EP1828311A2 - Copolymeres sequences de terephtalate de polyethylene et de polyamide constitue de meta-xylylene diamine et d'acide adipique - Google Patents

Copolymeres sequences de terephtalate de polyethylene et de polyamide constitue de meta-xylylene diamine et d'acide adipique

Info

Publication number
EP1828311A2
EP1828311A2 EP05825926A EP05825926A EP1828311A2 EP 1828311 A2 EP1828311 A2 EP 1828311A2 EP 05825926 A EP05825926 A EP 05825926A EP 05825926 A EP05825926 A EP 05825926A EP 1828311 A2 EP1828311 A2 EP 1828311A2
Authority
EP
European Patent Office
Prior art keywords
polyethylene terephthalate
polyamide
meta
xylylenediamine
acid
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Withdrawn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
EP05825926A
Other languages
German (de)
English (en)
Inventor
Joachim Strauch
Paul-Michael Bever
Freddy Gruber
Volker Warzelhan
Bernhard Rosenau
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1828311A2 publication Critical patent/EP1828311A2/fr
Withdrawn legal-status Critical Current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
    • 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
    • C08G63/91—Polymers modified by chemical after-treatment
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides
    • 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
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/181—Acids containing aromatic rings
    • C08G63/183—Terephthalic acids
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/48—Polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/12—Polyester-amides

