US1634359A - Coating composition - Google Patents
Coating composition Download PDFInfo
- Publication number
- US1634359A US1634359A US41880A US4188025A US1634359A US 1634359 A US1634359 A US 1634359A US 41880 A US41880 A US 41880A US 4188025 A US4188025 A US 4188025A US 1634359 A US1634359 A US 1634359A
- Authority
- US
- United States
- Prior art keywords
- oil
- glycerol
- heating
- mixture
- coating composition
- 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
- 239000008199 coating composition Substances 0.000 title description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 73
- 239000003921 oil Substances 0.000 description 36
- 235000019198 oils Nutrition 0.000 description 36
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 29
- 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 29
- 238000010438 heat treatment Methods 0.000 description 29
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 27
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000002383 tung oil Substances 0.000 description 13
- 235000015112 vegetable and seed oil Nutrition 0.000 description 13
- 239000008158 vegetable oil Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 241000350151 Guibourtia demeusei Species 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 125000005456 glyceride group Chemical group 0.000 description 8
- 239000004859 Copal Substances 0.000 description 7
- 241000782205 Guibourtia conjugata Species 0.000 description 7
- 210000003298 dental enamel Anatomy 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000004020 conductor Substances 0.000 description 4
- 238000007865 diluting Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920001800 Shellac Polymers 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- -1 glycerol ester Chemical class 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
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 235000013874 shellac Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 240000000972 Agathis dammara Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002023 wood Substances 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
- Patented .luly 5, 1927 Patented .luly 5, 1927.
- This invention relates to coating compositions, and its object is to produce a liquid coating composition which may be readily applied to an article and baked thereon to 6 form a hard, tough, flexible and durable coating.
- polymerized vegetable oil is used as the basis of a liquid coating com- 30 osition.
- the vegetable oils which have V een found most suitable are those, such as tung oil and castor oil, which have the properties of polymerizing and thereafter gelatinizing when heated.
- Such oils give the bestresults when polymerized to a state just short of gelatinization.
- the oil may be heated alone for a suitable length of time and then suddenly cooled by the addition of a substance,
- rosin oil in a cold state.
- Vegetable oils prepared in this way may be spread upon a metallic article and baked thereon to form a hard, flexible, insulating enamel.
- a liquid coating composition 85 prepared from vegetable oils alone is slow aking, the polymerized oil is mixed with certain substances which will decrease the time required to bake it on a metallic article and which will, for this reason, considerably all reduce the cost of coating such an article.
- llhe substances which have been found most satisfactory for this purpose are certain resin glycerides.
- a resin such as Congo copal might be used, but it has been found preferable to use the glyceride of such a. resin both because it may be transformed by heat into a hard substance at a temperature similar to that at which vegetable oils are thus transformed and because the glycerol converts the acid bodies of the resin into substances which are more inert chemically.
- glycerides have a tendency when heat treated to gelatinize in the same manner that certain vege- 1925. Serial 1m, 415w.
- the mixture should be heated over a period 9 order that the resulting composition produce a smooth coating when 'ap lied to and baked on the metallic article. T e composition is then spread on the metallic article and baked.
- Such a composition bakes rapidl at a temperature, similar to that at whic vegetable oil hardens, and forms an enamel which is hard enough to withstand the treatment to which electrical conductors are normally subjected, which has a toughness greater than that of an enamel formed from vegetable oil alone, which is so flexible that a wirecoated therewith may be sharply bent without cracking the enamel, and which has good insulating properties. Furthermore,
- this enamel is very resistant to the solventaction of the benzol or carbon tetrachloride contained in cleaning fluids commonly used upon the enameled conductors, or the linseed oil in certain varnishes with which enameled conductors are often coated, or the denatured alcohol used in shellacs of. the resin-rosin oil combinations, or of the paraflin used in the melted moisture-proofing compositions with which coils of enameled wire are often impregnated, or of the gasoline or benzene contained in various liquids which are likely to come in contact with enameled conductors.
- Tung oil (Chinese wood oil) any of the followin ways:
- the glycerol performs the double function of delaying gelatinization of the oil in case it is overheated before the addition of the rosin oil, and of rendering the coating composition less acid, and hence making it capable of producing a baked coating which is very inert to solvents.
- Tung oil is heated at a temperature not to exceed 220 C. to a point approaching gelatinization and then mixed with cold rosin oil.
- the glyceride of Congo copal may be 4 formed in any of the following ways:
- the glycerol may be added at once.
- the ratio of rosin oil to copal should be maintained at not less than two to one.
- the resultant mixture is heated for about six hours when a suitable proportion of volatile solvent, such as benzene or high-flashnaphtha, is added.
