GB998479A - Improvements in or relating to the copolymerisation of trioxan - Google Patents

Improvements in or relating to the copolymerisation of trioxan

Info

Publication number
GB998479A
GB998479A GB2418460A GB2418460A GB998479A GB 998479 A GB998479 A GB 998479A GB 2418460 A GB2418460 A GB 2418460A GB 2418460 A GB2418460 A GB 2418460A GB 998479 A GB998479 A GB 998479A
Authority
GB
United Kingdom
Prior art keywords
cyclic
ester
compound
reaction
trioxane
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
GB2418460A
Inventor
Walter Wilson
Herbert May
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.)
British Industrial Plastics Ltd
Original Assignee
British Industrial Plastics Ltd
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 British Industrial Plastics Ltd filed Critical British Industrial Plastics Ltd
Publication of GB998479A publication Critical patent/GB998479A/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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/06—Catalysts
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/10—Polymerisation of cyclic oligomers of formaldehyde
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/18—Copolymerisation of aldehydes or ketones
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/18—Copolymerisation of aldehydes or ketones
    • C08G2/20—Copolymerisation of aldehydes or ketones with other aldehydes or ketones
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/18—Copolymerisation of aldehydes or ketones
    • C08G2/26—Copolymerisation of aldehydes or ketones with compounds containing carbon-to-carbon 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/28—Post-polymerisation treatments
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/30—Chemical modification by after-treatment

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Copolymers are prepared by reacting trioxane under substantially anhydrous conditions in the presence of an electrophilic catalyst with (a) a cyclic carboxylic ester A which is not an alkylene carbonate or a 5- or more membered ring simple lactone or (b) a cyclic carboxylic ester B and at least one other compound C capable of copolymerizing with trioxane in the presence of the catalyst. More than one cyclic ester may be used. The cyclic ester A may be b -propiolactone, specified substitution derivatives thereof, trichloroethylidene lactate, methylene glycollate, lactide, ethylene oxalate, or dioxanone. The cyclic ester B may be as A or a d -lactone (d -valerolactone, b -methyl-d -valerolactone) or e -caprolactone. The compound C may be a cyclic ether (e.g. as in Specification 903,668), an aldehyde (e.g. acetaldehyde or chloral), a styrene, 1- or 2-vinylnaphthalene, stilbene, indene, coumarone, acenaphthylene, a vinyl compound (such as a vinyl ether, N-vinyl-carbazole, or 2-vinylpyridine), isobutene, butadiene, cyclohexene, b -pinene, an allyl ether or ester, an aliphatic or aromatic isocyanate, or a saturated or unsaturated nitrile. The catalyst may be BF3, SnCl4, or FeCl3 or a complex thereof, dihydroxyfluoroboric acid, polyphosphoric acid, the complex of BF3 with phosphoric acid or polyphosphoric acid, a complex of BF3 with a very weakly basic nitrogen compound, a halogen or interhalogen compound, or an oxonium salt. The reaction may be effected at 0-100 DEG C. in an inert liquid medium under nitrogen. Fresh reactants may be added as the reaction proceeds. The cyclic ester or other reactant may be partially polymerized before reaction with trioxane. Other compounds may be partially polymerized or partially reacted with trioxane or the cyclic ester prior to the introduction of the other reactant or reactants. At the end of the reaction, an organic solvent or an aqueous solution of a complexing agent is added. The products may be stabilized by reaction with an acid anhydride or an isocyanate or by incorporation therein of an antioxidant and/or an ultra-violet light-absorbing substance, e.g. N-phenyl-1-naphthylamine or 2-hydroxy-4-methoxy-benzophenone amongst others.
GB2418460A 1960-07-11 1960-07-11 Improvements in or relating to the copolymerisation of trioxan Expired GB998479A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3185160 1960-07-11

Publications (1)

Publication Number Publication Date
GB998479A true GB998479A (en) 1965-07-14

Family

ID=10329347

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2418460A Expired GB998479A (en) 1960-07-11 1960-07-11 Improvements in or relating to the copolymerisation of trioxan

Country Status (5)

Country Link
BE (1) BE606009A (en)
CH (1) CH420627A (en)
DE (1) DE1250124B (en)
GB (1) GB998479A (en)
NL (1) NL266913A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4190720A (en) * 1978-12-26 1980-02-26 Ethicon, Inc. Isomorphic copolymers of ε-caprolactone and 1,5-dioxepan-2-one

Also Published As

Publication number Publication date
CH420627A (en) 1966-09-15
NL266913A (en)
DE1250124B (en) 1967-09-14
BE606009A (en)

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