GB2035295A - Novel iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof - Google Patents
Novel iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof Download PDFInfo
- Publication number
- GB2035295A GB2035295A GB7840180A GB7840180A GB2035295A GB 2035295 A GB2035295 A GB 2035295A GB 7840180 A GB7840180 A GB 7840180A GB 7840180 A GB7840180 A GB 7840180A GB 2035295 A GB2035295 A GB 2035295A
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- carbon atoms
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
- C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/22—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms containing a carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/086—Imides
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
Abstract
Novel iminodiimides of 3,3',4,4',- benzophenonetetracarboxylic dianhydride having the general formula: <IMAGE> wherein R is hydrogen, (C1-C36)alkyl, aryl aralkyl or alkaryl having from 6 to 36 carbon atoms are useful as pour depressants and as UV stabilizers when incorporated into lubricant compositions.
Description
SPECIFICATION
Novel iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof
This invention relates to novel iminodiimides of 3,3',4,4'-benzophenonetetracarboxylic dianhydride and to their use as pour depressants and/or UV stabilizers in lubricant compositions.
This invention provides a compound having the following general structure:
where R is H, alkyl having from 1 to 36 carbon atoms, aryl, aralkyl or alkaryl having from 6 to about 36 carbon atoms.
This invention further provides a composition comprising a major amount of an appropriate organic medium and a minor amount effective to impart pour depressant properties and ultra-violet stabilization characteristics thereto of a compound having the following general structure:
where R is H, alkyl having from 1 to about 36 carbon atoms, aryl, aralkyl or alkaryl having from 6 to about 36 carbon atoms.
A primary amine is reacted with benzophenonetetracarboxylic dianhydride (BTDA) under appropriate conditions to produce the novel compounds of this invention. The general structural formula of these compounds is as shown below.
where R preferably is H or an alkyl group, branched or straight, having from 1 to about 36 carbon atoms. R may also be aryl, alkaryl or aralkyl having from 6 to about 36 carbon atoms. R preferably contains 10 to 26 carbon atoms. The reaction is generally carried out at atmospheric pressure. However, pressures of up to about 200 psig and temperatures from 200 to about 400 C may be used if so desired. Preferred reaction conditions are atmospheric pressure and 230-250 C. Further, molar ratios of the amine to the benzophenonetetracarboxylic dianhydride are from about 3 to 3.5 moles of amine to 1 mole of BDTA. Preferred molar ratio is 3 moles of amine to 1 mole of BTDA.
Any primary amine having the following general structure can be used in preparing the novel class of iminodiimides disclosed herein:
H
I
R-N-H where R is alkyl, aryl, alkaryl or aralkyl or any combination thereof having from 1 to about 36 carbon atoms.
Some examples thereof are methylamine, tertiary-butyl-amine, cyclohexyl amine, benzyl amine, toluidine, aniline, nonyl aniline, dodecyl aniline, napthyl amine.
The iminodiimides described herein are effectively used in any lubricating media in which the lubricant base is a petroleum product, such as a mineral oil or a synthetic fluid. The synthetic fluids include synthetic hydrocarbons derived from long chain alkanes or olefin polymers, ester oils obtained from polyhydric alcohols and monocarboxylic alcohols and polycarboxylic acids or mixtures thereof. The lubricant media can also comprise a grease wherein a sufficient amount of the oil is employed to balance the grease after the desired amount of the thickening agent and other additive components are included in the grease formulation.
However, the novel additives of this invention may be used in organic media otherthan lubricant compositions, for example, liquid hydrocarbons such as distillate fuel oils.
The amount of additive compound used in the organic media may vary from 0.025 to 10% or more by weight of the base material, e.g., lubricant. The compositions preferably contain from 0.05 to 2% by weight of the additive based on the total weight of the composition. The compositions can also contain any other additive compounds known in the art such as antioxidants, antiwear and anticorrosion inhibitors without detrimentally affecting the pour depressant and UV stabilization characteristics of the subject iminodiimide additive compounds.
The following examples illustrate the present invention.
Example 1
0.055 moles (17.5 gms) of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA) were mixed with 0.17 moles of C16H33NH2 and heated until reaction was complete (about 3 hours). 0.17 moles of water (3.0 gms) were collected by entrainment distillation with toluene. The resultant product was identified as having the following structure:
Analysis: Calculated: C78.66, H 10.66 N4.23
Found: C78.55, H 10.60 N4.08
Melting Point- 600C Example 2
0.1 gm of the product of Example 1 was mixed with 100 gms of a hydrocracked oil and the resultant solution tested for light stability (Windowsill Test)*. A sample of hydrocracked oil not containing an additive compound as disclosed herein was tested similarly as a "control".After one day the "control" sample, i.e., hydrocracked oil withoutthe compound of Example 1 became hazy and precipitated brown material while the sample containing 0.1% of the compound of Example 1 did not. Further, after 8 days the sample containing the additive compound of the invention was still clear and without signs of precipitate formation.
* Atestwherein the material to be tested is placed on a windowsill in the sunlight and thereby exposed to UV light.
Example 3
A 1 gm sample of the product of Example 1 was tested in accordance with Example 2. After 3 months the sample (containing additive in accordance with this invention) was still clear and without signs of precipitate formation.
Example 4
A fuel oil, properties shown in Table 1, was mixed with 0.5% by wt. of the product of Example 1 and subjected to the pour point depressant test.
TABLE 1
Properties of No. 2 fuel oil
Sulfur, total % wt. 1.09
Sulfur, mercaptan % wt. 0.0109
Conradson Carbon, CCR % wt. < .01
Color, Saybolt +8.