- This composition may be applied to the article to be coated and is baked thereon at a temperature of about 300 C. to drive off the benzene or naphtha, any excess glycerol, and the rosin oil, and to harden the coating. If a thicker coating is desired, the application and the baking process may be repeated as often as necessary.
- Castor oil, corn oil, soy bean oil, rape-seed oil, sesame oil, cottonseed oil and peanut oil may be used in place of either tung oil or the linseed oil and either of these oils may replace the other.
- Other resin oils may be used in place of the rosin oil.
- Manila copal and shellac are examples of other resins which will form gelatinizable esters with glycerol and are adapted for use in this invention.
- the coating composition in this invention may be applied in thicker coatin s than the ordinary enamels and yet pr uce a smooth even product.
- the process of producing a liquid coating composition which comprises heating gelatinizable vegetable oil, adding cold rosin oil thereto, m'xing therewith a substance which will gi e a quick baking (quality to the liquid coating composition, an heating the mixture.
- the process of producing a liquid coating composition w ichcomprises adding g1 cerol to neutralize the acid bodies of a substance having a quick baking quality, heatin gelatinizable vegetable oil, and ad ing co d rosin oil thereto, mixing the products so formed, and heating the resulting mixture.
- T e process of producing a liquid coating composition which comprises heating resin and rosin oil, adding thereto suflicient glycerol to produce a glycerol ester of said resin having a low acid number and heating the mixture, heating gelatinizable vegetable oil and adding rosin oil thereto, mixing the products so formed, and heating the resulting mass.
- the process of producing an insulating enamel which comprises heating gelatinizable vegetable oil, adding thereto a substance which will arrest the gelatinization thereof, adding glycerol to a mixture of rosin oil and resin and applying heat thereto; mixing the products so formed, heating the mixture, diluting the resulting mass with a volatile solvent, applying the diluted mass to the surface to be coated, and baking it thereon.
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)
- Paints Or Removers (AREA)
Description
Patented .luly 5, 1927.
UNITED STATES 1,634,359 PATENT OFFICE.
cant. I). nocxnn, or men omen, new .rnRsnY, ABSIGNOB 'ro wns'rnnn' nnncrmc comm, moonronarnn, or new You, 1:, Y., a conromrron or raw YORK.
COATING COMPOSITION.
In Drawing. Original application filed December 18, 1928, Serial Io. 680,343. Divided and this application filed July 6,
This invention relates to coating compositions, and its object is to produce a liquid coating composition which may be readily applied to an article and baked thereon to 6 form a hard, tough, flexible and durable coating.
In particular, it is desired to produce a.
In accordance with the general features of the invention, polymerized vegetable oil is used as the basis of a liquid coating com- 30 osition. The vegetable oils .which have V een found most suitable are those, such as tung oil and castor oil, which have the properties of polymerizing and thereafter gelatinizing when heated. Such oils give the bestresults when polymerized to a state just short of gelatinization. To realize this state of gelatinization, the oil may be heated alone for a suitable length of time and then suddenly cooled by the addition of a substance,
as such as rosin oil, in a cold state. Vegetable oils prepared in this way may be spread upon a metallic article and baked thereon to form a hard, flexible, insulating enamel. Inasmuch as a liquid coating composition 85 prepared from vegetable oils alone is slow aking, the polymerized oil is mixed with certain substances which will decrease the time required to bake it on a metallic article and which will, for this reason, considerably all reduce the cost of coating such an article. llhe substances which have been found most satisfactory for this purpose are certain resin glycerides.
A resin, such as Congo copal might be used, but it has been found preferable to use the glyceride of such a. resin both because it may be transformed by heat into a hard substance at a temperature similar to that at which vegetable oils are thus transformed and because the glycerol converts the acid bodies of the resin into substances which are more inert chemically. As such glycerides have a tendency when heat treated to gelatinize in the same manner that certain vege- 1925. Serial 1m, 415w.
make the coating less flexible when heated to.
a degree at which it has the necessary inertness to solvents.
After the addition of the glyceride, the mixture should be heated over a period 9 order that the resulting composition produce a smooth coating when 'ap lied to and baked on the metallic article. T e composition is then spread on the metallic article and baked.
