CA2617786A1 - Polyvinyl chloride compositions - Google Patents

Polyvinyl chloride compositions Download PDF

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Publication number
CA2617786A1
CA2617786A1 CA002617786A CA2617786A CA2617786A1 CA 2617786 A1 CA2617786 A1 CA 2617786A1 CA 002617786 A CA002617786 A CA 002617786A CA 2617786 A CA2617786 A CA 2617786A CA 2617786 A1 CA2617786 A1 CA 2617786A1
Authority
CA
Canada
Prior art keywords
phthalate
butyl
adipate
plasticizer
terephthalate
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.)
Granted
Application number
CA002617786A
Other languages
French (fr)
Other versions
CA2617786C (en
Inventor
David Justin Olsen
Martin James Stimpson
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.)
Eastman Chemical Co
Original Assignee
Eastman Chemical Company
David Justin Olsen
Martin James Stimpson
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 Eastman Chemical Company, David Justin Olsen, Martin James Stimpson filed Critical Eastman Chemical Company
Publication of CA2617786A1 publication Critical patent/CA2617786A1/en
Application granted granted Critical
Publication of CA2617786C publication Critical patent/CA2617786C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C08K5/092—Polycarboxylic 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/12—Esters; Ether-esters of cyclic polycarboxylic 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
    • C08K5/04—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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Sealing Material Composition (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Organic Insulating Materials (AREA)
  • Cosmetics (AREA)
  • Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Paints Or Removers (AREA)

Abstract

A polyvinyl chloride composition having polyvinyl chloride resin and a plasticizer ester selected from di-butyl terephthalate, di-isobutyl terephthalate, or mixtures thereof.

Claims (12)

1. A polyvinyl chloride (PVC) composition comprising an admixture of a PVC
resin and a plasticizer selected from the group consisting of di-butyl terephthalate, di-isobutyl terephthalate and mixtures thereof.
2. The PVC composition according to Claim 1 wherein an amount of plasticizer in the composition is from 20 to 800 parts plasticizer per 100 parts PVC resin.
3. The PVC composition according to Claim 2 wherein the amount of plasticizer in the composition is from 40 to 120 parts plasticizer per 100 parts PVC resin.
