US2419221A - Copolymers of 2-halogeno-allyl alcohol or 2-halogeno-allyl esters - Google Patents
Copolymers of 2-halogeno-allyl alcohol or 2-halogeno-allyl esters Download PDFInfo
- Publication number
- US2419221A US2419221A US442453A US44245342A US2419221A US 2419221 A US2419221 A US 2419221A US 442453 A US442453 A US 442453A US 44245342 A US44245342 A US 44245342A US 2419221 A US2419221 A US 2419221A
- Authority
- US
- United States
- Prior art keywords
- copolymer
- allyl
- halogeno
- solution
- water
- 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 - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 title description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000004342 Benzoyl peroxide Substances 0.000 description 10
- 235000019400 benzoyl peroxide Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 150000002894 organic compounds Chemical class 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- OSCXYTRISGREIM-UHFFFAOYSA-N 2-chloroprop-2-en-1-ol Chemical compound OCC(Cl)=C OSCXYTRISGREIM-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- -1 ALLYL ESTERS Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NPAGADDDGUIURB-UHFFFAOYSA-N 2-chloroprop-2-enyl acetate Chemical compound CC(=O)OCC(Cl)=C NPAGADDDGUIURB-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- MRDPKFXEUMUFQJ-IHWYPQMZSA-N [(z)-3-chloroprop-2-enyl] acetate Chemical compound CC(=O)OC\C=C/Cl MRDPKFXEUMUFQJ-IHWYPQMZSA-N 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- SGDUJTQUQYLRFH-ONEGZZNKSA-N 2-chloroprop-2-enyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OCC(Cl)=C SGDUJTQUQYLRFH-ONEGZZNKSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical class ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 241000013355 Mycteroperca interstitialis Species 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 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
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/20—Esters containing halogen
Definitions
- This invention relates to copolymers of 2-halogeno-allyl alcohols or 2-halogeno-allyl esters.
- esters of 2-chloro-ally1 alcohol containing but one ethylenic linkage, viz. 2-chloro-allyl chloroacetate, have beenproposed as "modifiers in the polymerization of polymerizable organic compounds also containing but one ethylenic linkage, such as vinyl compounds and vinylidene chloride.
- 2-halogeno-allyl compounds we prefer the more readily available, more stable 2-chloro-allyl compounds.
- 2-chloroallyl esters which we have found especially useful in practicing our invention, the following can be mentioned: 2-chloro-allyl esters of monobasic in- -tate the copolymer.
- acrylic acids such as methacrylic acid, ethacrylic acid and a-ChlOlO- acrylic acid, esters of acrylic acids, e. g. methyl acrylate, isobutyl acrylate, methyl methacrylate, n-butyl methyacrylate and methyl cz-ChlOlO- acrylate.
- the proportion of monomeric 2-halogeno-allyl compound to polymerizable organic compound containing an ethylenic linkage conjugated with another double-bond linkage can be any desired ratio. However, we have found that in the copolymer the ratio of 2-halogeno-allyl compound to the second compound is never greater than 1:1. More than one 2-halogeno-ally1 compound can be copolymerized with one polymerizable organic compound containin an ethylenic linkage conjugated with another double-bond linkage, and more than one of the compounds containing the conjugated system can be employed with on 2-halogeno-allyl compound.
- the monomers are mixed in the desired ratio, a polymerization catalyst, e. g. an organic peroxide,- added, and the resulting mixture allowed to polymerize, advantageously with warming.
- a polymerization catalyst e. g. an organic peroxide
- Any of the catalysts known to effect the polymerization of vinyl compounds can be employed.
- the resulting resin is dissolved in a suitable solvent, and the solution poured into a nonsolvent for the resin (usually water) to precipitate the resin.
- the precipitated resin is then washed with water (and steamed,'if necessary) and finally dried.
- the following examples and table will serve to illustrate th copolymers and the process for preparing them.
- EXAMPLE 1 COPOLYMER or 2-CHLORO-ALLYL ALCOHOL AND METHYL-a-METHACRYLATE
- a solution of 5 g. of methyl a-methacrylate, 5 g. of 2-chloro-allyl alcohol and 0.05 g. of benzoyl peroxide was prepared and placed in an Erlenmeyer flask. The flask was stoppered and placed in an oven at 40 C. After four and one-half months the mixture was found to be solid and slightly yellow in color. The product was dissolved in acetone and the solution diluted to cc. with acetone.
- the diluted solution was filtered and then poured into cold water to precipi-
- the cream colored, fibrous precipitate was soaked for two hours, filtered and dried in the air at room temperature.
- the yield was 5.2 g.
- the copolymer contained chlorine equal to 8.27% by weight.
- EXAMPLE 4 --COPOLYMER or 2-CHLORO-ALLYL CHLORIDE AND METHYL or-METHACRYLATE'
- a solution of 50 g. of methyl methacrylate, 56 g. of 2-chloro-allyl chloride and 1.06 g. of benzoyl peroxide was prepared and heated on a steam bath. After twenty-seven and one-half hours heating, 1.06 g. of benzoyl peroxide were added to the yellow, viscous liquid. At the end of two further hours of heating, the reaction mixture was very viscous. Heating was discontinued and the reaction mixture dissolved in acetone. The acetone solution was poured into hot Water to precipitate the copolymer.
- the copolymer was then steamed for five hours.
- the copolymer was redissolved'in acetone and the acetone solution again poured into water to precipitate the copolymer.
- the copolymer was soaked in ethanol and again dissolved in acetone.
- the acetone solution was again poured into water to precipitate the copolymer.
- the copolymer was filtered off and dried at room temperature. The slightly yellow, friable product weighed 75 g. and con tained 28% by weight of chlorine.
- the copolymer was then redissolved in dioxane and reprecipitated by pouring the solution into water.
- the copolymer was filtered ofi and dried in the air at room temperature.
- the colorless, friable copolymer weighed 5.7 g. and contained 15.49% by weight of chlorine.
- EXAMPLE 8 COPOLYMER or Z-CHLORO-ALLYL ACETATE AND ACRYLIC Acrn ExAMrLE 9.COPOLYMER or Z-CHLoRO-ALLYL ACETATE AND MErHYL ME'rHAcaYLArE A solution of 13.45'g. of2-chloroallyl acetate, 10 g. of methyl methacrylate, and 0.12 g. of benzoyl peroxide was prepared and sealed into a glass tube. The tube and contents "were heated in a water bath at 50 C'. for seventeen days, at the end of which time the product was hazy and' faintly yellow.
- the copolymer was dissolved in acetone, the solution filteredgaj'nd the copolymer precipitated into water and soaked several hours in fresh water. It was then, steamed for four hours, redissolved in acetone, precipitated into distilled water, and soaked'in, fresh distilled water. The product was dried-.,in the air at room temperature.
- the colorless, friable material weighed 17.2 g. and contained 11.97% of chlorine.
- EXAMPLE 10 --CoPoLY1 ⁇ rn-i i or"- 2-CHLoao-ALLYL ACETATE AND 1STYRENE
- a solution of 13.45 g. of 2-chloroallyl acetate, 10.4 g. of styrene, and 0.12 g, of benzoyl peroxide was prepared and'sealed into a glass tube. The tube and contents were heated in a water bath at 50 C. for twenty-one days, at the end of which time the product. was very viscous, clear, and yellow in color. It was dissolved in dioxane, poured into distilled water, steamed for four hours, and redissolved in dioxane. This solution was precipitated into distilled water, the copolymer soaked'for three hours, filtered, and dried in the air at room temperature. The colorless, friable product weighed 12.4 g. and contained 7.42% of chlorine.
