GB877134A - Improvements in or relating to polyethers - Google Patents

Improvements in or relating to polyethers

Info

Publication number
GB877134A
GB877134A GB43001/59A GB4300159A GB877134A GB 877134 A GB877134 A GB 877134A GB 43001/59 A GB43001/59 A GB 43001/59A GB 4300159 A GB4300159 A GB 4300159A GB 877134 A GB877134 A GB 877134A
Authority
GB
United Kingdom
Prior art keywords
polymerized
epoxy
epoxidized
acid
alcohol
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
GB43001/59A
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.)
JBS USA LLC
Original Assignee
Swift and Co Inc
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 US607256A external-priority patent/US2964454A/en
Priority claimed from US625250A external-priority patent/US2964484A/en
Priority claimed from US651161A external-priority patent/US3042692A/en
Priority claimed from US651822A external-priority patent/US3035069A/en
Application filed by Swift and Co Inc filed Critical Swift and Co Inc
Publication of GB877134A publication Critical patent/GB877134A/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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • 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
    • C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
    • C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/28—Treatment by wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Abstract

Polyethers are derived by opening the epoxy ring or rings in an alcohol, acid, ester, amide, nitrile or acid halide having at least one C10-C22 chain with the grouping <FORM:0877134/IV (a)/1> wherein m is a whole number from 0-15, p a whole number from 1-15, x is 1, 2 or 3 and m+ 3x+p+1=10-22. Rupture of the rings is effected with a Lewis acid catalyst, examples of which are boron trifluoride, zinc chloride, aluminium chloride, stannic chloride, silicon tetrachloride, and perchloric acid. The catalyst may be used as a complex with water, an alcohol or an ether and the catalyst or complex may be used in the presence of (e.g. as a solution in) water, an alcohol or an ether. The epoxy starting materials are preferably based on naturally occurring unsaturated fatty acids. Polymerized acids or esters may be treated to form salts, e.g. sodium, potassium or ammonium salts. In all the examples BF3-etherate was employed as catalyst. (1), 9, 10-epoxystearic acid was polymerized. The product may be purified by saponification followed by urea adduct refining; (2) methyl-9, 10-epoxy stearate was polymerized, and purified by urea adduct formation, liquid-liquid extraction, propane refining or vacuum distillation. Hydrolysed it yields a pure form of the acid obtained in Example (1); (3) Partially epoxidized menhaden or soya bean oil (1,36% oxirane oxygen) was polymerized. The products were air-drying oils; (5) 9, 10-epoxy oleyl acetate was polymerized in presence of methyl "Cellosolve" (Registered Trade Mark). Hydrolysed with alcoholic NaOH, it yielded the polyether alcohol; (6) 9, 10-epoxystearamide was polymerized; (7) 9, 10-epoxy stearyl nitrile was polymerized; (8) 9, 10-epoxystearyl chloride was polymerized. (4) Other epoxides which were polymerized were butyl epoxystearate, hexyl epoxystearate, tetrahydrofurfuryl epoxystearate, methyl esters of epoxidized soya bean oil fatty acids, epoxidized distilled acetylated monoglyceride of soybean oil or lard oil, methyl Cellosolve, 2-ethyl hexyl, butyl or iso-propyl esters of epoxidized soybean oil fatty acids. These "linear" polymers are suitable as lubricant additives. Their salts are water-soluble and surface-active. Using poly-epoxide starting materials, cross-linked polymers may be obtained. They are useful for casting or moulding or as additives to natural or synthetic rubber. In Example (9) epoxidized soybean oil (6,2% epoxy oxygen) was polymerized in presence of methyl Cellosolve; (10) epoxidized lard oil (3,98% epoxy oxygen) was similarly polymerized; (11) epoxidized linseed oil (8,2% epoxy oxygen) was polymerized in presence of tetraethylene glycol; (12) dipentaerythritol hexa (epoxy) stearate was polymerized in presence of methyl Cellosolve; (13) The product of Example (9) was saponified with alcoholic KOH and acidified to yield the polyether polymer of epoxy stearic acid. Soluble poly soaps of other polymerized epoxidized oils may be similarly prepared. Soluble products may be prepared from polyepoxides by moderating catalyst activity with water or alcohol. Glycol esters of epoxy fatty acids are specifically mentioned as suitable starting materials. Specifications 737,697 and 877,135 also are referred to. Reference has been directed by the Comptroller to Specification 783,740.
GB43001/59A 1956-08-31 1957-08-29 Improvements in or relating to polyethers Expired GB877134A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US607256A US2964454A (en) 1956-08-31 1956-08-31 Improvements in irradiation polymerization
US625250A US2964484A (en) 1956-11-30 1956-11-30 Cross-linked reaction product of an epoxidized fatty acid ester and polyvinyl halide or cellulose nitrate
US651161A US3042692A (en) 1956-11-30 1957-04-08 Epoxy ether polyamides
US877134XA 1957-04-10 1957-04-10
US651822A US3035069A (en) 1956-11-30 1957-04-10 Treatment of epoxy fatty compositions

