CN1045103C - Alkyl salicylate as additive of lubricant oil - Google Patents
Alkyl salicylate as additive of lubricant oil Download PDFInfo
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- CN1045103C CN1045103C CN94106385A CN94106385A CN1045103C CN 1045103 C CN1045103 C CN 1045103C CN 94106385 A CN94106385 A CN 94106385A CN 94106385 A CN94106385 A CN 94106385A CN 1045103 C CN1045103 C CN 1045103C
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- China
- Prior art keywords
- alkyl
- additive
- salicylate
- acid ester
- tensio
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- -1 Alkyl salicylate Chemical compound 0.000 title claims abstract description 44
- 229960001860 salicylate Drugs 0.000 title claims abstract description 32
- 239000000654 additive Substances 0.000 title claims abstract description 26
- 230000000996 additive effect Effects 0.000 title claims abstract description 26
- 239000000314 lubricant Substances 0.000 title claims abstract description 10
- 239000003921 oil Substances 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000013543 active substance Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229920002367 Polyisobutene Polymers 0.000 claims description 7
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000292 calcium oxide Substances 0.000 claims description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 4
- 235000011089 carbon dioxide Nutrition 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000002893 slag Substances 0.000 claims description 3
- 229960002317 succinimide Drugs 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009156 water cure Methods 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract description 20
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000001556 precipitation Methods 0.000 abstract description 6
- 239000010687 lubricating oil Substances 0.000 abstract description 5
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000000975 co-precipitation Methods 0.000 description 9
- 239000011575 calcium Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 230000003042 antagnostic effect Effects 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002199 base oil Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- ZTVIKZXZYLEVOL-DGKWVBSXSA-N 2-hydroxy-2-phenylacetic acid [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester Chemical group C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-DGKWVBSXSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000000203 Salix gracilistyla Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Lubricants (AREA)
Abstract
The present invention relates to an alkyl salicylate additive for lubricant oil, which has improved compatibility and the capability of oxidation. The lubricating oil additive of the present invention, which adopts alkyl calcium salicylate, effectively inhibit the generation of precipitates to a certain degree when the alkyl calcium salicylate is compounded with sulfonate, and the problem of compound precipitation of salicylate and the sulfonate can be solved by adjusting the dosage of alkenyl succinic acid ester. In addition, the performance of the alkyl salicylate product is better than or equivalent to that of the original products.
Description
The present invention relates to a kind of alkyl salicylate as additive of lubricant oil, especially relate to the alkyl salicylate as additive of lubricant oil that a kind of compatibility performance improves and antioxidant capacity improves, belong to the lubricating oil field.
Along with the fast development of automotive industry, more and more higher specification of quality has been proposed lubricating oil additive.The allotment recombiner has become the main flow of lubricating oil additive Application Areas so that multiple metal detergent is compound.
Usually, if do not influence each other between each additive component, just play a role independently, then the various performances of recombiner should be the mean value of this kind performance of component additive by the concentration weighting.But in fact have different interactions between each additive component and produce synergy or antagonistic action each other, sometimes even produce co-precipitation.Composite precipitation is the most extreme a kind of form of antagonistic action performance.
Alkylsalicylate and sulfonate are the main additive in the detergent for lubricating oil.Their compound uses will produce co-precipitation under certain condition.For improving the consistency of alkylsalicylate and sulfonate: forefathers carried out some research reports.The Heldeweg of Ying He Shell Co. Ltd, Rudolf, Frank etc. vulcanize the salicylate product, product after the sulfuration have the consistency improved (EP 168,880,168,110), but do not report that Acid Thiosalicylique salt and sulfonate have or not sedimentary problem after compound.Also there is the synthesis technique of people's p-sulfonic acid salt to carry out improvement, it is reported and improved its use properties, but also do not see the test of itself and salicylate convergent improvement effect.
Alkylsalicylate and sulfonate composite precipitation problem are found early in China, and are of long duration.The existence of this problem make lubricant oil metal detergent in recombiner development and in using difficulty bigger, it has also limited sulfonate and alkylsalicylate promoting the use of at home.This problem is since finding, forefathers had carried out a large amount of basic research work.Zhou Xiangzhai etc. once write articles and thought that co-precipitation partly was the material based on carbonate and tensio-active agent, used ashless dispersant can make it to spread out again and may not influence the use properties of product.In experiment,, also improved the consistency of salicylate really with sulfonate by calling in a certain amount of ashless dispersant.But still have the co-precipitation material, experiment does not fundamentally solve the problem of compound co-precipitation.