- Z-CHLORO-ALLYL ACETATE COPOLYMERS 26 acrylic acid, 10.7 0. 077 100, 16.6 hr 13. 67 1:1. 46 methyl acryiate. 12.8 0. 078 100, 3 days 13. 48 1:1. 6 13. 6 methyl acryiate, 17.2 0. 07 100, 2 days 9. 68 1:2. 76
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US442453A US2419221A (en) | 1942-05-11 | 1942-05-11 | Copolymers of 2-halogeno-allyl alcohol or 2-halogeno-allyl esters |
| FR940678D FR940678A (fr) | 1942-05-11 | 1946-12-27 | Nouveaux copolymères des esters carboxyliques de 2-halogénoallyle |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US442453A US2419221A (en) | 1942-05-11 | 1942-05-11 | Copolymers of 2-halogeno-allyl alcohol or 2-halogeno-allyl esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2419221A true US2419221A (en) | 1947-04-22 |
Family
ID=23756836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US442453A Expired - Lifetime US2419221A (en) | 1942-05-11 | 1942-05-11 | Copolymers of 2-halogeno-allyl alcohol or 2-halogeno-allyl esters |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2419221A (fr) |
| FR (1) | FR940678A (fr) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2498099A (en) * | 1946-04-19 | 1950-02-21 | Us Rubber Co | Interpolymers of styrene, fumaric esters, and chlorinated alkenes |
| US2498084A (en) * | 1946-04-19 | 1950-02-21 | Us Rubber Co | Interpolymers of fumaric esters and a chlorinated alkene |
| US2557189A (en) * | 1947-01-10 | 1951-06-19 | Celanese Corp | Copolymers of unsaturated esters |
| US2563611A (en) * | 1951-08-07 | Phen ylallyl alcohol | ||
| US2600421A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers of acrylates and allyl esters |
| US2600383A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers from allyl esters and methacrylic esters |
| US2600448A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers from allyl esters and acrylic esters |
| US2600414A (en) * | 1947-08-22 | 1952-06-17 | William C Mast | Vulcanization of acrylic resins |
| US2600446A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers of methacrylates and allyl esters |
| US2951831A (en) * | 1955-12-05 | 1960-09-06 | Monsanto Chemicals | Terpolymer of a conjugated diolefin, a styrene, and an allyl alcohol |
| US3245954A (en) * | 1961-04-05 | 1966-04-12 | Shell Oil Co | Hydroxy-containing polymers of mesityl oxides |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2160941A (en) * | 1938-04-01 | 1939-06-06 | Dow Chemical Co | Vinylidene chloride co-polymers |
| US2160943A (en) * | 1938-05-02 | 1939-06-06 | Dow Chemical Co | Vinylidene chloride co-polymers |
| US2186360A (en) * | 1938-02-23 | 1940-01-09 | Dow Chemical Co | Styrene copolymers |
| US2205390A (en) * | 1938-06-10 | 1940-06-25 | Dow Chemical Co | Copolymers of styrene and 2-chloroallyl esters |
| GB540168A (en) * | 1938-12-30 | 1941-10-08 | American Cyanamid Co | Resinous compositions and methods of preparing same |
| US2273891A (en) * | 1939-02-18 | 1942-02-24 | Pittsburgh Plate Glass Co | Method of polymerizing polymerizable materials containing more than one polymerizable grouping |
| US2308495A (en) * | 1939-10-31 | 1943-01-19 | Gen Electric | Interpolymerization product of an unsaturated alkyd resin and a monoallyl ester of anonvinylic monoesterifiable acid |
| US2332460A (en) * | 1939-08-10 | 1943-10-19 | Pittsburgh Plate Glass Co | Polymerized esters of polymeric unsaturated alcohols and method of manufacture thereof |
| US2332897A (en) * | 1940-06-07 | 1943-10-26 | Gen Electric | Synthetic composition comprising hydrolyzed, acetalized, and/or ketalized copolymers of vinyl esters and unsaturated ketones containing at least one ch=c grouping |
