US2957778A - Brightening and stabilizing the color of metal salts of naphthene- and ethylhexanic acids and their solutions - Google Patents
Brightening and stabilizing the color of metal salts of naphthene- and ethylhexanic acids and their solutions Download PDFInfo
- Publication number
- US2957778A US2957778A US715835A US71583558A US2957778A US 2957778 A US2957778 A US 2957778A US 715835 A US715835 A US 715835A US 71583558 A US71583558 A US 71583558A US 2957778 A US2957778 A US 2957778A
- Authority
- US
- United States
- Prior art keywords
- tin
- acids
- salts
- acid
- color
- 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
- 229910052751 metal Inorganic materials 0.000 title claims description 41
- 239000002184 metal Substances 0.000 title claims description 41
- 150000003839 salts Chemical class 0.000 title claims description 32
- 230000000087 stabilizing effect Effects 0.000 title claims description 7
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical class CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 title description 11
- 238000005282 brightening Methods 0.000 title description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 60
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 28
- 150000007513 acids Chemical class 0.000 claims description 16
- 150000002739 metals Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 229910052746 lanthanum Inorganic materials 0.000 claims description 5
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 229910052684 Cerium Inorganic materials 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000008240 homogeneous mixture Substances 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 23
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 125000005608 naphthenic acid group Chemical group 0.000 description 7
- 238000007792 addition Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- -1 for example Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 150000003754 zirconium Chemical class 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Definitions
- naphthenic acids and alpha-ethylhexanic acid, their metal salts and their solutions have a tendency to change color, or more especially, they readily turn dark upon heating. This applies especially to naphthenic acid with a low acid number and to the metal salts of this acid.
- the darkening is partially due to a certain content of suliur in the naphthenic acids, and it has been proposed to eliminate such sulfur, for example by heating the acids in the presence of hydrogen peroxide or another peroxide, although alpha-ethylhexanic acid and naphthenic acids tree from sulfur or having been freed from sulfur are also subject to similar darkening phenomena.
- the darkening interferes with those metal salts which normally have a light color and serve :as driers for making light colors, varnishes or lacquers.
- darkened lead or calcium driers cannot be used as naphthenates or salts of ethylhexanic acid for making especially light colored lacquers.
- other metal salts of the aforesaid acids ior example, zinc, cerium, lanthanum or zirconium salts, and for example, zirconyl salts or salts of similar metals.
- the darkening of metal salts for example, the salts of the aforesaid metals and the darkening of solutions of these metal salts must be attributed to a catalyzed decomposition of the respective acids, a phenomenon which can be inhibited by admixing the metal salts with certain additions.
- the metal salts to be stabilized or their solutions are admixed with tin salts soluble in these solutions. It is especially preferred to use the tin salts of naphthenic acid or alpha-'ethylhexanic acid (octanic acid), but there may also be used the tin salts of other acids, for example, resin acids.
- tin salt sufiices already to obtain a very light colored drier not liable to substantial darkening even when'it is heated for a prolonged time to l20150 C. It is preferred to use ODS-2.0% by weight of tin metal in the form of the corresponding tin salt and calculated upon the solid drier. An amount outside the range indicated above, for example, 0.01% by weight or, for example, 3% by weight of tin salt may, however, also be used with good success.
- the salts of bivalent tin proved somewhat more effective than those of te'travalent tin, but the latter may also successfully be used.
- a color-stabilizing drier of the type described above can be melted without undergoing darkening. This fact is of special importance for the removal of molten material firom a drum.
- the color-stabilizing eifect of the stabilizers used in this invention is indicated in Tables I to III below.
- the color indexes indicate in each particular case how many milligrams of iodine must be dissolved in 1 liter of an aqueous potassium iodide solution to bring about the sanie color impression as with the corresponding metal salt.
- the word heated as used in Table I is intended to mean that the specific specimen was kept for 3 hours at a temperature of 150 C. before the respective color index was determined.
- Table II indicates the color-stabilizing effect of various tin salts in the preparation of solid lead naphthenate (metal content: 31% by weight), of lead naphthenate dissolved in white spirit (metal content: 15.5% by weight), of solid zinc naphthenate (metal content: 12% by weight), and of zinc naphthenate dissolved in white spirit (metal content: 6% by weight).
