CA1086883A - Ionogenic hydrophilic water/insoluble gels from partially hydrolyzed acrylonitrile polymers and copolymers and a method of manufacturing same - Google Patents
Ionogenic hydrophilic water/insoluble gels from partially hydrolyzed acrylonitrile polymers and copolymers and a method of manufacturing sameInfo
- Publication number
- CA1086883A CA1086883A CA240,326A CA240326A CA1086883A CA 1086883 A CA1086883 A CA 1086883A CA 240326 A CA240326 A CA 240326A CA 1086883 A CA1086883 A CA 1086883A
- Authority
- CA
- Canada
- Prior art keywords
- water
- solution
- hydrogel
- polymer
- acrylonitrile
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229920001577 copolymer Polymers 0.000 title claims abstract description 19
- 239000000499 gel Substances 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 229920002239 polyacrylonitrile Polymers 0.000 title claims description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- 239000000017 hydrogel Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 20
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000008961 swelling Effects 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000007935 neutral effect Effects 0.000 claims abstract description 5
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 59
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 30
- 239000002585 base Substances 0.000 claims description 23
- 238000004132 cross linking Methods 0.000 claims description 20
- 230000007062 hydrolysis Effects 0.000 claims description 20
- 238000006460 hydrolysis reaction Methods 0.000 claims description 20
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
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- 239000011734 sodium Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
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- 239000012047 saturated solution Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 9
- 230000035699 permeability Effects 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000001356 surgical procedure Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 acryl Chemical group 0.000 description 9
- 230000003247 decreasing effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000005345 coagulation Methods 0.000 description 6
- 230000015271 coagulation Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 3
- 244000228957 Ferula foetida Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 240000004658 Medicago sativa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000002226 simultaneous effect Effects 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
- C08L33/20—Homopolymers or copolymers of acrylonitrile
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Medical Uses (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Eyeglasses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS7400008051A CS179567B1 (en) | 1974-11-25 | 1974-11-25 | Ionogennic hydrophilic in water insoluble gels based on partial saponificated polymers or copolymers acrylonitrile and method of preparing them |
| CSPV8051-74 | 1974-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086883A true CA1086883A (en) | 1980-09-30 |
Family
ID=5430584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA240,326A Expired CA1086883A (en) | 1974-11-25 | 1975-11-24 | Ionogenic hydrophilic water/insoluble gels from partially hydrolyzed acrylonitrile polymers and copolymers and a method of manufacturing same |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4107121A (oth) |
| JP (1) | JPS5174084A (oth) |
| AT (1) | AT341216B (oth) |
| CA (1) | CA1086883A (oth) |
| CS (1) | CS179567B1 (oth) |
| DE (1) | DE2552614C3 (oth) |