Corrosion, Copper Strip, 2 hr at 2120F 1A Density at 150C 0.8417
Distillation, F, ASTM (D86)
IBP 404
10% 499
20% 524
50% 556
90% 608
EP 634
Flash Point, COC, 0F 245
Flash Point, Pensky Martens, CC,0F 205
Gum, Existent, mg/100 ml 27.0
Hydrocarbons, High Mass Spec.
C,O+ Paraffins 52.0
Mononaphthenes 15.4
Polynaphthenes 7.2
Aromatics 25.5
Three samples of the fuel oil each containing 0.5% of the product of Example 1 were treated as indicated below prior to measuring. The tests were done with a falling ball type viscometer in the following manner.
A sample of oil is placed in a graduated cylinder and thermostatically controlled to and maintained at the desired temperature. The oil is then cooled. A stainless steel ball is then dropped in the oil sample and its progress in the oil observed. As the oil sample cools down further the progress of another identical stainless steel ball is observed. The temperature at which the cooled oil does not allow such a steel ball to continue falling is then recorded. A similar sample of the reference oil is treated in an identical manner.
TABLE 2
Ref. Fuel Ref. Fuel + 0.5% Additive Treatment -8"F -14 Preheat at700C for
1/2 hour. Cool to room
temperature, then measure.
-9"F -15 11 -8"F -18 Preheat at 70 C for
1/2 hour. Left overnight,
then heat at 900C for 1/2
hour. Cool to room
temperature, then measure.
Examples 2, 3 and 4 demonstrate that the iminodiimides of BTDA according to the present invention provide excellent pour point depressant and UV stabilization characteristics for liquid hydrocarbon compositions such as hydrocracked compositions such as hydrocracked oils and distillate fuel oils.
Claims (10)
1. A compound having the following general structure:
where R is H, alkyl having from 1 to 36 carbon atoms, aryl, aralkyl or alkaryl having from 6 to about 36 carbon atoms.
2. The compound of Claim 1 where R is alkyl having from 10 to 26 carbon atoms.
3. The compound of Claim 2 where R has 16 carbon atoms.
4. A composition comprising a major amount of an appropriate organic medium and a minor amount effective to impart pour depressant properties and ultra-violet stabilization characteristics thereto of a compound having the following general structure:
where R is H, alkyl having from 1 to about 36 carbon atoms, aryl, aralkyl or alkaryl having from 6 to about 36 carbon atoms.
5. The composition of Claim 4 where the organic medium is an oil of lubricating viscosity or a grease prepared therefrom.
6. The composition of Claim 5 where the lubricant is a hydrocracked oil.
7. The composition of Claim 4 where the organic medium oil is a distillate fuel oil.
8. The composition of Claim 1 which contains from about 0.025 to about 10% by weight of said compound based on the total weight of the composition.
9. The composition of Claim 8 which contains from about 0.05 to 2% by weight of said compound.
10. A composition according to Claim 4 substantially as described in the foregoing Examples.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7840180A GB2035295A (en) | 1978-10-11 | 1978-10-11 | Novel iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7840180A GB2035295A (en) | 1978-10-11 | 1978-10-11 | Novel iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2035295A true GB2035295A (en) | 1980-06-18 |
Family
ID=10500272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7840180A Withdrawn GB2035295A (en) | 1978-10-11 | 1978-10-11 | Novel iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2035295A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0527365A1 (en) * | 1991-08-13 | 1993-02-17 | DSM Chemie Linz GmbH | Benzophenoniminodiimides and thermostable polymers derived therefrom |
| DE4129325A1 (en) * | 1991-09-04 | 1993-03-11 | Chemie Linz Deutschland | New bis-(hydroxy- or carboxy-alkyl- or aryl)-benzophenone imino:di:imide(s) - useful as monomers for prodn. of poly:ester(s) and poly:amide(s) with high thermal stability, low Tg, good solubility and thermoplastic processability |
| US5453515A (en) * | 1991-08-13 | 1995-09-26 | Chemie Linz Gesellschaft M.B.H. | Benzophenone iminodiimides and heat-stable polymers derived therefrom |
| EP1012217A1 (en) * | 1997-04-18 | 2000-06-28 | Mobil Oil Corporation | Friction reducing additives for fuels and lubricants |
-
1978
- 1978-10-11 GB GB7840180A patent/GB2035295A/en not_active Withdrawn
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0527365A1 (en) * | 1991-08-13 | 1993-02-17 | DSM Chemie Linz GmbH | Benzophenoniminodiimides and thermostable polymers derived therefrom |
| US5288876A (en) * | 1991-08-13 | 1994-02-22 | Chemie Linz Gesellschaft G.M.B.H. | Benzophenone iminodiimides and heat-stable polymers derived therefrom |
| AT397799B (en) * | 1991-08-13 | 1994-06-27 | Chemie Linz Gmbh | BENZOPHENONIMINODIIMIDES AND DERIVED THERMOSTABLE POLYMERS |
| US5453515A (en) * | 1991-08-13 | 1995-09-26 | Chemie Linz Gesellschaft M.B.H. | Benzophenone iminodiimides and heat-stable polymers derived therefrom |
| DE4129325A1 (en) * | 1991-09-04 | 1993-03-11 | Chemie Linz Deutschland | New bis-(hydroxy- or carboxy-alkyl- or aryl)-benzophenone imino:di:imide(s) - useful as monomers for prodn. of poly:ester(s) and poly:amide(s) with high thermal stability, low Tg, good solubility and thermoplastic processability |
| EP1012217A1 (en) * | 1997-04-18 | 2000-06-28 | Mobil Oil Corporation | Friction reducing additives for fuels and lubricants |
| EP1012217A4 (en) * | 1997-04-18 | 2000-06-28 | Mobil Oil Corp | Friction reducing additives for fuels and lubricants |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |