GB955127A - Methacrylic and acrylic esters of halogenated polyphenols and polymers derived therefrom - Google Patents
Methacrylic and acrylic esters of halogenated polyphenols and polymers derived therefromInfo
- Publication number
- GB955127A GB955127A GB3573462A GB3573462A GB955127A GB 955127 A GB955127 A GB 955127A GB 3573462 A GB3573462 A GB 3573462A GB 3573462 A GB3573462 A GB 3573462A GB 955127 A GB955127 A GB 955127A
- Authority
- GB
- United Kingdom
- Prior art keywords
- octochlorodihydroxydiphenyl
- methacrylate
- nonachloromonohydroxydiphenyl
- ester
- acrylate
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title abstract 2
- 229920000642 polymer Chemical class 0.000 title abstract 2
- 125000005395 methacrylic acid group Chemical group 0.000 title 1
- 150000008442 polyphenolic compounds Chemical class 0.000 title 1
- 235000013824 polyphenols Nutrition 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 238000005406 washing Methods 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 229910052797 bismuth Inorganic materials 0.000 abstract 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000012153 distilled water Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 159000000011 group IA salts Chemical class 0.000 abstract 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006305 unsaturated polyester Polymers 0.000 abstract 1
- 239000003643 water by type Substances 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
- C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention relates to methacrylates or acrylates of nonachloromonohydroxydiphenyl or of octochlorodihydroxydiphenyl having the formula: <FORM:0955127/C2/1> where R1 is a hydrogen atom or a methyl group, R2 is the nonachlorodiphenyl radical and R3 is the octochlorodiphenyl radical. The esters are produced by reacting a perchloro-mono- or diphenol derived from diphenyl, in the form of an isomer or a mixture of isomers of nonachloromonohydroxydipheny or octochlorodihydroxydiphenyl respectively, in an aqueous medium at reduced or moderate temperature with an alkaline salt of the diphenol and an acid chloride derived from methacrylic acid or acrylic acid to form the ester in the form of a precipitate, separating the precipitated ester from the solution, washing the ester in water until the washing water was clear of chloride ions, and drying the ester. In an example methacrylyl chloride is dripped into a solution of the disodic salt of octochlorodihydroxydiphenyl at a temperature not exceeding 1 DEG C. The ester, which is precipitated as a fine powder as it is formed, is collected on a filter, then washed with cold distilled water until the chloride ions had completely disappeared from the washing waters, and finally dried under reduced pressure at 50 DEG C. to give a product mainly composed of a mixture of mono- and di-methacrylate of octochlorodihydroxydiphenyl. Other examples describe the preparation of di-acrylate of octochlorodihydroxydiphenyl, methacrylate of nonachloromonohydroxydiphenyl, acrylate of nonachloromonohydroxydiphenyl.ALSO:A copolymer of a methacrylate or acrylate nonachloromonohydroxydiphenyl or of octochlorodihydroxydiphenyl having the formula: <FORM:0955127/C3/1> , or <FORM:0955127/C3/2> , or <FORM:0955127/C3/3> where R1 is a hydrogen atom or a methyl group, R2 is the nonachlorodiphenyl radical and R3 is the octochlorodiphenyl radical is obtained by the copolymerization with compounds such as styrene, methyl methacrylate, acrylonitrile, and unsaturated polyesters e.g. vinyl acetate. One or more sulphuretted and/or oxygenated derivatives of phosphorus, antimony or bismuth may be added to the precursor of the polymer prior to polymerization. In an example the polymerization of methacrylate of nonachloromonohydroxydiphenyl was carried out in the absence of air with the aid of benzoyl peroxide. Other examples show the copolymerization of di-acrylate of octochlorodihydroxydiphenyl and methyl methacrylate, and the mixture of mono- and di-methacrylate of octochlorodihydroxydiphenyl with methyl methacrylate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR873679A FR1308003A (en) | 1961-09-20 | 1961-09-20 | Methacrylic and acrylic esters of halogenated polyphenols and derived polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB955127A true GB955127A (en) | 1964-04-15 |
Family
ID=8763152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3573462A Expired GB955127A (en) | 1961-09-20 | 1962-09-19 | Methacrylic and acrylic esters of halogenated polyphenols and polymers derived therefrom |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE621655A (en) |
| FR (1) | FR1308003A (en) |
| GB (1) | GB955127A (en) |
| LU (1) | LU42372A1 (en) |
