PL209477B1 - New nonlinear optics bi-functional polymers and methods of their manufacture - Google Patents
New nonlinear optics bi-functional polymers and methods of their manufactureInfo
- Publication number
- PL209477B1 PL209477B1 PL366954A PL36695404A PL209477B1 PL 209477 B1 PL209477 B1 PL 209477B1 PL 366954 A PL366954 A PL 366954A PL 36695404 A PL36695404 A PL 36695404A PL 209477 B1 PL209477 B1 PL 209477B1
- Authority
- PL
- Poland
- Prior art keywords
- sulfonyl
- phenyl
- amino
- diazenyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229920001002 functional polymer Polymers 0.000 title 1
- -1 5- ((4-nitrophenyl) sulfonyl) -1,3-thiazol-2-yl Chemical group 0.000 claims description 51
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 229920001519 homopolymer Polymers 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 230000001588 bifunctional effect Effects 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 5
- 229920000193 polymethacrylate Polymers 0.000 description 5
- 239000012634 fragment Substances 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku są nowe nieliniowo optyczne homopolimery bifunkcyjne, zawierające w strukturze chemicznej jednego meru heterocykliczne ugrupowania chromoforowe i fragment fotoprzewodzący oraz sposób wytwarzania nieliniowo optycznych homopolimerów bifunkcyjnych.The present invention relates to new nonlinear optical bifunctional homopolymers containing heterocyclic chromophore groups and a photoconductive fragment in the chemical structure of a single mer, and a method of producing nonlinear optical bifunctional homopolymers.
W literaturze naukowej i technicznej nie był y opisane bifunkcyjne homopolimery metakrylowe, będące przedmiotem wynalazku.The bifunctional methacrylic homopolymers, which are the subject of the invention, have not been described in the scientific and technical literature.
Wynalazek dotyczy nowych związków o wzorze 1, w którym R oznacza grupę 5((4-nitrofenylo)sulfonylo)-1,3-tiazol-2-ylową, 6-nitro-1,3-benzotiazol-2-ylową, (4[(1,3-tiazol-2-yl)amino]sulfonylo)fenylową, (4[(pirymidyn-2-yl)amino]sulfonylo)fenylową lub (4[(2,6-dimetylopirymidyn-4-yl)amino]sulfonylo)fenylową, a n wynosi od 5 do 50.The invention relates to new compounds of formula 1, in which R is a 5 ((4-nitrophenyl) sulfonyl) -1,3-thiazol-2-yl, 6-nitro-1,3-benzothiazol-2-yl, (4 [ (1,3-thiazol-2-yl) amino] sulfonyl) phenyl, (4 [(pyrimidin-2-yl) amino] sulfonyl) phenyl or (4 [(2,6-dimethylpyrimidin-4-yl) amino] sulfonyl ) phenyl, and n ranges from 5 to 50.
Bifunkcyjne homopolimery metakrylowe zawierają w strukturze chemicznej jednego meru zarówno ugrupowania chromoforowe jak i fragment fotoprzewodzący, przez co nadają się do wytwarzania nowych materiałów fotorefraktywnych, znajdujących zastosowanie w optyce nieliniowej.Bifunctional methacrylic homopolymers contain both chromophore groups and a photoconductive fragment in the chemical structure of a single mer, which makes them suitable for the production of new photorefractive materials applicable in nonlinear optics.
Nowe związki charakteryzują się tym, że są nierozpuszczalne w wodzie, rozpuszczalne w dostępnych rozpuszczalnikach organicznych, mogą być nanoszone metodą „spin-coating na powierzchnie ciał stałych, np. na metal lub szkło, gdzie tworzą trwałe warstwy.The new compounds are characterized by the fact that they are insoluble in water, soluble in available organic solvents, they can be applied using the "spin-coating" method on the surfaces of solid bodies, e.g. on metal or glass, where they create durable layers.
