JPH0473475B2 - - Google Patents
Info
- Publication number
- JPH0473475B2 JPH0473475B2 JP60057684A JP5768485A JPH0473475B2 JP H0473475 B2 JPH0473475 B2 JP H0473475B2 JP 60057684 A JP60057684 A JP 60057684A JP 5768485 A JP5768485 A JP 5768485A JP H0473475 B2 JPH0473475 B2 JP H0473475B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- copolymer
- vinyl acetate
- additive
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 claims description 47
- 239000000654 additive Substances 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 25
- 238000009835 boiling Methods 0.000 claims description 20
- 239000000295 fuel oil Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- -1 nitrogen-containing compound Chemical class 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 229920001567 vinyl ester resin Polymers 0.000 claims description 7
- 239000003209 petroleum derivative Substances 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000000446 fuel Substances 0.000 description 36
- 238000012360 testing method Methods 0.000 description 24
- 239000001993 wax Substances 0.000 description 17
- 239000002480 mineral oil Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 235000010446 mineral oil Nutrition 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 239000005038 ethylene vinyl acetate Substances 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229910017464 nitrogen compound Inorganic materials 0.000 description 5
- 150000002830 nitrogen compounds Chemical class 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000003966 growth inhibitor Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- ARDVXKRWZGPMRP-ZQHSETAFSA-N (E)-4-octacosoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCOC(=O)\C=C\C(O)=O ARDVXKRWZGPMRP-ZQHSETAFSA-N 0.000 description 1
- IIPCXIGUIPAGQB-OUKQBFOZSA-N (e)-4-dodecoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCCCOC(=O)\C=C\C(O)=O IIPCXIGUIPAGQB-OUKQBFOZSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical class OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- VEPKQEUBKLEPRA-UHFFFAOYSA-N VX-745 Chemical compound FC1=CC(F)=CC=C1SC1=NN2C=NC(=O)C(C=3C(=CC=CC=3Cl)Cl)=C2C=C1 VEPKQEUBKLEPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 244000240602 cacao Species 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000003484 crystal nucleating agent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- OVHKECRARPYFQS-UHFFFAOYSA-N cyclohex-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC=C1 OVHKECRARPYFQS-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- YHPLDIMIJCPNBP-UHFFFAOYSA-N n-methyldocosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCNC YHPLDIMIJCPNBP-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- USYCSHPNZNNCCU-UHFFFAOYSA-N prop-1-en-2-yl prop-2-enoate Chemical compound CC(=C)OC(=O)C=C USYCSHPNZNNCCU-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848407403A GB8407403D0 (en) | 1984-03-22 | 1984-03-22 | Middle distillate compositions |
| GB8407403 | 1984-03-22 | ||
| GB8420436 | 1984-08-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60217294A JPS60217294A (ja) | 1985-10-30 |
| JPH0473475B2 true JPH0473475B2 (fr) | 1992-11-20 |
Family
ID=10558484
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5768385A Granted JPS60217293A (ja) | 1984-03-22 | 1985-03-22 | 燃料油の低温特性改良用添加剤及び該添加剤含有石油蒸留留出物 |
| JP5768485A Granted JPS60217294A (ja) | 1984-03-22 | 1985-03-22 | 燃料油の低温特性改良用添加剤及び該添加剤を含む石油蒸留留出物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5768385A Granted JPS60217293A (ja) | 1984-03-22 | 1985-03-22 | 燃料油の低温特性改良用添加剤及び該添加剤含有石油蒸留留出物 |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPS60217293A (fr) |
| DD (2) | DD240024A5 (fr) |
| GB (1) | GB8407403D0 (fr) |
| RU (1) | RU2034904C1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101453376B1 (ko) * | 2014-02-24 | 2014-10-22 | (주) 디케이 문교 | 치과용 석고모형 제조방법 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8705839D0 (en) * | 1987-03-12 | 1987-04-15 | Exxon Chemical Patents Inc | Fuel compositions |
| JPH01103699A (ja) * | 1987-07-28 | 1989-04-20 | Sumitomo Chem Co Ltd | 燃料油組成物 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51123203A (en) * | 1975-04-07 | 1976-10-27 | Exxon Research Engineering Co | Polymers used for improving normal temperature flow in distilled hydrocarbon oil |
| GB1469016A (en) * | 1973-10-31 | 1977-03-30 | Exxon Research Engineering Co | Middle distillate fuel oil containing mixture of polymers to improve cold flow properties |
| JPS5839472A (ja) * | 1981-09-03 | 1983-03-08 | Mitsubishi Electric Corp | プリンタ装置 |
| JPS59189192A (ja) * | 1983-04-12 | 1984-10-26 | Nippon Oil & Fats Co Ltd | 燃料油用流動性向上剤 |
| JPS6057683A (ja) * | 1983-09-08 | 1985-04-03 | Canon Inc | 光導電部材 |
-
1984
- 1984-03-22 GB GB848407403A patent/GB8407403D0/en active Pending
-
1985
- 1985-03-21 RU SU3887750 patent/RU2034904C1/ru active
- 1985-03-22 JP JP5768385A patent/JPS60217293A/ja active Granted
- 1985-03-22 DD DD27436085A patent/DD240024A5/de not_active IP Right Cessation
- 1985-03-22 JP JP5768485A patent/JPS60217294A/ja active Granted
- 1985-03-22 DD DD85274352A patent/DD236753A5/de not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1469016A (en) * | 1973-10-31 | 1977-03-30 | Exxon Research Engineering Co | Middle distillate fuel oil containing mixture of polymers to improve cold flow properties |
| JPS51123203A (en) * | 1975-04-07 | 1976-10-27 | Exxon Research Engineering Co | Polymers used for improving normal temperature flow in distilled hydrocarbon oil |
| JPS5839472A (ja) * | 1981-09-03 | 1983-03-08 | Mitsubishi Electric Corp | プリンタ装置 |
| JPS59189192A (ja) * | 1983-04-12 | 1984-10-26 | Nippon Oil & Fats Co Ltd | 燃料油用流動性向上剤 |
| JPS6057683A (ja) * | 1983-09-08 | 1985-04-03 | Canon Inc | 光導電部材 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101453376B1 (ko) * | 2014-02-24 | 2014-10-22 | (주) 디케이 문교 | 치과용 석고모형 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8407403D0 (en) | 1984-05-02 |
| RU2034904C1 (ru) | 1995-05-10 |
| DD240024A5 (de) | 1986-10-15 |
| JPH0473474B2 (fr) | 1992-11-20 |
| DD236753A5 (de) | 1986-06-18 |
| JPS60217294A (ja) | 1985-10-30 |
| JPS60217293A (ja) | 1985-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |