CS202829B1 - Process for preparing photodegradative polymers - Google Patents
Process for preparing photodegradative polymers Download PDFInfo
- Publication number
- CS202829B1 CS202829B1 CS781978A CS781978A CS202829B1 CS 202829 B1 CS202829 B1 CS 202829B1 CS 781978 A CS781978 A CS 781978A CS 781978 A CS781978 A CS 781978A CS 202829 B1 CS202829 B1 CS 202829B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- polymer
- yield
- benzene
- cyclopentylacrylphenone
- contained
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- GKXNNMODLAPXLF-UHFFFAOYSA-N C1(CCCC1)C1=CC=C(C=C1)C(C=C)=O Chemical compound C1(CCCC1)C1=CC=C(C=C1)C(C=C)=O GKXNNMODLAPXLF-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000006862 quantum yield reaction Methods 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- NGQRTGLTVZALAJ-UHFFFAOYSA-N C=1C=CC=CC=1C(=O)C=CC1CCCC1 Chemical compound C=1C=CC=CC=1C(=O)C=CC1CCCC1 NGQRTGLTVZALAJ-UHFFFAOYSA-N 0.000 claims description 2
- -1 cyclopentylacrylphenone Chemical compound 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000003708 ampul Substances 0.000 claims 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 1
- 206010034972 Photosensitivity reaction Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229960004217 benzyl alcohol Drugs 0.000 claims 1
- 230000027455 binding Effects 0.000 claims 1
- 238000009739 binding Methods 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- JFHJOMSTWVDDHW-UHFFFAOYSA-N methyl prop-2-enoate;prop-2-enenitrile Chemical compound C=CC#N.COC(=O)C=C JFHJOMSTWVDDHW-UHFFFAOYSA-N 0.000 claims 1
- 239000005022 packaging material Substances 0.000 claims 1
- 230000036211 photosensitivity Effects 0.000 claims 1
- 229920002959 polymer blend Polymers 0.000 claims 1
- 239000010453 quartz Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
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- Biological Depolymerization Polymers (AREA)
Description
Československa SOCIALISTICKÁ REPUBLIKA (19) POPIS VYNALEZU K AUTORSKÉMU OSVEDČENIU 202829 (11) (Bl) (51) Int. Cl.3 C 08 F 18/36 (22) Přihlášené 29 11 78(21) (PV 7819-78) 0ŘAD PRO VYNÁLEZY (40) Zverejnené 30 05 80 (45) Vydané 15 03 82 A OBJEVY (75,)Czechoslovakia SOCIALIST REPUBLIC (19) DESCRIPTION FOLLOWING COPYRIGHT CERTIFICATE 202829 (11) (Bl) (51) Int. Cl.3 C 08 F 18/36 (22) Entries 29 11 78 (21) (PV 7819-78) DISCUSSION ORDER (40) Published 30 05 80 (45) Published 15 03 82 A DISCOVERIES (75,)
Autor vynálezuThe inventor
LUKÁČ IVAN ing. CSc., BRATISLAVA, CHMELA ŠTEFAN prom. chem., NITRA,ZVARA IVAN ing, BRATISLAVA a HRDLOVIČ PAVOL RNDr. CSc, MALACKY (54) Sposob přípravy fotodegradatívnych polymérovLUKÁČ IVAN ing. CSc., BRATISLAVA, CHMELA ŠTEFAN prom. chem., NITRA, ZVARA IVAN ing, BRATISLAVA and HRDLOVIC PAVOL RNDr. CSc, MALACKY (54) Preparation of photodegradative polymers
Vynález sa týká spósobu přípravy fotodegra-datívnych polymérov, ktoré sa získajú polyme-rizáciou p-cyklopentyl akrylofenónu (I)BACKGROUND OF THE INVENTION The present invention relates to a process for preparing photodegradable polymers obtained by polymerizing p-cyclopentyl acrylophenone (I).
CHj-CH samotného, alebo jeho kopolymerizáciou s vlny-lovými monomérmi.CH 3 -CH alone, or by copolymerizing it with wool-like monomers.
Polymery obsahujúce p-cyklopentylakrylofe-nónové štruktúrne jednotky oproti nesubstituo-vaným (NSR patent č. 2. 119 855) a tiež oprotip-metoxyakrylofenónovým štruktúrnym jednot-kám (čs. autorské osvedčenie č. 170397) májávyššie kvantové výtažky trhania hlavných va-zieb. Oproti derivátom chalkónového typu, u kto-rého sú chráněné len kopolyméry so styrénom(čs. AO 185365) ich výhodou je univerzálnejšiepoužitie pre přípravu kopolymérov s roznymivinylovými monomérmi.Polymers containing β-cyclopentylacrylphenone structural units over unsubstituted (NSR Patent No. 2 119 855) and also oprotipmethoxyacrylophenone structural units (Czechoslovak Patent No. 170397) have the more quantum yields of tearing of the mains. In contrast to derivatives of the chalcone type, in which only copolymers with styrene (No. AO 185365) are protected, their advantage is the more universal use for the preparation of copolymers with nivinyl monomers.
