GB743922A - Phosphate plasticizers - Google Patents
Phosphate plasticizersInfo
- Publication number
- GB743922A GB743922A GB10419/53A GB1041953A GB743922A GB 743922 A GB743922 A GB 743922A GB 10419/53 A GB10419/53 A GB 10419/53A GB 1041953 A GB1041953 A GB 1041953A GB 743922 A GB743922 A GB 743922A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cellulose
- dipropyl
- glycol
- bis
- alkylene
- 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
- 229910019142 PO4 Inorganic materials 0.000 title abstract 4
- 239000004014 plasticizer Substances 0.000 title abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title 1
- 239000010452 phosphate Substances 0.000 title 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 7
- -1 3-oxa-1,5-pentylene Chemical group 0.000 abstract 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 5
- 229920002678 cellulose Polymers 0.000 abstract 5
- MGWMBNBSQQGLAW-UHFFFAOYSA-N 1-[chloro(propoxy)phosphoryl]oxypropane Chemical compound CCCOP(Cl)(=O)OCCC MGWMBNBSQQGLAW-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 239000001913 cellulose Substances 0.000 abstract 4
- 235000021317 phosphate Nutrition 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 abstract 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract 2
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 239000012815 thermoplastic material Substances 0.000 abstract 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 abstract 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000001856 Ethyl cellulose Substances 0.000 abstract 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000020 Nitrocellulose Substances 0.000 abstract 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 abstract 1
- 239000002253 acid Substances 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
- HKQOBOMRSSHSTC-UHFFFAOYSA-N cellulose acetate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 HKQOBOMRSSHSTC-UHFFFAOYSA-N 0.000 abstract 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 abstract 1
- 229920001727 cellulose butyrate Polymers 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 229920006218 cellulose propionate Polymers 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 229920001249 ethyl cellulose Polymers 0.000 abstract 1
- 235000019325 ethyl cellulose Nutrition 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- 229920001220 nitrocellulos Polymers 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
-
- 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
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
A composition comprises a thermoplastic material, e.g. a derivative of cellulose, plasticized with a bis-dipropyl phosphate of an alkylene or mono-oxa-alkylene glycol, said glycol having 4 to 8 carbon atoms in the molecule (see Group IV (b)). The cellulose derivatives include cellulose esters such as cellulose nitrate cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetate-propionate and cellulose acetate butyrate as well as cellulose ethers such as ethyl cellulose and benzyl cellulose. Specified bis-dipropyl phosphates are those of 1,4 - butanediol, diethyleneglycol, 2,5 - hexanediol, and of dipropylene glycol. In examples plastic grade cellulose acetate is mixed with diethylene glycol-bis-dipropyl phosphate and butanediol-1,4-bis dipropyl phosphate respectively and pressed discs of good fire-resistance are prepared by moulding each mixture at 200 DEG C. for 15 minutes.ALSO:The invention comprises as new compounds bis-dipropyl phosphates of an alkylene or monooxa-alkylene glycol, said glycol having 4 to 8 carbon atoms in the molecule. Specified compounds are the dipropyl phosphates of 1,4-butanediol, diethylene glycol and 2,5-hexanediol and of dipropylene glycol. The products may be obtained by reacting 2 mols. of dipropyl chlorophosphate with one mol. of the glycol which may be tetramethylene; 3-oxa-1,5-pentylene; 3 - oxa - 1,5 - dimethyl - 1,5 - pentylene, hexamethylene; 2-ethyl hexamethylene; 2,2-diethyl trimethylene, or 5-oxa-1,7-heptylene, or diethylene glycol. The reaction is preferably carried out in the presence of an acid acceptor and mutual solvent such as pyridine. Examples describe the production of diethylene glycol bis-dipropyl phosphate and butanediol - 1,4 - bis-dipropyl phosphate by reacting the corresponding glycol with dipropylchlorophosphate in the presence of pyridine. The dipropyl chlorophosphate used is prepared by adding phosphorus trichloride gradually to n-propyl alcohol maintained at 8-11 DEG C. and then chlorinating by introducing chlorine under reduced pressure at 8-10 DEG C. until the reaction mixture turns yellow and a temperature drop is noted. Residual HCl is then removed and the product is then distilled under reduced pressure to yield dipropyl-chlorophosphate. The alkylene glycol phosphates are stated to be suitable as plasticizers for thermoplastic material particularly cellulose derivatives (see Group IV (a)).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US743922XA | 1952-04-16 | 1952-04-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB743922A true GB743922A (en) | 1956-01-25 |
Family
ID=22119308
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10419/53A Expired GB743922A (en) | 1952-04-16 | 1953-04-16 | Phosphate plasticizers |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB743922A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3180847A (en) * | 1960-11-21 | 1965-04-27 | Union Carbide Corp | Polymeric organophosphonite stabilized halogen-containing vinyl resin solutions |
US3255634A (en) * | 1961-11-14 | 1966-06-14 | Siderurgie Fse Inst Rech | Method of and apparatus for withdrawing samples from molten metal baths |
US4343732A (en) | 1979-10-24 | 1982-08-10 | Ajinomoto Company Incorporated | Stabilized halogen-containing resin compositions |
-
1953
- 1953-04-16 GB GB10419/53A patent/GB743922A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3180847A (en) * | 1960-11-21 | 1965-04-27 | Union Carbide Corp | Polymeric organophosphonite stabilized halogen-containing vinyl resin solutions |
US3255634A (en) * | 1961-11-14 | 1966-06-14 | Siderurgie Fse Inst Rech | Method of and apparatus for withdrawing samples from molten metal baths |
US4343732A (en) | 1979-10-24 | 1982-08-10 | Ajinomoto Company Incorporated | Stabilized halogen-containing resin compositions |
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