| FR (1) | FR2292010A1 (oth) |
| GB (1) | GB1511579A (oth) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5527346A (en) * | 1978-08-16 | 1980-02-27 | Japan Exlan Co Ltd | Aqueous dispersion of microhydrogel, its preparation, and preparation of microhydrogel |
| GB2044273B (en) * | 1979-02-12 | 1983-05-25 | Japlan Exlan Co Ltd | Fibrous material and filters for removing water from hydrophobic liquids |
| US4385026A (en) * | 1979-08-13 | 1983-05-24 | Imperial Chemical Industries Limited | Removal of solvent from gels of high molecular weight crystalline polymers |
| JPS5911343B2 (ja) * | 1979-11-27 | 1984-03-14 | 東ソー株式会社 | 両性イオン交換体 |
| US4539234A (en) * | 1981-05-27 | 1985-09-03 | Unitika Ltd. | Urethral catheter capable of preventing urinary tract infection and process for producing the same |
| GB2124899A (en) * | 1982-07-15 | 1984-02-29 | Standard Telephones Cables Ltd | Improved rumen bolus |
| US4558100A (en) * | 1984-07-03 | 1985-12-10 | Grain Processing Corporation | Absorbent compositions |
| DE3613207A1 (de) * | 1986-04-18 | 1987-10-22 | Akzo Gmbh | Mit wasser quellbare zusammensetzung, ihre herstellung und verwendung |
| DE3619721A1 (de) * | 1986-06-12 | 1987-12-17 | Wolff Walsrode Ag | Verfahren zur herstellung wasserloeslicher copolymerisate und deren verwendung als schlichtmittel |
| GB8620845D0 (en) * | 1986-08-28 | 1986-10-08 | Reckitt & Colmann Prod Ltd | Treatment of textile surfaces |
| US4828705A (en) * | 1986-10-31 | 1989-05-09 | Kingston Technologies, Inc. | Pressure-dependent anisotropic-transport membrane system |
| CS267858B1 (en) * | 1987-01-12 | 1990-02-12 | Sulc Jiri | Contact,if need be,intra-ocular lens and method of its production |
| US5218039A (en) * | 1987-04-28 | 1993-06-08 | Kingston Technologies, Inc. | Pan emulsion |
| US4943618A (en) * | 1987-12-18 | 1990-07-24 | Kingston Technologies Limited Partnership | Method for preparing polyacrylonitrile copolymers by heterogeneous reaction of polyacrylonitrile aquagel |
| US5268178A (en) * | 1989-09-25 | 1993-12-07 | The Board Of Regents, The University Of Texas System | Biodegradable antibiotic implants and methods of their use in treating and preventing infections |
| US5252692A (en) * | 1990-11-23 | 1993-10-12 | Kingston Technologies, Inc. | Hydrophilic acrylic copolymers and method of preparation |
| US5270415A (en) * | 1990-12-21 | 1993-12-14 | Allergan Inc. | Balanced charge polymer and hydrophilic contact lens manufactured therefrom |
| US5217493A (en) * | 1992-03-11 | 1993-06-08 | Board Of Regents, The University Of Texas System | Antibacterial coated medical implants |
| US5362754A (en) * | 1992-11-12 | 1994-11-08 | Univ. Of Tx Md Anderson Cancer Center | M-EDTA pharmaceutical preparations and uses thereof |
| US5688516A (en) * | 1992-11-12 | 1997-11-18 | Board Of Regents, The University Of Texas System | Non-glycopeptide antimicrobial agents in combination with an anticoagulant, an antithrombotic or a chelating agent, and their uses in, for example, the preparation of medical devices |
| US5688855A (en) * | 1995-05-01 | 1997-11-18 | S.K.Y. Polymers, Inc. | Thin film hydrophilic coatings |
| DE19646856A1 (de) * | 1996-11-13 | 1998-05-14 | Bayer Ag | Präformierte Superabsorber mit hohem Quellvermögen |
| JP3982046B2 (ja) * | 1997-04-16 | 2007-09-26 | ソニー株式会社 | 高分子凝集剤 |
| US6165484A (en) * | 1997-08-26 | 2000-12-26 | Wake Forest University | EDTA and other chelators with or without antifungal antimicrobial agents for the prevention and treatment of fungal infections |
| US5932552A (en) | 1997-11-26 | 1999-08-03 | Keraplast Technologies Ltd. | Keratin-based hydrogel for biomedical applications and method of production |
