CA1061931A - Vecteur hydrophile ou sous forme d'hydrogel - Google Patents

Vecteur hydrophile ou sous forme d'hydrogel

Info

Publication number: CA1061931A
Authority: CA; Canada
Prior art keywords: acid; imine; resin; mixtures; ethylene
Prior art date: 1974-06-25
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

CA228,542A

Other languages

English (en)

Inventor

Donald E. Hudgin

Edgar A. Blair

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.)

Individual

Original Assignee

Individual

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.)

1974-06-25

Filing date

1975-06-04

Publication date

1979-09-04

1974-06-25 Priority claimed from US05/482,874 external-priority patent/US3975350A/en

1975-06-04 Application filed by Individual filed Critical Individual

1979-09-04 Application granted granted Critical

1979-09-04 Publication of CA1061931A publication Critical patent/CA1061931A/fr

Status Expired legal-status Critical Current

Links

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239000011347 resin Substances 0.000 claims abstract description 229
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239000012948 isocyanate Substances 0.000 claims abstract description 84
150000002513 isocyanates Chemical class 0.000 claims abstract description 69
238000000576 coating method Methods 0.000 claims abstract description 56
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239000013543 active substance Substances 0.000 claims abstract description 40
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
229910052799 carbon Inorganic materials 0.000 claims abstract description 18
239000007788 liquid Substances 0.000 claims abstract description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
239000007943 implant Substances 0.000 claims abstract description 7
239000012633 leachable Substances 0.000 claims abstract description 7
239000001301 oxygen Substances 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
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239000010839 body fluid Substances 0.000 claims abstract 3
239000000203 mixture Substances 0.000 claims description 94
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-1 maleic acid ester Chemical class 0.000 claims description 56
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 55
150000001875 compounds Chemical class 0.000 claims description 53
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239000002253 acid Substances 0.000 claims description 44
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 42
OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 claims description 41
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 27
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XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 14
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 14
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
239000011976 maleic acid Substances 0.000 claims description 13
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YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 claims description 12
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 12
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VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 10
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150000002466 imines Chemical class 0.000 claims description 9
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
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RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 8
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 7
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
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WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
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125000003277 amino group Chemical group 0.000 claims description 6
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XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 6
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FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 6
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BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 5
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
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ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
NONJJLVGHLVQQM-JHXYUMNGSA-N phenethicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C)OC1=CC=CC=C1 NONJJLVGHLVQQM-JHXYUMNGSA-N 0.000 description 1
229960004894 pheneticillin Drugs 0.000 description 1
WRLGYAWRGXKSKG-UHFFFAOYSA-M phenobarbital sodium Chemical compound [Na+].C=1C=CC=CC=1C1(CC)C(=O)NC([O-])=NC1=O WRLGYAWRGXKSKG-UHFFFAOYSA-M 0.000 description 1
229960002511 phenobarbital sodium Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
150000003022 phthalic acids Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004999 plastisol Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
229920006295 polythiol Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000000934 spermatocidal agent Substances 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
230000002522 swelling effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
210000002435 tendon Anatomy 0.000 description 1
238000012360 testing method Methods 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide 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
239000003860 topical agent Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000012800 visualization Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
238000004078 waterproofing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
230000003245 working effect Effects 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA228,542A 1974-06-25 1975-06-04 Vecteur hydrophile ou sous forme d'hydrogel Expired CA1061931A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/482,874 US3975350A (en)	1972-08-02	1974-06-25	Hydrophilic or hydrogel carrier systems such as coatings, body implants and other articles

Publications (1)

Publication Number	Publication Date
CA1061931A true CA1061931A (fr)	1979-09-04

Family

ID=23917791

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA228,542A Expired CA1061931A (fr)	1974-06-25	1975-06-04	Vecteur hydrophile ou sous forme d'hydrogel

Country Status (1)

Country	Link
CA (1)	CA1061931A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN112480361A (zh) *	2020-12-01	2021-03-12	上海恒安聚氨酯股份有限公司	一种透湿的热塑性聚氨酯薄膜的制备方法

1975
- 1975-06-04 CA CA228,542A patent/CA1061931A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN112480361A (zh) *	2020-12-01	2021-03-12	上海恒安聚氨酯股份有限公司	一种透湿的热塑性聚氨酯薄膜的制备方法
CN112480361B (zh) *	2020-12-01	2022-03-08	上海恒安聚氨酯股份有限公司	一种透湿的热塑性聚氨酯薄膜的制备方法

Publication	Publication Date	Title
US3975350A (en)	1976-08-17	Hydrophilic or hydrogel carrier systems such as coatings, body implants and other articles
US5334691A (en)	1994-08-02	Hydrophilic polyurethanes of improved strength
US5120816A (en)	1992-06-09	Hydrophilic polyurethanes of improved strength
US4789720A (en)	1988-12-06	Hydrophilic polyurethanes prepared from mixed oxyalkylene glycols
US4192827A (en)	1980-03-11	Water-insoluble hydrophilic copolymers
US4304591A (en)	1981-12-08	Water-insoluble hydrophilic copolymers used as carriers for medicaments and pesticides
US4973320A (en)	1990-11-27	Tissue-compatible medical device and method for manufacturing the same
DE3002038C2 (fr)	1990-12-06
US5993972A (en)	1999-11-30	Hydrophilic and hydrophobic polyether polyurethanes and uses therefor
US4255550A (en)	1981-03-10	Polyurethane polymers characterized by carboxylate groups and hydroxyl groups in the polymer backbone
CA1175596A (fr)	1984-10-02	Composition hydrophile a base de polyurethane diacrylate
US4810582A (en)	1989-03-07	Hydrophilic polyurethane composition
AU613177B2 (en)	1991-07-25	Container, method and composition for controlling the release of volatile liquid from an aqueous mixture
CA2670141C (fr)	2014-09-16	Composition et articles contenant une matrice polymere reticulee et un liquide actif immobilise, et procedes d'elaboration correspondant
US5118779A (en)	1992-06-02	Hydrophilic polyurethane elastomers
JPS61235465A (ja)	1986-10-20	親水性重合体で被覆した三次元基体物品
CA1097448A (fr)	1981-03-10	Copolymeres hydrophiles, insolubles dans l'eau
US5159050A (en)	1992-10-27	Polyurethane and medical article therefrom
CA1155591A (fr)	1983-10-18	Polyurethanes dont la charpente porte des groupes lactone et hydroxyle
US5159051A (en)	1992-10-27	Biostable polyurethane
JP2004530652A (ja)	2004-10-07	哺乳動物細胞増殖の阻害または予防のための方法と臨床装置
JPH05505410A (ja)	1993-08-12	ポリマー物質
WO1988000214A1 (fr)	1988-01-14	Polymeres de polyurethane prepares a partir de resines de glycol d'alkylene melangees
CA1061931A (fr)	1979-09-04	Vecteur hydrophile ou sous forme d'hydrogel
CA1255842A (fr)	1989-06-13	Compositions d'acrylate-polyurethane