| NL (1) | NL283387A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998056749A1 (en) * | 1997-06-10 | 1998-12-17 | Minnesota Mining And Manufacturing Company | Halogenated acrylates and polymers derived therefrom |
| CN113372927A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| CN113372926A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| CN113372924A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Polymerizable compound, liquid crystal composition thereof and liquid crystal display device |
| CN113372925A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN113372928A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
-
0
- NL NL283387D patent/NL283387A/xx unknown
- BE BE621655D patent/BE621655A/xx unknown
-
1961
- 1961-09-20 FR FR873679A patent/FR1308003A/en not_active Expired
-
1962
- 1962-09-17 LU LU42372D patent/LU42372A1/xx unknown
- 1962-09-19 GB GB3573462A patent/GB955127A/en not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998056749A1 (en) * | 1997-06-10 | 1998-12-17 | Minnesota Mining And Manufacturing Company | Halogenated acrylates and polymers derived therefrom |
| US6005137A (en) * | 1997-06-10 | 1999-12-21 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
| US6288266B1 (en) | 1997-06-10 | 2001-09-11 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
| US6313245B1 (en) | 1997-06-10 | 2001-11-06 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
| US6362379B2 (en) | 1997-06-10 | 2002-03-26 | 3M Innovative Properties Company | Method of making chlorofluoroethers |
| CN113372927A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| CN113372926A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| CN113372924A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Polymerizable compound, liquid crystal composition thereof and liquid crystal display device |
| CN113372925A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN113372928A (en) * | 2020-03-09 | 2021-09-10 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| TWI771940B (en) * | 2020-03-09 | 2022-07-21 | 大陸商江蘇和成顯示科技有限公司 | Polymerizable compound and its liquid crystal composition and liquid crystal display device |
| CN113372925B (en) * | 2020-03-09 | 2022-12-09 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN113372927B (en) * | 2020-03-09 | 2022-12-13 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| CN113372928B (en) * | 2020-03-09 | 2022-12-13 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| CN113372926B (en) * | 2020-03-09 | 2022-12-16 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| NL283387A (en) | |
| BE621655A (en) | |
| FR1308003A (en) | 1962-11-03 |
| LU42372A1 (en) | 1962-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3025271A (en) | Mixed esters of citric acid and polymers thereof | |
| GB834346A (en) | Impact-resistant synthetic resinous compositions | |
| DE1106960B (en) | Process for the production of polymers | |
| GB955127A (en) | Methacrylic and acrylic esters of halogenated polyphenols and polymers derived therefrom | |
| US3839393A (en) | Ammonium and alkali metal salts of sulfato-alkane acrylates and methacrylates | |
| US2255483A (en) | Inhibited polymerizable unsaturated organic compound | |
| US3004932A (en) | Unsaturated beta-diketones and polymers and co-polymers thereof | |
| US2715116A (en) | Emulsion polymerisation of styrene compounds | |
| GB1015619A (en) | Improvements in or relating to vinylaromatic polymer preparation | |
| US2163305A (en) | Process of polymerizing acrylic and alkacrylic compounds | |
| US3067186A (en) | Vinyl chloride polymerisation process | |
| US2735837A (en) | Interpolymers of z | |
| US3143535A (en) | 2, 3-dibromohexahydro-4, 7-methanoindan-5-yl acrylate and methacrylate and polymers thereof | |
| DE1104700B (en) | Process for the production of polymerisation plastics | |
| US2341334A (en) | Interpolymers of alkylidene esters of alpha-methylene monocarboxylic acids with vinyl and vinylidene compounds | |
| DE1301084B (en) | Process for the production of copolymers | |
| DE872120C (en) | Process for the production of polymers or copolymers of unsaturated compounds | |
| US3296180A (en) | Vinyl chloride resins plasticized with substituted cyclohexyl alkyl phthalates | |
| US3252951A (en) | Polymerization of acrylonitrile polymers in the presence of condensed phosphorus acids | |
| US3484416A (en) | Method of preparing vinylidene cyanide - unsaturated sulfonic acid interpolymers | |
| GB498383A (en) | Manufacture of solutions of highly polymeric substances | |
| DE1020458B (en) | Process for the manufacture of spinnable acrylonitrile polymerization products | |
| GB732912A (en) | Improvements in or relating to the hydrolysis of polymers and to soil-conditioning agents comprising the hydrolysed polymers | |
| DE1815142B2 (en) | Process for the polymerization of vinyl chloride | |
| US3057829A (en) | Copolymers of diallyl barbituric acids and vinyl monomers |