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US4303759A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyalkylenecarbonate compositions with improved thermal stability and method for making same

Assignee: PAC POLYMER Inc A CORP OF
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Filing: 1980-09-12
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Granted: 1981-12-01
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Expires: 2000-09-12
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Abstract

Abstract Polyalkylene carbonates are stabilized against oxidative degradation by the inclusion therein of 0.2-10%, preferably 1-5%, of peroxyl-reactive sulphur-containing additive. Such compounds, found to be effective, are 3-t-butyl-4-hydroxy-5-methylphenyl sulfide, diphenyl sulfide, diphenyl sulfoxide, diphenyl sulfone, di-(p-tolyl sulfide) and sulphur.

Inventors

  • 👤 Dale D. Dixon
  • 👤 Michael E. Ford

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 04:43
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/0008; C08K5/005; C08K5/36

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 202 words
A polyalkylene carbonate composition having improved thermal stability formed by reacting (a) a normally solid polycarbonate having substantially alternating epoxide and carbon dioxide units and a plurality of free hydroxyl groups represented by the formula: ##STR5## wherein: R 1 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 3 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 2 and R 4 are hydrogen or a hydrocarbyl group having from 1 to 6 carbon atoms; or R 1 , R 2 , R 3 and R 4 are combined together constituting a carbocyclic ring of from 4 to 7 carbon atoms and n is the number of repeating units, which ranges from about 250 to 6,500, and end-capped modifications thereof with (b) 0.2-10%, by weight (based on the weight of polycarbonate to be stabilized) of a sulphur-containing peroxyl radical-reactive compound from the group consisting of metal salts of dithiocarbamic acids; aliphatic and aromatic thiols, sulfides, sulfoxides, sulfones, sulfonic acids, and sulfinic acids; aliphatic and aromatic disulfides; aliphatic and aromatic thioesters and thioamides; aliphatic and aromatic thiophosphite esters and thiophosphonates; and aliphatic and aromatic phosphotrithionites and phosphotrithronates.
Claim 2
Dependent Claim 202 words
A polyalkylene carbonate composition having improved thermal stability formed by reacting (a) a normally solid polycarbonate having substantially alternating epoxide and carbon dioxide units and a plurality of free hydroxyl groups represented by the formula: ##STR5## wherein: R 1 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 3 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 2 and R 4 are hydrogen or a hydrocarbyl group having from 1 to 6 carbon atoms; or R 1 , R 2 , R 3 and R 4 are combined together constituting a carbocyclic ring of from 4 to 7 carbon atoms and n is the number of repeating units, which ranges from about 250 to 6,500, and end-capped modifications thereof with (b) 0.2-10%, by weight (based on the weight of polycarbonate to be stabilized) of a sulphur-containing peroxyl radical-reactive compound from the group consisting of metal salts of dithiocarbamic acids; aliphatic and aromatic thiols, sulfides, sulfoxides, sulfones, sulfonic acids, and sulfinic acids; aliphatic and aromatic disulfides; aliphatic and aromatic thioesters and thioamides; aliphatic and aromatic thiophosphite esters and thiophosphonates; and aliphatic and aromatic phosphotrithionites and phosphotrithronates.
Claim 3
Dependent Claim 14 words
The polycarbonate of claim 1, wherein R 2 and R 4 are hydrogen atoms.
Claim 4
Dependent Claim 18 words
The composition of claim 2 wherein R 1 is selected from the group consisting of hydrogen and phenyl.
Claim 5
Dependent Claim 19 words
The polycarbonate of claim 3 wherein R 3 is selected from the group consisting of hydrogen and methyl groups.
Claim 6
Dependent Claim 12 words
The polycarbonate of claim 4 wherein n is about 500 to 1,500.
Claim 7
Dependent Claim 22 words
A composition as recited in any of claims 1-5, wherein said polycarbonate is reacted with 1-5% by weight, of said peroxyl-reactive compound.
Claim 8
Dependent Claim 14 words
A composition, as recited in claim 6, wherein said peroxyl-reactive compound is 3-t-butyl-4-hydroxy-5-methyl-phenol sulfide.
Claim 9
Dependent Claim 14 words
A composition, as recited in claim 6, wherein said peroxyl-reactive compound is diphenyl sulfide.
Claim 10
Dependent Claim 14 words
A composition, as recited in claim 6, wherein said peroxyl-reactive compound is diphenyl sulfoxide.
