Polycarbonates, polyester carbonates and polyesters with...

Details Polycarbonates, polyester carbonates and polyesters with... Polycarbonates, polyester carbonates and polyesters with...

2003-04-22

2004-11-30

Boykin, Terressa (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From carboxylic acid or derivative thereof

C264S176100, C264S219000, C528S196000, C528S271000

Reexamination Certificate

active

06825312

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to thermoplastic molding compositions and more particularly to compositions that contain any of polycarbonates, polyester carbonates and polyesters that are chain terminated with a phenolic compounds having a branched structure.
SUMMARY OF THE INVENTION
A phenolic compound having a branched structure is disclosed. The compound conforms to
HO—Ar
1
—X—Ar
2
—[Y—W]
n
  (1)
wherein Ar
1
and Ar
2
independently denote an optionally substituted mononuclear or polynuclear aromatic moiety, X and Y independently denote a single bond or a divalent radical, W denotes an optionally substituted mononuclear or polynuclear aromatic moiety or an aliphatic or cycloaliphatic radical, and
n is 1 to 5, is useful as a terminal group in polycarbonates, polyester carbonates and polyesters. Also disclosed is a process for producing such resins where the disclosed compound is a chain terminator.
BACKGROUND OF THE INVENTION
Monofunctional terminal groups based on phenol, such as for example phenol, 4-alkylphenols and 4-cumylphenol, are frequently used for the production of polycarbonates (Kunststoff-Handbuch 3; L. Bottenbruch, Hanser, München 1992, p. 127; EP-A 0 353 594).
It is not known whether these conventionally used terminal groups have a positive effect on the flow behavior and/or the zero shear viscosity and/or the thermal stability and thus whether they have a positive effect on the processing properties of the corresponding polycarbonates.
The production of polycarbonates containing branched terminal groups is in principle known and is described for example in EP-A 0 794 209 and JP-A 06 256 499.
For example p-phenylphenol is known from U.S. Pat. Nos. 3,166,606 and 3,173,891 as a chain terminator for polycarbonates. From U.S. Pat. No. 4,330,663 polyester carbonates are known in which 4-butylbenzoyl chloride is used as chain terminator.
WO-A 00/50488 describes the use of di-tert.-alkylphenol as chain terminator.
From Japanese Offenlegungsschrift 57 13 31 49 polycarbonates are known that are modified with phenylpropylphenol, alkylphenols or naphthol as terminal groups.
Tritylphenol, cumylphenol, phenoxyphenol and pentadecylphenol are described in WO-A 01/05 866 as chain terminators for polycarbonates.
From EP-A 1 048 684 and WO-A 99/36 458 polycarbonates are known that have been modified for example with 4-(1,1,3,3-tetramethylbutyl)phenol and further branched alkyl phenols.
From JP-A 06 25 64 99 polycarbonates are known containing terminal groups of the structures
According to DE-A 38 03 939, chain terminators of the formula
are used, wherein R
1
, R
2
, R
3
are identical or different and denote C
2
-C
12
-alkyl or C
8
-C
20
-aralkyl, at least one of the radicals R
1
or R
2
being a C
8
-C
20
-aralkyl radical, and wherein n has a value between 0.5 and 1.
WO-A 98/22522 describes branched phenols, their use as terminal groups in polycarbonates, and polycarbonates containing such terminal groups. Furthermore, an effect of these terminal groups in the polycarbonate is said to be a lower glass transition temperature. However, no details are given either of branched phenols of the aforedescribed type or of the effect of branched terminal groups on the zero shear viscosity and thermal stability of polycarbonates.
The polyester carbonates and polyesters with known terminal groups have the disadvantage however of relatively high zero shear viscosity and/or may tend to exhibit a reduction in molecular weight and/or material discolouration under thermal stress. Thus, polycarbonates that contain secondary or tertiary hydrogen atoms, above all in the benzyl position, may be degraded under thermal stress, such as for example in an extrusion process, as a result of which the corresponding material may be discoloured. Polycarbonates that contain ester groupings as terminal groups tend under thermal stress to undergo transesterification reactions and are therefore not suitable for the melt transesterification process. (Kunststoff-Handbuch Vol. VIII, p. 150, Carl-Hanser-Verlag, Munich 1973).
