WO2011041372A1 - Acetylated polyglycerine fatty acid ester and a pvc insulator plasticised therewith - Google Patents

Acetylated polyglycerine fatty acid ester and a pvc insulator plasticised therewith Download PDF

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Publication number
WO2011041372A1
WO2011041372A1 PCT/US2010/050664 US2010050664W WO2011041372A1 WO 2011041372 A1 WO2011041372 A1 WO 2011041372A1 US 2010050664 W US2010050664 W US 2010050664W WO 2011041372 A1 WO2011041372 A1 WO 2011041372A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
plasticizer
composition
acid ester
acetylated
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/US2010/050664
Other languages
English (en)
French (fr)
Inventor
Bharat I. Chaudhary
Beate Sczekalla
Klaus Schiller
Michael Meerbote
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.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
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 Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to BR112012007261-7A priority Critical patent/BR112012007261B1/pt
Priority to KR1020127010839A priority patent/KR101907698B1/ko
Priority to EP10763277.0A priority patent/EP2470596B1/en
Priority to US13/498,485 priority patent/US9481633B2/en
Priority to CA2775574A priority patent/CA2775574C/en
Priority to JP2012532259A priority patent/JP5808330B2/ja
Priority to CN201080054103.6A priority patent/CN102666697B/zh
Priority to MX2012003940A priority patent/MX2012003940A/es
Publication of WO2011041372A1 publication Critical patent/WO2011041372A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/33—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with hydroxy compounds having more than three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0016—Plasticisers
    • 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
    • C08K5/10—Esters; Ether-esters
    • 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
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • 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
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06—Homopolymers or copolymers of vinyl chloride
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • H01B3/443—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins from vinylhalogenides or other halogenoethylenic compounds

Definitions

  • the present plasticizer composition exhibits an unexpected synergy between low viscosity and high molecular weight and yields a phthalate-free, safe, plasticized PVC with physical, chemical, and mechanical properties that meet and/or exceed the properties of PVC resins plasticized with conventional adipic polyester plasticizers and/or conventional phthalate-based plasticizers and/or conventional trimellitate-based plasticizers.
  • a phthalate-free, safe, plasticized PVC with physical, chemical, and mechanical properties that meet and/or exceed the properties of PVC resins plasticized with conventional adipic polyester plasticizers and/or conventional phthalate-based plasticizers and/or conventional trimellitate-based plasticizers.
  • Even more especially noteworthy is the retention of tensile properties exhibited by the present composition after oven aging for 96 hours in IRM 902 oil at temperatures as high as 100°C.
  • the polymeric composition includes a filler.
  • suitable fillers include calcium carbonate, calcined clay, whiting, fuller's earth, magnesium silicate, barium sulfate, calcium sulfate, strontium sulfate, titanium dioxide, magnesium oxide, magnesium hydroxide, calcium hydroxide, hydrophilic fumed silica, hydrophobic (surface treated) fumed silica, and any combination of the foregoing.
  • suitable fillers include calcium carbonate, calcined clay, whiting, fuller's earth, magnesium silicate, barium sulfate, calcium sulfate, strontium sulfate, titanium dioxide, magnesium oxide, magnesium hydroxide, calcium hydroxide, hydrophilic fumed silica, hydrophobic (surface treated) fumed silica, and any combination of the foregoing.
  • Nonlimiting examples of calcined clay are Satintone ® SP-33 and Polyfil ® 70.
  • the polymeric composition includes a lubricant.
  • suitable lubricants include stearic acid, metal salts of stearic acid, paraffin wax, and polyethylene glycols.
  • the lubricants may be used alone or in combination.
  • the lubricant may also be combined with the heat stabilizer.
  • Hydroxyl Number is an indication of the degree of acetylation and is a measure of the number of hydroxyl groups present in a polymer.
  • the hydroxyl number is the number of milligrams of potassium hydroxide required to neutralize the hydroxyl groups in one gram of polymer.
  • the hydroxyl number is determined in accordance with German Standard DIN 53 240 (mg KOH/g).
  • 94 g (0.3 mol) tetraglycerol (as received from oligomerization of glycerol) and 70 g (0.1 mol) palm kernel oil are introduced in an autoclave cylinder.
  • the cylinder is closed and put into the heating mantle.
  • the mixture is heated with mechanical stirring (400 rpm) at a temperature of 240 °C for 13 hours.
  • the product is a yellow liquid product (monoester of tetraglycerol and palm kernel oil fatty acid).
  • Blends of polyvinylchloride (PVC) and three different plasticizer mixtures (and additives) are prepared in Examples 16 to 18 and comparative samples 9 to 10.
  • Each plasticizer mixture is composed of acetylated monoester of tetraglycerol and lauric acid (APE) (from Example 1 above) or DIDP or TOT and PLAS-CHEK ® 775 epoxidized soybean oil (ESO).
  • APE acetylated monoester of tetraglycerol and lauric acid
  • ESO epoxidized soybean oil
  • Three different plasticizer mixtures are prepared with the following APE-to-ESO weight ratio and two different comparative samples are prepared with the following DIDP-to-ESO weight ratio or TOTM-to-ESO weight ratio (based on total weight of the plasticizer mixture) as shown in Table B:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/US2010/050664 2009-09-30 2010-09-29 Acetylated polyglycerine fatty acid ester and a pvc insulator plasticised therewith Ceased WO2011041372A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BR112012007261-7A BR112012007261B1 (pt) 2009-09-30 2010-09-29 Composição, composição polimérica e condutor revestido
KR1020127010839A KR101907698B1 (ko) 2009-09-30 2010-09-29 아세틸화 폴리글리세린 지방산 에스테르 및 이를 이용하여 가소화된 ｐｖｃ 절연물
EP10763277.0A EP2470596B1 (en) 2009-09-30 2010-09-29 Acetylated polyglycerine fatty acid ester and a pvc insulator plasticised therewith
US13/498,485 US9481633B2 (en) 2009-09-30 2010-09-29 Acetylated polyglycerine fatty acid ester and a PVC insulator plasticised therewith
CA2775574A CA2775574C (en) 2009-09-30 2010-09-29 Acetylated polyglycerine fatty acid ester and a pvc insulator plasticised therewith
JP2012532259A JP5808330B2 (ja) 2009-09-30 2010-09-29 アセチル化ポリグリセリン脂肪酸エステルおよびそれで可塑化されたｐｖｃ絶縁体
CN201080054103.6A CN102666697B (zh) 2009-09-30 2010-09-29 乙酰基化的聚甘油脂肪酸酯以及用其增塑的聚氯乙烯绝缘材料
MX2012003940A MX2012003940A (es) 2009-09-30 2010-09-29 Ester de acido graso de poliglicerina acetilada y un aislante de pvc plastificado con el mismo.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US24732909P 2009-09-30 2009-09-30
US61/247,329 2009-09-30