| US2332900A (en) * | 1940-07-23 | 1943-10-26 | Gen Electric | Synthetic composition comprising hydrolyzed, acetalized, and/or ketalized polymers of allyl esters |
| US2334358A (en) * | 1938-11-16 | 1943-11-16 | American Enka Corp | Artificial cellulosic filament delustered with titanium salt |
| US2388851A (en) * | 1942-05-11 | 1945-11-13 | Eastman Kodak Co | Soluble material which becomes insoluble upon separation from solvent |
-
1942
- 1942-05-11 US US442453A patent/US2419221A/en not_active Expired - Lifetime
-
1946
- 1946-12-27 FR FR940678D patent/FR940678A/fr not_active Expired
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2186360A (en) * | 1938-02-23 | 1940-01-09 | Dow Chemical Co | Styrene copolymers |
| US2160941A (en) * | 1938-04-01 | 1939-06-06 | Dow Chemical Co | Vinylidene chloride co-polymers |
| US2160943A (en) * | 1938-05-02 | 1939-06-06 | Dow Chemical Co | Vinylidene chloride co-polymers |
| US2205390A (en) * | 1938-06-10 | 1940-06-25 | Dow Chemical Co | Copolymers of styrene and 2-chloroallyl esters |
| US2334358A (en) * | 1938-11-16 | 1943-11-16 | American Enka Corp | Artificial cellulosic filament delustered with titanium salt |
| GB540168A (en) * | 1938-12-30 | 1941-10-08 | American Cyanamid Co | Resinous compositions and methods of preparing same |
| US2273891A (en) * | 1939-02-18 | 1942-02-24 | Pittsburgh Plate Glass Co | Method of polymerizing polymerizable materials containing more than one polymerizable grouping |
| US2332460A (en) * | 1939-08-10 | 1943-10-19 | Pittsburgh Plate Glass Co | Polymerized esters of polymeric unsaturated alcohols and method of manufacture thereof |
| US2308495A (en) * | 1939-10-31 | 1943-01-19 | Gen Electric | Interpolymerization product of an unsaturated alkyd resin and a monoallyl ester of anonvinylic monoesterifiable acid |
| US2332897A (en) * | 1940-06-07 | 1943-10-26 | Gen Electric | Synthetic composition comprising hydrolyzed, acetalized, and/or ketalized copolymers of vinyl esters and unsaturated ketones containing at least one ch=c grouping |
| US2332900A (en) * | 1940-07-23 | 1943-10-26 | Gen Electric | Synthetic composition comprising hydrolyzed, acetalized, and/or ketalized polymers of allyl esters |
| US2388851A (en) * | 1942-05-11 | 1945-11-13 | Eastman Kodak Co | Soluble material which becomes insoluble upon separation from solvent |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2563611A (en) * | 1951-08-07 | Phen ylallyl alcohol | ||
| US2498099A (en) * | 1946-04-19 | 1950-02-21 | Us Rubber Co | Interpolymers of styrene, fumaric esters, and chlorinated alkenes |
| US2498084A (en) * | 1946-04-19 | 1950-02-21 | Us Rubber Co | Interpolymers of fumaric esters and a chlorinated alkene |
| US2557189A (en) * | 1947-01-10 | 1951-06-19 | Celanese Corp | Copolymers of unsaturated esters |
| US2600414A (en) * | 1947-08-22 | 1952-06-17 | William C Mast | Vulcanization of acrylic resins |
| US2600421A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers of acrylates and allyl esters |
| US2600383A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers from allyl esters and methacrylic esters |
| US2600448A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers from allyl esters and acrylic esters |
| US2600446A (en) * | 1949-07-15 | 1952-06-17 | Rohm & Haas | Copolymers of methacrylates and allyl esters |
| US2951831A (en) * | 1955-12-05 | 1960-09-06 | Monsanto Chemicals | Terpolymer of a conjugated diolefin, a styrene, and an allyl alcohol |
| US3245954A (en) * | 1961-04-05 | 1966-04-12 | Shell Oil Co | Hydroxy-containing polymers of mesityl oxides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR940678A (fr) | 1948-12-20 |
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