US2871135A - Method for producing drying oils and the oil so produced - Google Patents
Method for producing drying oils and the oil so produced Download PDFInfo
- Publication number
- US2871135A US2871135A US602439A US60243956A US2871135A US 2871135 A US2871135 A US 2871135A US 602439 A US602439 A US 602439A US 60243956 A US60243956 A US 60243956A US 2871135 A US2871135 A US 2871135A
- Authority
- US
- United States
- Prior art keywords
- oil
- drying
- raw
- produced
- synthetic
- 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
- 238000001035 drying Methods 0.000 title claims description 41
- 239000003921 oil Substances 0.000 title description 84
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 24
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 150000004665 fatty acids Chemical class 0.000 claims description 23
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 6
- -1 ALUMINUM COMPOUND Chemical class 0.000 claims description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 description 80
- 238000000034 method Methods 0.000 description 16
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 239000000944 linseed oil Substances 0.000 description 13
- 235000021388 linseed oil Nutrition 0.000 description 12
- 241000252203 Clupea harengus Species 0.000 description 9
- 235000019514 herring Nutrition 0.000 description 9
- 150000001399 aluminium compounds Chemical class 0.000 description 8
- 235000012343 cottonseed oil Nutrition 0.000 description 5
- 125000005456 glyceride group Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000010698 whale oil Substances 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000002385 cottonseed oil Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 241000283153 Cetacea Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D191/00—Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
- C09D191/005—Drying oils
Definitions
- the enolized aluminum-alcoholate then reacts with 2 moles of a fatty acid thus forming a drying oil the constitution of which is explained by the replacement of the 2 moles alcohol by 2 moles fatty acids while the enolic compound remains in its place bonded to the aluminum via the O-bridge.
- the mixture of the natural and the synthetic oils is carried out either at room temperature or at an elevated temperature. Mixing may be elfected by agitating or stirring until the components are intimately mixed and from a homogenous composition. Driers such as lead-, cobaltand/or manganese salts, and/or pigments, may be added in known manner.
- the action of the addition of the synthetic oils, for instance on linseed oil and other drying natural oils consists in a considerable acceleration of the drying process of the oils so that the duration of this process may be reduced to about /5-% of the drying time of the original drying oils used in the mixture.
- the non drying oils will be converted into drying oils having shorter drying times than boiled linseed oil.
- the water and weather resistance of the oil is considerably improved by the addition of said synthetic oil.
- the films obtained from linseed oil and other drying oils swell in water and are spoiled after a few days.
- the films of expensive isomerized linseed oils are dim already after having'been exposed to the influence of water for one day.
- the films produced by oils according to the pres ent invention remain clear even after having been exposed to water for months and they do not swell in water.
- the pigmentation properties, the adhesion, the flexibility etc. are excellent.
- the oil composition according to the invention is compatible with all other raw materials conventionally used in producing lacquers and varnishes.
- oils and their films can be attained by changing the ratio between the quantities of the natural oil and the synthetic oil.
- range of viscosity of the oils which are produced may vary from a low viscosity oil like the known natural oils to the viscosity of standoils.
- all films of oils produced according to the present invention are repellent to fungi.
- Raw Soybean Oil Raw Soybean Oll,'sicActivted Raw Soybean Oil, with synthetic oil 4- feebIe -- excellent no Do.
- Raw Herring Oil sicactivted Raw Herring Oil, with synthetic oil 0. Row lien-inn Oil, with synthetic oiland pigmen sozlgxol treated Herring Oil (Iodine Number Solexol treated Herring Oil (Iodine Number non drying 220); sicactivted. SoleIoI treated Herring -Oil (Iodine, Number 6 1 I10 0 110 D0.
- Solezol treated Herring Oil (Iodine Number 5 6; about 1---. 0 "d n0 D0.
- compositions include, according to the invention, a mixture of the respective oil with synthetic oils produced by a condensation improved properties in all respects.
- the organicaluminium compound consists of. an cnolic compound, the: en-
- olic component of which is i. e.-. aceto-acetic ester; malonio diethyl ester or acetonylacetom Any of these compounds may be used in the ,dilferentexamplcs.
- the drying time of the mixture is /2 hour and .the viscosity (12) 40 kgs. raw Chinese Wood oil are'mixed'at 50 C. with 60 kgs. of a synthetic oil, produced by con densation of Whale oil fatty acid with an organic aluminium compound of the kind specified above.
- the drying time of the mixture is less than /2 hour and the viscosity 230 sec.
- the synthetic oil is producedin thehigher fatty acids and mixtures of unsaturated higher fatty acids with one mole of an organic aluminum compound in which two valences of the aluminum are bonded to alcohols while one valence of the aluminum is bonded to oxygen of an enolic compound selected from the group consisting of acetoacetic ester, malonic diethyl ester and acetonyl acetone to form a synthetic oil and mixing it with a higher fatty acid triglyceride.
