WO1985002622A1 - Compositions de polycarbonate-polyester a couleur stabilisee, et procede de stabilisation - Google Patents

Compositions de polycarbonate-polyester a couleur stabilisee, et procede de stabilisation Download PDF

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Publication number
WO1985002622A1
WO1985002622A1 PCT/US1984/001992 US8401992W WO8502622A1 WO 1985002622 A1 WO1985002622 A1 WO 1985002622A1 US 8401992 W US8401992 W US 8401992W WO 8502622 A1 WO8502622 A1 WO 8502622A1
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WO
WIPO (PCT)
Prior art keywords
aromatic
carbonate
composition according
poly
units
Prior art date
Application number
PCT/US1984/001992
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English (en)
Inventor
Roger W. Avakian
Ronald Edward Jodice
Original Assignee
General Electric Company
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 General Electric Company filed Critical General Electric Company
Publication of WO1985002622A1 publication Critical patent/WO1985002622A1/fr

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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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • 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
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates

Definitions

  • Aromatic polycarbonate resins and polyester resins based the reaction of diols with diacids have constituted two classes of engineering thermoplastics separately useful to prepare shaped articles, as by molding, extrusion, and so forth.
  • interest has grown in combining these polymers with blends to provide certain property profiles not usually found with use of either polymer alone.
  • a shortcoming often associated with such polymer blends is the forma- tion of yellow color, however.
  • This invention thus comprises two facets: blend compositions which have been color stabilized with the aforementioned phosphorus compounds, and a method for imparting color stability to a thermoplastic molding composition comprising the inclusion of such phosphorus compounds in a blend of two or more thermoplastic polymers.
  • compositions of the invention in their broadest aspects, will comprise a thermoplastic admix ⁇ ture of (a) an aromatic polycarbonate, an aromatic poly(ester-carbonate) , an aromatic dihydric phenol sulfone carbonate, or a mixture of any. of the foregoing, in combination with
  • R F(CF CF ) , n and m being independently 1 f 2 2 t or 2, and t being an integer from 3 to 8, or a mixture of the two.
  • component (a) comprises an aromatic polycarbonate, especially a poly (bisphenol A carbonate) and (b) comprises a poly(alkylene terephthalate)resin, especially poly(l,4-butylene tere- phthalate) .
  • component (a) comprises a poly(ester-carbonate) and component (b) comprises a copolyester based on isophthalic and tere- phthalic acid with an aliphatic diol.
  • component (a) is an aromatic di- hydric phenol sulfone resin, especially a copolymer of a sulfone and bisphenol A prepared with phosgene. All of these are made more resistant to color formation by the inclusion of a small amount of " a phosphorus compound as described above, and preferably phosphorous acid.
  • this can comprise an aromatic polycarbonate resin, whicch can be made by those skilled in the art or can be obtained from a variety of commercial sources. They may be prepared by reacting a dihydric phenol with a carbonate precursor, such as phosgene, a haloformate or a carbonate ester. Typically, they will have recurring structural units of the formula:
  • A is a divalent aromatic radical of the dihydric phenol employed in the polymer producing reaction.
  • the aromatic carbonate polymers have an intrinsic viscosity ranging from 0.30 to 1.0 dl./g. (measured in methylene chloride at 25°C.)
  • dihydric phenols is meant mononuclear or polynuclear aromatic compounds con ⁇ taining two hydroxy radicals, each of which is attached to a carbon atom of an aromatic nucleus.
  • Typical dihydric phenols include 2,2-bis-(4-hydroxy-phenyl)propane; 2-2- bis-(3,5-dimethyl-4-hydroxyphenyl)propane, 4,4"-dihydroxy- diphenyl ether, bis(2-hydroxyphenyl)methane, mixtures thereof and the like.
  • the preferred aromatic carbonate polymer for component (a) is a homopolymer derived from 2,2-bis(4-hydroxy-phenyl)propane(bisphenol-A) .
  • esters-carbonates for use in the invention are known and can be obtained commercially. Generally, they are copolyesters comprising recurring carbonate groups:
  • aromatic carbocyclic groups in the linear polymer chain in which at least some of the carboxylate groups and at least some of the carbonate groups are bonded directly to ring carbon atoms of the aromatic carbocyclic groups.
