PL221776B1 - Polymerization photoinitiating composition - Google Patents
Polymerization photoinitiating compositionInfo
- Publication number
- PL221776B1 PL221776B1 PL398202A PL39820212A PL221776B1 PL 221776 B1 PL221776 B1 PL 221776B1 PL 398202 A PL398202 A PL 398202A PL 39820212 A PL39820212 A PL 39820212A PL 221776 B1 PL221776 B1 PL 221776B1
- Authority
- PL
- Poland
- Prior art keywords
- composition
- methylthio
- polymerization
- mol
- photoinitiating composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 22
- 238000006116 polymerization reaction Methods 0.000 title claims description 5
- PQSWGBHAOFKIHK-UHFFFAOYSA-N CSC1=CC(C=CC=C2)=C2C2=C1C1=NC(C(SC)=NC=N3)=C3N=C1C=C2 Chemical compound CSC1=CC(C=CC=C2)=C2C2=C1C1=NC(C(SC)=NC=N3)=C3N=C1C=C2 PQSWGBHAOFKIHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000006100 radiation absorber Substances 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 3
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 3
- 229930006711 bornane-2,3-dione Natural products 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 2
- FOXXZZGDIAQPQI-XKNYDFJKSA-N Asp-Pro-Ser-Ser Chemical compound OC(=O)C[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(O)=O FOXXZZGDIAQPQI-XKNYDFJKSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical group OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- MOTOSAGBNXXRRE-UHFFFAOYSA-N 2-phenylsulfanylacetic acid Chemical group OC(=O)CSC1=CC=CC=C1 MOTOSAGBNXXRRE-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241001464161 Gortyna xanthenes Species 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical group OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
Landscapes
- Dental Preparations (AREA)
Description
Wynalazek dotyczy kompozycji fotoinicjującej polimeryzację, zwłaszcza dla potrzeb stomatologii, poligrafii, stereolitografii oraz produkcji lakierów i klejów fotoutwardzalnych.The invention relates to a photoinitiating polymerization composition, especially for the purposes of dentistry, printing, stereolithography and the production of photo-curable varnishes and adhesives.
Z literatury znane są kompozycje światłoczułe zawierające w swym składzie absorber promieniowania i donor elektronu-koinicjator.Photosensitive compositions containing in their composition a radiation absorber and an electron donor-co-initiator are known from the literature.
Należą do nich kompozycje zawierające barwniki akrydynowe, ksantenowe, tiazynowe, cyjaninowe, czy też kamforochinon oraz jako donory elektronów aminy aromatyczne lub alifatyczne, czwa rtorzędowe sole boru, kwas tiofenoksyoctowy, kwas fenoksyoctowy i W-fenyloglicyna.These include compositions containing acridine, xanthene, thiazine, cyanine dyes, or camphorquinone, and as electron donors, aromatic or aliphatic amines, quaternary boron salts, thiophenoxyacetic acid, phenoxyacetic acid and N-phenylglycine.
Znane kompozycje fotoinicjujące polimeryzację charakteryzują się ograniczoną trwałością ciemną gotowych mieszanin polimeryzujących jak np. barwniki ksantenowe oraz ograniczoną możliwość stosowania tylko w bardzo cienkich warstwach np. barwniki cyjaninowe. Ponadto ko mpozycje wymagają, jako koinicjatorów stosowania kosztownych donorów elektronu dla barwników cyjaninowych.Known photoinitiating polymerization compositions are characterized by a limited dark stability of the finished polymerization mixtures, such as e.g. xanthene dyes, and a limited possibility of using only very thin layers, e.g. cyanine dyes. In addition, the compositions require the use of expensive electron donors for the cyanine dyes as co-initiators.
Według istotnych cech wynalazku kompozycja charakteryzuje się tym, że zawiera absorber promieniowania 11,13-di(metylotio)fenantropterydynę o wzorze 1.According to the essential features of the invention, the composition is characterized in that it comprises a radiation absorber 11,13-di (methylthio) phenanthropteridine of the formula 1.
Kompozycja według wynalazku ma dużą trwałość w czasie przechowywania, a podczas naświetlania czułość porównywalną z kompozycją zawierającą kamforochinon.The composition according to the invention has a high storage stability and a sensitivity during irradiation comparable to a composition containing camphorquinone.
11,13-Di(metylotio)fenantropterydyna ma szerokie pasmo absorpcji światła, co umożliwia stosowanie różnych rodzajów źródeł promieniowania, w tym lamp stosowanych w stomatologii.11,13-Di (methylthio) phenanthropteridine has a wide light absorption band, which allows the use of various types of radiation sources, including lamps used in dentistry.
