GB889777A - Halogenated resbenzophenones and their etherified derivatives and compositions resistant to ultraviolet light - Google Patents
Halogenated resbenzophenones and their etherified derivatives and compositions resistant to ultraviolet lightInfo
- Publication number
- GB889777A GB889777A GB15241/59A GB1524159A GB889777A GB 889777 A GB889777 A GB 889777A GB 15241/59 A GB15241/59 A GB 15241/59A GB 1524159 A GB1524159 A GB 1524159A GB 889777 A GB889777 A GB 889777A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- methoxy
- chlorine
- halogenated
- chloro
- 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
- 239000000203 mixture Substances 0.000 title abstract 8
- 229910052801 chlorine Chemical group 0.000 abstract 6
- 239000000460 chlorine Chemical group 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052794 bromium Inorganic materials 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000012965 benzophenone Substances 0.000 abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 3
- 229920000728 polyester Polymers 0.000 abstract 3
- 239000003381 stabilizer Substances 0.000 abstract 3
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- -1 aliphatic hydroxy compound Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 230000006866 deterioration Effects 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- YESPMDRCFWSKRB-UHFFFAOYSA-N (3,5-dichloro-1-hydroxycyclohexa-2,4-dien-1-yl)-(2-hydroxyphenyl)methanone Chemical class ClC=1CC(C(=O)C2=C(C=CC=C2)O)(C=C(C=1)Cl)O YESPMDRCFWSKRB-UHFFFAOYSA-N 0.000 abstract 1
- QNQUXHSXTSZFBS-UHFFFAOYSA-N (5-bromo-4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical class C(CCCCCCCCCCC)OC1=CC(=C(C(=O)C2=CC=CC=C2)C=C1Br)O QNQUXHSXTSZFBS-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 abstract 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 abstract 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 abstract 1
- AQBFKBMMIDHCFS-UHFFFAOYSA-N 4-bromo-2-benzofuran-1,3-dione Chemical class BrC1=CC=CC2=C1C(=O)OC2=O AQBFKBMMIDHCFS-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004641 Diallyl-phthalate Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 150000008366 benzophenones Chemical class 0.000 abstract 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 150000001983 dialkylethers Chemical class 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 150000002895 organic esters Chemical class 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 235000013824 polyphenols Nutrition 0.000 abstract 1
- 239000011118 polyvinyl acetate Substances 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 229920001959 vinylidene polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/136—Phenols containing halogens
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Materials normally subject to deterioration by ultra-violet light are stabilized by incorporating therein a compound having the formula <FORM:0889777/IV (a)/1> wherein R represents hydrogen or alkyl, X represents bromine or chlorine but is chlorine where R is hydrogen and Y represents hydrogen, bromine or chlorine (see Group IV(b)). Materials which may be stabilized include polyvinyl chloride and acetate and mixtures thereof, vinyl and vinylidene polymers and copolymers generally, polyester compositions prepared by reacting a ,b -unsaturated polycarboxylic acids with an aliphatic hydroxy compound especially a dihydric alcohol and admixing the polyester with a polymerizable ethylenically unsaturated compound, e.g. styrene or diallyl phthalate, acrylates, methacrylates, melamineformaldehyde resins, phenolics, nylon, and epoxy resins. Specific stabilizing agents described include 5-chloro-2,4-dihydroxy-, 5-bromo2-hydroxy-4-methoxy-, 3,5-dibromo-2-hydroxy4-methoxy-, 5-bromo-2-hydroxy-4-dodecoxyand 5-chloro-2-hydroxy-4-methoxy-benzo-phenones. The preparation is described of films containing the stabilizers of the inventions by polymerization of polyester-styrene compositions in the presence of methyl ethyl ketone peroxide and from compositions comprising polyvinyl chloride, dioctylphthalate and cyclohexanone. The polyesters employed in the above compositions are obtained by heating together diethylene glycol, maleic anhydride, phthalic anhydride and tetrabromophthalic anhydride or similar mixtures containing tetrachlorophthalic acid, 1,4,5,6,7,7-hexachloroendo - cis - bicyclo-[2,2,1]5-heptene-2,3-dicarboxylic acid in place of the phthalic anhydride or both the phthalic and tetra bromophthalic anhydrides.ALSO:The invention comprises a homonuclear halogenated resobenzophenone having the genera1 formula <FORM:0889777/IV (b)/1> wherein R represents hydrogen or alkyl, X represents bromine or chlorine but is chlorine when R is hydrogen, and Y represents hydrogen, bromine or chlorine. A list of alkyl radicals which may be present is given extending from methyl to octadecyl and including various isomers. The 5-chloro- and 3,5-dichloro-dihydroxy benzophenones are prepared by chlorinating a solution of resbenzophenone in an inert solvent, e.g. dioxane, a dialkyl ether, chlorobenzene, benzene, glacial acetic acid, chloracetic acid or mixtures thereof. The 4-alkoxy-2-hydroxybenzophenones may be similarly halogenated or corresponding halogenated 2,4-dihydroxy-benzophenones mono-alkylated to obtain halogenated 4-alkoxy-2-hydroxy-benzophenones. Dimethyl sulphate and dodecyl bromide are specified as alkylating agents. In examples are described the preparations of 5-chloro- and 3,5-dichlororesbenzophenones and 5 - bromo - 2 - hydroxy - 4 - methoxy-, 3, 5 - dibromo - 2 - hydroxy - 4 - methoxy - 5 - chloro - 2 - hydroxy - 4 - methoxy-and 5 - bromo - 4 - dodecoxy - 2 - hydroxy - benzophenones. The substituted benzophenones of the invention are incorporated as stabilisers in materials normally subject to deterioration on exposure to ultra-violet light, e.g. resinous condensation and polymerisation products (see Group IV (a)) and cellulose organic esters and regenerated cellulose.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US889777XA | 1958-05-07 | 1958-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB889777A true GB889777A (en) | 1962-02-21 |
Family
ID=22214620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15241/59A Expired GB889777A (en) | 1958-05-07 | 1959-05-04 | Halogenated resbenzophenones and their etherified derivatives and compositions resistant to ultraviolet light |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB889777A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109096075A (en) * | 2018-08-10 | 2018-12-28 | 宜都市华阳化工有限责任公司 | The process for separation and purification of 5- chlorine-2-hydroxyl -4- methoxy benzophenone |
-
1959
- 1959-05-04 GB GB15241/59A patent/GB889777A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109096075A (en) * | 2018-08-10 | 2018-12-28 | 宜都市华阳化工有限责任公司 | The process for separation and purification of 5- chlorine-2-hydroxyl -4- methoxy benzophenone |
| CN109096075B (en) * | 2018-08-10 | 2021-03-30 | 宜都市华阳化工有限责任公司 | Separation and purification method of 5-chloro-2-hydroxy-4-methoxybenzophenone |
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