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WO2004094351A2 - Nouveaux agents intermediaires riches en metal - Google Patents

Nouveaux agents intermediaires riches en metal Download PDF

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Publication number
WO2004094351A2
WO2004094351A2 PCT/US2004/012514 US2004012514W WO2004094351A2 WO 2004094351 A2 WO2004094351 A2 WO 2004094351A2 US 2004012514 W US2004012514 W US 2004012514W WO 2004094351 A2 WO2004094351 A2 WO 2004094351A2
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Prior art keywords
acid
composition
group
alcohol
phosphite
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Ceased
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PCT/US2004/012514
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WO2004094351A3 (fr
Inventor
Joseph W. Burley
Rajesh Khattar
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Akzo Nobel NV
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Akzo Nobel NV
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Publication of WO2004094351A3 publication Critical patent/WO2004094351A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/235—Metal derivatives of a hydroxy group bound to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/10—Saturated ethers of polyhydroxy compounds
    • C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
    • 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
    • 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
    • C10M115/00—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof
    • C10M115/04—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof containing oxygen
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
    • C10M129/36—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms containing hydroxy groups
    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals

Definitions

  • Solutions of metal organic salts find use in a range of commercial applications, not limited to, but typified by, driers for paints and as components for the formulation of PVC stabilizers .
  • Other end use applications are as thickeners (also termed “gelling agents") in petroleum- containing compositions (such as greases and oils) and in PVC plastisols, as acid scavengers in lubricating oils, and to form surface coatings of the type conventionally formed from metal alkoxides .
  • These compositions are based on metal carboxylates and, in some cases, on alkyl phenolates .
  • neutral salts can be either: neutral, containing a stoichiometric quantity of acid; acid-deficient, as in the case of basic zinc octoate or basic aluminum tallate; or carbonated, as in the case of carbonated calcium carboxylates , carbonated barium alkyl phenates , carboxylates and mixed alkylphenate/carboxylates .
  • neutral salts exhibit a higher viscosity than carbonated intermediates.
  • barium nonylphenate is used at a barium content of about 12%-13%. At metal levels higher than this, the neutral salt is very viscous.
  • Carbonated barium intermediates typically contain 24-34% barium and are of low viscosity.
  • What are deemed to be new intermediates in accordance with the present invention can be prepared by the reaction of a substantially stoichiometric mixture of either: a phenol and an alcohol ; a carboxylic acid and an alcohol ; or a mixture of a phenol , a carboxylic acid and an alcohol, each with a metal oxide or hydroxide.
  • M is a Group II metal selected from Ba, Sr, Cd, Ca, Mg or where M is a monoalkyltin moiety (R IV Sn) 2/3 or a dialkyltin moiety (R IV 2 Sn) ;
  • R is either H or a saturated or unsaturated alkyl or alkoxy group of up to about 18 carbon atoms
  • R' is a saturated or unsaturated alkyl group of up to about 18 carbon atoms or an aromatic group which is either unsubstituted or substituted with one or more alkyl or alkoxy groups , each of up to about 18 carbon atoms
  • R" is an alk lene group of up to about 4 carbon atoms
  • R"' is either a saturated or unsaturated alkyl group of up to about 18 carbon atoms or an al
  • non-carbonated barium-containing materials with metal levels as high as 32% have been achieved and with metal levels up to about 27% have been achieved with low viscosity.
  • the advantages of this technology are: lower cost/% barium; good epoxidized oil (e.g., epoxidized soybean oil) compatibility, which is not exhibited by carbonated high metal intermediates; and greater versatility in product formulation based on neutral intermediates since higher barium levels in these products can now be achieved. Additionally, this technology allows the formulation of lower volatility products based on neutral intermediates.
  • the intermediates described above are suited for use in the formulation of liquid mixed-metal stabilizers for PVC but they are prone to hydrolysis .
  • a stoichiometric amount of barium hydroxide monohydrate can be reacted with an equimolar mixture of nonylphenol and 2- (2-methoxyethoxy) thanol in mineral spirits to give a low viscosity, homogeneous and stable solution containing 21% barium.
  • a 25.3% barium-containing intermediate can be combined with triphenyl phosphite to give a product containing 13.1% barium and 4.8% phosphorus.
  • the reagent phenols are typified by, but not limited to: phenol, para- nonylphenol , para-octylphenol , para-dodecylphenol , para- cresol, para-t-butylphenol, and para- ethoxyphenol .
  • the reagent acids are typified by, but not limited to: acetic acid, propionic acid, n-valeric acid, 2-methylpentanoic acid, 2- ethylbutyric acid, di-n-propyla ⁇ etic acid, n-heptanoic acid, isomeric butyric acids, n-octanoic acid, 2- ethylhexanoic acid, isononanoic, isooctanoic acid, versatic acid, tall oil acid, oleic acid, benzoic acid, para-t- butylbenzoic acid, isomeric toluic acids, adipic acid, succinic acid, benzene-1 ,2-dicarboxylic acid, and naphthenic acid.