Definitions

  • the present invention relates to block copolymers of polyethylene terephthalate and the polyamide of meta-xylylenediamine and adipic acid and to processes for their preparation.
  • the present invention was therefore based on the object to remedy the aforementioned disadvantages.
  • block copolymers of polyethylene terephthalate and the polyamide of meta-xylylenediamine and adipic acid have been found. Furthermore, a new and improved process for the preparation of block copolymers of polyethylene terephthalate and the polyamide from meta-xylylenediamine and adipic acid was found, which is characterized in that at a relative solution viscosity of 1, 5 to 2.2 polyethylene terephthalate at a pressure of 0, 1 to 20 bar and a temperature of 245 ° C to 300 0 C inflicts.
  • the components meta-xylylenediamine, adipic acid and water are separated or as any mixtures, preferably as a mixture of all three components batchwise or preferably continuously at a pressure of 2 to 20 bar, preferably 5 to 15 bar, particularly preferably 7 to 12 bar and a temperature of 170 to 280 0 C, preferably 180 to 27O 0 C, more preferably 190 to 26O 0 C, in particular 200 to 25O 0 C implement.
  • As starting mixtures preferably between 30 to 80 wt .-% solutions of the salt compound of meta-xylylenediamine and adipic acid, in particular between 45 to 70 wt .-% solutions used.
  • the postcondensation or molten polyamide directly preferably the postcondensation at a pressure of 0.1 to 3 bar, preferably 0.5 to 2 bar, more preferably 0.7 to 1, 5 bar, in particular at atmospheric pressure (atmospheric pressure) under inert gas such as nitrogen or argon, preferably nitrogen and a temperature of 240 to 300 0 C, preferably 250 to 290 0 C, more preferably 260 to 28O 0 C are performed.
  • the addition of the polyethylene terephthalate to the polyamide can be carried out generally at a pressure of 0.1 to 20 bar and a temperature of 240 to 300 ° C, preferably 245 to 300 ° C. In a preferred embodiment, the addition of the polyethylene terephthalate is added in the production process of the polyamide.
  • the molar ratio of meta-xylylenediamine to adipic acid can be varied within wide limits, is usually at 1, 5: 1 to 0.75: 1, preferably from 1, 2: 1 to 0.8: 1, particularly preferably 1 , 1: 1 to 0.9: 1 or equimolar (1: 1), especially at 1, 05: 1 to 0.95: 1.
  • the molar ratio of meta-xylylenediamine to adipic acid is usually from 1.5: 1 to 1: 1, preferably from 1.2: 1 to 1.01: 1, more preferably at 1.1: 1 to 1.02: 1, especially at 1.05: 1 to 1.01: 1.
  • the molar ratio of diprotic acid to meta-xylylenediamine is generally from 1.5: 1 to 1: 1, preferably from 1.2: 1 to 1:01: 1, particularly preferably at 1, 1: 1 to 1, 02: 1, in particular at 1, 05: 1 to 1, 01: 1.
  • One embodiment of the condensation of meta-xylylenediamine and adipic acid is that the polycondensations can be carried out batchwise in a steel autoclave at a pressure between 1 and 20 bar.
  • the starting materials can be used in a 30 to 80 wt .-% solution in water.
  • a further embodiment consists in that the polycondensations can be carried out continuously at a pressure of 1 to 20 bar.
  • the polycondensation plant can consist of a batch kettle, evaporator reactor, separator and a granulation unit.
  • the starting materials can be used in a 30 to 80% strength by weight solution in water.
  • the residual monomer content in the block copolymer according to the invention is generally up to 500 ppm, for example 0.1 to 500 ppm, preferably 0.5 to 50 ppm, more preferably between 1 to 15 ppm of meta-xylylenediamine.
  • the residual monomer content of adipic acid is generally below 10 ppm.
  • the content of cyclic dimer (MXDA + adipic acid) in the block copolymer according to the invention is generally up to 1500 ppm, such as 10 to 1500 ppm, preferably 50 to 1000 ppm, particularly preferably 100 to 250 ppm.
  • polyamides are generally all polyamides, usually those which are from 50 to 100 wt .-%, preferably 70 to 100 wt .-%, particularly preferably 85 to 100 wt .-% meta-xylylenediamine and 50 to 100 Wt .-%, preferably 70 to 100 wt .-%, particularly preferably 85 to 100 wt .-% adipic acid and 0 to 50 wt .-%, preferably 0 to 30 wt .-%, particularly preferably 0 to 15 wt.
  • % of the corresponding comonomers and / or optionally chain regulators and / or optionally stabilizers are degraded, having a molecular weight Mn of 10,000 to 50,000, preferably high molecular weight polyamides having a molecular weight Mn of 30,000 to 40,000 or low molecular weight polyamides having a molecular weight Mn from 11,000 to 22,000 , Particularly preferably low molecular weight polyamides having a molecular weight Mn of 13000 to 20,000, in particular low molecular weight polyamides having a molecular weight Mn of ⁇ 15,000 to 19,000.
  • the molecular weight determination is carried out by GPC analogous to DIN 55672-1 with an apparatus which consists of the HPLC pump 420 from Kontron Instruments, an autosampler from Gilson Abimed, a UV photometer LCD (at 230 / D) from Gamma Analysentechnik and a Differential refractometer G1362A from Agilent exists.
  • the eluent used was a mixture of hexafluoroisopropanol and 0.05% trifluoroacetic acid potassium salt.
  • the company Polymer Labo- ratories used a precolumn HFIP Gel (inner diameter: 7.5 mm, length 5 cm) and an HFIP Gel Unear column (inner diameter: 7.5 mm, length 5 cm).
  • the column temperature was 40 ° C. and the flow rate 0.5 ml / min.
  • the samples with a density of 1.5 g / l were previously filtered through Millipore Millex FG (pore size 0.2 [ ⁇ m]).
  • Millipore Millex FG pore size 0.2 [ ⁇ m]
  • the relative solution viscosity of the polyamide was carried out with samples of 1 g of polyamide in 100 ml of 96% strength by weight sulfuric acid and the measurement was carried out using an Ubbelohde viscometer 2 type 50120 (Schott) according to DIN EN ISO 1628-1.
