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GB1009019A - Bisphenols and polyesters derived therefrom - Google Patents

Bisphenols and polyesters derived therefrom

Info

Publication number
GB1009019A
GB1009019A GB35111/62A GB3511162A GB1009019A GB 1009019 A GB1009019 A GB 1009019A GB 35111/62 A GB35111/62 A GB 35111/62A GB 3511162 A GB3511162 A GB 3511162A GB 1009019 A GB1009019 A GB 1009019A
Authority
GB
United Kingdom
Prior art keywords
bisphenol
bisphenols
acid
formula
catalyst
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB35111/62A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB1009019A publication Critical patent/GB1009019A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/04—Formic acid esters
    • C07C69/08—Formic acid esters of dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6886—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/80—Solid-state polycondensation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/46—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing nine carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
    • C07C2603/64—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings having a tricyclo[2.2.1.0(2,6)]heptstructure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/90—Ring systems containing bridged rings containing more than four rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

The invention comprises linear polymers in which at least 10% o the units have the formula: <FORM:1009019/C3/1> where R11 represents a hydrogen atom, halogen atom, or alkyl group having up to four carbon atoms, and X represents a gem-bivalent radical of a saturated polycyclic compound having at least one bicyclic carbon-bridged hydrocarbon ring, preferably of the formula <FORM:1009019/C3/2> <FORM:1009019/C3/3> <FORM:1009019/C3/4> <FORM:1009019/C3/5> <FORM:1009019/C3/6> <FORM:1009019/C3/7> <FORM:1009019/C3/8> <FORM:1009019/C3/9> <FORM:1009019/C3/100> <FORM:1009019/C3/111> <FORM:1009019/C3/122> <FORM:1009019/C3/133> <FORM:1009019/C3/144> <FORM:1009019/C3/155> <FORM:1009019/C3/166> <FORM:1009019/C3/177> wherein each of R, R1, R11, R1, R11 and R2 represent a hydrogen atom, halogen atom, or alkyl group containing up to 4 carbon atoms, and R1, R11 and R2 can also be aryl groups, and one of the carbon positions marked by an asterisk is the position at which the phenyl groups are joined to the radical. The polymers may be linear polycarbonates in which at least 10% of the units have the formula <FORM:1009019/C3/188> in which X represents a gem-bivalent radical as above and Y is a bifunctional organic residue, which may be prepared from bisphenols by adding phosgene and/or a bischloroformate of a diol, to a cooled, stirred aqueous mixture containing sodium hydroxide, the bisphenol, a catalyst and methylene chloride. The catalyst may be a quaternary ammonium salt or hydroxide, or a tertiary amine. Copolycarbonates are made by using more than one bisphenol or a mixture of diacid chlorides. Block copolycarbonates are made by condensing a mixture of low-molecular weight homopolycarbonates with phosgene. Mixed copolymers are prepared by condensing a bisphenol with a bischloroformate of a polymeric diol, e.g. polyethylene oxide bischloroformates. The polymers may also be linear polyester in which at least 10% of the units have the formula <FORM:1009019/C3/199> in which Z represents a bifunctional organic residue. The polyesters are made by condensing the said bisphenols with dicarboxylic acids, by ester interchange reactions between the novel bisphenols and esters of aliphatic, cycloaliphatic and aromatic dicarboxylic acids. Mixtures containing two or more acids, two or more bisphenols or an aliphatic or cycloaliplatic glycol with the bisphenol, may be used to give co-polyesters. The ester interchange is catalysed by the oxide, hydride or amide of an alkaline earth metal, or zinc oxide, lead oxide, dibutyl tin oxide, and sodium aluminate. Polyester may also be obtained by heating a mixture of equivalent amounts of bisphenol and acid chloride at temperatures from 160-280 DEG C. or reacting them in a basic solvent such as pyridine or a two-phase system of aqueous alkali and organic phase. Another method involves ester interchange of a monobasic aliphatic acid ester of the bisphenol with a dicarboxylic acid. A catalyst such as manganese may be used. Specifications 621,102, 636,429, 648,513, 772,627, 777,215 and 1,009,020 are referred to.ALSO:The invention comprises a bisphenol having the formula <FORM:1009019/C2/1> wherein X has one of the structures <FORM:1009019/C2/2> wherein each of R, R1, R11, R1, R11 and R2 represents a hydrogen atom, halogen atom, or alkyl group containing up to 4 carbon atoms, and R1, R11 and R2 can also be aryl groups and one of the carbon positions marked by an asterisk is the position at which the phenyl groups are joined to the radical. The bisphenols may be made by condensation of phenol with an appropriate polycyclic ketone or aldehyde, preferably in the presence of concentrated hydrochloric acid, though other acids such as sulphuric, toluenesulphonic or methionic acid may also be used as a catalyst. Detailed examples describe the preparation of the various polycyclic bis-phenols from the appropriate ketone or aldehyde. The starting materials are prepared by known methods with the exception of the following: (2) a substituted ethylene, e.g. propylene, 2-butene, styrene, stilbene, p-chloro-styrene, or other homologue containing 3-20 carbon atoms and which may contain up to 6 chlorine atoms, is heated at 200 DEG C. with dicyclopentadiene (which cracks to form cyclopentadiene) to form a bicycloheptene by Diels-Alder reaction, which is hydrated to a norcamphanol followed by oxidation with nitric acid to a substituted norcamphor; (3) 4,7-hexahydromethanoidan-5-ol is oxidized with nitric acid to 4,7-hexahydromethanoidan - 5 - one; (6) decahydro - 1,4-exoendo - 5,8 - dimethano - naphthalene - 2 - one is made by oxidation of the corresponding hydroxy compound with nitric acid; (18) dihydrodicyclopentadiene is reacted with hydrogen and carbon monoxide in the presence of dicobalt octacarbonyl to form hexahydro-4,7-methano-indan-2 (or 3) carboxaldehyde; (22)-(29) describe chlorination of the polycyclic diphenols with chlorine or sulphuryl chloride. Specifications 621,102, 636,429, 648,513, 772,627, 777,215 and 1,009,020 are referred to.
GB35111/62A 1961-09-14 1962-09-14 Bisphenols and polyesters derived therefrom Expired GB1009019A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US13798061A 1961-09-14 1961-09-14

