WO2017079206A1 - Polyester modifié - Google Patents

Polyester modifié Download PDF

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Publication number
WO2017079206A1
WO2017079206A1 PCT/US2016/060000 US2016060000W WO2017079206A1 WO 2017079206 A1 WO2017079206 A1 WO 2017079206A1 US 2016060000 W US2016060000 W US 2016060000W WO 2017079206 A1 WO2017079206 A1 WO 2017079206A1
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WO
WIPO (PCT)
Prior art keywords
component
polyester
weight percent
formula
independently chosen
Prior art date
Application number
PCT/US2016/060000
Other languages
English (en)
Inventor
Uwe Bayer
Isaac Iverson
Stephan KRETSCHNER
Josef WIEDMAN
Original Assignee
Invista North America S.Ar.L.
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 Invista North America S.Ar.L. filed Critical Invista North America S.Ar.L.
Publication of WO2017079206A1 publication Critical patent/WO2017079206A1/fr

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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
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6856—Dicarboxylic acids and dihydroxy compounds

Definitions

  • the present disclosure generally relates to a modified polyester resin.
  • Polyester resins are used in the production of a wide range of
  • polyester resins are commonly used in the production of clothing fibers, carpet fibers, and other cloth-like materials.
  • polyester resins include
  • PET polyethylene terephthalate
  • PBT polybutylene terephthalate
  • PET polytrimethylene terephthalate
  • PLA polylactic acid
  • PGA polyglycolic acid
  • PCL polycaprolactone
  • PBS polybutylene succinate
  • PEN polyethylene naphthalate
  • PET for example, is a large volume, relatively low cost polymer used in many fields, and is among the most common polyesters.
  • Polyester polymers such as PET, PBT, PTT, PLA, PGA, PBS and
  • PEN polymers have been particularly used in the production of certain durable materials that are routinely subjected to conditions of elevated wear and use. Recently, some manufacturers have substituted known polyester fibers with other types of polymers that exhibit certain properties, such as improved stain recovery and higher elastic modulus. Other polymers, such as those which contain segments typically expected to undergo hydrogen bonding between polymer chains and chain segments, have thus replaced polyester fibers in the production of some durable materials. These other types of polymers, however, are relatively costly and may not be suitable in a variety of commercial applications. Thus, it would be advantageous to produce a polymer that exhibits improved mechanical properties while maintaining the cost advantage and certain other beneficial properties that are characteristic of polyesters.
  • the disclosed modified polyester resin is directed to overcoming one or more of the problems set forth above.
  • the present disclosure is directed to a polyester
  • Ri is independently chosen from H, methyl, and ethyl
  • R2 and R3 are independently chosen from -COOH, -OH, -CI, -Br, and NH2, and
  • J and K are independently chosen from 1 , 2, 3, 4, 5, 6, 7, or 8;
  • the present disclosure is directed to a polyester comprising: 0.1 to 7 weight percent, based on the total weight of the polyester, of one monomeric component of formula (I):
  • Ri is independently chosen from H, methyl, and ethyl
  • R2 and R3 are independently chosen from -COOH, -OH, -CI, -Br, and NH2, and
  • J and K are independently chosen from 1 , 2, 3, 4, 5, 6, 7, or 8;
  • the number average molecular weight of the monomeric component of formula (I) is no more than 900.
  • the present disclosure is directed to a
  • polyester comprising:
  • Ri is independently chosen from H, methyl, and ethyl
  • R2 and R3 are independently chosen from -COOH, -OH, -CI, -Br, and NH2, and
  • J and K are independently chosen from 1 , 2, 3, 4, 5, 6, 7, or 8;
  • the present disclosure is directed to a polyester consisting essentially of:
  • Ri is independently chosen from H, methyl, and ethyl
  • R2 and R3 are independently chosen from -COOH, -COOMe, -COOEt, - COOflPr, COO/Pr, COOnBu, COOsecBu, -COOffiu, -OH, -CI, -Br, and NH 2
  • J and K are independently chosen from 1 , 2, 3, 4, 5, 6, 7, or 8;