  • Suitable comonomers of meta-xylylenediamine are, for example, aliphatic, aromatic or arylaliphatic diamines such as ethylenediamine, butylenediamine, pentamethylenediamine, hexamethylenediamine, cyclohexanediamine, octamethylenediamine, bis (4,4-aminocyclohexyl) methane, bis (4,4-amino-3, 3-methylcyclohexyl) methane, bis (amino) cyclohexane, para-phenylenediamine, ortho-xylylenediamine and para-xylylenediamine.
  • diamines such as ethylenediamine, butylenediamine, pentamethylenediamine, hexamethylenediamine, cyclohexanediamine, octamethylenediamine, bis (4,4-aminocyclohexyl) methane, bis (4,4-
  • Suitable comonomers of adipic acid are, for example, aliphatic, aromatic or arylaliphatic dicarboxylic acids such as terephthalic acid, isophthalic acid, sulfoisophthalic acid, naphalin-2,6-dicarboxylic acid, cyclohexanedicarboxylic acid, succinic acid, glutaric acid, azelaic acid and sebacic acid.
  • Suitable chain regulators are, for example, monofunctional regulators such as triacetonediamine compounds (see WO-A 95/28443), monocarboxylic acids such as acetic acid, propionic acid and benzoic acid, and also bases such as (mono) amines, for example hexylamine or benzylamine, diamines such as hexamethylenediamine or 1,4 Cyclohexyldiamine, C 4 - to C 10 -dicarboxylic acids, such as adipic acid, azelaic acid, sebacic acid, dodecanedioic acid, C 5 - to C 8 -cycloalkanedicarboxylic acids, such as cyclohexane-1, 4-dicarboxylic acid; Benzene and naphthalenedicarboxylic acids such as isophthalic acid, terephthalic acid and naphthalene-2,6-dicarboxylic acid.
  • monofunctional regulators such as tri
  • Suitable stabilizers are hindered phenols known from the literature, phosphorus compounds such as, for example, the hypophosphites and mixtures of these two classes of stabilizer.
  • the polyamides generally contain 0 to 1 wt .-%, preferably 0.05 to 0.8 wt .-%, particularly preferably 0.1 to 0.7 wt .-%, in particular 0.3 to 0.6 wt .-% stabilizers.
  • Suitable polyethylene terephthalates are generally all polyethylene terephthalates, as a rule those which are from 50 to 100 wt .-%, preferably 70 to 100 wt .-%, particularly preferably 85 to 100 wt .-% ethylene glycol and 50 to 100 wt.
  • -% preferably 70 to 100 wt .-%, particularly preferably 85 to 100 wt .-% terephthalic acid and 0 to 50 wt .-%, preferably 0 to 30 wt .-%, particularly preferably 0 to 15 wt .-% of corresponding molecular weight Mn of 10,000 to 50,000, preferably high molecular weight polyethylene terephthalates having a molecular weight of 35,000 to 50,000 or low molecular weight polyethylene terephthalates having a molecular weight of 10,000 to 25,000, more preferably low molecular weight polyethylene terephthalates having a molecular weight of 12000 to 22000.
  • polyethylene terephthalate oligomers having a molecular weight Mn of 3,000 to 12,000, preferably from 5,000 to 12,000, more preferably from 10,000 to 12,000.
  • Mn molecular weight of 3,000 to 12,000, preferably from 5,000 to 12,000, more preferably from 10,000 to 12,000.
  • the molecular weight mood is analogous to the determination in the block copolymers.
  • Suitable comonomers of ethylene glycol are triethylene glycol, 1,4-cyclohexanedimethanol, 1, 3-propanediol, butane-1, 4-diol, pentane-1, 5-diol, hexane-1, 6-diol, 3-methylpentane-1, 4-diol, 2-methylpentane-1,4-diol, 2,2,4-trimethylpentane-1,3-diol, 2-ethylhexane-1,3-diol, 2,2-diethylpropane-1,3-diol, 1, 3-hexanediol, 1,4-dihydroxybenzene, 2,2-bis-4- (hydroxycyclohexyl) propane, 2,4-dihydroxy-1,1,3,3-tetramethylcyclobutane, 2,2-bis (3-bis) hydroxyethoxyphenyl) propane and 2,2-bis (4-hydroxyethoxyphenyl) propane.
  • Suitable comonomers of terephthalic acid are adipic acid, isophthalic acid, phthalic acid, 2,6-naphthalenedicarboxylic acid, cyclohexanedicarboxylic acid, succinic acid, glutaric acid, sebacic acid and azelaic acid.
  • the polyethylene terephthalates can be used in minor amounts of from 0.1 to 5 wt.%, Preferably 0.1 to 3 wt.%, More preferably 0.1 to 2 wt.% Of trifunctional or tetrafunctional comonomers such as e.g. Trimellitic acid or pyromellitic acid or mixtures thereof.
  • the block copolymers of polyethylene terephthalate and the polyamide of meta-xylylenediamine and adipic acid according to the invention are suitable for the preparation or as starting material for the production of moldings, tubes, profiles, preforms, Containers, trays, fibers, films, films, bottles and foams of all kinds, for example by extrusion, injection molding, calendering, blow molding, pressing, sintering or other conventional processes of thermoplastic processing.
  • the preferred application of the block copolymers according to the invention is the preparation of blend mixtures with polyethylene terephthalate. These are particularly suitable for the production of transparent, colorless containers and molded parts, in particular of preforms and bottles for the beverage industry. In this preferred application are 0.01 and 15 wt .-%, preferably 0.02 to 10 wt .-%, particularly preferably 0.03 to 7 wt .-% block copolymer contained in the polyethylene terephthalate.
  • the granules of the block polymers are subjected to extraction. This effectively reduces the content of residual monomers.
  • the block polymers produced When mixed with polyethylene terephthalate, the block polymers produced show improved phase bonding of the polyamide to the polyethylene terephthalate matrix, which results in high transparency in the subsequent use of these blend mixtures for containers, moldings and films. At the same time, the unwanted yellowing is significantly improved.
  • Adipic acid and 0.5 wt .-% low molecular weight polyethylene terephthalate Adipic acid and 0.5 wt .-% low molecular weight polyethylene terephthalate.
  • Comparative Example A This is the polyamide MXD6007, which is commercially available from Mitsubishi Gas Chemical.
  • the preforms produced according to Example I were inflated at a temperature of 110 0 C and a pressure of 40 bar in the bottle mold of the bottle machine SB01 Sidel to 1, 5 liter bottles.
  • Turbidity measurement using a Hazeguard Dual Gauge from Gardner according to the method ASTM D100392

