GB733224A - Titanium organic compounds - Google Patents
Titanium organic compoundsInfo
- Publication number
- GB733224A GB733224A GB26651/51A GB2665151A GB733224A GB 733224 A GB733224 A GB 733224A GB 26651/51 A GB26651/51 A GB 26651/51A GB 2665151 A GB2665151 A GB 2665151A GB 733224 A GB733224 A GB 733224A
- Authority
- GB
- United Kingdom
- Prior art keywords
- titanium
- groups
- alkoxy
- acid
- titanate
- 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
- -1 Titanium organic compounds Chemical class 0.000 title abstract 14
- 229910052719 titanium Inorganic materials 0.000 title abstract 10
- 239000010936 titanium Substances 0.000 title abstract 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 7
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical group CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000009835 boiling Methods 0.000 abstract 3
- 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 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 239000003973 paint Substances 0.000 abstract 3
- 239000004014 plasticizer Substances 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- GGAFYKJNIMENBK-UHFFFAOYSA-L C(C=CC)(=O)[O-].C(C=CC)(=O)[O-].[Ti+2] Chemical compound C(C=CC)(=O)[O-].C(C=CC)(=O)[O-].[Ti+2] GGAFYKJNIMENBK-UHFFFAOYSA-L 0.000 abstract 2
- AFDSQFOUIHCVNU-UHFFFAOYSA-M C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCC)O[Ti+](OCCCC)OCCCC Chemical compound C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCC)O[Ti+](OCCCC)OCCCC AFDSQFOUIHCVNU-UHFFFAOYSA-M 0.000 abstract 2
- YISQSRGGFNRZSF-UHFFFAOYSA-K C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCC)O[Ti+3] Chemical compound C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCCCCCCC=C/CC=C/CCCCC)(=O)[O-].C(CCC)O[Ti+3] YISQSRGGFNRZSF-UHFFFAOYSA-K 0.000 abstract 2
- QDAQQGWDVYCOOX-UHFFFAOYSA-K C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)O[Ti+3] Chemical compound C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)O[Ti+3] QDAQQGWDVYCOOX-UHFFFAOYSA-K 0.000 abstract 2
- ZWNXEFJKNIKOMT-UHFFFAOYSA-M CC(=C)C([O-])=O.CCCCO[Ti+](OCCCC)OCCCC Chemical compound CC(=C)C([O-])=O.CCCCO[Ti+](OCCCC)OCCCC ZWNXEFJKNIKOMT-UHFFFAOYSA-M 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- PYPDMIQMPWEFHX-UHFFFAOYSA-N [Pb].[Co] Chemical compound [Pb].[Co] PYPDMIQMPWEFHX-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- UFYHKVNWMIPAFW-UHFFFAOYSA-L butan-1-olate 2-methylprop-2-enoate titanium(4+) Chemical compound C(C(=C)C)(=O)[O-].C(C(=C)C)(=O)[O-].C(CCC)O[Ti+2]OCCCC UFYHKVNWMIPAFW-UHFFFAOYSA-L 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003989 dielectric material Substances 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- HTQDZHOOVXXKSL-UHFFFAOYSA-L propanoate;titanium(2+) Chemical compound [Ti+2].CCC([O-])=O.CCC([O-])=O HTQDZHOOVXXKSL-UHFFFAOYSA-L 0.000 abstract 2
- 235000015096 spirit Nutrition 0.000 abstract 2
- 239000004408 titanium dioxide Substances 0.000 abstract 2
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 abstract 2
- 239000003981 vehicle Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- 239000005639 Lauric acid Substances 0.000 abstract 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 229940116333 ethyl lactate Drugs 0.000 abstract 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 abstract 1
- 235000020778 linoleic acid Nutrition 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 229920005992 thermoplastic resin Polymers 0.000 abstract 1
- 150000003608 titanium Chemical class 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
- 229940057402 undecyl alcohol Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
Polymeric alkoxy titanium acylates wherein the alkoxy groups are derived from saturated aliphatic alcohols and the acylate groups from aliphatic mono- or di-carboxylic acids are prepared by the following methods. They may be produced from the monomeric alkoxy titanium acylates, derived from aliphatic mono-carboxylic acids, by means of partial hydrolysis; when the acyl groups are unsaturated polymerizable groups, the monomers may be polymerized and, if desired, partially hydrolysed to yield polymers having properties of the thermoplastic resins as well as those of the condensation polymers. The polymeric alkoxy titanium acylates wherein the acylate groups are derived from the dibasic acids, are prepared by reacting a tetraalkyl titanate with the dibasic acid, there being partial displacement of alkoxy groups in the form of the corresponding alcohols. The products are useful in paint vehicles as plasticizers or bodying agents (see Group III) and in dielectrics. In examples (1) poly(dibutoxy titanium mono-maleate) is prepared by heating tetra-butyl titanate with maleic acid and distilling off the displaced butanol; the polymer of M.W. 2230 is copolymerized with styrene using benzoyl peroxide as catalyst; (2) tributoxy titanium mono-methacrylate is copolymerized with methyl methacrylate; (3) dibutoxy titanium di-methacrylate is copolymerized with styrene or with butadiene in toluene using benzoyl peroxide as catalyst; (4) dipentoxy titanium dicrotonate is partially hydrolysed in ethereal solution by addition thereto of a small amount of water, the product being a solid mouldable resin. The invention also includes an example wherein diundecoxy titanium dipropionate is added to a solution of cellulose acetate in ethyl