US2456824A - Oil-soluble drier metal salt compositions - Google Patents
Oil-soluble drier metal salt compositions Download PDFInfo
- Publication number
- US2456824A US2456824A US682586A US68258646A US2456824A US 2456824 A US2456824 A US 2456824A US 682586 A US682586 A US 682586A US 68258646 A US68258646 A US 68258646A US 2456824 A US2456824 A US 2456824A
- Authority
- US
- United States
- Prior art keywords
- oil
- drier
- metal
- viscosity
- acid
- 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 description 28
- 239000002184 metal Substances 0.000 title description 28
- 150000003839 salts Chemical class 0.000 title description 25
- 239000000203 mixture Substances 0.000 title description 24
- 239000000243 solution Substances 0.000 description 34
- 239000002253 acid Substances 0.000 description 26
- 229910019142 PO4 Inorganic materials 0.000 description 16
- 235000021317 phosphate Nutrition 0.000 description 16
- 239000000944 linseed oil Substances 0.000 description 15
- 235000021388 linseed oil Nutrition 0.000 description 15
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 12
- 239000010452 phosphate Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000003513 alkali Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
- SGGOJYZMTYGPCH-UHFFFAOYSA-L 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 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 10
- 239000011707 mineral Substances 0.000 description 10
- 235000010755 mineral Nutrition 0.000 description 10
- 235000015096 spirit Nutrition 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- NVTPMUHPCAUGCB-UHFFFAOYSA-N pentyl dihydrogen phosphate Chemical compound CCCCCOP(O)(O)=O NVTPMUHPCAUGCB-UHFFFAOYSA-N 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 7
- 239000010941 cobalt Substances 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- 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 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 6
- 239000011133 lead Substances 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 235000005985 organic acids Nutrition 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 229910052748 manganese Inorganic materials 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- IIGAELMXVLEZPM-GRVYQHKQSA-L cobalt(2+);(9z,12z)-octadeca-9,12-dienoate Chemical compound [Co+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O IIGAELMXVLEZPM-GRVYQHKQSA-L 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- -1 cat-v alysts Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 235000006173 Larrea tridentata Nutrition 0.000 description 2
- 244000073231 Larrea tridentata Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 229940120693 copper naphthenate Drugs 0.000 description 2
- SVOAENZIOKPANY-CVBJKYQLSA-L copper;(z)-octadec-9-enoate Chemical compound [Cu+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O SVOAENZIOKPANY-CVBJKYQLSA-L 0.000 description 2
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 2
- 229960002126 creosote Drugs 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000005608 naphthenic acid group Chemical class 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 241000235319 Havinthus Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Chemical class 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 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 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
- 150000001868 cobalt Chemical class 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- MAQCMFOLVVSLLK-UHFFFAOYSA-N methyl 4-(bromomethyl)pyridine-2-carboxylate Chemical compound COC(=O)C1=CC(CBr)=CC=N1 MAQCMFOLVVSLLK-UHFFFAOYSA-N 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000003784 tall oil Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/12—Straight chain carboxylic acids containing eighteen carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/18—Tall oil acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
Definitions
- This invention relates to oil-soluble metal salt compositions useful in several arts for various purposes, such, for example, as in connection with paint and varnish driers, bodying agents, cat-v alysts, lubricant additives, etc.
- the oil-soluble salts of diverse organic acids are in use for many different purposes.
- the drying metal salts that is, principally lead, cobalt, manganese, iron, zinc and nickel salts of certain organic acids; for example, naphthenic acids, tall oil acids, rosin acids, linseed acids, 2-ethylhexoic acid, etc.
- naphthenic acids for example, tall oil acids, rosin acids, linseed acids, 2-ethylhexoic acid, etc.
- the lead salts of certain acids such as naphthenic acids, are employed not only as driers, but also to impart certain desirable characteristics to lubricants.
- Heavy metal and alkali earth metal salts are generally water-insoluble. Their commercial utility depends upon their ability to dissolve in and to be stable in the organic solvents and vehicles for which they are intended. For example, in the case of cobalt, manganese and lead driers they are usually employed in compositions containing drying oils such as linseed oil. In order that they may function properly it is necessary that they be soluble in such oils and many other types of vehicles used in paints, varnishes and printing inks. Similarly a copper salt, intended for use in fungicides, should be soluble in certain organic vehicles, such as creosote oils, with which it is often associated in fungicidal compositions. Zinc salts, such as zinc naththenate, are employed commercially as wetting agents in paints and varnishes. For such application it is desirable that these salts be 301- uble in the vehicles of such compositions.
- the metal salts are sometimes employed in solid form; i. e., in the absence of a solvent, but more often they are employed in the form of concentrated liquid solvent solutions.
- serious difficulties have been experienced in the commercial use of the above described metal salts because they lack the necessary element of solubility. Equally serious troubles are experienced in the preparation of such metal salts and their solutions.
- metal salts are often only incompletely soluble in solvents which are intended for the preparation of their concentrated solutions, as Well as in the ultimate vehicles and compositions for which they are intended.
- the solvent solutions generally contain, for the purpose of minimizing their tendency towards sludging and their lack of solubility, relatively high proportions of organic acids. They may carry as much as 25% of free acids for this purpose. This means that a relatively high amount of extraneous matter is introduced along with the active principal. It also means that, were it not for the presence of such free acid, the concentration of the metal salt in such solutions would be increased.
- alkyl acid phosphates greatly reduce the viscosity of solutions of oil-soluble metal salts and greatly improve the stability and solubility of such solutions. Furthermore, they make it possible to effect considerable economies in the preparation of such compositions.
- stabilizing agents are of very low vapor pressure and thus will remain permanently associated in the compositions in which they are incorporated.
- the amount of stabilizing agent needed is relatively small, as low as 25% per total weight of the heavy metal salt solutions having effected markedchanges, but it may be found desirable in some cases to use considerably higher percentages of such stabilizing agents. Generally speaking, we have found that from 1% to 3% produces commercially satisfactory results.
- alkyl acid phosphates of this invention are compounds with the general formula R-H2PO4 or R-R-HPO4, as well as combinations of both.
- R" represents an alkyl radical.
- EXAMPLE 1 In this example a manganese naphthenate has been prepared without the agent of this invention, but employing approximately of free naphthenic acid so as to make the product commercially acceptable. mineral spirits solution of manganese naphthenate carrying 6% manganese metal.
- the mixture After agitation, the mixture is allowed to stratify into an upper mineral spirits layer containing manganese naphthenate and a lower aqueous layer. The latter is run off and the uper mineral spirits layer is dried in vacuo. The final dry product is adjusted with mineral sprits so that the manganese content is 6%.
- the product of this example represents the best commercial grade that could be produced prior to this invention.
- EXAMPLE 3 This example shows the addition of butyl acid phosphate to an already prepared manganese naphthenate drier solution carrying 6% manganese metal.
- butyl acid phosphate is incorporated into a commercial 6% manganese naphthenate liquid drier.
- the commercial product is considerably improved. Its viscosity is reduced from 300 cps. to 100 cps.
- the alkali refined linseed oil solubility which was fair becomes excellent.
- the original product is rendered stable to heating; that is, the viscosity (100 cps.) and the alkali refined linseed oil solubility (excellent), remain unaffected after heating at 320 F. for three hours.
- EXAMPLE4 This example shows the addition of octyl acid phosphate to an already prepared manganese naphthenate drier solution carrying 6% manganese metal.
- octyl acid phosphate 2.5% octyl acid phosphate is incorporated into a commercial 6% manganese naphthenate liquid drier.
- the commercial product is considerably improved. Its viscosity is reduced from 300 cps. to 100 cps.
- the alkali refined linseed oil solubility which was fair, becomes excellent.
- the original product is rendered stable to heating; that is, the viscosity (100 cps.) and the alkali refined linseed oil solubility (excellent), remain unaffected after heating at 320 F. for 3 hours.
- EXAMPLE 5 This example shows the use of propyl acid phosphate as a stabilizer in a manganese naphthenate solutionin mineral spirits carrying 6% manganese metal.
- EXAMPLE-7 This example shows the use of but-yl acid phosphate in reducing the viscosity of a Xylol solution of calcium naphthenate carrying 5% calcium metal. 7 I
- butyl acid phosphate is added to a commercial 5% calcium naphthenate solution.
- the viscosity is reduced from 37 seconds to seconds at 80 F. on a Gardner-Parks mobilometer with a 200 gram load.
- EXAMPLE 8 In this example a commercial grade of a Xylol solution of the calcium salt of Z-ethylhexoic acid was first prepared. The solution carried 5% oi calcium metal in the form of the salt. The solution thus made showed an initial viscosity of 34:0 cps. at 80 F. There was then added to this solution 3% by weight of the propyl acid phosphate. The viscosity of the calcium salt solution was reduced down to cps.