Purpose of the present invention will provide a kind of alkyl salicylate as additive of lubricant oil exactly, alkyl salicylate additive of the present invention has fabulous compatibility performance, thereby can solve the problem of alkylsalicylate and sulfonate composite precipitation effectively, and this additive performance is suitable with the salicylate performance that does not add tensio-active agent.
The object of the present invention is achieved like this: after designing one group of tensio-active agent and alkyl salicylate mixing, produce salicylate by the processing method of producing alkylsalicylate, the consistency of investigating itself and sulfonate then is co-precipitation quantity (percentage ratio).
Alkyl salicylate additive preparation method of the present invention is as follows: with boiling range is that 80～130 ℃ straight-run spirit and methyl alcohol joins in the reactor, mixes to stir and heats up; After temperature rises to 40～60 ℃, add calcium oxide, add metering water then, slaking 10-15 minute.After slaking reaction was finished, alkyl salicylate that adding mixes in advance and specific tensio-active agent carried out neutralization reaction 1 hour; Feed carbonic acid gas then, high basicity reaction 90 minutes.After reaction finishes, be warming up to 105 ℃, steam dehydration, methyl alcohol, add the gasoline dilution, centrifugal, steam desolventizing at last and get product.
The present invention relates to the alkyl salicylate as additive of lubricant oil that a kind of compatibility performance has improved.Add some tensio-active agent in its preparation process, as sulfonic acid, alkenyl succinic acid ester.Synthetic alkyl sodium salicylates such as polyisobutene-maleic anhydride can suppress sedimentary generation to a certain extent significantly after compound with sulfonate; By adjusting consumption, use the alkenyl succinic acid ester can solve the problem of salicylate with the sulfonate composite precipitation.
A kind of alkyl salicylate as additive of lubricant oil is characterized in that this additive prepares with following method: the solvent of metering and methyl alcohol are dropped into to heat up in the reactor be stirred to 40～60 ℃, add calcium oxide; Added water cure 10～15 minutes, and then alkyl salicylate and tensio-active agent were joined in the reactor together, neutralization reaction 1 hour fed carbonic acid gas 90 minutes then, reaction is warming up to 105 ℃ after finishing, and steams dehydration, methyl alcohol, the solubilizing agent dilution is centrifugal, removes slag, and steams desolventizing and gets product.It is characterized in that said tensio-active agent can be an alkyl benzene sulphonate (ABS), alkylbenzene sulfonate, dodecenylsuccinic acid ester or polyisobutene-maleic anhydride or polyisobutene succinimide.It is characterized in that described dodecenylsuccinic acid ester molecule formula is:
(half ester) wherein, R is the laurylene base, R ' can be C
8～15Alkyl, preferably C
10～12Straight chained alkyl.The add-on that it is characterized in that described tensio-active agent can be 5.0～20.0% (m/m), is preferably within 10～15% (m/m).It is characterized in that adding the alkylsalicylate of the above dodecenylsuccinic acid ester of 7% (m/m).
Advantage of the present invention and effect can be seen by the following examples, but those skilled in the art should be understood that, the following examples just further specify of the present invention, rather than the restriction scope of the invention, any change that does not exceed spirit and scope of the invention, all within the scope of the present invention.
Embodiment 1, in the 500ml there-necked flask that installs electronic stirring and condensation water trap, drop into the straight-run spirit 150ml of 80～130 ℃ of boiling ranges, industrial methanol 95ml, stirring is warming up to 50～55 ℃, adds calcium oxide 10.0g (purity 95%m/m), stirs 15 minutes, the warm water 6.0ml that slowly adds 70 ℃ then carried out slaking reaction 10～15 minutes.After reaction is finished, (acid number is 66.2mgKOH/g to add the alkyl salicylate that mixes, contain 90%) and dodecenylsuccinic acid ester (half ester, containing 10%) mixture 100.0g is in reactor, carried out neutralization reaction about 60 minutes, and fed carbonic acid gas with 150ml/min speed then and carry out the about 90min of metallization reaction.After reaction finishes, add the dilution of 100ml gasoline, centrifugal removing slag under 3000 rev/mins of rotating speeds steamed desolventizing then and got product.The product calcium contents is 5.31%, and base number is 150mgKOH/g.
Embodiment 2, press the operation of embodiment 1, are the tensio-active agent synthesis of alkyl salicylate that tensio-active agent alkenyl succinic acid ester is changed consumption or change other into, and its character sees Table I.(tensio-active agent drops into percentage amounts by adding total amount of surfactant).