Sposób wytwarzania nowych nieliniowo optycznych homopolimerów bifunkcyjnych obejmuje reakcję polimeryzacji rodnikowej metakrylanu, wybranego z grupy obejmującej; metakrylan 2{3-((E)[4-{4-[(pirymidyn-2-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu. metakrylan 2{3-((E)[4-{4-[(2,6-dimetylopirydyn-4-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu, metakrylan 2{3-((E)[4-{4-[(1,3-tiazol-2-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu, metakrylan 2{3-[(E)-(6-nitro-1,3-benzotiazol-2-yl)diazenylo]-9H-karbazol-9-yl}etylu lub metakrylan 2{3-((E)-{5-[(4-nitrofenylo)sulfonylo]-1,3-tiazol-2-yl}diazenylo)-9H-karbazol-9-yl}etylu.The method of producing new nonlinearly optical bifunctional homopolymers comprises a radical polymerization reaction of a methacrylate selected from the group consisting of; 2 {3 - ((E) [4- {4 - [(pyrimidin-2-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl methacrylate. 2 {3 - ((E) [4- {4 - [(2,6-dimethylpyridin-4-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl methacrylate, methacrylate 2 {3 - ((E) [4- {4 - [(1,3-thiazol-2-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl methacrylate 2 {3 - [(E ) - (6-nitro-1,3-benzothiazol-2-yl) diazenyl] -9H-carbazol-9-yl} ethyl or methacrylate 2 {3 - ((E) - {5 - [(4-nitrophenyl) sulfonyl ] -1,3-thiazol-2-yl} diazenyl) -9H-carbazol-9-yl} ethyl.
Sposób według wynalazku polega na tym, że metakrylan 2{3-((E)[4-{4-[(pirymidyn-2-yl)-amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu, lub metakrylan 2{3-((E)[4-{4-[(2,6-dimetylopirydyn-4-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu, metakrylan 2{3-((E)[4-{4-[(1,3-tiazol-2yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu lub metakrylan 2{3-[(E)-(6-nitro-1,3-benzotiazol-2-yl)diazenylo]-9H-karbazol-9-yl}etylu lub metakrylan 2{3-((E)-{5-[(4-nitrofenylo)sulfonylo]-1,3-tiazol-2-yl}diazenylo)-9H-karbazol-9-yl}etylu poddaje się reakcji homopolimeryzacji w środowisku mieszaniny tetrahydrofuranu i γ-butyrolaktanu w obecności azoizobutyronitrylu (AIBN) jako inicjatora. Otrzymane produkty reakcji homopolimeryzacji po wydzieleniu z mieszaniny poreakcyjnej i wysuszeniu, oczyszcza się poprzez krystalizację z metanolu.The process of the invention consists in that 2 {3 - ((E) [4- {4 - [(pyrimidin-2-yl) -amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl methacrylate , or 2 {3 - ((E) [4- {4 - [(2,6-dimethylpyridin-4-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl methacrylate, 2 {3 - ((E) [4- {4 - [(1,3-thiazol-2-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl or 2 {3 - [(E ) - (6-nitro-1,3-benzothiazol-2-yl) diazenyl] -9H-carbazol-9-yl} ethyl or methacrylate 2 {3 - ((E) - {5 - [(4-nitrophenyl) sulfonyl ] -1,3-thiazol-2-yl} diazenyl) -9H-carbazol-9-yl} ethyl is homopolymerized in a mixture of tetrahydrofuran and γ-butyrolactan in the presence of azoisobutyronitrile (AIBN) as initiator. The obtained homopolymerization reaction products, after separation from the reaction mixture and drying, are purified by crystallization from methanol.
Zasadnicze korzyści wynikające z wynalazku polegają na możliwości otrzymania w prosty sposób bifunkcyjnych polimerów metakrylowych, zawierających w strukturze chemicznej jednego meru zarówno ugrupowania chromoforowe jak i fragment fotoprzewodzący.The main advantages of the invention consist in the possibility of obtaining in a simple manner bifunctional methacrylic polymers containing both chromophore groups and a photoconductive fragment in the chemical structure of a single mer.