- EXAMPLE 9 A commercial grade of a copper oleate paste in creosote oil was first prepared so as to carry 7% of copper metal. To this paste was then added 3% by weight of. amyl acid phosphate. The viscosity of the composition which, before the addition, was 4630 cps, dropped, after the addition, to 435 cps.
- EXAMPLE 10 A commercial grade of cobalt linoleate of 9% cobalt metal content, was first prepared by fusion of cobalt acetate and linseed oil fatty acids by standard commercial procedure. The end product was then introduced into linseed oil (which required heating and agitating), so as to provide 2% cobalt metal content in the linseed oil. The dilution of the cobalt linoleate thus prepared showed serious instability after several days standing. There were some discrete particles of the cobalt drier which had separated away from the oil and overall gelation had begun.
- EXAMPLE'12 A commercial grade of lead linoleate drier was modified through the addition of 3% of octyl acid phosphate. It was found that thismodificatiori showed greatly improved stability characteristics in various drying vehicles as compared with the unmodified material.
- EXAMPLE 13 A batch of aluminum oleate .was modified through the addition of 1% of amyl acid -phosphate. When dilutions of the aluminum soaps in benzol were made so as to carry 10% of the aluminum soaps, it was found that theviscos'ity of the dilution of the modified soap showed a vis cosity of only 50 cps. By contrast, the dilutionof the unmodified soap was a viscous gel. 1
- EXAMPLE 14 A manganese drier solution in mineral spirits;- carrying 8% manganese metal, was prepared from a combination of naphthenic acid and- 2 ethylhexoic acid. These acids were used in equal weight proportions in the preparation of To a portion of the drier thus'prepared, 2% of isopropyl acid phosphate was added.- The change in characteristics of the drier are shown in Table 1.
- Table 1 Modified with 2% isopropyl acid Unmodified phosphate 7 Storage Stability Stableindcfinitcly. Gels within a few days. Viscosity in Ops. at 50. 550. Y Alkali Refined Linseed Oil Excellont..n. Poor.
- EXAMPLE 15 A typical combination drier comprising lead' and cobalt was first prepared.
- This drier representing a linseed oil-rosin solution of lead and cobalt linoleate, carried, respectively, 1% cobalt metal and 4% lead metal.
- To a portion of this drier was then added 3% of isopropyl acid phos phate.
- the drier thus modified was clear and stable on long storage, whereas the unmodified drier showed considerable sludging and instability on aging.
- EXAMPLE 16 To a mineral spirits solution of a commercial grade of copper oleate carrying 7% copper metal, was added 1.5% each of amyl acid phosphate and isopropyl acid phosphate. The modified solution showed a viscosity of only 400 cps. By contrast the unmodified solution showed a viscosity of over 4000 cps.
- I EXAMPLE 18 A commercial rade of an iron tallate catalyst was prepared in the usual manner. The end product carried 8% iron metal. To a portion of this end product, there was then added of butyl'acid phosphate. The unmodified, as well as the modified catalyst were then introduced into typical core oil compositions. It was found that the modified catalyst possessed much better solubility-and compatibility with the core oil than the unmodified catalyst.
- EXAMPLE 19 The zinc salt of 2-ethylhexoic acid was first prepared by a fusion of zinc oxide and Z-ethylhexoic acid. The end product was then dissolved in a hydrogenated petroleum solvent sold under the name Solvesso #1 by the Standard Oil Company of New Jersey and consisting of a mixture of approximately 65% aliphatic hydrocarbons of boiling range 250-350 F. and 35% of methylated monocylic aromatic hydrocarbons. The solution carried 10% of zinc metal. When to this solution, 2% of isopropyl acid phosphate was added, the initially high viscosity of the solution was reduced from approximately 9800 cps. at 80 F. to 3600 cps. It was also determined that the modification greatly improved the solubility and compatibility of the zinc salt in many organic vehicles.
- composition of matter consisting essentially of an oil-soluble drier metal salt and a les ser amount of an alkyl acid phosphate wherein the alkyl group embodies not more than 8 carbon atoms. 7
- composition of matter consisting essentially of an oil-soluble drier metal salt and a lesser amount of an amyl acid phosphate.
- composition of matter consisting .essentially of an oil-soluble drier metal salt of naphthenic acid and a lesser amount of an alkyl acid phosphate wherein the alkyl group embodies not more than 8 carbon atoms.
