US2360283A - Cobalt siccatives - Google Patents
Cobalt siccatives Download PDFInfo
- Publication number
- US2360283A US2360283A US2360283DA US2360283A US 2360283 A US2360283 A US 2360283A US 2360283D A US2360283D A US 2360283DA US 2360283 A US2360283 A US 2360283A
- Authority
- US
- United States
- Prior art keywords
- cobalt naphthenate
- oil
- naphthenate
- cobalt
- solubility
- 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
- 229910017052 cobalt Inorganic materials 0.000 title 1
- 239000010941 cobalt Substances 0.000 title 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 32
- 239000003921 oil Substances 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 13
- 230000002401 inhibitory effect Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 150000001896 cresols Chemical class 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- -1 aromatic hydroxy compounds Chemical class 0.000 description 4
- 125000005609 naphthenate group Chemical group 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 240000001492 Carallia brachiata Species 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011276 wood tar 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
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F9/00—Compounds to be used as driers, i.e. siccatives
Definitions
- cracked petroleum naphtha cresols l3 13 20 Generally, from 0.05% to 2.0% by weight of the aromatic-hydroxy compounds, based on the cobait naphthenate and intimately admixed with itin either solid or dissolved form, will be found sufficient for the purposes of the invention. Amounts of these compounds as high as by weight will in most cases cause only an inconsiderable improvement over th employment of 2.0% by weight.
- the mono-, di-, triand poly-phenols and their alkyl derivatives such as the methyl, ethyl, propyi, isopropyl, butyl, isobutyi and higher homologues, the cresols.
- propionyl, butyryl, valeryl and higher homologues thereof may be employed in the practice of the invention.
- compositions of the invention intimate admixture of the stabilizing agent with the cobalt naphthenate is essential. This may be accomplished by dissolving the requisite amount of the agent in a solvent and dispersing it on the surface of the solid particles of cobalt naphthenate; the evaporation of the solvent leaves a residual quantity of the agent in sufliciently widely dispersed form.
- the agent may merely be incorporated in the solvent itself; or the inhibitory substance may be added during the course of the formation of the metal naphthenate salt itself, so long as the progress of the formation allows it to accompany the naphthenate and remain permanently and intimately associated therewith.
- the principal desideratum here is that the aromatic hydroxy compound may be allowed to function in the manner intended for the practice of the invention, namely, in sufficient amount and in sufficiently intimate association with the cobalt naphthenate to enable it to inhibit or entirely prevent the deteriorations in oil-solubility and color referred to herein above.
- a cobalt naphthenate siccative stabilized against color change and decrease in oil solubility comprising cobalt naphthenate and an inhibiting agent comprising a cresol, said cobalt naphthenate without said inhibiting agent being subject to color change and decrease in oil solubility, and said inhibiting agent being mixed with said cobalt naphthenate in a proportion suflicient to inhibit color change and decrease in oil solubility of said cobalt naphthenate.
- a cobalt naphthenate siccative stabilized against color change and decrease in oil solubility comprising cobalt naphthenate and between 0.05% and 5.0% of its weight of a cresol.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Description
Patented Oct. 10, 1944 STATES comm srooa'rrvas John T. Rutherford, Berkeley, Calii'., assignor to Standard Oil Company or California, San Francisco, Calii.. a corporation of Delaware No Drawing. Application August 27, 1938, Serial No. 227,178
i'jlaims. (Cl. 260-439) nishes, ink oils and the like as a drying agent.
Prior to its incorporation in paints, varnishes and the like, cobalt naphthenate is often dispensed and stored as an essentially pure dry solid, sometimes in massive and sometimes in finely pulverized form. Upon storage, and particularly upon exposure to air, cobalt naphthenate deteriorates to such an extent that considerable proportions become insoluble in oil, whether by the formation of oxides or of oilinsoluble salts is not exactly understood. This degradation of cobalt naphthenate, which in its normal state is completely oil-soluble, is manitested by a progressive change in color, from an original deep blue-purple to a green and finally to a brown. As these color changes take place, the naphthenate becomes progressively less soluble in petroleum thinners and drying oils, rendering it useless as a paint drier; for example, a finely pulverized cobalt naphthenate may become entirely insoluble in oil and thinners upon the lapse of some months, when exposed to the air.