  • the monomeric component of formula (I) has a number average molecular weight of no more than 900.
  • Additional embodiments of the present disclosure are also directed to a polyester comprising:
  • the present disclosure is directed to
  • polyester consisting essentially of:
  • the at least one dicarboxylic acid component can be chosen from terephthalic acid (TPA), dimethyl terephthalate (DMT), aromatic/aliphatic dicarboxylic acid, isophthalic acid, naphthalene 2,6-dicarboxylic acid, alkali sulfoisophthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, dodecanedioic dicarboxylic acid, any monoester of these dicarboxylic acids, any diester of these dicarboxylic acids, and mixtures thereof.
  • TPA terephthalic acid
  • DMT dimethyl terephthalate
  • aromatic/aliphatic dicarboxylic acid isophthalic acid, naphthalene 2,6-dicarboxylic acid, alkali sulfoisophthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, sub
  • the diol component can be chosen from
  • ethylene diol diethylene glycol, 1 ,2-propanediol, 1 ,3-propanediol, neopentyl glycol, 1 ,4-butanediol, 1 ,5-pentanediol, 1 ,6-hexanediol, p-xylene glycol, and mixtures thereof.
  • the monomeric component of formula (I) disclosed herein can have a molecular weight of no greater than 900.
  • the molecular weight of the monomeric component of formula (I) can range, for example, from
  • the at least one monomeric component can be present in the modified polyester resin an amount ranging from 0.1 to 7 weight percent, based on the total weight of the modified polyester resin.
  • the at least one monomeric component can be present in an amount ranging, for example, from 0.5 to 7 weight percent, from 1 to 7 weight percent, from 1.5 to 7 weight percent, from 2 to 7 weight percent, from 2.5 to 7 weight percent, from 3 to 7 weight percent, from 3.5 to 7 weight percent, from 4 to 7 weight percent, from 4.5 to 7 weight percent, from 5 to 7 weight percent, from 0.1 to 6 weight percent, from 0.5 to 6 weight percent, from 1 to 6 weight percent, from 1.5 to 6 weight percent, from 2 to 6 weight percent, from 2.5 to 6 weight percent, from 3 to 6 weight percent, from 3.5 to 6 weight percent, from 4 to 6 weight percent, from 0.1 to 5 weight percent, from 0.5 to 5 weight percent, from 1 to 5 weight percent, from 1.5 to 5 weight percent, from 2 to 5 weight percent, from 2 to 5 weight percent,
  • the dicarboxylic acid component other than the monomeric component of formulae (I) or (II) can comprise from 50 to 80 weight percent of the total weight of the modified polyester resin.
  • the dicarboxylic acid component other than the monomeric component of formulae (I) or (II) can comprise, based on the total weight of the modified polyester resin, from 55 to 80 weight percent, from 60 to 80 weight percent, from 65 to 80 weight percent, from 70 to 80 weight percent, from 50 to 75 weight percent, from 55 to 75 weight percent, from 60 to 75 weight percent, from 65 to 75 weight percent, from 50 to 70 weight percent, from 55 to 70 weight percent, from 60 to 70 weight percent, from 50 to 65 weight percent, from 55 to 65 weight percent, and from 50 to 60 weight percent.
  • the diol can comprise from 20 to 80 weight percent of the total weight of the modified polyester resin.
  • the diol component can comprise, based on the total weight of the modified polyester resin, from 25 to 80 weight percent, from 30 to 80 weight percent, from 35 to 80 weight percent, from 40 to 80 weight percent, from 45 to 80 weight percent, from 50 to 80 weight percent, from 55 to 80 weight percent, from 60 to 80 weight percent, from 65 to 80 weight percent, from 70 to 80 weight percent, from 20 to 70 weight percent, from 25 to 70 weight percent, from 30 to 70 weight percent, from 35 to 70 weight percent, from 40 to 70 weight percent, from 45 to 70 weight percent, from 50 to 70 weight percent, from 55 to 70 weight percent, from 60 to 70 weight percent, from 20 to 60 weight percent, from 25 to 60 weight percent, from 30 to 60 weight percent, from 35 to 60 weight percent, from 40 to 60 weight percent, from 45 to 60 weight percent, from 50 to 60 weight percent, from 20 to 50 weight percent, from 25 to 50 weight percent, from 30 to 50 weight weight percent,
