WO2000058393A1 - Low emission polymer compositions - Google Patents

Low emission polymer compositions Download PDF

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Publication number
WO2000058393A1
WO2000058393A1 PCT/US2000/005604 US0005604W WO0058393A1 WO 2000058393 A1 WO2000058393 A1 WO 2000058393A1 US 0005604 W US0005604 W US 0005604W WO 0058393 A1 WO0058393 A1 WO 0058393A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymer
stabilizing compound
organic nitrogen
melt stable
acrolein
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/US2000/005604
Other languages
English (en)
French (fr)
Inventor
Joseph Varapadavil Kurian
Jing Chung Chang
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to CA002362383A priority Critical patent/CA2362383C/en
Priority to AT00916044T priority patent/ATE272677T1/de
Priority to EP00916044A priority patent/EP1171520B1/en
Priority to BR0010764-6A priority patent/BR0010764A/pt
Priority to JP2000608683A priority patent/JP4716576B2/ja
Priority to DE60012722T priority patent/DE60012722T2/de
Priority to MXPA01009775A priority patent/MXPA01009775A/es
Publication of WO2000058393A1 publication Critical patent/WO2000058393A1/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
    • C08K5/16—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/88—Post-polymerisation treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds

Definitions

  • the invention concerns polymer compositions that exhibit reduced levels of degradation product emissions during processing. This invention further concerns processes for the fabrication of polymer articles with low emissions of polymer degradation products.
  • TECHNICAL BACKGROUND 3-Hydroxypropanoxy terminated polymers have the problem of being prone to thermal degradation processes that result in acrolein emissions.
  • Acrolein is an irritant chemical, for which workplace levels are strictly regulated, i.e. to limit its content in the air to be less than 0.1 ppm [AEL].
  • the present invention solves this problem by providing compositions comprising 3-hydroxypropanoxy terminated polymers of improved stability with regard to acrolein emission.
  • the present invention comprises compositions prepared by contacting molten 3-hydroxypropanoxy terminated polymer with an effective amount of a melt stable, organic nitrogen-containing stabilizing compound to reduce the emission of acrolein from said molten polymer.
  • This invention also comprises a process for the fabrication of polymer articles from 3-hydroxypropanoxy terminated polymers exhibiting low levels of acrolein emissions, which process comprises: a) contacting in the molten state said 3-hydroxypropanoxy terminated polymer with an effective amount of a melt stable, organic nitrogen-containing stabilizing compound to reduce the emission of acrolein from said polymer in the molten state, and b) fabricating said polymer into said article.
  • 3-Hydroxypropanoxy terminated polymers comprise those polymers prepared from 1,3-propanediol or its chemical equivalents.
  • the 1,3-propanediol can be prepared chemically or biologically.
  • 3-hydroxypropanoxy terminated polymers includes, but is not limited to 1,3- propanediol dicarboxylate polymer, examples of which include poly(trimethylene terephthalate, poly(trimethylene naphthalenedicarboxylate), poly(trimethylene isophthalate) and blends and copolymers thereof.
  • dicarboxylic acids useable in the 3-hydroxypropanoxy terminated polymers include 1 ,4-cyclohexane dicarboxylic acid, 1,3-cyclohexane dicarboxylic acid, succinic acid, glutaric acid, adipic acid, sebacic acid and 1,12-dodecane dioic acid.
  • the dicarboxylic acids may be introduced to the polymerization process as the dicarboxylic acids or as the lower dialkyl esters of the dicarboxylic acids, for example, the dimethyl, diethyl, or dipropyl esters of these dicarboxylic acids.
  • Copolymers useable with the polymers of the present invention typically comprise any of the dicarboxylic acids mentioned above and diols other than 1,3- propanediol, for example, up to 30 mol% of such other diol, based on the total moles of diol present.
  • diols include ethylene glycol, 1 ,4-butane diol,
  • the blend polymer can be prepared from any of the diacids or the diols listed above.
  • a specifically preferred blend comprises poly(ethylene terephthalate) and poly(trimethylene terephthalate).
  • polymers have a high molecular weight so as to be commercially useful.
  • molecular weight can be characterized by the polymer having an intrinsic viscosity (IV) of at least 0.1 dl/g, determined by measuring the flow time of a solution of known polymer concentration and the flow time of the polymer solvent in a capillary viscometer, as set forth in ASTM D2857.95
  • the polymer can be a homopolymer or blends and copolymers containing at least 10% of one or more 3-hydroxypropanoxy terminated polymer.
  • a blend comprising 90% poly(ethylene terephthalate) and 10% poly(trimethylene terephthalate) - (containing up to 1 weight % of a polyamide polymer as the stabilizing compound), is within the envisioned scope of the present invention.
  • the melt stable, organic nitrogen-containing stabilizing compound with which the 3-hydroxypropanoxy terminated polymer is intimately blended is selected from melt stable primary, secondary and tertiary amines, either aliphatic or aromatic, and aliphatic or aromatic amides. Also included are polymers containing such functional groups either as a polymer side chain or in the polymer backbone, e.g., polyamides, and copolymers and blends of polyamides.