Table I synthesis of alkyl salicylate character
| Sequence number | Calcium contents (%) | Base number (mgKOH/g) | Remarks |
| Examination-1 | 5.31 | 150 | Add the alkenyl succinic acid ester, 7% |
| Examination-2 | 5.93 | 169 | Add the alkenyl succinic acid ester, 14% |
| Examination-3 | 5.32 | 150 | Add the alkenyl succinic acid ester, 5% |
| Examination-4 | 5.50 | 153 | Add the alkenyl succinic acid ester, 3% |
| Examination-5 | 5.60 | 156 | Add alkyl benzene sulphonate (ABS) 10% (JAN=113.0mgKOH/g) |
| Examination-6 | 5.30 | 148 | Add low basicity calcium sulphonate, 10% |
| Examination-7 | 5.23 | 143 | Add polyisobutene dicarboxylic anhydride (MW=1320), 10% |
| Examination-8 | 5.22 | 141 | Add single polyisobutene horse imide, 10% hung |
Embodiment 3, in the 100ml beaker, accurately take by weighing each 2.5 ± 0.1g of alkyl salicylate and sulfonate, add 45.0g 300SN base oil.Stir-concoction is 15 minutes under 80 ℃ of temperature, oil solution is poured into be with (its least reading is 0.01ml, capacity 50ml) in the graduated taper sedimentation pipe.One group in storage at normal temperature, and one group places 100 ℃ of storages of high temperature in the baking oven, record period of storage and the relation that generates the sediment amount.The results are shown in Table II.
In the table II, T-109 is that alkyl sodium salicylate is produced in blue refining, and Ca% is 6.0, and base number is 160mgKOH/g; HE-600 is U.S.'s ethyl corporation sulfonate, and Ca%12.11, base number are 293.7mgKOH/g; On-202C is that factory of shanghai refinery produces sulfonate, Ca%11.17, base number are 282.0mgKOH/g.
From table II test-results as can be seen: the synthetic salicylate is followed successively by from small to large with sulfonate co-precipitation amount:
Examination-1, examination-2＜examination-6＜examination 7, examination-8＜examination-5＜examination-4＜examination-3＜T-109.
That is to say, in salicylate salt process, add a certain amount of other tensio-active agents and all can reduce the co-precipitation amount to a certain extent, that is to say, can slow down antagonistic effect therebetween to a certain extent.Particularly when dodecenylsuccinic acid ester addition greater than 7.0% the time, no co-precipitation generates, and has solved salicylate with the sulfonate sedimentary problem that coexists.
Under the identical condition of addition, during equal 10% (m/m), can improve salicylate and be followed successively by: dodecenylsuccinic acid ester (half ester)＞low alkali value calcium sulphonate＞polyisobutylene butanedioic anhydride or polyisobutene succinimide (the single extension)＞alkyl benzene sulphonate (ABS) with the tensio-active agent of sulfonate coexistence precipitation or antagonistic effect.
Salicylate performance and T-109 performance that compatibility performance has improved relatively see Table III.From the table III, as can be seen, add table such as alkenyl succinic acid ester, polyisobutene maleic anhydride and Phenylsulfonic acid and the resistance of oxidation of promoting agent synthetic product is greatly improved; Dispersiveness has some improvement, and more with product dispersing property raising after adding polyisobutene-maleic anhydride tensio-active agent, and lacquering plate performance also has certain improvement or suitable.
Table II alkylsalicylate and sulfonate composite testing result
| Alkylsalicylate | Overbased sulfonate | Shelf test (sinkability, %) | ||||
| Normal temperature, 30d | 100℃,24h | 100℃,48h | 100℃,4d | 100℃,7d | ||
| T-109 | HE-611 | 0.00 | 0.22 | 0.44 | 0.60 | 0.60 |
| On-202C | 0.00 | 0.10 | 0.24 | 0.48 | 0.48 | |
| Examination-1 | HE-611 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 |
| On-202C | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | |
| Examination-2 | HE-611 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 |
| On-202C | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | |
| Examination-3 | HE-611 | 0.00 | 0.00 | 0.00 | 0.06 | 0.06 |
| On-202C | 0.00 | 0.00 | 0.06 | 0.10 | 0.10 | |
| Examination-4 | HE-611 | 0.00 | 0.00 | 0.16 | 0.36 | 0.36 |
| On-202C | 0.00 | 0.00 | 0.18 | 0.30 | 0.30 | |
| Examination-5 | HE-611 | 0.00 | 0.60 | 0.30 | 0.30 | 0.30 |
| On-202C | 0.00 | 0.00 | 0.06 | 0.16 | 0.16 | |
| Examination-6 | HE-611 | 0.00 | 0.00 | 0.02 | 0.02 | 0.02 |
| On-202C | 0.00 | 0.00 | 0.04 | 0.06 | 0.06 | |
| Examination-7 | HE-611 | 0.00 | 0.02 | 0.06 | 0.06 | 0.06 |
| On-202C | 0.00 | 0.02 | 0.04 | 0.12 | 0.12 | |
| Examination-8 | HE-611 | 0.00 | 0.02 | 0.04 | 0.04 | 0.06 |
| On-202C | 0.00 | 0.04 | 0.06 | 0.12 | 0.12 | |
The salicylate that table III compatibility performance has improved with the T-109 performance relatively
Annotate: base oil: 300ZN, additive add-on 2% (m/m); PW-1 bench testing oil product total dose is 5.5%, contains bigcatkin willow hydrochlorate 1.5% (m/m); The SDT distributed test is 1.0g agent+9.0g greasy filth+10.0g base oil, drips to put on the filter paper, calculates greasy filth loop diameter and scraper ring diameter ratio.
