CA1113097A - Chemical modification of poly(bis-aryloxyphosphazene) with amines - Google Patents
Chemical modification of poly(bis-aryloxyphosphazene) with aminesInfo
- Publication number
- CA1113097A CA1113097A CA311,716A CA311716A CA1113097A CA 1113097 A CA1113097 A CA 1113097A CA 311716 A CA311716 A CA 311716A CA 1113097 A CA1113097 A CA 1113097A
- Authority
- CA
- Canada
- Prior art keywords
- amine
- polymer
- parts
- alkyl
- dihydro
- 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
- 150000001412 amines Chemical class 0.000 title claims description 43
- 238000007385 chemical modification Methods 0.000 title 1
- 229920002627 poly(phosphazenes) Polymers 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000002657 fibrous material Substances 0.000 claims abstract description 4
- 150000004989 p-phenylenediamines Chemical class 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 13
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 10
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 10
- -1 alkylaryl amine Chemical class 0.000 claims description 9
- 229920001971 elastomer Polymers 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000806 elastomer Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000000704 physical effect Effects 0.000 claims description 4
- DOFLWDGGNKBGSL-UHFFFAOYSA-N 6-dodecyl-2,2,4-trimethyl-1h-quinoline Chemical group N1C(C)(C)C=C(C)C2=CC(CCCCCCCCCCCC)=CC=C21 DOFLWDGGNKBGSL-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims 1
- 150000003975 aryl alkyl amines Chemical class 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 7
- ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical class C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920002632 poly(dichlorophosphazene) polymer Polymers 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- APTGHASZJUAUCP-UHFFFAOYSA-N 1-n,4-n-di(octan-2-yl)benzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(NC(C)CCCCCC)C=C1 APTGHASZJUAUCP-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- 229910019440 Mg(OH) Inorganic materials 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/025—Polyphosphazenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/844,018 US4130547A (en) | 1977-10-20 | 1977-10-20 | Chemical modification of poly(bis-aryloxyphosphazene) with amines |
| US844,018 | 1977-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113097A true CA1113097A (en) | 1981-11-24 |
Family
ID=25291565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA311,716A Expired CA1113097A (en) | 1977-10-20 | 1978-09-20 | Chemical modification of poly(bis-aryloxyphosphazene) with amines |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4130547A (enExample) |
| EP (1) | EP0001748B1 (enExample) |
| JP (1) | JPS5477700A (enExample) |
| AU (1) | AU527360B2 (enExample) |
| CA (1) | CA1113097A (enExample) |
| DE (1) | DE2861819D1 (enExample) |
| IT (1) | IT1113099B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495174A (en) * | 1982-06-21 | 1985-01-22 | Research Corporation | Anesthetic polyorganophosphazenes |
| US4440921A (en) * | 1982-06-21 | 1984-04-03 | Research Corporation | Coupling of polyorganophosphazenes to carboxylic acid |
| JPS6111016U (ja) * | 1984-06-26 | 1986-01-22 | 有限会社 後藤製鋲所 | 座金 |
| JPS61115088U (enExample) * | 1984-12-28 | 1986-07-21 | ||
| JPH05124672A (ja) * | 1991-06-25 | 1993-05-21 | Nikka Micron Kk | 液体供給装置 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1047052A (en) * | 1963-02-06 | 1966-11-02 | Hitachi Chemical Co Ltd | Process for treatment of polyphosphonitrile resinous substances |
| NL132242C (enExample) * | 1963-04-22 | |||
| AU6451674A (en) * | 1973-01-29 | 1975-07-31 | Fmc Corp | Phosphonitrilic chloride esters |
| US3856712A (en) * | 1973-06-11 | 1974-12-24 | Horizons Inc | Poly(alkoxyaryloxyphosphazene) elastomers |
| US3883451A (en) * | 1973-06-11 | 1975-05-13 | Horizons Inc | Flame-retardant poly (aryloxyphosphazene) copolymers |
| US3853794A (en) * | 1973-06-11 | 1974-12-10 | Horizons Inc | Alkylaryloxyphosphazene polymers |
| DE2439534A1 (de) * | 1974-08-17 | 1976-03-04 | Kabel Metallwerke Ghh | Verfahren zur aufbereitung und vernetzung von peroxidisch- und feuchtigkeitsvernetzbaren materialien |
| AU8222575A (en) * | 1974-06-20 | 1976-12-23 | Fmc Corp | Phosphonitrilic chloride esters |
| US3972841A (en) * | 1975-01-29 | 1976-08-03 | The Firestone Tire & Rubber Company | Polyphosphazene elastomer with up to 35 mole per cent non-fluorinated alkoxy groups having improved low temperature flexibility |
| US4053456A (en) * | 1976-02-27 | 1977-10-11 | Armstrong Cork Company | Poly(aryloxyphosphazene) copolymers |
| US4026838A (en) * | 1976-08-06 | 1977-05-31 | Armstrong Cork Company | Smoke-suppressant additives for polyphosphazenes |
| US4055523A (en) * | 1976-08-16 | 1977-10-25 | Armstrong Cork Company | Poly(dialkylaminoaryloxyphosphazene) polymers and foams |
| US4061606A (en) * | 1976-12-27 | 1977-12-06 | Armstrong Cork Company | Polyphosphazene polymer/organic polymer foams |
-
1977
- 1977-10-20 US US05/844,018 patent/US4130547A/en not_active Expired - Lifetime
-
1978
- 1978-09-20 CA CA311,716A patent/CA1113097A/en not_active Expired
- 1978-09-26 EP EP78100992A patent/EP0001748B1/en not_active Expired
- 1978-09-26 DE DE7878100992T patent/DE2861819D1/de not_active Expired
- 1978-10-11 IT IT28629/78A patent/IT1113099B/it active
- 1978-10-19 AU AU40876/78A patent/AU527360B2/en not_active Expired
- 1978-10-20 JP JP12995978A patent/JPS5477700A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0001748A1 (en) | 1979-05-16 |
| JPS5615819B2 (enExample) | 1981-04-13 |
| IT1113099B (it) | 1986-01-20 |
| IT7828629A0 (it) | 1978-10-11 |
| DE2861819D1 (en) | 1982-07-01 |
| AU527360B2 (en) | 1983-03-03 |
| EP0001748B1 (en) | 1982-05-12 |
| JPS5477700A (en) | 1979-06-21 |
| AU4087678A (en) | 1980-04-24 |
| US4130547A (en) | 1978-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |