US2388257A - Bodied oil and method - Google Patents
Bodied oil and method Download PDFInfo
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- US2388257A US2388257A US2388257DA US2388257A US 2388257 A US2388257 A US 2388257A US 2388257D A US2388257D A US 2388257DA US 2388257 A US2388257 A US 2388257A
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- United States
- Prior art keywords
- oil
- oiticica
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- varnish
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- 239000003921 oil Substances 0.000 description 136
- 239000002966 varnish Substances 0.000 description 58
- 239000002383 tung oil Substances 0.000 description 26
- 238000010438 heat treatment Methods 0.000 description 18
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 16
- 230000005587 bubbling Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 8
- 239000011707 mineral Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 235000015096 spirit Nutrition 0.000 description 8
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 description 6
- 229940023488 Pill Drugs 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 229910052803 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Chemical class 0.000 description 4
- 238000010411 cooking Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 240000000972 Agathis dammara Species 0.000 description 2
- 241000016649 Copaifera officinalis Species 0.000 description 2
- 229920002871 Dammar gum Polymers 0.000 description 2
- 229920003261 Durez Polymers 0.000 description 2
- 239000004868 Kauri gum Substances 0.000 description 2
- 241000736873 Tetraclinis articulata Species 0.000 description 2
- 230000001464 adherent Effects 0.000 description 2
- 230000003190 augmentative Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000012813 breadcrumbs Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- IFSWBZCGMGEHLE-UHFFFAOYSA-L cobalt(2+);naphthalene-2-carboxylate Chemical compound [Co+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 IFSWBZCGMGEHLE-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- BFWHHDQLPCRKOU-UHFFFAOYSA-M hydroxy(naphthalen-2-yl)methanolate;manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C([O-])O)=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 BFWHHDQLPCRKOU-UHFFFAOYSA-M 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011133 lead Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- XYXLRVFDLJOZJC-HUGPZQPHSA-L manganese(2+);(Z)-octadec-9-enoate;(E)-octadec-9-enoate Chemical compound [Mn+2].CCCCCCCC\C=C\CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O XYXLRVFDLJOZJC-HUGPZQPHSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000025 natural resin Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(Z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 2
- MXODCLTZTIFYDV-UHFFFAOYSA-L zinc;1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Zn+2].C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O.C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O MXODCLTZTIFYDV-UHFFFAOYSA-L 0.000 description 2
- DPQXAUXLLDWUMQ-UHFFFAOYSA-L zinc;naphthalene-2-carboxylate Chemical compound [Zn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 DPQXAUXLLDWUMQ-UHFFFAOYSA-L 0.000 description 2
Definitions
- This invention relates to an improved bodied oiticica oil and to the method of making it; it also relates to varnishes made from this bodied oil.
- Oiticica oil is a relatively inexpensive drying oil that has been used heretofore in lieu of China wood oil; however, its use has not been very successful because it does not have the desiredquick-bodying char- Varnishes formed from this oil are objectionable from a cost standpoint because they can be thinned only to a 1imited extent with thinners and because the films deposited from these varnishes are nonelastic and brittle off readily from surfaces on which they are formed. In addition, these oiticica oil varnishes do not dry rapidly and do not have certain other desired physical characteristics uch as spread and flow.
- oiticica oil can be treated in accordance with our invention and that the resulting treated oil will body in the kettle atleast as fast as China wood oil and even faster, as desired. Moreover, the treated oil of our invention, when used in a varnish, will produce a film similar to China wood oil in drying and elasticity and which has none of the objectionable brittleness characteristic of films formed from untreated oiticica oil-containing varnishes.
- oiticica oil is heated in a suitable vessel, for example, a steamjacketed kettle, to a temperature in the order of about 325 F. to 370 F., preferably about 350 F., and held at approximately-that temperature for about /2 hour to 2 hours.
- air from any suitable source of supply is introduced into the body of oil from a jet or nozzle or other air distributing device located, preferably, at or adjacent the botttom of the vessel.
- the effectiveness of contact between the oil and air may be augmented by mechanical agitation, if desired, in which case the kettlemay be provided with an agitator.
- the amount of air bubbling through the body of heated oil may be varied rather widely to meet any desired requirement in the treated oil; however, for most purposes, the introduction of air at the rate of about 2 cu. ft. per minute for each 100 lbs. of oil is sufficient.
- This combined heat and air treatment is continued until the desired bodying qualities are obtained. This can be determined experimentally by making gelation tests of samples from the kettle from time to time. In'most instances, the desired bodying qualities are obtained in from about 4 30 to minutes.
- the heatand air-bodying treatment of our invention may be carriedout in the presence of catalysts.
- suitable catalysts are zinc oleate, zinc resinate, manganese oleate and the like as well as salts of nickel, cobalt, lead, iron and the like, and finely divided metals such as zinc dust and the like.
- fast-bodying oiticica oils may be obtained with a Worstall test of about 4 to about 7 minutes, as desired, as compared with China wood oil, the standard, with a Worstall test varying from about 6 to .8 minutes.
- the heatand air-bodied oiticica Oils may be cooked into a varnish much like China wood oil, but the cooking temperature need not, and, preferably, should not, exceed about 460 F. and, in some cases, may be as low as about 400 F.
- China wood oil isusually cooked into a varnish at a temperature in the order ofabout 560 F.
- varnishes made in accordance with our invention are as gas-proof as China wood oil varnishes. Where rosin, modifled phenolic condensation product and like resins are used along with the bodied oiticica oil in a varnish, the films formed are gas-proof, even though the varnish is freefrom driers.
- the gelation characteristics of the heatand air-bodied oiticica oils of our invention and the characteristics of the resulting gel are substantially identical with China wood oil as is evident from the results obtained by subjecting a sample of our bodied oiticica oil to the Worstall heat test,
- untre d oiticica was also subjected tot e Worstall st.
- the heated oil was held at 54 F. for in excess of 15 minutes before what could be termed a solid gel was formed.
- the gel was; soft and sticky and would not crumble, and, in general, I 1
- This varnish cooked to a desirable heavy body. fairly low solid content (46% solids), and good retention of elasticity. Films of this varnish dried quickly forming a water-proof and gas-proof, elastic film which exhibited no tendency to brittle off even after long exposure in the open.
- a similar varnish made With untreated oiticica oil for comparative purposes was low in viscosity and the resultant film was not much better than gloss oil and shortly exhibited a' tendency towards brittling off. 7
- One or more of the driers of the above-illustrative varnish formula may be replaced with other suitable driers or omitted, if desired.
- the limed rosin may be replaced by ester gum, or by kauri gum, sandarac, dammar and like natural resins, or by synthetic resins such as, for example, the
- Lewiso1 320 Beckacite 1101, or by any desired mixture of resins to meet any desired need in a varnish.
- driers therein in the event a completely gas-proof varnish film is desired.
- the mineral spirits may be replaced by other suitable diluents such as V. M. & P. naphtha and the like, or by any desired mixture of diluents.
- 'Another illustrative mixing varnish in accordance with our invention may be prepared as follows: 100 lbs. of ester gum are mixed in a kettle with 25 gals. of treated oiticica oil and are heated to 460 F. and held at that temperature for about minutes. The varnish base is permitted to cool and is then thinned with 55 gals. of mineral spirits, 32 liq. oz. of 10% zinc and 32 liq. oz. of 6% cobalt.
- the bodied oilof our invention may be used for other purposes than for the preparation of varnishes. Thus, it may be used in paints, inks and other coating compositions, and, in general, in lieu of China wood oil wherever China wood oil has been used heretofore.
- the method of treating oiticica oil to cona Worstall test of about 4 to about 7 minutes thereof comprising heating oiticica oil to a temperature in the order of about 350 F. and holding it at about that temperaturefor a period of from about one-half hour to about two hours while bubbling air through the heated oil.
- the method of treating oiticica oil to convert the said oil into a fast-bodying oil having a Worstall test of about 4 to about 7 minutes thereof comprising heatingoiticica oil to a temperature in the order of about 350 F. and holding it at about that temperature for a period of from about one-half hour to about two hours, and simultaneously bubbling air through the heated oil throughout the heating period.
- the method of treating oiticica oil to convert the said oil into a fast-bodying oil having aWorstall test of about 4 to about 7 minutes thereof comprising heating oiticica oil to a temperature in the order of about 350 F. and holding it at about that temperature for a period of from about 30 to 80 minutes and simultaneously bubbling air through the heated oil throughout the heating period.