  • acetic acid propionic acid
  • n-valeric acid 2-methylpentanoic acid
  • 2- ethylbutyric acid di-n-propyla ⁇ etic acid
  • the acid radical in the above formulas is redefined as (0 2 CR v C0 2 ) _ >/2 where R v is a saturated or unsaturated alkylene group of 2 to about 10 carbon atoms or a benzene radical (CgH) .
  • Reagent alcohols are typified by, but not limited to: 2- (2-methoxyethoxy) ethanol, 2 - (2-ethoxyethoxy)ethanol, 2- (2-butoxyethoxy) ethanol , 1- (2-methoxyisopropoxy) -2- propanol, nonylphenol ethoxylated with six moles of ethylene oxide, lauryl alcohol ethoxylated with three moles of ethylene oxide, and tripropylene glycol .
  • O ganophosphite esters suitable for combination with the metal organic products of this invention are typified by, but not limited to: triphenyl phosphite, diphenyl isodecyl phosphite, di-isodecyl phenyl phosphite, tride ⁇ yl phosphite, diphenyl phosphite, phenyl 2-ethylhexyl phosphite, diphenyl iso-octyl phosphite, tris nonylphenyl phosphite, tetraphenyl dipropyleneglycol diphosphite, dipropylene glycol phenyl phosphite.
  • patents specify only a substantially equimolar ratio of barium to the alkyl phenol or to the mixture of alkyl phenol and carboxylic acid. In the present invention, this ratio can be as large as 1:0.1.
  • the current invention also relates to the reaction of a stoichiometric total quantity, or less, of acid and alcohol with barium hydroxide. The above U.S. patents describe the use of a significant excess of acids and alcohols .
  • compositions of this invention have been demonstrated to be useful as constituents for PVC stabilizers.
  • the product of Example 2 hereinbelow
  • These general purpose products may, or may not, contain epoxidized soybean oil as a constituent.
  • the product of Example 2 (hereinbelow) can be used to replace the 28% barium-containing, carbonated barium constituent of high barium content barium zinc products with the added benefit of use of the such formulated products in PVC plastisol applications.
  • Such use of high metal , carbonated products is normally prohibited by the occurrence of "gassing" (C0 2 elimination) at high gellation temperatures .
  • Example 1 The present invention is described by the following Examples , which are intended to merely recite certain potential embodiments of the present invention:
  • Example 3 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser was charged 144.7g (0.764 mole) of barium hydroxide monohydrate, 168.5g (0.766 mole) of nonylphenol, 124. Og (0.765 mole) of 2- (2- butoxyethoxy) ethanol , and 104. Og of mineral spirits. The temperature was raised and, over the range of 100°C to 150°C, water was removed (about 40g) . The resultant solution analyzed at 20.3% barium.
  • the composition corresponded to a solution of Ba(OC 6 H 4 C 9 H 19 ) (OC 2 H 4 ⁇ C 2 H 4 OC 4 H 9 ) in mineral spirits.
  • the GH (Gardner Holt) viscosity of this material at 25°C was S.
  • Example 4 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 179.2g (0.946 mole) of barium hydroxide monohydrate, 33.05g (0.150 mole) of nonylphenol, 193.36g (1.611 moles) of 2- (2- ethoxyethoxy) ethanol , 20.48g (0.142 mole) of 2- ethylhexanoic acid, and 129.07g of mineral spirits. The temperature was raised and over, the range of 100°C to 150°C, water was removed (about 66. Og). The resultant solution analyzed at 25.6% barium.
  • the composition corresponded to a solution of Ba(OC 6 HC 9 H ⁇ 9 ) 0 . 15 (0 2 CCH.C 2 H 5 .C 4 Hg)o.i 5 (OC 2 HOC 2 H4 ⁇ CH 3 ) ⁇ . 7 in mineral spirits.
  • Example 5 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 179.2g (0.946 mole) of barium hydroxide monohydrate, 247.5g (1.527 moles) of 2- (2- butoxyethoxy) ethanol , 51.2g (0.355 mole) of 2-ethylhexanoic acid, and 75.3g of mineral spirits. The temperature was raised and, over the range of 100°C to 150°C, water was removed (about 51.2g). The resultant solution analyzed at 24.2% barium and was a low viscosity liquid. The composition corresponded to a solution of Ba(0 2 CCH.C 2 H 5 .C 4 H 9 ) 0 . 4 (OC 2 HOC 2 H 4 OC 4 H 9 ) ⁇ . 6 in mineral spirits.
  • Example 6 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 179.2g (0.946 mole) of barium hydroxide monohydrate, 31.4g of nonylphenol (0.1427 mole), 193.5g (1.6125 mole) of 2- (2-methoxyethoxy) ethanol, 20.5g (0.1424 mole) of 2-ethylhexanoic acid, and 32g of mineral spirits. The temperature was raised and, over the range of 100°C to 150°C, water was removed (about 51.2g) . The resultant solution analyzed at 32% barium and was a viscous liquid.
  • the composition corresponded to a solution of Ba(OC 6 H 4 C 9 H 19 ) 0 . ⁇ s (0 2 CCH.C 2 H 5 .C 4 H 9 ) 0 . ⁇ 5 (OC 2 H 4 ⁇ C 2 H 4 OCH 3 ) ⁇ . 7 in mineral spirits .
  • Example 7 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 179.2g (0.946 mole) of barium hydroxide monohydrate, 62.6g of nonylphenol (0.2845 mole), 193.4g (1.6116 moles) of 2- (2-methoxyethoxy) ethanol, and 97.5g of aromatic 150 solvent. The temperature was raised and, over the range of 100°C to 150°C, water was removed (about 51. lg) . The resultant solution analyzed at 26.5% barium.
  • composition corresponded to a solution of Ba(OC 6 H 4 C 9 H 19 ) 03 (OC 2 H 4 OC 2 H 4 OCH 3 ) ⁇ . 7 in aromatic solvent (Aromatic 150 brand from ExxonMobil Chemical) .
  • aromatic solvent Aromatic 150 brand from ExxonMobil Chemical
  • Example 8 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 179.2g (0.946 mole) of barium hydroxide monohydrate, 175.7g (1.084 moles) of 2- (2- butoxyethoxy) ethanol , 21.6g (0.1770 mole) of benzoic acid, 25.6g (0.177 mole) of 2-ethylhexanoic acid and 120.5g of mineral spirits.