  • the at least one dicarboxylic acid component comprises: i. from 80 to 99.9 mole percent of terephthalic acid or an ester thereof; ii. from 0 to 20 mole percent of an aromatic/aliphatic dicarboxylic acid or ester thereof having up to 20 carbon atoms; and
  • the terephthalic acid or an ester thereof can be present in the dicarboxylic acid component in a mole percent, for example, ranging from 85 to 99.9 mole percent, from 90 to 99.9 mole percent, from 95 to 99.9 mole percent, from 80 to 99.5 mole percent, 85 to 99.5 mole percent, from 90 to 99.5 mole percent, from 95 to 99.5 mole percent, from 80 to 99 mole percent, 85 to 99 mole percent, from 90 to 99 mole percent, from 95 to 99 mole percent, from 80 to 95 mole percent, 85 to 95 mole percent, from 90 to 95 mole percent, and from 80 to 85 mole percent.
  • a mole percent for example, ranging from 85 to 99.9 mole percent, from 90 to 99.9 mole percent, from 95 to 99.9 mole percent, from 80 to 99.5 mole percent, 85 to 99.5 mole percent, from 90 to 99.5 mole percent, from 95 to 99.5 mole percent, from 80 to 99 mole percent, 85 to 99 mole
  • the aromatic/aliphatic dicarboxylic acid or ester thereof, having up to 20 carbon atoms can be present in the dicarboxylic acid component in a mole percent, for example, ranging from 0.1 to 20 mole percent, from 0.5 to 20 mole percent, from 1 to 20 mole percent, from 5 to 20 mole percent, from 10 to 20 mole percent, from 15 to 20 mole percent, from 0.1 to 15 mole percent, from 0.5 to 15 mole percent, from 1 to 15 mole percent, from 5 to 15 mole percent, from 10 to 15 mole percent, from 0.1 to 10 mole percent, from 0.5 to 10 mole percent, from 1 to 10 mole percent, from 5 to 10 mole percent, from 0.1 to 5 mole percent, from 0.5 to 5 mole percent, and from 1 to 5.
  • a mole percent for example, ranging from 0.1 to 20 mole percent, from 0.5 to 20 mole percent, from 1 to 20 mole percent, from 5 to 20 mole percent, from 10 to 20 mole percent, from 15
  • (II) can be present in the dicarboxylic acid component in a mole percent, for example, ranging from 0.3 to 20 mole percent, from 0.5 to 20 mole percent, from 1 to 20 mole percent, from 5 to 20 mole percent, from 10 to 20 mole percent, from 15 to 20 mole percent, from 0.1 to 15 mole percent, from 0.5 to 15 mole percent, from 1 to 15 mole percent, from 5 to 15 mole percent, from 10 to 15 mole percent, from 0.1 to 10 mole percent, from 0.5 to 10 mole percent, from 1 to 10 mole percent, from 5 to 10 mole percent, from 0.1 to 5 mole percent, from 0.5 to 5 mole percent, and from 1 to 5.
  • a mole percent for example, ranging from 0.3 to 20 mole percent, from 0.5 to 20 mole percent, from 1 to 20 mole percent, from 5 to 20 mole percent, from 10 to 20 mole percent, from 15 to 20 mole percent, from 0.1 to 15 mole percent, from 0.5 to 15 mo
  • the at least one diol component comprises i. from 80 to 100 mole percent of ethylene glycol
  • the ethylene glycol can be present in the diol component in a mole percent, for example, ranging from 85 to 100 mole percent, from 90 to 100 mole percent, from 95 to 100 mole percent, from 80 to 99.5 mole percent, 85 to 99.5 mole percent, from 90 to 99.5 mole percent, from 95 to 99.5 mole percent, from 80 to 99 mole percent, 85 to 99 mole percent, from 90 to 99 mole percent, from 95 to 99 mole percent, from 80 to 95 mole percent, 85 to 95 mole percent, from 90 to 95 mole percent, and from 80 to 85 mole percent.
  • a mole percent for example, ranging from 85 to 100 mole percent, from 90 to 100 mole percent, from 95 to 100 mole percent, from 80 to 99.5 mole percent, 85 to 99.5 mole percent, from 90 to 99.5 mole percent, from 95 to 99.5 mole percent, from 80 to 99 mole percent, 85 to 99 mole percent, from 90 to 95 mole percent, and from 80 to 85 mole percent.
  • the at least one other glycol can be present in the diol component in a mole percent, for example, ranging from 0.1 to 20 mole percent, from 0.5 to 20 mole percent, from 1 to 20 mole percent, from 5 to 20 mole percent, from 10 to 20 mole percent, from 15 to 20 mole percent, from 0.1 to 15 mole percent, from 0.5 to 15 mole percent, from 1 to 15 mole percent, from 5 to 15 mole percent, from 10 to 15 mole percent, from 0.1 to 10 mole percent, from 0.5 to 10 mole percent, from 1 to 10 mole percent, from 5 to 10 mole percent, from 0.1 to 5 mole percent, from 0.5 to 5 mole percent, and from 1 to 5.