- the method of treating oiticica oil to convert the said oil into a fast-bodying oil having a Worstall test of about 4 to about 7 minutes thereof comprising heating oiticica oil to a temperature in the order of about 350 F. and holding it at about that temperature for a period of from about 30 to 80 minutes and simultaneously bubbling air through the heated oil throughout the heating period at the rate of about 2 cu. ft. per minute for each lbs. of oil being treated.
- a heatand air-bodied oiticica oil capable of being cooked into a varnish at a temperature ofabout 400 F. to 460 F. and having a Worstall test of about 4 to 7 minutes, said oil having been prepared substantially in accordance with the method of claim 1.
- a heatand air-bodied oiticica oil capable of being cooked into a varnish at a temperature of about'400 F. to 460 F. and having a Worstall test of about 4 minutes, said oil having been prepared substantially in accordance with the method of claim 2.
- a heatand air-bodied oiticica oil capable of being cooked into a varnish at a temperature of about 400 F. to 460 F. and having a Worstall test of about 7 minutes, said oil having been prepared substantially in accordance with the method of claim 2.
- a varnish comprising the cooked reaction product of a resin and a bodied oiticica oil having a Worstall test of about 4 to 7 minutes which has been prepared substantially in accordance with the method of claim 2.
- a varnish comprising the product formed by reacting a bodied oiticica oil having a Worstall test of about 4 to 7 minutes and which has been prepared substantially in accordance with the method of claim 2 with a resin to a pill body at a temperature of about 400 F. to about 460 P.
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- Paints Or Removers (AREA)
Description
acteri'stics of China wood oil.
Patented Nov. 6, 19 15 BODIED OIL AND METHOD Otto Eisenschiml and Gerald Eisenschiml, Chicago, Ill., assignors to Otto Eisenschiml, Bertha J. Eisenschiml, Gerald Eisenschiml, and Rosalie Eisenschiml Gingiss,,doing business as a partnership under name The Scientific Oil Compounding Co., Chicago, Ill.
No Drawing. Application May 10, 1941, Serial No. 392,940
11 Claims.
This invention relates to an improved bodied oiticica oil and to the method of making it; it also relates to varnishes made from this bodied oil.
It has long been a problem in the varnishmaking art to provide a relatively inexpensive substitute for China wood oil. Oiticica oil is a relatively inexpensive drying oil that has been used heretofore in lieu of China wood oil; however, its use has not been very successful because it does not have the desiredquick-bodying char- Varnishes formed from this oil are objectionable from a cost standpoint because they can be thinned only to a 1imited extent with thinners and because the films deposited from these varnishes are nonelastic and brittle off readily from surfaces on which they are formed. In addition, these oiticica oil varnishes do not dry rapidly and do not have certain other desired physical characteristics uch as spread and flow.
We have found that oiticica oil can be treated in accordance with our invention and that the resulting treated oil will body in the kettle atleast as fast as China wood oil and even faster, as desired. Moreover, the treated oil of our invention, when used in a varnish, will produce a film similar to China wood oil in drying and elasticity and which has none of the objectionable brittleness characteristic of films formed from untreated oiticica oil-containing varnishes. In carrying out our invention, oiticica oil is heated in a suitable vessel, for example, a steamjacketed kettle, to a temperature in the order of about 325 F. to 370 F., preferably about 350 F., and held at approximately-that temperature for about /2 hour to 2 hours. Throughout the heating interval, air from any suitable source of supply is introduced into the body of oil from a jet or nozzle or other air distributing device located, preferably, at or adjacent the botttom of the vessel. The effectiveness of contact between the oil and air may be augmented by mechanical agitation, if desired, in which case the kettlemay be provided with an agitator. The amount of air bubbling through the body of heated oil may be varied rather widely to meet any desired requirement in the treated oil; however, for most purposes, the introduction of air at the rate of about 2 cu. ft. per minute for each 100 lbs. of oil is sufficient. This combined heat and air treatment is continued until the desired bodying qualities are obtained. This can be determined experimentally by making gelation tests of samples from the kettle from time to time. In'most instances, the desired bodying qualities are obtained in from about 4 30 to minutes.
