JPH0233356B2 - - Google Patents
Info
- Publication number
- JPH0233356B2 JPH0233356B2 JP52147281A JP14728177A JPH0233356B2 JP H0233356 B2 JPH0233356 B2 JP H0233356B2 JP 52147281 A JP52147281 A JP 52147281A JP 14728177 A JP14728177 A JP 14728177A JP H0233356 B2 JPH0233356 B2 JP H0233356B2
- Authority
- JP
- Japan
- Prior art keywords
- protein
- water
- prepolymer
- enzyme
- isocyanate
- 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 - Lifetime
Links
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- 108090000623 proteins and genes Proteins 0.000 claims description 110
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- 229910001868 water Inorganic materials 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 41
- 239000007788 liquid Substances 0.000 claims description 34
- 239000006185 dispersion Substances 0.000 claims description 33
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 235000018102 proteins Nutrition 0.000 description 104
- 229940088598 enzyme Drugs 0.000 description 73
- 239000004814 polyurethane Substances 0.000 description 34
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 33
- 229920002635 polyurethane Polymers 0.000 description 33
- -1 poly(urea-urethane) Polymers 0.000 description 25
- 229920005862 polyol Polymers 0.000 description 24
- 150000003077 polyols Chemical class 0.000 description 24
- 239000000047 product Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 229920001228 polyisocyanate Polymers 0.000 description 15
- 239000005056 polyisocyanate Substances 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
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- 238000002156 mixing Methods 0.000 description 12
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 5
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 229920002307 Dextran Polymers 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000000872 buffer Substances 0.000 description 3
- 229940106157 cellulase Drugs 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 108040007629 peroxidase activity proteins Proteins 0.000 description 3
- 238000012552 review Methods 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- 102100026189 Beta-galactosidase Human genes 0.000 description 2
- 108010004032 Bromelains Proteins 0.000 description 2
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- 101710088194 Dehydrogenase Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010015776 Glucose oxidase Proteins 0.000 description 2
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- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
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- BKCJYMHMVAREFC-UHFFFAOYSA-N 1-(2-hydroxypropoxy)octan-2-ol Chemical compound CCCCCCC(O)COCC(C)O BKCJYMHMVAREFC-UHFFFAOYSA-N 0.000 description 1
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- 239000012490 blank solution Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- VWFCRSWRULWBAH-UHFFFAOYSA-N butane-1,2-diol butane-1,3-diol butane-1,4-diol but-2-ene-1,4-diol cyclohexane-1,2-diol decane-1,10-diol hexane-1,2-diol pentane-1,5-diol propane-1,2-diol propane-1,3-diol Chemical compound C(C=CCO)O.C1(C(CCCC1)O)O.C(CCCCCCCCCO)O.C(C(CCCC)O)O.C(CCCCO)O.C(CCCO)O.C(CC(C)O)O.C(C(CC)O)O.C(CCO)O.C(C(C)O)O VWFCRSWRULWBAH-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940048961 cholinesterase Drugs 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 102000006602 glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 1
- 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- 108010004872 glycocyamine phosphokinase Proteins 0.000 description 1
- 108010062584 glycollate oxidase Proteins 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229940098197 human immunoglobulin g Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 108020004410 pectinesterase Proteins 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000012257 stirred material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 108010038851 tannase Proteins 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y305/00—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5)
- C12Y305/01—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5) in linear amides (3.5.1)
