GB859645A - Process for preparing lactone adducts and polyesters - Google Patents
Process for preparing lactone adducts and polyestersInfo
- Publication number
- GB859645A GB859645A GB12165/57A GB1216557A GB859645A GB 859645 A GB859645 A GB 859645A GB 12165/57 A GB12165/57 A GB 12165/57A GB 1216557 A GB1216557 A GB 1216557A GB 859645 A GB859645 A GB 859645A
- Authority
- GB
- United Kingdom
- Prior art keywords
- caprolactone
- epsilon
- formula
- lactone
- carbon
- 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
Links
- 150000002596 lactones Chemical class 0.000 title abstract 6
- 229920000728 polyester Polymers 0.000 title abstract 6
- 238000004519 manufacturing process Methods 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 6
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 abstract 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 4
- -1 aromatic hydrocarbon radicals Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 abstract 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 abstract 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 abstract 2
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 abstract 2
- NYXHXTYKMBMJSL-UHFFFAOYSA-N O(O)O.[C] Chemical compound O(O)O.[C] NYXHXTYKMBMJSL-UHFFFAOYSA-N 0.000 abstract 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 235000010233 benzoic acid Nutrition 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000002894 organic compounds Chemical class 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 2
- XXCRXPYEAMCJKH-UHFFFAOYSA-N 3,3,4-trimethyloxepan-2-one Chemical compound CC1CCCOC(=O)C1(C)C XXCRXPYEAMCJKH-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 abstract 1
- 229950006800 prenderol Drugs 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
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
- 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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
-
- 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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US577949A US2977385A (en) | 1956-04-13 | 1956-04-13 | Process for producing lactone adducts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB859645A true GB859645A (en) | 1961-01-25 |
Family
ID=24310805
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12165/57A Expired GB859645A (en) | 1956-04-13 | 1957-04-15 | Process for preparing lactone adducts and polyesters |
| GB19367/60A Expired GB867111A (en) | 1956-04-13 | 1957-04-15 | Acylated lactone adducts and polyesters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19367/60A Expired GB867111A (en) | 1956-04-13 | 1957-04-15 | Acylated lactone adducts and polyesters |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2977385A (en, 2012) |
| BE (1) | BE556562A (en, 2012) |
| DE (2) | DE1270288B (en, 2012) |
| FR (1) | FR1174207A (en, 2012) |
| GB (2) | GB859645A (en, 2012) |
| IT (1) | IT570045A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0752438A1 (en) * | 1995-07-06 | 1997-01-08 | Chevron Chemical Company | Polyalkylene polylactone aminocarbamates and fuel compositions containing the same |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3140267A (en) * | 1960-05-04 | 1964-07-07 | Celanese Corp | Alkyd resins modified with omega lactone |
| US3882088A (en) * | 1968-11-18 | 1975-05-06 | Du Pont | Polyesters bearing polyethylenimine terminal groups |
| US3642507A (en) * | 1969-04-01 | 1972-02-15 | Union Carbide Corp | Compositions of nitrocellulose and cyclic ester polymers |
| GB1425563A (en) * | 1972-02-08 | 1976-02-18 | Laporte Industries Ltd | Rigid polyurethanes |
| GB1453794A (en) * | 1974-01-11 | 1976-10-27 | Interox Chemicals Ltd | Polyurethane foams |
| US4130532A (en) * | 1974-08-21 | 1978-12-19 | Ciba-Geigy Ag | Polyester plasticizers |
| GB1455390A (en) * | 1974-08-22 | 1976-11-10 | Ciba Geigy Ag | Polyesters self-cooling wheel |
| CA1064185A (en) * | 1975-05-22 | 1979-10-09 | Parameswar Sivaramakrishnan | Modified aromatic polycarbonates |
| US4096125A (en) * | 1976-05-26 | 1978-06-20 | Union Carbide Corporation | Polycaprolactone derivatives and coating compositions thereof |
| US4430131A (en) | 1979-11-08 | 1984-02-07 | Her Majesty The Queen In Right Of Canada | Polyurethane binders |
| US4415728A (en) * | 1979-11-08 | 1983-11-15 | Her Majesty The Queen In Right Of Canada | ε-Caprolactone co-polyesters useful for the preparation of polyurethane |
| US4284506A (en) * | 1979-12-26 | 1981-08-18 | Nl Industries, Inc. | Biomedical devices |
| US4605724A (en) * | 1984-10-01 | 1986-08-12 | Ppg Industries, Inc. | High solids lactone-polyester polyols and coating compositions thereof |