The heatand air-bodying treatment of our invention may be carriedout in the presence of catalysts. Examples of suitable catalysts are zinc oleate, zinc resinate, manganese oleate and the like as well as salts of nickel, cobalt, lead, iron and the like, and finely divided metals such as zinc dust and the like.
By operating in accordance with our invention, fast-bodying oiticica oils may be obtained with a Worstall test of about 4 to about 7 minutes, as desired, as compared with China wood oil, the standard, with a Worstall test varying from about 6 to .8 minutes. The heatand air-bodied oiticica Oils may be cooked into a varnish much like China wood oil, but the cooking temperature need not, and, preferably, should not, exceed about 460 F. and, in some cases, may be as low as about 400 F. On the other hand, China wood oil isusually cooked into a varnish at a temperature in the order ofabout 560 F. varnishes made in accordance with our invention are as gas-proof as China wood oil varnishes. Where rosin, modifled phenolic condensation product and like resins are used along with the bodied oiticica oil in a varnish, the films formed are gas-proof, even though the varnish is freefrom driers.
The gelation characteristics of the heatand air-bodied oiticica oils of our invention and the characteristics of the resulting gel are substantially identical with China wood oil as is evident from the results obtained by subjecting a sample of our bodied oiticica oil to the Worstall heat test,
as follows: gms. of oil of our invention was heated in an open container to a temperature of 540 F. in 4 minutes while stirring with a thermometer. The heated oil was held at this temperature. and the stirring was continued until the oil gelled solid. This took slightly more than 4 minutes. As in the case of pure China wood oil which has been similarly treated, but which requires a holding period of from about 6 to 8 minutes for solid gel formation, the resulting gel was dry, non-adherent to a spatula when out and crumbly under the pressure of the spatula without sticking. The cut portions crumbled under pressure like dry bread crumbs. 7
For purposes of comparison, untre d oiticicawas also subjected tot e Worstall st. The heated oil was held at 54 F. for in excess of 15 minutes before what could be termed a solid gel was formed. The gel, however, was; soft and sticky and would not crumble, and, in general, I 1
Limed rosin lbs 100 Treated oiticica oil ga1s 30 Mineral spirits "gals" 60 zinc naphthenate -liq. oz 6% cobalt naphthenate liq. oz 50 6% manganese naphthenate liq. oz 10 The varnish was prepared by cooking the rosin and treated oiticica to a temperature of about 460 F. and holding it at this temperature to a pill body. The driers were added, the varnish cooled, and then thinned with the mineral spirits.
This varnish cooked to a desirable heavy body. fairly low solid content (46% solids), and good retention of elasticity. Films of this varnish dried quickly forming a water-proof and gas-proof, elastic film which exhibited no tendency to brittle off even after long exposure in the open. A similar varnish made With untreated oiticica oil for comparative purposes was low in viscosity and the resultant film was not much better than gloss oil and shortly exhibited a' tendency towards brittling off. 7
One or more of the driers of the above-illustrative varnish formula may be replaced with other suitable driers or omitted, if desired. The limed rosin may be replaced by ester gum, or by kauri gum, sandarac, dammar and like natural resins, or by synthetic resins such as, for example, the
phenolics sold under the trade names Durez,-
Lewiso1 320, Beckacite 1101, or by any desired mixture of resins to meet any desired need in a varnish. In the case of ester gum varnishes in accordance with our invention, it is advisable to use driers therein in the event a completely gas-proof varnish film is desired. The mineral spirits may be replaced by other suitable diluents such as V. M. & P. naphtha and the like, or by any desired mixture of diluents.
'Another illustrative mixing varnish in accordance with our invention may be prepared as follows: 100 lbs. of ester gum are mixed in a kettle with 25 gals. of treated oiticica oil and are heated to 460 F. and held at that temperature for about minutes. The varnish base is permitted to cool and is then thinned with 55 gals. of mineral spirits, 32 liq. oz. of 10% zinc and 32 liq. oz. of 6% cobalt.
The bodied oilof our invention may be used for other purposes than for the preparation of varnishes. Thus, it may be used in paints, inks and other coating compositions, and, in general, in lieu of China wood oil wherever China wood oil has been used heretofore.