Claim 11
Dependent Claim 14 words
A composition, as recited in claim 6, wherein said peroxyl-reactive compound is diphenyl sulfone.
Claim 12
Dependent Claim 14 words
A composition, as recited in claim 6, wherein said peroxyl-reactive compound is di-(p-tolyl sulfide).
Claim 13
Dependent Claim 13 words
A composition, as recited in claim 6, wherein said peroxyl-reactive compound is sulphur.
Claim 14
Dependent Claim 235 words
A process for improving the thermal stability of normally solid polycarbonate and end-capped polycarbonate resins, said resins comprising a compound having substantially alternating epoxide and carbon dioxide units and a plurality of free hydroxyl groups represented by the formula: ##STR6## wherein: R 1 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 3 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 2 and R 4 are hydrogen or a hydrocarbyl group having from 1 to 6 carbon atoms; or R 1 , R 2 , R 3 and R 4 are combined together constituting a carbocyclic ring of from 4 to 7 carbon atoms and n is the number of repeating units, which ranges from about 250 to 6,500, and end-capped modifications thereof, said process comprising (a) forming a solution of said resin, (b) adding thereto 0.2-10%, by weight, (based on the weight of polycarbonate to be stabilized), of a sulphur-containing peroxide radical decomposer compound from the group consisting of metal salts of dithiocarbamic acids; aliphatic and aromatic thiols, sulfides, sulfoxides, sulfones, sulfonic acids, and sulfinic acids; aliphatic and aromatic disulfides; aliphatic and aromatic thioesters and thioamides; aliphatic and aromatic thiophosphite esters and thiophosphonates; and aliphatic and aromatic phosphotrithionites and phosphotrithionates, (c) removing solvent therefrom, and (d) subjecting and resultant resin and additive mixture to heat curing conditions.
Claim 15
Dependent Claim 235 words
A process for improving the thermal stability of normally solid polycarbonate and end-capped polycarbonate resins, said resins comprising a compound having substantially alternating epoxide and carbon dioxide units and a plurality of free hydroxyl groups represented by the formula: ##STR6## wherein: R 1 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 3 is hydrogen, a halomethyl group, or a hydrocarbyl group having from 1 to 6 carbon atoms; R 2 and R 4 are hydrogen or a hydrocarbyl group having from 1 to 6 carbon atoms; or R 1 , R 2 , R 3 and R 4 are combined together constituting a carbocyclic ring of from 4 to 7 carbon atoms and n is the number of repeating units, which ranges from about 250 to 6,500, and end-capped modifications thereof, said process comprising (a) forming a solution of said resin, (b) adding thereto 0.2-10%, by weight, (based on the weight of polycarbonate to be stabilized), of a sulphur-containing peroxide radical decomposer compound from the group consisting of metal salts of dithiocarbamic acids; aliphatic and aromatic thiols, sulfides, sulfoxides, sulfones, sulfonic acids, and sulfinic acids; aliphatic and aromatic disulfides; aliphatic and aromatic thioesters and thioamides; aliphatic and aromatic thiophosphite esters and thiophosphonates; and aliphatic and aromatic phosphotrithionites and phosphotrithionates, (c) removing solvent therefrom, and (d) subjecting and resultant resin and additive mixture to heat curing conditions.
Claim 16
Dependent Claim 20 words
A process, as recited in claim 13, wherein 1-5%, by weight, of diphenyl sulfide is added as said decomposer compound.
Claim 17
Dependent Claim 20 words
A process, as recited in claim 13, wherein 1-5%, by weight, of diphenyl sulfoxide is added as said decomposer compound.
Claim 18
Dependent Claim 20 words
A process, as recited in claim 13, wherein 1-5%, by weight, of diphenyl sulfone is added as said decomposer compound.
Claim 19
Dependent Claim 19 words
A process, as recited in claim 13, wherein 1-5%, by weight, of di-(p-tolyl sulfide) is added as said decomposer.
Claim 20
Dependent Claim 19 words
A process, as recited in claim 13, wherein 1-5%, by weight, of sulphur is added as said decomposer compound.
Claim 21
Dependent Claim 32 words
Process, as recited in any one of claims 14 to 18, wherein said heat curing conditions comprise subjecting said resultant mixture to a temperature of about 150° C. for about 15-20 minutes.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-11-30 1985-06-01 1985-12-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-11-30 1989-06-01 1989-12-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-11-30 1993-06-01 1993-12-01 $7700.00 Window Closed / Lapsed

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