Przedmiot wynalazku przedstawiony jest w przykładach wykonania.The subject matter of the invention is illustrated in the following examples.
P r z y k ł a d IP r z k ł a d I
Sposobem według wynalazku homopolimer o wzorze 1, w którym R oznacza grupę 5[(4-nitrofenylo)sulfonylo]-1,3-tiazol-2-ylową, a n wynosi 15, wytwarza się z 2 g (0,0035 mola) metakrylanu 2{3-((E)-{5-[(4-nitrofenylo)sulfonylo]-1,3-tiazol-2-yl}diazenylo)-9H-karbazol-9-yl}etylu, stosując 0,2 g (10% wag. monomeru) dodatek inicjatora azoizobutyronitrylu-(AIBN), który rozpuszcza się w 30 cm3 świeżo przygotowanej w stosunku objętościowym 7:3 mieszaniny rozpuszczalników: osuszonego nad sitami 4A tetrahydrofuranu i γ-butyrolakton, i ogrzewa, pod chłodnicą zwrotną w atmosferze azotu przez 72 godziny. Po tym czasie mieszaninę poreakcyjną wylewa się do zlewki z wodą i pozostawia na kilka tygodni, zmieniając co jakiś czas wodę, aż do stwardnienia osadu. Stwardniały osad suszy się na powietrzu, rozdrabnia, a następnie suszy ponownie w temperaturze 40-50°C. Polimer oczyszcza się z nieprzereagowanych monomerów przez ponowne rozpuszczenie w 30 cm3 tetrahydrofuranu i wylanie do metanolu lub etanolu. Wydzielony w postaci proszku, barwny produkt odsącza się i jak poprzednio, suszy w temperaturze 40-50°C.According to the process of the invention, the homopolymer of formula 1, wherein R is 5 [(4-nitrophenyl) sulfonyl] -1,3-thiazol-2-yl, and n is 15, is prepared from 2 g (0.0035 mol) of methacrylate {3 - ((E) - {5 - [(4-nitrophenyl) sulfonyl] -1,3-thiazol-2-yl} diazenyl) -9H-carbazol-9-yl} ethyl using 0.2 g (10 % by weight of monomer) addition of azoisobutyronitrile- (AIBN) initiator, which is dissolved in 30 cm 3 of a freshly prepared 7: 3 by volume mixture of solvents: tetrahydrofuran and γ-butyrolactone dried over 4A sieves, and heated under reflux under nitrogen atmosphere for 72 hours. After this time, the reaction mixture is poured into a beaker with water and left for several weeks, changing the water periodically until the precipitate hardens. The hardened sediment is air-dried, ground and then dried again at 40-50 ° C. The polymer is purified from the unreacted monomers by re-dissolution in 30 cm 3 of tetrahydrofuran and pouring into methanol or ethanol. The colored product separated as a powder is filtered off and, as before, dried at 40-50 ° C.
Ogólna wydajność otrzymanego polimetakrylanu 2{3-((E)-{5-[(4-nitrofenylo)sulfonylo]-1,3-tiazol2-yl}diazenylo)-9H-karbazol-9-yl}etylu) wynosi 82%. Temperatura zeszklenia otrzymanego polimeru wynosi 77°C.The overall yield of the obtained 2 {3 - ((E) - {5 - [(4-nitrophenyl) sulfonyl] -1,3-thiazol-2-yl} diazenyl) -9H-carbazol-9-yl} ethyl polymethacrylate) is 82%. The glass transition temperature of the obtained polymer is 77 ° C.
PL 209 477 B1PL 209 477 B1
P r z y k ł a d IIP r z x l a d II
Homopolimer o wzorze 1, w którym R oznacza grupę 6-nitro-1.3-benzotiazol-2-ylową, a n wynosi 12, wytwarza się z 2 g (0,0041 mola) metakrylanu 2{3-[(E)-(6-nitro-1.3-benzotiazol-2-yl)diazenylo]-9H-karbazol-9-yl}etylu, zgodnie z przykładem I.The homopolymer of formula I, in which R is 6-nitro-1,3-benzothiazol-2-yl and n is 12, is prepared from 2 g (0.0041 mol) of methacrylate 2 {3 - [(E) - (6- nitro-1,3-benzothiazol-2-yl) diazenyl] -9H-carbazol-9-yl} ethyl according to example I.