Kompozycja według wynalazku zawiera absorber promieniowania o stężeniu około 200 razy mniejszym od stężenia kamforochinonu.The composition according to the invention contains a radiation absorber at a concentration approximately 200 times lower than that of the camphorquinone.
W kompozycji według wynalazku wyeliminowano drugi składnik koinicjator, dodawany w stężeniu około 0,1 mol/dm .The second component, co-initiator, added at a concentration of about 0.1 mol / dm, was eliminated in the composition of the invention.
Przykła d 1Example d 1
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu pentaerytrytolu, około 5% 1-metylo-2-pirolidonu i 11,13-di(metylotio)fenantropterydynę o stężeniu 2x10- mol/dm naświetlano promieniowaniem o natężeniu 50 mW/cm emitowanym przez lampę dentystyczną. Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer.The monomer composition having a thickness of 3 mm comprising about 95% pentaerythritol triacrylate, about 5% 1-methyl-2-pyrrolidone and 11,13-di (methylthio) fenantropterydynę a concentration of 2x10 - mol / liter was irradiated with an intensity of 50 mW / cm emitted by a dental lamp. After a few seconds, the liquid composition is observed to solidify into a glassy polymer.
Przykła d 2Example d 2
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu pentaerytrytolu, około 5% 1-metylo-2-pirolidonu i 11,13-di(metylotio)fenantropterydynę o stężeniu3 mm thick monomer composition containing about 95% pentaerythritol triacrylate, about 5% 1-methyl-2-pyrrolidone and 11,13-di (methylthio) phenanthropteridine at a concentration of
-3 3-3 3
2x10- mol/dm naświetlano promieniowaniem emitowanym przez laser diodowy DPSS MBL-F-457s 2 o natężeniu 50 mW/cm2. Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer.2x10 - mol / dm was irradiated with the radiation emitted by the DPSS MBL-F-457s 2 diode laser at the intensity of 50 mW / cm 2 . After a few seconds, the liquid composition is observed to solidify into a glassy polymer.
Przykła d 3Example d 3
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu 2-etylo-2-hydroksymetylo-1,3-propanodiolu, około 5% 1-metylo-2-pirolidonu i 11,13-di(metylotio)fenan-3 3 2 tropterydynę o stężeniu 2x10- mol/dm naświetlano promieniowaniem o natężeniu 50 mW/cm emitowanym przez lampę dentystyczną. Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer3 mm thick monomer composition containing about 95% 2-ethyl-2-hydroxymethyl-1,3-propanediol triacrylate, about 5% 1-methyl-2-pyrrolidone and 11,13-di (methylthio) phenan-3 3 2 2x10- mol / dm tropteridine was irradiated with 50 mW / cm radiation emitted by a dental lamp. After a few seconds, the liquid composition is observed to solidify into a glassy polymer
Przykład 4Example 4
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu 2-etylo-2-hydroksymetylo-1,3-propanodiolu, około 5% 1-metylo-2-pirolidonu i 11,13-di(metylotio)fenan-3 3 tropterydynę o stężeniu 2x10-3 mol/dm3 naświetlano promieniowaniem emitowanym przez laser dio2 dowy DPSS MBL-F-457s o natężeniu 50 mW/cm . Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer.3 mm thick monomer composition containing about 95% 2-ethyl-2-hydroxymethyl-1,3-propanediol triacrylate, about 5% 1-methyl-2-pyrrolidone and 11,13-di (methylthio) phenan-3 3 tropteridine at a concentration of 2x10 -3 mol / dm 3 was irradiated radiation emitted by the laser dio 2 dowy DPSS MBL-F-457s intensity of 50 mW / cm. After a few seconds, the liquid composition is observed to solidify into a glassy polymer.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL398202A PL221776B1 (en) | 2012-02-22 | 2012-02-22 | Polymerization photoinitiating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL398202A PL221776B1 (en) | 2012-02-22 | 2012-02-22 | Polymerization photoinitiating composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL398202A1 PL398202A1 (en) | 2013-09-02 |
| PL221776B1 true PL221776B1 (en) | 2016-05-31 |
Family
ID=49036166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL398202A PL221776B1 (en) | 2012-02-22 | 2012-02-22 | Polymerization photoinitiating composition |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221776B1 (en) |
-
2012
- 2012-02-22 PL PL398202A patent/PL221776B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL398202A1 (en) | 2013-09-02 |
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