Claims (5)
1. alkyl salicylate as additive of lubricant oil, this additive is prepared by following method, it is characterized in that: the solvent of metering and methyl alcohol are dropped into to heat up in the reactor be stirred to 40～60 ℃, add calcium oxide; Added water cure 10～15 minutes, and then alkyl salicylate and tensio-active agent were joined in the reactor together, neutralization reaction 1 hour fed carbonic acid gas 90 minutes then, reaction is warming up to 105 ℃ after finishing, and steams dehydration, methyl alcohol, the solubilizing agent dilution is centrifugal, removes slag, and steams desolventizing and gets product.
2. additive according to claim 1 is characterized in that said tensio-active agent can be an alkyl benzene sulphonate (ABS), alkylbenzene sulfonate, dodecenylsuccinic acid ester or polyisobutene-maleic anhydride or polyisobutene succinimide.
3. additive according to claim 1 is characterized in that described dodecenylsuccinic acid ester molecule formula is:
(half ester) wherein, R is the laurylene base, R ' can be C
8～15Alkyl, preferably C
10～12Straight chained alkyl.
4. additive according to claim 1, the add-on that it is characterized in that described tensio-active agent can be 5.0～20.0% (m/m), is preferably within 10～15% (m/m).
5. additive according to claim 1 is characterized in that adding the alkylsalicylate of the above dodecenylsuccinic acid ester of 7% (m/m).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94106385A CN1045103C (en) | 1994-06-18 | 1994-06-18 | Alkyl salicylate as additive of lubricant oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94106385A CN1045103C (en) | 1994-06-18 | 1994-06-18 | Alkyl salicylate as additive of lubricant oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1199086A CN1199086A (en) | 1998-11-18 |
| CN1045103C true CN1045103C (en) | 1999-09-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94106385A Expired - Lifetime CN1045103C (en) | 1994-06-18 | 1994-06-18 | Alkyl salicylate as additive of lubricant oil |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7585822B2 (en) * | 2004-11-23 | 2009-09-08 | Crompton Corporation | Emulsifier blends for lubricating oils |
| JP6362095B2 (en) | 2014-06-17 | 2018-07-25 | キヤノン株式会社 | Illumination apparatus, exposure apparatus, adjustment method, and article manufacturing method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0227812A1 (en) * | 1985-06-19 | 1987-07-08 | Pixar | Pseudo-random point sampling techniques in computer graphics |
| EP0294944A2 (en) * | 1987-06-12 | 1988-12-14 | Taiyo Chemical Co. Ltd. | Lubricant compositions and method for preparation of same |
| WO1994019434A1 (en) * | 1993-02-22 | 1994-09-01 | Exxon Research & Engineering Company | Lubricant composition containing alkoxylated amine salts of acids |
| WO1994028095A1 (en) * | 1993-05-27 | 1994-12-08 | Exxon Research & Engineering Company | Lubricating oil composition |
-
1994
- 1994-06-18 CN CN94106385A patent/CN1045103C/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0227812A1 (en) * | 1985-06-19 | 1987-07-08 | Pixar | Pseudo-random point sampling techniques in computer graphics |
| EP0294944A2 (en) * | 1987-06-12 | 1988-12-14 | Taiyo Chemical Co. Ltd. | Lubricant compositions and method for preparation of same |
| WO1994019434A1 (en) * | 1993-02-22 | 1994-09-01 | Exxon Research & Engineering Company | Lubricant composition containing alkoxylated amine salts of acids |
| WO1994028095A1 (en) * | 1993-05-27 | 1994-12-08 | Exxon Research & Engineering Company | Lubricating oil composition |
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| Publication number | Publication date |
|---|---|
| CN1199086A (en) | 1998-11-18 |
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