# US 4,393,156 A · Hydrolytically stable polyester-carbonate compositions

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- Number: US 4,393,156 A
- Document ID: US4393156A
- Status: Granted
- Kind: A
- Application number: 06/285,351
- Filed: 1981-07-20
- Granted: 1983-07-12
- Earliest claimed: 1981-07-20
- Assignees: General Electric Company
- Inventors: Kenneth F. Miller
- Web page: https://patentgrep.com/patent/US4393156A

## CPC

- C08K 5/5435: containing oxygen in a ring
- C08K 5/54: Silicon-containing compounds {(C08K5/0091 takes precedence)}
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

An improved hydrolytically stable aromatic polyester-carbonate composition comprising in admixture an aromatic polyester-carbonate resin and a hydrolytically stabilizing amount of at least one stabilizing compound selected from epoxy silanes and epoxy siloxanes.

## Claims

### Claim 1

An aromatic polyester-carbonate composition having improved hydrolytic stability comprising in admixture an aromatic polyester-carbonate resin and a stabilizing amount of at least one hydrolytic stabilizer selected from the class consisting of epoxy silanes and epoxy siloxanes.

### Claim 2 (depends on 1)

The composition of claim 1 wherein said stabilizer is present in an amount of from about 0.005 to about 4 weight percent based on the weight of the aromatic polyester-carbonate resin.

### Claim 3 (depends on 2)

The composition of claim 2 wherein said epoxy silanes are represented by the general formula
Z.sub.n Si(R.sup.3).sub.4-n
wherein n is an integer from 1 to 3 inclusive; Z is a monovalent epoxy radical; and R.sup.3 is independently selected from hydrogen; alkyl radicals; substituted alkyl radicals; cycloalkyl radicals; alkenyl radicals; aryl radicals; alkaryl radicals; aralkyl radicals; divalent organic radicals which together with the Si atom form a cyclic structure, said organic radicals being selected from divalent saturated aliphatic hydrocarbon radicals and the divalent saturated aliphatic organic radicals containing carbon and oxygen atoms in the ring structure; OR.sup.4 radicals wherein R.sup.4 is selected from hydrogen, alkyl radicals, substituted alkyl radicals; alkenyl radicals, aryl radicals, aralkyl radicals, alkaryl radicals, and cycloalkyl radicals; --R.sup.5 OR.sup.4 radicals wherein R.sup.5 is a divalent saturated aliphatic hydrocarbon radical or a divalent aromatic hydrocarbon radical; --COOR.sup.4 radicals; --OOCR.sup.4 radicals; --R.sup.5 COOR.sup.4 radicals; --R.sup.5 OOCR.sup.4 radicals; and polyether radicals.

### Claim 4 (depends on 3)

The composition of claim 3 wherein said monovalent epoxy radical is represented by the general formula ##STR12## wherein: (i) R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are independently selected from the class consisting of hydrogen; alkyl radicals; substituted alkyl radicals; cycloalkyl radicals; alkenyl radicals; aryl radicals; aralkyl radicals; alkaryl radicals; OR.sup.13 radicals wherein R.sup.13 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, alkenyl radicals, aryl radicals, aralkyl radicals, and alkaryl radicals; --R.sup.14 OR.sup.13 radicals wherein R.sup.14 is a divalent saturated aliphatic hydrocarbon radical or a divalent aromatic hydrocarbon radical; --OOCR.sup.13 radicals; --R.sup.14 OOCR.sup.13 radicals; --COOR.sup.13 radicals; --R.sup.14 COOR.sup.13 radicals; OR.sup.15 radicals wherein R.sup.15 is selected from the class consisting of oxirane ring containing monovalent saturated aliphatic hydrocarbon radicals and oxirane ring containing monovalent aliphatic-aromatic hydrocarbon radicals; --OOCR.sup.15 radicals; --COOR.sup.15 radicals; --R.sup.14 OOCR.sup.15 radicals; and --R.sup.14 COOR.sup.15 radicals; with the proviso that
(ii) one of R.sup.9, R.sup.10, R.sup.11 or R.sup.12 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; --OR.sup.16 -- radicals wherein R.sup.16 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals and divalent aromatic hydrocarbon radicals; --R.sup.14 OR.sup.16 -- radicals; --R.sup.14 OOCR.sup.16 -- radicals; --R.sup.14 COOR.sup.16 -- radicals; --COOR.sup.16 -- radicals; and --OOCR.sup.16 -- radicals.