Ogólna wydajność otrzymanego polimetakrylanu 2{3-[(E)-(6-nitro-1.3-benzotiazol-2-yl)diazenylo]-9H-karbazol-9-yl}etylu) wynosi 97,6%. Temperatura zeszklenia otrzymanego polimeru wynosi 104°C.The overall yield of the obtained 2 (3 - [(E) - (6-nitro-1,3-benzothiazol-2-yl) diazenyl] -9H-carbazol-9-yl} ethyl polymethacrylate) is 97.6%. The glass transition temperature of the obtained polymer is 104 ° C.
P r z y k ł a d IIIP r z x l a d III
Homopolimer o wzorze 1, w którym R oznacza grupę (4[(1,3-tiazol-2-yl)amino]sulfonylo)fenylową, a n wynosi 21. wytwarza się z 2 g (0.0036 mola) metakrylanu 2{3-((E)[4-{4-[(1,3-tiazol-2-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu, zgodnie z przykładem I.Homopolymer of formula 1, where R is (4 [(1,3-thiazol-2-yl) amino] sulfonyl) phenyl, and n is 21. Prepared from 2 g (0.0036 mol) of methacrylate 2 {3 - (( E) [4- {4 - [(1,3-thiazol-2-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl as in example I.
Ogólna wydajność otrzymanego opisanym sposobem polimetakrylanu 2{3-((E)[4-{4-[(1.3-tiazol-2-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu) wynosi 78,8%. Temperatura zeszklenia otrzymanego polimeru wynosi 131°C.The overall yield of the 2 {3 - ((E) [4- {4 - [(1,3-thiazol-2-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl polymethacrylate) obtained as described above is 78.8%. The glass transition temperature of the obtained polymer is 131 ° C.
P r z y k ł a d IVP r x l a d IV
Homopolimer o wzorze przestawionym na rysunku, w którym R oznacza grupę (4[(pirymidyn-2-yl)amino]sulfonylo)fenylową. a n wynosi 40, wytwarza się z 2 g (0,0037 mola) metakrylanu 2{3-((E)[4-{4-[(pirymidyn-2-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu, zgodnie z przykładem I.A homopolymer of the formula shown in the figure wherein R is (4 [(pyrimidin-2-yl) amino] sulfonyl) phenyl. and n is 40, prepared from 2 g (0.0037 mol) of 2 {3 - ((E) [4- {4 - [(pyrimidin-2-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazole methacrylate -9-yl} ethyl according to example I.
Ogólna wydajność otrzymanego polimetakrylanu 2{3-((E)[4-{4-[(pirymidyn-2-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu) wynosi 99%. Temperatura zeszklenia otrzymanego polimeru wynosi 86°C.The overall yield of the obtained 2 {3 - ((E) [4- {4 - [(pyrimidin-2-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl polymethacrylate) is 99%. The glass transition temperature of the obtained polymer is 86 ° C.
P r z y k ł a d VP r z k ł a d V
Homopolimer o wzorze 1, w którym R oznacza grupę (4[(2,6-dimetylopirymidyn-4-yl)amino]sulfonylo)fenylową, a n wynosi 50, wytwarza się z 2 g (0.0037 mola) metakrylanu 2{3-((E)[4-{4-[(2,6-dimetylopirydyn-4-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu, zgodnie z przykładem I.The homopolymer of formula I, in which R is (4 [(2,6-dimethylpyrimidin-4-yl) amino] sulfonyl) phenyl, n is 50, is prepared from 2 g (0.0037 mol) 2 {3 - ((( E) [4- {4 - [(2,6-dimethylpyridin-4-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl as in example I.