- composition of matter consisting essentially of an oil-soluble drier metal salt of naphthenic acid and a lesser amount of an amyl acid phosphate.
- composition of matter consisting essentially of a water-soluble drier metal salt and a lesser amount of a butyl acid phosphate.
- composition of matter consisting essen tially of a Water-soluble drier metal salt and a lesser amount of an isopropyl acid phosphate.
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Description
Patented Dec. 21, 1948 OIL-SOLUBLE DRIER METAL S ALT COMPOSITIONS Alfred Fischer, Bronx, N. Y., as'signor to Nuodex Products 00., Inc., Elizabeth, N. J a corporation of New York No Drawing. Application July 10,1946, Serial No. 682,586
6 (llaims.
This invention relates to oil-soluble metal salt compositions useful in several arts for various purposes, such, for example, as in connection with paint and varnish driers, bodying agents, cat-v alysts, lubricant additives, etc.
The oil-soluble salts of diverse organic acids are in use for many different purposes. For example, the drying metal salts; that is, principally lead, cobalt, manganese, iron, zinc and nickel salts of certain organic acids; for example, naphthenic acids, tall oil acids, rosin acids, linseed acids, 2-ethylhexoic acid, etc., are widely used as paint, varnish and printing ink driers. The lead salts of certain acids, such as naphthenic acids, are employed not only as driers, but also to impart certain desirable characteristics to lubricants.
Heavy metal and alkali earth metal salts are generally water-insoluble. Their commercial utility depends upon their ability to dissolve in and to be stable in the organic solvents and vehicles for which they are intended. For example, in the case of cobalt, manganese and lead driers they are usually employed in compositions containing drying oils such as linseed oil. In order that they may function properly it is necessary that they be soluble in such oils and many other types of vehicles used in paints, varnishes and printing inks. Similarly a copper salt, intended for use in fungicides, should be soluble in certain organic vehicles, such as creosote oils, with which it is often associated in fungicidal compositions. Zinc salts, such as zinc naththenate, are employed commercially as wetting agents in paints and varnishes. For such application it is desirable that these salts be 301- uble in the vehicles of such compositions.
The metal salts, referred to above, are sometimes employed in solid form; i. e., in the absence of a solvent, but more often they are employed in the form of concentrated liquid solvent solutions. Heretofore, serious difficulties have been experienced in the commercial use of the above described metal salts because they lack the necessary element of solubility. Equally serious troubles are experienced in the preparation of such metal salts and their solutions.
Some of the most serious defects of prior metal salts are as follows:
1. Generally, solvent solutions are of objectionahly high consistency at the maximum'concentration which is preferable from the standpoint of economics and other reasons.
2. These metal soaps in form of their concentrated solutions, as well as when incorporated'into the ultimate compositions for which they may be intended, sludge out during storage; that is, a portion of the active constituent becomes inactive.
3. These, metal salts are often only incompletely soluble in solvents which are intended for the preparation of their concentrated solutions, as Well as in the ultimate vehicles and compositions for which they are intended.
4. The solvent solutions generally contain, for the purpose of minimizing their tendency towards sludging and their lack of solubility, relatively high proportions of organic acids. They may carry as much as 25% of free acids for this purpose. This means that a relatively high amount of extraneous matter is introduced along with the active principal. It also means that, were it not for the presence of such free acid, the concentration of the metal salt in such solutions would be increased.
5. These solutions in many cases do not retain their initial useful low viscosity, but rather tend to increase in viscosity upon aging, sometimes to.
the gelation point.
Various attempts have been made in the past to cope with these disadvantages. Besides the use of free organic acids, certain other agents have also been suggested. For example, certain alcohols have been recommended. However, their use is attended by certain drawbacks such as volatility, relatively low degree of deficiency, etc.
As a result of protracted research and tests, it has now been discovered that it is possible to eliminate all of these disadvantages and others and produce compositions which will function with high efficiency. This is accomplished, according to the present invention, by the use of alkyl acid phosphates. These alkyl acid phosphates greatly reduce the viscosity of solutions of oil-soluble metal salts and greatly improve the stability and solubility of such solutions. Furthermore, they make it possible to effect considerable economies in the preparation of such compositions.