  • These poly(ester-carbonate) copolymers are prepared by reacting a difunctional ca boxylic acid, such as phthalic acid, isophthalic acid, terephthalic acid, homophthalic acid, o-, m-, and p-phenylenediacetic acid, the polynuclear aromatic acids, such as diphenic acid, 1,4-naphthalic acid, mixtures of any of the fore ⁇ going, and the like, with a dihydric phenol and a car ⁇ bonate precursor, of the types described above.
  • a difunctional ca boxylic acid such as phthalic acid, isophthalic acid, terephthalic acid, homophthalic acid, o-, m-, and p-phenylenediacetic acid
  • a par ⁇ ticularly useful polyester carbonate is derived from bisphenol-A, isophthalic acid, terephthalic acid, or a mixture of isophthalic acid and terephthalic acid, or the reactive derivatives of these acids such as tere- phthaloyl di-chloride, isophthaloyl dichloride, or a mixture thereof, and phosgene.
  • the molar . proportions of dihydroxy diaryl units to benzenedicarboxylate units to carbonate units can range from 1:0.30-0.80:0.70-0.20 and the molar range of terephthalate units to isophthalate units can range from 9:1 to 2:8 in this preferred family of resins.
  • aromatic dihydric phenol sulfone resins used in component (a) are a family of resins which can
  • OM be made by those skilled in this art.
  • homopolymers of dihydric phenol, and a dihydroxydiphenyl sulfone and a carbonate precursor can be prepared as well as copolymers of a dihydric.
  • henol and a carbonate precursor can be made according to the description in Schnell, et al., U.S. 3,271,367.
  • a preferred material is made by polymerizing bis-(3,5-dimethyl-4-hydroxy phenyl) sulfone, alone, or especially in combination with bisphenol A with phosgene or a phosgene precursor, in accordance with the description in Fox, U.S. 3,737,409.
  • a copolymer made by reacting 40 to 99 wt. percent of the sulfone and 1 to 60 wt. percent of the bisphenol with phosgene.
  • polyesters suitable for use herein are derived from an aliphatic, aliphatic ether or cycloaliphatic diol, or mixtures thereof, containing from 2 to about 10 carbon atoms and at least one aromatic dicarboxylic acid.
  • Preferred polyesters are derived from an aliphatic diol and an aromatic dicarboxylic acid and have repeated units of the following general formula:
  • n is an integer of from 2 to 4.
  • the most pre ⁇ ferred polyester is poly(ethylene terephthalate) .
  • poly- esters with minor amounts, e.g., from 0.5 to about 2 percent by weight, of units derived from aliphatic acid and/or aliphatic polyols, to form copolyesters.
  • the aliphatic polyols include glycols, such as poly(ethylene glycol). All such polyesters can be made following the teachings of, for example, U.S. Patent Nos. 2,465,319 and 3,047,539.
  • polyesters which are derived from a cyclo ⁇ aliphatic diol and an aromatic and/or cycloaliphatic dicarboxylic acid are prepared, for example, by condensing either the cis- or trans-isomer (or mixtures thereof) of, for example, 1,4-cyclohexanedimethanol with an aromatic dicarboxylic acid so as to produce a polyester having recurring units of the following formula:
  • cyclohexane ring is selected from the cis- and trans-isomers thereof and R represents an aryl or cycloaliphatic radical containing 6 to 20 carbon atoms and which is the decarboxylated residue derived from an aromatic dicarboxylic acid.
  • aromatic dicarboxylic acids repre- sented by the decarboxylated residue R are isophthalic or terephthalic acid, l,2-di(p-carboxyphenyl)ethane, 4,4'-dicarboxydiphenyl ether, etc., and mixtures of these. All of these acids contain at least one aromatic nucleus. Acids containing fused rings can also be present, such as in 1,4- or 1,5-naphthalenedicarboxylic acids. Also contemplated are cycloaliphatic diacids, such as cyclohexane dicarboxylic acid. The preferred dicarboxylic acids are terephthalic acid or a mixture of terephthalic and isophthalic " acids.
  • Another preferred polyester may be derived from the reaction of either the cis- or trans-isomer (or a mixture thereof) of 1,4-cyclohexandimethanol with a mixture of isophthalic and terephthalic acids. Such a polyester would have repeating units of the formula: .
  • Still another preferred polyester is a copoly- ester derived from a cyclohexane dimethanol, an alkylene glycol and an aromatic dicarboxylic acid.
  • copoly ⁇ esters are prepared by condensing either the cis- or trans-isomer (or mixtures thereof) of, for example, 1,4- cyclohexane-dimethanol and an alkylene glycol with an aromatic dicarboxylic acid so as to produce a copoly- ester having units of the following formulae:
  • cyclohexane ring is selected from the cis- and trans-isomers thereof, R is as previously defined, n is an integer of 2 to 4, the x units comprise from about 10 to about 90 percent by weight and the y units comprise from about 90 to about 10 percent by weight.