Predmetom tohto vynálezu je sposob přípravyfotogradatívnych polymérov, ktoré sa získajúpolymerizáciou p-cyklopentyl akrylofenónu sa-motného, alebo polymerizáciou s vinylovými mo-nomérmi, výhodné so styrénom, metylakrylátom,akrylenitrilom, kyselinou akrylovou, kyselinoumetakrylovou, metylmetakrylátom, etylénom, vi- nylchloridom alebo vinylacetátom, pričom poly-merizačná zmes obsahuje 1 až 100 hmot. % p--cyklopentylakrylofenónu. Připravené polymérysa vyznačuji! tým, že vystavené vplyvy světladegradujú podstatné rýchlejšie ako bežne použí-vané polyméry. Podstata pósobenia karbonylo-vých štruktúr spočívá jednak vo zvýšenej ab-sorpci! světla a tiež v tom, že kvantové výtažkytrhania hlavných vazieb polymérov, ktoré súpredmetom vynálezu při 366 mm v benzénovomroztoku, sú najmenej o 3 poriadky vačšie akou komerčných polymérov, napr. polystyrénu apolymetylmetakrylátu.SUMMARY OF THE INVENTION The object of the present invention is to provide photogradative polymers obtained by polymerizing p-cyclopentyl acryrylphenone alone or by polymerization with vinyl monomers, preferably with styrene, methyl acrylate, acrylenitrile, acrylic acid, methacrylic acid, methyl methacrylate, ethylene, vinyl chloride or vinyl acetate. wherein the polymerization mixture comprises 1 to 100 wt. % p-cyclopentylacrylophenone. The prepared polymers are characterized by! in that the exposed influences diminish substantially faster than conventionally used polymers. The nature of the action of carbonyl structures lies in the increased sorption! and also that the quantum extraction of the main polymer bonds, which at least 366 mm in the benzene solution of the invention, are at least 3 orders of magnitude in the commercial polymers such as polystyrene and polymethyl methacrylate.
Vynález ilustrujú nasledujúce příklady:Příklad 1The following examples illustrate the invention: Example 1
Poly-p-cyklopentyl akrylofenón. 7,6 g p-cyklopentylakrylofenónu sa polymeri- zovalo so 4 mg AIBN za prebublávania čištěnýmdusíkom a tlaku 1,6 KPa 1 hod. Polymér sa čis-til 3násobným prezrážaním, v benzénu do metanolu. Výťažok 3,9 g (51 %). Polymér mal M„ =108 000 a Mn = 260 000 stanovené z GPC meranía kvantový výťažok trhania hlavných vazieb při366 nm v benzénovom roztoku bol 0,30 ± 0,05.Příklad 2Poly-p-cyclopentyl acrylophenone. 7.6 g of p-cyclopentylacrylophenone was polymerized with 4 mg of AIBN while bubbling with purified nitrogen and a pressure of 1.6 kPa for 1 hour. The polymer was purified by 3 times precipitation in benzene to methanol. Yield 3.9 g (51%). The polymer had M '= 108,000 and Mn = 260,000 determined from GPC measurement and the quantum yield of the main bond tearing at 366 nm in the benzene solution was 0.30 ± 0.05.
Kopolymér p-cyklopentylakrylofenónu so sty-rénom.Copolymer of p-cyclopentylacrylophenone with styrene.
3,07 g p-cyklopentylakrylofenónu a 13,6 g sty-rénu sa polymerizovalo bez iniciátora při 80 °C 2028293.07 g of p-cyclopentylacrylophenone and 13.6 g of styrene were polymerized without initiator at 80 ° C 202829
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS781978A CS202829B1 (en) | 1978-11-29 | 1978-11-29 | Process for preparing photodegradative polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS781978A CS202829B1 (en) | 1978-11-29 | 1978-11-29 | Process for preparing photodegradative polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202829B1 true CS202829B1 (en) | 1981-02-27 |
Family
ID=5428019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS781978A CS202829B1 (en) | 1978-11-29 | 1978-11-29 | Process for preparing photodegradative polymers |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS202829B1 (en) |
-
1978
- 1978-11-29 CS CS781978A patent/CS202829B1/en unknown
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