Thus stabilizing agents are of very low vapor pressure and thus will remain permanently associated in the compositions in which they are incorporated. The amount of stabilizing agent needed is relatively small, as low as 25% per total weight of the heavy metal salt solutions having effected markedchanges, but it may be found desirable in some cases to use considerably higher percentages of such stabilizing agents. Generally speaking, we have found that from 1% to 3% produces commercially satisfactory results.
upon solutions of heavy metal salts and alkali,
earth metal salts during the process of manufacture.
It is quite common that water-insoluble heavy metal and alkali earth metal salts are produced by double decomposition in the presence of a water immiscible solvent for the salt thus formed. For example, U. S. Patent No. 2,113,496 describes the operation of such a process. In carrying out that process, certain impurities, originally present in the organic acids, may cause some emulsification which results in difiiculties in separating the two phases as well as in reduced yields of the end product. Through the use of the stabilizing agents of this invention, these difficulties are eliminated or minimized so that smoother production and better yields are obtained. In the past the hazard of emulsification has often required the use of considerable amounts of free organic acids to minimize these tendencies. Through the use of these stabilizing agents the amount of free acid necessary for tie-emulsification may be entirely eliminated or at least greatly reduced.
Other features and advantages of the invention will hereinafter appear in connection with the following illustrative examples. These examples are, by way of illustration, only, and are not intended to be all inclusive of this invention.
The alkyl acid phosphates of this invention are compounds with the general formula R-H2PO4 or R-R-HPO4, as well as combinations of both. In these formulae, R" represents an alkyl radical.
EXAMPLE 1 In this example a manganese naphthenate has been prepared without the agent of this invention, but employing approximately of free naphthenic acid so as to make the product commercially acceptable. mineral spirits solution of manganese naphthenate carrying 6% manganese metal.
625 lbs. of a 14% caustic soda solution is added to a mixture of 512 lbs. of naphthenic acid (acid number 240 mg.) in 389 lbs. of mineral spirits. This results in a substantially "neutraP soap mixture; that is, itcontains neither free acid nor free alkali. 100 lbs. of naphthenic acid is then added. This corresponds to 10% of the finished plroduct. The temperature of the mixture is raised to 180 F. and to it with agitation is added 750 lbs. of an aqueous, manganese sulfate solution containing 8% manganese. After agitation, the mixture is allowed to stratify into an upper mineral spirits layer containing manganese naphthenate and a lower aqueous layer. The latter is run off and the uper mineral spirits layer is dried in vacuo. The final dry product is adjusted with mineral sprits so that the manganese content is 6%.
I Stratification in this preparation is fair and the product is stable (does not gel). The viscosity of this product is 125 cps. at 80 F. and has from poor to fair solubility in alkali refined linseed oil. The heat stability of this product is very poolv The end product is a r 4 Thus the viscosity of the product originally at 125 cps. at F. rises to 200 cps. at 80 F. after heating at 320 F. for 3 hours. The alkali refined linseed oil solubility, which was fair originally, becomes very poor after such heat treatment.
The product of this example represents the best commercial grade that could be produced prior to this invention.
EXAMPLE 2 to cps. The alkali refined linseed oil solubility which was fair becomes excellent. The original product is rendered stable to heating; that is, the viscosity (100 cps.) and the alkali refined linseed oil solubility (excellent), remain unaffected after heating at 320 F. for 3 hours.
EXAMPLE 3 This example shows the addition of butyl acid phosphate to an already prepared manganese naphthenate drier solution carrying 6% manganese metal.
1.75% butyl acid phosphate is incorporated into a commercial 6% manganese naphthenate liquid drier. The commercial product is considerably improved. Its viscosity is reduced from 300 cps. to 100 cps. The alkali refined linseed oil solubility which was fair becomes excellent. The original product is rendered stable to heating; that is, the viscosity (100 cps.) and the alkali refined linseed oil solubility (excellent), remain unaffected after heating at 320 F. for three hours.
EXAMPLE4 This example shows the addition of octyl acid phosphate to an already prepared manganese naphthenate drier solution carrying 6% manganese metal.
2.5% octyl acid phosphate is incorporated into a commercial 6% manganese naphthenate liquid drier. The commercial product is considerably improved. Its viscosity is reduced from 300 cps. to 100 cps. The alkali refined linseed oil solubility which was fair, becomes excellent. The original product is rendered stable to heating; that is, the viscosity (100 cps.) and the alkali refined linseed oil solubility (excellent), remain unaffected after heating at 320 F. for 3 hours.
