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WO1989003853A1 - Lubrifiants internes au polycarbonate - Google Patents

Lubrifiants internes au polycarbonate Download PDF

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Publication number
WO1989003853A1
WO1989003853A1 PCT/US1988/003433 US8803433W WO8903853A1 WO 1989003853 A1 WO1989003853 A1 WO 1989003853A1 US 8803433 W US8803433 W US 8803433W WO 8903853 A1 WO8903853 A1 WO 8903853A1
Authority
WO
WIPO (PCT)
Prior art keywords
polycarbonate
guerbet alcohol
bis
carbon atoms
hydroxyphenyl
Prior art date
Application number
PCT/US1988/003433
Other languages
English (en)
Inventor
Anthony J. O'lenick, Jr.
Original Assignee
Gaf Corporation
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 Gaf Corporation filed Critical Gaf Corporation
Publication of WO1989003853A1 publication Critical patent/WO1989003853A1/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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids

Definitions

  • This invention deals with the preparation, compositions, and application of complex esters which are useful in polycarbonate processing as internal lubricants.
  • esters of simple alcohols may be used for various purposes including polycarbonate processing.
  • U.S. Patent No. 3,784,595 issued January 8, 1974 to Schirmer et al polycarbonate molding compositions are shown which are based on the esters of a tr i hydr i c alcohol and a saturated aliphatic carboxylic acid.
  • U.S. Patent No. 4,065,436 issued to Adelmann on December 1977 describes thermoplastic molding compositions containing a mold release agent which is an ester of a saturated aliphatic carboxylic acid having from 10 to 20 carbon atoms per molecule and an aromatic hydroxy compound containing from 1 to 6 hydroxyl groups.
  • plastic lubricants There are two different types of plastic lubricants. The mode of action and consequently the applications in which each type would be used differ considerably. External lubricants are insoluble in the polymer melt and as such have a tendency to form a mono-layer on the surface of the polymer. This results in a decrease in the friction between the metal and polymer. Such lubricants are referred to as mold release agents. Internal lubricants, on the other hand, are soluble in the polymer melt and as such have a tendency to promote flow of the polymer. These materials promote flow by reduction of internal stress and promotion of inter-molecular slippage.
  • Polycarbonate compared to other thermoplastics is relatively high in viscosity and requires higher processing temperatures. Consequently, the use of internal lubricants with polycarbonate is particularly important in applications in which non-injection molding occurs.
  • the Lindner patent specifically states " The particular diacids with which the present (Lindner) invention is concerned are short chained acids containing less than 10 carbon atoms.” (Col. 1 lines 64 - 66 U.S. Patent 84, 425, 458). This limitation occurs because the desired mold release properties depend upon insolubility of the lubricant in the polycarbonate.
  • the present invention describes the esters of a guerbet alcohol, and in particular esters of a guerbet alcohol and a difunctional acid.
  • the particular esters of a guerbet alcohol which the present invention is concerned with are diacids from C 12 to C 20 and mixtures thereof which are reacted with approximately two moles of a guerbet alcohol to obtain the completely esterfied acid.
  • the guerbet alcohol portion of the present invention is particularly important in that polycarbonate resins have a high requirement for clarity as they are often used to form clear articles including safety glasses. Accordingly clarity is a particularly important aspect in obtaining a polycarbonate resin. Additionally, a substantial difficulty in the art has been to extrude polycarbonate sheets and other articles that do not rely upon mold release properties and to ensure that the polycarbonate resin is not adversely affected by the internal lubricant agent. The diesters of this invention fulfill this need.
  • the preparations of the diester may be accomplished by using as the acid component the diacid.
  • the diesters are formed by reacting essentially one mole of the diacid with two moles of alcohol. This may be done such that the alcohol is present in an excess, which is subsequently stripped off under high vacuum and high temperature.
  • the diacid reaction with the alcohol may be catalyzed with a metal, conveniently with an organo-tin or titanium catalyst.
  • the reaction thus proceeds when a small amount of heat is used to promote the reaction. Conveniently the reaction is conducted at from about 120 C to about 250 C, over a period of about 5 to 10 hours.
  • the water which is produced as a by product of the reaction is then distilled off together with any excess starting alcohol and the product is recovered in a high degree of purity.
  • a nitrogen sparge and vacuum may be applied in order to collect the water and any additional starting alcohol.
  • the condition for obtaining the product from the acid rather than the acid anhydride are substantially similar.
  • the polycarbonates with which the present diesters are effective mold release agents include homopol ycarbonates and copol ycarbonates which are based, for example, on one or more of the following bisphenols: hydroquinone, resorcinol, di hydroxydi phenyls, bis-(hydroxyphenyl)-al kanes, bis-(hydroxyphenyl)-eyeloalkanes, bis-(hydroxylphenyl)-sulphides, bis-(hydroxyphenyl)-ethers, bis-(hydroxylphenyl)-ketones, bis-(hydroxyphenyl)-sulphoxides, bis-(hydroxyphenyl)-sulphones and alpha, alpha-bis(hydroxyphenyl)-di isopropyl-benzenes, as wel l as their nuclear alkyiated and nuclear-halogenated compounds.
  • Preferred bisphenols are those of the formula I shown below:
  • R is identical or different and denotes H, C1-alkyl , Cl or Br, and in which X is a bond, C 1 C 8 -alkylene, C 2 -alkyl idene, C 5 -C 15 cycloalkylene, C 5 -C 15 -cycloalkyl idene, -SO- or formula II shown below:
  • Examples of particularly preferred bisphenols are: 2,2-bis-(4-hydroxyphenyl)-propane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)-propane, 2,2-bis-(3,5-dichloro-4-hydroxyphenyl)-propane, 2,2-bis-(3,5-dibromo-4-hydroxyphenyl)-propane, and 1,1-bis-(4-hydroxyphenyl)-cyclohexane.
  • Preferred aromatic polycarbonates are those, which are based on one or more of the bisphenols mentioned as being preferred.
  • Particularly preferred copol ycarbonates are those based on 2,2-bis-(4hydroxyphenyl)-propane and one of the other bisphenols mentioned as being particularly preferred.
  • Further particularly preferred polycarbonates are those based solely on 2,2-bis-(4-hydroxyphenyl)-propane or 2,2-bis-(3,5-dimethyl-4-hydroxyphenyl)-propane.
  • the aromatic polycarbonates can be prepared in accordance with know processes, such as, for example, in accordance with the melt trans-esterification process from bisphenols and di phenyl carbonate and the two-phase boundary process from bisphenols and phosgene, as described in the above mentioned l iterature.
  • the aromatic high-molecular weight polycarbonates can be branched due to the incorporation of small amounts, preferably of between 0.05 and 2.0 mol % (relative to diphenols employed), of trifunctional or more than trifunctional compounds, especially compounds with three of more phenol ic hydroxyl groups.
  • Some examples of compounds with three or more than three phenolic hydroxyl groups which can be used are phioroglucinol , 4,6-dimethyl-2,4,6-tri-(4hydroxyphenyl)-heptane-2, 4 , 6-d i me thyl -2 , 4 , 6- tr i - ( 4-hydroxyphenyl ) -he p tane ,
  • the aromatic high-molecular polycarbonates should as a rule have mean weight-average molecular weights M of at least 10,000; especially of 10,000 to 200,000; preferably of 20,000 to 80000; determined by measuring the relative viscosity in CH 2 Cl 2 at 25 degrees c. and a concentration of 0.5% by weight.
  • thermoplastic polycarbonate compositions using the lubricants of the present invention, find use in several high performance areas.
  • Such examples of use for the polycarbonates of the present invention utilizing the internal lubricant agents include laser read comoact recording discs, precision extrusion of polycarbonate sheets for use in greenhouses and in products safe for food contact like water and other beverage bottles, microwave wear, baby formula, bottles, beer mugs, pitchers, and food storage containers and other similar high performance specialty applications.
  • the level of use of the diesters of this invention in the polycarbonate is from about 0.25% to about 1.0%; preferably from about 0.1% to about 0.25% by weight of the total polycarbonate compositions.
  • Example land 2 A suggested utilization of the guerbet diester dodecanedi oate as obtained in Example land 2 is conducted by using 0.12% by weight of the diester, and following the general procedure given at Column 6 of U.S. Patent. No. 4,065,436.
  • the various diesters of the guerbet alcohols of the present invention give polycarbonates of high clarity and low volatility. Similar results are obtained by using the remaining esters of Example I.