| US6818018B1 (en) * | 1998-08-14 | 2004-11-16 | Incept Llc | In situ polymerizable hydrogels |
| US6720415B2 (en) | 1998-12-02 | 2004-04-13 | Princeton University | Compositions and methods for regulating bacterial pathogenesis |
| US7326542B2 (en) * | 1998-12-02 | 2008-02-05 | Princeton University | Compositions and methods for regulating bacterial pathogenesis |
| US6528107B2 (en) | 1999-01-19 | 2003-03-04 | Sulzer Carbomedics Inc. | Method for producing antimicrobial antithrombogenic medical devices |
| US6416549B1 (en) | 1999-07-19 | 2002-07-09 | Sulzer Carbomedics Inc. | Antithrombogenic annuloplasty ring having a biodegradable insert |
| US6416548B2 (en) | 1999-07-20 | 2002-07-09 | Sulzer Carbomedics Inc. | Antimicrobial annuloplasty ring having a biodegradable insert |
| US6371984B1 (en) * | 1999-09-13 | 2002-04-16 | Keraplast Technologies, Ltd. | Implantable prosthetic or tissue expanding device |
| US6783546B2 (en) | 1999-09-13 | 2004-08-31 | Keraplast Technologies, Ltd. | Implantable prosthetic or tissue expanding device |
| US6232406B1 (en) | 1999-09-30 | 2001-05-15 | Replication Medical Inc. | Hydrogel and method of making |
| US6264695B1 (en) | 1999-09-30 | 2001-07-24 | Replication Medical, Inc. | Spinal nucleus implant |
| JP2003532698A (ja) | 2000-05-10 | 2003-11-05 | プリンストン ユニバーシティ | 細菌の増殖および病理発生を調節するための化合物ならびに方法 |
| WO2001085773A2 (en) * | 2000-05-10 | 2001-11-15 | Princeton University | Luxo-sigma54 interactions and methods of use |
| US6679605B2 (en) * | 2000-05-22 | 2004-01-20 | Medennium, Inc. | Crystalline polymeric compositions for ophthalmic devices |
| US7056533B2 (en) | 2000-08-15 | 2006-06-06 | Surmodics, Inc. | Medicament incorporation matrix |
| US7713472B2 (en) * | 2001-01-12 | 2010-05-11 | Board Of Regents, The University Of Texas System | Antiseptic derivatives with broad spectrum antimicrobial activity for the impregnation of surfaces |
| US6589591B1 (en) | 2001-07-10 | 2003-07-08 | Baylor College Of Medicine | Method for treating medical devices using glycerol and an antimicrobial agent |
| US7306580B2 (en) | 2003-04-16 | 2007-12-11 | Cook Incorporated | Medical device with therapeutic agents |
| US20040256561A1 (en) * | 2003-06-17 | 2004-12-23 | Allyson Beuhler | Wide band light sensing pixel array |
| AU2004251823B2 (en) * | 2003-06-19 | 2010-06-03 | Janssen Pharmaceutica N.V. | Aminosulfonyl substituted 4-(aminomethyl)-piperidine benzamides as 5HT4-antagonists |
| CA2552911A1 (en) * | 2004-01-20 | 2005-08-11 | Board Of Regents, The University Of Texas System | Methods for coating and impregnating medical devices with antiseptic compositions |
| CA2561496A1 (en) * | 2004-04-02 | 2005-10-20 | Baylor College Of Medicine | Novel modification of medical prostheses |
| US20060051402A1 (en) * | 2004-09-08 | 2006-03-09 | Abilityone Corporation | Splinting orthopedic and rehabilitative product |
| CA2601918A1 (en) * | 2005-01-20 | 2006-07-27 | The Regents Of The University Of California | Cellular microarrays for screening differentiation factors |
| US20070093894A1 (en) * | 2005-10-25 | 2007-04-26 | Baylor College Of Medicine | Incorporation of antimicrobial combinations onto devices to reduce infection |
| EP1960013B1 (en) | 2005-11-18 | 2016-12-21 | The Board of Regents of The University of Texas System | Methods for coating surfaces with antimicrobial agents |
| US20070299201A1 (en) * | 2006-06-23 | 2007-12-27 | Replication Medical, Inc. | Process for manufacturing hydrogels |
| EP2084234A2 (en) * | 2006-11-08 | 2009-08-05 | Massachusetts Institute of Technology | Polymeric coatings that inactivate viruses and bacteria |
