WO2002094925A2 - Shelf stable haze free liquids of overbased alkaline earth metal salts, processes and stabilizing halogen-containing polymers therewith - Google Patents

Shelf stable haze free liquids of overbased alkaline earth metal salts, processes and stabilizing halogen-containing polymers therewith Download PDF

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Publication number
WO2002094925A2
WO2002094925A2 PCT/US2001/042768 US0142768W WO02094925A2 WO 2002094925 A2 WO2002094925 A2 WO 2002094925A2 US 0142768 W US0142768 W US 0142768W WO 02094925 A2 WO02094925 A2 WO 02094925A2
Authority
WO
WIPO (PCT)
Prior art keywords
liquid
halogen
containing polymer
calcium
shelf stable
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.)
Ceased
Application number
PCT/US2001/042768
Other languages
English (en)
French (fr)
Other versions
WO2002094925A3 (en
Inventor
James F. Reddy
Chester F. Ramey
Lawrence A. Dominey
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.)
Borchers Americas Inc
Original Assignee
OMG Americas Inc
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 OMG Americas Inc filed Critical OMG Americas Inc
Priority to JP2002592395A priority Critical patent/JP4093864B2/ja
Priority to AU2002225592A priority patent/AU2002225592B2/en
Priority to CA002447330A priority patent/CA2447330C/en
Priority to BRPI0117018-0A priority patent/BR0117018B1/pt
Priority to DE60117864T priority patent/DE60117864T2/de
Priority to EP01995099A priority patent/EP1387863B1/en
Publication of WO2002094925A2 publication Critical patent/WO2002094925A2/en
Publication of WO2002094925A3 publication Critical patent/WO2002094925A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • 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
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • 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
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to a shelf stable haze free
  • liquids and metal carboxylates of zinc, cadmium or alkyltin are provided
  • halogen-containing polymers such as polyvinyl
  • carboxylic acids alkyl phenols, and sulfonic acids are disclosed in the
  • alkyl phenol is also a major
  • Propylene oxide is classified as a possible carcinogen and laboratory
  • Propylene oxide is also listed as a severe eye irritant, and prolonged exposure to propylene oxide vapors may result in permanent damage to
  • propylene oxide is extremely flammable and
  • liquid calcium-zinc stabilizers are desirous, but not practical, as
  • Storage stability is due to the incompatibility among the metal
  • liquid calcium compositions are no longer homogeneous or readily pourable and must be
  • the present invention relates to a shelf stable haze free
  • these liquids contain an alkaline earth metal carbonate, an
  • Liquid overbased calcium and barium salts are preferably provided and, in a preferred form of the invention, the
  • liquids are essentially free of a phenol or a phenolic derivative.
  • the invention also relates to a process for preparing the
  • the process involves reacting an alkaline earth metal base
  • the mixture is acidified,
  • an overbased calcium fatty acid salt for example, that may be filtered at commercial or practical rates to remove unwanted impurities
  • the metal base slurry is added at a controlled rate which does not
  • the reaction is
  • the pH is controlled during the reaction so that the fatty acid is
  • fatty acid salts are suitable for use in making mixed metal stabilizer
  • compositions with zinc, cadmium or alkyltin carboxylates are compositions with zinc, cadmium or alkyltin carboxylates.
  • Other metal such as aluminum, cadmium or alkyltin carboxylates.
  • component can also be barium, calcium, strontium, lead, bismuth or
  • PVC chloride
  • compositions of the invention have been demonstrated over presently
  • overbased calcium fatty acid carboxylates exhibit the development of
  • the haze free liquids of this invention allow easy handling, storage and filtration. Furthermore,
  • barium or calcium carboxylates are employed in vinyl halide polymers
  • the shelf stable haze in one preferred form of the invention, the shelf stable haze
  • liquid being preferably free of a phenol or a phenolic derivative such as a
  • the alkaline earth metal in another form of the invention, the alkaline earth metal
  • sulfate suifide or sulfite may be formed instead of the carbonate
  • the acidic gas used in the process is sulfur dioxide, sulfur trioxide, carbon
  • the fatty acid of the overbased liquid carboxylate is
  • C 12 -C 22 fatty acid generally a C 12 -C 22 fatty acid, including, for example, lauric, myristic,
  • palmitic, stearic, archidic and behenic among the saturated fatty acids.
  • Unsaturated fatty acids include palmitoleic, oleic, linoleic, and linolenic.
  • oleic is presently preferred in preparing the
  • the alkaline earth metal of the salt is selected from the
  • shelf stable haze free overbased calcium oleates have been
  • overbased calcium salts contain calcium carbonate,
  • aliphatic alcohol having at least 8 carbon atoms, more preferably an
  • alcohol having 8 to 14 carbon atoms such as, isodecanol, dodecanol,
  • octanol tridecanol and tetradecanol.
  • Isodecanol is presently preferred.
  • phenol may be excluded from the reaction
  • alkaline earth salt of the fatty acid is believed to be a thermodynamically stable microemulsion.