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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)
  • General Chemical & Material Sciences (AREA)
  • Polyamides (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

Abstract

L'invention concerne des copolymères séquencés de téréphtalate de polyéthylène et de polyamide constitué de méta-xylylène diamine et d'acide adipique, ainsi que des procédés pour leur production.
EP05825926A 2004-12-09 2005-12-03 Copolymeres sequences de terephtalate de polyethylene et de polyamide constitue de meta-xylylene diamine et d'acide adipique Withdrawn EP1828311A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004059597A DE102004059597A1 (de) 2004-12-09 2004-12-09 Blockcopolymere aus Polyethylenterephthalat und dem Polyamid aus meta-Xylylendiamin und Adipinsäure
PCT/EP2005/012983 WO2006061160A2 (fr) 2004-12-09 2005-12-03 Copolymeres sequences de terephtalate de polyethylene et de polyamide constitue de meta-xylylene diamine et d'acide adipique

Publications (1)

Publication Number Publication Date
EP1828311A2 true EP1828311A2 (fr) 2007-09-05

Family

ID=36499254

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05825926A Withdrawn EP1828311A2 (fr) 2004-12-09 2005-12-03 Copolymeres sequences de terephtalate de polyethylene et de polyamide constitue de meta-xylylene diamine et d'acide adipique

Country Status (12)

Country Link
US (1) US20100240839A1 (fr)
EP (1) EP1828311A2 (fr)
JP (1) JP2008523180A (fr)
KR (1) KR20070098848A (fr)
CN (1) CN101072834A (fr)
AU (1) AU2005313606A1 (fr)
BR (1) BRPI0518515A2 (fr)
CA (1) CA2587631A1 (fr)
DE (1) DE102004059597A1 (fr)
NZ (1) NZ555393A (fr)
RU (1) RU2007125569A (fr)
WO (1) WO2006061160A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005051400A1 (de) * 2005-10-25 2007-04-26 Basf Ag Polyamide aus meta-Xylylendiamin und Adipinsäure mit einem Aminoendgruppengehalt kleiner als 15 mmol/kg
KR20150052862A (ko) * 2012-09-03 2015-05-14 바스프 에스이 중축합에 의해 폴리아미드를 제조하는 방법
JP6201502B2 (ja) * 2013-08-09 2017-09-27 東洋製罐株式会社 透明性に優れた樹脂組成物及びその製造方法
CN114316532A (zh) * 2022-01-04 2022-04-12 海信（山东）冰箱有限公司 Pet注塑级厚材、其制备方法及冰箱

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3493632A (en) * 1966-05-18 1970-02-03 Toray Industries Process for the preparation of block copolymers of polyamide and polyester and of fibers therefrom
GB1230195A (fr) * 1968-05-30 1971-04-28
US4788249A (en) * 1987-11-04 1988-11-29 General Electric Company Thermoplastic resins and polyamides compatibilized with polyamide-polyester block copolymers
US5258233A (en) * 1992-04-02 1993-11-02 Eastman Kodak Company Polyester/polyamide blend having improved flavor retaining property and clarity
BR0012815A (pt) * 1999-07-30 2002-05-07 Eastman Chem Co Mistura de polìmero, artigo, e, método para reduzir a permeabilidade a gás de poliéster

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006061160A2 *

Also Published As

Publication number Publication date
DE102004059597A1 (de) 2006-06-22
WO2006061160A2 (fr) 2006-06-15
US20100240839A1 (en) 2010-09-23
RU2007125569A (ru) 2009-01-20
BRPI0518515A2 (pt) 2008-11-25
CN101072834A (zh) 2007-11-14
WO2006061160A3 (fr) 2006-08-24
JP2008523180A (ja) 2008-07-03
KR20070098848A (ko) 2007-10-05
CA2587631A1 (fr) 2006-06-15
NZ555393A (en) 2009-08-28
AU2005313606A1 (en) 2006-06-15

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