Publications (1)

Publication Number Publication Date
WO2011041372A1 true WO2011041372A1 (en) 2011-04-07

Family

ID=42985530

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/050664 Ceased WO2011041372A1 (en) 2009-09-30 2010-09-29 Acetylated polyglycerine fatty acid ester and a pvc insulator plasticised therewith

Country Status (10)

Country Link
US (1) US9481633B2 (enExample)
EP (1) EP2470596B1 (enExample)
JP (1) JP5808330B2 (enExample)
KR (1) KR101907698B1 (enExample)
CN (1) CN102666697B (enExample)
BR (1) BR112012007261B1 (enExample)
CA (1) CA2775574C (enExample)
MX (1) MX2012003940A (enExample)
TW (1) TW201134853A (enExample)
WO (1) WO2011041372A1 (enExample)

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WO2013048752A1 (en) * 2011-09-30 2013-04-04 Dow Global Technologies Llc Plasticizer for low temperature unwind with weight retention during heat aging
WO2013119402A1 (en) * 2012-02-08 2013-08-15 Dow Global Technologies Llc Plasticizer compositions and methods for making plasticizer compositions
US8557139B2 (en) 2008-02-15 2013-10-15 Dow Global Technologies Llc Replacement plasticizer system for phthalate-plasticized formulations
US8697787B2 (en) 2009-09-30 2014-04-15 Dow Global Technologies Llc Flexible PVC compositions made with plasticizers derived from renewable sources
US8822578B2 (en) 2009-09-30 2014-09-02 Dow Global Technologies Llc Purified acetylated derivatives of castor oil and compositions including same
US8859654B2 (en) 2009-09-30 2014-10-14 Dow Global Technologies Llc Heat stabilized polymeric composition with epoxidized fatty acid ester plasticizer
US9181415B2 (en) 2009-09-30 2015-11-10 Dow Global Technologies Llc Acetylated derivatives of castor oil and their blends with epoxidized fatty acid esters
US9228155B2 (en) 2010-07-28 2016-01-05 Dow Global Technologies Llc Plasticizers made from oil extracted from microorganisms and polar polymeric compositions comprising the same
US9394425B2 (en) 2012-06-22 2016-07-19 Dow Global Technologies Llc Acetylated polyol hydroxystearate plasticizers and plasticized polymeric compositions
US9422418B2 (en) 2009-09-30 2016-08-23 Dow Global Technologies Llc Acetylated monoglyceride of 12-hydroxystearic acid and blends with epoxidized fatty acid esters
US9499681B2 (en) 2012-11-12 2016-11-22 Dow Global Technologies Llc Epoxidized fatty acid alkyl ester plasticizers and methods for making epoxidized fatty acid alkyl ester plasticizers
US9593091B2 (en) 2012-11-12 2017-03-14 Dow Global Technologies Llc Methods for making epoxidized fatty acid alkyl esters
US9850366B2 (en) 2012-10-18 2017-12-26 Dow Global Technologies Llc Epdxidized fatty acid alkyl ester plasticizers and methods for making epdxidized fatty acid alkyl ester plasticizers
US10100172B2 (en) 2012-06-26 2018-10-16 Dow Global Technologies Llc Plasticizers and plasticized polymeric compositions
US10626248B2 (en) 2012-12-29 2020-04-21 Saint-Gobain Performance Plastics Corporation Flexible tube

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BRPI0705621B1 (pt) * 2007-12-10 2019-04-09 Nexoleum Bioderivados Ltda. Composição plastificte de pvc
CA2850326C (en) * 2011-09-30 2019-11-12 Dow Global Technologies Llc Process for mixing polyvinyl chloride with a bio-based plasticizer
CN102964748B (zh) * 2012-12-20 2014-09-10 中国林业科学研究院林产化学工业研究所 一剂多效的油脂基pvc热稳定剂及其制备方法
US9685255B2 (en) * 2013-03-11 2017-06-20 Dow Global Technologies Llc Synergistic blends of calcium carbonate and calcined clay
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FR3010409B1 (fr) * 2013-09-11 2017-12-22 Total Marketing Services Plastifiant pour mastics, plastisols et adhesifs
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