  • linear polyamides When polyamides are employed, they can be linear or branched in chain structure.
  • linear polyamides include, monomeric polyamides, such as poly(caprolactam), nylon 6, and bis monomeric polyamides, such as poly(hexamethylenediamine adipate), nylon 4,6, nylon 6,6, nylon 6,10, nylon 6,12, nylon 12,12, or their copolymers and blends.
  • Certain aromatic polyamides for example poly(p-phenylene terephthalamide) and poly(m-phenylene isophthalamide), can also be employed.
  • Polyamides prepared from the use of tri-, tetra- or multifunctional amines, e.g., bis(hexamthylenetriamine) or BHMT can also be used.
  • the stabilizing compound contains nitrogen and be stable in the polymer melt.
  • the stabilizing compound will also be in the liquid state in the melt of 3-hydroxypropanoxy terminated polymer so as to be intimately mixed with the polymer.
  • the compound is of sufficient molecular weight so as to achieve stability in molten 3- hydroxypropanoxy terminated polymer, in which case, the liquid state of the compound will be the molten state.
  • the stabilizing should also not introduce or cause color in the polymer.
  • Polyamides such as described above fulfill all of these characteristics and thus are a preferred class of stabilizing compounds.
  • the nitrogen functionality in the melt stable, organic nitrogen-containing stabilizing compound either interacts with the 3-hydroxypropanoxy terminus of the polymer chain, or a degradation product thereof, to hinder or stop degradative pathways that generate acrolein or interacts with generated acrolein on the molecular level to hinder or prevent emission.
  • the reactions between amines (primary, secondary, and tertiary) and aldehydes giving different adducts is well documented in literature. For a review of the reactions between amines and aldehydes, See Rec. Chem. Prog., 29, 85-101 (1968).
  • the amount of melt stable, organic nitrogen-containing stabilizing compound present in the composition of the present invention is defined as an amount to be effective in the reduction of acrolein emission. This is generally less than 10% by weight based on the amount of the 3-hydroxypropanoxy terminated polymer present. One percent by weight has been demonstrated to be effective. The range of effective amounts can be from about 0.01% to about 10% by weight.
  • Articles of manufacture prepared from 3-hydroxypropanoxy terminated polymers, copolymers and blends can include fibers (monocomponent, bicomponent, for example bicomponent with poly(ethylene terephthalate, or multicomponent), filaments, films, castings and moldings.
  • the manufacture of these articles generally require the starting polymer to be in molten form at some stage of the manufacturing process. It is during this molten stage that acrolein emission is most prevalent.
  • composition comprising the 3-hydroxypropanoxy terminated polymer and the melt stable, organic nitrogen-containing stabilizing compound
  • the composition comprising the 3-hydroxypropanoxy terminated polymer and the melt stable, organic nitrogen-containing stabilizing compound can be formed from the 3-hydroxypropanoxy terminated polymer in flake or pellet form mixed with the melt stable, organic nitrogen-containing stabilizing compound in solid form.
  • the resulting mixture can then be melt processed, i.e., in an extruder, to form the intimate polymer mixture.
  • the melt stable, organic nitrogen-containing stabilizing compound can be introduced into and mixed with a molten stream of 3-hydroxypropanoxy terminated polymer.
  • organic nitrogen-containing stabilizing compound In the case where a polyamide or copolyamide or polyamide blend is used as the melt stable, organic nitrogen-containing stabilizing compound, this material can be dry blended with the 3-hydroxypropanoxy terminated polymer prior to processing or fed as a melt into a melt of the 3-hydroxypropanoxy terminated polymer. Oligomers containing the nitrogen functionality of the melt stable, organic nitrogen- containing stabilizing compound may also be mixed into a melt of the 3- hydroxypropanoxy terminated polymer. The solid phasing of 3- hydroxypropanoxy terminated oligomers can occur in presence of an oligomeric or polymeric nitrogen containing stabilizing compound In all of these cases, the 3- hydroxypropanoxy terminated polymer and stabilizing compound are in contact with one another when the former is in the molten state.
  • the resultant article fabricated from this melt is then not accompanied by the presence of a detrimental amount of acrolein in the surrounding atmosphere.
  • spinning tests were conducted in a spinning assembly comprising a conditioning vessel, a screw assembly, a spinning pack comprising a 1050 hole staple spinneret, 39 pounds (17.7 kg) per hour throughput and a polymer residence time about 5 minutes.
  • the screw was shutdown and the conditioner vessel was cleaned before charging each polymer item.
  • Each polymer item was conditioned for 30 minutes using 160°C recirculating gas before the screw was started up. All samples were taken 30 minutes after the screw system was stable.
  • NIOSH method NIOSH 2532M was used for the acrolein measurements.
  • Example Polymer Nylon 6 Sample Acrolein Cone. No. Temp°C wt % Volume liters* ⁇ g Ppm

