ES272034A1 - New polyaddition resins - Google Patents
New polyaddition resinsInfo
- Publication number
- ES272034A1 ES272034A1 ES0272034A ES272034A ES272034A1 ES 272034 A1 ES272034 A1 ES 272034A1 ES 0272034 A ES0272034 A ES 0272034A ES 272034 A ES272034 A ES 272034A ES 272034 A1 ES272034 A1 ES 272034A1
- Authority
- ES
- Spain
- Prior art keywords
- pyran
- dihydro
- methyl
- bis
- ester
- 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
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- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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- 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
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- C08G63/66—Polyesters containing oxygen in the form of ether groups
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
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- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
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- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
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- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
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- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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Abstract
In examples: (16( adipic acid-bis-(2,3-dihydro-4H-pyran-2-yl-methyl ester is prepared from the corresponding alcohol and adipic acid dichloride. (18) Bis-(2,3-dihydro-4H-pyran-2-yl) formal is prepared from divinyl formal and acrolein (19) Ethylene glycol-bis-(2,3-dihydro-4H-pyran-2-yl) ether is prepared from ethylene glycol divinyl ether and acrolein (22) Oxalic acid - bis - (2,3 - dihydro - 4H - pyran - 2 - yl-methyl) ester is prepared from oxalalyl chloride and the corresponding methanol derivation (23) and (24) The succinic acid di-ester and the tri-phosphate are similarly prepared (25) Bis - (2,3 - dihydro - 4H - pyran - 2 - yl - methyl) carbonate is prepared from phosgene and the appropriate methanol derivative (28) Toluene-2,4 - bis - (carbamic acid - 21,31 - dihydro - 41H-pyran-21-yl-methyl ester) is prepared from toluene-2,4-diisocyanate and 2,3-dihydro-4H-pyran-2-yl-methanol (29) Ethylene diamine-bis-(2,3-dihydro - 4H - pyran - 2 - methyl - 2 - carboxylic acid) amide is prepared from ethylene diamine and 2,3 - dihydro - 4H - pyran - 2 8 methyl - 2-carboxylic acid methyl ester (30) and (31) Ethylene glycol - bis - (2,3 - dihydro - 4H - pyran-2-methyl-2-carboxylic acid) ester is prepared from ethylene glycol and 2,3-dihydro-4H-pyran-2-methyl-2-carboxyli acid methyl ester, and Hexanetriol - bis - (2,3 - dihydro - 4H - pyran-2-methyl-2-carboxylic acid) ester and pentaery-thritol - bis - (2,3 - dihydro - 4H - pyran - 2 - methyl-2-carboxylic acid) ester are prepared from hexanetriol or pentaerythritol and the same methyl ester.ALSO:Polyaddition resins are prepared by reacting (1) a compound of the general formula <FORM:0996705/C3/1> in which R is H or CH3 n=2 to 6 and Z is either -COOCH2- (in which case n=2) or -[-COO-]-nY, where Y is the hydrocarbon residue of a polyol or -[-CH2O-]-nX, where X is the ester residue of a polycarboxylic or inorganic acid of basicity n, or an alkylidene group (in which case n=2), or the hydrocarbon residue of a polyol or -[-O-]-nR1, where R1 is the hydrocarbon residue of a polyol or an alkylidene group (in which case n=2) or -[-OCONH-]-nR2, or -[-CH2OCONH-]-nR2, where R2 is a hydrocarbon radical of valency n, with (2) a compound containing at least two groups chosen from hydroxyl, mercapto, carboxyl, amide, acetal and ortho-ester groups. Preferably, an acid catalyst is used, unless compound (2) above is strongly acidic. Suitable starting materials are listed. If desired, a precondensate may first be formed, and cured by further reaction, e.g. with polyols, polyesters, phenolic or epoxy resins. Products may be linear or cross-linked. Conventional additives, e.g. fillers, plasticizers or colouring matters may be added before curing. In Examples 1-15, 20, 21, compound (1) is 2,3-dihydro - 4H - pyran - 2 - carboxylic acid-(21,31-dihydro - 41H - pyran - 21 - yl) - methyl ester. It is reacted with: Example 1. Ethylene glycol. 2. Glycerol. 3. A polyester from glycerol and phthalic anhydride. 4. Oxalic acid. 5. A polyester from adipic acid and glycol. 6. A hexanetriol-phthalate resin. 7. A mixture of 1,2,6-hexanetriol and phenol. 8. A mixture of trimethylolpropane and 1,1 - bis - (41 - hydroxyphenyl) ethane. 9. A hydroxylated ester from ethylene glycol, trimethylol ethane, and succinic anhydride. 10. A mixture of 1,4-bis-(hydroxymethyl) - benzene, phenol and diglycerol. 