### Claim 5 (depends on 4)

The composition of claim 4 wherein:
(i) R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are independently selected from the class consisting of hydrogen; alkyl radicals; substituted alkyl radicals; cycloalkyl radicals; aryl radicals; alkaryl radicals; araalkyl radicals; and OR.sup.17 radicals wherein R.sup.17 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, aryl radicals, alkaryl radicals, and aralkyl radicals; with the proviso that
(ii) one of R.sup.9, R.sup.10, R.sup.11 or R.sup.12 is selected from the class consisting if divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; OR.sup.16 -- radicals; and --R.sup.14 OR.sup.16 -- radicals.

### Claim 6 (depends on 5)

The composition of claim 5 wherein R.sup.3 is selected from hydrogen; alkyl radicals; hydroxyl; alkoxy radicals; aryl radicals; aryloxy radicals; alkaryl radicals; and aralkyl radicals.

### Claim 7 (depends on 6)

The composition of claim 6 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative thereof, and (c) a carbonate precursor.

### Claim 8 (depends on 7)

The composition of claim 7 wherein said carbonate precursor is phosgene.

### Claim 9 (depends on 8)

The composition of claim 8 wherein said aromatic dicarboxylic acid is selected from the class consisting of terephthalic acid, isophthalic acid, and mixtures thereof.

### Claim 10 (depends on 8)

The composition of claim 8 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of isophthloyl dichloride, terephthaloyl dichloride, and mixtures thereof.

### Claim 11 (depends on 10)

The composition of claim 10 wherein said dihydric phenol is bisphenol A.

### Claim 12 (depends on 11)

The composition of claim 11 wherein said epoxy silane is gamma-glycidoxypropyl-trimethoxysilane.

### Claim 13 (depends on 6)

The composition of claim 6 which further contains an organophosphite color stabilizer.

### Claim 14 (depends on 13)

The composition of claim 13 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative thereof, and (c) a carbonate precursor.

### Claim 15 (depends on 14)

The composition of claim 14 wherein said carbonate precursor is phosgene.

### Claim 16 (depends on 15)

The composition of claim 15 wherein said aromatic dicarboxylic acid is selected from the class consisting of terephthalic acid, isophthalic acid, and mixtures thereof.

### Claim 17 (depends on 15)

The composition of claim 15 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of terephthaloyl dichloride, isophthaloyl dichloride, and mixtures thereof.

### Claim 18 (depends on 17)

The composition of claim 17 wherein said dihydric phenol is bisphenol A.

### Claim 19 (depends on 18)

The composition of claim 18 wherein said epoxy silane is gamma-glycidoxypropyl-trimethoxysilane.

### Claim 20 (depends on 3)

The composition of claim 3 wherein said monovalent epoxy radical is represented by the general formula ##STR13## wherein: (i) R.sup.18 through R.sup.27 are independently selected from hydrogen; alkyl radicals; substituted alkyl radicals; alkenyl radicals; aryl radicals; aralkyl radicals; alkaryl radicals; OR.sup.29 radicals wherein R.sup.29 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, alkenyl radicals, aryl radicals, alkaryl radicals, and aralkyl radicals; --R.sup.30 OR.sup.29 radicals wherein R.sup.30 is a divalent saturated aliphatic hydrocarbon radical or a divalent aromatic hydrocarbon radical; --COOR.sup.29 radicals; --OOCR.sup.29 radicals; --R.sup.30 OOCR.sup.29 radicals; --R.sup.30 COOR.sup.29 radicals; OR.sup.31 radicals wherein R.sup.31 is selected from the class consisting of oxirane ring containing saturated aliphatic hydrocarbon radicals and oxirane ring containing aliphatic-aromatic hydrocarbon radicals; --R.sup.30 OR.sup.31 radicals; --OOCR.sup.31 radicals; --COOR.sup.31 radicals; --R.sup.30 OOCR.sup.31 radicals; and --R.sup.30 COOR.sup.31 radicals; with the proviso that
(ii) one of R.sup.18 through R.sup.27 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; --OR.sup.32 -- radicals wherein R.sup.32 is selected from divalent saturated aliphatic hydrocarbon radicals and divalent aromatic hydrocarbon radicals; --R.sup.30 OR.sup.32 -- radicals; --OOCR.sup.32 -- radicals; --COOR.sup.32 -- radicals; --R.sup.30 OOCR.sup.32 -- radicals; and --R.sup.30 COOR.sup.32 -- radicals.