Such a composition bakes rapidl at a temperature, similar to that at whic vegetable oil hardens, and forms an enamel which is hard enough to withstand the treatment to which electrical conductors are normally subjected, which has a toughness greater than that of an enamel formed from vegetable oil alone, which is so flexible that a wirecoated therewith may be sharply bent without cracking the enamel, and which has good insulating properties. Furthermore,
this enamel is very resistant to the solventaction of the benzol or carbon tetrachloride contained in cleaning fluids commonly used upon the enameled conductors, or the linseed oil in certain varnishes with which enameled conductors are often coated, or the denatured alcohol used in shellacs of. the resin-rosin oil combinations, or of the paraflin used in the melted moisture-proofing compositions with which coils of enameled wire are often impregnated, or of the gasoline or benzene contained in various liquids which are likely to come in contact with enameled conductors.
Certain examples illustrating the above processes are given below to enable the invention to be more readil practiced. When proportions are given ey are by weight unless otherwise stated.
Tung oil (Chinese wood oil) any of the followin ways:
(cl One part of glycerol is added to is treated in f 70 time, and solventsfiadded, if necessary, in
' cooled by the addition of twelve parts of cold rosin oil having an acid number of five or less.
.In this example,the glycerol performs the double function of delaying gelatinization of the oil in case it is overheated before the addition of the rosin oil, and of rendering the coating composition less acid, and hence making it capable of producing a baked coating which is very inert to solvents.
(b) Tung oil is heated at a temperature not to exceed 220 C. to a point approaching gelatinization and then mixed with cold rosin oil. 1
The glyceride of Congo copal may be 4 formed in any of the following ways:
(a') Two or more parts of rosin oil (preferably having a hi h boiling point) are added to one part of ongo copal and the mix ture heated at between 275 C. and300 C. for two hours or until the copal is entirely fused. One gallon of glycerol for each fourteen pounds of Congo copal used is then added to the mixture and the temperature maintained at between 280 C. and 300 C. for about one hour. At the completion of this heating the mass will still contain a considerable amount of uncombined copal and the above treatment with glycerol is repeated until the acid number of the mixture is re-- duced to about ten. If apparatus is used w ich will prevent to a certain extent the volatilization of the glycerol, all the glycerol may be added at once. During the treatment with glycerol, the ratio of rosin oil to copal should be maintained at not less than two to one.
(6') Con o copal is fused until it has lost .20 to 35% 0 its weight. To one part of this fused copal is added two parts of rosin oil. Glycerol is then added and the process continued in either of the ways indicated in a above. i
(0') Congo copal is fused with an equal portion of rosin, the resultant product heated with glycerol preferably in the presence of rosin oil'and the process continued as in a above.
(d') Three parts of Congo copal are fused as described in my Patent 1,422,861, on July 18, 1922 with two parts of those fatt acids derivable from tung oil by saponi cation. Suflicientglycerol to neutralize both the resin and the atty acid is then added and the mixture heated preferably in the presence of rosin oil in the manner described in a above. A certain amount of tung oil is formed from the glycerol and the tung oil fatty acids and is then polymerized by the heating.
of resin glyceride as prepared in either (a'), 1 i
Three parts of of the mixture of resin glyceride and polymerized tung oil prepared as in (d).
The resultant mixture is heated for about six hours when a suitable proportion of volatile solvent, such as benzene or high-flashnaphtha, is added. This composition may be applied to the article to be coated and is baked thereon at a temperature of about 300 C. to drive off the benzene or naphtha, any excess glycerol, and the rosin oil, and to harden the coating. If a thicker coating is desired, the application and the baking process may be repeated as often as necessary.-
treated tung oil to one part Any substance which will perform a like I function should be considered as the equivalentof any of the substances mentioned in the specific examples described above.
Castor oil, corn oil, soy bean oil, rape-seed oil, sesame oil, cottonseed oil and peanut oil, for instance, may be used in place of either tung oil or the linseed oil and either of these oils may replace the other. Other resin oils may be used in place of the rosin oil.
Manila copal and shellac are examples of other resins which will form gelatinizable esters with glycerol and are adapted for use in this invention.
Actual practice has shown that the coating composition in this invention may be applied in thicker coatin s than the ordinary enamels and yet pr uce a smooth even product.
What is claimed is:
, 1. The process of producing a liquid coating composition which comprises heating gelatinizable vegetable oil, adding cold rosin oil thereto, m'xing therewith a substance which will gi e a quick baking (quality to the liquid coating composition, an heating the mixture. 2. The process of producing a liquid coating composition w ichcomprises adding g1 cerol to neutralize the acid bodies of a substance having a quick baking quality, heatin gelatinizable vegetable oil, and ad ing co d rosin oil thereto, mixing the products so formed, and heating the resulting mixture.
3. The process of producing a liquid coating composition which comprises heating ge atinizable vegetable oil and adding a rosin oil thereao; heating resin and rosin oil, adding glycerol thereto and heating the mixture; mixing the products so formed, and heatin the mixture.