11. A mixture of glyoxal-tetramethylacetal and trimethylolpropane. 12. A mixture of a hydroxylated ester from ethylene glycol, trimethylol ethane, and succinic anhydride, with a liquid polymeric polysulphide known as "Thiokol LP-3" (Registered Trade Mark). 13. A mixture of thiourea and glycerol. 14. A mixture of trimethylolpropane and e -caprolactam. 15. A mixture of trimethylolpropane and an epoxy resin from 2,2-bis-(p-hydroxyphenyl)-propane and epichlorhydrin. 20. A mixture of trimethylol propane and e -caprolactone. 21. Polyvinyl alcohol. The other examples are as follows: 16. Adipic acid-bis-(2,3-dihydro-4H -pyran-2-yl-methyl ester) is reacted with e -caprolactone and trimethylolpropane. 17. Excess 2,3 - dihydro - 4H - pyran - 2 - carboxylic acid - (21,31 - hydro - 41H - pyran - 21 - yl) methyl ester is reacted with ethylene glycol-di-(2 -hydroxypropyl) ether. The product may be subsequently reacted with the hydroxylated ester of Example 9. 18. Bis-(2,3-dihydro-4H -pyran-2-yl)-formal is reacted with the hydroxylated ester of Example 9. 19. Ethylene glycolbis - (2,3 - dihydro - 4H - pyran - 2 - yl) ether is reacted with a mixture of phenol and 1,2,6-hexanetriol. 22. Oxalic acid bis-(2,3-dihydro - 4H - pyran - 2 - yl - methyl) ester is reacted with (a) 1,2,6-hexanetriol, or (b) trimethylolpropane. Other examples use succinic acid-bis -(2,3 - dihydro - 4H - pyran - 2 - yl - methyl) ester tri - (2,3 - dihydro - 4H - pyran - 2 - yl - methyl) phosphate bis - (2,3 - dihydro - 4H - pyran - 2 - yl - methyl) carbonate diphenyl-di -(2,3 - dihydro - 4H - pyran - 2 - yl - methyl) orthosilicate (prepared from 2,3-dihydro-4H -pyran-2-yl-methanol and diphenoxy dichlorosilane a urethane prepared from an adduct of hexanetriol and m-phenylene diisocyanate, and 2,3 - dihydro - 4H - pyran - 2 - yl - methanol toluene - 2,4 - bis - (carbamic acid - 21,31 - di - hydro - 41H - pyran - 21 - yl - methyl ester) Ethylene diamine - bis - (2,3 - dihydro - 4H - pyran - 2 - methyl - 2 - carboxylic acid)-amide ethylene glycol - bis - (2,3 - dihydro - 4H-pyran -2 - methyl - 2 - carboxylic acid) ester hexane triol - bis - (2,3 - dihydro - 4H - pyran - 2 - methyl - 2 - carboxylic acid) ester and pentaerythritol - bis - (2,3 - dihydro - 4H - pyran - 2 - methyl - 2 - carboxylic acid) ester.ALSO:In Example 3, a glycerol-phthalic anhydride resin is dissolved in isobutyl acetate and 213-dihydro-4H-pyran-2-carboxylic acid-[2131-dihydro-41H-pyran-21-yl] -methyl ester and hydrochloric acid is added. The solution is distributed over an aluminium sheet, solvent evaporated and the lacquer coat stoved.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CH1281960A CH428234A (en) | 1960-11-16 | 1960-11-16 | Curable mixtures |
Publications (1)
Publication Number | Publication Date |
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ES272034A1 true ES272034A1 (en) | 1962-04-16 |
Family
ID=4386656
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ES0272034A Expired ES272034A1 (en) | 1960-11-16 | 1961-11-15 | New polyaddition resins |
Country Status (6)
Country | Link |
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BE (1) | BE610417A (en) |
CH (1) | CH428234A (en) |
DE (1) | DE1445315B2 (en) |
ES (1) | ES272034A1 (en) |
GB (1) | GB996705A (en) |
NL (2) | NL134014C (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1101343A (en) * | 1963-12-30 | 1968-01-31 | Ici Ltd | Isocyanate-containing vinyl ether foams |
US3429853A (en) * | 1964-07-24 | 1969-02-25 | Shell Oil Co | Process for preparing prepolymers of unsaturated heterocyclic compounds and resulting products |
US4221779A (en) * | 1977-06-28 | 1980-09-09 | Graham Neil B | Pharmaceutical composition for treating tropical diseases |
EP0475107B1 (en) * | 1990-08-30 | 1995-02-15 | Th. Goldschmidt AG | Use of 2-(2'-propenyl)-3,4-dihydro-2H-pyranes |
DE4042353C2 (en) * | 1990-08-30 | 1995-04-06 | Goldschmidt Ag Th | Use of 2- (2'-propenyl) -3,4-dihydro-2H-pyrans |
-
0
- BE BE610417D patent/BE610417A/xx unknown
- NL NL271416D patent/NL271416A/xx unknown
- NL NL134014D patent/NL134014C/xx active
-
1960
- 1960-11-16 CH CH1281960A patent/CH428234A/en unknown
-
1961
- 1961-11-14 GB GB40751/61A patent/GB996705A/en not_active Expired
- 1961-11-15 DE DE19611445315 patent/DE1445315B2/en active Pending
- 1961-11-15 ES ES0272034A patent/ES272034A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH428234A (en) | 1967-01-15 |
DE1445315B2 (en) | 1972-04-13 |
BE610417A (en) | 1900-01-01 |
DE1445315A1 (en) | 1968-12-19 |
GB996705A (en) | 1965-06-30 |
NL134014C (en) | 1900-01-01 |
NL271416A (en) | 1900-01-01 |
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