Ogólna wydajność otrzymanego polimetakrylanu 2{3-((E)[4-{4-[(2,6-dimetylopirydyn-4-yl)amino]sulfonylo}fenylo]diazenylo)-9H-karbazol-9-yl}etylu) wynosi 98,6%. Temperatura zeszklenia otrzymanego polimeru wynosi 115°C.The overall yield of the obtained 2 {3 - ((E) [4- {4 - [(2,6-dimethylpyridin-4-yl) amino] sulfonyl} phenyl] diazenyl) -9H-carbazol-9-yl} ethyl polymethacrylate) is 98.6%. The glass transition temperature of the obtained polymer is 115 ° C.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL366954A PL209477B1 (en) | 2004-04-05 | 2004-04-05 | New nonlinear optics bi-functional polymers and methods of their manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL366954A PL209477B1 (en) | 2004-04-05 | 2004-04-05 | New nonlinear optics bi-functional polymers and methods of their manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL366954A1 PL366954A1 (en) | 2005-10-17 |
| PL209477B1 true PL209477B1 (en) | 2011-09-30 |
Family
ID=36645135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL366954A PL209477B1 (en) | 2004-04-05 | 2004-04-05 | New nonlinear optics bi-functional polymers and methods of their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL209477B1 (en) |
-
2004
- 2004-04-05 PL PL366954A patent/PL209477B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL366954A1 (en) | 2005-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5240798B2 (en) | Refractive index improver, and resin composition, polymerization or curable composition and optical material containing the same | |
| US5359085A (en) | Fulgimide derivatives | |
| EP0728754B1 (en) | Coumarin derivatives, method for their preparation and their use as intermediates | |
| RU2012122591A (en) | METHOD FOR PRODUCING HOLOGRAPHIC MEDIA | |
| Deng et al. | Regio-and stereoselective construction of stimuli-responsive macromolecules by a sequential coupling-hydroamination polymerization route | |
| Yİldİko et al. | Investigation of novel diethanolamine dithiocarbamate agent for RAFT polymerization: DFT computational study of the oligomer molecules | |
| PL209477B1 (en) | New nonlinear optics bi-functional polymers and methods of their manufacture | |
| Nguyen et al. | Controlled radical polymerization of a trialkylsilyl methacrylate by reversible addition–fragmentation chain transfer polymerization | |
| EP2516477A1 (en) | Novel initiation method for polymerizing (meth)acrylates | |
| US20220380541A1 (en) | Dual-cure method and system for fabrication of 3d polymeric structures cross-reference to earlier applications | |
| DE19521503A1 (en) | Polymerizable azo dyes with a thiophene structure | |
| KR20020044134A (en) | Optical material and optical part each containing aromatic sulfide compound and aromatic sulfide compound | |
| PL209488B1 (en) | New nonlinear optics bi-functional copolymers and methods of their manufacture | |
| JP5594482B2 (en) | Method for producing hyperbranched polymer | |
| JP7159152B2 (en) | triarylmethane compounds | |
| JPS59135206A (en) | Low water-absorbing polymer with high optical and mechanicalproperties, manufacture, forming material, and manufacture of carrier for light reading infomation and plate for light reading infomation memory | |
| JP5534244B2 (en) | Method for producing hyperbranched polymer | |
| JPH0578570B2 (en) | ||
| JPH05310655A (en) | Cyclobutenedione derivative containing polymerizable double bond its homo-or copolymer and nonlinear optical element using the same | |
| CN102190755B (en) | Quaternary random copolymer and synthesis method thereof | |
| JP2023152032A (en) | Electro-optic compositions, polymer compounds, compounds, electro-optic films, and electro-optic elements | |
| JP2002236222A (en) | Optical material and optical parts which use aromatic sulfide compound and aromatic sulfide compound | |
| US7250121B2 (en) | Non-linear optical device material composition | |
| PL203038B1 (en) | Method of manufacture of chromophore methacrylic copolymers with diazenyl group in polymer lateral chain | |
| PL213155B1 (en) | Photochromic homopolymers and process for the preparation thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20070405 |