EXAMPLE 5 This example shows the use of propyl acid phosphate as a stabilizer in a manganese naphthenate solutionin mineral spirits carrying 6% manganese metal.
To a commercial manganese naphthenate drier of 6% manganese metal content there is added 4% of a dilution of propyl acid phosphate. This dilution is made by dissolving equal parts by weight of the phosphate and ethylene glycol monoethyl ether. The manganese drier solution thus modified shows a considerably lower viscosity than the unmodified material and it will also be resistant to increase in viscosity, even upon heating at 320 F. for three hours.
- EXAMPLE 6 This example shows the use of amyl acid phosphate in reducing the viscosity of a mineral spirits solution of copper naphthenate carrying 8% copper metal.
1% amyl acid phosphate is added to a commer cial 8% copper naphthenate solution. The viscosity is reduced. from 2'7 seconds to 1'7 seconds at 80 F. on a Gardner-Parks mobilometer with no load.
EXAMPLE-7 This example shows the use of but-yl acid phosphate in reducing the viscosity of a Xylol solution of calcium naphthenate carrying 5% calcium metal. 7 I
2.25% butyl acid phosphate is added to a commercial 5% calcium naphthenate solution. The viscosity is reduced from 37 seconds to seconds at 80 F. on a Gardner-Parks mobilometer with a 200 gram load.
EXAMPLE 8 In this example a commercial grade of a Xylol solution of the calcium salt of Z-ethylhexoic acid was first prepared. The solution carried 5% oi calcium metal in the form of the salt. The solution thus made showed an initial viscosity of 34:0 cps. at 80 F. There was then added to this solution 3% by weight of the propyl acid phosphate. The viscosity of the calcium salt solution was reduced down to cps.
EXAMPLE 9 A commercial grade of a copper oleate paste in creosote oil was first prepared so as to carry 7% of copper metal. To this paste was then added 3% by weight of. amyl acid phosphate. The viscosity of the composition which, before the addition, was 4630 cps, dropped, after the addition, to 435 cps.
EXAMPLE 10 EXAMPLE 11 A commercial grade of cobalt linoleate of 9% cobalt metal content, was first prepared by fusion of cobalt acetate and linseed oil fatty acids by standard commercial procedure. The end product was then introduced into linseed oil (which required heating and agitating), so as to provide 2% cobalt metal content in the linseed oil. The dilution of the cobalt linoleate thus prepared showed serious instability after several days standing. There were some discrete particles of the cobalt drier which had separated away from the oil and overall gelation had begun. When to the same solid cobalt linoleate, an addition of 4% of the isopropyl acid phosphate was made, the thus modified cobalt drier rendered stable and homogeneous dilutions with the linseed oil.
the drier.
6 EXAMPLE'12 A commercial grade of lead linoleate drier was modified through the addition of 3% of octyl acid phosphate. It was found that thismodificatiori showed greatly improved stability characteristics in various drying vehicles as compared with the unmodified material.
EXAMPLE 13 A batch of aluminum oleate .was modified through the addition of 1% of amyl acid -phosphate. When dilutions of the aluminum soaps in benzol were made so as to carry 10% of the aluminum soaps, it was found that theviscos'ity of the dilution of the modified soap showed a vis cosity of only 50 cps. By contrast, the dilutionof the unmodified soap was a viscous gel. 1
EXAMPLE 14 A manganese drier solution in mineral spirits;- carrying 8% manganese metal, was prepared from a combination of naphthenic acid and- 2 ethylhexoic acid. These acids were used in equal weight proportions in the preparation of To a portion of the drier thus'prepared, 2% of isopropyl acid phosphate was added.- The change in characteristics of the drier are shown in Table 1.
Table 1 Modified with 2% isopropyl acid Unmodified phosphate 7 Storage Stability Stableindcfinitcly. Gels within a few days. Viscosity in Ops. at 50. 550. Y Alkali Refined Linseed Oil Excellont..n. Poor.
Solubility. Heat Stability (3 hours at 50 1290.
320 F.) Viscosity in Ops. at 80 F. Alkali Refined Linseed Oil E :cc1lo,11t Very poor. Solubility.
EXAMPLE 15 A typical combination drier comprising lead' and cobalt was first prepared. This drier, representing a linseed oil-rosin solution of lead and cobalt linoleate, carried, respectively, 1% cobalt metal and 4% lead metal. To a portion of this drier was then added 3% of isopropyl acid phos phate. The drier thus modified was clear and stable on long storage, whereas the unmodified drier showed considerable sludging and instability on aging.