Publications (1)

Publication Number Publication Date
GB1009019A true GB1009019A (en) 1965-11-03

Family

ID=22479897

Family Applications (2)

Application Number Title Priority Date Filing Date
GB790/65A Expired GB1009020A (en) 1961-09-14 1962-09-14 Bischloroformates of diols
GB35111/62A Expired GB1009019A (en) 1961-09-14 1962-09-14 Bisphenols and polyesters derived therefrom

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB790/65A Expired GB1009020A (en) 1961-09-14 1962-09-14 Bischloroformates of diols

Country Status (3)

Country Link
DE (1) DE1300267B (en)
FR (1) FR1376466A (en)
GB (2) GB1009020A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2149051A5 (en) * 1971-04-27 1973-03-23 Naarden International Nv
WO2011136845A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Vinylbenzyl ethers of polycyclopentadiene polyphenol
WO2011136847A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Poly(allyl ether)s of polycyclopentadiene polyphenol
WO2011136843A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Epoxy polycyclopentadiene compounds
WO2011136846A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Polycyclopentadiene compounds with saturated cyclopentane ring
WO2011136844A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Polycyclopentadiene polyphenol and polycyanate polycyclopentadiene polyphenol compounds
WO2012044719A1 (en) * 2010-09-28 2012-04-05 Promerus Llc Norbornane-based pac ballast and positive-tone photosensitive resin composition encompassing the pac
US8329852B2 (en) 2008-11-28 2012-12-11 Bayer Materialscience Ag Copolycarbonates having improved surface hardness
TWI460154B (en) * 2011-09-28 2014-11-11 Promerus Llc Preparation of norbornane-based pac ballasts

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4310652A (en) * 1980-03-24 1982-01-12 Allied Chemical Corporation Melt processable poly(ester carbonate) with high glass transition temperature
EP2336245A1 (en) 2009-12-12 2011-06-22 Bayer MaterialScience AG Polycarbonate compounds with improved surface hardness
WO2018175965A1 (en) * 2017-03-24 2018-09-27 The Board Of Trustees Of The University Of Illinois Antiestrogens for cancer therapy

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2149051A5 (en) * 1971-04-27 1973-03-23 Naarden International Nv
US8329852B2 (en) 2008-11-28 2012-12-11 Bayer Materialscience Ag Copolycarbonates having improved surface hardness
CN102947261A (en) * 2010-04-29 2013-02-27 陶氏环球技术有限责任公司 Poly(allyl ether)s of polycyclopentadiene polyphenol
US8680217B2 (en) 2010-04-29 2014-03-25 Dow Global Technologies Llc Polycyclopentadiene compounds
WO2011136846A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Polycyclopentadiene compounds with saturated cyclopentane ring
WO2011136844A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Polycyclopentadiene polyphenol and polycyanate polycyclopentadiene polyphenol compounds
WO2011136843A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Epoxy polycyclopentadiene compounds
WO2011136847A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Poly(allyl ether)s of polycyclopentadiene polyphenol
WO2011136845A1 (en) * 2010-04-29 2011-11-03 Dow Global Technologies Llc Vinylbenzyl ethers of polycyclopentadiene polyphenol
CN103038205A (en) * 2010-04-29 2013-04-10 陶氏环球技术有限责任公司 Vinylbenzyl ethers of polycyclopentadiene polyphenol
US8519066B2 (en) 2010-04-29 2013-08-27 Dow Global Technologies Llc Poly(allyl ethers) of polycyclopentadiene polyphenol
US8609788B2 (en) 2010-04-29 2013-12-17 Dow Global Technologies Llc Polycyclopentadiene compounds
CN105175988A (en) * 2010-04-29 2015-12-23 陶氏环球技术有限责任公司 Polycyclopentadiene polyphenol and polycyanate polycyclopentadiene polyphenol compounds
US8664341B2 (en) 2010-04-29 2014-03-04 Dow Global Technologies, Llc Vinylbenzyl ethers of polycyclopentadiene polyphenol
WO2012044719A1 (en) * 2010-09-28 2012-04-05 Promerus Llc Norbornane-based pac ballast and positive-tone photosensitive resin composition encompassing the pac
JP2014500851A (en) * 2010-09-28 2014-01-16 プロメラス， エルエルシー Norbornane-based PAC ballast and positive photosensitive resin composition containing PAC
US9261781B2 (en) 2010-09-28 2016-02-16 Sumitomo Bakelite Co., Ltd. Preparation of norbornane-based PAC ballasts
TWI460154B (en) * 2011-09-28 2014-11-11 Promerus Llc Preparation of norbornane-based pac ballasts

Also Published As

Publication number Publication date
DE1300267B (en) 1969-07-31
GB1009020A (en) 1965-11-03
FR1376466A (en) 1964-10-31

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