  • a mole percent for example, ranging from 0.1 to 20 mole percent, from 0.5 to 20 mole percent, from 1 to 20 mole percent, from 5 to 20 mole percent, from 10 to 20 mole percent, from 15 to 20 mole percent, from 0.1 to 15 mole percent, from 0.5 to 15 mo
  • the present disclosure is directed to a polyester comprising :
  • polyester composition comprising from 5 to 95 weight percent, based on the total weight of the polyester composition, of at least one modified polyester resin described herein; and from 5 to 95 weight percent, based on the total weight of the polyester composition, of at least one other polymer.
  • the at least one other polymer can include, for example, polyolefins, maleic anhydride grafted polyolefins, polyamides, ionomers and polyethers.
  • Non-limiting examples of polyolefins include polyethylene, polypropylene, polymethylpentene, and polybutene
  • non-limiting examples of ionomers include Surlyn® ionomer resins
  • non-limiting examples of polyamides include nylon-6; nylon-6,6; nylon-12; and Kevlar®.
  • the at least one modified polyester resin can be present in an amount, based on the total weight of the polyester composition, ranging from 10 to 95 weight percent, 20 to 95 weight percent, 30 to 95 weight percent, 40 to 95 weight percent, 50 to 95 weight percent, 60 to 95 weight percent, 70 to 95 weight percent, 80 to 95 weight percent, 10 to 85 weight percent, 20 to 85 weight percent, 30 to 85 weight percent, 40 to 85 weight percent, 50 to 85 weight percent, 60 to 85 weight percent, 70 to 85 weight percent, 10 to 75 weight percent, 20 to 75 weight percent, 30 to 75 weight percent, 40 to 75 weight percent, 50 to 75 weight percent, 60 to 75 weight percent, 10 to 65 weight percent, 20 to 65 weight percent, 30 to 65 weight percent, 40 to 65 weight percent, 50 to 65 weight percent, 10 to 45 weight percent, 20 to 45 weight percent, 30 to 45 weight percent, 10 to 35 weight percent, 20 to 35 weight percent, and 10 to 25 weight percent.
  • the at least one other polymer can be present in an amount, based on the total weight of the polyester composition, ranging from 10 to 95 weight percent, 20 to 95 weight percent, 30 to 95 weight percent, 40 to 95 weight percent, 50 to 95 weight percent, 60 to 95 weight percent, 70 to 95 weight percent, 80 to 95 weight percent, 10 to 85 weight percent, 20 to 85 weight percent, 30 to 85 weight percent, 40 to 85 weight percent, 50 to 85 weight percent, 60 to 85 weight percent, 70 to 85 weight percent, 10 to 75 weight percent, 20 to 75 weight percent, 30 to 75 weight percent, 40 to 75 weight percent, 50 to 75 weight percent, 60 to 75 weight percent, 10 to 65 weight percent, 20 to 65 weight percent, 30 to 65 weight percent, 40 to 65 weight percent, 50 to 65 weight percent, 10 to 45 weight percent, 20 to 45 weight percent, 30 to 45 weight percent, 10 to 35 weight percent, 20 to 35 weight percent, and 10 to 25 weight percent.
  • the polyester composition can further comprise at least one filler.
  • IV Intrinsic viscosity
  • Amorphous or pressed chips (approx.. 500 mg), were weighed on an analytical balance (Mettler AT 400 ® ) and dichloroacetic acid was added (via Dosimat ® 665 or 776, from Metrohm) in such an amount, that a final polymer concentration of 0.0100 g/mL was reached.
  • the viscosity measurement was performed with a micro-Ubbelohde viscometer from Schott (type 53820/11; 0: 0.70 mm) in a Schott AVS 500 ® apparatus. The bath temperature was held at 25.00 ⁇ 0.05°C. The micro- Ubbelohde viscometer was purged four times with pure dichloroacetic acid, then the solvent was equilibrated for two minutes. The flow time of the pure solvent was measured three times. The solvent was drawn off, and the viscometer was purged with the polymer solution four times. Before measurement, the polymer solution was equilibrated for two minutes, and then the flow time of this solution was measured three times.
  • RV relative viscosity
  • T m Melting temperature
  • a RHEO-TESTER 1000 instrument was used to measure the melt viscosity of the polyester resins.
  • the polyester resins were dried for about 16 hrs at about 160°C under reduced pressure ( ⁇ 1 mbar).
