CA1173998A - Aromatic polyester carbonates, a process for their preparation and their use for the production of injection moulded articles, films and coatings - Google Patents

Aromatic polyester carbonates, a process for their preparation and their use for the production of injection moulded articles, films and coatings

Info

Publication number
CA1173998A
CA1173998A CA000371956A CA371956A CA1173998A CA 1173998 A CA1173998 A CA 1173998A CA 000371956 A CA000371956 A CA 000371956A CA 371956 A CA371956 A CA 371956A CA 1173998 A CA1173998 A CA 1173998A
Authority
CA
Canada
Prior art keywords
solution
formula
polyester carbonate
compound
mol
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.)
Expired
Application number
CA000371956A
Other languages
French (fr)
Inventor
Peter Tacke
Dieter Freitag
Werner Nouvertne
Ludwig Bottenbruch
Peter R. Muller
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Application granted granted Critical
Publication of CA1173998A publication Critical patent/CA1173998A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/64Polyesters containing both carboxylic ester groups and carbonate groups

Abstract

ABSTRACT

Aromatic polyestercarbonates with an increased melt flowability are prepared based on a diphenol, terephthalic and/or isophthalic acid, phosgene and a particular chain terminator of the formula (I)

Description

:~73~38 AROMATIC ~OLYESTER CARBONATES, A PROCESS FOR THEIR PRE-PARATION AND THEIR USE FOR THE PRODUCTION OF INJECTION
MOULDED ARTICLES, FILMS AND COATINGS.
This invention relates to tileruloplastic aromatic polyester carbonates whose molecular weight has been controlled using specific chaill terminators, a method for their preparation employin r the pllase boundary surface process, and the use of these polyester carbonates for the production of injection moulded articles, films and coatings.
Aromatic polyester carbonates are 1~nown (G.S.
Kolesnikov et al., J. Polym. Science USSR, Vol. 9, 1967, P. 1705 - 1~11; U.S. Patent Nos. 3,0~0,331;
3,169,121; 3,~09,70~; German Offenlegungsschrifts Nos. 2,714,544; 2,758,030). They may be widely used where a com~ination of the e~cellent characteristics of aromatic polycarbonates (good impact strength and notch toughness, good flowability of the melt) and of pUI e aromatic polyesters (high dimensiollal stabili-ty under heat) is required.
Although the aromatic polyester carl~onates ~nown hitherto meet many requirements, e~perts are interested in further improving the characteristics of these polymers, in particular the melt flowability.
Surprisingly, it has now been foulld that this may be achieved by using specific compounds to terminate the polyester carbonate molecules.
The present invention provides thermoplastic aromatic polyester carbonates based on diphenols, terephthalic and/or isophthalic acids, phosgene, chain terminators and optionally branching agents, having an est~r group content of from 99.95 to 5 mol %, based on the total oL ester and car~onate groups, characterised in that the chain terminators are compounds of the formula:

Le A 20 203 .

73~39~3 ,, ~-X (I) in which R
~` X represents OH, OCOCl or COCl, and R represents a branched alkyl radical having 8 or 9 carbon atoms, provided that, in the alkyl radical R, the pro~ortion of methyl-hydrogen atoms, based on all the hydrogen atoms of the alkylradical, amounts to from 47 to 89~o ~ that R is i31 the o-and/or p-position, and that the upper limit of the proportion of the o-isomer is 20~o.
The invention also relates to the use of these aromatic polyester carbonates for the production of injection moulded articles, films and coatings.
The inven-tion further provides a process for the preparation of these polyester carbonates according to the two-phase boun~y surface process characterized in that the terephthalic acid ester-formlng derivative, e.g. dichloride and/or isophthalic acid ester-formlng derivative, e.g. ~ichloride (or solutions thereof), the compounds (I) (optionally in a solvent) and tlle stirred two phase mi~ture containing alkaline aqueous ~0 diphenolate solutioll, catalysts and a solvent for the aromatic polyester carbonate and phosgene are combined ~`~; together and reacted.
~ Diphenols which are preferred for the preparation ; of the polyester carbonates of the invention are compounds of the formula:

MO - Z - OE (II) in which Z represents a bifunctional, mono~ or multi-~ nuclear aromatic radical having from 6 to 30 carbon ; 30 atoms, Z being structured so that the two O~-groups are ea~h directly bonded to a carbon atom of an aromatic system.

Le A 20 203 ~;

.

:, .
:. ' ~'73~98 . - 3 ~

Dipllenols which are particularly ~)referred are compounds of the formula:

~ ~ - Y _~ ~ 0~ (III) in which Y represen-ts a single bond, an alkylene or alkylidene radical having from 1 to 7 carbon atoms, a cycloall~ylene or cycloalkylidene radical having from 5 to 12 carbon atoms, -O-, -S-~ -S-, - S ~ or -C-, O O
as well as the nuclear-alkylated and nuclear-halogenated.
. derivatives thereof, e.g.:
` hydroquinone, resorcinol, dihydroxydiphenyls, bis-(hydroxyphenyl)-alkanes, bis-(hydro~Yyphenyl)-cycloalkanes -~ bis-(hydrox~phenyl)-sulphides, ~ bis-(hydroxyphenyl)-ethers, ;.~ bis-(hydroxyphenyl)-ketones, bis-(hydroxyphenyl)-sulphoxides, bis-(hydroxyphenyl)-sulphones and ~, ~, bis (hydroxyphenyl)-diisopropylbenzeIles, and also the nuclear-alkylated and nuclear-halogenated compounds thereof. These and other suitable diphenols are described, for e~ample, in U.S. Patents Nos.
3,028,365; 3,275,601; 3,148,172; 3,062,781; 2,991,273;
3,271,367; 2,999,835; 2,970,131 and 2,999,846, in German ~ Offenlegungsschrifts Nos. 1,570~703; 2,G63,050;
2,063,052; 2,211,956; 2,211,957; in French Patent No.
Le A 20 203 . , - :

`.` ` ~7~398 1 1,5~1,51~ and in monogra~h "H. Schnell, Chemistry and Physics of Polycarbonates, Interscience Publishers, New York, 196~".
I'he ~ost important diphenols are listed by name in the follow ng:
bisphenol A=2,2-bis-(4,4-dihydroxydiphenyl)-propane, - tetramethylbisphenol A, 1,1-bis-(4-hy~ro~yphenyl)-iso-butane, 1,1-bis-(4-hydroxyphenyl)-cycloh~e, 4,4-dihydro~diphenyl, 4,4~hydroxydiphenylsulphide, 4,4'-dihydroxydiphenylsulphone and the di- and tetra- halogenated derivatives thereo~.
Bisphenol A is particularly preferred. Any mixtures of the mentioned diphenols may also be used.
The compounds of formula (I), to be used as the ` chain terminator and thereby to control the molecular ~.
. 15 weight, are known (e.g. see J. Amer. Chem. Soc. 56, 1583-1586 (1934)) or they may be prepared in a simple - malmer.
Compounds o~ formula (I) which are preferled according to the invention are for e~ample:
~, ~0 CH3 ~CH3 \=/-- CH2- CH2-CH--CH2-C~I--CH2_C~3 .~ .
and ~5 X ~ CH3 C~3 ., \~ C-CH2-C--CH3 C~3 C~3 For the preparation of the aromatic polyester carbonates of the invention,a single compound as well as mi~tures of compounds (I) may be used.
They are generally used m quantities of from G.1 to 10 mol ~0, preferably from 0.3 to 7 mol ~0 (in the case of phenols, based on diphenols, in the case of acid Le A 20 203
3~91 1 chlorides an~ cllloloc~r~ollic acid estc~s, I)ased o acid dichlol-ides).
The following may be used, for example, as branching agellts: 3- or multifunctional carbo~Yylic acid chlorides, s~ch as trimesic acid trichloride, cyanuric acid trichloride, 3,3',4,4'-benzophenone-tetracarboxylic acid te-trachloride, 1,4,5,8-naphthalene tetracarboxylic acid tetrachloride or pyromellitic acid tetrachloride, in qualltities of from . 10 0.01 to 1 0 mol ~0 (based on the dicarboxylic acid . dichlorides used) or 3- or multifunctional phenols, such as phloroglucine~
4,6-dimethyl-2,4,6-tri-(4-hydroxyphenyl)-heptene-2, 4~6-dimethyl-2~4,6-tri-(4-hydroxypheIlyl)-heptane, 15 1,3,5-tri-(4-hydroxyphenyl)-benzene, 1,1,1-tri-(4-hydroxyphenyl)-ethane, tri-(4-hydroxyphenyl)-phenylmethane, 2,~-bis[4,4-bis-(4-hydroxyphenyl)-cyclohexyl]-propaIle, ~ 2,4-bis-(4-hydroxyphenyl-isopropyl)-phenol, .` 20 tetra-(4-hydroxyphenyl)-methane, -. 2,6-bis-(2-hydro~Yy-5-methylben~yl)-4-metllyl- phenol, 2~(4-hydroxyphenyl)~2-(2,~ dihydroxyphellyl)-propane, .' tetra-(4[4-hydro~Yyphenyl-isopropyl]-pheno~y)-methane~
1,4-bis[(4,41'-dihydroxytriphenyl)-metllyl]-benzene, 25 in quantities of from 0.01 to 1.0 mol ~0 (based on the diphenols used). Phenolic branching agents may be introduced with the diphenols, and acid chloride branching agents may be introduced together with the acid dichlorides.
The aromatic polyester carbonates of the invention ~o are preferably prepared according to the two-phase bo~mdary surface process, which is described, for example, by V.V. Korshak and S.V. Vinogradova in "Polyesters", Pergamon Press, 1965, P. 448. Polycondensation may also be effected in a solvent in the presence of at least stoichiometric quantities of tertiary amines to bind Le A 20 203 3~

