EP1644310A2 - Carboxylate metallique alcalino-terreux liquide de couleur claire hautement hyperbasique - Google Patents

Carboxylate metallique alcalino-terreux liquide de couleur claire hautement hyperbasique

Info

Publication number
EP1644310A2
EP1644310A2 EP04777185A EP04777185A EP1644310A2 EP 1644310 A2 EP1644310 A2 EP 1644310A2 EP 04777185 A EP04777185 A EP 04777185A EP 04777185 A EP04777185 A EP 04777185A EP 1644310 A2 EP1644310 A2 EP 1644310A2
Authority
EP
European Patent Office
Prior art keywords
carboxylic acid
earth metal
alkaline earth
acid
barium
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.)
Withdrawn
Application number
EP04777185A
Other languages
German (de)
English (en)
Inventor
Rajesh Khattar
Florentina M. Pavel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Akzo Nobel NV filed Critical Akzo Nobel NV
Publication of EP1644310A2 publication Critical patent/EP1644310A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07C51/414—Preparation of superbasic salts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic 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
    • 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
    • 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
    • C10M2207/26—Overbased carboxylic acid salts
    • 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
    • C10N2010/04—Groups 2 or 12

Definitions

  • European Patent Publication No. 279,493 describes the preparation of basic alkaline-earth metal salts of organic carboxylic acids by utilizing a mixture of aromatic and aliphatic carboxylic acids. The salts obtained in this way have dispersant properties suitable for use in lubricating oil and fuel compositions. This patent doesn't describe the use of such compositions in stabilizing halogen- containing polymer compositions.
  • U.S. Published Patent Application. No. 2003/0119683 describes the preparation of over-based barium complexes wherein one of the reagents is an alkaline earth carboxylate of a fatty acid containing from 12 to 22 carbon atoms in the fatty alkyl group.
  • the present invention is a process for preparing a highly over-based, (alkyl) phenol-free, light colored alkaline-earth metal organic complex of a carboxylic acid and its use in formulating stabilizer compositions for halogen-containing polymers.
  • the acid reagent that is used is a non-fatty alkyl-containing acid, such as one containing an aliphatic moiety less than or equal to C 8 , an aromatic group-containing acid, or mixtures thereof.
  • the process involves reacting a basic alkaline-earth metal compound, such as barium, a glycol or glycol ether (which brings the barium reagent into solution) , a carboxylic acid of the type just described, and carbon dioxide in a hydrocarbon solvent to produce a light colored over-based metal organic salt.
  • a basic alkaline-earth metal compound such as barium, a glycol or glycol ether (which brings the barium reagent into solution)
  • a carboxylic acid of the type just described and carbon dioxide
  • a fatty alcohol, a glycol or glycol derivative is used as a solubilizing agent to keep the final product well dispersed in the reaction medium.
  • the alkaline earth metal compound that is employed can be present in the form of a hydroxide or oxide.
  • the alcohol and/or glycol that can be employed can be selected from those conventionally used in preparing overbased alkaline earth metal compositions of the general type represented by the instant invention.
  • the alkyl moiety can contain up to about 20 carbon atoms therein.
  • Representative alcohols include oleyl alcohol and cetyl alcohol.
  • Glycol-containing reagents include dipropylene glycol methyl ether, dipropylene glycol butyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, tripropylene glycol, triethylene glycol, the glycol ester of a fatty acid, and the like. These reagents should not be in amount less than about 0.1%, and they are more preferably used at a level of from about 3% to about 5%, based on the weight of total reagent content.
  • the carboxylic acid may either contain an alkyl group of up to eight carbon atoms or either an alkyl-substituted or unsubstituted aromatic group, and is of the formula R"COOH, where R" is the alkyl group of the foregoing type or alkyl-substituted or unsubstituted aromatic group.
