CA1044639A - Reactions et catalyseurs photosensibilisants, lies a des polymeres - Google Patents

Reactions et catalyseurs photosensibilisants, lies a des polymeres

Info

Publication number: CA1044639A
Authority: CA; Canada
Prior art keywords: polymer; photosensitizing; bound; catalyst; reaction
Prior art date: 1974-06-12
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

CA219,037A

Other languages

English (en)

Other versions

CA219037S (en

Inventor

Erich C. Blossey

Douglas C. Neckers

A. Paul Schaap

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.)

Research Corp

Original Assignee

Research Corp

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.)

1974-06-12

Filing date

1975-01-30

Publication date

1978-12-19

1975-01-30 Application filed by Research Corp filed Critical Research Corp

1978-07-07 Priority to CA306,979A priority Critical patent/CA1054971A/fr

1978-12-19 Application granted granted Critical

1978-12-19 Publication of CA1044639A publication Critical patent/CA1044639A/fr

Status Expired legal-status Critical Current

Links

239000003504 photosensitizing agent Substances 0.000 title claims abstract description 91
230000002165 photosensitisation Effects 0.000 title claims abstract description 63
229920000642 polymer Polymers 0.000 title claims abstract description 62
239000003054 catalyst Substances 0.000 title claims abstract description 53
238000005950 photosensitized reaction Methods 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims abstract description 54
150000001875 compounds Chemical class 0.000 claims abstract description 26
239000000463 material Substances 0.000 claims abstract description 22
238000006073 displacement reaction Methods 0.000 claims abstract description 18
230000000269 nucleophilic effect Effects 0.000 claims abstract description 18
230000003197 catalytic effect Effects 0.000 claims abstract description 17
239000012038 nucleophile Substances 0.000 claims abstract description 17
206010034972 Photosensitivity reaction Diseases 0.000 claims abstract description 11
239000007795 chemical reaction product Substances 0.000 claims abstract description 9
238000007210 heterogeneous catalysis Methods 0.000 claims abstract description 9
239000012434 nucleophilic reagent Substances 0.000 claims abstract description 7
IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 claims description 16
-1 hematoporphytin Chemical compound 0.000 claims description 16
229930187593 rose bengal Natural products 0.000 claims description 16
229940081623 rose bengal Drugs 0.000 claims description 16
STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
239000011324 bead Substances 0.000 claims description 14
239000004793 Polystyrene Substances 0.000 claims description 9
229920001577 copolymer Polymers 0.000 claims description 9
229920002223 polystyrene Polymers 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
150000007942 carboxylates Chemical group 0.000 claims description 6
239000013078 crystal Substances 0.000 claims description 5
GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 5
DPKHZNPWBDQZCN-UHFFFAOYSA-N acridine orange free base Chemical compound C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 DPKHZNPWBDQZCN-UHFFFAOYSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 claims description 4
229940013640 flavin mononucleotide Drugs 0.000 claims description 4
FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 claims description 4
FVTCRASFADXXNN-UHFFFAOYSA-N flavin mononucleotide Natural products OP(=O)(O)OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-UHFFFAOYSA-N 0.000 claims description 4
239000011768 flavin mononucleotide Substances 0.000 claims description 4
229940025294 hemin Drugs 0.000 claims description 4
BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 claims description 4
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FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 claims description 4
229960000907 methylthioninium chloride Drugs 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
235000019231 riboflavin-5'-phosphate Nutrition 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 3
229930002875 chlorophyll Natural products 0.000 claims description 3
235000019804 chlorophyll Nutrition 0.000 claims description 3
ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 3
229940099898 chlorophyllin Drugs 0.000 claims description 3
235000019805 chlorophyllin Nutrition 0.000 claims description 3
YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 claims description 3
229910052751 metal Chemical group 0.000 claims description 3
239000002184 metal Chemical group 0.000 claims description 3
YYGBVRCTHASBKD-UHFFFAOYSA-M methylene green Chemical compound [Cl-].C1=CC(N(C)C)=C([N+]([O-])=O)C2=[S+]C3=CC(N(C)C)=CC=C3N=C21 YYGBVRCTHASBKD-UHFFFAOYSA-M 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
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 claims description 3
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 3
UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical compound CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 claims description 2
229960002143 fluorescein Drugs 0.000 claims description 2
229960003569 hematoporphyrin Drugs 0.000 claims description 2
229950003937 tolonium Drugs 0.000 claims description 2
HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 claims description 2
150000003440 styrenes Chemical class 0.000 claims 5
229940106705 chlorophyll Drugs 0.000 claims 2
125000004663 dialkyl amino group Chemical group 0.000 claims 2
IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 claims 2
CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 claims 2
229940043267 rhodamine b Drugs 0.000 claims 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
229920001328 Polyvinylidene chloride Polymers 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
239000005033 polyvinylidene chloride Substances 0.000 claims 1
238000007539 photo-oxidation reaction Methods 0.000 abstract description 27
239000012429 reaction media Substances 0.000 abstract description 8
238000001914 filtration Methods 0.000 abstract description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 28
239000000975 dye Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
239000000758 substrate Substances 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
229910052760 oxygen Inorganic materials 0.000 description 10
239000001301 oxygen Substances 0.000 description 10
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 8
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239000002904 solvent Substances 0.000 description 8
FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 7
238000011907 photodimerization Methods 0.000 description 7
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 6
125000000746 allylic group Chemical group 0.000 description 5
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 5
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230000005298 paramagnetic effect Effects 0.000 description 5
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230000001235 sensitizing effect Effects 0.000 description 5
TXNWMICHNKMOBR-UHFFFAOYSA-N 1,2-dimethylcyclohexene Chemical compound CC1=C(C)CCCC1 TXNWMICHNKMOBR-UHFFFAOYSA-N 0.000 description 4
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
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239000005711 Benzoic acid Substances 0.000 description 1
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239000004215 Carbon black (E152) Substances 0.000 description 1
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239000013638 trimer Substances 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
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Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA219,037A 1974-06-12 1975-01-30 Reactions et catalyseurs photosensibilisants, lies a des polymeres Expired CA1044639A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA306,979A CA1054971A (fr)	1974-06-12	1978-07-07	Reactions aidees par des catalyseurs de photosensibilisation lies a des chaines polymeriques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US47869474A	1974-06-12	1974-06-12