  • the microemulsion has micells and a continuous
  • micells consist of an alkaline earth metal carbonate and an
  • microemulsion consists of the liquid hydrocarbon and the higher
  • salts up to about 1 3-1 5% by weight calcium are produced and, for
  • barium salts up to about 36% by weight barium may be produced.
  • glycol or a glycol ether along with the higher aliphatic alcohol.
  • a glycol or a glycol ether along with the higher aliphatic alcohol.
  • glycol ether may be selected from the group consisting of diethylene
  • glycol monobutyl ether butyl Carbitol ®
  • triethylene glycol dipropylene
  • glycol diethylene glycol monomethyl ether, ethylene glycol monobutyl
  • a surfactant and catalyst promote the reaction.
  • the mixture is acidified and preferably
  • reaction product to produce a shelf stable haze free liquid overbased
  • method is the step of adding during carbonation a dispersion of alkaline
  • liquid hydrocarbon liquid hydrocarbon and an aliphatic alcohol having at least one of the following properties:
  • the product which is produced is filterable
  • method of this invention is the ability to filter the reaction product to form
  • silica iron oxide and other metal species, unreacted calcium hydroxide,
  • Metal ratio as used herein indicates the ratio
  • the process of the present invention may be used to prepare
  • barium fatty acid carboxylates have been made without the need for a
  • component may be derived from any alkaline earth metals and, of these,
  • the metal bases are particularly preferred.
  • the metal bases are calcium and barium bases.
  • the phenol or alkyl phenol may be included to yield
  • liquid overbased products As stated above, the fatty. acids, or mixtures
  • a surfactant that facilitates the reaction is the alkaline earth
  • surfactants may be included, for example, general purpose surface active
  • process and the liquid reaction products generally includes any
  • liquid hydrocarbon is selected
  • preparation of basic salts is an amount which is more than one equivalent
  • base included may be any amount up to that amount which is no longer
  • the ratio of equivalents will be at least 3: 1 . In those instances
  • hydrocarbon oil preferably aliphatic alcohol
  • alkaline earth fatty acid salt i.e. Ca oleate
  • the mixture forms a stable inverse
  • aliphatic alcohol (isodecanol) are about 2: 1 to about 4: 1 , with about 2: 1
  • glycol ethers may be used at about 1 -1 5% of the final
  • butyl Carbitol preferably at about 6%
  • triethylene glycol at
  • reaction is formulated to be an easily pumpable mixture with the general
  • Hydrocarbon oil about 30-35% Isodecanol (cosurfactant) about 1 5-1 8%
  • Triethylene glycol about 0-0.8%
  • the catalyst propionic acid or a lower aliphatic mono, di, or
  • tricarboxylic acid is used in the amount of about 0-0.1 % of the final
  • the step of carbonation involves treating the mixtures
  • titratable basicity is determined using phenolphthalein. Generally, the
  • titratable basicity is reduced to a base number below about 1 0.
  • the base, fatty acid and liquid hydrocarbon are mixed, generally heated,
  • the carbon dioxide preferably is conducted at elevated temperatures
  • the range of temperatures used for this step may be any temperature
  • temperatures may be used such as 250° C, but there is no apparent
  • acids, sulfur dioxide and carbon dioxide are preferred, and the most
  • carbon dioxide When carbon dioxide is used the alkaline
  • suifide and sulfite salts are formed.
  • a halogen-containing polymer such as a vinyl halide resin
  • vinyl halide resin such as polyvinyl chloride or
  • Vinyl halide resin as
  • vinyl halide resins would include vinylidene chloride polymers, vinyl
  • bromide and fluoride may be used.
  • Examples of the latter polymers are
  • compositions are well known. These metal compounds serve to capture
  • the metal can be lead, cadmium, barium, calcium,
  • the stabilizers are zinc, strontium, bismuth, tin, or antimony, for example.
  • the stabilizers are zinc, strontium, bismuth, tin, or antimony, for example.
  • carbon chain link monocarboxyiic acid such as lauric, oleic, stearic,
  • Metal salts of alkyl phenates may be
  • the metal stabilizer is a mixed metal salt of a carboxylic acid.
  • teethers for centuries, teethers, fencing, corrugated wall panels, dashboards, and shifter boots.
  • the dispersion was added at a rate of about 3 g per minute. At this point
  • thermocouple heating mantle and Dean-Stark trap with condenser
  • the filtrate was analyzed to contain 14.5% calcium by weight.
  • Stabilizer formulation contained 5% Ca, 1 .2% Zn (zinc
  • Stabilizer formulation contained 5 % Ca,
  • compositions are as follows:
  • Beta Diketone 3.0% 3.0%
  • the stabilizer compositions are as follows: Stabilizer Formulation B
  • PVC formulation comprised of 100 parts PVC resin ( value 66), 30 parts
  • stabilizer A and B gave better clarity or crispness than stabilizer C.
  • the stabilizer compositions have been identified above as A, B and C with A containing the New Calcium, B containing the Old
  • Plate out is determined by introducing a red pigment into a
  • a white clean up compound is then placed onto the rolls and the
  • the colorimeter assigns a numerical value on the
  • the red formulation is milled for 4 minutes undisturbed after

