CA1061049A - Polymere hydrophile soluble dans l'alcool, obtenu par polymerisation aqueuse - Google Patents

Polymere hydrophile soluble dans l'alcool, obtenu par polymerisation aqueuse

Info

Publication number: CA1061049A
Authority: CA; Canada
Prior art keywords: water; polymer; monomer; polymers; process according
Prior art date: 1976-05-10
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

CA252,112A

Other languages

English (en)

Inventor

Robert A. Abrahams

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.)

National Patent Development Corp

Original Assignee

National Patent Development 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.)

1976-05-10

Filing date

1976-05-10

Publication date

1979-08-21

1976-05-10 Application filed by National Patent Development Corp filed Critical National Patent Development Corp

1976-05-10 Priority to CA252,112A priority Critical patent/CA1061049A/fr

1979-08-21 Application granted granted Critical

1979-08-21 Publication of CA1061049A publication Critical patent/CA1061049A/fr

Status Expired legal-status Critical Current

Links

229920001477 hydrophilic polymer Polymers 0.000 title claims description 6
238000006116 polymerization reaction Methods 0.000 title claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 21
229920000642 polymer Polymers 0.000 claims abstract description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
239000000178 monomer Substances 0.000 claims abstract description 34
150000005690 diesters Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 15
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 13
239000003999 initiator Substances 0.000 claims description 13
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical group FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
230000000379 polymerizing effect Effects 0.000 claims description 2
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-1 hydroxyalkyl methacrylate Chemical compound 0.000 abstract description 14
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 5
125000004386 diacrylate group Chemical group 0.000 abstract 1
229920003176 water-insoluble polymer Polymers 0.000 abstract 1
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239000003960 organic solvent Substances 0.000 description 11
230000000694 effects Effects 0.000 description 8
BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 8
239000000463 material Substances 0.000 description 7
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238000012360 testing method Methods 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
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ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
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238000012512 characterization method Methods 0.000 description 2
CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 2
CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
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238000010348 incorporation Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
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229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002510 pyrogen Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
238000004904 shortening Methods 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229960003600 silver sulfadiazine Drugs 0.000 description 1
UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 1
229960004257 sulfaguanidine Drugs 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
229960002211 sulfapyridine Drugs 0.000 description 1
JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
229960001544 sulfathiazole Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
229940063650 terramycin Drugs 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
229940072358 xylocaine Drugs 0.000 description 1
229940118257 zinc undecylenate Drugs 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA252,112A 1976-05-10 1976-05-10 Polymere hydrophile soluble dans l'alcool, obtenu par polymerisation aqueuse Expired CA1061049A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA252,112A CA1061049A (fr)	1976-05-10	1976-05-10	Polymere hydrophile soluble dans l'alcool, obtenu par polymerisation aqueuse

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA252,112A CA1061049A (fr)	1976-05-10	1976-05-10	Polymere hydrophile soluble dans l'alcool, obtenu par polymerisation aqueuse

Publications (1)

Publication Number	Publication Date
CA1061049A true CA1061049A (fr)	1979-08-21

Family

ID=4105916

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA252,112A Expired CA1061049A (fr)	1976-05-10	1976-05-10	Polymere hydrophile soluble dans l'alcool, obtenu par polymerisation aqueuse

Country Status (1)

Country	Link
CA (1)	CA1061049A (fr)

1976
- 1976-05-10 CA CA252,112A patent/CA1061049A/fr not_active Expired

Publication	Publication Date	Title
US3963685A (en)	1976-06-15	Alcohol soluble hydrophilic polymer via aqueous polymerization
Güven et al.	1999	A review on the radiation synthesis of copolymeric hydrogels for adsorption and separation purposes
Akala et al.	2003	Organic redox-initiated polymerization process for the fabrication of hydrogels for colon-specific drug delivery
Scott et al.	1999	Highly crosslinked, PEG-containing copolymers for sustained solute delivery
Shantha et al.	2000	Preparation and in-vitro evaluation of poly [N-vinyl-2-pyrrolidone-polyethylene glycol diacrylate]-chitosan interpolymeric pH-responsive hydrogels for oral drug delivery
DE69523044T2 (de)	2002-06-20	Block- und pfropfcopolymere und dazu gehöriges verfahren
US4279795A (en)	1981-07-21	Hydrophilic-hydrophobic graft copolymers for self-reinforcing hydrogels
Devine et al.	2005	Synthesis and characterisation of chemically crosslinked N-vinyl pyrrolidinone (NVP) based hydrogels
Dunn et al.	1954	The synthesis of block copolymers of styrene and methyl methacrylate
Karadağ et al.	2005	Water uptake in chemically crosslinked poly (acrylamide-co-crotonic acid) hydrogels
SE448545B (sv)	1987-03-02	Vattenabsorberande komposition och anvendning derav som berare for lekemedel eller som overdrag pa katetrar, suturer och glasytor
JPS60130638A (ja)	1985-07-12	ヒアルロン酸もしくはその塩で改質された重合体製品
DE2734298A1 (de)	1978-10-05	Verbesserte copolymerisate olefinisch ungesaettigter carbonsaeureverbindungen
París et al.	2009	Swelling behaviour of thermo-sensitive hydrogels based on oligo (ethylene glycol) methacrylates
Laquerbe et al.	2023	Supramolecular crosslinked hydrogels: Similarities and differences with chemically crosslinked hydrogels
Kamoun et al.	2018	Photopolymerized PVA-g-GMA hydrogels for biomedical applications: factors affecting hydrogel formation and bioevaluation tests
DE2528068A1 (de)	1976-01-08	Wasserunloesliche hydrophile copolymere
Fundueanu et al.	2010	Poly (vinyl alcohol) microspheres with pH-and thermosensitive properties as temperature-controlled drug delivery
Constantin et al.	2020	Smart drug delivery system activated by specific biomolecules
Kureha et al.	2022	Nanoscale structures of poly (oligo ethylene glycol methyl ether methacrylate) hydrogels revealed by small-angle neutron scattering
Levenfeld et al.	1991	Polymers with pharmacological activity, 5. Hydrolytical behaviour of polymethacrylic hydrogels bearing “paracetamol” side groups
Kayaman et al.	1997	Phase transition of polyacrylamide gels in PEG solutions
DE69325327T2 (de)	1999-12-16	Wasserabsorbierende Kontaktlinse
US3954966A (en)	1976-05-04	Infusion solutions and method of manufacturing same
CA1183994A (fr)	1985-03-12	Polymeres qui gonflent sous l'influence de l'eau