- a drying oil comprising a mixture of glyceride of a higher fatty acid and a synthetic oil obtained by condensing two moles of a fatty acid selected from the group consisting of unsaturated higher fatty acids and mixtures of unsaturated higher fatty acids with saturated higher fatty acids with one mole of an aluminum compound prepared by reacting one mole of aluminum alcoholate and one mole of an enolic compound selected from the group consisting of acetoacetic ester, malonic diethyl ester and acetonyl acetone.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE354879X | 1955-08-24 | ||
| SE71155X | 1955-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2871135A true US2871135A (en) | 1959-01-27 |
Family
ID=26654762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US602439A Expired - Lifetime US2871135A (en) | 1955-08-24 | 1956-08-06 | Method for producing drying oils and the oil so produced |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2871135A (de) |
| BE (1) | BE550505A (de) |
| CH (1) | CH354879A (de) |
| DE (1) | DE1076860B (de) |
| FR (1) | FR1156062A (de) |
| GB (1) | GB798351A (de) |
| NL (1) | NL93693C (de) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097957A (en) * | 1959-06-18 | 1963-07-16 | Exxon Research Engineering Co | Coating composition with blocked alcoholates therein |
| US3258475A (en) * | 1963-08-13 | 1966-06-28 | Faulkner Raymond Noel | Film-forming organometallic derivatives of fatty acids |
| US3287384A (en) * | 1961-01-11 | 1966-11-22 | Houghton & Co E F | Ortho esters of aluminum, silicon or titanium with a metal soap of a hydroxy-fatty acid |
| US4090886A (en) * | 1974-01-18 | 1978-05-23 | Manchem Limited | Aluminum based air drying compositions |
| US4264370A (en) * | 1976-03-01 | 1981-04-28 | Manchem Limited | Method for preparing aluminum-based air drying compositions |
| US4529555A (en) * | 1982-09-27 | 1985-07-16 | Kawaken Fine Chemicals Co., Ltd. | Surface modifier for powdery or granular substance having hydrophilic surface comprising an aluminum chelate compound |
| US4576647A (en) * | 1982-09-27 | 1986-03-18 | Kawaken Fine Chemicals Co., Ltd. | Oleophilic composition comprising a powdery or granular substance having a hydrophilic surface and an aluminum chelate compound |
| US6887398B1 (en) * | 1997-09-27 | 2005-05-03 | Rwe-Dea Aktiengesellschaft Fur Mineraloel Und Chemie | Aluminum acetoacetate compounds, the production and use thereof as printing ink additives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1281610B (de) * | 1959-06-08 | 1968-10-31 | Glidden Co | UEberzugsmittel fuer Metalle |
| FR2975836B1 (fr) | 2011-05-24 | 2014-07-04 | Schneider Electric Ind Sas | Appareillage electrique a isolation gazeuse ayant des moyens de regulation de la pression de gaz |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE878826C (de) * | 1951-01-13 | 1953-06-08 | Albert Ag Chem Werke | Verfahren zur Verbesserung von Bindemitteln fuer Lacke, Anstrichmittel, Kitte, Klebstoffe und plastische Massen auf der Grundlage von OElen, Naturharzen oder Kunstharzen |
-
0
- BE BE550505D patent/BE550505A/xx unknown
- NL NL93693D patent/NL93693C/xx active
-
1956
- 1956-04-12 DE DEN12088A patent/DE1076860B/de active Pending
- 1956-08-06 CH CH354879D patent/CH354879A/de unknown
- 1956-08-06 US US602439A patent/US2871135A/en not_active Expired - Lifetime
- 1956-08-14 GB GB24814/56A patent/GB798351A/en not_active Expired
- 1956-08-21 FR FR1156062D patent/FR1156062A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097957A (en) * | 1959-06-18 | 1963-07-16 | Exxon Research Engineering Co | Coating composition with blocked alcoholates therein |
| US3287384A (en) * | 1961-01-11 | 1966-11-22 | Houghton & Co E F | Ortho esters of aluminum, silicon or titanium with a metal soap of a hydroxy-fatty acid |
| US3258475A (en) * | 1963-08-13 | 1966-06-28 | Faulkner Raymond Noel | Film-forming organometallic derivatives of fatty acids |
| US4090886A (en) * | 1974-01-18 | 1978-05-23 | Manchem Limited | Aluminum based air drying compositions |
| US4264370A (en) * | 1976-03-01 | 1981-04-28 | Manchem Limited | Method for preparing aluminum-based air drying compositions |
| US4529555A (en) * | 1982-09-27 | 1985-07-16 | Kawaken Fine Chemicals Co., Ltd. | Surface modifier for powdery or granular substance having hydrophilic surface comprising an aluminum chelate compound |
| US4576647A (en) * | 1982-09-27 | 1986-03-18 | Kawaken Fine Chemicals Co., Ltd. | Oleophilic composition comprising a powdery or granular substance having a hydrophilic surface and an aluminum chelate compound |
| US6887398B1 (en) * | 1997-09-27 | 2005-05-03 | Rwe-Dea Aktiengesellschaft Fur Mineraloel Und Chemie | Aluminum acetoacetate compounds, the production and use thereof as printing ink additives |
Also Published As
| Publication number | Publication date |
|---|---|
| GB798351A (en) | 1958-07-16 |
| FR1156062A (fr) | 1958-05-12 |
| CH354879A (de) | 1961-06-15 |
| DE1076860B (de) | 1960-03-03 |
| NL93693C (de) | |
| BE550505A (de) |
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