4. T e process of producing a liquid coating composition which comprises heating resin and rosin oil, adding thereto suflicient glycerol to produce a glycerol ester of said resin having a low acid number and heating the mixture, heating gelatinizable vegetable oil and adding rosin oil thereto, mixing the products so formed, and heating the resulting mass.
5. The process of producing an insulating enamel which comprises heating gelatinizable vegetable oil, adding thereto a substance which will arrest the gelatinization thereof, adding glycerol to a mixture of rosin oil and resin and applying heat thereto; mixing the products so formed, heating the mixture, diluting the resulting mass with a volatile solvent, applying the diluted mass to the surface to be coated, and baking it thereon.
6. The process of producing a liquid coating composition which comprises heating vegetable oil, adding cold rosin oil thereto, forming a gelatinizable glycerol ester of y resin in the presence of a substancewhich will prevent the gelatinization of said ester, mixing the products so formed, heating the mixture, and adding a volatile solvent.
7. The process of forming a liquid coating composition which comprises heating vegetableioil and adding cold rosin oil there'- to, heating a mixture of resin, rosin oil and.
glycerol, mixing the products so formed,
heating the resulting mixture, and diluting with a volatile solvent.
8. The process of producing a liquid coating composition which comprises heating tung oil and adding rosin oil thereto, heating glycerol with a mixture of Congo copal and rosin oil, mixing the products so formed, and heating the mixture.
9. The process of producing a liquid coating composition which comprises heating tung oil with glycerol and adding rosin oil thereto, heating glycerol with a mixture of Congo copal and rosin oil, mixing the products so formed, and heating the mixture.'
10. The process of producing a liquid coating composition which comprises heating tung oil with a smaller amount of glycerol, adding rosin oil thereto, and mixing therewith resin glyceride.
11. The process of producing a liquid coating composition which comprises fusing Con o copal, adding glycerol thereto, and heating to esterity the Congo copal in the presence of at least two times its weight of rosin oil, heating tung oil with a smaller quantity of glycerol, adding cold rosin oil thereto, mixing this product with the Congo copal ester mixture, heating the resulting mixture, and diluting the heated mass.
In witness whereof, I hereunto subscribe my name this 3rd da of July A. D., 1925.
- CZKRL D. HOCKER.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US41880A US1634359A (en) | 1923-12-13 | 1925-07-06 | Coating composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US680343A US1638579A (en) | 1923-12-13 | 1923-12-13 | Coating compositions |
US41880A US1634359A (en) | 1923-12-13 | 1925-07-06 | Coating composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US1634359A true US1634359A (en) | 1927-07-05 |
Family
ID=26718650
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US41880A Expired - Lifetime US1634359A (en) | 1923-12-13 | 1925-07-06 | Coating composition |
Country Status (1)
Country | Link |
---|---|
US (1) | US1634359A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2829064A (en) * | 1955-10-04 | 1958-04-01 | Jr Lucien L Hopper | Process of preparing tung oil varnish resins |
-
1925
- 1925-07-06 US US41880A patent/US1634359A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2829064A (en) * | 1955-10-04 | 1958-04-01 | Jr Lucien L Hopper | Process of preparing tung oil varnish resins |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US1975246A (en) | Alkyd resin | |
US1893874A (en) | Lester v | |
US1634359A (en) | Coating composition | |
US2191581A (en) | Insulating resinous compositions and electrical conductors coated with the same | |
US1638579A (en) | Coating compositions | |
US2216234A (en) | Enamel composition | |
US1893611A (en) | Wrinkled finish coating | |
US2294703A (en) | Wrinkle finish composition and method of making | |
US2326120A (en) | Metal coating composition | |
US2344189A (en) | Wrinkling enamel and method of making | |
US2441105A (en) | Coating composition | |
US1954835A (en) | Crystallizing varnish | |
US1977932A (en) | Coating composition | |
US2407623A (en) | Modified linseed oil wrinkle finish | |
US2248965A (en) | Bajkingoil | |
US1838072A (en) | Reaction products of cashew nut shell oil and processes therefor | |
US2373177A (en) | Wrinkle finish drying compositions | |
US2142833A (en) | Resinous composition and method of making the same | |
US2459176A (en) | Process of preparing oil acid modified alkyd material | |
US2394500A (en) | Modified wrinkle finish | |
US2460485A (en) | Flexible wrinkle coated material and method of producing same | |
US1422861A (en) | Liquid coating composition | |
US2319507A (en) | Composition containing wood oil ob | |
US2358623A (en) | Coating composition | |
US2063669A (en) | Asphalt paint |