DETAILED DESCRIPTION OF THE INVENTION
Against the background of the prior art the object therefore exists of providing polycarbonates, polyester carbonates and polyesters—these are referred to herein below as poly(ester)(carbonate)- and/or suitable phenolic compounds as terminal groups, that do not exhibit the disadvantage of a high zero shear viscosity and at the same time do not undergo degradation under thermal stress, such as for example in an extrusion process or in injection moulding, and that may also be used in the melt transesterification process.
It has now surprisingly been found that this object is achieved by the use of terminal groups having a special branched, in particular dendrimer-like structure. These terminal groups positively influence the zero shear viscosity, i.e. the corresponding polycarbonate with a comparable molecular weight distribution exhibits a lower Zero shear viscosity and can therefore be processed more readily. In particular these special terminal groups have the advantage that they are also stable at high temperatures.
Phenolic terminal groups for polycarbonates having a dendrimer-like structure based on carbonyl-bridged or ether-bridged aryl systems have not hitherto been known.
The present invention accordingly provides polycarbonates, polyester carbonates and polyesters that contain branched, in particular dendrimer-like terminal groups based on aryl-CO- and/or aryl-O-couplings, the use of such polycarbonates, and special phenolic terminal groups suitable for use in the polycarbonates according to the invention, and/or the phenolic compounds on which the terminal groups are based.
The present invention accordingly also provides for the use of the phenolic compounds according to formula (1) for the production of terminal group-modified polymers and the phenolic compounds of the formula (2), as well as their preparation.
The phenolic compounds of the formula (1) are defined as follows:
HO—Ar
1
—X—Ar
2
—[Y—W]
n
  (1)
wherein Ar
1
denotes an optionally substituted mononuclear or polynuclear aromatic parent group, X denotes a single bond or a divalent radical such as —O— or —CO—,
Ar
2
denotes an optionally substituted mononuclear or polynuclear aromatic parent group, Y denotes a single bond or a divalent radical such as —O— or —CO—,
W denotes an optionally substituted mononuclear or polynuclear aromatic parent group or an aliphatic or cycloaliphatic radical, and n is a variable between 1 and 5.
Preferred are phenolic compounds of the formula (1) that correspond more specifically to the formulae (2) and (3):
Compounds of the formula (2)
wherein
R
1
denotes H, linear or branched C
1
-C
18
-alkyl, Cl or Br, preferably H or linear or branched C
1
-C
12
-alkyl, particularly preferably H or C
1
-C
8
-alkyl, and most particularly preferably H,
X denotes a single bond or a divalent radical such as —O— or —CO—,
R
2
denotes H, linear or branched C
1
-C
18
-alkyl, Cl or Br, preferably H or linear or branched C
1
-C
12
-alkyl, particularly preferably H or C
1
-C
8
-alkyl, and most particularly preferably all denote the same radical, especially H,
Y denotes a single bond or a divalent radical such as —O— or —CO—,
R
3
, R
7
independent from each other denote H, linear or branched C
1
-C
18
-alkyl, cyclic C
5
-C
18
-alkyl, phenyl, phenyloxy, phenylcarboxy, benzyl, benzyloxy, naphthyl, naphthyloxy or naphthylcarboxy radicals, preferably R
3
equals R
7
equals H, linear or branched C
1
-C
12
-alkyl, cyclic C
5
-C
12
-alkyl, phenyl, phenyloxy, benzyloxy or naphthyloxy radicals, and particularly preferably H, linear or branched C
1
-C
12
-alkyl, cyclic C
5
-C
12
-alkyl, phenyl or phenyloxy radicals, very particularly preferred R
3
and R
7
denote the same group or residue.
m is a number between 0 and 3, n is a number between 2 and 5, wherein m and n must total ≦5. Particularly preferred is the combination in which m=0 and n=2.
Compounds of the formula (3)
wherein
X and Y have the meanings

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