claim 31
Dependent Claim 21 words
The nitrogen-containing ester of claim 27 wherein said reduced specific viscosity is in the range of about 0.2 to about 0.8.
Claim 32
Dependent Claim 21 words
The nitrogen-containing ester of claim 27 wherein said reduced specific viscosity is in the range of about 0.35 to about 0.8.
Claim 33
Dependent Claim 21 words
The nitrogen-containing ester of claim 27 wherein said reduced specific viscosity is in the range of about 0.35 to about 0.50.
Claim 34
Dependent Claim 21 words
The nitrogen-containing ester of claim 27 wherein said reduced specific viscosity is in the range of about 0.65 to about 0.75.
Claim 35
Dependent Claim 20 words
The nitrogen-containing ester of claim 27 wherein each of the ester radicals of (A) have 14 or 15 carbon atoms.
Claim 36
Dependent Claim 30 words
The nitrogen-containing ester of claim 27 wherein the molar ratio of carboxy groups of said interpolymer esterified to provide (A) to carboxy groups neutralized to provide (B) is about 95:5.
Claim 37
Dependent Claim 35 words
The nitrogen-containing ester of claim 27 wherein said interpolymer is a terpolymer of one molar proportion of styrene, one molar proportion of maleic anhydride, and less than about 0.3 molar proportion of a vinyl monomer.
Claim 38
Dependent Claim 13 words
The nitrogen-containing ester of claim 27 wherein said N-aminoalkyl-substituted morpholine is aminopropyl morpholine.
Claim 39
Dependent Claim 27 words
A composition comprising a major proportion of a lubricating oil and at least from about 0.01% by weight of the nitrogen-containing ester of any of claims 1-35.
Claim 40
Dependent Claim 29 words
An additive concentrate comprising a substantially inert normally liquid organic diluent and from about 0.1 to about 80% by weight of the nitrogen-containing ester of any of claims 1-35.
Claim 41
Dependent Claim 131 words
A process for making a nitrogen-containing ester of a carboxy containing interpolymer consisting essentially of the steps of: providing an interpolymer derived from at least two monomers, one of said monomers being a low molecular weight aliphatic olefin or styrene and the other of said monomers being an alpha, beta-unsaturated aliphatic acid, anhydride or ester thereof, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1; partially esterifying said interpolymer with an alcohol having at least eight aliphatic carbon atoms to convert from about 85% to about 99% of the carboxy radicals of said interpolymer to ester radicals; and substantially neutralizing the remaining carboxy radicals of said interpolymer with a polyamino compound having one primary or secondary amino group and at least one monofunctional heterocyclic amino group.
Claim 42
Dependent Claim 131 words
A process for making a nitrogen-containing ester of a carboxy containing interpolymer consisting essentially of the steps of: providing an interpolymer derived from at least two monomers, one of said monomers being a low molecular weight aliphatic olefin or styrene and the other of said monomers being an alpha, beta-unsaturated aliphatic acid, anhydride or ester thereof, said interpolymer having a reduced specific viscosity of from about 0.05 to about 1; partially esterifying said interpolymer with an alcohol having at least eight aliphatic carbon atoms to convert from about 85% to about 99% of the carboxy radicals of said interpolymer to ester radicals; and substantially neutralizing the remaining carboxy radicals of said interpolymer with a polyamino compound having one primary or secondary amino group and at least one monofunctional heterocyclic amino group.
Claim 43
Dependent Claim 17 words
The process of claim 38 wherein said alcohol has from about 8 to about 24 carbon atoms.
Claim 44
Dependent Claim 20 words
The process of claim 38 wherein about 95% of the carboxy radicals of said interpolymer are esterified with said alcohol.
Claim 45
Dependent Claim 20 words
The process of claim 38 wherein said reduced specific viscosity is in the range of about 0.35 to about 0.8.
Claim 46
Dependent Claim 20 words
The process of claim 38 wherein said reduced specific viscosity is in the range of about 0.2 to about 0.8.
Claim 47
Dependent Claim 23 words
The process of claim 38 wherein said low molecular weight aliphatic olefin is selected from the group consisting of ethylene, propylene or isobutene.
Claim 48
Dependent Claim 34 words
The process of claim 38 wherein said alpha, beta-unsaturated aliphatic acid, anhydride or ester is selected from the group consisting of maleic acid or anhydride, itaconic acid or anhydride, or acrylic acid or ester.
Claim 49
Dependent Claim 15 words
The process of claim 38 wherein said alcohol has about 14 or 15 carbon atoms.
Claim 50
Dependent Claim 20 words
The process of claim 38 wherein said alcohol is a mixture of alcohols having from 12 to 18 carbon atoms.
Claim 51
Dependent Claim 19 words
The process of claim 38 wherein said alcohol is a mixture of alcohols having 14 and 15 carbon atoms.
Claim 52
Dependent Claim 12 words
The process of claim 38 wherein said polyamino compound is N-aminoalkyl-substituted morpholine.
Claim 53
Dependent Claim 12 words
The process of claim 38 wherein said polyamino compound is aminopropyl morpholine.
Claim 54
Dependent Claim 10 words
The product of the process of any of claims 38-49.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-08-04 1990-02-03 1990-08-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-08-04 1994-02-03 1994-08-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-08-04 1998-02-03 1998-08-05 $7700.00 Window Closed / Lapsed

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