  • Such a preferred copolyester may be derived from the reaction of either the cis- or trans-isomer (or mixtures thereof) of 1,4-cyclohexanedimethanol and ethylene glycol with terephthalic acid in a molar ratio of 1:2:3.
  • These copolyesters have repeating units of the following formula:
  • polyesters derived from aliphatic ether diols for example, tetraethylene diol, and diacids.
  • polyesters described herein are either commercially available or can be produced by methods well known in .the art, such as those set forth in, for example, U.S. Patent No. 2,901,466.
  • the polyesters used herein have an intrinsic viscosity of from about 0.4 to about 2.0 dl/g. as measured in a 60:40 phenol/tetrachloroethane mixture or similar solvent at 23°-30°C.
  • component (a) can be present in amounts from about 1 to about 99 parts by weight, and component (b) in amounts from about 99 to about 1 parts by weight.
  • component (c) As regards component (c), as explained only very small amounts of this material need be employed, and concentrations of from 0.01 to 1.00 percent by weight, per 100 parts of the (a) and (b) combined, will achieve the desired color stabilizing effect.
  • OMP a fluorocarbon-substituted derivative of phosphorous acid, e.g., fluorocarbon substituted phosphite ester, or a mixture, as indicated. It is preferred to use the smallest amount necessary to obtain the desired result, since amounts in excess of that may be wasted and the possibility exists of some adverse effects on other properties.
  • sulfonate salt e.g., potassium benzenesulfonic acid
  • aromatic halogen compound e.g, tetrabromobisphenol A polymers or oligomers
  • syner- gist e.g., antimony oxide
  • compositions can also contain effective amounts of other suitable additives, such as dyes, pigments and other colorants, fillers, reinforcing agents, lubricants, and so forth.
  • suitable additives such as dyes, pigments and other colorants, fillers, reinforcing agents, lubricants, and so forth.
  • compositions and processing with finished, shaped articles may be accomplished using any suitable method.
  • the ingredients may be mixed together, for instance, with use of extruders, dough mixers, Banbury mixers, or other mixing devices.
  • the resulting blend may be formed or molded using compression, injection, sheeting or extrusion techniques, as desired and in accordance with particular requirements.
  • the ingredients are prepared with a preblend, the preblend is extruded in a single screw extruder at 520 to 570°F. , the extrudate is cut into pieces and injection molded at to 525°F. (barrel) and 120 to 180°F. (mold).
  • the phosphorous acid or other phosphorus containing compound or material in accordance with this invention may be added as an aqueous solution or disper ⁇ sion or in the presence of moisture without fear of adversely affecting the color stability or other properties of the composition. Moldings made from the present compositions are more color stable due to the presence of the pre ⁇ scribed additive and will be more resistant to yellowing as indicated, for instance, by a lower yellowness index number, when processed at elevated temperatures, subjected to contact with metals while being processed, or, in general, exposed to those conditions which are known to normally cause yellowing in the case of the polymers described herein.
  • thermoplastic molding composition was pre ⁇ pared, containing 50% by weight of bisphenol A poly ⁇ carbonate, having an intrinsic viscosity of about 0.4 dl./g. in chloroform at 25°C. , 50% by weight of a co- polyester (KODAR A150, Eastman Kodak, prepared from 85 mole % bf terephthalate, 15 mole % of is ⁇ phthalate and 1,4-cyclohexane dimethanol) , and 0.07% by weight of • phosphorous acid.
  • the phosphorous acid was added by shaking in a paint shaker with a blend of the two poly ⁇ mers.
  • the resultant mixture was compounded by extrusion through a 3/4 inch Killion single-screw extruder with a length/diameter ratio of 24, vented to the atmosphere, using the following conditions: Screw: Twin-flighted
  • the extrudate was cooled by running through a water bath prior to pelletizing, then dried for 4 hours at 110°C.
  • the pellets were injection molded into test pieces (dimensions: 2.5 inch x 2.5 inch x. 0.125 inch) using a 3 ounce Newbury molding machine and the following conditions:
  • Yellowness index of the molded pieces was measured in accordance with standard, STM procedure D-1925. The results are shown in the Table below. These include a comparison with a corresponding composition containing 0.07% of diphenyl isodecyl phosphite (state-of-the-art compound) as the color stabilizer.
  • the blend containing phosphorous acid has a vastly lower yellowness index.