lactate, the product being capable of forming clear, hard fibres. The production of the monomers is described (see Group IV (b)). Specification 479,470 is referred to.ALSO:The invention comprises alkoxy titanium acylates in which the alkoxy portion of the molecule is derived from a saturated aliphatic alcohol and the acylate portion from an aliphatic monocarboxylic acid. Preferably, the alkoxy group is unsubstituted and contains 2-20 carbon atoms and the acylate group 3-36 carbon atoms; desirably, there are present 1-3 alkoxy groups and 1-3 carboxyl groups per titanium atom, the sum of both groups being substantially 4 per titanium atom. The compounds may be prepared by reacting a tetra-alkyl titanate with a carboxylic acid, the displaced alcohol being removed by distillation under reduced pressure. When the acid would boil at a lower temperature than the alcohol to be displaced, then the titanate of an alcohol boiling at a lower temperature than the acid is heated with the appropriate amount of the higher boiling alcohol and the displaced alcohol distilled off whereupon the resulting titanate containing mixed alkoxy groups is heated with the acid and the displaced remaining lower boiling alcohol distilled off. The tetra-alkyl titanates may be prepared by reacting titanium tetrachloride with a monohydric alcohol, for example, as described in Specification 479,470 or in the case of higher alcohols by ester-interchange of the latter with the titanate of a lower alcohol. The alkoxy titanium acylates may be used as plasticizers or bodying agents for paints, or used in dielectrics, and they may be polymerized or hydrolysed to titanium dioxide or titanium complexes (see Groups III and IV (a)). In examples (1) linoleic acid is heated with tetrabutyl titanate under reduced pressure yielding, according to the proportions used, tributoxy titanium monolinoleate or monobutoxy titanium trilinoleate; (2) methacrylic acid is reacted as in (1) yielding tributoxy titanium monomethacrylate or dibutoxy titanium dimethacrylate; (3) lauric acid is reacted as in (1) yielding monobutoxy titanium trilaurate; (4) undecyl alcohol is reacted with tetrabutyl titanate to yield diundecoxy dibutoxy titanate which is reacted with propionic acid to give diundecoxy titanium dipropionate; (5) tetra-amyl titanate is reacted with crotonic acid as in (1) yielding dipentoxy titanium dicrotonate.ALSO:Monomeric and polymeric alkoxy titanium acylates wherein the acylate groups are derived from aliphatic mono-carboxylic acids and polymeric alkoxy titanium acylates wherein the acylate groups are derived from aliphatic dicarboxylic acids (see Groups IV (a) and IV (b)) may be used as plasticizers or bodying agents for paint vehicles. The compounds may also be hydrolysed to titanium dioxide or complexes. According to examples, hard films may be obtained from mixtures of (1) tributoxy titanium monolinoleate and a cobalt-lead drier; (2) monobutoxy titanium trilinoleate, bodied linseed oil, mineral spirits and a cobalt-lead drier; (3) monobutoxy titanium trilaurate, castor oil and mineral spirits. Specification 479,470, [Group IV], is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US733224XA | 1950-11-29 | 1950-11-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB733224A true GB733224A (en) | 1955-07-06 |
Family
ID=22113055
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26651/51A Expired GB733224A (en) | 1950-11-29 | 1951-11-14 | Titanium organic compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB733224A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2913469A (en) * | 1956-08-07 | 1959-11-17 | Nat Lead Co | Organotitanium compounds and process of preparation |
US3087949A (en) * | 1960-04-04 | 1963-04-30 | Rinse Jacobus | Oxide acylates and metal oxide r-oxides of tetravalent group iv metals |
US4094853A (en) | 1975-05-15 | 1978-06-13 | Kenrich Petrochemicals, Inc. | Alkoxy titanate salts useful as coupling agents |
US4098758A (en) * | 1974-04-12 | 1978-07-04 | Kenrich Petrochemicals, Inc. | Inorganic-organic composites and methods of reacting the same with organo-titanium compounds |
US4748087A (en) * | 1984-06-08 | 1988-05-31 | The Wiggins Teape Group Limited | Plastic laminate of furniture foil and method of making |
-
1951
- 1951-11-14 GB GB26651/51A patent/GB733224A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2913469A (en) * | 1956-08-07 | 1959-11-17 | Nat Lead Co | Organotitanium compounds and process of preparation |
US3087949A (en) * | 1960-04-04 | 1963-04-30 | Rinse Jacobus | Oxide acylates and metal oxide r-oxides of tetravalent group iv metals |
US4098758A (en) * | 1974-04-12 | 1978-07-04 | Kenrich Petrochemicals, Inc. | Inorganic-organic composites and methods of reacting the same with organo-titanium compounds |
US4094853A (en) | 1975-05-15 | 1978-06-13 | Kenrich Petrochemicals, Inc. | Alkoxy titanate salts useful as coupling agents |
US4096110A (en) | 1975-05-15 | 1978-06-20 | Kenrich Petrochemicals, Inc. | Filled polyesters containing organic titanate esters |
US4122062A (en) | 1975-05-15 | 1978-10-24 | Kenrich Petrochemicals, Inc. | Alkoxy titanate salts useful as coupling agents |
US4748087A (en) * | 1984-06-08 | 1988-05-31 | The Wiggins Teape Group Limited | Plastic laminate of furniture foil and method of making |
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