### Claim 21 (depends on 20)

The composition of claim 20 wherein:
(i) R.sup.18 through R.sup.27 are independently selected from hydrogen; alkyl radicals; substituted alkyl radicals; aryl radicals; aralkyl radicals; alkaryl radicals; and OR.sup.28 radicals wherein R.sup.28 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, aryl radicals, alkaryl radicals, and aralkyl radicals; with the proviso that
(ii) one of R.sup.18 through R.sup.27 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; --OR.sup.32 -- radicals; and --R.sup.30 OR.sup.32 -- radicals.

### Claim 22 (depends on 21)

The composition of claim 21 wherein R.sup.3 is selected from hydrogen; alkyl radicals; alkoxy radicals; hydroxyl; aryl radicals; aryloxy radicals; alkaryl radicals; and aralkyl radicals.

### Claim 23 (depends on 22)

The composition of claim 22 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative thereof, and (c) a carbonate precursor.

### Claim 24 (depends on 23)

The composition of claim 23 wherein said carbonate precursor is phosgene.

### Claim 25 (depends on 24)

The composition of claim 24 wherein said aromatic dicarboxylic acid is selected from the class consisting of terephthalic acid, isophthalic acid, and mixtures thereof.

### Claim 26 (depends on 24)

The composition of claim 24 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of isophthaloyl dichloride, terephthaloyl dichloride, and mixtures thereof.

### Claim 27 (depends on 26)

The composition of claim 26 wherein said dihydric phenol is bisphenol A.

### Claim 28 (depends on 27)

The composition of claim 27 wherein said epoxy silane is beta(3,4-epoxycyclohexyl)ethyltrimethoxy-silane.

### Claim 29 (depends on 22)

The composition of claim 22 which further contains a color stabilizing amount of an organophsopshite color stabilizer.

### Claim 30 (depends on 29)

The composition of claim 29 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative thereof, and (c) a carbonate precursor.

### Claim 31 (depends on 30)

The composition of claim 30 wherein said carbonate precursor is phosgene.

### Claim 32 (depends on 31)

The composition of claim 31 wherein said aromatic dicarboxylic acid is selected from the class consisting of terephthalic acid, isophthalic acid, and mixtures thereof.

### Claim 33 (depends on 31)

The composition of claim 31 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of isophthaloyl dichloride, terephthaloyl dichloride, and mixtures thereof.

### Claim 34 (depends on 33)

The composition of claim 33 wherein said dihydric phenol is bisphenol A.

### Claim 35 (depends on 34)

The composition of claim 34 wherein said epoxy silane is beta(3,4-epoxycyclohexyl)ethyltrimethoxy-silane.

### Claim 36 (depends on 2)

The composition of claim 2 wherein said epoxy siloxanes are represented by the general formula ##STR14## wherein: (i) a is an integer having a value of from 1 to about 10;
(ii) R.sup.33 and R.sup.34 are independently selected from alkyl radicals, alkenyl radicals, alkoxy radicals, aryl radicals, aryloxy radicals, aralkyl radicals, alkaryl radicals, and hydrogem; and
(iii) each Z is independently selected from monovalent epoxy radicals.