1 the hydrogen halide which is released. This process is described, for example, in German Offenlegungsschrift o 2,714,544.
When applying the p~lase boun~ary surface process, the diphenols are dissolved in an aqueous alkaline phase Into this solution, small quantities sucll as, ~; for e~ample, from 0.1 to l.O/o by weight (based on the diphenols used) of reducing alkaline substances, such as sodium borohydride or sodium sulphite 9 may be introduced to prevent the polyester carbonates from becoming discoloured.
As catalysts for the polycondensation reaction, from O.Ol to 5 mol ~O (based on the dipllellols used) of one or more tertiary amines and~or quaternary a~monium-and/or phosphonium compounds may be introduced into thcaqueous-alkaline phase.
Ammonium or phosphonium compounds which are `;; preferred as catalysts correspond to the formula:

~O Rl-A ~ -R3 X
-. 4 ~ R
` in which ~5 A represents a nitrogen atom or phosphorus atom, X represents chlorine or bromine, a1ld Rl, R2, R3 and R4 represent Cl-C20-alkyl, C6-C10- cycloalkyl, C7-C30-alkaryl or -aralkyl groups, and two substituents may together 3~ ` raprasent a C4-C12-alkylene group.
Tertiary amines which are preferred corraspond to the formula:
Rb R - N - R

Le A 20 203 ~1~73 1 in which R5, R6 and R7 represent C1-C20-alkyl or C~-C10-cycloall~yl groups, and two substituents may also together represent an alkylene group with frGm 4 to 12 carbon atoms.
~he following may be used as a sol~Tent *or compounds (I), the terephthalic or isophthalic acid dichlorides and the aromatic polyester carbonates:
the organic solvents known from the preparation of polycarbonates, such as dichloromethane, chloroform, . tri- ancl tetrachloroethylene, tetrachloroethanes, chlorobenzenes, di-chlorobenzenes and mi~tures of these compo~mds The polyester carbonates of the invention are u 15 preferably prepared with intensive stirring at temperatures of from 0 to 40C, in particular from 15 to 30C.
The aromatic polyester carbonates according to ~-~ the invention may be isolated according to the methods ~0 kno~l from polycarbonate synthesis according to the two-phase boundary surface process.
In this process, the organic phase containing the dissolved polyester carbonate is separated, washed and the polyester carbonate is then isolated by ~5 evaporating the solution, an evaporation e~truder preferably being used as the final stage of the working up process.
The ester and the carbonate proportions of the aromatic polyester carbonates of the invention may be in the ~orm of blocks or statistically distributed in the polymer.
When applying the phase boundary surface process, for e~ample, for the production of polyester carbonates with polyester blocks, an alkaline aqueous solution of one or more diphenols may be initially reacted with a Le A 20 203 ~ .
.

73~3~8 ~ 1 solution of one or more aromatic dical~o.Yylic acid ; dichlorides to form a pre-condensate having phenolic OH-terminal groups, and the pre-condensate may be ,.
further condensed into a polyester carbonate by
- 5 subsequently introducing phosgene. The length o~ the polyester blocks may be set by a suita~le choice of -the mole ratio of diphenol and acid chloride.
In an analogous manner, polyester carbonates with polycarbonate blocl{s are obtained wllell oligomeric carbonates having phenolic OE-terminal groups are reacted with the aromatic dicarboxylic acid dichlorides.
Polyester carbonates with a statistical distribution of the ester and carbonate groups may be obtained by simultaneously metering acid chloride and phosgene into the diphenolate solution.
~ The chain terminators which are to be used, according to the invention, i~ they are phenolic compounds, may be added to the reaction mixture before the reaction starts or during the reaction. However, sufficien-t O acid chloride and/or phosgene must be available so that they can react and restrict the chain; e.g. the chain terminator may be used together with the diphenol, may be contained in the solution of the chlorides of the aromatic dicarbo~ylic acids or may be added to the reaction mixture after a pre-condensate has been prepared.
If acid chlorides and chlorocarbonic acid esters are used as the chain terminator, they are preferably used together with the aromatic dicarboxylic acid dichlorides and/or the phosgene~
These chain terminators may also be added to the reaction mixture at the stage when the chlorides of the dicarboxylic acids and the phosgene have extensively or completely reacted.
In contrast to the aromatic polyester carbonates usùally prepared using phenol, o-phenyl-phenol, p-phenyl-Le A 20 203 .'^ ~' . .

~73~98 g ~`
phellol, dil~ethylp~lenols, cresols, halo~ell plle1lols or p-tert - butyl phenol as the molecular weight regulator, the aro~a~ic polyester carbonates according to the in~-ention e~hibit an improved colour mlmber, a substantially i~proved flowability, an increased dimensional stability under heat and on improved strength ~rith comparable mechanical characteristics.
' The aromatic polyester carbonates of the invention usually have relative solution viscosities of . 10 frcm 1.18 to 2.0, in oarticular from 1.2 to 1.5 (measured in a solution of 0.5 g polymer in 100 ml dichlororl~ethane solution at 25~.
They may contain stabilisers, such as~ for . e~aluple, antio~idants, ultraviolet stabilisers, flowing aids and mould-removal aids or other additives such as l; fillers, e.g. glass fibres, glass balls, asbestos or carbon fibres, ~ieselgur, kaolin, mineral fibres, rock flour and pigments.
The aromatic polyester carbonates o~-tained according to the preparation process of the invention are produced as a ~mitary granule after e~trusion and may be processed into moulded bodies b~ injection moulding.
They are also suitable for the production of films and coatings.
In the following Examples, the relative solution viscosity ~ rel in dichloromethane is determined at 25C
and at a concentration of 0.5 g of polymer in 100 ml of dichloromethane solution at 25~.
E~amples Description of the measuring method for determining the ~lo~ability.

Spiral-shaped strips having dimensions of 2 mm x 20 m~ are produced on an injection mouldi~g machine of the SK~I 141 type (manufacturer: "Stubbe"), at a pressure of 1050 bars and at a determined extrusion temperature, ~5 thè cross section of the strand feed beill~ lOmm2. The Le A 20 203 173~9~3 ~ - 10 -- ldia~eter of the injection moulding ~acl1ine cylinder is ~0 c~
The length of the resulting flow s~irals is a measure for the flowability of the extruded pol~ester, the length of the flow spirals being directly proportional to the ilowability of the polyester.