  • a representative acid for use is 2-ethylhexanoic acid.
  • the molar ratio of barium compound to such acid in the initial reaction medium is from about 2.5 to about 7.5 moles for each mole of acid.
  • the solvent is chosen to achieve low odor and low volatility and can be a hydrocarbon, mineral oil, or hydrocarbon/mineral oil mixtures of low aromatic content.
  • the metal content of the product can be as high as 40% when made by this process route.
  • the final product is highly over-based and (alkyl) phenol-free and possesses a very light color and can be used to make very light colored heat stabilizers.
  • Heat stabilizer formulations can be easily made using this new highly over-based, (alkyl) phenol-free barium and its performance, when compared against alkyl phenol-derived over-based barium, exhibited slightly better initial to mid-term color hold.
  • the reactor contents were then heated slowly to 140°C, and water was removed.
  • Carbon dioxide was then turned on at a rate of 1 LPM (liter per minute) for 1 to 1.5 hours, and water of the reaction was removed.
  • Mineral spirits was then replaced with a mineral oil.
  • the product was filtered using a filter aid at 140°C and a very light colored liquid product containing 40% barium was obtained.
  • the reactor contents were then heated slowly to 140°C, and water was removed.
  • Carbon dioxide was then turned on at a rate of 1 LPM (liter per minute) for 1 to 1.5 hours, and water of the reaction was removed.
  • the product was filtered using a filter aid at 140°C and a very light colored liquid product containing 33% barium was obtained.
  • the reactor contents were then heated slowly to 140°C, and water was removed. Carbon dioxide was then turned on at a rate of 1 LPM (liter per minute) for 1 to 1.5 hours, and water of the reaction was removed.
  • the product was filtered using a filter aid at 140°C and a very light colored liquid product containing 32% barium was obtained.
  • the reactor contents were then heated slowly to 140°C, and water was removed. Carbon dioxide was then turned on at a rate of 1 LPM (liter per minute) for 1 to 1.5 hours, and water of the reaction was removed.
  • the product was filtered using a filter aid at 140°C and a very light colored liquid product containing 36% barium was obtained.
  • the reactor contents were then heated slowly to 140°C, and water was removed. Carbon dioxide was then turned on at a rate of 1 LPM (liter per minute) for 1 to 1.5 hours, and water of the reaction was removed.
  • the product was filtered using a filter aid at 140°C and a very light colored liquid product containing 37% barium was obtained.
  • the reactor contents were then heated slowly to 140°C, and water was removed. Carbon dioxide was then turned on at a rate of 1 LPM (liter per minute) for 1 to 1.5 hours, and water of the reaction was removed.
  • the product was filtered using a filter aid at 140°C and a very light colored liquid product containing 34% barium was obtained.
  • the reactor contents were then heated slowly to 140°C, and water was removed.
  • Carbon dioxide was then turned on at a rate of 1 LPM (liter per minute) for 1 to 1.5 hours, and water of the reaction was removed.
  • the product was filtered using a filter aid at 140°C and a very light colored liquid product containing 31% barium was obtained.
  • Example 8 The performance of the highly over-based (alkyl) phenol-free barium complex described in Example 1 was compared against an alkyl phenol-containing 34% barium, stabilizer composition containing 9% barium, 2% Zn (zinc octoate) , 3.5% P (diphenyl isodecyl phosphite), 4% carboxylic acid, 0.5% anti-oxidant, 2% beta-diketone (dibenzoyl methane) and diluent. The performance of these stabilizers was evaluated in a PVC formulation containing 100 parts of PVC resin, 45 parts phthalate plasticizer, 2.5 parts of epoxidized soybean oil and 2.5 parts of a stabilizer.
  • the stabilized PVC compounds were then milled at 350- 360°F for five minutes at 25-mil thickness.
  • the thermal stability was carried out at 380°F over seventy minutes.
  • Stabilizer containing new phenol-free barium demonstrated better early to mid-term performance in color as measured by a calorimeter as an indication of yellowing (see Table 1) than a stabilizer containing alkyl phenol derived barium.
  • Table 1 Table 1

