CA1255842A - Compositions d'acrylate-polyurethane - Google Patents

Compositions d'acrylate-polyurethane

Info

Publication number: CA1255842A
Authority: CA; Canada
Prior art keywords: acrylate composition; hydrophilic polyurethane; polyurethane acrylate; hydrophilic; composition
Prior art date: 1983-12-07
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

CA000442725A

Other languages

English (en)

Inventor

Christian W. Johnston

Francis E. Gould

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.)

Tyndale Plains Hunter Ltd

Original Assignee

Tyndale Plains Hunter Ltd

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.)

1983-12-07

Filing date

1983-12-07

Publication date

1989-06-13

1983-12-07 Application filed by Tyndale Plains Hunter Ltd filed Critical Tyndale Plains Hunter Ltd

1983-12-07 Priority to CA000442725A priority Critical patent/CA1255842A/fr

1989-06-13 Application granted granted Critical

1989-06-13 Publication of CA1255842A publication Critical patent/CA1255842A/fr

Status Expired legal-status Critical Current

Links

239000004814 polyurethane Substances 0.000 title claims abstract description 68
239000000203 mixture Substances 0.000 title claims abstract description 64
229920002635 polyurethane Polymers 0.000 title claims abstract description 61
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
239000007789 gas Substances 0.000 claims abstract description 5
239000000017 hydrogel Substances 0.000 claims abstract description 5
229920005749 polyurethane resin Polymers 0.000 claims abstract description 5
238000007654 immersion Methods 0.000 claims abstract description 3
150000002500 ions Chemical class 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
239000003814 drug Substances 0.000 claims description 18
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
239000007943 implant Substances 0.000 claims description 9
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 8
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 8
239000012528 membrane Substances 0.000 claims description 8
239000003433 contraceptive agent Substances 0.000 claims description 7
230000002254 contraceptive effect Effects 0.000 claims description 7
125000005442 diisocyanate group Chemical group 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
229920005862 polyol Polymers 0.000 claims description 5
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000000502 dialysis Methods 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
150000003077 polyols Chemical class 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
229940124976 antitubercular drug Drugs 0.000 claims description 2
239000008280 blood Substances 0.000 claims description 2
210000004369 blood Anatomy 0.000 claims description 2
239000005556 hormone Substances 0.000 claims description 2
229940088597 hormone Drugs 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
238000000034 method Methods 0.000 claims description 2
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 2
229960004306 sulfadiazine Drugs 0.000 claims description 2
239000011782 vitamin Substances 0.000 claims description 2
229940088594 vitamin Drugs 0.000 claims description 2
229930003231 vitamin Natural products 0.000 claims description 2
235000013343 vitamin Nutrition 0.000 claims description 2
MIQWEMDDUPSLRW-UHFFFAOYSA-N [O].O=C=O Chemical group [O].O=C=O MIQWEMDDUPSLRW-UHFFFAOYSA-N 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
125000002345 steroid group Chemical group 0.000 claims 1
150000003722 vitamin derivatives Chemical class 0.000 claims 1
239000013627 low molecular weight specie Substances 0.000 abstract 1
229940048053 acrylate Drugs 0.000 description 19
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 14
-1 nitrile carbonates Chemical class 0.000 description 12
239000000047 product Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
150000002596 lactones Chemical class 0.000 description 8
229920000642 polymer Polymers 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
150000002009 diols Chemical class 0.000 description 5
BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
239000005056 polyisocyanate Substances 0.000 description 4
229920001228 polyisocyanate Polymers 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
235000015071 dressings Nutrition 0.000 description 3
239000011953 free-radical catalyst Substances 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
239000005058 Isophorone diisocyanate Substances 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
238000013270 controlled release Methods 0.000 description 2
125000004956 cyclohexylene group Chemical group 0.000 description 2
239000012975 dibutyltin dilaurate Substances 0.000 description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011342 resin composition Substances 0.000 description 2
238000009987 spinning Methods 0.000 description 2
239000012974 tin catalyst Substances 0.000 description 2
OGLCQHRZUSEXNB-UAPNVWQMSA-N (2r,3r,3ar,6ar)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2h-furo[3,2-b]furan-5-one Chemical compound OC1C(=O)O[C@@H]2[C@@H](O)[C@H](O)O[C@@H]21 OGLCQHRZUSEXNB-UAPNVWQMSA-N 0.000 description 1
RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
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
VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 1
QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
UYUXSRADSPPKRZ-UHFFFAOYSA-N D-glucuronic acid gamma-lactone Natural products O=CC(O)C1OC(=O)C(O)C1O UYUXSRADSPPKRZ-UHFFFAOYSA-N 0.000 description 1
206010059866 Drug resistance Diseases 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
CCFQKJBRMQOAFR-UHFFFAOYSA-N N=C=O.N=C=O.CCC1=CC=CC=C1CC Chemical compound N=C=O.N=C=O.CCC1=CC=CC=C1CC CCFQKJBRMQOAFR-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
229940092738 beeswax Drugs 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
YGXPXNPJGDEFTN-UHFFFAOYSA-N carbonic acid;hexanedinitrile Chemical compound OC(O)=O.N#CCCCCC#N YGXPXNPJGDEFTN-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
238000010612 desalination reaction Methods 0.000 description 1
125000004386 diacrylate group Chemical group 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
LTLCGIKWGSDBMN-UHFFFAOYSA-L dimercury diacetate Chemical compound CC(=O)O[Hg][Hg]OC(C)=O LTLCGIKWGSDBMN-UHFFFAOYSA-L 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DUVBMJIZYQQKSU-UHFFFAOYSA-N ethyl carbamate;methyl 2-methylprop-2-enoate Chemical compound CCOC(N)=O.COC(=O)C(C)=C DUVBMJIZYQQKSU-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
210000004905 finger nail Anatomy 0.000 description 1
229960003681 gluconolactone Drugs 0.000 description 1
229950002441 glucurolactone Drugs 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
150000002772 monosaccharides Chemical class 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005702 oxyalkylene group Chemical group 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
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 1
229940043267 rhodamine b Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000003832 thermite Substances 0.000 description 1
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
239000000814 tuberculostatic agent Substances 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Landscapes