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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)
  • Artificial Filaments (AREA)
  • Polyamides (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Polyesters Or Polycarbonates (AREA)
PCT/US2000/005604 1999-03-31 2000-03-02 Low emission polymer compositions Ceased WO2000058393A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CA002362383A CA2362383C (en) 1999-03-31 2000-03-02 Low emission polymer compositions
AT00916044T ATE272677T1 (de) 1999-03-31 2000-03-02 Polymerzusammensetzung mit niedriger emission
EP00916044A EP1171520B1 (en) 1999-03-31 2000-03-02 Low emission polymer compositions
BR0010764-6A BR0010764A (pt) 1999-03-31 2000-03-02 Composição polimérica de baixa emissão de produtos de degradação e processo de fabricação de artigos poliméricos
JP2000608683A JP4716576B2 (ja) 1999-03-31 2000-03-02 低放出性ポリマー組成物
DE60012722T DE60012722T2 (de) 1999-03-31 2000-03-02 Polymerzusammensetzung mit niedriger emission
MXPA01009775A MXPA01009775A (es) 1999-03-31 2000-03-02 Composiciones polimericas de baja emision.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US12708099P 1999-03-31 1999-03-31
US60/127,080 1999-03-31
US09/505,785 US6331264B1 (en) 1999-03-31 2000-02-17 Low emission polymer compositions
US09/505,785 2000-02-17

Publications (1)

Publication Number Publication Date
WO2000058393A1 true WO2000058393A1 (en) 2000-10-05

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PCT/US2000/005604 Ceased WO2000058393A1 (en) 1999-03-31 2000-03-02 Low emission polymer compositions

Country Status (15)

Country Link
US (1) US6331264B1 (enExample)
EP (1) EP1171520B1 (enExample)
JP (1) JP4716576B2 (enExample)
KR (1) KR100603472B1 (enExample)
CN (1) CN1208382C (enExample)
AR (1) AR028990A1 (enExample)
AT (1) ATE272677T1 (enExample)
BR (1) BR0010764A (enExample)
CA (1) CA2362383C (enExample)
DE (1) DE60012722T2 (enExample)
ES (1) ES2225114T3 (enExample)
ID (1) ID30325A (enExample)
MX (1) MXPA01009775A (enExample)
TR (1) TR200102807T2 (enExample)
WO (1) WO2000058393A1 (enExample)

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WO2001034693A3 (en) * 1999-11-12 2001-11-22 Du Pont Acid dyeable polyester compositions
US6713653B2 (en) 2001-08-24 2004-03-30 E. I. Du Pont De Nemours And Company Polyamines and polymers made therewith
US6723799B2 (en) 2001-08-24 2004-04-20 E I. Du Pont De Nemours And Company Acid-dyeable polymer compositions
KR100704807B1 (ko) * 2003-03-17 2007-04-09 아사히 가세이 케미칼즈 가부시키가이샤 폴리트리메틸렌 테레프탈레이트 조성물과 그의 제조 방법
US7785507B2 (en) 2004-04-30 2010-08-31 E. I. Du Pont De Nemours And Company Spinning poly(trimethylene terephthalate) yarns
WO2018039896A1 (en) * 2016-08-30 2018-03-08 Dow Global Technologies Llc Method of attenuating concentration of acrolein

