GB956206A - Improvements in or relating to polyesters - Google Patents

Improvements in or relating to polyesters

Info

Publication number
GB956206A
GB956206A GB35113/62A GB3511362A GB956206A GB 956206 A GB956206 A GB 956206A GB 35113/62 A GB35113/62 A GB 35113/62A GB 3511362 A GB3511362 A GB 3511362A GB 956206 A GB956206 A GB 956206A
Authority
GB
United Kingdom
Prior art keywords
diphenol
cyclohexylmethylene
diphenyl
reacting
diol
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
GB35113/62A
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
Priority claimed from US137972A external-priority patent/US3220977A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB956206A publication Critical patent/GB956206A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/32—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/42—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/453—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing six-membered aromatic rings
    • 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
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
    • 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
    • C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
    • C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6826—Dicarboxylic acids and dihydroxy compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

4,41-(cyclohexylmethylene) diphenols are prepared by reacting butadiene or a substituted butadiene with an alpha, beta-unsaturated aldehyde, reducing the double bond in the product to obtain a saturated aldehyde which is then reacted with a phenol. The reactions may be represented as follows: <FORM:0956206/C2/1> <FORM:0956206/C2/2> <FORM:0956206/C2/3> <FORM:0956206/C2/4> where R, R1, R2 and R3 are hydrogen or chlorine atoms or alkyl groups having up to four carbon atoms, and R2 also may be a phenyl group. Alternatively the saturated aldehyde above may be obtained by carrying out an oxo reaction on cyclohexene or a substituted cyclohexene as follows: <FORM:0956206/C2/5> In examples, cyclohexanecarboxaldehyde is obtained from cyclohexene, or by reacting butadiene and acrolein followed by hydrogenation, and is reacted with phenol to give 4,41-(cyclohexylmethylene)diphenol; 1-methyl-3-cyclohexene -1- carboxaldehyde is obtained by reacting butadiene and methacrolein followed by hydrogenation, and is reacted with phenol to give 4, 41-(1-methylcyclohexylmethylene) diphenol; 4,41-(2-methylcyclohexylmethylene) diphenol and 4, 41-(2-phenylcyclohexylmethylene) diphenol are prepared similarly; and 4, 41-(cyclohexylmethylene) bis (2, 6-dichlorophenol) is prepared by reacting 4, 41-(cyclohexylmethylene) diphenol with clorine.ALSO:The invention comprises polyesters derived from dicarboxylic acids or carbonic acid and diols in which at least 10% of the diol units have the formula: <FORM:0956206/C3/1> where R, R1, R2 and R3 are hydrogen or chlorine atoms or alkyl groups containing up to four carbon atoms and R2 also may be a phenyl group. The polymers are prepared (a) by ester interchange of the diol with a phenyl or cresyl ester of a dicarboxylic acid, (b) by reacting the diol with a dicarboxylic acid chloride, (c) by reacting an acid ester of the diol with a dicarboxylic acid, or (d) by adding phosgene and/or a bischloroformate of a diol to a cooled aqueous mixture containing sodium hydroxide, the diphenoyl, a catalyst and methylene chloride. In examples the starting materials used to obtain polymers are 4, 41-(cyclohexyl-methylene) diphenol, 4, 41-(1-methylcyclo-hexylmethylene) diphenol, 4, 41-(2-methylcyclohexylmethylene) diphenol, 4, 41-(2-phenyl cyclohexylmethylene) diphenol, 4, 41-(cyclohexylmethylene) bis-(2, 6-dichlorophenol), diphenyl terephthalate, diphenyl trans-cyclohexane-1, 4-dicarboxylate, diphenyl dimethylmalonate, diphenyl isophthalate, diphenyl sebacate and diphenyl azelate.
GB35113/62A 1961-09-14 1962-09-14 Improvements in or relating to polyesters Expired GB956206A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US137972A US3220977A (en) 1961-09-14 1961-09-14 Linear polyesters from 4,4'-(cyclohexylmethylene)diphenols
FR909487A FR1333560A (en) 1961-09-14 1962-09-14 New linear polyesters of bis-phenols

Publications (1)

Publication Number Publication Date
GB956206A true GB956206A (en) 1964-04-22

Family

ID=26197535

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35113/62A Expired GB956206A (en) 1961-09-14 1962-09-14 Improvements in or relating to polyesters

Country Status (2)

Country Link
FR (1) FR1333560A (en)
GB (1) GB956206A (en)

Also Published As

Publication number Publication date
FR1333560A (en) 1963-07-26

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