EXAMPLE 16 To a mineral spirits solution of a commercial grade of copper oleate carrying 7% copper metal, was added 1.5% each of amyl acid phosphate and isopropyl acid phosphate. The modified solution showed a viscosity of only 400 cps. By contrast the unmodified solution showed a viscosity of over 4000 cps.
EXAMPLE 1'? To a commercial grade of a manganese naphthenate drier solution in mineral spirits carrying 6% manganese metal, there was added 2% of octyl acid phosphate and .5% of amyl acid phosphate. This modification showed greatly improved stability and solubility characteristics as compared with the initial material. The viscosity also was greatly reduced as a result of this modification.
I EXAMPLE 18 .A commercial rade of an iron tallate catalyst was prepared in the usual manner. The end product carried 8% iron metal. To a portion of this end product, there was then added of butyl'acid phosphate. The unmodified, as well as the modified catalyst were then introduced into typical core oil compositions. It was found that the modified catalyst possessed much better solubility-and compatibility with the core oil than the unmodified catalyst.
EXAMPLE 19 EXAMPLE 20 The zinc salt of 2-ethylhexoic acid was first prepared by a fusion of zinc oxide and Z-ethylhexoic acid. The end product was then dissolved in a hydrogenated petroleum solvent sold under the name Solvesso #1 by the Standard Oil Company of New Jersey and consisting of a mixture of approximately 65% aliphatic hydrocarbons of boiling range 250-350 F. and 35% of methylated monocylic aromatic hydrocarbons. The solution carried 10% of zinc metal. When to this solution, 2% of isopropyl acid phosphate was added, the initially high viscosity of the solution was reduced from approximately 9800 cps. at 80 F. to 3600 cps. It was also determined that the modification greatly improved the solubility and compatibility of the zinc salt in many organic vehicles.
The foregoing examples illustrate the preferred forms of this invention, but-the invention is to be understood as fully commensurate with the appended claims, for I am fully aware of the fact Y 8 that, in addition to theexamples of the alkyl acid phosphates enumerated, a great many others will also operate within the purviewof this invention.
Havin thus fully described the invention, what I claim as new and desire to secure by Letters Patent is:
l. A composition of matter consisting essentially of an oil-soluble drier metal salt and a les ser amount of an alkyl acid phosphate wherein the alkyl group embodies not more than 8 carbon atoms. 7
2. A composition of matter consisting essentially of an oil-soluble drier metal salt and a lesser amount of an amyl acid phosphate.
3. A composition of matter consisting .essentially of an oil-soluble drier metal salt of naphthenic acid and a lesser amount of an alkyl acid phosphate wherein the alkyl group embodies not more than 8 carbon atoms.
4. A composition of matter consisting essentially of an oil-soluble drier metal salt of naphthenic acid and a lesser amount of an amyl acid phosphate.
5. A composition of matter consisting essentially of a water-soluble drier metal salt and a lesser amount of a butyl acid phosphate.
6. A composition of matter consisting essen tially of a Water-soluble drier metal salt and a lesser amount of an isopropyl acid phosphate.