We claim:
1. The method of treating oiticica oil to convert the said oil into a fast-bodying oil having a Worstall test of about 4 to about 7 minutes thereof comprising, heating a body of oiticica oil to a temperature in the order of about 350 F. and
holding it at about that temperature for a period of from about one-half hour to about two hours while intimately contacting the heated oil throu hout the body thereof with air.-
2. The method of treating oiticica oil to cona Worstall test of about 4 to about 7 minutes thereof comprising heating oiticica oil to a temperature in the order of about 350 F. and holding it at about that temperaturefor a period of from about one-half hour to about two hours while bubbling air through the heated oil.
3. The method of treating oiticica oil to convert the said oil into a fast-bodying oil having a Worstall test of about 4 to about 7 minutes thereof comprising heatingoiticica oil to a temperature in the order of about 350 F. and holding it at about that temperature for a period of from about one-half hour to about two hours, and simultaneously bubbling air through the heated oil throughout the heating period.
4. The method of treating oiticica oil to convert the said oil into a fast-bodying oil having a Worstall test of about 4 to about 7 minutes thereof comprising heating oiticica oil to a temperature in the order of about 350 F. and holding it at about that temperature for a period of from about 30 to minutes and simultaneously bubbling air through the heated oil.
5. The method of treating oiticica oil to convert the said oil into a fast-bodying oil having aWorstall test of about 4 to about 7 minutes thereof comprising heating oiticica oil to a temperature in the order of about 350 F. and holding it at about that temperature for a period of from about 30 to 80 minutes and simultaneously bubbling air through the heated oil throughout the heating period.
6. The method of treating oiticica oil to convert the said oil into a fast-bodying oil having a Worstall test of about 4 to about 7 minutes thereof comprising heating oiticica oil to a temperature in the order of about 350 F. and holding it at about that temperature for a period of from about 30 to 80 minutes and simultaneously bubbling air through the heated oil throughout the heating period at the rate of about 2 cu. ft. per minute for each lbs. of oil being treated.
7. A heatand air-bodied oiticica oil capable of being cooked into a varnish at a temperature ofabout 400 F. to 460 F. and having a Worstall test of about 4 to 7 minutes, said oil having been prepared substantially in accordance with the method of claim 1.
8. A heatand air-bodied oiticica oil capable of being cooked into a varnish at a temperature of about'400 F. to 460 F. and having a Worstall test of about 4 minutes, said oil having been prepared substantially in accordance with the method of claim 2. Y
9. A heatand air-bodied oiticica oil capable of being cooked into a varnish at a temperature of about 400 F. to 460 F. and having a Worstall test of about 7 minutes, said oil having been prepared substantially in accordance with the method of claim 2.
10. A varnish comprising the cooked reaction product of a resin and a bodied oiticica oil having a Worstall test of about 4 to 7 minutes which has been prepared substantially in accordance with the method of claim 2.
11. A varnish comprising the product formed by reacting a bodied oiticica oil having a Worstall test of about 4 to 7 minutes and which has been prepared substantially in accordance with the method of claim 2 with a resin to a pill body at a temperature of about 400 F. to about 460 P.
OTTO EISENSCHIML. GERALD EISENSCHIML.
CERTIFICATE OF CORREC TI ON Patent No. 2,588,257- November 6, 19145.
OT'IU EISENSCHII'IL, ET AL.
It is. hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, first column, line 68, same page,second columnylines 3, 11, 19-20, 28 and 57, strike out the word "thereof"; and that the said Letters Patent should be readwith this correction therein that the same may conform to the record of the case in the PatentOffice.
Signed and sealed. this 5th day of February, A. D. 19%,
Leslie Frazer (Seal) v v First Assistant Commissioner of Patents.
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US2388257A true US2388257A (en) | 1945-11-06 |
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US2388257D Expired - Lifetime US2388257A (en) | Bodied oil and method |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2822371A (en) * | 1954-10-25 | 1958-02-04 | Ethicon Inc | Bodied 12-keto octadecenoic acid glycerides |
-
0
- US US2388257D patent/US2388257A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2822371A (en) * | 1954-10-25 | 1958-02-04 | Ethicon Inc | Bodied 12-keto octadecenoic acid glycerides |
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