Publications (1)

Publication Number	Publication Date
CA1044639A true CA1044639A (fr)	1978-12-19

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ID=23901000

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA219,037A Expired CA1044639A (fr)	1974-06-12	1975-01-30	Reactions et catalyseurs photosensibilisants, lies a des polymeres

Country Status (1)

Country	Link
CA (1)	CA1044639A (fr)

Cited By (13)

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Publication number	Priority date	Publication date	Assignee	Title
US4857652A (en) *	1986-07-17	1989-08-15	Board Of Governors Of Wayne State University	Chemiluminescent 1,2-dioxetane compounds
US4915804A (en) *	1988-12-20	1990-04-10	Allied-Signal Inc.	Titanate bound photosensitizer for producing singlet oxygen
US4921589A (en) *	1988-12-20	1990-05-01	Allied-Signal Inc.	Polysiloxane bound photosensitizer for producing singlet oxygen
US4959182A (en) *	1986-07-17	1990-09-25	Board Of Governors Of Wayne State University	Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
US4962192A (en) *	1986-07-17	1990-10-09	Board Of Governors Of Wayne State University	Chemiluminescent 1,2-dioxetane compounds
US4983670A (en) *	1988-12-20	1991-01-08	Allied-Signal Inc.	Cellulose acetate bound photosensitizer for producing singlet oxygen
US4986921A (en) *	1988-12-20	1991-01-22	Allied-Signal Inc.	Cellulose acetate bound photosensitizer for producing singlet oxygen
US5013827A (en) *	1986-07-17	1991-05-07	Board Of Governors Of Wayne State University	Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
US5068339A (en) *	1986-07-17	1991-11-26	Board Of Governors Of Wayne State University	Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
US5438146A (en) *	1986-07-17	1995-08-01	Board Of Governors Of Wayne State University	Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
US5707559A (en) *	1986-07-17	1998-01-13	Tropix, Inc.	Chemiluminescent 1,2-dioxetane compounds
US5891626A (en) *	1986-07-17	1999-04-06	Tropix, Inc.	Method providing enhanced chemiluminescence from 1,2-dioxetanes
US6322727B1 (en)	1986-07-24	2001-11-27	Tropix, Inc.	Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes

1975
- 1975-01-30 CA CA219,037A patent/CA1044639A/fr not_active Expired

Cited By (22)

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Publication number	Priority date	Publication date	Assignee	Title
US5707559A (en) *	1986-07-17	1998-01-13	Tropix, Inc.	Chemiluminescent 1,2-dioxetane compounds
US5891626A (en) *	1986-07-17	1999-04-06	Tropix, Inc.	Method providing enhanced chemiluminescence from 1,2-dioxetanes
US6133459A (en) *	1986-07-17	2000-10-17	Tropix, Inc.	Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
US4959182A (en) *	1986-07-17	1990-09-25	Board Of Governors Of Wayne State University	Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
US4962192A (en) *	1986-07-17	1990-10-09	Board Of Governors Of Wayne State University	Chemiluminescent 1,2-dioxetane compounds
US6107024A (en) *	1986-07-17	2000-08-22	Tropix, Inc.	Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
US5438146A (en) *	1986-07-17	1995-08-01	Board Of Governors Of Wayne State University	Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
US5013827A (en) *	1986-07-17	1991-05-07	Board Of Governors Of Wayne State University	Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
US5068339A (en) *	1986-07-17	1991-11-26	Board Of Governors Of Wayne State University	Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
US5631353A (en) *	1986-07-17	1997-05-20	Board Of Governors Of Wayne State University	Alkene adamantane intermediates and the corresponding 1,2-dioxetanes
US4857652A (en) *	1986-07-17	1989-08-15	Board Of Governors Of Wayne State University	Chemiluminescent 1,2-dioxetane compounds
US5616729A (en) *	1986-07-17	1997-04-01	Board Of Governors Of Wayne State University	Enhanced chemiluminescence from 1,2-dioxetanes through energy transfer to tethered fluorescers
US5386017A (en) *	1986-07-17	1995-01-31	Board Of Governors Of Wayne State University	Alkenes for producing chemiluminescent 1, 2-dioxetane compounds
US5652345A (en) *	1986-07-17	1997-07-29	Tropix, Inc.	1,2-dioxetane compound
US5698728A (en) *	1986-07-17	1997-12-16	Board Of Governors Of Wayne State University	Alkene intermediates for preparing 1,2-dioxetanes
US6322727B1 (en)	1986-07-24	2001-11-27	Tropix, Inc.	Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes
US6514717B2 (en)	1986-07-24	2003-02-04	Tropix, Inc.	Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes
US6913897B2 (en)	1986-07-24	2005-07-05	Applera Corporation	Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes
US4915804A (en) *	1988-12-20	1990-04-10	Allied-Signal Inc.	Titanate bound photosensitizer for producing singlet oxygen
US4986921A (en) *	1988-12-20	1991-01-22	Allied-Signal Inc.	Cellulose acetate bound photosensitizer for producing singlet oxygen
US4983670A (en) *	1988-12-20	1991-01-08	Allied-Signal Inc.	Cellulose acetate bound photosensitizer for producing singlet oxygen
US4921589A (en) *	1988-12-20	1990-05-01	Allied-Signal Inc.	Polysiloxane bound photosensitizer for producing singlet oxygen

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