- C12Y305/01011—Penicillin amidase (3.5.1.11), i.e. penicillin-amidohydrolase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/089—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C12N11/093—Polyurethanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/38—Albumins
- A61K38/385—Serum albumin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/43—Enzymes; Proenzymes; Derivatives thereof
- A61K38/46—Hydrolases (3)
- A61K38/48—Hydrolases (3) acting on peptide bonds (3.4)
- A61K38/482—Serine endopeptidases (3.4.21)
- A61K38/4826—Trypsin (3.4.21.4) Chymotrypsin (3.4.21.1)
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
- C08G18/6446—Proteins and derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
- C12Y304/21—Serine endopeptidases (3.4.21)
- C12Y304/21004—Trypsin (3.4.21.4)
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Microbiology (AREA)
- Public Health (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mycology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/749,430 US4094744A (en) | 1976-11-18 | 1976-12-10 | Water-dispersible protein/polyurethane reaction product |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5379094A JPS5379094A (en) | 1978-07-13 |
| JPH0233356B2 true JPH0233356B2 (nl) | 1990-07-26 |
Family
ID=25013731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14728177A Granted JPS5379094A (en) | 1976-12-10 | 1977-12-09 | Aqueous dispesing system of bound protein |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5379094A (nl) |
| AT (1) | AT356620B (nl) |
| BE (1) | BE861602A (nl) |
| CH (1) | CH634589A5 (nl) |
| DE (1) | DE2755053A1 (nl) |
| FR (1) | FR2393005B1 (nl) |
| GB (1) | GB1574508A (nl) |
| MX (1) | MX4534E (nl) |
| NL (1) | NL187585C (nl) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226935A (en) * | 1978-08-07 | 1980-10-07 | W. R. Grace & Co. | Enzymatic diagnostic composition |
| US4652524A (en) * | 1980-10-02 | 1987-03-24 | Ivan E. Modrovich | Soluble stabilized enzymes |
| US4732851A (en) * | 1982-03-16 | 1988-03-22 | Purification Engineering, Inc. | Immobilization of cells with a polyazetidine prepolymer |
| DE3705687A1 (de) * | 1987-02-23 | 1988-09-01 | Boehringer Mannheim Gmbh | Polyurethanmodifizierte enzyme |
| US7335400B2 (en) | 2001-07-24 | 2008-02-26 | University Of Pittsburgh | Irreversible immobilization of enzymes into polyurethane coatings |
| BR0211402A (pt) * | 2001-07-24 | 2005-02-22 | Univ Pittsburgh | Imobilização irreversìvel de diisopropilfluorofosfatase em revestimentos de poliuretano |
| US9121016B2 (en) * | 2011-09-09 | 2015-09-01 | Toyota Motor Engineering & Manufacturing North America, Inc. | Coatings containing polymer modified enzyme for stable self-cleaning of organic stains |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3672955A (en) * | 1970-05-20 | 1972-06-27 | Us Agriculture | Preparation of an insoluble active enzyme |
| US3929574A (en) * | 1972-05-03 | 1975-12-30 | Grace W R & Co | Use of enzymes bound to polyurethane |
-
1977
- 1977-12-07 BE BE183252A patent/BE861602A/xx not_active IP Right Cessation
- 1977-12-07 DE DE19772755053 patent/DE2755053A1/de active Granted
- 1977-12-08 NL NLAANVRAGE7713584,A patent/NL187585C/nl not_active IP Right Cessation
- 1977-12-08 GB GB51208/77A patent/GB1574508A/en not_active Expired
- 1977-12-08 FR FR7737083A patent/FR2393005B1/fr not_active Expired
- 1977-12-09 AT AT883577A patent/AT356620B/de not_active IP Right Cessation
- 1977-12-09 JP JP14728177A patent/JPS5379094A/ja active Granted
- 1977-12-09 MX MX776679U patent/MX4534E/es unknown
- 1977-12-09 CH CH1515877A patent/CH634589A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH634589A5 (en) | 1983-02-15 |
| NL187585C (nl) | 1991-11-18 |
| FR2393005B1 (fr) | 1982-11-12 |
| JPS5379094A (en) | 1978-07-13 |
| DE2755053A1 (de) | 1978-06-22 |
| BE861602A (fr) | 1978-03-31 |
| AT356620B (de) | 1980-05-12 |
| NL187585B (nl) | 1991-06-17 |
| NL7713584A (nl) | 1978-06-13 |
| DE2755053C2 (nl) | 1989-11-09 |
| FR2393005A1 (fr) | 1978-12-29 |
| ATA883577A (de) | 1979-10-15 |
| GB1574508A (en) | 1980-09-10 |
| MX4534E (es) | 1982-06-03 |
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