### Claim 37 (depends on 36)

The composition of claim 36 wherein said monovalent epoxy radical is represented by the general formula ##STR15## wherein: (i) R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are independently selected from the class consisting of hydrogen; alkyl radicals; substituted alkyl radicals; cycloalkyl radicals; alkenyl radicals; aryl radicals; aralkyl radicals; alkaryl radicals; OR.sup.13 radicals wherein R.sup.13 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, alkenyl radicals, aryl radicals, aralkyl radicals, and alkaryl radicals; --R.sup.14 OR.sup.13 radicals wherein R.sup.14 is a divalent saturated aliphatic hydrocarbon radical or a divalent aromatic hydrocarbon radical; --OOCR.sup.13 radicals; --COOR.sup.13 radicals; --R.sup.14 COOR.sup.13 radicals; --R.sup.14 OOCR.sup.13 radicals; OR.sup.15 radicals wherein R.sup.15 is selected from the class consisting of oxirane ring containing monovalent saturated aliphatic hydrocarbon radicals and oxirane ring containing monovalent aliphatic-aromatic hydrocarbon radicals; --OOCR.sup.15 radicals; --COOR.sup.15 radicals; --R.sup.14 OOCR.sup.15 radicals; and --R.sup.14 COOR.sup.15 radicals; with the proviso that
(ii) one of R.sup.9, R.sup.10, R.sup.11 or R.sup.12 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; --OR.sup.16 -- radicals wherein R.sup.16 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals and divalent aromatic hydrocarbon radicals; --R.sup.14 OR.sup.16 -- radicals; --R.sup.14 OOCR.sup.16 -- radicals; --R.sup.14 COOR.sup.16 -- radicals; --COOR.sup.16 -- radicals; and --OOCR.sup.16 -- radicals.

### Claim 38 (depends on 37)

The composition of claim 37 wherein:
(i) R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are independently selected from the class consisting of hydrogen; alkyl radicals, substituted alkyl radicals, cycloalkyl radicals; aryl radicals; alkaryl radicals; aralkyl radicals; and OR.sup.17 radicals wherein R.sup.17 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, aryl radicals, alkaryl radicals, and aralkyl radicals; with the proviso that
(ii) one of R.sup.9, R.sup.10, R.sup.11 or R.sup.12 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; OR.sup.16 -- radicals; and --R.sup.14 OR.sup.16 -- radicals.

### Claim 39 (depends on 38)

The composition of claim 38 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative of an aromatic dicarboxylic acid, and (c) a carbonate precursor.

### Claim 40 (depends on 39)

The composition of claim 39 wherein said carbonate precursor is phosgene.

### Claim 41 (depends on 40)

The composition of claim 40 wherein said aromatic dicarboxylic acid is selected from the class consisting of isophthalic acid, terephthalic acid, and mixtures thereof.

### Claim 42 (depends on 40)

The composition of claim 40 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of isophthaloyl dichloride, terephthaloyl dichloride, and mixtures thereof.

### Claim 43 (depends on 42)

The composition of claim 42 wherein said dihydric phenol is bisphenol A.

### Claim 44 (depends on 38)

The composition of claim 38 which further contains a color stabilizing amount of an organophosphite color stabilizer.

### Claim 45 (depends on 44)

The composition of claim 44 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative of an aromatic dicarboxylic acid, and (c) a carbonate precursor.

### Claim 46 (depends on 45)

The composition of claim 45 wherein said carbonate precursor is phosgene.

### Claim 47 (depends on 46)

The composition of claim 46 wherein said aromatic dicarboxylic acid is selected from the class consisting of isophthalic acid, terephthalic acid, and mixtures thereof.

### Claim 48 (depends on 46)

The composition of claim 46 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of isophthaloyl dichloride, terephthaloyl dichloride, and mixtures thereof.

### Claim 49 (depends on 48)

The composition of claim 48 wherein said dihydric phenol is bisphenol A.