- the process for stabilizing the light .color of waterinsoluble metal salts of organic acids which comprises preparing a homogeneous mixture of water-insoluble salts of metals selected from the group consisting of tin, lead, zirconium, cerium, lanthanum, zinc and calcium, said mixture containing as essential ingredients (1) a tin salt of an acid selected from the group consisting of naphthenic acids, resinous acids and a-cthyl hexanic acid and (2) a member selected from the group consisting of salts, of one of the aforesaid metals other than tin, of
- naphthenic acids, of ot-ethyl hexanic acid, and mixtures Color-stabilization of lead naphthenate and zinc naphthenate with various tin salts metal Percent color index content, Sn-metal color after heat- Product percent stabilizer on solif index ing for 3 y product hours at weight 160 0.
- unsfahili'mrl 140 180 Lead naphthenate solid 31 bivalent tin salt of alpha-ethylhexanic acid 0.3 35 35 bivalent tin salt of naphthenic acid 0.3 40 40 bivalent tin salt of resinic acid 0. 3 75 75 nrmtahiliwd 15 110 Lead naphthenate dissolved in 15 5 bivalent tin salt of alpha-ethylhexanic acid 0.3 8 13 white spirit.
- a composition comprising a homogeneous mixture of water-insoluble salts of metals selected from the group consisting of tin, lead, zirconium, cerium, lanthanum, zinc and calcium, said mixture containing as essential ingredients (1) a tin salt of an acid selected from the group consisting of naphthenic acids, resinous acids and a-ethyl hexanic acid and (2) a member selected from the group consisting of salts, of one of the aforesaid metals.
- a tin salt of an acid selected from the group consisting of naphthenic acids, resinous acids and a-ethyl hexanic acid
- a member selected from the group consisting of salts, of one of the aforesaid metals Color-stabilizing efiect of tin salts on lead naphthenate dissolved in white spirit (metal content 15.5% by weight) and prepared by two difierent processes Percent Sn-mctal color Preparation of the lead
- tin salt 25 8 spin 5 other than tin, of uaphthenic acids, of a-ethyl hexaznic acid, and mixtures thereof, the tin salt being present in an amount by Weight firom about 0.01 to about 3.0% calculated at metallic tin and referred to the amount of said other salts.
- a composition comprising a homogeneous mixture of Water-insoluble salts of metals selected from the group consisting of tin, lead, zirconium, cen'um, lanthanum, zinc and calcium, said mixture containing as essential ingredients 1) a tin salt of "an aoid selected tfmom the group consisting of naphthenic acids, resinous acids and Jr-ethyl hexanic acid and (2) lead naphthenate, the tin salt being present in an amount by Weight from about 0.01 to about 3.0% calculated as metallic tin and referred to the amount of said other salt.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22413A DE1043554B (de) | 1957-02-22 | 1957-02-22 | Verfahren zum Farbstabilisieren von bei der Faellung hellen Metallsalzen (Trockenstoffen) der Naphthen- und AEthylhexansaeure und deren Loesungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2957778A true US2957778A (en) | 1960-10-25 |
Family
ID=7090432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US715835A Expired - Lifetime US2957778A (en) | 1957-02-22 | 1958-02-17 | Brightening and stabilizing the color of metal salts of naphthene- and ethylhexanic acids and their solutions |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2957778A (en)) |
| DE (1) | DE1043554B (en)) |
| NL (2) | NL112547C (en)) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2236296A (en) * | 1941-03-25 | Westing and dispersing agent |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR837845A (en)) * | 1900-01-01 | |||
| US2139134A (en) * | 1938-12-06 | Liquids such as driers suitable for |
-
0
- NL NL224926D patent/NL224926A/xx unknown
- NL NL112547D patent/NL112547C/xx active
-
1957
- 1957-02-22 DE DEF22413A patent/DE1043554B/de active Pending
-
1958
- 1958-02-17 US US715835A patent/US2957778A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2236296A (en) * | 1941-03-25 | Westing and dispersing agent |
Also Published As
| Publication number | Publication date |
|---|---|
| NL224926A (en)) | |
| DE1043554B (de) | 1958-11-13 |
| NL112547C (en)) |
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