ALFRED FISCHER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Mack et a1. Oct. 22,
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23119D USRE23119E (en) | 1946-07-10 | Oil-soluble dkiek metal salt | |
NL65938D NL65938C (en) | 1946-07-10 | ||
US682586A US2456824A (en) | 1946-07-10 | 1946-07-10 | Oil-soluble drier metal salt compositions |
GB15298/47A GB641168A (en) | 1946-07-10 | 1947-06-10 | Oil-soluble metal salt compositions and method of making same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US682586A US2456824A (en) | 1946-07-10 | 1946-07-10 | Oil-soluble drier metal salt compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US2456824A true US2456824A (en) | 1948-12-21 |
Family
ID=24740318
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US23119D Expired USRE23119E (en) | 1946-07-10 | Oil-soluble dkiek metal salt | |
US682586A Expired - Lifetime US2456824A (en) | 1946-07-10 | 1946-07-10 | Oil-soluble drier metal salt compositions |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US23119D Expired USRE23119E (en) | 1946-07-10 | Oil-soluble dkiek metal salt |
Country Status (3)
Country | Link |
---|---|
US (2) | US2456824A (en) |
GB (1) | GB641168A (en) |
NL (1) | NL65938C (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2565897A (en) * | 1951-08-28 | Drier compositions | ||
US2599553A (en) * | 1950-02-17 | 1952-06-10 | California Research Corp | Complex aluminum soap |
US2628202A (en) * | 1949-09-23 | 1953-02-10 | Leffingwell Chemical Company | Soap useful for making lubricating greases |
US3238274A (en) * | 1960-02-23 | 1966-03-01 | Distillers Co Yeast Ltd | Process for curing unsaturated polyesters using a vanadium compound and an acid phosphate ester as catalysts |
US4257913A (en) * | 1979-09-17 | 1981-03-24 | Tenneco Chemicals, Inc. | Stable manganese salt solutions and a process for their production |
US4331575A (en) * | 1978-04-28 | 1982-05-25 | Tenneco Chemicals, Inc. | Drier systems and surface-coating compositions containing same |
US4778611A (en) * | 1985-05-02 | 1988-10-18 | Herbert Bishop | Oil additive process |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2793962A (en) * | 1952-09-10 | 1957-05-28 | Mcgean Chem Co Inc | Manufacture of metallic soaps useful as driers |
GB986731A (en) * | 1961-01-31 | 1965-03-24 | Catalin Ltd | Foundry moulding process |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2095508A (en) * | 1931-03-02 | 1937-10-12 | Ig Farbenindustrie Ag | Process of manufacturing naphthenates |
US2188951A (en) * | 1939-02-08 | 1940-02-06 | Richards Chemical Works Inc | Insecticide |
US2228668A (en) * | 1941-01-14 | Drying oil composition | ||
US2308502A (en) * | 1940-08-02 | 1943-01-19 | Standard Oil Co | Compounded oil |
US2322307A (en) * | 1939-06-20 | 1943-06-22 | Standard Oil Co California | Compounded oil |
US2370080A (en) * | 1943-02-03 | 1945-02-20 | Atlantic Refining Co | Stabilized lubricant composition |
US2409774A (en) * | 1942-10-08 | 1946-10-22 | Advance Solvents & Chemical Co | Drier metal salt and process of making it |
-
0
- US US23119D patent/USRE23119E/en not_active Expired
- NL NL65938D patent/NL65938C/xx active
-
1946
- 1946-07-10 US US682586A patent/US2456824A/en not_active Expired - Lifetime
-
1947
- 1947-06-10 GB GB15298/47A patent/GB641168A/en not_active Expired
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2228668A (en) * | 1941-01-14 | Drying oil composition | ||
US2095508A (en) * | 1931-03-02 | 1937-10-12 | Ig Farbenindustrie Ag | Process of manufacturing naphthenates |
US2188951A (en) * | 1939-02-08 | 1940-02-06 | Richards Chemical Works Inc | Insecticide |
US2322307A (en) * | 1939-06-20 | 1943-06-22 | Standard Oil Co California | Compounded oil |
US2308502A (en) * | 1940-08-02 | 1943-01-19 | Standard Oil Co | Compounded oil |
US2409774A (en) * | 1942-10-08 | 1946-10-22 | Advance Solvents & Chemical Co | Drier metal salt and process of making it |
US2370080A (en) * | 1943-02-03 | 1945-02-20 | Atlantic Refining Co | Stabilized lubricant composition |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2565897A (en) * | 1951-08-28 | Drier compositions | ||
US2628202A (en) * | 1949-09-23 | 1953-02-10 | Leffingwell Chemical Company | Soap useful for making lubricating greases |
US2599553A (en) * | 1950-02-17 | 1952-06-10 | California Research Corp | Complex aluminum soap |
US3238274A (en) * | 1960-02-23 | 1966-03-01 | Distillers Co Yeast Ltd | Process for curing unsaturated polyesters using a vanadium compound and an acid phosphate ester as catalysts |
US4331575A (en) * | 1978-04-28 | 1982-05-25 | Tenneco Chemicals, Inc. | Drier systems and surface-coating compositions containing same |
US4257913A (en) * | 1979-09-17 | 1981-03-24 | Tenneco Chemicals, Inc. | Stable manganese salt solutions and a process for their production |
US4778611A (en) * | 1985-05-02 | 1988-10-18 | Herbert Bishop | Oil additive process |
Also Published As
Publication number | Publication date |
---|---|
USRE23119E (en) | 1949-05-31 |
GB641168A (en) | 1950-08-09 |
NL65938C (en) |
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