4. The PVC composition according to Claim 2 further comprising an additional plasticizer selected from the group consisting of dioctyl phthalate, di-2-ethyl hexyl phthalate, diisooctyl phthalate, diisononyl phthalate, di-linear nonyl phthalate, di-linear nonyl, undecyl phthalate, di-linear undecyl phthalate, diundecyl phthalate, diisodecylpthalate, C6-C10 straight-chain phthalates, C7 linear phthalate, C9 linear phthalate, C11 linear phthalate, ditridecyl phthalate, undecyl dodecyl phthalate, di(2-propylheptyl phthalate), nonylundecyl phthalate, texanolbenzylphthalate, polyester phthalate, diallylphthalate, n-butylphthalyl-n-butyl glycosate, dicaprylphthalate, butylcyclohexyl phthalate, dicyclohexyl phthalate, butyl octyl phthalate, dioctyl terephthalate, di-2-ethyl hexyl terephthalate, dioctyl adipate, di-2-ethyl hexyl adipate, diisonyl adipate, diisooctyl adipate, diisodecyl adipate, di tridecyl adipate, dibutoxyethyl adipate, dibutoxyethoxy adipate, di(noctyl, ndecyl)adipate, polyester adipate, poly glycol adipates, trioctyl trimellitate, tri-2-ethyl hexyl trimellitate, triisooctyl trimellitate, tri isononyl trimellitate, triisodecyl trimellitate, tri-n-hexyl trimellitate, dioctyl azelate, di-2-ethylhexyl glutarate, di-2-ethyl hexyl sebecate, dibutyl sebecate, dibutoxyethyl sebecate, triethyl citrate, acetyl triethyl citrate, tri-n-butyl citrate, acetytri-n-butyl citrate, acetyltri-n-hexyl citrate, n-butyl tri-n-hexyl citrate, isononyl benzoate, isodecyl benzoate, 1,4 cyclohexane dimethanol dibenzoate, 2,2,4 trimethyl-1,3 pentane diol dibenzoate, 2,2,-dimethyl-1,3 propanediol dibenzoate, C10-C21 alkane phenol esters or alkyl sulphonic phenol ester, acetic acid reaction products with fully hardened castor oil, pentaerythritol tetrabenzoate, glycerol tribenzoate, polypropylene glycol dibenzoate, triarylphosphates, diisononyl cyclohexane 1,2 dicarboxylate, polymers of adipic acid/phthalates/adipates/sebecates/ with glycols and often acid terminated, butyl benzyl phthalate, alkylbenzyl phthalate, C7-C9 butyl phthalate, diethylene glycol dibenzoate, di propylene glycol dibenzoate, 2-ethylhexyl benzoate, texanolbenzoate, ethylene glycol dibenzoate, propylene glycol dibenzoate, triethylene glycol dibenzoate, di-heptyl phthalate, dihexyl phthalate, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, diisobutyl phthalate, and mixtures thereof, and wherein 10 to 100 weight percent of said plasticizer is di-butyl terepbthalate, di-isobutyl terephthalate or a mixture thereof.
5. The PVC composition according to Claim 4 wherein the amount of plasticizer in the composition is from 40 to 120 parts plasticizer per 100 parts PVC resin and wherein 5 to 100 weight percent of said plasticizer is di-butyl terephthalate, di-isobutyl terephthalate or a mixture thereof.
6. A polyvinyl chloride (PVC) composition comprising an admixture of a PVC
resin and a plasticizer selected from the group consisting of di-butyl terephthalate, di-isobutyl terephthalate and a mixture thereof and a stabilizing amount of a stabilizer selected from the group consisting metal soaps, organic phosphites, epoxy compounds, tin stabilizers, and mixtures thereof.
7. A polyvinyl chloride (PVC) composition comprising an admixture of (i) a PVC

