US5644017A
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US
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Polycarbonate terminated by an ionic sulfonated aromatic moiety and preparation thereof
Assignee: Dow Chemical Co
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Filing: 1995-08-25
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Granted: 1997-07-01
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Expires: 2015-08-25
Abstract
Abstract An aromatic polycarbonate is terminated by an ionic sulfonated aromatic moiety bonded to the polycarbonate by a carbonate or ester linkage. The aromatic polycarbonate can be terminated by reacting a sulfonated aromatic compound such as a sulfonated phenol, sulfonated benzoic acid, phenyl ester of a sulfonated aromatic carboxylic acid and sulfonated diphenyl carbonate with an aromatic polycarbonate, an aromatic dihydroxy compound and a carbonate precursor, or a combination thereof. The reaction can be performed in a nonaqueous solution or a melt transesterification process. The aromatic sulfonated terminated polycarbonate can be thermally molded and displays non-newtonian melt rheology and improved solvent resistance.
Inventors
- 👤 Ray E. Drumright
- 👤 Michael J. Mullins
- 👤 Stephen E. Bales
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:09
CPC Classifications
C; C08; C08G; C08G64/00; C08G64/04; C08G64/06; C08G64/08; C08G64/081; C08G64/14; C08G64/42
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
97 words
A polycarbonate comprising a thermoplastic aromatic polycarbonate which has a plurality of terminating groups wherein at least about 10 mole percent of said terminating groups are an aromatic sulfonated terminating (ASTer) group having the structure: ##STR7## wherein R is an aromatic group, and M is selected from the group consisting of hydrogen, a quaternary nitrogen group, a quaternary phosphorous group, an alkali metal, zinc, tin, aluminum and an alkaline earth metal, the thermoplastic aromatic polycarbonate having reduced solubility in a chlorinated solvent compared to an aromatic polycarbonate of similar molecular weight without said aromatic sulfonated terminating groups.
Claim 2
Dependent Claim
97 words
A polycarbonate comprising a thermoplastic aromatic polycarbonate which has a plurality of terminating groups wherein at least about 10 mole percent of said terminating groups are an aromatic sulfonated terminating (ASTer) group having the structure: ##STR7## wherein R is an aromatic group, and M is selected from the group consisting of hydrogen, a quaternary nitrogen group, a quaternary phosphorous group, an alkali metal, zinc, tin, aluminum and an alkaline earth metal, the thermoplastic aromatic polycarbonate having reduced solubility in a chlorinated solvent compared to an aromatic polycarbonate of similar molecular weight without said aromatic sulfonated terminating groups.
Claim 3
Dependent Claim
21 words
The thermoplastic aromatic polycarbonate of claim 1 wherein at least 20 mole percent of the terminating groups are an ASTer group.
Claim 4
Dependent Claim
21 words
The thermoplastic aromatic polycarbonate of claim 2 wherein at least 50 mole percent of the terminating groups are an ASTer group.
Claim 5
Dependent Claim
11 words
The thermoplastic aromatic polycarbonate of claim 1 wherein R is phenylene.
Claim 6
Dependent Claim
25 words
The thermoplastic aromatic polycarbonate of claim 1 wherein M is selected from the group consisting of alkali metal, alkaline earth metal, zinc, tin and aluminum.
Claim 7
Dependent Claim
11 words
The thermoplastic aromatic polycarbonate of claim 5 wherein M is sodium.
Claim 8
Dependent Claim
24 words
The thermoplastic aromatic polycarbonate of claim 1 wherein the thermoplastic aromatic polycarbonate is essentially immiscible in methylene chloride after 24 hours at room temperature.
Claim 9
Dependent Claim
13 words
The process of claim 7 wherein the nonaqueous solvent is a chlorinated hydrocarbon.
Claim 10
Dependent Claim
12 words
The process of claim 8 wherein the nonaqueous solvent is methylene chloride.
Claim 11
Dependent Claim
20 words
The process of claim 7 wherein the aromatic dihydroxy compound is an aromatic diol and the carbonate precursor is phosgene.
Claim 12
Dependent Claim
12 words
The process of claim 10 wherein the aromatic diol is bisphenol A.
Claim 13
Dependent Claim
18 words
The process of claim 7 wherein the aromatic polycarbonate is an aromatic polycarbonate terminated by a phenol group.
Claim 14
Dependent Claim
35 words
The process of claim 7 further comprising reacting the aromatic polycarbonate terminated by an aromatic sulfonated terminating group to form an aromatic polycarbonate terminated by an aromatic sulfonated terminating group having a different cation M.
