GB628477A - Improvements in compositions containing cellulose esters and ethers - Google Patents
Improvements in compositions containing cellulose esters and ethersInfo
- Publication number
- GB628477A GB628477A GB27430/46A GB2743046A GB628477A GB 628477 A GB628477 A GB 628477A GB 27430/46 A GB27430/46 A GB 27430/46A GB 2743046 A GB2743046 A GB 2743046A GB 628477 A GB628477 A GB 628477A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tri
- phosphate
- meta
- chloro
- phosphoric acid
- 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
- 229920002678 cellulose Polymers 0.000 title abstract 5
- 239000000203 mixture Substances 0.000 title abstract 5
- 229920003086 cellulose ether Polymers 0.000 title abstract 3
- 150000002170 ethers Chemical class 0.000 title abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 8
- 239000010452 phosphate Substances 0.000 abstract 8
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 238000007689 inspection Methods 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 abstract 1
- SZPWGEZWBLCYCZ-UHFFFAOYSA-N 3,4-dichloro-2-methylphenol Chemical class CC1=C(O)C=CC(Cl)=C1Cl SZPWGEZWBLCYCZ-UHFFFAOYSA-N 0.000 abstract 1
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 abstract 1
- ZQLMXRADIUUOFT-UHFFFAOYSA-N 4,5-dichloro-1,6-dimethylcyclohexa-2,4-dien-1-ol Chemical class ClC1=C(C(C(C=C1)(C)O)C)Cl ZQLMXRADIUUOFT-UHFFFAOYSA-N 0.000 abstract 1
- OJFZXRZZXBFEAP-UHFFFAOYSA-N 5-chloro-1,6-dimethylcyclohexa-2,4-dien-1-ol Chemical class ClC=1C(C(C=CC1)(C)O)C OJFZXRZZXBFEAP-UHFFFAOYSA-N 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 abstract 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 abstract 1
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 abstract 1
- 229940081735 acetylcellulose Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 abstract 1
- 239000001527 calcium lactate Substances 0.000 abstract 1
- 229960002401 calcium lactate Drugs 0.000 abstract 1
- 235000011086 calcium lactate Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- YLVNGRUHVMFTDN-UHFFFAOYSA-N tris(4-chloro-3-methylphenyl) phosphate Chemical compound C1=C(Cl)C(C)=CC(OP(=O)(OC=2C=C(C)C(Cl)=CC=2)OC=2C=C(C)C(Cl)=CC=2)=C1 YLVNGRUHVMFTDN-UHFFFAOYSA-N 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
A composition of matter having a basis of a cellulose ester or ether and containing as a softener or plasticizer, a halogenated organic phosphoric acid ester other than tri-parachlorphenyl phosphate of the general formula <FORM:0628477/IV (a)/1> wherein R represents an alkyl group, X is halogen, n is 0, 1 or 2, and m is an integer of at least 1, said compounds having a meta- and/or para-halogen substituent. The cellulose derivative may be cellulose-acetate, lactate, nitrate, propionate, butyrate, acetate-propionate, and acetate-butyrate or ethyl or benzyl cellulose. Stabilizers such as calcium lactate may be incorporated in the compositions. In examples 1, 2 and 3, tri-(2 p : 4-dichlorophenyl)-, tri-(4-chloro-meta cresyl)- and tri-(4-chloro-2 : 3-dimethylphenyl)-phosphate are mixed with cellulose esters and ethers. U.S.A. Specification 1,985,771 is referred to. The Specification as open to inspection under Sect. 91 includes the use of tri-parachlorphenyl phosphate for the above purpose. It also states that the above phosphoric acid esters including tri-parachlorphenyl phosphate are useful as plasticizers in plastic compositions containing synthetic resins, and also as softeners and modifiers for synthetic rubber and for polymeric compounds such as polyvinyl chloride and copolymers of vinyl chloride and vinyl acetate. This subject-matter does not appear in the Specification as accepted. Reference has been directed by the Comptroller to U.S.A. Specification 1,985,771.ALSO:Phosphoric acid esters of the general formula (other than tri-parachlorphenyl phosphate) <FORM:0628477/IV (b)/1> wherein R represents an alkyl group such as methyl, ethyl, propyl, butyl, isobutyl, tertiary butyl or amyl, X represents a halogen, n is 0, 1 or 2 and m is an integer of at least 1, said compounds having a meta- and/or para-halogen substituent, are prepared by reacting a phosphorus oxyhalide, e.g. phosphorus oxychloride, with a phenol containing a meta- and/or parahalogen substituent at an elevated temperature. The phenyl group may also contain a halogen in the ortho position. The reaction may be effected in the presence of a catalyst, e.g., in the presence of anhydrous magnesium chloride at a temperature not exceeding 225 DEG C. Suitable phenols mentioned are 4-chloro-meta-cresol, chloro-xylenols, dichloro-phenols, dichlorocresols, or dichloro-xylenols containing chlorine in the meta and/or para position. Mixtures of the suitable phenols may also be used to form a complex phosphoric acid ester. In examples 1, 2 and 3, the following phosphoric acid esters are prepared: tri-(2 : 4-dichlorophenyl)-phosphate, tri-(4-chloro-meta-cresyl)-phosphate and tri-(4-chloro-2 : 3-dimethyl-phenyl)-phosphate. U.S.A. Specification 1,985,771 is referred to. The Specification as open to inspection under Sect. 91 refers to the preparation of tri-parachloro-phenyl phosphate by the above method. This subject-matter does not appear in the Specification as accepted. Reference has been directed by the Comptroller to U.S.A. Specification 1,985,771.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US628477XA | 1945-09-13 | 1945-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB628477A true GB628477A (en) | 1949-08-30 |
Family
ID=22045228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27430/46A Expired GB628477A (en) | 1945-09-13 | 1946-09-12 | Improvements in compositions containing cellulose esters and ethers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB628477A (en) |
-
1946
- 1946-09-12 GB GB27430/46A patent/GB628477A/en not_active Expired
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