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EP1347005A1 (en) * 2002-03-23 2003-09-24 Zimmer AG Polytrimethylene terephtalate resins with improved properties
JP2006511726A (ja) * 2002-12-23 2006-04-06 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ポリ（トリメチレンテレフタレート）複合繊維方法
US7005093B2 (en) * 2003-02-05 2006-02-28 E. I. Du Pont De Nemours And Company Spin annealed poly(trimethylene terephthalate) yarn
US7342142B2 (en) * 2003-05-06 2008-03-11 E.I. Du Pont De Nemours And Company Hydrogenation of polytrimethylene ether glycol
US7323539B2 (en) * 2003-05-06 2008-01-29 E. I. Du Pont De Nemours And Company Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality
US7084311B2 (en) * 2003-05-06 2006-08-01 E. I. Du Pont De Nemours And Company Hydrogenation of chemically derived 1,3-propanediol
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US7388115B2 (en) * 2006-01-20 2008-06-17 E. I. Du Pont De Nemours And Company Manufacture of polytrimethylene ether glycol
US20070203371A1 (en) * 2006-01-23 2007-08-30 Sunkara Hari B Process for producing polytrimethylene ether glycol
US20080039582A1 (en) * 2006-07-28 2008-02-14 Hari Babu Sunkara Polytrimethylene ether-based polyurethane ionomers
US7531593B2 (en) 2006-10-31 2009-05-12 E.I. Du Pont De Nemours And Company Thermoplastic elastomer blend composition
US20080108845A1 (en) * 2006-11-07 2008-05-08 Hari Babu Sunkara Polytrimethylene ether glycol esters
US20080135662A1 (en) * 2006-12-06 2008-06-12 Chang Jing C Melt-spun elastoester multifilament yarns
US7714174B2 (en) * 2007-03-27 2010-05-11 E. I. Du Pont De Nemours And Company Lower-color polytrimethylene ether glycol using hydride compounds
JP2010537001A (ja) * 2007-08-24 2010-12-02 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 潤滑油組成物
BRPI0815293A2 (pt) * 2007-08-24 2017-05-09 Du Pont "composição de óleo lubrificante"
EP2181182A1 (en) * 2007-08-24 2010-05-05 E. I. du Pont de Nemours and Company Lubrication oil compositions
BRPI0815243A2 (pt) * 2007-08-24 2019-09-24 Du Pont composição de óleo lubrificante
US8703681B2 (en) 2007-08-24 2014-04-22 E I Du Pont De Nemours And Company Lubrication oil compositions
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US6858702B2 (en) 1999-11-12 2005-02-22 Invista North America S.á.r.l. Polyamide compounds
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WO2018039896A1 (en) * 2016-08-30 2018-03-08 Dow Global Technologies Llc Method of attenuating concentration of acrolein
KR20190046864A (ko) * 2016-08-30 2019-05-07 다우 글로벌 테크놀로지스 엘엘씨 아크롤레인의 농도의 저감 방법
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EP1171520B1 (en) 2004-08-04
US6331264B1 (en) 2001-12-18
ES2225114T3 (es) 2005-03-16
EP1171520A1 (en) 2002-01-16
CA2362383C (en) 2009-05-05
CN1348479A (zh) 2002-05-08
DE60012722T2 (de) 2005-08-04
AR028990A1 (es) 2003-06-04
CN1208382C (zh) 2005-06-29
CA2362383A1 (en) 2000-10-05
KR20020005652A (ko) 2002-01-17
TR200102807T2 (tr) 2002-07-22
JP4716576B2 (ja) 2011-07-06
DE60012722D1 (de) 2004-09-09
KR100603472B1 (ko) 2006-07-24
BR0010764A (pt) 2002-01-15
JP2003523414A (ja) 2003-08-05
MXPA01009775A (es) 2002-05-14
ID30325A (id) 2001-11-22

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