Materials For Medical Uses (AREA)
Macromonomer-Based Addition Polymer (AREA)

CA000442725A 1983-12-07 1983-12-07 Compositions d'acrylate-polyurethane Expired CA1255842A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000442725A CA1255842A (fr)	1983-12-07	1983-12-07	Compositions d'acrylate-polyurethane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000442725A CA1255842A (fr)	1983-12-07	1983-12-07	Compositions d'acrylate-polyurethane

Publications (1)

Publication Number	Publication Date
CA1255842A true CA1255842A (fr)	1989-06-13

Family

ID=4126686

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000442725A Expired CA1255842A (fr)	1983-12-07	1983-12-07	Compositions d'acrylate-polyurethane

Country Status (1)

Country	Link
CA (1)	CA1255842A (fr)

1983
- 1983-12-07 CA CA000442725A patent/CA1255842A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-06-13	MKEX	Expiry

Publication	Publication Date	Title
US4780512A (en)	1988-10-25	Polyurethane acrylate compositions
CA1175596A (fr)	1984-10-02	Composition hydrophile a base de polyurethane diacrylate
US4439585A (en)	1984-03-27	Polyurethane diacrylate compositions as carrier for pharmacological agents
US4424305A (en)	1984-01-03	Surgical implants formed of polyurethane diacrylate compositions
GB2150938A (en)	1985-07-10	Hydrophilic polyurethane acrylate compositions
US4439583A (en)	1984-03-27	Polyurethane diacrylate compositions useful in forming canulae
US4408023A (en)	1983-10-04	Polyurethane diacrylate compositions useful for contact lenses and the like
US4496535A (en)	1985-01-29	Polyurethane polyene compositions
US4454309A (en)	1984-06-12	Polyurethane polyene compositions
US4810582A (en)	1989-03-07	Hydrophilic polyurethane composition
US4798876A (en)	1989-01-17	Hydrophilic polyurethane composition
US4255550A (en)	1981-03-10	Polyurethane polymers characterized by carboxylate groups and hydroxyl groups in the polymer backbone
US4789720A (en)	1988-12-06	Hydrophilic polyurethanes prepared from mixed oxyalkylene glycols
US5728762A (en)	1998-03-17	Polyether polyurethane polymers, gels, solutions and uses thereof
CN1950098B (zh)	2013-02-27	生物可降解聚氨酯和聚氨酯脲
US4156067A (en)	1979-05-22	Polyurethane polymers characterized by lactone groups and hydroxyl groups in the polymer backbone
US4136250A (en)	1979-01-23	Polysiloxane hydrogels
US4131604A (en)	1978-12-26	Polyurethane elastomer for heart assist devices
US5932200A (en)	1999-08-03	Polyether polyurethane polymers, gels, solutions and uses thereof
US4451635A (en)	1984-05-29	Polyurethane quaternary ammonium salts
US4439584A (en)	1984-03-27	Gas and ion permeable membranes formed of polyurethane diacrylate compositions
GB2111067A (en)	1983-06-29	Extrudable polyurethane for prosthetic devices
CA1155591A (fr)	1983-10-18	Polyurethanes dont la charpente porte des groupes lactone et hydroxyle
US4490423A (en)	1984-12-25	Polyurethane polyene compositions
WO1988000214A1 (fr)	1988-01-14	Polymeres de polyurethane prepares a partir de resines de glycol d'alkylene melangees