Claim 15
Dependent Claim
185 words
A process to make an aromatic polycarbonate having improved solvent resistance and non-Newtonian melt rheology, the process comprising melting (A), a sulfonated aromatic terminating compound having the structure: ##STR8## wherein R is an aromatic group, R 3 is --SO3M in which M is hydrogen, a quaternary nitrogen group, a quaternary phosphorous group, an alkali metal, zinc, tin, aluminum or an alkaline earth metal, and R 4 is (a) HO--, (b) R 5 O(O)C-- in which R 5 is hydrogen, an alkyl group or an aromatic group, or (c) R 6 O(O)CO-- in which R 6 is an alkyl group or an aromatic group, with (B), (i) an aromatic polycarbonate, (ii) an aromatic dihydroxy compound and a carbonate precursor, or (iii) a combination thereof, at a temperature above the melting temperature of the aromatic polycarbonate, aromatic dihydroxy compound or carbonate precursor for a time and subatmospheric pressure sufficient to react (A) with (B) to form an aromatic polycarbonate having a plurality of terminating groups wherein at least about 10 mole percent of the terminating groups of the aromatic polycarbonate are an aromatic sulfonated terminating (ASTer) group.
Claim 16
Dependent Claim
185 words
A process to make an aromatic polycarbonate having improved solvent resistance and non-Newtonian melt rheology, the process comprising melting (A), a sulfonated aromatic terminating compound having the structure: ##STR8## wherein R is an aromatic group, R 3 is --SO3M in which M is hydrogen, a quaternary nitrogen group, a quaternary phosphorous group, an alkali metal, zinc, tin, aluminum or an alkaline earth metal, and R 4 is (a) HO--, (b) R 5 O(O)C-- in which R 5 is hydrogen, an alkyl group or an aromatic group, or (c) R 6 O(O)CO-- in which R 6 is an alkyl group or an aromatic group, with (B), (i) an aromatic polycarbonate, (ii) an aromatic dihydroxy compound and a carbonate precursor, or (iii) a combination thereof, at a temperature above the melting temperature of the aromatic polycarbonate, aromatic dihydroxy compound or carbonate precursor for a time and subatmospheric pressure sufficient to react (A) with (B) to form an aromatic polycarbonate having a plurality of terminating groups wherein at least about 10 mole percent of the terminating groups of the aromatic polycarbonate are an aromatic sulfonated terminating (ASTer) group.
Claim 17
Dependent Claim
17 words
The process of claim 14 wherein the reaction is performed in the presence of a basic catalyst.
Claim 18
Dependent Claim
12 words
The process of claim 15 wherein the basic catalyst is lithium hydroxide.
Claim 19
Dependent Claim
19 words
The process of claim 14 wherein the carbonate precursor is diphenyl carbonate and the dihydroxy compound is bisphenol A.
Claim 20
Dependent Claim
23 words
The process of claim 14 wherein the aromatic polycarbonate is a polycarbonate which is a product of bisphenol A and a carbonate precursor.
Claim 21
Dependent Claim
25 words
The process of claim 14 wherein the sulfonated aromatic terminating compound is a phenyl ester of a sulfonated aromatic carboxylic acid or a sulfonated diphenylcarbonate.
Claim 22
Dependent Claim
186 words
A process to make an aromatic polycarbonate having improved flame resistance and non-Newtonian melt rheology, the process comprising dissolving (A), a sulfonated aromatic terminating compound having a structure: ##STR9## wherein R is an aromatic group, R 1 is --S(O)2J in which J is (a) a halogen or (b) --OM s where M s is hydrogen, a quaternary phosphorous group, or a quaternary nitrogen group, R2 is (1) HO-- provided that J is --OM s , (2) XC(O)O-- in which X is a halogen and provided that J is --OM s , (3) HO(O)C-- provided that J is a halogen, or (4) X(O)C-- in which X is a halogen, with (B), (i) an aromatic polycarbonate, (ii) an aromatic dihydroxy compound and a carbonate precursor, or (iii) a combination thereof, in a nonaqueous solvent in the substantial absence of water and in the presence of an organo amino base for a time and temperature sufficient to form an aromatic polycarbonate having a plurality of terminating groups wherein at least about 10 mole percent of the terminating groups of the aromatic polycarbonate are an aromatic sulfonated terminating (ASTer) group.
Claim 23
Dependent Claim
186 words
A process to make an aromatic polycarbonate having improved flame resistance and non-Newtonian melt rheology, the process comprising dissolving (A), a sulfonated aromatic terminating compound having a structure: ##STR9## wherein R is an aromatic group, R 1 is --S(O)2J in which J is (a) a halogen or (b) --OM s where M s is hydrogen, a quaternary phosphorous group, or a quaternary nitrogen group, R2 is (1) HO-- provided that J is --OM s , (2) XC(O)O-- in which X is a halogen and provided that J is --OM s , (3) HO(O)C-- provided that J is a halogen, or (4) X(O)C-- in which X is a halogen, with (B), (i) an aromatic polycarbonate, (ii) an aromatic dihydroxy compound and a carbonate precursor, or (iii) a combination thereof, in a nonaqueous solvent in the substantial absence of water and in the presence of an organo amino base for a time and temperature sufficient to form an aromatic polycarbonate having a plurality of terminating groups wherein at least about 10 mole percent of the terminating groups of the aromatic polycarbonate are an aromatic sulfonated terminating (ASTer) group.
Claim 24
Dependent Claim
15 words
The process of claim 14 wherein the sulfonated aromatic terminating compound is soluble in (B).
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