CA1038596A - Metal 8-hydroxyquinolate complexes as stabilizers for poly(phosphazenes) to inhibit thermal degradation at elevated temperatures - Google Patents
Metal 8-hydroxyquinolate complexes as stabilizers for poly(phosphazenes) to inhibit thermal degradation at elevated temperaturesInfo
- Publication number
- CA1038596A CA1038596A CA207,888A CA207888A CA1038596A CA 1038596 A CA1038596 A CA 1038596A CA 207888 A CA207888 A CA 207888A CA 1038596 A CA1038596 A CA 1038596A
- Authority
- CA
- Canada
- Prior art keywords
- hrs
- metal
- polyphosphazene
- poly
- thermal degradation
- 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
- 229920002627 poly(phosphazenes) Polymers 0.000 title claims abstract description 24
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 16
- 239000002184 metal Substances 0.000 title claims abstract description 16
- 230000015556 catabolic process Effects 0.000 title claims abstract description 8
- 238000006731 degradation reaction Methods 0.000 title claims abstract description 8
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical class C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 title abstract description 9
- 239000003381 stabilizer Substances 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 3
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 238000003878 thermal aging Methods 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 abstract description 5
- 238000011105 stabilization Methods 0.000 abstract description 5
- 238000010348 incorporation Methods 0.000 abstract description 3
- 150000002739 metals Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000007689 inspection Methods 0.000 description 6
- 230000035882 stress Effects 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 150000004659 dithiocarbamates Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 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 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 229910002019 Aerosil® 380 Inorganic materials 0.000 description 1
- 241001378740 Mugil liza Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010042209 Stress Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910001038 basic metal oxide Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- 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
- C07F9/062—Organo-phosphoranes without P-C bonds
- C07F9/065—Phosphoranes containing the structure P=N-
- C07F9/067—Polyphosphazenes containing the structure [P=N-n]
-
- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US401769A US3867341A (en) | 1973-09-28 | 1973-09-28 | Metal 8-hydroxyquinolate complexes as stabilizers for poly(phosphazenes) to inhibit thermal degradation at elevated temperatures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038596A true CA1038596A (en) | 1978-09-19 |
Family
ID=23589159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA207,888A Expired CA1038596A (en) | 1973-09-28 | 1974-08-27 | Metal 8-hydroxyquinolate complexes as stabilizers for poly(phosphazenes) to inhibit thermal degradation at elevated temperatures |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3867341A (enExample) |
| JP (1) | JPS5425550B2 (enExample) |
| BE (1) | BE820498A (enExample) |
| CA (1) | CA1038596A (enExample) |
| DE (1) | DE2445607C3 (enExample) |
| FR (1) | FR2245731B1 (enExample) |
| GB (1) | GB1478471A (enExample) |
| IT (1) | IT1022383B (enExample) |
| NL (1) | NL177028C (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017458A (en) * | 1976-02-26 | 1977-04-12 | The Firestone Tire & Rubber Company | Stabilization of poly(phosphazenes) |
| US4116785A (en) * | 1976-02-27 | 1978-09-26 | The Firestone Tire & Rubber Company | Phosphonitrilic polymers with curability by sulfur accelerated cures or radiation cures |
| US4051103A (en) * | 1977-02-23 | 1977-09-27 | The Firestone Tire & Rubber Company | Stabilization of polyfluorophosphazenes with zinc hippurate |
| US4101507A (en) * | 1977-03-21 | 1978-07-18 | The Firestone Tire & Rubber Company | Stabilization of polyphosphazenes |
| US4120838A (en) * | 1977-08-01 | 1978-10-17 | The Firestone Tire & Rubber Company | Polyphosphazene wire coverings |
| US4139523A (en) * | 1978-04-28 | 1979-02-13 | The Firestone Tire & Rubber Company | Stabilization of polyphosphazene vulcanizates with a metal complex |
| US5104602A (en) * | 1989-12-15 | 1992-04-14 | Eastman Kodak Company | Method of forming fibers of blends of etheric phosphazene polymers and metal oxides |
| US5190819A (en) * | 1989-12-15 | 1993-03-02 | Eastman Kodak Company | Fibers formed of blends of etheric phosphazene polymers and metal oxides and the method of their formation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2586312A (en) * | 1948-02-04 | 1952-02-19 | Goldschmidt Frieda | Polyphosphonitrilic esters and their preparation |
| US3272773A (en) * | 1962-10-01 | 1966-09-13 | Du Pont | Process of producing stabilized polycarbonamides containing a metal chelate of 8-hydroxyquinoline |
| US3515688A (en) * | 1967-08-30 | 1970-06-02 | Horizons Research Inc | Extreme service phosphonitrile elastomers |
| US3474052A (en) * | 1968-04-24 | 1969-10-21 | Firestone Tire & Rubber Co | Rubber stabilized with phosphonitrilic compounds |
| NL169888C (nl) * | 1971-03-26 | Firestone Tire & Rubber Co | Werkwijze voor de bereiding van fosfazeen elastomeren en kunststoffen. | |
| US3766157A (en) * | 1972-12-29 | 1973-10-16 | Monsanto Res Corp | Smoke retardant styrene polymer compositions |
-
1973
- 1973-09-28 US US401769A patent/US3867341A/en not_active Expired - Lifetime
-
1974
- 1974-08-27 CA CA207,888A patent/CA1038596A/en not_active Expired
- 1974-09-11 NL NLAANVRAGE7412049,A patent/NL177028C/xx not_active IP Right Cessation
- 1974-09-24 DE DE2445607A patent/DE2445607C3/de not_active Expired
- 1974-09-27 FR FR7432662A patent/FR2245731B1/fr not_active Expired
- 1974-09-27 JP JP11132774A patent/JPS5425550B2/ja not_active Expired
- 1974-09-27 BE BE149037A patent/BE820498A/xx not_active IP Right Cessation
- 1974-09-27 GB GB4217174A patent/GB1478471A/en not_active Expired
- 1974-09-27 IT IT27794/74A patent/IT1022383B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5425550B2 (enExample) | 1979-08-29 |
| NL177028C (nl) | 1985-07-16 |
| DE2445607A1 (de) | 1975-04-03 |
| FR2245731A1 (enExample) | 1975-04-25 |
| NL7412049A (nl) | 1975-04-02 |
| IT1022383B (it) | 1978-03-20 |
| GB1478471A (en) | 1977-06-29 |
| NL177028B (nl) | 1985-02-18 |
| DE2445607C3 (de) | 1981-03-12 |
| US3867341A (en) | 1975-02-18 |
| DE2445607B2 (de) | 1980-07-31 |
| FR2245731B1 (enExample) | 1978-11-24 |
| AU7307574A (en) | 1976-03-11 |
| BE820498A (fr) | 1975-01-16 |
| JPS5061451A (enExample) | 1975-05-27 |
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