Description_of the metho~ for measuring the colour number Spectroscopic colour number deterulination The granule of the aromatic polyester, whose colour number is to be determined, is dissolved in dichloromethane (concentration 4 g/lO0 ml). ~he measurements are made in a layer thic~ness o~ lO cm using a spectrometer of the "Cary 2l9" type, manufactured ` by Cary, U.S.A.
In comparison with pure dichloromethane, the light transmission I at a wave length o~ 20 nm and the light transmission Io at a wave length of 700 nm is measured. ~he colour number of the granule, measured at 402 n~, is calculated according to the equation:

FZ(420 nm) = ll.5 g log Io Determination of notch tou~hness and impact stren~th The notch touchness a~ according to Charpy and the impact strength an according to Charpy were tested accordin~ to DI~ 53 45~.
;,o Comparative E~ample 1 2.736 kg of bisphenol A (BPA), l.5 l of 45~0 by weight aqueous sodium hydroxide, 8.4 g of sodium borohydride, 120 g of triethyl benzyl ammonium chloride, 36 l of water and 22 l of dichloromethane were introduced into a steel reactor wi-th intensive stirring under a nitrogen atmosphere, the mi~ture being stirred until the BPA
completely dissolved.
Le A 20 203 ' ' ' 1~7~9~

1 A solution of 852.72 g each o~ isophthalic acid chloride and terephthalic acid chloride and 39.5 g (3.5 mol d5) of phenol, dissolved in 3 1 o~ dichlorometllane, was introduced into the intensively stirred two phase mixture, with water cooling in 15 minutes 9 followed by stirring for 1 hour. Thereby, -the -temperature of the reaction mixture did not exceed 22C. Tlle plL vallle of the mixture was maintained at 12-13 by addillg sodium hydroxide.
600 g of phosgene were introduced while stirring was continued, the temperature again being main-tained at approximately 20C and the pH value at 12-13. When the phosgene had been introduced, 12 ml of a 4~0 by weight aqueous solution of triethyl amine was added, followed by stirring for 1 hour.
After the aqueo-us-alkaline phase had been separatèd, the organic phase was initially washed with dilute phosphoric acid and then washed free of salt with water and approximately 50~0 of the dichloromethalle was distilled off under normal pressure. The remaining solution was diluted with 15 1 of chlorobenzene and the dichloromethane was continuously distilled off until the sump temperature was approximately 80C, the polyester carbonate was then released from the chlorobenzene in the vacuum extruder at 320C, was drawn off as a strand and granulated. The ~ranulate had a relative solution viscosity ~ rel of 1.262.
Comparative E~ample 2 Analogous to comparative Example 1, a polyester 3o carbonate was prepared using 63 g (3.5 mol O) of ~-tert -butyl phenol (instead of phenol) as the chain terminator. The relative solution viscosity ~ rel o~
the product was 1.258.
Examples 1 and 2 (according to the invention) Analogous to comparative Exa~ple 1, polyester ` Le A 20 203 --7~998 1 car~onates were prepared using 86.7 g 0:~ p-isooctyl phenol or 92.5 g (87~o of ~-proportion, 13~o of o-proportion) of isononyl phenol (respectively 3.5 mol ~ of chain terminator!. The relative solution viscosity ~ rel was 1.265 and 1.259.
Comparative Example 3 As ~as described ~or co~lparative ~ample 1, 2.736 ky of BPA, 1.5 1 of 45 ~ by weight of aqueous sodium h~droxide~
8.4 ~ of sodium borohydride, 180 g o~ triethyl benzyl ammonium chloride, 39.5 g of phenol, 36 1 of water and ~2 1 o~ dichloromethane were stirred in the steel reactor until the BPA dissolved.
A solution of 365.46 g each of iso- and terephthalic acid chloride, dissolved in 3 1 dichloromethane, and 1450 g of phosgene were then simultaneously introduced or directed into the intensively stirred two-phase mi~Yture during 15 minutes, the temperature of the mixture not eYceeding 22C and the p~ value remaining at 12-1 (cooling, addition of sodium hydroxide).
120 ml of a 4% by weight aqueous solution of triethyl amine were added subsequent to the metering of acid chloride, whereupon the mixture was then stirred intensively for another hour.
The mixture was worked up as described in comparative ample 1. The granulate which was obtailled had a relative solution viscosity ~ rel of 1.251.
ample 3 (according to the invention) Analogous to comparative Example ~, a polyester car~onate was prapared using 86.7 g of p-isooctyl phenol (3.5 mol $) instead of phenol, The isooctyl phenol was contained in the solution of the acid chlorides. The granulate of the cocondensate had a relative solution viscosity ~ rel of 1.255.
Comparative Exanlple 4 ~5 Analogous to comparative Example 1, 2.736 kg of Le A 20 203 .i .

~7~9~3 1 BPA, 1.5 1 of 45 % by weight aqueous sodium hydroxide, 130 g of triethyl benzyl ammonium chloride, 8.4 g of sodium borohydride, 36 1 of water and 22 1 of dichloromethaIle were stirred until the BPA completely dissolved. .~ sclution of - 5 1096.38 g eacll of iso- and terephthalic acid chloride and 67.86 g of p-tert.-butyl phenol (3.77 mol ~0) in 3 1 of dichloromethane was then introduced into the mi~ture with intensive stirring in 15 minutes. After subsequently s-tirring for 1 hour, 215 ~ of phosgene were introduced in 10 minutes. During this process, the pH value was maintained at 12-13 as for the first step of the reaction using sodium hydroxide and the temperature was maintained belo~ 22C by cooling. The subsequent reaction lasted 1 hour. Also, a tertiary amine was not used as a catalyst. The granulate which was obtained after working up the miæture in conventional manner had a relative solution viscosity ~ rel of 1.248.
E~ample 4 (accordin~ to the inventioll) The reaction described in comparative Example 4 was repeated, but 43.3 g (3.77 mol %) of ~-isooctyl phenol were used instead of p-tert.-butyl phenol. The product had a relative solution viscosity ~ rel of 1.246.
Comparative E~an~ple 5 As in comparative Example 1, 2.736 kg of BPA, 1.5 1 of 45 % by weight aqueous sodium h~droxide, 44.5 g of triphenyl ethyl phosphonium bromide, 8.4 g of sodiu~ borohydride, 36 1 of water and 22 1 of dichloromethalle were stirred until the BPA completely dissolved, a solution of each 609.1 g of iso- and terephthalic acid chloride and 39.5 g (3.5 mol ~0) of phenol dissolved in 3 1 of diohloromethane were then added simultaneously, and 900 g of phosgene were introduced during 20 minutes. The subsequent condensation took place during 1 hour after the addition of 120 ml of a 4p by weight triethyl amine solution. After ~5 the conventional working up (comparative Example 1), the Le A 20 203 1~739~8 1 granulate which was obtained had a relative solution viscosity ~ rel o:E 1.258.
E~ample 5 (according -to the invention) Analogous to comparative Example 5, a cocondensate was prepared ~lsing 92.5 g (3.05 mol ~0) of isononyl phenol (87do of p-isomer, 13% of o isomer) instead of phenol.
The relative solution viscosity ~ rel of the product was 1. 256.
Com~arative EYample 6 ~nalogous to comparative Example 1, 2.736 kg of BPA, 1.5 1 of 45 ~ by weight a~ueous sodium hydroxide, 100 ~ of triethyl benzyl a~nium chloride, 8.4 g of sodium borohydride, 2~ 1 of water and 22 1 of dichloromethane were stirred until the BPA completely dissolved. A solution of 73 g f tere- and 171 g of isophthalic acid chloride and 63 g (3.5 mol ~0) of p--tert.-butyl phenol dissolved in 3 1 of dichloromethane, was simultaneously added during 20 minutes with intensive stirring, and 1600 g of phosgene were introduced. After adding 120 ml of 4~0 by weight of triethylamine solution, the reaction mixture was then reacted for 1 hour. The granulated cocondensate had a relative solution viscosity ~ rel of 1.265.
Example 6 (accordin~ to the invention) . In order to prepare a polyester carbonate according 25 to the invention, the process was carried out analogo~s '~ to comparative Example 6, but the p-tert.-butyl phenol ;~ was replaced by 86.7 g of p-isooctyl phenol. The relative solution viscosity ~ rel of the product was 1,268.

Le A 20 203 ~73~98 ` ~n h o ~ o c~l ~ c~l ~1 ~1 a~ ~ c~ co o ~ C\l ~ ~ C~l ~ C`l C\l C\l ~ ~1 C\l ~ ~1 o , _ ~ h i~ h o ~ a~ ~ ~ rl a) u~ 1 ,,, h ~1 a 0~ ~ ~ ~ ~ O co ,, c~
t~ ~ ~ ~ C\l ~ ~, C . - .
Iq .,, J~

h o ~ ~ o S~
.,~ ,1 ~ ~ C: V V C~ ~ V V ~) V C~ V C:) ~ U~ oooooooooooo S ,, ~2 a) bO r~ ~1 o C~l ,~) ~ a) ~ ~ ~ ~ ~ co oo u~ L~ ~ ct) ~ ~ u~, u~ O
~0 ~ ~ 1 ': O ~0 ~
U~
.~ .
,, ~ , _ ,_ rd _ ~.
h v~c~ cq ~a ' ~o ~ ~ r~ ,~ ~ u~ c~\ ~ ~ ~ ~ co r- ~ t~
.......... . s o ~ o~ x ~ ~ ~
O+I t~ --1 ~I C\l C~l r-l C~l r-l 1-l ~I C~] t~ ~ h h ; ,~....... -- - - -----I cq ~d +' ~ ~ D O
oo ~ g O ~ l O ~ O ~ O I
a O~ ;n tR u~ u~ 'J~ ,~
h ~ rl ri ~ ~ ~ v .-/ ~ ,~ a~ ~ ~
~1 h h ~ h r~ ~J h H
~1 ~ ~ ~
-t ~ ~ ~ a ~3 ~4 3 ~ a ~ ~g a ~ ~ ~ a ~ a ~
O O ~ ~1 0 ~ O ~ O
. V V 1~ ~ V ~ V I d v ~1 V ~.;3 H
. . ._. - . . _., Le A 20 203

Claims (12)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A thermoplastic aromatic polyester carbonate based on a diphenol, terephthalic and/or isophthalic acid, phosgene and a chain terminator having an ester group content of from 99.95 to 5 mol %, based on the total of ester and carbonate groups, in which the chain terminator is a compound of the formula:

(I) in which X reprepresents OH, OCOCl or COCl, and R represents a branched alkyl radical having 8 or 9 carbon atoms, provided that, in the alkyl radical R, the proportion of methyl-hydrogen atoms, based on all hydrogen atoms of alkyl radical, is from 47 to 89%, that R is in the o- and/or o-position, and that the upper limit of the proportion of o-isomer is 20%.
2. A polyester carbonate according to claim 1, which has a relative solution viscosity of from 1.18 to 2.0 measured in a solution of 0.5 g polymer in 100 ml dichloromethane solution at 25°C.
3. A polyester carbonate according to claim 1 which has a relative solution viscosity of from 1.2 to 1.5 measured in a solution of 0.5 g polymer in 100 ml dichloromethane solution at 25°C.
4. Polyester carbonates according to claim 1, which is branched.
5. A polyester carbonate according to claims 1 or 2, wherein the chain terminator is selected from the compounds:

and wherein X is as defined in claim 1.
6. A polyester carbonate according to claim 1 or 2, wherein the diphenol has the formula:

(III) in which Y represents a single bond, an alkylene or alkylidene radical having from 1 to 7 carbon atoms, a cycloalkylene or cycloalkyl-idene radical having from 5 to 12 carbon atoms, -O-, -S-, -?-, -SO2- or -C-, as well as the nuclear-alkylated and nuclear-halogenated derivatives thereof.
7. A process for the preparation of the polyester carbonate as defined in claim 1, which process comprises combining to-gether terephthalic acid dichloride and/or isophthalic acid dichloride or a solution thereof, the compound of the formula (I) or a solution thereof and a stirred two-phase mixture containing alkaline aqueous diphcnolate solution, a catalyst and a solvent for the aromatic polyester carbonate and phosgene and reacting them according to the two-phase boundary surface process.
8. A process according to claim 7, wherein the compound of the formula (I) and the terephthalic and/or isophthalic acid dichloride are introduced together into the reaction mixture.
9. A process according to claim 7, wherein the compound of the formula (I) is used in quantities of from 0.1 to 10 mol % by weight based on the diphenol or the acid dichloride.
10. A process according to claim 7 or 8, wherein the compound of the formula (I) is used in quantities of from 0.3 to 7 mol %
by weight based on the diphenol or the acid dichloride.
11. A process according to claim 7, 8 or 9, wherein the reaction is carried out at a temperature of from 0 to 40°C.
12. A method for the production of molded articles, films or coatings, which method comprises injection molding using the polyester carbonate as defined in claim 1, 2 or 3.
CA000371956A 1980-03-01 1981-02-27 Aromatic polyester carbonates, a process for their preparation and their use for the production of injection moulded articles, films and coatings Expired CA1173998A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3007934.6 1980-03-01
DE19803007934 DE3007934A1 (en) 1980-03-01 1980-03-01 AROMATIC POLYESTER CARBONATES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR THE PRODUCTION OF INJECTION MOLDING ARTICLES, FILMS AND COATS

Publications (1)

Publication Number Publication Date
CA1173998A true CA1173998A (en) 1984-09-04

Family

ID=6096029

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000371956A Expired CA1173998A (en) 1980-03-01 1981-02-27 Aromatic polyester carbonates, a process for their preparation and their use for the production of injection moulded articles, films and coatings

Country Status (4)

Country Link
EP (1) EP0036080B1 (en)
JP (1) JPS56133331A (en)
CA (1) CA1173998A (en)
DE (2) DE3007934A1 (en)

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585596A (en) * 1983-09-20 1986-04-29 Bayer Aktiengesellschaft Process for the production of aromatic polyester carbonates in the absence of tertiary amines
US4645806A (en) * 1984-12-13 1987-02-24 Bayer Aktiengesellschaft Use of certain polyphenylene oxides for the production of aromatic block polyether-poly(ester) carbonates by the interfacial process
US4746711A (en) * 1985-10-23 1988-05-24 Bayer Aktiengesellschaft Mixtures of aromatic polycarbonates and aromatic polyester-carbonates, and their use for the production of mouldings, films, fibres, filaments and coatings
US4794141A (en) * 1985-02-26 1988-12-27 Bayer Aktiengesellschaft Thermoplastic moulding compositions based on polysiloxane/polycarbonate block copolymers
US4864011A (en) * 1986-09-18 1989-09-05 General Electric Company Method of preparing an aromatic polycarbonate with phenolic chloroformate chain stopper
US4946927A (en) * 1988-04-12 1990-08-07 Bayer Aktiengesellschaft Preparation of aromatic polycarbonates, aromatic polyester carbonates and aromatic polyesters with organic phase comprising mixture of hydrocarbons
US4973652A (en) * 1988-06-11 1990-11-27 Bayer Aktiengesellschaft Process for the production of aromatic polycarbonates, aromatic polyester carbonates and aromatic polyesters with p containing catalyst and mixture of hydrocarbons
US5025065A (en) * 1989-04-08 1991-06-18 Bayer Aktiengesellschaft Fire-retardant polycarbonates and polyesters
US5412060A (en) * 1991-08-20 1995-05-02 Bayer Aktiengesellschaft Process for the production of polycarbonate of constant viscosity
WO2009023115A2 (en) 2007-08-10 2009-02-19 Bayer Materialscience Llc Thermoplastic composition having low gloss
EP2481774A1 (en) 2007-03-02 2012-08-01 Bayer MaterialScience LLC Flame retardant thermoplastic molding composition
WO2014137680A1 (en) 2013-03-08 2014-09-12 Bayer Materialscience Llc Halogen free flame retarded polycarbonate
US8852744B2 (en) 2009-12-08 2014-10-07 Bayer Materialscience Ag Composite components with improved adhesion of polycarbonate/polyester compositions and polyurethane
EP3395800A1 (en) 2017-04-26 2018-10-31 Henkel AG & Co. KGaA Heterocyclic quaternary nitrogen compounds comprising a polymeric substituent and their use as a photolatent catalyst in curable compositions
US10308805B2 (en) 2015-12-09 2019-06-04 Covestro Llc Thermoplastic compositions having low gloss and high impact strength
WO2019206416A1 (en) 2018-04-26 2019-10-31 Henkel Ag & Co. Kgaa A quaternary nitrogen compound for use as a latent catalyst in curable compositions
US10501624B2 (en) 2015-06-18 2019-12-10 Covestro Deutschland Ag Flame-retardant polycarbonate-polyester compositions
US10655011B2 (en) 2016-04-27 2020-05-19 Covestro Deutschland Ag Antistatic and light-stable thermoplastic polycarbonate moulding compounds
US10717911B2 (en) 2015-10-09 2020-07-21 Ineos Styrolution Group Gmbh Electrically conducting thermally conductive polymer resin composition based on styrenics with balanced properties
US10731031B2 (en) 2015-12-02 2020-08-04 Ineos Styrolution Group Gmbh Method for producing ABS plastics having improved properties
US10808086B2 (en) 2013-10-08 2020-10-20 Covestro Deutschland Ag Fiber composite material, use therefor, and method for the production thereof
US10844182B2 (en) 2015-10-23 2020-11-24 Covestro Deutschland Ag Method for producing polycarbonate molding compositions with improved thermal processing stability
US10899925B2 (en) 2016-07-22 2021-01-26 Covestro Deutschland Ag Scratch-resistant polycarbonate compositions having good thermal stability
US10920037B2 (en) 2015-10-09 2021-02-16 Ineos Styrolution Group Gmbh Thermally conductive polymer resin composition based on styrenics with low density
WO2021138113A1 (en) 2020-01-02 2021-07-08 Covestro Llc Chemical resistant polycarbonate blend compositions
US11059965B2 (en) 2016-09-27 2021-07-13 Ineos Styrolution Group Gmbh Process for producing ASA plastics
US11225570B2 (en) 2017-07-05 2022-01-18 Ineos Styrolution Group Gmbh Thermoplastic resin composition with improved UV resistance
US11352494B2 (en) 2016-04-27 2022-06-07 Covestro Deutschland Ag Anti-static thermoplastic molding materials
WO2022221363A1 (en) 2021-04-13 2022-10-20 Covestro Llc Polycarbonate blend compositions having improved weatherability and scratch resistance
EP4092083A1 (en) 2021-05-18 2022-11-23 Covestro LLC Polycarbonate blend compositions having improved weatherability and scratch resistance
US11525052B2 (en) 2017-07-05 2022-12-13 Ineos Styrolution Group Gmbh Thermoplastic styrene copolymer resin composition with improved UV resistance
US11549008B2 (en) 2017-07-05 2023-01-10 Ineos Styrolution Group Gmbh Thermoplastic resin composition with improved UV resistance
US11591466B2 (en) 2019-09-05 2023-02-28 Covestro Intellectual Property Gmbh & Co. Kg Polymer composition and article made from the same
US11667780B2 (en) 2017-07-26 2023-06-06 Ineos Styrolution Group Gmbh Impact modified styrene copolymer composition comprising polysiloxane additive having improved abrasion characteristics
US11680127B2 (en) 2018-08-29 2023-06-20 Ineos Styrolution Group Gmbh Process for the production of graft copolymer powder compositions and thermoplastic resin compositions
US11680161B2 (en) 2017-11-13 2023-06-20 Ineos Styrolution Group Gmbh Thermoplastic molding composition and articles made thereof having improved surface quality
US11718749B2 (en) 2017-09-28 2023-08-08 Covestro Deutschland Ag Polycarbonate composition
US11732130B2 (en) 2019-12-04 2023-08-22 Covestro Intellectual Property Gmbh & Co. Kg Flame retardant impact-modified polycarbonate composition
US11807752B2 (en) 2018-07-24 2023-11-07 Ineos Styrolution Group Gmbh Process for preparing graft rubber compositions with improved dewatering
US11965066B2 (en) 2018-06-18 2024-04-23 Ineos Styrolution Group Gmbh Thermoplastic compositions with improved UV resistance