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un complexe organique métallique alcalino-terreux hyperbasique d'un acide carboxylique, produit au moyen d'un procédé consistant à faire réagir un composé métallique alcalino-terreux basique, un alcool et/ou glycol, un acide carboxylique et du dioxyde de carbone. Ledit acide carboxylique est un acide carboxylique non gras contenant un groupe alkyle, par exemple un acide carboxylique contenant un groupe alkyle qui peut comporter jusqu'à huit atomes de carbone et/ou un acide carboxylique contenant un groupe aromatique substitué ou non par un groupe alkyle.
EP04777185A 2003-07-11 2004-06-25 Carboxylate metallique alcalino-terreux liquide de couleur claire hautement hyperbasique Withdrawn EP1644310A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48647403P 2003-07-11 2003-07-11
PCT/US2004/020667 WO2005007607A2 (fr) 2003-07-11 2004-06-25 Carboxylate metallique alcalino-terreux liquide de couleur claire hautement hyperbasique

Publications (1)

Publication Number Publication Date
EP1644310A2 true EP1644310A2 (fr) 2006-04-12

Family

ID=34079233

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04777185A Withdrawn EP1644310A2 (fr) 2003-07-11 2004-06-25 Carboxylate metallique alcalino-terreux liquide de couleur claire hautement hyperbasique

Country Status (3)

Country Link
US (1) US20060194704A1 (fr)
EP (1) EP1644310A2 (fr)
WO (1) WO2005007607A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7342093B2 (en) * 2004-07-23 2008-03-11 University Of Massachusetts Compounds that inhibit Hsp90 protein-protein interactions with IAP proteins
MX2010011509A (es) * 2008-09-05 2011-03-04 Omg Americas Inc Grasa compleja del carboxilato de metal obrebasificado y procedimieno para su fabricacion.
CN111138671B (zh) * 2018-11-02 2021-09-14 四川大学 一种金属-有机高分子化合物及其制备方法
FR3126781B1 (fr) * 2021-09-03 2024-08-09 Societe Des Transp Petroliers Par Pipeline Trapil Dispositif d’inspection d’une conduite, notamment à l’égard de piquages clandestins

Family Cites Families (13)

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Publication number Priority date Publication date Assignee Title
US3194823A (en) * 1963-03-18 1965-07-13 Lubrizol Corp Organic complexes
US4159973A (en) * 1978-03-06 1979-07-03 Tenneco Chemicals, Inc. Stabilizer systems and vinyl halide resin compositions containing same
JPS54137044A (en) * 1978-04-17 1979-10-24 Adeka Argus Chem Co Ltd Halogen-containing resin composition
US4665117A (en) * 1985-12-20 1987-05-12 The Lubrizol Corporation Basic metal salts having improved color and stability and vinyl halide polymers containing same
GB8703549D0 (en) * 1987-02-16 1987-03-25 Shell Int Research Preparation of basic salt
GB8917094D0 (en) * 1989-07-26 1989-09-13 Bp Chemicals Additives Chemical process
JP2762150B2 (ja) * 1990-03-15 1998-06-04 旭電化工業株式会社 含ハロゲン樹脂組成物
GB9022805D0 (en) * 1990-10-19 1990-12-05 Exxon Chemical Patents Inc Metal carboxylates
JPH07286080A (ja) * 1994-02-24 1995-10-31 Nissan Fuero Yuki Kagaku Kk ハロゲン含有樹脂組成物
US5859267A (en) * 1995-11-08 1999-01-12 Omg Americas, Inc. Process for improving color of basic metal organic salts and stabilizing halogen-containing polymers therewith
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
ES2242906T3 (es) * 2001-11-28 2005-11-16 Akzo Nobel N.V. Carboxilatos de metal alcalino-terreo carbonatados neutros.
US6613723B2 (en) * 2001-12-06 2003-09-02 Exxonmobil Chemical Patents Inc. Overbased barium complexes of C8 to C10 carboxylic acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005007607A2 *

Also Published As

Publication number Publication date
WO2005007607A3 (fr) 2005-03-31
WO2005007607A2 (fr) 2005-01-27
US20060194704A1 (en) 2006-08-31

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