Landscapes

  • 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

La présente invention concerne la préparation, des compositions, et l'application d'esters complexes qui sont utiles dans le traitement au polycarbonate à titre de lubrifiants internes.
PCT/US1988/003433 1987-10-28 1988-10-06 Lubrifiants internes au polycarbonate WO1989003853A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11454987A 1987-10-28 1987-10-28
US114,549 1987-10-28

Publications (1)

Publication Number Publication Date
WO1989003853A1 true WO1989003853A1 (fr) 1989-05-05

Family

ID=22355943

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1988/003433 WO1989003853A1 (fr) 1987-10-28 1988-10-06 Lubrifiants internes au polycarbonate

Country Status (2)

Country Link
AU (1) AU2785789A (fr)
WO (1) WO1989003853A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991003531A1 (fr) * 1989-09-01 1991-03-21 Henkel Kommanditgesellschaft Auf Aktien Nouvelle huile de base pour la production de lubrifiants
US5238985A (en) * 1987-12-30 1993-08-24 Rhone-Poulenc Surfactants And Specialties, L.P. Thermoplastic molding compositions
US6362265B1 (en) * 1998-12-04 2002-03-26 Rhodia Inc Additives with reduced residual tin content and thermoplastic compositions containing the same
FR3020371A1 (fr) * 2014-04-28 2015-10-30 Valeo Vision Composition thermoplastique