  • the temperature was raised and, over the range of 100 to 150°C, water was removed (about 43. Og).
  • the resultant solution analyzed at 25.8% barium and represented a 25% basic (acid/alcohol-deficient) barium-containing mixed carboxylate/alkoxide .
  • Example 9 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser was charged 137.85g (0.728 mole) of barium hydroxide monohydrate, 210.61g (0.730 mole) of tall oil acid, 87.49g (0.729 mole) of 2- (2- methoxyethoxy) ethanol , and 103.37g of mineral spirits. The temperature was raised and, over the range of 100°C to 150°C, water was removed (42.6g of water). The resultant solution was of low viscosity and analyzed at 19.5% barium. The composition corresponded to a solution of Ba(tallate) (OC 2 H 4 OC 2 H 4 OCH 3 ) in mineral spirits.
  • Ba(tallate) OC 2 H 4 OC 2 H 4 OCH 3
  • Example 10 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 171.6g (0.907 mole) of barium hydroxide monohydrate, 79. Og (0.411 mole) of tripropylene glycol, 181.6g (0.826 mole) of nonylphenol, 9.6g (0.16 mole) of acetic acid, and 207.2g of mineral spirits. The temperature was raised and, over the range of 100 to 150°C, water was removed (about 49g) . The resultant solution analyzed at 20.7% barium.
  • EXAMPLE 12 To a one liter three-neck round-bottom flask equipped with stirrer, thermometer, heating mantle and distillation condenser was charged 224.7g of 2-ethylhexanoic acid, 252.7g of 2- (2-butoxyethoxy) ethanol , 14g of acetic acid, 149. lg of mineral spirits, 87.5g of calcium oxide and l.Og of water. The temperature was raised and, over the range of 100°C to 150°C, water was recovered (29g) . The resulting solution analyzed at 8.5% calcium.
  • the product was a homogeneous, stable solution that is useful for the formulation of liquid mixed metal heat stabilizers for PVC.
  • Example 16 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser was charged 178.5g of barium hydroxide monohydrate, 80.25g of nonylphenol, 246.5g of 2- (2-butoxyethoxy) ethanol, 10. Og of acetic acid, and 35.8g of mineral spirits. The temperature was raised and, over the range of 100°C to 150°C, water was removed (51.0g) . After cooling to 85°C, 313g of diphenyl isodecyl phosphite was carefully charged. An exothermic reaction ensued and the resultant mixture analyzed at 15.7% barium and 3.5% phosphorus .
  • Example 17 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser was charged 223.2g of barium hydroxide monohydrate, 61.20g of 2-ethylhexanoi ⁇ acid,
  • BNP (12%) is a neutral 12% metal barium nonylphenate ZnOct (18%) is an overbased 18% metal 2-ethylhexanoate
  • DPIDP is diphenyl isodecyl phosphite
  • BDK is a commercially available beta-diketone
  • formulations were prepared by sequentially charging ingredients in the order shown to a stirred beaker and, where necessary, applying modest heat to achieve a homogeneous solution .
  • the PVC test formulations were prepared as follows : The formulations were hand mixed before being placed on an oil heated, two-roll mill and mixed for three minutes at 170°C. The mill conditions were: front roll speed - 28rpm, back roll speed - 20rpm, and nip gap - 0.02". After milling for the specified time, the gelled sheets were removed from the mill and cooled to room temperature. Test specimens were punched from the sheets, mounted on glass slides and subjected to an oven test at 190°C. Test specimens were removed from the oven after specified time intervals , and the color deterioration determined by assessment of the ⁇ Hunter' b value (yellowness) . The results of these evaluations are shown in Tables 1 and 2 belo :
  • CdOct (19%) is a neutral 19% metal cadmium octoate
  • ZnOct (14%) is a neutral 14% metal zinc octoate
  • CdNapBenz (13%) is a 13% metal mixed cadmium naphthenate benzoate .
  • Barium BOO (18%) is a 18% metal barium mixed acid octoate, benzoate, oleate
  • ESO is epoxidized soybean oil
  • PVC Emulsion grade resin (Geon 121) 100 Dioctylphthalate 60
  • the ingredients were initially mixed for ten minutes with a Premier Dispersator.
  • the mixed formulations were spread on a clean glass plate using a plastisol draw-down knife. Films of 0.02" thickness were produced.
  • the films were gelled in an oven preheated to 205°C for a period of five minutes . After cooling to ambient temperature the films were stripped from the glass plates .
  • Test specimens were punched from these sheets and subjected to oven heat stability tests as described above. The results of this evaluation are presented below in Table 5.
  • Example 29 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 182.4g (0.964 moles) of barium hydroxide monohydrate, 184.2g (1.246 moles) of dipropylene glycol methyl ether, 106. Og (0.482 moles) of nonylphenol, 12. Og (0.20 moles) of acetic acid, and 167.4g of mineral spirits . The temperature was raised and over the range of 100 to 150°C was removed about 52g of water. The resultant solution analyzed at 22.0% barium.
  • Example 30 To a one liter three-neck round-bottom flask equipped with thermometer, mechanical stirrer, heating mantle and distillation condenser, was charged 171.6g (0.907 moles) of barium hydroxide monohydrate, 74.4g (0.827 moles) of 2- ethoxyethanol , 181.6g (0.826 moles) of nonylphenol, 9.6g (0.16 moles) of acetic acid, and 211.8g of mineral spirits. The temperature was raised and over the range of 100 to 150°C was removed about 49g of water. The resultant solution analyzed at 20.7% barium.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Inorganic Compounds Of Heavy Metals (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