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Detergent Compositions (AREA)
PCT/US2001/042768 2001-05-18 2001-10-16 Shelf stable haze free liquids of overbased alkaline earth metal salts, processes and stabilizing halogen-containing polymers therewith Ceased WO2002094925A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2002592395A JP4093864B2 (ja) 2001-05-18 2001-10-16 貯蔵安定性があり混濁がない塩基過剰なアルカリ土類金属塩の液体、プロセス及びそれを用いたハロゲン含有重合体の安定化
AU2002225592A AU2002225592B2 (en) 2001-05-18 2001-10-16 Shelf stable haze free liquids of overbased alkaline earth metal salts, processes and stabilizing halogen-containing polymers therewith
CA002447330A CA2447330C (en) 2001-05-18 2001-10-16 Shelf stable haze free liquids of overbased alkaline earth metal salts, processes and stabilizing halogen-containing polymers therewith
BRPI0117018-0A BR0117018B1 (pt) 2001-05-18 2001-10-16 "processo de preparação de lìquido estável à armazenagem, isento de turbidez, de um sal de metal alcalino-terroso de ácido graxo, lìquido estável à armazenagem, composição polimérica e composição estabilizante".
DE60117864T DE60117864T2 (de) 2001-05-18 2001-10-16 Trübungsfreie und lagerstabile flüssigkeiten auf basis von überbasigen basischen erdalkalimetallsalzen, ihr herstellungsverfahren, und die damit stabilisierten halogenenthaltenden polymeren
EP01995099A EP1387863B1 (en) 2001-05-18 2001-10-16 Shelf stable haze free liquids of overbased alkaline earth metal salts, processes and stabilizing halogen-containing polymers therewith

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/861,393 US6689893B2 (en) 2001-05-18 2001-05-18 Shelf stable haze free liquids of overbased alkaline earth metal salts
US09/861,393 2001-05-18

Publications (2)

Publication Number Publication Date
WO2002094925A2 true WO2002094925A2 (en) 2002-11-28
WO2002094925A3 WO2002094925A3 (en) 2003-03-13

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PCT/US2001/042768 Ceased WO2002094925A2 (en) 2001-05-18 2001-10-16 Shelf stable haze free liquids of overbased alkaline earth metal salts, processes and stabilizing halogen-containing polymers therewith

Country Status (10)

Country Link
US (3) US6689893B2 (enExample)
EP (1) EP1387863B1 (enExample)
JP (1) JP4093864B2 (enExample)
AT (1) ATE319769T1 (enExample)
AU (1) AU2002225592B2 (enExample)
BR (1) BR0117018B1 (enExample)
CA (1) CA2447330C (enExample)
DE (1) DE60117864T2 (enExample)
TW (1) TWI225514B (enExample)
WO (1) WO2002094925A2 (enExample)

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WO2004005390A3 (en) * 2002-07-08 2004-07-01 Crompton Corp Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same
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US6835328B2 (en) 2002-07-08 2004-12-28 Crompton Corporation Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same
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US7163912B2 (en) 2001-05-18 2007-01-16 Omg Americas, Inc. Lubricant compositions containing an overbased amorphous alkaline earth metal salt as a metal protectant
US6613723B2 (en) 2001-12-06 2003-09-02 Exxonmobil Chemical Patents Inc. Overbased barium complexes of C8 to C10 carboxylic acids
WO2004005390A3 (en) * 2002-07-08 2004-07-01 Crompton Corp Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same
US6835328B2 (en) 2002-07-08 2004-12-28 Crompton Corporation Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same
WO2004078849A3 (en) * 2003-03-04 2004-12-02 Omg Americas Inc Lubricant compositions containing an overbased amorphous alkaline earth metal salt as a metal protectant
KR100743285B1 (ko) * 2003-03-04 2007-07-26 오엠지 아메리카스, 인코포레이티드 금속 보호제로서 과염기성 무정형 알칼리 토금속 염을함유하는 윤활유 조성물
AU2004218032B2 (en) * 2003-03-04 2007-10-04 Omg Americas, Inc. Lubricant compositions containing an overbased amorphous alkaline earth metal salt as a metal protectant
KR100853348B1 (ko) * 2003-03-04 2008-08-21 오엠지 아메리카스, 인코포레이티드 분말 형태의 과염기성 무정형 알칼리 토금속 염 및 이의제조방법
CN1802427B (zh) * 2003-03-04 2010-08-04 Omg美国公司 含有高碱性无定形碱土金属盐作为金属保护剂的润滑剂组合物
EP1670878A4 (en) * 2003-09-24 2010-09-29 Chemtura Corp CARBONATE METAL CARBONATE / CARBOXYLATE MICROEMULSIONS

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BR0117018B1 (pt) 2011-05-03
US20030050490A1 (en) 2003-03-13
DE60117864D1 (de) 2006-05-04
EP1387863A2 (en) 2004-02-11
BR0117018A (pt) 2004-05-04
CA2447330C (en) 2008-10-14
US6844386B2 (en) 2005-01-18
EP1387863B1 (en) 2006-03-08
US20040053795A1 (en) 2004-03-18
CA2447330A1 (en) 2002-11-28
AU2002225592B2 (en) 2005-09-22
JP4093864B2 (ja) 2008-06-04
TWI225514B (en) 2004-12-21
US6689893B2 (en) 2004-02-10
ATE319769T1 (de) 2006-03-15
DE60117864T2 (de) 2006-08-17
US20040162372A1 (en) 2004-08-19
JP2004527634A (ja) 2004-09-09

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