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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)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Des compositions de polyesters ou copolyesters et de copolymères et homopolymères de polycarbonate aromatique sont stabilisées contre le jaunissement en incorporant une petite quantité comprise entre 0,01 et 1,00 % en poids d'acide phosphoreux, d'acide de phényle phosphonique, ou un dérivé fluoroalkyle d'acide phosphoreux. Les compositions ainsi que le procédé de stabilisation sont décrits.
PCT/US1984/001992 1983-12-14 1984-12-06 Compositions de polycarbonate-polyester a couleur stabilisee, et procede de stabilisation WO1985002622A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US56155983A 1983-12-14 1983-12-14
US561,559 1983-12-14

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0186250A1 (fr) * 1984-12-28 1986-07-02 General Electric Company Stabilisation de compositions ininflammables de polycarbonate-polyester
EP0376289A2 (fr) * 1988-12-28 1990-07-04 Mitsubishi Gas Chemical Company, Inc. Compositions de résine polycarbonate pour la stérilisation au moyen de radiation
EP0584801A2 (fr) * 1992-08-26 1994-03-02 Mitsubishi Chemical Corporation Résines de polycarbonate aromatique et procédé pour leur préparation
US5519106A (en) * 1992-08-26 1996-05-21 Mitsubishi Chemical Corporation Process for the preparation of aromatic polycarbonate resins
EP0933395A2 (fr) * 1998-01-28 1999-08-04 General Electric Company Composition de moulage à base de polyester
WO1999063002A1 (fr) * 1998-05-29 1999-12-09 General Electric Company Composition a mouler a base de resines de polyester et de polycarbonate presentant de bonnes caracteristiques de resistance aux chocs
WO2017055416A1 (fr) 2015-10-02 2017-04-06 Covestro Deutschland Ag Compositions de polycarbonate présentant une meilleure stabilité
EP3608358A1 (fr) 2018-08-09 2020-02-12 Covestro Deutschland AG Composition de polyalkylènetéréphtalate-polycarbonate, matière de moulage et corps moulé présentant présentant une bonne résistance aux chocs
EP4039746A1 (fr) 2021-02-08 2022-08-10 Covestro Deutschland AG Composition polycarbonate-polyester, matière de moulage et corps moulé à bonne résistance aux chocs et à résistance thermique élevée

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2701300B2 (ja) * 1988-03-25 1998-01-21 三菱瓦斯化学株式会社 光学用成形材料
JP2016216556A (ja) * 2015-05-18 2016-12-22 住化スタイロンポリカーボネート株式会社 ポリカーボネート樹脂組成物及びそれからなる成形品

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1466154A (en) * 1974-03-27 1977-03-02 Teijin Ltd Polyester compositions

