GB798412A - Improvements in or relating to the modification and production of titanium ester compounds - Google Patents
Improvements in or relating to the modification and production of titanium ester compoundsInfo
- Publication number
- GB798412A GB798412A GB22991/54A GB2299154A GB798412A GB 798412 A GB798412 A GB 798412A GB 22991/54 A GB22991/54 A GB 22991/54A GB 2299154 A GB2299154 A GB 2299154A GB 798412 A GB798412 A GB 798412A
- Authority
- GB
- United Kingdom
- Prior art keywords
- titanate
- ester
- heating
- different
- titanium 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
Links
- 239000010936 titanium Substances 0.000 title abstract 15
- -1 titanium ester compounds Chemical class 0.000 title abstract 13
- 229910052719 titanium Inorganic materials 0.000 title abstract 10
- 230000004048 modification Effects 0.000 title 1
- 238000012986 modification Methods 0.000 title 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 abstract 10
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 8
- 238000010438 heat treatment Methods 0.000 abstract 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- 239000007787 solid Substances 0.000 abstract 6
- 235000010469 Glycine max Nutrition 0.000 abstract 5
- 239000000376 reactant Substances 0.000 abstract 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 4
- KQJBQMSCFSJABN-UHFFFAOYSA-N octadecan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-] KQJBQMSCFSJABN-UHFFFAOYSA-N 0.000 abstract 4
- 239000008096 xylene Substances 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 239000011521 glass Substances 0.000 abstract 3
- BFRLRGJQKQUFHK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;phthalic acid Chemical compound OCC(CO)(CO)CO.OC(=O)C1=CC=CC=C1C(O)=O BFRLRGJQKQUFHK-UHFFFAOYSA-N 0.000 abstract 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- BHJHPYFAYGAPLS-UHFFFAOYSA-N Guaicyl acetate Chemical compound COC1=CC=CC=C1OC(C)=O BHJHPYFAYGAPLS-UHFFFAOYSA-N 0.000 abstract 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 abstract 2
- 235000019864 coconut oil Nutrition 0.000 abstract 2
- 239000003240 coconut oil Substances 0.000 abstract 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 abstract 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 1
- 244000060011 Cocos nucifera Species 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- 229940007550 benzyl acetate Drugs 0.000 abstract 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 abstract 1
- 229940011051 isopropyl acetate Drugs 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 1
- 239000004926 polymethyl methacrylate Substances 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
A process for chemically modifying a tetra or mixed orthotitanate of the formula Ti(OR)4 or a polymeric titanate of the formula RO[-Ti(OR)2O-]xR, wherein R is an alkyl, aryl, aralkyl or cycloalkyl radical and x is an integer greater than 1, comprises transesterifying such a titanium ester with a carboxylic ester containing a radical in its alcohol-derived portion which is different from at least one organic radical of the titanium ester and containing no free hydroxyl groups to form a product titanium ester different from the reactant titanium ester and a coproduct carboxylic acid ester different from the reactant carboxylic acid ester. In a preferred embodiment a titanium ester of the formula Ti(OR)4, R being an alkyl, aryl, aralkyl or cycloalkyl radical containing at least 6 carbon atoms, for example tetra-octyl titanate, with a carboxylic acid ester of a polybasic alcohol, for example coconut oil, are mixed to form a stable intermediate solution which is heated to form a solid, tough body of glycerol, monoglyceride and diglyceride titanates plasticized by the octyl esters of the coconut acids. The heating may be effected by radiation or baking and temperatures of 50 DEG to 200 DEG C. are suitable. In examples: (1) butyl acetate and tetraisopropyl titanate are reacted and isopropyl acetate is distilled off to leave tetrabutyl titanate; (2) butyl acetate and tetraisopropyl titanate in different proportions are reacted to give diisopropyl dibutyl titanate; (3) reaction of guaiacol acetate and tetraisopropyl titanate give diguaiacol diisopropyl