Likewise prior to its incorporation in paints,
or less extent, which deterioration is likewise by the preponderant amounts of vehicles, pig' ment, etc. with which it is then associated. It will accordingly be understood that the effects described, and the invention here disclosed, are concerned entirely with the drier itself, in solid or in dissolved or so-called liquid form, before incorporation in the preponderant amounts 01' vehicles and pigments which together constitute an ultimate paint, varnish, ink oil or the like type of composition.
It has now been found that the intimate admixture of a very small amount of certain in-' hibiting agents will remarkably postpone the above deterioration or degradation, that in the presence of such agents the cobalt naphthenate retains its original complete solubility in thinness and oils, and that the color changes which normally accompany the usual progressive deterioration do not manifest themselves with their normal rapidity. In general, the agents found to stabilize cobalt naphthenate against the untoward degrading effects here noticed are P the aromatic hydroxy compounds, and derivatives of aromatic-hydroxy compounds, as more fully exemplified herein below.
It is a purpose of this invention to disclose and provide cobalt naphthenate compositions, as solids and as solutions in oils and thinners, which do not deteriorate to form oil-insoluble substances at the normal rates at which such deterioration occurs, and to disclose and provide methods by which such stabilization may be accomplished. It is a further object of this invention to disclose and provide cobalt naphthenate. compositions, in dissolved as well as in 'undissolved form, which contain aromatic-hydroxy compounds in suflicient amount and in sufficient intimacy of association to effect these stabilizations against colorand solubility-alterations. I
In exemplification of the methods and compositions of the invention:
Inasmuch as the initiation and progress of oil-insolubility of cobalt naphthenate have been found to be manifested through accompanying changes in color, it has been found convenient to measure the effectiveness of the inhibiting agents by the observation of such color changes, for example in the following manner: Ordinary analytical filter paper is dipped in a solution of the cobalt naphthenate in a volatile mineral thinner, or some drops of such a solution are allowed to fall upon such a porous paper. The thinner rapidly evaporates, leaving a residue of very finely divided solid cobalt naphthenate of extensive surface area. The paper is exposed to the air and is observed periodically for such color changes as may appear in the solid cobalt naphthenate particles, such color changes taking the following course: purple (original), greenish traces, green, dark green, brown (ultimate). Ordinarily the progress toward dark green is suflicient to ascertain the efiectiveness of the Number of days before first appearance o1' Greenish Dark traces Green green Cobalt naphthenate alone 5 7 11 +1.0 pyrogallol 20 20 20 +0.1 240-300 C. wood tar distillate cresols 20 20 20 +10% ISO-205 0. cracked petroleum naphtha cresols l3 13 20 Generally, from 0.05% to 2.0% by weight of the aromatic-hydroxy compounds, based on the cobait naphthenate and intimately admixed with itin either solid or dissolved form, will be found sufficient for the purposes of the invention. Amounts of these compounds as high as by weight will in most cases cause only an inconsiderable improvement over th employment of 2.0% by weight.
The mono-, di-, triand poly-phenols and their alkyl derivatives, such as the methyl, ethyl, propyi, isopropyl, butyl, isobutyi and higher homologues, the cresols. hydroquinone, phloroglucinol, pyrocatechol, pyrogalloi, resorcinol and the naphthols, especially beta-naphthol, as well as the acyl derivatives thereof, such as the acetyl,
propionyl, butyryl, valeryl and higher homologues thereof, may be employed in the practice of the invention.
