CA1111994A - Poly(organophosphagenes) avec chromophores comme groupes de substitution - Google Patents

Poly(organophosphagenes) avec chromophores comme groupes de substitution

Info

Publication number: CA1111994A
Authority: CA; Canada
Prior art keywords: group; compound; yellow; methylamino; ethoxy
Prior art date: 1977-05-12
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

Application number

CA303,161A

Other languages

English (en)

Inventor

Harry R. Allcock

Sarah D. Wright

Karen M. Kosydar

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bridgestone Firestone Inc

Original Assignee

Firestone Tire and Rubber Co

Priority date (The priority date 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 date listed.)

1977-05-12

Filing date

1978-05-11

Publication date

1981-11-03

1978-05-11 Application filed by Firestone Tire and Rubber Co filed Critical Firestone Tire and Rubber Co

1979-07-26 Priority claimed from US06/061,140 external-priority patent/US4282711A/en

1981-11-03 Application granted granted Critical

1981-11-03 Publication of CA1111994A publication Critical patent/CA1111994A/fr

Status Expired legal-status Critical Current

Links

125000001424 substituent group Chemical group 0.000 title abstract description 20
238000000034 method Methods 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 5
-1 azo nitro, ketone amine Chemical class 0.000 claims description 58
150000001875 compounds Chemical class 0.000 claims description 56
125000000962 organic group Chemical group 0.000 claims description 14
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 13
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 claims description 7
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 6
235000019233 fast yellow AB Nutrition 0.000 claims description 6
WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 claims description 5
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 4
GYOOLBZBEMIASI-UHFFFAOYSA-N 5-hydroxy-1,4-bis(4-methylanilino)anthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC(O)=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 GYOOLBZBEMIASI-UHFFFAOYSA-N 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical group C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 claims description 4
AZOPGDOIOXKJRA-UHFFFAOYSA-L chembl1817788 Chemical compound [Na+].[Na+].C1=C(C([O-])=O)C(O)=CC=C1N=NC1=CC=C(C=2C=CC(=CC=2)N=NC=2C=C(C(O)=CC=2)C([O-])=O)C=C1 AZOPGDOIOXKJRA-UHFFFAOYSA-L 0.000 claims description 4
BBWPEJUNPNPWJI-UHFFFAOYSA-L disodium 3-[(4-aminophenyl)diazenyl]-4,5-dihydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].NC1=CC=C(C=C1)N=NC=1C(=CC2=CC(=CC(=C2C=1O)O)S(=O)(=O)[O-])S(=O)(=O)[O-] BBWPEJUNPNPWJI-UHFFFAOYSA-L 0.000 claims description 4
ADAUKUOAOMLVSN-UHFFFAOYSA-N gallocyanin Chemical compound [Cl-].OC(=O)C1=CC(O)=C(O)C2=[O+]C3=CC(N(C)C)=CC=C3N=C21 ADAUKUOAOMLVSN-UHFFFAOYSA-N 0.000 claims description 4
WOTPFVNWMLFMFW-ISLYRVAYSA-N para red Chemical compound OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=C(N(=O)=O)C=C1 WOTPFVNWMLFMFW-ISLYRVAYSA-N 0.000 claims description 4
AZLXCBPKSXFMET-UHFFFAOYSA-M sodium 4-[(4-sulfophenyl)diazenyl]naphthalen-1-olate Chemical compound [Na+].C12=CC=CC=C2C(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 AZLXCBPKSXFMET-UHFFFAOYSA-M 0.000 claims description 4
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical group Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 claims description 3
WDVSHHCDHLJJJR-UHFFFAOYSA-N Proflavine Chemical compound C1=CC(N)=CC2=NC3=CC(N)=CC=C3C=C21 WDVSHHCDHLJJJR-UHFFFAOYSA-N 0.000 claims description 3
KLCDQSGLLRINHY-VHEBQXMUSA-N Yellow AB Chemical compound NC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=CC=C1 KLCDQSGLLRINHY-VHEBQXMUSA-N 0.000 claims description 3
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
150000004056 anthraquinones Chemical class 0.000 claims description 3
239000000987 azo dye Substances 0.000 claims description 3
VVAVKBBTPWYADW-RVTJCSDESA-L biebrich scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=CC=CC2=C1\N=N\C(C(=C1)S([O-])(=O)=O)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 VVAVKBBTPWYADW-RVTJCSDESA-L 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 claims description 3
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 3
229960000286 proflavine Drugs 0.000 claims description 3
125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000004986 diarylamino group Chemical group 0.000 claims description 2
239000000999 acridine dye Substances 0.000 claims 2
239000001000 anthraquinone dye Substances 0.000 claims 2
239000001005 nitro dye Substances 0.000 claims 2
239000000988 sulfur dye Substances 0.000 claims 2
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims 2
101100379067 Caenorhabditis elegans anc-1 gene Proteins 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000005248 alkyl aryloxy group Chemical group 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
229920000642 polymer Polymers 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
239000000460 chlorine Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000975 dye Substances 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000001556 precipitation Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000004132 cross linking Methods 0.000 description 7
239000012467 final product Substances 0.000 description 7
229920002632 poly(dichlorophosphazene) polymer Polymers 0.000 description 7
239000000376 reactant Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
239000000835 fiber Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
229920002627 poly(phosphazenes) Polymers 0.000 description 5
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 5
229940043267 rhodamine b Drugs 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
238000000502 dialysis Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000006309 butyl amino group Chemical group 0.000 description 3
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
239000000576 food coloring agent Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000010669 acid-base reaction Methods 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
IMNRJGSQCGFPHL-UHFFFAOYSA-N benzene;oxolane Chemical compound C1CCOC1.C1=CC=CC=C1 IMNRJGSQCGFPHL-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
238000005266 casting Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002955 isolation Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
229940051142 metanil yellow Drugs 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000000178 monomer Substances 0.000 description 2
229920000307 polymer substrate Polymers 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical compound [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
229920003169 water-soluble polymer Polymers 0.000 description 2
UPMAOXLCTXPPAG-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ol Chemical compound C1CCCC2CC(O)CCC21 UPMAOXLCTXPPAG-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UUHXCOGOBLTVJX-UHFFFAOYSA-N 1-cyclohexyl-2-phenylhydrazine Chemical compound C1CCCCC1NNC1=CC=CC=C1 UUHXCOGOBLTVJX-UHFFFAOYSA-N 0.000 description 1
KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 1
BYKNGMLDSIEFFG-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F BYKNGMLDSIEFFG-UHFFFAOYSA-N 0.000 description 1
NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
UPUDZFFFZRSNAE-UHFFFAOYSA-N 9-(4-aminophenyl)acridin-3-amine Chemical compound C1=CC(N)=CC=C1C1=C(C=CC=C2)C2=NC2=CC(N)=CC=C12 UPUDZFFFZRSNAE-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
229950011260 betanaphthol Drugs 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
150000003940 butylamines Chemical class 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
ZLFVRXUOSPRRKQ-UHFFFAOYSA-N chembl2138372 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-UHFFFAOYSA-N 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000010408 film Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
150000008040 ionic compounds Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000010494 opalescence Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012430 organic reaction media Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
238000010094 polymer processing Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000979 synthetic dye Substances 0.000 description 1
239000001040 synthetic pigment Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000006250 trifluoro ethyl amino group Chemical group [H]N(*)C([H])([H])C(F)(F)F 0.000 description 1

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Luminescent Compositions (AREA)

CA303,161A 1977-05-12 1978-05-11 Poly(organophosphagenes) avec chromophores comme groupes de substitution Expired CA1111994A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US79607377A	1977-05-12	1977-05-12
US796,073		1977-05-12
US06/061,140 US4282711A (en)	1979-07-26	1979-07-26	Hydrostatic transmission control system
US061,140		1979-07-27

Publications (1)

Publication Number	Publication Date
CA1111994A true CA1111994A (fr)	1981-11-03

Family

ID=26740768

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,161A Expired CA1111994A (fr)	1977-05-12	1978-05-11	Poly(organophosphagenes) avec chromophores comme groupes de substitution

Country Status (1)

Country	Link
CA (1)	CA1111994A (fr)

1978
- 1978-05-11 CA CA303,161A patent/CA1111994A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-11-03	MKEX	Expiry

Publication	Publication Date	Title
US4242499A (en)	1980-12-30	Colored polymers comprising poly(organophosphazenes) with chromophores as substituent groups
Allcock	1977	Poly (organophosphazenes)—Unusual new high polymers
Allcock et al.	1966	Phosphonitrilic compounds. VI. High molecular weight poly (alkoxy-and aryloxyphosphazenes)
Allcock et al.	1981	Diazo coupling reactions with poly (organophosphazenes)
Ni et al.	1996	Polymers with sulfur (VI)− nitrogen− phosphorus backbones: synthesis, characterization, and properties of atactic poly [(amino) thionylphosphazenes]
GB1597698A (en)	1981-09-09	Poly (organophosphazenes) with chromophores as substituent groups
CA1111994A (fr)	1981-11-03	Poly(organophosphagenes) avec chromophores comme groupes de substitution
US4412066A (en)	1983-10-25	Polymer bound dyes prepared by diazo coupling reactions with poly(organophosphazenes)
White et al.	1975	Synthesis of polyarylaminophosphazenes
Pelter et al.	1990	Thermal rigidification of polyquinolines by thermolytic elimination of ethylene from a 9, 10-dihydro-9, 10-ethanoanthracene unit
Allcock et al.	1978	Poly (organophosphazenes) with chromophores as substituent groups
US3896058A (en)	1975-07-22	Polyphosphazenes containing the cf' 3'chfcf' 2'ch' 2'o-group
US4218556A (en)	1980-08-19	Polyphosphazene copolymers containing tetraalkyl orthosilicate substituents and a process therefore
SU1085993A1 (ru)	1984-04-15	Способ получени гидрофильных полиорганофосфазенов
Gleria et al.	1992	Photochemical behavior of poly (organophosphazenes). X. Photo-cross-linking phenomena in poly [bis (4-isopropylphenoxy) 0.8 (4-benzoylphenoxy) 1.2 phosphazene]
EP0013695B1 (fr)	1982-06-23	Polymères de polyphosphazène contenant des substituants cétal cycliques et procédé pour leur préparation
EP0369398B1 (fr)	1995-09-06	Dérivés de polyphosphazène contenant des groupes carbonyliques aptes aux procédés de photoréticulation
CA1260192A (fr)	1989-09-26	Derives de substitution diallylamines de polyphosphazene
US3563950A (en)	1971-02-16	Linear polybenzoxazoles
Facchin et al.	1999	Thermosetting resins and azo dyes based on phosphazenes
Fewell et al.	1983	Synthesis and thermal stability of carborane‐containing phosphazenes
US4223103A (en)	1980-09-16	Polyphosphazene polymers containing substituents derived from thienyl alcohols
EP0014232B1 (fr)	1982-12-15	Polymères de polyphosphazène contenant des substituants dérivés de cétoximes et procédé pour leur préparation
EP0200854A2 (fr)	1986-12-17	Homopolymères et copolymères de phosphazène ayant des dérivés hydroxy ou amino de carbazole ou de naphtalène comme substituants
Dyer et al.	1970	Phosphorus‐containing polyurethans