Publications (1)

Publication Number Publication Date
GB877134A true GB877134A (en) 1961-09-13

Family

ID=62527879

Family Applications (3)

Application Number Title Priority Date Filing Date
GB43003/59A Expired GB877136A (en) 1956-08-31 1957-08-29 Improvements in or relating to polyesters
GB27294/57A Expired GB861971A (en) 1956-08-31 1957-08-29 Improvements in or relating to polyepoxide-thermoplastic polymer compositions
GB43001/59A Expired GB877134A (en) 1956-08-31 1957-08-29 Improvements in or relating to polyethers

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB43003/59A Expired GB877136A (en) 1956-08-31 1957-08-29 Improvements in or relating to polyesters
GB27294/57A Expired GB861971A (en) 1956-08-31 1957-08-29 Improvements in or relating to polyepoxide-thermoplastic polymer compositions

Country Status (1)

Country Link
GB (3) GB877136A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3280153A (en) * 1961-10-11 1966-10-18 Ciba Ltd Esters containing both epoxide and oxetane groups, their production and their uses
WO2006002812A1 (en) * 2004-07-01 2006-01-12 Cognis Ip Management Gmbh Viscosity reducer for highly viscous polyols
US7786239B2 (en) 2004-06-25 2010-08-31 Pittsburg State University Modified vegetable oil-based polyols
CN104497295A (en) * 2014-12-16 2015-04-08 中国林业科学研究院林产化学工业研究所 Vegetable-fat anionic polymer surfactant and preparation method thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0826122B2 (en) * 1992-04-02 1996-03-13 ピーピージー インダストリーズ，インコーポレイテッド Epoxide-phosphorus containing acid-cyclic anhydride reaction products and their use in coating compositions
EP1425330B1 (en) * 2001-09-12 2005-03-09 Dow Global Technologies Inc. Network polymers comprising epoxy-terminated esters

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3280153A (en) * 1961-10-11 1966-10-18 Ciba Ltd Esters containing both epoxide and oxetane groups, their production and their uses
US7786239B2 (en) 2004-06-25 2010-08-31 Pittsburg State University Modified vegetable oil-based polyols
US8153746B2 (en) 2004-06-25 2012-04-10 Cargill, Incorporated Modified vegetable oil-based polyols
WO2006002812A1 (en) * 2004-07-01 2006-01-12 Cognis Ip Management Gmbh Viscosity reducer for highly viscous polyols
US8153750B2 (en) 2004-07-01 2012-04-10 Cognis Ip Management Gmbh Viscosity reducer for highly viscous polyols
CN104497295A (en) * 2014-12-16 2015-04-08 中国林业科学研究院林产化学工业研究所 Vegetable-fat anionic polymer surfactant and preparation method thereof

Also Published As

Publication number Publication date
GB861971A (en) 1961-03-01
GB877136A (en) 1961-09-13

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