| JP2844474B2 (ja) * | 1989-07-19 | 1999-01-06 | ダイセル化学工業株式会社 | ポリウレタンの製造方法 |
| US5159047A (en) * | 1991-06-14 | 1992-10-27 | E. I. Du Pont De Nemours And Company | Coatings containing caprolactone oligomer polyols |
| CA2178671A1 (en) * | 1995-07-06 | 1997-01-07 | Richard E. Cherpeck | Polylactone aromatic esters and fuel compositions containing the same |
| CA2178663A1 (en) * | 1995-07-06 | 1997-01-07 | Richard E. Cherpeck | Polylactone aminocarbamates and fuel compositions containing the same |
| WO2005059003A1 (en) * | 2003-12-15 | 2005-06-30 | The Children's Hospital Of Philadelphia | Novel polyesters |
| FR2912751B1 (fr) * | 2007-02-16 | 2012-07-13 | Arkema France | Procede de preparation de polylactones et polylactames |
| FR2912752B1 (fr) * | 2007-02-16 | 2012-10-05 | Arkema France | Procede de preparation d'un copolymere d'au moins un monomere cyclique |
| EP2726564A2 (en) | 2011-06-30 | 2014-05-07 | OCE-Technologies B.V. | Hot melt ink composition comprising a copolyester and process for preparing a copolyester |
| US10808084B2 (en) * | 2016-09-23 | 2020-10-20 | Regents Of The University Of Minnesota | Methods for making renewable and chemically recyclable crosslinked polyester elastomers |
| CN111468032B (zh) * | 2020-05-28 | 2021-03-26 | 江南大学 | 一种易溶解/可裂解/自增稠表面活性剂和制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1927295A (en) * | 1929-07-24 | 1933-09-19 | Edward J Powers | Process for producing acylated esters of hydroxy-acids |
| US2120756A (en) * | 1937-01-09 | 1938-06-14 | Monsanto Chemicals | Methyl ester compositions |
| US2260295A (en) * | 1938-08-24 | 1941-10-28 | Carbide & Carbon Chem Corp | Plasticizer and plastic composition |
| DE869867C (de) * | 1942-07-22 | 1953-03-09 | Hydrierwerke A G Deutsche | Verfahren zur Herstellung von Polykondensationsprodukten |
| US2399286A (en) * | 1942-11-25 | 1946-04-30 | Pittsburgh Plate Glass Co | Unsaturated esters and polymers thereof |
| FR956245A (en, 2012) * | 1942-12-24 | 1950-01-27 | ||
| DE878857C (de) * | 1943-06-26 | 1953-06-08 | Basf Ag | Verfahren zur Herstellung von Kondensationsprodukten |
| US2449990A (en) * | 1945-10-05 | 1948-09-28 | Goodrich Co B F | Beta-acyloxy carboxylic acid compounds and methods of preparing the same |
| US2526554A (en) * | 1947-07-28 | 1950-10-17 | Goodrich Co B F | Preparation of beta-hydroxy carboxylic acid esters by alcoholysis of linear polyesters derived from beta-lactones |
| US2458421A (en) * | 1947-11-22 | 1949-01-04 | Eastman Kodak Co | Unsaturated derivatives of ethylene diamine and polymers thereof |
| US2458422A (en) * | 1947-11-22 | 1949-01-04 | Eastman Kodak Co | Acrylic diester-propionamides and polymers thereof |
| US2578684A (en) * | 1948-06-18 | 1951-12-18 | Edward M Filachione | Glycol esters of acyloxycarboxylic acids |
| US2573701A (en) * | 1948-06-18 | 1951-11-06 | Edward M Filachione | Polyethylene glycol esters of acyloxycarboxylic acids |
| US2559510A (en) * | 1949-04-21 | 1951-07-03 | Standard Oil Dev Co | Synthetic lubricants |
| US2676941A (en) * | 1950-11-10 | 1954-04-27 | Us Agriculture | Vinyl chloride polymers plasticized with alkyl carbonates of glycol lactates |
| US2712025A (en) * | 1951-09-26 | 1955-06-28 | Chessie E Rehberg | Production of dicarboxylic acid esters of alpha-hydroxycarboxylic acid esters |
| DE975191C (de) * | 1951-12-02 | 1961-09-21 | Johannes Kleine Dr Ing | Verfahren zur Herstellung von Polyestern aus 6-gliedrigen cyclischen Estern |
| DE936746C (de) * | 1953-05-01 | 1955-12-22 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Lactylmilchsaeureamiden |
-
0
- BE BE556562D patent/BE556562A/xx unknown
- IT IT570045D patent/IT570045A/it unknown
-
1956
- 1956-04-13 US US577949A patent/US2977385A/en not_active Expired - Lifetime
-
1957
- 1957-04-12 DE DEP1270A patent/DE1270288B/de active Pending
- 1957-04-12 DE DE19571668811 patent/DE1668811A1/de active Pending
- 1957-04-12 FR FR1174207D patent/FR1174207A/fr not_active Expired
- 1957-04-15 GB GB12165/57A patent/GB859645A/en not_active Expired
- 1957-04-15 GB GB19367/60A patent/GB867111A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0752438A1 (en) * | 1995-07-06 | 1997-01-08 | Chevron Chemical Company | Polyalkylene polylactone aminocarbamates and fuel compositions containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| GB867111A (en) | 1961-05-03 |
| DE1668811A1 (de) | 1972-11-09 |
| DE1270288B (de) | 1968-06-12 |
| FR1174207A (fr) | 1959-03-09 |
| US2977385A (en) | 1961-03-28 |
| BE556562A (en, 2012) | |
| IT570045A (en, 2012) |
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