titanate; (4) phenyl benzoate and tetraisopropyl titanate are reacted to form tetraphenyl titanate; (5) a film of a mixture of coconut oil and tetraoctyl titanate is baked at 170 DEG C. on a glass slide to form a solid film; (6) a solid film is formed by heating to 120 DEG C. a xylene solution of a pentaerythritol phthalate resin completely esterified with soya bean acid and tetrastearyl titanate; (7) a xylene solution of an epichlorohydrinbis-phenol copolymer completely esterified with soy acids and tetrastearyl titanate is formed into a solid film by heating at 120 DEG C. on a glass slide, or into a gel by heating at 70 DEG C.; (8) hexaisopropyl dititanate (from the reaction of tetraisopropyl titanate with water) is reacted with benzyl acetate to form tetraisopropyl dibenzyl dititanate.ALSO:A process for chemically modifying a tetra or mixed orthotitanate of the formula Ti(OR)4 or a polymeric titanate of the formula RO[-Ti(OR)2O-]xR wherein R is an alkyl, aryl, aralkyl or cycloalkyl radical and x is an integer greater than 1, comprises transesterifying such a titanium ester with a carboxylic ester containing a radical in its alcohol-derived portion which is different from at least one organic radical of the titanium ester and containing no free hydroxyl groups to form a product titanium ester different from the reactant titanium ester and a co-product carboxylic acid ester different from the reactant carboxylic ester. Among the carboxylic acid esters specified as reactants are polyesters (e.g. glycerol or glycol/phthalic acid polyesters), polymethylmethacrylate, and fatty acid esters such as the soy acids ester of a copolymer of epichlorhydrin and p,p1-biphenol. In examples: (6) a solid film is formed by heating to 120 DEG C. a xylene solution of a pentaerythritol phthalate resin completely esterified with soy bean acid and tetrastearyl titanate; (7) a xylene solution of an epichlorohydrin-bis-phenol copolymer completely esterified with soy acids and tetrastearyl titanate is formed into a solid film by heating to 120 DEG C. on a glass slide, or into a gel by heating at 70 DEG C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US798412XA | 1953-08-07 | 1953-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB798412A true GB798412A (en) | 1958-07-23 |
Family
ID=22153130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22991/54A Expired GB798412A (en) | 1953-08-07 | 1954-08-06 | Improvements in or relating to the modification and production of titanium ester compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB798412A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003080705A1 (en) * | 2002-03-20 | 2003-10-02 | Cyclics Corporation | Catalytic systems |
| US6713601B2 (en) | 2000-09-12 | 2004-03-30 | Cyclics Corporation | Species modification in macrocyclic polyester oligomers, and compositions prepared thereby |
| US6787632B2 (en) | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
| US6831138B2 (en) | 2002-01-07 | 2004-12-14 | Cyclics Corporation | Polymer-containing organo-metal catalysts |
| US7666517B2 (en) | 2001-06-27 | 2010-02-23 | Cyclics Corporation | Isolation, formulation, and shaping of macrocyclic oligoesters |
| US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
| US7767781B2 (en) | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
-
1954
- 1954-08-06 GB GB22991/54A patent/GB798412A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
| US7767781B2 (en) | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
| US8283437B2 (en) | 2000-09-01 | 2012-10-09 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
| US6713601B2 (en) | 2000-09-12 | 2004-03-30 | Cyclics Corporation | Species modification in macrocyclic polyester oligomers, and compositions prepared thereby |
| US7666517B2 (en) | 2001-06-27 | 2010-02-23 | Cyclics Corporation | Isolation, formulation, and shaping of macrocyclic oligoesters |
| US6787632B2 (en) | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
| US6831138B2 (en) | 2002-01-07 | 2004-12-14 | Cyclics Corporation | Polymer-containing organo-metal catalysts |
| WO2003080705A1 (en) * | 2002-03-20 | 2003-10-02 | Cyclics Corporation | Catalytic systems |
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