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2991273A (en) * 1956-07-07 1961-07-04 Bayer Ag Process for manufacture of vacuum moulded parts of high molecular weight thermoplastic polycarbonates
US2999835A (en) * 1959-01-02 1961-09-12 Gen Electric Resinous mixture comprising organo-polysiloxane and polymer of a carbonate of a dihydric phenol, and products containing same
US3028365A (en) * 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US3784595A (en) * 1970-12-28 1974-01-08 Bayer Ag Polycarbonate molding compositions having improved release properties containing an ester of a trihydric alcohol and a c-10 to c-22 saturated aliphatic carboxylic acid
US4007150A (en) * 1975-02-18 1977-02-08 Bayer Aktiengesellschaft Use of perfluoroalkanesulphonic acid amides and/or cyclimmonium salts of perfluoroalkansulphonic acids as mold release agents
US4065436A (en) * 1976-05-07 1977-12-27 Bayer Aktiengesellschaft Thermoplastic polycarbonate moulding compositions with improved ease of mould release
US4081495A (en) * 1976-05-07 1978-03-28 Bayer Aktiengesellschaft Thermoplastic moulding compositions and mouldings of polycarbonates, with improved ease of mould release when injection-moulded
US4097435A (en) * 1977-04-11 1978-06-27 Mobay Chemical Corporation Glass-filled polycarbonate of improved ductility
US4131575A (en) * 1975-02-22 1978-12-26 Bayer Aktiengesellschaft Thermoplastic polycarbonate molding materials with improved mold release
US4143024A (en) * 1976-05-07 1979-03-06 Bayer Aktiengesellschaft Thermoplastic polycarbonate moulding compositions with improved ease of mould release
US4425458A (en) * 1982-04-09 1984-01-10 Henkel Corporation Polyguerbet alcohol esters

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028365A (en) * 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US2991273A (en) * 1956-07-07 1961-07-04 Bayer Ag Process for manufacture of vacuum moulded parts of high molecular weight thermoplastic polycarbonates
US2999835A (en) * 1959-01-02 1961-09-12 Gen Electric Resinous mixture comprising organo-polysiloxane and polymer of a carbonate of a dihydric phenol, and products containing same
US3784595A (en) * 1970-12-28 1974-01-08 Bayer Ag Polycarbonate molding compositions having improved release properties containing an ester of a trihydric alcohol and a c-10 to c-22 saturated aliphatic carboxylic acid
US4007150A (en) * 1975-02-18 1977-02-08 Bayer Aktiengesellschaft Use of perfluoroalkanesulphonic acid amides and/or cyclimmonium salts of perfluoroalkansulphonic acids as mold release agents
US4131575A (en) * 1975-02-22 1978-12-26 Bayer Aktiengesellschaft Thermoplastic polycarbonate molding materials with improved mold release
US4065436A (en) * 1976-05-07 1977-12-27 Bayer Aktiengesellschaft Thermoplastic polycarbonate moulding compositions with improved ease of mould release
US4081495A (en) * 1976-05-07 1978-03-28 Bayer Aktiengesellschaft Thermoplastic moulding compositions and mouldings of polycarbonates, with improved ease of mould release when injection-moulded
US4143024A (en) * 1976-05-07 1979-03-06 Bayer Aktiengesellschaft Thermoplastic polycarbonate moulding compositions with improved ease of mould release
US4097435A (en) * 1977-04-11 1978-06-27 Mobay Chemical Corporation Glass-filled polycarbonate of improved ductility
US4425458A (en) * 1982-04-09 1984-01-10 Henkel Corporation Polyguerbet alcohol esters

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5238985A (en) * 1987-12-30 1993-08-24 Rhone-Poulenc Surfactants And Specialties, L.P. Thermoplastic molding compositions
WO1991003531A1 (fr) * 1989-09-01 1991-03-21 Henkel Kommanditgesellschaft Auf Aktien Nouvelle huile de base pour la production de lubrifiants
US6362265B1 (en) * 1998-12-04 2002-03-26 Rhodia Inc Additives with reduced residual tin content and thermoplastic compositions containing the same
FR3020371A1 (fr) * 2014-04-28 2015-10-30 Valeo Vision Composition thermoplastique
WO2015165744A1 (fr) * 2014-04-28 2015-11-05 Valeo Vision Composition thermoplastique
CN106459571A (zh) * 2014-04-28 2017-02-22 法雷奥照明公司 热塑性组合物

Also Published As

Publication number Publication date
AU2785789A (en) 1989-05-23

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