### Claim 50 (depends on 36)

The composition of claim 36 wherein said monovalent epoxy radical is represented by the general formula ##STR16## wherein: (i) R.sup.18 through R.sup.27 are independently selected from hydrogen; alkyl radicals; substituted alkyl radicals; alkenyl radicals; aryl radicals; aralkyl radicals; alkaryl radicals; OR.sup.29 radicals wherein R.sup.29 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, alkenyl radicals, aryl radicals, alkaryl radicals, and aralkyl radicals; --R.sup.30 OR.sup.29 radicals wherein R.sup.30 is a divalent saturated aliphatic hydrocarbon radical or a divalent aromatic hydrocarbon radical; --COOR.sup.29 radicals; --OOCR.sup.29 radicals; --R.sup.30 OOCR.sup.29 radicals; --R.sup.30 COOR.sup.29 radicals; OR.sup.31 radicals wherein R.sup.31 is selected from the class consisting of oxirane ring containing saturated aliphatic hydrocarbon radicals and oxirane ring containing aliphatic-aromatic hydrocarbon radicals; --R.sup.30 OR.sup.31 radicals; --OOCR.sup.31 radicals; --COOR.sup.- radicals; --R.sup.30 OOCR.sup.31 radicals; and --R.sup.30 COOR.sup.31 radicals; with the proviso that
(ii) one of R.sup.18 through R.sup.27 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; --OR.sup.32 -- radicals wherein R.sup.32 is selected from divalent saturated aliphatic hydrocarbon radicals and divalent aromatic hydrocarbon radicals; --R.sup.30 OR.sup.32 -- radicals; --OOCR.sup.32 -- radicals; --COOR.sup.32 -- radicals; --R.sup.30 OOCR.sup.32 -- radicals; and --R.sup.30 COOR.sup.32 -- radicals.

### Claim 51 (depends on 50)

The composition of claim 50 wherein:
(i) R.sup.18 through R.sup.27 are independently selected from hydrogen; alkyl radicals; substituted alkyl radicals; aryl radicals; aralkyl radicals; alkaryl radicals; and OR.sup.28 radicals wherein R.sup.28 is selected from the class consisting of hydrogen, alkyl radicals, substituted alkyl radicals, aryl radicals, alkaryl radicals, and aralkyl radicals; with the proviso that
(ii) one of R.sup.18 through R.sup.27 is selected from the class consisting of divalent saturated aliphatic hydrocarbon radicals; divalent aromatic hydrocarbon radicals; --OR.sup.32 -- radicals; and --R.sup.30 OR.sup.32 -- radicals.

### Claim 52 (depends on 51)

The composition of claim 51 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative of said aromatic dicarboxylic acid, and (c) a carbonate precursor.

### Claim 53 (depends on 52)

The composition of claim 52 wherein said carbonate precursor is phosgene.

### Claim 54 (depends on 53)

The composition of claim 53 wherein said aromatic dicarboxylic acid is selected from the class consisting of isophthalic acid, terephthalic acid, and mixtures thereof.

### Claim 55 (depends on 53)

The composition of claim 53 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of isophthaloyl dichloride, terephthaloyl dichloride, and mixtures thereof.

### Claim 56 (depends on 55)

The composition of claim 55 wherein said dihydric phenol is bisphenol A.

### Claim 57 (depends on 51)

The composition of claim 51 which further contains a color stabilizing amount of an organophsophite color stabilizer.

### Claim 58 (depends on 57)

The composition of claim 57 wherein said aromatic polyester-carbonate resin is derived from (a) a dihydric phenol, (b) at least one aromatic dicarboxylic acid or at least one reactive derivative of said aromatic dicarboxylic acid, and (c) a carbonate precursor.

### Claim 59 (depends on 58)

The composition of claim 58 wherein said carbonate precursor is phosgene.

### Claim 60 (depends on 59)

The composition of claim 59 wherein said aromatic dicarboxylic acid is selected from the class consisting of isophthalic acid, terephthalic acid, and mixtures thereof.

### Claim 61 (depends on 60)

The composition of claim 60 wherein said reactive derivative of said aromatic dicarboxylic acid is selected from the class consisting of isophthaloyl dichloride, terephthaloyl dichloride, and mixtures thereof.

### Claim 62 (depends on 61)

The composition of claim 61 wherein said dihydric phenol is bisphenol A.

### Claim 63 (depends on 43)

The composition of claim 43 wherein said epoxy siloxane is bis(3-glycidoxypropyl)tetramethyldisiloxane.

### Claim 64 (depends on 49)

The composition of claim 49 wherein said epoxy siloxane is bis(3-glycidoxypropyl)tetramethyldisiloxane.

### Claim 65 (depends on 2)

A composition in accordance with claim 2 wherein a color stabilizing effective amount of an organophosphite is present.