resin; (ii) 20 to 800 parts plasticizer selected from the group consisting of di-butyl terephthalate, di-isobutyl terephthalate and mixtures thereof per 100 parts PVC resin and (iii) a stabilizer mixture selected from the group consisting of barium stearate/zinc stearate and epoxy soybean oil, calcium stearate/zinc stearate and epoxy soybean oil, and barium stearate/cadmium stearate and epoxy soybean oil.
8. The PVC composition according to Claim 7 wherein the plasticizer further includes an additional plasticizer selected from the group consisting of dioctyl phthalate, di-2-ethyl hexyl phthalate, diisooctyl phthalate, diisononyl phthalate, di-linear nonyl phthalate, di-linear nonyl, undecyl phthalate, di-linear undecyl phthalate, diundecyl phthalate, diisodecylpthalate, C6-C10 straight-chain phthalates, C7 linear phthalate, C9linear phthalate, C11 linear phthalate, ditridecyl phthalate, undecyl dodecyl phthalate, di(2-propylheptyl phthalate), nonylundecyl phthalate, texanolbenzylphthalate, polyester phthalate, diallylphthalate, n-butylphthalyl-n-butyl glycosate, dicaprylphthalate, butylcyclohexyl phthalate, dicyclohexyl phthalate, butyl octyl phthalate, dioctyl terephthalate, di-2-ethyl hexyl terephthalate, dioctyl adipate, di-2-ethyl hexyl adipate, diisonyl adipate, diisooctyl adipate, diisodecyl adipate, di tridecyl adipate, dibutoxyethyl adipate, dibutoxyethoxy adipate, di(noctyl, ndecyl)adipate, polyester adipate, poly glycol adipates, trioctyl trimellitate, tri-2-ethyl hexyl trimellitate, triisooctyl trimellitate, tri isononyl trimellitate, triisodecyl trimellitate, tri-n-hexyl trimellitate, dioctyl azelate, di-2-ethylhexyl glutarate, di-2-ethyl hexyl sebecate, dibutyl sebecate, dibutoxyethyl sebecate, triethyl citrate, acetyl triethyl citrate, tri-n-butyl citrate, acetytri-n-butyl citrate, acetyltri-n-hexyl citrate, n-butyl tri-n-hexyl citrate, isononyl benzoate, isodecyl benzoate, 1,4 cyclohexane dimethanol dibenzoate, 2,2,4 trimethyl-1,3 pentane diol dibenzoate, 2,2,-dimethyl-1,3 propanediol dibenzoate, C10-C21 alkane phenol esters or alkyl sulphonic phenol ester, acetic acid reaction products with fully hardened castor oil, pentaerythritol tetrabenzoate, glycerol tribenzoate, polypropylene glycol dibenzoate, triarylphosphates, diisononyl cyclohexane 1,2 dicarboxylate, polymers of adipic acid/phthalates/adipates/sebecates/ with glycols and often acid terminated, butyl benzyl phthalate, alkylbenzyl phthalate, C7-C9 butyl phthalate, diethylene glycol dibenzoate, di propylene glycol dibenzoate, 2-ethylhexyl benzoate, texanolbenzoate, ethylene glycol dibenzoate, propylene glycol dibenzoate, triethylene glycol dibenzoate, di-heptyl phthalate, dihexyl phthalate, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, diisobutyl phthalate, and mixtures thereof, and wherein10 to 100 weight percent of the plasticizer is selected from the group consisting of di-butyl terephthalate, di-isobutyl terephthalate and mixtures thereof.
9. The PVC composition according to Claim 8 wherein the amount of plasticizer is from 40 to 120 parts plasticizer per 100 parts PVC resin and wherein 25 to 100 weight percent of the plasticizer is selected from the group consisting of di-butyl terephthalate, di-isobutyl terephthalate and mixtures thereof.
10. A polyvinyl chloride (PVC) composition comprising an admixture of (i) a PVC
resin; (ii) 20 to 800 parts plasticizer per 100 parts PVC resin wherein the plasticizer is selected from the group consisting of di-butyl terephthalate, di-isobutyl terephthalate and mixtures thereof; and (iii) a stabilizer mixture selected from the group consisting of barium stearate/zinc stearate and epoxy soybean oil, calcium stearate/zinc stearate and epoxy soybean oil, and barium stearate/cadmium stearate and epoxy soybean oil.
11. The PVC composition according to Claim 10 wherein the amount of plasticizer in the composition is from 40 to 120 parts plasticizer per 100 parts PVC resin.
12. An article of manufacture comprising the composition of any one of claims 1 to 11 wherein the article of manufacture is selected from the group consisting of adhesives, sealants, coated fabrics, wire coatings, cable coatings, foams, footwear, gaskets, inks, cosmetics, medical devices, floor coverings, wallpaper, roofing membranes, tubing, inks, and calendared films.
CA2617786A 2005-08-12 2006-08-10 Polyvinyl chloride compositions Expired - Fee Related CA2617786C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/202,543 US8372912B2 (en) 2005-08-12 2005-08-12 Polyvinyl chloride compositions
US11/202,543 2005-08-12
PCT/US2006/031465 WO2007021987A1 (en) 2005-08-12 2006-08-10 Polyvinyl chloride compositions

Publications (2)

Publication Number Publication Date
CA2617786A1 true CA2617786A1 (en) 2007-02-22
CA2617786C CA2617786C (en) 2011-07-12

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CA2617786A Expired - Fee Related CA2617786C (en) 2005-08-12 2006-08-10 Polyvinyl chloride compositions

Country Status (7)

Country Link
US (2) US8372912B2 (en)
EP (1) EP1913069A1 (en)
JP (3) JP5442992B2 (en)
CN (1) CN101238175B (en)
CA (1) CA2617786C (en)
NO (1) NO20081219L (en)
WO (1) WO2007021987A1 (en)

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US20070037926A1 (en) 2007-02-15
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CN101238175A (en) 2008-08-06

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