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JPS5437633B2 (fr) * 1973-02-12 1979-11-16
JPS5144551B2 (fr) * 1973-03-28 1976-11-29
DE2439342A1 (de) * 1974-08-16 1976-02-26 Bayer Ag Verbesserte polycarbonat-formmassen
FR2343778A1 (fr) * 1976-03-12 1977-10-07 Unibra Sa Compositions moulables stabilisees a base de polyester et de polycarbonate et procede de preparation
JPS55110153A (en) * 1979-02-16 1980-08-25 Mitsubishi Chem Ind Ltd Resin composition
JPS5813653A (ja) * 1981-07-17 1983-01-26 Teijin Ltd 樹脂組成物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1466154A (en) * 1974-03-27 1977-03-02 Teijin Ltd Polyester compositions

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0186250A1 (fr) * 1984-12-28 1986-07-02 General Electric Company Stabilisation de compositions ininflammables de polycarbonate-polyester
WO1986004078A1 (fr) * 1984-12-28 1986-07-17 General Electric Company Stabilisation de compositions ignifuges de polycarbonate-polyester
EP0376289A2 (fr) * 1988-12-28 1990-07-04 Mitsubishi Gas Chemical Company, Inc. Compositions de résine polycarbonate pour la stérilisation au moyen de radiation
EP0376289A3 (fr) * 1988-12-28 1991-07-31 Mitsubishi Gas Chemical Company, Inc. Compositions de résine polycarbonate pour la stérilisation au moyen de radiation
US5118726A (en) * 1988-12-28 1992-06-02 Mitsubishi Gas Chemical Co., Ltd. Polycarbonate resin composition for radiation sterilization
US5519106A (en) * 1992-08-26 1996-05-21 Mitsubishi Chemical Corporation Process for the preparation of aromatic polycarbonate resins
EP0584801A3 (en) * 1992-08-26 1994-09-14 Mitsubishi Chem Ind Aromatic polycarbonate resins and process for the preparation thereof
US5455324A (en) * 1992-08-26 1995-10-03 Mitsubishi Chemical Corporation Aromatic polycarbonate resin of improved color
EP0584801A2 (fr) * 1992-08-26 1994-03-02 Mitsubishi Chemical Corporation Résines de polycarbonate aromatique et procédé pour leur préparation
EP0933395A2 (fr) * 1998-01-28 1999-08-04 General Electric Company Composition de moulage à base de polyester
EP0933395A3 (fr) * 1998-01-28 1999-11-03 General Electric Company Composition de moulage à base de polyester
WO1999063002A1 (fr) * 1998-05-29 1999-12-09 General Electric Company Composition a mouler a base de resines de polyester et de polycarbonate presentant de bonnes caracteristiques de resistance aux chocs
WO2017055416A1 (fr) 2015-10-02 2017-04-06 Covestro Deutschland Ag Compositions de polycarbonate présentant une meilleure stabilité
US10899909B2 (en) 2015-10-02 2021-01-26 Covestro Deutschland Ag Polycarbonate compositions with improved stabilisation
EP3608358A1 (fr) 2018-08-09 2020-02-12 Covestro Deutschland AG Composition de polyalkylènetéréphtalate-polycarbonate, matière de moulage et corps moulé présentant présentant une bonne résistance aux chocs
WO2020030640A1 (fr) 2018-08-09 2020-02-13 Covestro Deutschland Ag Composition de polycarbonates-téréphtalates de polyalkylène rempli de minéral, matière de moulage et corps moulé ayant une bonne résistance aux chocs
EP4039746A1 (fr) 2021-02-08 2022-08-10 Covestro Deutschland AG Composition polycarbonate-polyester, matière de moulage et corps moulé à bonne résistance aux chocs et à résistance thermique élevée
WO2022167395A1 (fr) 2021-02-08 2022-08-11 Covestro Deutschland Ag Composition de polyester de polycarbonate, composé de moulage et corps de moulage ayant une bonne résistance aux chocs et une capacité de chargement thermique élevée

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Publication number Publication date
JPS61500667A (ja) 1986-04-10
EP0167564A1 (fr) 1986-01-15

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