  • the dried polyester resin was compressed to 100 barg, and melted for 5 minutes at the desired measurement temperature. The measurement was made once the polyester resin was melted. Material tested at 200 sec -1 was collected, and the solution viscosity was determined. No Bagley or Rhabinowitsch-Weissenberg corrections were applied to the data thus obtained.
  • polyester resins according to the present disclosure were produced by polycondensation via two synthetic methods described below. I. Examples of Polycondensation Procedure: DMT route
  • a pilot line ester interchange reactor having heating zones of 189,
  • 210, and 228 °C was used.
  • DMT and EG were fed continuously to the reactor at feed rates of 40.4 kg/hr and 49.1 kg/hr, respectively.
  • EG was split into two flows- - one to the front end of the reactor, and the second to a later stage of the reactor.
  • Mn(OAc)2*4H20 13.0 g/hr was added as catalyst in an EG solution at the beginning of the ester interchange reactor.
  • the catalyst solution also contained acetic acid (1 .6 g/hr).
  • reaction vapors were transferred to a column that separated
  • BHET (2300 g) was melted in a 4 L flask under nitrogen. The molten monomer was stirred, and then the flask was charged with a solution of PPA (3.052 g, 5% in EG). After 10 minutes, the flask was charged with SD2O3 (97%) (0.807 g, reagent grade), and the contents were stirred an additional 10 minutes. The mixture was cooled to room temperature gradually over eight hours.
  • the torque at the agitator went up by 0.09 Nm.
  • the final heating jacket temperature achieved 284°C and the final pressure 0.8 mbar.
  • the product temperature was estimated to be about 270°C.
  • Example 2 The same general procedure was applied as described in Example 1 , except that no BCI/EG slurry was added.
  • the polycondensation reaction took place over 3 hr, 20 min, during which time the torque at the agitator increased by 0.09 Nm.
  • the final heating jacket temperature was 285°C, and the final autoclave pressure was 1 .2 mbar.
  • the product temperature was estimated to be about 270°C.
  • PE product oligomer
  • the vessel was charged with PE product (2.18 kg) and EG (0.1 kg). The reaction was performed at atmospheric pressure. The vessel was heated using thermal oil at 250 °C. Agitation was initiated when the mixture was molten. The esterification of residual carboxylate end groups was indicated by the formation of condensate water. After 30 min, BCI (20 g) and EG (100 g) were added. When the water condensate flow ceased, Sb203 (0.617 g, 97% grade) was added and the mixture was stirred for 15 min. The melt was then drained into the preheated autoclave for subsequent polyesterification.
  • the oil temperature in the heating jacket was increased from 237 °C to 287 °C, and the vessel pressure was reduced to approximately 4 mbar.
  • the IV build-up was monitored by the increase of the agitator torque.
  • the final polycondensation temperature in the heating jacket was 290 °C.
  • Example 6 Polycondensation incorporating 2.5 % BCI in PET
  • the esterifier vessel was preheated using oil at 265 °C.
  • the vessel was charged with PE product (750 g) and EG (50 g). Agitation was initiated when the mixture was molten, then a slurry of PTA (1 197 g), EG (590 g) and BCI (53.25 g) was added to the esterifier in 50-100 g portions over approximately 6 h.
  • the reaction was carried out under atmospheric pressure. This procedure required the column head temperature to be no greater than 1 10-115°, to prevent significant loss of EG from the apparatus.
  • additional EG 100 g was added to complete the esterification.
  • Sb203 (0.657 g, 97% grade) was added and the mixture was stirred for 15 min. The melt was then drained into the preheated autoclave.
  • Example 5 The same procedure as Example 5 was applied, except that 50 g BCI was added without any additional EG.
  • the polycondensation time was 35 minutes at approximately 275 °C.
  • Example 4 were each subjected to solid state polymerization (SSP) routines to increase sample IV.
  • SSP solid state polymerization
  • SSP was performed under reduced pressure (about 1 mbar) and elevated sample temperature (215°C).
  • the SSP routine was performed for 8 and 24 hours.