L'invention concerne des nouvelles compositions intermédiaires riches en métal, utilisées en tant que siccatifs pour des peintures et en tant que composants pour la formulation de stabilisateurs PVC. La préparation desdites compositions comprend la réaction d'un mélange sensiblement stoechiométrique comprenant : un phénol et un alcool ; un acide carboxylique et un alcool ; ou un mélange de phénol, d'acide carboxylique, et d'alcool avec un oxyde ou un hydroxyde métallique.
PCT/US2004/012514 2003-04-23 2004-04-23 Nouveaux agents intermediaires riches en metal Ceased WO2004094351A2 (fr)

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US46516903P 2003-04-23 2003-04-23
US60/465,169 2003-04-23

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Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2616904A (en) * 1951-03-16 1952-11-04 Lubrizol Corp Organic alkaline earth metal complex and method of making same
US3551530A (en) * 1967-08-15 1970-12-29 Synthetic Products Co Asymmetric alkaline earth metal phenate-phosphites and method of making same
US5830935A (en) * 1996-06-13 1998-11-03 Omg Americas, Inc. Color of basic metal organic salts by employing C7 -C17 alkyl glycidyl esters and stabilized halogen-containing polymers
US6348438B1 (en) * 1999-06-03 2002-02-19 Chevron Oronite S.A. Production of high BN alkaline earth metal single-aromatic ring hydrocarbyl salicylate-carboxylate

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