Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2002-06-11
2004-08-31
Boykin, Terressa (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C264S176100, C264S219000, C528S193000, C528S194000, C528S198000
Reexamination Certificate
active
06784278
ABSTRACT:
FIELD OF THE INVENTION
The invention concerns polycarbonates, polyester carbonates and polyesters and more particularly to such polymers having phenols with a branched structure as terminal groups.
SUMMARY OF THE INVENTION
The use of phenols having a branched structure as terminal groups in polycarbonates, polyester carbonates and polyesters is disclosed. Also disclosed are polycarbonates, polyester carbonates and polyesters having such branched terminal groups, the process for their production and molded parts made therefrom.
BACKGROUND OF THE INVENTION
Phenol-based monofunctional terminal groups such as e.g. phenol, 4-alkyl phenols and 4-cumyl phenol are commonly used to produce polycarbonates (Kunststoff-Handbuch 3; L. Bottenbruch, Hanser, Munich 1992, p. 127; EP 0 353 594 A1).
It is not known that these conventionally used terminal groups have a positive influence on flow properties and/or zero shear-rate viscosity and hence on the processing properties of the corresponding polycarbonates.
The production of such polycarbonates having branched terminal groups is known in principle and described for example in EP-A 0 794 209 and JP-A 06 256 499.
For example, p-phenyl phenol is known from U.S. Pat. Nos. 3,166,606 and 3,173,891 as a chain terminator for polycarbonates. Polyester carbonates in which 4-benzyl benzoic acid is used as a chain terminator are known from U.S. Pat. No. 4,330,663 (column 6, line 18).
WO-A 00/50 488 describes the use of di-tert.-alkyl phenol as a chain terminator.
Polycarbonates modified with phenyl propyl phenol, alkyl phenols or naphthol as terminal groups are known from the Japanese laid-open application 57 13 31 49.
Polycarbonates having terminal groups with the structures
are known from JP-A 06 25 64 99.
According to DE-A 38 03 939, chain terminators having the formula
are used,
wherein R
1
, R
2
, R
3
are the same or different and are C
2
-C
12
alkyl or C
8
-C
20
aralkyl, whereby at least one of the radicals R
1
or R
2
is a C
8
-C
20
aralkyl radical, and wherein “n” has a value between 0.5 and 1.
These known polycarbonates, polyester carbonates and polyesters often have the disadvantage of a high melt viscosity, however.
The present object is therefore to provide polycarbonates, polyester carbonates and polyesters having suitable phenols as terminal groups, which avoid the disadvantage of a high melt viscosity.
DETAILED DESCRIPTION OF THE INVENTION
Surprisingly it was found that this object is achieved by the use of terminal groups having a special branched, in particular dendrimer-type structure. These terminal groups have a positive influence on the melt viscosity, in other words the corresponding polycarbonate displays a lower melt viscosity with a comparable molecular weight distribution and is therefore more readily processable.
Phenolic terminal groups having a dendrimer-type structure based on ester-bridged or ether-bridged aryl systems have not been known until now.
The present invention therefore provides polycarbonates, polyester carbonates and polyesters containing branched, in particular dendrimer-type terminal groups. The invention also concerns the use of the inventive polymeric resins in producing useful articles.
The present invention therefore also provides the use of the phenols according to formula (1) to produce terminal group-modified polymers and the phenols having formula (2)—excluding bis(C
1
-C
18
alkyl phenyl)-4-hydroxyisophthalates (DE-A 19 62 229), unsubstituted diphenyl hydroxyisophthalate and bis[(diphenyl oxycarbonyl) phenyl] hydroxyisophthalate (T. M. Miller, E. W. Kwock, T. X. Neenan, Macromolecules, 1992, 25, 3143-3148), unsubstituted diphenyl oxyphenol (DE-A 16 44 922), 3,5-dibenzoyl phenol (Dischendorfer et al., Monatsh. Chem. 1935, 66, 255), 4-methyl-2,6-dibenzoyl phenol (S. K. Gupta et al., Transition Met. Chem. 1997, 22, 372-374), 2-methyl-4,6-dibenzoyl phenol (K. C. Amin et al. J. Indian Chem. Soc. 1960, 37, 469-472) and 3,5-bis(4-hydroxybenzoyl) phenol (A. Morikawa, M. Kakimoto, Y. Imai Macromolecules 1993, 26, 6325)—themselves, and the preparation thereof.
The suitable phenols conform to formula (1)
wherein
Ar
1
and AR
2
independently one of the other denote an optionally substituted mononuclear or polynuclear aromatic radical,
X is a single bond or a divalent radical, preferably —CO
2
—, —O—, —CH
2
— or —CO— and
n is 1 to 5.