Abstract

Un polyester comprend 0,1 à 7 % en poids, sur la base de son poids total, d'au moins un composé monomère de formule (I), formule dans laquelle R1 est indépendamment choisi parmi H, méthyle et éthyle, R2 et R3 sont indépendamment choisis parmi-COOH,-COOMe, -COOEt, -COOIPr, -COOnPr, - CH2OH, -CI, -Br, et NH2, et J et K sont indépendamment choisis parmi 1, 2, 3, 4, 5, 6, 7 ou 8; au moins un composant d'acide dicarboxylique autre que le composant monomère de formule (I); et au moins un composant diol.
PCT/US2016/060000 2015-11-03 2016-11-02 Polyester modifié WO2017079206A1 (fr)

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US201562250298P 2015-11-03 2015-11-03
US62/250,298 2015-11-03

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235553A (en) * 1959-05-21 1966-02-15 Allied Chem N-(beta-substituted ethyl)-isocyanurates
US3985748A (en) * 1974-12-31 1976-10-12 Armstrong Cork Company Isocyanurate compounds
WO1996029357A1 (fr) * 1995-03-20 1996-09-26 Desmepol B.V. Utilisation de 1,3,5-triazines substituees en position 2-, 4- et 6- ou de tautomeres de ces triazines, pour reguler la cristallisation des polyesters lineaires et/ou des polyols de polyesters et procede de preparation correspondant
WO1997015629A1 (fr) * 1995-10-25 1997-05-01 Eastman Chemical Company Melange de polyester/polyamides ameliore en maintien de saveur et en transparence

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235553A (en) * 1959-05-21 1966-02-15 Allied Chem N-(beta-substituted ethyl)-isocyanurates
US3985748A (en) * 1974-12-31 1976-10-12 Armstrong Cork Company Isocyanurate compounds
WO1996029357A1 (fr) * 1995-03-20 1996-09-26 Desmepol B.V. Utilisation de 1,3,5-triazines substituees en position 2-, 4- et 6- ou de tautomeres de ces triazines, pour reguler la cristallisation des polyesters lineaires et/ou des polyols de polyesters et procede de preparation correspondant
WO1997015629A1 (fr) * 1995-10-25 1997-05-01 Eastman Chemical Company Melange de polyester/polyamides ameliore en maintien de saveur et en transparence

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