In preparing the compositions of the invention, intimate admixture of the stabilizing agent with the cobalt naphthenate is essential. This may be accomplished by dissolving the requisite amount of the agent in a solvent and dispersing it on the surface of the solid particles of cobalt naphthenate; the evaporation of the solvent leaves a residual quantity of the agent in sufliciently widely dispersed form. In the event that th cobalt naphthenate is manufactured in liquid form, that is, in solution in a thinner or solvent, the agent may merely be incorporated in the solvent itself; or the inhibitory substance may be added during the course of the formation of the metal naphthenate salt itself, so long as the progress of the formation allows it to accompany the naphthenate and remain permanently and intimately associated therewith. The principal desideratum here is that the aromatic hydroxy compound may be allowed to function in the manner intended for the practice of the invention, namely, in sufficient amount and in sufficiently intimate association with the cobalt naphthenate to enable it to inhibit or entirely prevent the deteriorations in oil-solubility and color referred to herein above.
Certain obvious modifications of the invention as above described will be apparent to one skilled in the art, and it will be understood that while the character of the invention and numerous illustrative examples of its practice have been described in detail, this has been done by way of illustration only and with the intention that no limitation be imposed upon the invention, which includes all such changes and modifications as come within the scope of the appended claims,
I claim:
1. A cobalt naphthenate siccative stabilized against color change and decrease in oil solubility comprising cobalt naphthenate and an inhibiting agent comprising a cresol, said cobalt naphthenate without said inhibiting agent being subject to color change and decrease in oil solubility, and said inhibiting agent being mixed with said cobalt naphthenate in a proportion suflicient to inhibit color change and decrease in oil solubility of said cobalt naphthenate.
2. A cobalt naphthenate slccative stabilized against color change and decrease in oil solubility comprising cobalt naphthenate and an inhibiting agent comprising -205 C. cracked petroleum naphtha cresols, said cobalt naphthenate without said inhibiting agent being sub ject to color change and decrease in oil solubility, and said inhibiting agent being intimately mixed with said cobalt naphthenate in a proportion sufficient to inhibit color change and decrease in oil solubility thereof.
3. A cobalt naphthenate siccative stabilized against color change and decrease in oil solubility comprising cobalt naphthenate and between 0.05% and 5.0% of its weight of a cresol.
4. A cobalt naphthenate siccative stabilized against color change and decrease in oil .solubility comprising cobalt naphthenate and between 0.05% and 5.0% of its weight of cracked petroleum naphtha cresols.
5. A cobalt naphthenate siccative stabilized against color change and decrease in oil solubility comprising cobalt naphthenate and between 0.05% and 5.0% of its weight of a 180-205 C. fraction from cracked petroleum naphtha cresols.
JOHN T. RUTHERFORD.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2360283A true US2360283A (en) | 1944-10-10 |
Family
ID=3434054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2360283D Expired - Lifetime US2360283A (en) | Cobalt siccatives |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2360283A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2600571A (en) * | 1947-10-14 | 1952-06-17 | Du Pont | Butadiene-cobalt carbonyl hydride adduct |
| US2894849A (en) * | 1957-05-20 | 1959-07-14 | Sherwin Williams Co | Alpha, gamma diketones in combination with metallo-organic driers as drying accelerators for siccative coatings |
| US2914417A (en) * | 1956-08-07 | 1959-11-24 | Nat Aluminate Corp | Treatment of hydrocarbon liquids |
| US2950172A (en) * | 1956-11-23 | 1960-08-23 | Int Nickel Co | Production of cobaltous hydroxide |
-
0
- US US2360283D patent/US2360283A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2600571A (en) * | 1947-10-14 | 1952-06-17 | Du Pont | Butadiene-cobalt carbonyl hydride adduct |
| US2914417A (en) * | 1956-08-07 | 1959-11-24 | Nat Aluminate Corp | Treatment of hydrocarbon liquids |
| US2950172A (en) * | 1956-11-23 | 1960-08-23 | Int Nickel Co | Production of cobaltous hydroxide |
| US2894849A (en) * | 1957-05-20 | 1959-07-14 | Sherwin Williams Co | Alpha, gamma diketones in combination with metallo-organic driers as drying accelerators for siccative coatings |
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