Families Citing this family (119)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4360656A (en) * 1977-05-11 1982-11-23 The Dow Chemical Co. Alternating copolyestercarbonate resins
US4330663A (en) * 1980-12-31 1982-05-18 General Electric Company Benzoate ester terminated polyester-carbonate
DE3146055C2 (en) * 1981-11-20 1984-02-09 Mitsubishi Gas Chemical Co., Inc., Tokyo Process for the production of aromatic polyester carbonate resins
DE3344911A1 (en) * 1983-12-13 1985-06-13 Bayer Ag, 5090 Leverkusen THERMOPLASTIC POLYSILOXANE POLYESTER (CARBONATE) BLOCK COPOLYMERS, THEIR PRODUCTION AND USE
DE3346946A1 (en) * 1983-12-24 1985-07-04 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING COLORLESS AROMATIC POLYESTERS AND POLYESTER CARBONATES
DE3346945A1 (en) * 1983-12-24 1985-07-04 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING AROMATIC POLYESTER CARBONATES
DE3726189A1 (en) * 1987-08-06 1989-02-16 Eyemetrics Systems Ag Spectacle frames and parts thereof
US4931503A (en) * 1988-12-28 1990-06-05 General Electric Company Composition
EP0695785B1 (en) 1994-08-01 1998-05-20 Bayer Ag Mixtures from polycarbonate, phenolic hydroxyfunctional branched dimer fatty acid polyesters and optionally graft copolymers
DE4441846A1 (en) 1994-11-24 1996-05-30 Bayer Ag ABS molding compounds with a new morphology
US6103855A (en) * 1999-03-30 2000-08-15 General Electric Company Batch process for the production of polycarbonate by interfacial polymerization
DE10026299A1 (en) 2000-05-26 2001-11-29 Sunyx Surface Nanotechnologies Substrate with a low light-scattering, ultraphobic surface and process for its production
DE102006006167A1 (en) 2005-04-06 2006-10-12 Lanxess Deutschland Gmbh Molding compounds based on a thermoplastic polycarbonate
DE102005050072A1 (en) 2005-10-19 2007-04-26 Bayer Materialscience Ag Diffusing films and their use in flat screens
DE102007002925A1 (en) 2007-01-19 2008-07-24 Bayer Materialscience Ag Impact modified polycarbonate compositions
DE102007016786A1 (en) 2007-04-05 2008-10-09 Bayer Materialscience Ag Polycarbonate molding compositions
DE102008015124A1 (en) 2007-05-16 2008-11-20 Bayer Materialscience Ag Impact modified polycarbonate compositions
DE102007038438A1 (en) 2007-08-16 2009-02-19 Bayer Materialscience Ag Glass fiber reinforced polycarbonate molding compounds
DE102007040927A1 (en) 2007-08-30 2009-03-05 Bayer Materialscience Ag Process for the preparation of impact-modified filled polycarbonate compositions
DE102007061759A1 (en) 2007-12-20 2009-06-25 Bayer Materialscience Ag Flame-retardant toughened polycarbonate compositions
DE102007061762A1 (en) 2007-12-20 2009-06-25 Bayer Materialscience Ag Flame-retardant toughened polycarbonate compositions
DE102007061761A1 (en) 2007-12-20 2009-06-25 Bayer Materialscience Ag Flame-retardant toughened polycarbonate compositions
DE102007061758A1 (en) 2007-12-20 2009-06-25 Bayer Materialscience Ag Flame-retardant toughened polycarbonate compositions
DE102008024672A1 (en) 2008-05-21 2009-11-26 Bayer Materialscience Ag Low-temperature polycarbonate blends
EP2133202A1 (en) 2008-06-11 2009-12-16 Bayer MaterialScience AG Multi-layer optical film constructions with improved characteristics and use thereof
DE102008028571A1 (en) 2008-06-16 2009-12-17 Bayer Materialscience Ag Impact modified polycarbonate compositions
EP2157133A1 (en) 2008-08-19 2010-02-24 Bayer MaterialScience AG Films with improved characteristics
DE102008048202A1 (en) 2008-09-20 2010-04-01 Bayer Materialscience Ag Stress crack resistant and low distortion two-component moldings containing platelet or Schuppförmigen inorganic filler except talc
DE102008048201A1 (en) 2008-09-20 2010-04-01 Bayer Materialscience Ag Stress crack resistant and low warpage two-component moldings containing isotropic filler
DE102008048204A1 (en) 2008-09-20 2010-04-01 Bayer Materialscience Ag Stress crack resistant and low distortion two-component moldings containing talc
DE102008060536A1 (en) 2008-12-04 2010-06-10 Bayer Materialscience Ag Impact-modified polycarbonate compositions containing acid phosphorus compounds with basic precipitated emulsion graft polymer
DE102008062903A1 (en) 2008-12-23 2010-06-24 Bayer Materialscience Ag Flame-retardant toughened polycarbonate compositions
DE102009005762A1 (en) 2008-12-23 2010-06-24 Bayer Materialscience Ag Impact modified polycarbonate compositions
DE102008062945A1 (en) 2008-12-23 2010-06-24 Bayer Materialscience Ag Flame-retardant toughened polycarbonate compositions
EP2210916A1 (en) 2009-01-23 2010-07-28 Bayer MaterialScience AG Polycarbonate molding composition
DE102009009680A1 (en) 2009-02-19 2010-08-26 Bayer Materialscience Ag Compounding process for the preparation of polymer compositions with reduced content of volatile organic compounds
DE102009014878A1 (en) 2009-03-25 2010-09-30 Bayer Materialscience Ag Flame-retardant toughened polycarbonate compositions
DE102009015039A1 (en) 2009-03-26 2010-09-30 Bayer Materialscience Ag Impact-modified polycarbonate compositions for the production of metallized molded articles with a homogeneous surface gloss
DE102009025123A1 (en) 2009-06-16 2010-12-23 Osram Opto Semiconductors Gmbh Radiation-emitting device
DE102009035807A1 (en) 2009-08-01 2011-02-03 Bayer Materialscience Ag Improved adhesion between thermoplastics and polyurethane
EP2308679A1 (en) 2009-10-06 2011-04-13 Bayer MaterialScience AG Solar module with polycarbonate blend film as rear film
DE102009058182A1 (en) 2009-12-15 2011-06-30 Bayer MaterialScience AG, 51373 Composite component, useful as e.g. an interior component of track, comprises a substrate from thermoplastic containing a polymer e.g. aromatic polyesters, a rubber-modified vinyl(co)polymer and a polymer additive and polyurethane layer
US20110135934A1 (en) 2009-12-08 2011-06-09 Bayer Materialscience Ag Process For The Production Of Polyurethane Composite Components
DE102009058180A1 (en) 2009-12-15 2011-06-16 Bayer Materialscience Ag Forming composite component having thermoplastic composition support and polyurethane layer, used in e.g. tracks involves injecting composition melt into mold cavity/enlarging to form gap/injecting reactive polyurethane raw material mixture
DE102009059074A1 (en) 2009-12-18 2011-06-22 Bayer MaterialScience AG, 51373 Scratch-resistant, impact-resistant polycarbonate molding compounds with good mechanical properties II
DE102009059075A1 (en) 2009-12-18 2011-06-22 Bayer MaterialScience AG, 51373 Flame-retardant, impact-modified, scratch-resistant polycarbonate molding compounds with good mechanical properties
DE102009059076A1 (en) 2009-12-18 2011-06-22 Bayer MaterialScience AG, 51373 Scratch-resistant, impact-resistant polycarbonate molding compounds with good mechanical properties
EP2360206A1 (en) 2010-02-13 2011-08-24 Bayer MaterialScience AG Use of mixtures to produce impact-resistant modified thermoplastic compounds
DE102010018234A1 (en) 2010-04-23 2012-03-29 Bayer Materialscience Aktiengesellschaft Easy-flowing polycarbonate / ABS molding compounds with good mechanical properties and a good surface
DE102010039712A1 (en) 2010-08-24 2012-03-01 Bayer Materialscience Aktiengesellschaft Toughened polyester / polycarbonate compositions with improved elongation at break
DE102010041388A1 (en) 2010-09-24 2012-03-29 Bayer Materialscience Aktiengesellschaft Polycarbonate-based flame-retardant impact-modified battery housings II
DE102010041387A1 (en) 2010-09-24 2012-03-29 Bayer Materialscience Aktiengesellschaft Polycarbonate-based flame-retardant impact-modified battery cases I
CA2822518C (en) 2010-12-23 2018-10-02 Bayer Intellectual Property Gmbh Method for improving soot dispersion
CA2822496A1 (en) 2010-12-23 2012-06-28 Achim Feldermann Antistatic polycarbonate molding compounds
ES2493290T3 (en) 2011-06-20 2014-09-11 Styrolution (Jersey) Limited Modified impact polycarbonate compositions
EP2574642B1 (en) 2011-09-28 2013-11-20 Bayer Intellectual Property GmbH Flame-retardant PC/ABS compounds with good impact strength, flowability and chemical resistance
BR112014009287A8 (en) 2011-10-26 2017-06-20 Bayer Ip Gmbh stabilized polycarbonate compositions with mixtures of silicic acid and an inorganic acid
EP2771403B1 (en) 2011-10-26 2017-05-17 Covestro Deutschland AG Method for producing and stabilising impact resistant polycarbonate compounds using diluted solutions of acidic compounds
US20140356551A1 (en) 2011-11-30 2014-12-04 Bayer Intellectual Property Gmbh Molded bodies having high surface quality
KR20140105461A (en) 2011-12-13 2014-09-01 바이엘 인텔렉쳐 프로퍼티 게엠베하 Flame-retardant polyalkylene terephthalate/polycarbonate compositions
EP2798007B1 (en) 2011-12-29 2017-05-24 Covestro Deutschland AG Polymer compound with improved adhesion
EP2647669A1 (en) 2012-04-05 2013-10-09 Bayer MaterialScience AG Impact modified polycarbonate compounds for simplified production of low temperature components with high sheen and matt component sections
EP2657259A1 (en) 2012-04-23 2013-10-30 Bayer MaterialScience AG ABS compounds with improved surface after hot-wet storage
EP2657258A1 (en) 2012-04-23 2013-10-30 Bayer MaterialScience AG Method for producing ABS compounds with improved surface after hot-wet storage
EP2657298A1 (en) 2012-04-27 2013-10-30 Bayer MaterialScience AG PC/ABS compounds with good thermal and chemical resistance
EP2657294A1 (en) 2012-04-27 2013-10-30 Bayer MaterialScience AG PC/ABS compounds which remain stable when processed
EP2703092A1 (en) 2012-08-30 2014-03-05 Bayer MaterialScience AG Method for adjusting various shine levels of radiation cured varnishes and use of same
BR112015012955A2 (en) 2012-12-07 2017-07-11 Bayer Materialscience Ag fireproof polycarbonate molding vi
WO2014086743A1 (en) 2012-12-07 2014-06-12 Bayer Materialscience Ag Flame-retardant polycarbonate molding materials i
WO2014086944A1 (en) 2012-12-07 2014-06-12 Bayer Materialscience Ag Flame-retardant polycarbonate molding materials ii
WO2014122178A1 (en) 2013-02-07 2014-08-14 Bayer Materialscience Ag Method for the production of abs compositions having an improved surface following storage in a warm-humid environment
EP2953983A1 (en) 2013-02-07 2015-12-16 Covestro Deutschland AG Method for the production of abs compositions having an improved surface
KR20150115765A (en) 2013-02-07 2015-10-14 바이엘 머티리얼사이언스 아게 Method for the production of abs compositions having an improved surface
JP6701076B2 (en) 2013-10-02 2020-05-27 コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag Method for producing molded body by structural foam molding, foamed thermoplastic material molded part and use thereof
WO2015055719A1 (en) 2013-10-18 2015-04-23 Bayer Materialscience Ag Polycarbonate compositions having improved adhesion to polyurethane layers
EP2899008B1 (en) 2014-01-27 2016-08-31 Covestro Deutschland AG Injection moulding method for the manufacture of a composite product with a structured surface in the contact area of the layers in order to improve adhesion
US10597529B2 (en) 2015-06-09 2020-03-24 Covestro Deutschland Ag Glass-fibre-reinforced polycarbonate moulding compositions with improved toughness
WO2017055416A1 (en) 2015-10-02 2017-04-06 Covestro Deutschland Ag Polycarbonate compositions with improved stabilisation
EP3359593B1 (en) 2015-10-09 2019-12-11 INEOS Styrolution Group GmbH Electrically insulating thermally conductive polymer resin composition based on styrenics with balanced properties
WO2017065762A1 (en) 2015-10-14 2017-04-20 Covestro Llc Phosphazene modified polycarbonate molded battery cooling device
TWI745364B (en) 2016-03-23 2021-11-11 德商科思創德意志股份有限公司 Polycarbonate compositions with improved hydrolysis resistance
KR102383487B1 (en) 2016-06-06 2022-04-05 이네오스 스티롤루션 그룹 게엠베하 Methods for producing stabilizer dispersions and methods for producing thermoplastic compositions stabilized by stabilizer dispersions
ES2930761T3 (en) 2017-07-26 2022-12-21 Ineos Styrolution Group Gmbh Impact modified styrene copolymer composition comprising a polysiloxane additive having improved abrasion characteristics
WO2019121463A1 (en) 2017-12-19 2019-06-27 Covestro Deutschland Ag Thermoplastic compositions with good stability
WO2019121356A1 (en) 2017-12-21 2019-06-27 Covestro Deutschland Ag Polycarbonate composition
EP3556527A1 (en) 2018-04-19 2019-10-23 Covestro Deutschland AG Thermoplastic composite article and manufacturing method and use thereof
EP3560675A1 (en) 2018-04-24 2019-10-30 Covestro Deutschland AG Thermoplastic composite article and manufacturing method and use thereof
US20210245418A1 (en) 2018-06-07 2021-08-12 Covestro Intellectual Property Gmbh & Co. Kg Thermoplastic composite article and preparation method thereof
EP3650487A1 (en) 2018-11-06 2020-05-13 Covestro Deutschland AG Thermoplastic composite article and preparation method thereof
US20210277230A1 (en) 2018-07-25 2021-09-09 Covestro Intellectual Property Gmbh & Co. Kg Polymer blends containing thermoplastic and cross-linked reaction product from polyaddition or polycondensation
EP3608358B1 (en) 2018-08-09 2021-03-10 Covestro Intellectual Property GmbH & Co. KG Mineral-filled polycarbonate polyalkylenterephthalate composition, molding material and molded article having good impact strength
CN112602227A (en) 2018-09-07 2021-04-02 科思创有限公司 Device for cooling battery cells
EP3633785A1 (en) 2018-10-05 2020-04-08 Covestro LLC A device for cooling battery cells
CN114599736A (en) 2019-08-28 2022-06-07 科思创知识产权两合公司 Flame-retardant polycarbonate compositions and molded parts and articles made therefrom
EP4025580B1 (en) 2019-09-04 2023-10-18 Covestro Intellectual Property GmbH & Co. KG Polyphosphazene and molding composition containing same
EP3828236B1 (en) 2019-11-27 2022-06-01 Covestro Intellectual Property GmbH & Co. KG Flameproof polycarbonate polyester blend
CN115461408A (en) 2020-05-13 2022-12-09 科思创德国股份有限公司 Flame-retardant polycarbonate composition
US20230220196A1 (en) 2020-05-18 2023-07-13 Covestro Deutschland Ag Polycarbonate blend having reduced disturbing noise
US11708455B2 (en) 2020-05-22 2023-07-25 Covestro Deutschland Ag Flame-retardant polycarbonate composition
US20230167296A1 (en) 2020-05-22 2023-06-01 Covestro Deutschland Ag Flame-retardant polycarbonate composition
JP2023541667A (en) 2020-09-18 2023-10-03 コベストロ、ドイチュラント、アクチエンゲゼルシャフト Multilayer for diffuse transmitted illumination
EP4226459A1 (en) 2020-10-12 2023-08-16 Covestro LLC A modular battery pack
EP4015580A1 (en) 2020-12-18 2022-06-22 Covestro Deutschland AG Composition and method for the preparation of a translucent thermoplastic polycarbonate/polymethylmethacrylate moulding composition
EP4039746A1 (en) 2021-02-08 2022-08-10 Covestro Deutschland AG Polycarbonate / polyester composition, moulding composition and moulded article having good impact strength and high thermal load capacity
EP4047073A1 (en) 2021-02-17 2022-08-24 Covestro Deutschland AG Pyrolysis of polycarbonate-containing material for recovery of raw materials
US20240043683A1 (en) 2021-02-25 2024-02-08 Covestro Deutschland Ag Heat-resistant semi-conductive thermoplastic resin composition
WO2023280608A1 (en) 2021-07-05 2023-01-12 Covestro Deutschland Ag Composition and method for producing a transparent thermoplastic polycarbonate/polymethyl methacrylate moulding compound
WO2023009417A1 (en) 2021-07-28 2023-02-02 Covestro Llc A drug injection device and recycling system
EP4177301A1 (en) 2021-11-03 2023-05-10 Covestro Deutschland AG Polyphosphazene and moulding composition containing same
EP4201987A1 (en) 2021-12-22 2023-06-28 Covestro Deutschland AG Pyrolysis of polycarbonate-containing material in combination with phosphorus-containing organic compound for recovery of raw materials
EP4234491A1 (en) 2022-02-24 2023-08-30 Covestro Deutschland AG Method for the gasification of polymeric valuable materials for the low-emission production of carbon monoxide which can be used in the production of phosgene
EP4245521A1 (en) 2022-03-16 2023-09-20 Covestro Deutschland AG Multilayer body containing a metal layer for diffuse illumination
EP4245529A1 (en) 2022-03-16 2023-09-20 Covestro Deutschland AG Transparent multilayer body with thermal or pressure-sensitive decorative layer
EP4249560A1 (en) 2022-03-25 2023-09-27 Covestro Deutschland AG Polycarbonate / polyester composition and component with high resistance to leakage current
EP4257619A1 (en) 2022-04-04 2023-10-11 Covestro Deutschland AG Graft copolymers for reducing surface tension in polymer blends
EP4311839A1 (en) 2022-07-28 2024-01-31 Covestro Deutschland AG Mineral filled polycarbonate blend moulding material with low bpa content and method of its preparation
WO2024028309A1 (en) 2022-08-04 2024-02-08 Ineos Styrolution Group Gmbh Thermoplastic abs moulding compound with a good property combination of processability and surface quality
WO2024028311A1 (en) 2022-08-04 2024-02-08 Ineos Styrolution Group Gmbh Thermoplastic abs moulding compound having a good property combination of processability and surface quality
EP4345136A1 (en) 2022-09-29 2024-04-03 Covestro Deutschland AG Electronic component containing polycarbonate material with high track resistance

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1116721B (en) * 1976-04-02 1986-02-10 Allied Chem CARBON TEREPHTHALATE BISPHENOL COPOLYMER WORKABLE IN MELT
DE2758030A1 (en) * 1976-12-29 1978-07-13 Gen Electric Carboxylate-carbonate co:polyester - prepd. by reaction in water and water-immiscible solvent, using amine catalyst and inorganic base
DE2842005A1 (en) * 1978-09-27 1980-04-10 Bayer Ag POLYCARBONATES WITH ALKYLPHENYL END GROUPS, THEIR PRODUCTION AND THEIR USE

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585596A (en) * 1983-09-20 1986-04-29 Bayer Aktiengesellschaft Process for the production of aromatic polyester carbonates in the absence of tertiary amines
US4645806A (en) * 1984-12-13 1987-02-24 Bayer Aktiengesellschaft Use of certain polyphenylene oxides for the production of aromatic block polyether-poly(ester) carbonates by the interfacial process
US4794141A (en) * 1985-02-26 1988-12-27 Bayer Aktiengesellschaft Thermoplastic moulding compositions based on polysiloxane/polycarbonate block copolymers
US4746711A (en) * 1985-10-23 1988-05-24 Bayer Aktiengesellschaft Mixtures of aromatic polycarbonates and aromatic polyester-carbonates, and their use for the production of mouldings, films, fibres, filaments and coatings
US4864011A (en) * 1986-09-18 1989-09-05 General Electric Company Method of preparing an aromatic polycarbonate with phenolic chloroformate chain stopper
US4946927A (en) * 1988-04-12 1990-08-07 Bayer Aktiengesellschaft Preparation of aromatic polycarbonates, aromatic polyester carbonates and aromatic polyesters with organic phase comprising mixture of hydrocarbons
US4973652A (en) * 1988-06-11 1990-11-27 Bayer Aktiengesellschaft Process for the production of aromatic polycarbonates, aromatic polyester carbonates and aromatic polyesters with p containing catalyst and mixture of hydrocarbons
US5025065A (en) * 1989-04-08 1991-06-18 Bayer Aktiengesellschaft Fire-retardant polycarbonates and polyesters
US5412060A (en) * 1991-08-20 1995-05-02 Bayer Aktiengesellschaft Process for the production of polycarbonate of constant viscosity
EP2481774A1 (en) 2007-03-02 2012-08-01 Bayer MaterialScience LLC Flame retardant thermoplastic molding composition
WO2009023115A2 (en) 2007-08-10 2009-02-19 Bayer Materialscience Llc Thermoplastic composition having low gloss
US8852744B2 (en) 2009-12-08 2014-10-07 Bayer Materialscience Ag Composite components with improved adhesion of polycarbonate/polyester compositions and polyurethane
WO2014137680A1 (en) 2013-03-08 2014-09-12 Bayer Materialscience Llc Halogen free flame retarded polycarbonate
US10808086B2 (en) 2013-10-08 2020-10-20 Covestro Deutschland Ag Fiber composite material, use therefor, and method for the production thereof
US10501624B2 (en) 2015-06-18 2019-12-10 Covestro Deutschland Ag Flame-retardant polycarbonate-polyester compositions
US10717911B2 (en) 2015-10-09 2020-07-21 Ineos Styrolution Group Gmbh Electrically conducting thermally conductive polymer resin composition based on styrenics with balanced properties
US10920037B2 (en) 2015-10-09 2021-02-16 Ineos Styrolution Group Gmbh Thermally conductive polymer resin composition based on styrenics with low density
US10844182B2 (en) 2015-10-23 2020-11-24 Covestro Deutschland Ag Method for producing polycarbonate molding compositions with improved thermal processing stability
US10731031B2 (en) 2015-12-02 2020-08-04 Ineos Styrolution Group Gmbh Method for producing ABS plastics having improved properties
US10308805B2 (en) 2015-12-09 2019-06-04 Covestro Llc Thermoplastic compositions having low gloss and high impact strength
US11352494B2 (en) 2016-04-27 2022-06-07 Covestro Deutschland Ag Anti-static thermoplastic molding materials
US10655011B2 (en) 2016-04-27 2020-05-19 Covestro Deutschland Ag Antistatic and light-stable thermoplastic polycarbonate moulding compounds
US10899925B2 (en) 2016-07-22 2021-01-26 Covestro Deutschland Ag Scratch-resistant polycarbonate compositions having good thermal stability
US11059965B2 (en) 2016-09-27 2021-07-13 Ineos Styrolution Group Gmbh Process for producing ASA plastics
EP3395800A1 (en) 2017-04-26 2018-10-31 Henkel AG & Co. KGaA Heterocyclic quaternary nitrogen compounds comprising a polymeric substituent and their use as a photolatent catalyst in curable compositions
US11225570B2 (en) 2017-07-05 2022-01-18 Ineos Styrolution Group Gmbh Thermoplastic resin composition with improved UV resistance
US11525052B2 (en) 2017-07-05 2022-12-13 Ineos Styrolution Group Gmbh Thermoplastic styrene copolymer resin composition with improved UV resistance
US11549008B2 (en) 2017-07-05 2023-01-10 Ineos Styrolution Group Gmbh Thermoplastic resin composition with improved UV resistance
US11667780B2 (en) 2017-07-26 2023-06-06 Ineos Styrolution Group Gmbh Impact modified styrene copolymer composition comprising polysiloxane additive having improved abrasion characteristics
US11718749B2 (en) 2017-09-28 2023-08-08 Covestro Deutschland Ag Polycarbonate composition
US11680161B2 (en) 2017-11-13 2023-06-20 Ineos Styrolution Group Gmbh Thermoplastic molding composition and articles made thereof having improved surface quality
WO2019206416A1 (en) 2018-04-26 2019-10-31 Henkel Ag & Co. Kgaa A quaternary nitrogen compound for use as a latent catalyst in curable compositions
US11965066B2 (en) 2018-06-18 2024-04-23 Ineos Styrolution Group Gmbh Thermoplastic compositions with improved UV resistance
US11807752B2 (en) 2018-07-24 2023-11-07 Ineos Styrolution Group Gmbh Process for preparing graft rubber compositions with improved dewatering
US11680127B2 (en) 2018-08-29 2023-06-20 Ineos Styrolution Group Gmbh Process for the production of graft copolymer powder compositions and thermoplastic resin compositions
US11591466B2 (en) 2019-09-05 2023-02-28 Covestro Intellectual Property Gmbh & Co. Kg Polymer composition and article made from the same
US11732130B2 (en) 2019-12-04 2023-08-22 Covestro Intellectual Property Gmbh & Co. Kg Flame retardant impact-modified polycarbonate composition
WO2021138113A1 (en) 2020-01-02 2021-07-08 Covestro Llc Chemical resistant polycarbonate blend compositions
WO2022221363A1 (en) 2021-04-13 2022-10-20 Covestro Llc Polycarbonate blend compositions having improved weatherability and scratch resistance
EP4092083A1 (en) 2021-05-18 2022-11-23 Covestro LLC Polycarbonate blend compositions having improved weatherability and scratch resistance

Also Published As

Publication number Publication date
JPS6340211B2 (en) 1988-08-10
EP0036080B1 (en) 1984-11-28
DE3167363D1 (en) 1985-01-10
JPS56133331A (en) 1981-10-19
DE3007934A1 (en) 1981-09-17
EP0036080A1 (en) 1981-09-23

Similar Documents

Publication Publication Date Title
CA1173998A (en) Aromatic polyester carbonates, a process for their preparation and their use for the production of injection moulded articles, films and coatings
US4334053A (en) Process for the preparation of aromatic polyesters and the use thereof for the production of injection molded articles, films and coatings
US5510448A (en) Copolyestercarbonate composition derived from dihydricphenol, carbonate precursor and alpha omega-dicarboxylic acid
EP0234914B1 (en) Preparation of aromatic polyester with improved stability by addition of phosphite during preparation
US4617368A (en) Process for the production of colorless aromatic polyester and polyester carbonates
JPH03212424A (en) Process
US4600753A (en) Two stage process for the production of aromatic polyester-carbonate
US4278785A (en) Polyester composition, process therefor and molded articles therefrom
US5126495A (en) Thermoplastic polyester carbonate-polysiloxane block copolymers
US4171421A (en) Thermoplastic copolyesters
JP3071000B2 (en) Polycarbonate resin composition
EP0111849A1 (en) Branched copolyester-carbonate resins
US4400491A (en) Copolyester carbonates and the admixture thereof with known polycarbonates to give thermoplastic moulding compositions
US4517328A (en) Mixtures of substituted diphenyl ethers with aromatic polyesters and polyester carbonates having an improved processibility
EP0372299A2 (en) Polycarbonate cross-linker resin and fire resistant compositions made therefrom
CA1309544C (en) Stabilized aromatic polyester compositions
JP3039757B2 (en) Low glass transition temperature copolyester carbonate
JPH021738A (en) Molding resin
JP2783910B2 (en) Composition
US6143858A (en) Polyestercarbonate comprising residues of branched diacids
JP2698667B2 (en) Manufacturing method of aromatic polyester
JPH02219819A (en) Polycarbonate crosslinker resin and fire resistant composition prepared therefrom
JPH04282333A (en) Specific dihydroxy diphenyl bicycloalkane, formation thereof and utilization thereof for formation of high molecular polycarbonate
JP2702323B2 (en) Method for producing crystalline wholly aromatic polyester polymer
JPH0415258B2 (en)

Legal Events

Date Code Title Description
MKEX Expiry