GB734114A - Process of producing reaction products of titanic acid esters with high molecular weight compounds containing hydroxyl groups - Google Patents
Process of producing reaction products of titanic acid esters with high molecular weight compounds containing hydroxyl groupsInfo
- Publication number
- GB734114A GB734114A GB17656/51A GB1765651A GB734114A GB 734114 A GB734114 A GB 734114A GB 17656/51 A GB17656/51 A GB 17656/51A GB 1765651 A GB1765651 A GB 1765651A GB 734114 A GB734114 A GB 734114A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ester
- titanic acid
- complex
- molecular weight
- insoluble
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title abstract 5
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical class O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 title abstract 5
- 150000002605 large molecules Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 239000007795 chemical reaction product Substances 0.000 title abstract 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 10
- 150000002148 esters Chemical class 0.000 abstract 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 9
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 8
- -1 titanic acid ester Chemical class 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 4
- 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 4
- 150000004820 halides Chemical class 0.000 abstract 4
- 239000003960 organic solvent Substances 0.000 abstract 4
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 abstract 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 2
- 235000011037 adipic acid Nutrition 0.000 abstract 2
- 239000001361 adipic acid Substances 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 2
- 239000013522 chelant Substances 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 230000008020 evaporation Effects 0.000 abstract 2
- 238000002156 mixing Methods 0.000 abstract 2
- 229920001220 nitrocellulos Polymers 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- GFAZHVHNLUBROE-UHFFFAOYSA-N 1-hydroxybutan-2-one Chemical compound CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 abstract 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000020 Nitrocellulose Substances 0.000 abstract 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000012263 liquid product Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000012260 resinous material Substances 0.000 abstract 1
- 238000007493 shaping process Methods 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-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)
- Paints Or Removers (AREA)
Abstract
A stable complex titanic acid ester derived from a hydroxy ketone, hydroxy aldehyde, or keto-enolic compound and ortho-titanic acid or a halide or ester thereof, is caused to react and combine with a hydroxyl-containing compound having a molecular weight of at least 500. The reaction results in the formation of cross-linked high molecular weight compounds which are insoluble in common organic solvents. The hydroxyl-containing compound of molecular weight of at least 500 may be a cellulose acetate, nitrate, or other cellulose derivative; a polyester, e.g. a polymerized ester of adipic acid and trimethylol propane; a polyglucose ethyl ether or other sugar derivative; or a formaldehyde condensation product such as a polyvinyl formal. The complex titanic acid ester may be obtained from titanic acid, or a halide or ester thereof, and diacetone alcohol, beta-ketobutanol, beta-hydroxy-butyr-aldehyde, acetoacetic ester, diacetyl, acetyl acetone or a polymeric vinyl-methyl ketone, and is probably a chelate type of compound. It may be obtained by an ester exchange process, e.g. from tetraethyl titanate and diacetone alcohol, and such process may take place at room temperature or elevated temperature. The complex titanic acid ester may be added to a solution of the high molecular weight compound containing hydroxyl groups and the reaction may be completed after evaporation of the solvent, if necessary with heating. The solutions or compositions may be formed into filaments, films or other articles which are rendered insoluble after the final shaping. In an example, a stable titanium ester, obtained from tetrabutyl titanate and diacetone alcohol, is mixed with a solution of cellulose nitrate in butanol, butyl acetate and ethyl acetate. The solution is cast in a thin layer and the solvent is evaporated, leaving a clear film which is insoluble in organic solvents. In another example, a complex titanic acid ester, obtained from tetrapropyl titanate and acetyl acetone, is mixed with a solution in ethyl acetate of a viscous polyester, containing 10 per cent of hydroxyl groups and obtained by thermal esterification of adipic acid with trimethylol propane. The solution is sprayed into a metal sheet, and after evaporation of the solvent, if desired at elevated temperature, a hard coating which is insoluble in organic solvents is obtained. In another example, polyvinyl formal is dissolved in a mixture of ethyl acetate and methanol. A mixture of titanium tetrabutylate and aceto-acetic ester is added, and the solution is then formed into a film which, on drying, becomes insoluble in organic solvents. In another example, a polyglucose ethyl ether is dissolved in benzene and mixed with a reaction product of titanium tetrabutylate with acetoacetic ester. A clear film insoluble in benzene is obtained. Specification 734,113 is referred to.ALSO:A stable complex titanic acid ester is prepared from a hydroxy ketone, hydroxy aldehyde, or keto-enolic compound and ortho-titanic acid or a halide or ester thereof. It may be obtained, as described in Specification 734,113, by reacting titanic acid or a halide or ester thereof, with diacetone alcohol, b -ketobutanol, b -hydroxybutyraldehyde, acetoacetic ester, diacetyl or acetyl acetone, and is probably a chelate type of compound. It may also be obtained by ester exchange, e.g. from tetraethyl titanate and diacetone alcohol, and such reaction may take place at room temperature or elevated temperature. In an example, a stable titanic ester is obtained by mixing tetrapropyl titanate with acetyl acetone. After the evolution of heat has ceased, a complex orange-yellow, liquid product is obtained. In another example, the complex ester is obtained by mixing tetrabutyl titanate and aceto-acetic ester. The complex esters are reacted with high molecular weight hydroxy compounds to form resinous materials (see Group IV (a)).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE734114X | 1950-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB734114A true GB734114A (en) | 1955-07-27 |
Family
ID=6641375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17656/51A Expired GB734114A (en) | 1950-08-30 | 1951-07-25 | Process of producing reaction products of titanic acid esters with high molecular weight compounds containing hydroxyl groups |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB734114A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258475A (en) * | 1963-08-13 | 1966-06-28 | Faulkner Raymond Noel | Film-forming organometallic derivatives of fatty acids |
-
1951
- 1951-07-25 GB GB17656/51A patent/GB734114A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258475A (en) * | 1963-08-13 | 1966-06-28 | Faulkner Raymond Noel | Film-forming organometallic derivatives of fatty acids |
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