PL397314A1 - Process for the preparation of the dimethacrylated resin, especially for bone cement - Google Patents
Process for the preparation of the dimethacrylated resin, especially for bone cementInfo
- Publication number
- PL397314A1 PL397314A1 PL397314A PL39731411A PL397314A1 PL 397314 A1 PL397314 A1 PL 397314A1 PL 397314 A PL397314 A PL 397314A PL 39731411 A PL39731411 A PL 39731411A PL 397314 A1 PL397314 A1 PL 397314A1
- Authority
- PL
- Poland
- Prior art keywords
- stage
- bone cement
- resin
- dianhydro
- sorbitol
- Prior art date
Links
- 239000011347 resin Substances 0.000 title abstract 3
- 229920005989 resin Polymers 0.000 title abstract 3
- 239000002639 bone cement Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- -1 (2-hydroxy-3-methacryloxy) propoxy Chemical group 0.000 abstract 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 abstract 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 abstract 1
- 229910052939 potassium sulfate Inorganic materials 0.000 abstract 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 229960002920 sorbitol Drugs 0.000 abstract 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials For Medical Uses (AREA)
- Dental Preparations (AREA)
Abstract
Sposób otrzymywania zywicy dimetakrylanowej zwlaszcza do cementu kostnego polega na tym, ze wykorzystuje sie 1,4:3,6-dianhydro-D-sorbitol (izosorbit), który w pierwszym etapie przeksztalca sie w eter diallilowy w reakcji eteryfikacji Williamsona z wykorzystaniem nadmiaru bromku allilu, korzystnie w temperaturze jego wrzenia, i stezonego wodnego roztworu zasady oraz katalitycznej ilosci katalizatora przeniesienia fazowego korzystnie bromku tetrabutyloamoniowego, który to eter diallilowy w drugim etapie przeksztalca sie w eter diglicydylowy z wykorzystaniem nadmiaru utleniacza, korzystnie utleniacza nieorganicznego o wzorze 2KHSO5 • KHSO4 • K2SO4, oraz acetonu i wodnego roztworu NaHCO3 w temperaturze do 50°C, który to eter diglicydylowy w trzecim etapie poddaje sie reakcji z kwasem metakrylowym, korzystnie z jego stechiometryczna iloscia w temperaturze do 150°C, i tym samym otrzymuje sie zywice dimetakrylanowa, której glównym skladnikiem jest 2,5-bis(2-hydroksy-3-metakryloksypropoksy)-1,4:3,6-dianhydro-D-sorbitol o wzorze 1.The method of obtaining dimethacrylate resin, especially for bone cement, is that 1,4: 3,6-dianhydro-D-sorbitol (isosorbitol) is used, which in the first stage transforms into diallyl ether in the Williamson etherification reaction using excess allyl bromide , preferably at its boiling point, and a concentrated aqueous base solution and a catalytic amount of phase transfer catalyst, preferably tetrabutylammonium bromide, which diallyl ether is transformed into diglycidyl ether in the second stage using an excess of oxidant, preferably an inorganic oxidant with the formula 2KHSO5 • KHSO4 • K2SO4 and acetone and an aqueous NaHCO3 solution at a temperature of up to 50 ° C, which diglycidyl ether in the third stage is reacted with methacrylic acid, preferably with its stoichiometric amount at a temperature of up to 150 ° C, and thus a dimethacrylate resin, the main component of which is obtained is 2,5-bis (2-hydroxy-3-methacryloxy) propoxy) -1.4: 3,6-dianhydro-D-sorbitol of formula 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL397314A PL216356B1 (en) | 2011-12-09 | 2011-12-09 | Process for the preparation of the dimethacrylated resin, especially for bone cement |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL397314A PL216356B1 (en) | 2011-12-09 | 2011-12-09 | Process for the preparation of the dimethacrylated resin, especially for bone cement |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL397314A1 true PL397314A1 (en) | 2013-06-10 |
| PL216356B1 PL216356B1 (en) | 2014-03-31 |
Family
ID=48539616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL397314A PL216356B1 (en) | 2011-12-09 | 2011-12-09 | Process for the preparation of the dimethacrylated resin, especially for bone cement |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL216356B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025058466A1 (en) * | 2023-09-14 | 2025-03-20 | 한국화학연구원 | Isosorbide-based diepoxide compound and method for preparing same |
-
2011
- 2011-12-09 PL PL397314A patent/PL216356B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL216356B1 (en) | 2014-03-31 |
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