Preferred phenols conform to formula (2):
wherein
R
1
, R
2
, R
7
independently one of the others denote H, linear or branched C
1
-C
18
alkyl, Cl, or Br, preferably for H or linear or branched C
1
-C
12
alkyl, particularly preferably for H or C
1
-C
8
alkyl and most preferably all denote the same radical, preferably H,
X is a single bond or a divalent radical, such as —CO
2
—, —O—, —CH
2
— or —CO—, preferably an ester group (2a), an ether group (2b) or a carbonyl group (2c),
R
3
-R
6
independently one of the others denote H, linear or branched C
1
-C
18
alkyl, cyclic C
5
-C
18
alkyl, phenyl, phenyloxy, phenyl carboxy, benzyl, benzyloxy, naphthyl or naphthyloxy, naphthylcarboxy radicals, preferably H, linear or branched C
1
-C
12
alkyl, cyclic C
5
-C
12
alkyl, phenyloxy, benzyloxy or naphthyloxy radicals and particularly preferred are the embodiments where these denote the same radical, in particular H, linear or branched C
1
-C
12
alkyl, cyclic C
5
-C
12
alkyl, phenyloxy or benzyloxy radical.
The phenols corresponding to formulae 2a-2c are particularly preferred:
wherein 2a to 2c the radicals R
1
to R
7
have the meanings specified above.
Suitable terminal groups useful for modifying polycarbonates, polyestercarbonates and polyesters are represented by Formula (3):
—O—Ar
1
—[—X—Ar
2
]
n
(3)
wherein Ar 1, X and Ar2 have the meanings specified above.
Preferably suitable are terminal groups according to Formula (3a):
wherein X, and R1-R7 have the meanings specified above.
Independently from each other particularly suitable are the terminal groups derived from Phenols of formulas (2a) to (2c).
Preferred, particularly preferred, very particularly preferred or especially preferred or suitable etc. are such compounds, bearing the as preferred, particularly preferred, very particularly preferred or especially preferred or suitable mentioned Substituents.
The radical definitions and explanations cited above in general terms or in preferential ranges may also be combined with one another in any way, in other words the invention embraces any combination of the individual ranges and preferential ranges. Accordingly these apply both to the end products and to the preliminary and intermediate products.
The present invention therefore also provides thermoplastic polycarbonates, thermoplastic polyester carbonates and thermoplastic polyesters with terminal groups derived from the phenols having formulae (1) and (2).
Examples of phenols having formula (1) are 3,5-diphenyl oxyphenol, 3,5-bis(p-tert.-butyl phenyloxy) phenol, 3,5-bis(p-n-butyl phenyloxy) phenol, 1,3-diphenyl-5-hydroxyisophthalate, 1,3-bis(p-tert.-butyl phenyl)-5-hydroxyisophthalate, 1,3-bis(p-iso-octylphenyl)-5-hydroxyisophthalate, 1,3-bis(3,5-di-tert.-butyl phenyl)-5-hydroxyisophthalate, 1,3-bis[p-(2-phenyl prop-2yl) phenyl]-5-hydroxyisophthalate, 1,3-dicyclooctyl-5-hydroxyisophthalate, 1,3-dicyclododecyl-5-hydroxyisophthalate and 1,3-bis[3,5-(diphenyl oxycarbonyl) phenyl]-5-hydroxyisophthalate.
The monophenols having formula (1) for use according to the invention may be produced by methods known from the literature (T. M. Miller, E. W. Kwock, T. X. Neenan, Macromolecules 1992, 25, 3143-3148, A Morikawa, M. Kakimoto, Y. Imai, Macromolecules 1993, 26, 6324-6329). Of the phenols described in the embodiment examples, 1,3-diphenyl-5-hydroxyisophthalate and 1,3-bis[3,5-(diphenyl oxycarbonyl) phenyl]-5-hydroxyisophthalate (T. M. Miller, E. W. Kwock, T. X. Neenan, Macromolecules 1992, 25, 3143-3148) and 3,5-diphenyloxyphenol (DE A 16 44 922) are known. Of phenols having formula (2a), bis(C
1
-C
18
alkylphenyl)-4-hydroxyisophthalates are known from DE-A 1
Bruder Friedrich-Karl
Heuer Helmut-Werner
Meyer Alexander
Paulusse Jos M. J.
Pielartzik Harald
Bayer Aktiengesellschaft
Boykin Terressa
Gil Joseph C.
Preis Aron
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