PL209843B1 - Polymerization photinitiating composition - Google Patents
Polymerization photinitiating compositionInfo
- Publication number
- PL209843B1 PL209843B1 PL386711A PL38671108A PL209843B1 PL 209843 B1 PL209843 B1 PL 209843B1 PL 386711 A PL386711 A PL 386711A PL 38671108 A PL38671108 A PL 38671108A PL 209843 B1 PL209843 B1 PL 209843B1
- Authority
- PL
- Poland
- Prior art keywords
- composition
- polymerization
- photinitiating
- dithiophenanthropteridine
- concentration
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 22
- 238000006116 polymerization reaction Methods 0.000 title claims description 5
- 239000006100 radiation absorber Substances 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 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
- 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
- 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
- 229910052786 argon Inorganic materials 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
Opis wynalazkuDescription of the invention
Wynalazek dotyczy kompozycji fotoinicjującej polimeryzację, zwłaszcza dla potrzeb stomatologii, poligrafii, stereolitografii oraz produkcji lakierów i klejów fotoutwardzalnych.The invention relates to a polymerization photoinitiating composition, especially for the purposes of dentistry, printing, stereolithography and the production of photocurable varnishes and adhesives.
Z literatury znane są kompozycje światłoczułe zawierające w swym składzie absorber promieniowania i donor elektronukoinicjator.Photosensitive compositions containing in their composition a radiation absorber and an electron 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, czwartorzędowe sole boru, kwas tiofenoksyoctowy, kwas fenoksyoctowy i N-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 kompozycje 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-ditiofenantropterydynę o wzorze 1.According to the essential features of the invention, the composition is characterized in that it comprises an 11,13-dithiophenanthropteridine radiation absorber of 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-Ditiofenantropterydyna ma szerokie pasmo absorpcji światła, co umożliwia stosowanie różnych rodzajów źródeł promieniowania, w tym lamp stosowanych w stomatologii.11,13-Dithiophenanthropteridine 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 wedł ug wynalazku wyeliminowano drugi skł adnik koinicjator, dodawany w stężeniu około 0,1 mol/dm3.In the composition according to the invention, the second co-initiator component added at a concentration of about 0.1 mol / dm 3 was eliminated.
P r z y k ł a d IP r z k ł a d I
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu pentaerytrytolu, około 5% 1-metylo-2-pirolidonu i 11,13-ditiofenantropterydynę o stężeniu 1 x 10-3 mol/dm3 naświetlano promieniowaniem o natężeniu 50 mW/cm2 emitowanym przez lampę dentystyczną. Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer.A monomer composition with a thickness of 3 mm containing about 95% pentaerythritol triacrylate, about 5% 1-methyl-2-pyrrolidone and 11,13-dithiophenanthropteridine at a concentration of 1 x 10 -3 mol / dm 3 was irradiated with 50 mW / cm 2 radiation. emitted by a dental lamp. After a few seconds, the liquid composition is observed to solidify into a glassy polymer.
P r z y k ł a d IIP r z x l a d II
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu pentaerytrytolu, około 5% 1-metylo-2-pirolidonu i 11,13-ditiofenantropterydynę o stężeniu 1 x 10-3 mol/dm3 naświetlano promieniowaniem 351 i 363 nm emitowanym przez laser argonowy o natężeniu 50 mW/cm2. Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer.A monomer composition with a thickness of 3 mm containing about 95% pentaerythritol triacrylate, about 5% 1-methyl-2-pyrrolidone and 11,13-dithiophenanthropteridine at a concentration of 1 x 10 -3 mol / dm 3 was irradiated with 351 and 363 nm radiation emitted by a laser argon with an intensity of 50 mW / cm 2 . After a few seconds, the liquid composition is observed to solidify into a glassy polymer.
P r z y k ł a d IIIP r x l a d III
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu 2-etylo2-hydroksymetylo-1,3-propanodiolu, około 5% 1-metylo-2-pirolidonu i 11,13-ditiofenantropterydynę o stężeniu 1 x 10-3 mol/dm3 naświetlano promieniowaniem o natężeniu 50 mW/cm2 emitowanym przez lampę dentystyczną. Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer.3 mm thick monomer composition containing approximately 95% 2-ethyl-2-hydroxymethyl-1,3-propanediol triacrylate, approximately 5% 1-methyl-2-pyrrolidone and 11,13-dithiophenanthropteridine at a concentration of 1 x 10 -3 mol / dm 3 was irradiated with 50 mW / cm 2 radiation emitted by a dental lamp. After a few seconds, the liquid composition is observed to solidify into a glassy polymer.
P r z y k ł a d IVP r x l a d IV
Monomerową kompozycję o grubości warstwy 3 mm zawierającą około 95% triakrylanu 2-etylo2-hydroksymetylo-1,3-propanodiolu, około 5% 1-metylo-2-pirolidonu i 11,13-ditiofenantropterydynę o stężeniu 1 x 10-3 mol/dm3 naś wietlano promieniowaniem 351 i 363 nm emitowanym przez laser argonowy o natężeniu 50 mW/cm2. Po kilku sekundach obserwuje się zestalenie ciekłej kompozycji w szklisty polimer.3 mm thick monomer composition containing approximately 95% 2-ethyl-2-hydroxymethyl-1,3-propanediol triacrylate, approximately 5% 1-methyl-2-pyrrolidone and 11,13-dithiophenanthropteridine at a concentration of 1 x 10 -3 mol / dm 3 was irradiated with light 351 and 363 nm emitted by an argon laser with intensity 50 mW / cm 2 . 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 |
|---|---|---|---|
| PL386711A PL209843B1 (en) | 2008-12-06 | 2008-12-06 | Polymerization photinitiating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL386711A PL209843B1 (en) | 2008-12-06 | 2008-12-06 | Polymerization photinitiating composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL386711A1 PL386711A1 (en) | 2010-06-07 |
| PL209843B1 true PL209843B1 (en) | 2011-10-31 |
Family
ID=42990477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL386711A PL209843B1 (en) | 2008-12-06 | 2008-12-06 | Polymerization photinitiating composition |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL209843B1 (en) |
-
2008
- 2008-12-06 PL PL386711A patent/PL209843B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL386711A1 (en) | 2010-06-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20111206 |