| TW200901890A (en) * | 2007-04-03 | 2009-01-16 | Sure Internat Ventures B V | New compostions and methods for cell killing |
| JP2010537997A (ja) * | 2007-08-27 | 2010-12-09 | マサチューセッツ インスティテュート オブ テクノロジー | 二機能性ポリマーに結合させたインフルエンザウイルス阻害剤 |
| DE112009002177B4 (de) | 2008-10-03 | 2018-01-11 | Replication Medical, Inc. | Blutgefäß-Schutzvorrichtung |
| WO2010045491A1 (en) * | 2008-10-15 | 2010-04-22 | Replication Medical, Inc. | Swellable interspinous stabilization implant |
| US8426044B2 (en) | 2009-03-20 | 2013-04-23 | Board Of Regents, The University Of Texas System | Method for imparting antimicrobial activity to a medical device |
| US20110066141A1 (en) * | 2009-09-11 | 2011-03-17 | Cook Incorporated | Implantable medical device having an anti-gastric distress agent |
| WO2012137166A1 (en) | 2011-04-07 | 2012-10-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | An oxoborolidine compound and uses thereof |
| WO2012137164A1 (en) | 2011-04-07 | 2012-10-11 | Biolinerx Ltd. | Antimicrobial compositions, antibiofilm compositions and uses thereof |
| CN104086699B (zh) * | 2014-07-04 | 2016-06-08 | 青岛科技大学 | 一种非共混型高稳定性聚丙烯酸酯吸水膨胀橡胶及其制备方法 |
| US9814496B2 (en) | 2015-09-15 | 2017-11-14 | Hydra Medical, LLC | Interspinous stabilization implant |
| EP3393746B1 (en) * | 2015-12-22 | 2020-08-26 | 3M Innovative Properties Company | One-piece sensor for a bioelectrode and processes for production |
| CA3030550A1 (en) | 2016-02-29 | 2017-09-08 | Aequor, Inc. | Antimicrobial compounds and methods of use |
| EP3474860B1 (en) | 2016-06-28 | 2021-12-15 | Aequor, Inc. | Antimicrobial compounds and methods of use |
| IL265812B2 (en) | 2016-10-06 | 2024-09-01 | Medicem Tech S R O | Osmotic cervical dilators combined with hydrogel |
| IL258467A (en) | 2018-03-29 | 2018-07-04 | Ilana Kolodkin Gal | Methods of disrupting a biofilm and/or preventing formation of same |
| US12034118B2 (en) | 2021-02-26 | 2024-07-09 | Scott M. Epstein | Rechargeable energy-storage device including partially-hydrolyzed structural hydrogel |
| CN116253906B (zh) * | 2023-02-28 | 2024-05-31 | 苏州大学 | 一种聚丙烯腈纤维弹性水凝胶及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2716093A (en) * | 1951-06-12 | 1955-08-23 | Du Pont | Acrylonitrile polymer solutions and process of shaping the same |
| US2812317A (en) * | 1953-08-19 | 1957-11-05 | Monsanto Chemicals | Hydrolyzed polyacrylonitrile polymers and process of preparing same |
| CS159361B1 (oth) * | 1970-09-08 | 1975-01-31 | ||
| US3897382A (en) * | 1972-07-14 | 1975-07-29 | Ceskoslovenska Akademie Ved | Method for the acid hydrolysis of acrylonitrile containing polymers, hydrogels and fibers of products prepared by said method |
-
1974
- 1974-11-25 CS CS7400008051A patent/CS179567B1/cs unknown
-
1975
- 1975-11-18 GB GB47462/75A patent/GB1511579A/en not_active Expired
- 1975-11-19 AT AT880275A patent/AT341216B/de not_active IP Right Cessation
- 1975-11-20 US US05/633,786 patent/US4107121A/en not_active Expired - Lifetime
- 1975-11-24 CA CA240,326A patent/CA1086883A/en not_active Expired
- 1975-11-24 DE DE2552614A patent/DE2552614C3/de not_active Expired
- 1975-11-25 JP JP50140304A patent/JPS5174084A/ja active Pending
- 1975-11-25 FR FR7535914A patent/FR2292010A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CS179567B1 (en) | 1977-11-30 |
| DE2552614C3 (de) | 1978-11-23 |
| FR2292010B1 (oth) | 1981-10-30 |
| ATA880275A (de) | 1977-05-15 |
| DE2552614A1 (de) | 1976-06-16 |
| US4107121A (en) | 1978-08-15 |
| FR2292010A1 (fr) | 1976-06-18 |
| JPS5174084A (oth) | 1976-06-26 |
| GB1511579A (en) | 1978-05-24 |
| DE2552614B2 (de) | 1978-03-23 |
| AT341216B (de) | 1978-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |