GB1036578A - Tertiary amine salts of phosphoric acid esters - Google Patents
Tertiary amine salts of phosphoric acid estersInfo
- Publication number
- GB1036578A GB1036578A GB3479464A GB3479464A GB1036578A GB 1036578 A GB1036578 A GB 1036578A GB 3479464 A GB3479464 A GB 3479464A GB 3479464 A GB3479464 A GB 3479464A GB 1036578 A GB1036578 A GB 1036578A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- alkyl group
- phosphate
- octadecyldimethylammonium
- group
- 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
- -1 Tertiary amine salts Chemical class 0.000 title abstract 4
- 150000003014 phosphoric acid esters Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000004698 Polyethylene Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000010348 incorporation Methods 0.000 abstract 2
- 229920000573 polyethylene Polymers 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 229920003002 synthetic resin Polymers 0.000 abstract 2
- 239000000057 synthetic resin Substances 0.000 abstract 2
- GAJQCIFYLSXSEZ-UHFFFAOYSA-L tridecyl phosphate Chemical compound CCCCCCCCCCCCCOP([O-])([O-])=O GAJQCIFYLSXSEZ-UHFFFAOYSA-L 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000002216 antistatic agent Substances 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical class CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 abstract 1
- UICHMASMHUXHBX-UHFFFAOYSA-N dimethyl(octadecyl)azanium;ditridecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCN(C)C.CCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCC UICHMASMHUXHBX-UHFFFAOYSA-N 0.000 abstract 1
- FDMGVDAGBSCTGR-UHFFFAOYSA-N dimethyl(octadecyl)azanium;tridecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCOP(O)(O)=O.CCCCCCCCCCCCCCCCCCN(C)C FDMGVDAGBSCTGR-UHFFFAOYSA-N 0.000 abstract 1
- XEJNLUBEFCNORG-UHFFFAOYSA-N ditridecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCC XEJNLUBEFCNORG-UHFFFAOYSA-N 0.000 abstract 1
- IEBSXEIXFUJYNQ-UHFFFAOYSA-N dodecyl(dimethyl)azanium ethyl phosphate Chemical compound P(=O)(OCC)([O-])[O-].C(CCCCCCCCCCC)[NH+](C)C.C(CCCCCCCCCCC)[NH+](C)C IEBSXEIXFUJYNQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1657—Compounds containing the structure P(=X)n-X-N (X = O, S, Se; n = 0, 1)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention comprises compounds of the formula <F\1> wherein R is hydrogen, an alkyl group of up to 18 carbon atoms, a monoalkylphenyl group of 4 to 12 carbon atoms in the alkyl group or substituents of the formula <F\2> R1 is an alkyl group of up to 18 carbon atoms or a monoalkylphenyl group of from 4 to 12 carbon atoms in the alkyl group, R2 and R4 are each alkyl groups of up to 18 carbon atoms and R3 and R5 are each alkyl groups of 12 to 18 carbon atoms. They may be prepared by reacting mono- or diethyl phosphates with a tertiary amine at an elevated temperature, e.g. 50 DEG C., and are useful as antistatic agents particularly for synthetic resins (see Division C3).ALSO:Synthetic resins, particularly polyethylene, may be rendered antistatic by uniformly dispersing therein from 0.01% to 10% by weight of a compound having the formula <FORM:1036578/C3/1> wherein R is hydrogen, an alkyl group of up to 18 carbon atoms, a monoalkylphenyl group having 4 to 12 carbon atoms in the alkyl group or substituents of the formula <FORM:1036578/C3/2> R1 is an alkyl group of up to 18 carbon atoms or a monoalkylphenyl group of 4 to 12 carbon atoms in the alkyl group, R2 and R4 are each alkyl groups of up to 18 carbon atoms and R3 and R5 are each alkyl groups of from 12 to 18 carbon atoms. Examples describe the incorporation of an equimolar mixture of octadecyldimethylammonium di(tridecy)phosphate and bis(octadecyldimethylammonium)tridecyl phosphate or an equimolar mixture of octadecyldimethylammonium di(tridecyl)phosphate and octadecyldimethylammonium hydrogen tridecyl phosphate or dodecyldimethylammonium ethyl phosphate (mixed mono- and diesters) into polyethylene suitably in pellet form and the incorporation of an equimolar mixture of octadecyldimethylammoniu di(tridecyl)phosphate and octadecyldimethylammonium hydrogen tridecylphosphate into an n-octyl, decyl trimellitate plasticizer used in the manufacture of polyvinyl chloride.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30494763A | 1963-08-27 | 1963-08-27 | |
| US385269A US3364192A (en) | 1964-07-27 | 1964-07-27 | Antistatic polymer compositions containing ammonium phosphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1036578A true GB1036578A (en) | 1966-07-20 |
Family
ID=26974320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3479464A Expired GB1036578A (en) | 1963-08-27 | 1964-08-25 | Tertiary amine salts of phosphoric acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1036578A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2131029A (en) * | 1982-11-19 | 1984-06-13 | Chemmar Associates Inc | Sanitizing of organic polymers |
| US4608289A (en) * | 1983-08-16 | 1986-08-26 | Interface Research Corporation | Carpet containing sanitizing compounds and methods |
| US4647601A (en) * | 1984-03-08 | 1987-03-03 | Interface Research Corporation | Self-sanitizing epoxy resins and preparation thereof |
| US4908209A (en) | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
| US4935232A (en) | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
| US4957948A (en) | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
| US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
| US5032310A (en) | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
| US5474739A (en) | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
| US5639464A (en) | 1988-05-05 | 1997-06-17 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
-
1964
- 1964-08-25 GB GB3479464A patent/GB1036578A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5474739A (en) | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
| GB2131029A (en) * | 1982-11-19 | 1984-06-13 | Chemmar Associates Inc | Sanitizing of organic polymers |
| DE3248708A1 (en) * | 1982-11-19 | 1984-07-05 | Chemmar Associates, Inc., Greensboro, N.C. | PRODUCT WITH ANTI-DISEASE PROPERTIES AND USE OF AN ANTI-GROWTH COMPOUND FOR PRODUCING THE PRODUCT |
| AU567484B2 (en) * | 1982-11-19 | 1987-11-26 | Interface Research Corporation | Quarternary ammonium phosphate salts incorporated into carpets as sanitizing agent. |
| US4608289A (en) * | 1983-08-16 | 1986-08-26 | Interface Research Corporation | Carpet containing sanitizing compounds and methods |
| US4908209A (en) | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
| US4935232A (en) | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
| US5032310A (en) | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
| US4647601A (en) * | 1984-03-08 | 1987-03-03 | Interface Research Corporation | Self-sanitizing epoxy resins and preparation thereof |
| US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
| US4957948A (en) | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
| US5639464A (en) | 1988-05-05 | 1997-06-17 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
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