SU436830A1 - The method of producing copolymers - Google Patents
The method of producing copolymersInfo
- Publication number
- SU436830A1 SU436830A1 SU1774813A SU1774813A SU436830A1 SU 436830 A1 SU436830 A1 SU 436830A1 SU 1774813 A SU1774813 A SU 1774813A SU 1774813 A SU1774813 A SU 1774813A SU 436830 A1 SU436830 A1 SU 436830A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- styrene
- vinyl
- copolymer
- diallyl
- aroma
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 37
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 14
- 229920001567 vinyl ester resin Polymers 0.000 claims description 10
- -1 hydroxy ester Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 5
- ZDOIAPGLORMKTR-UHFFFAOYSA-N 2-Hydroxyfluorene Chemical compound C1=CC=C2C3=CC=C(O)C=C3CC2=C1 ZDOIAPGLORMKTR-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZKHNBCNZDYATQG-UHFFFAOYSA-N 1-amino-5-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2N ZKHNBCNZDYATQG-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
1one
Изобретение относитс к (получению сополимеров стирола с Производными конденсиро1ваиных ароматических углеводородов.The invention relates to the preparation of copolymers of styrene with derivatives of condensable aromatic hydrocarbons.
Известен способ получени сополимеров путем суспензионной сополимеризации стирола или смеси стирола с дивинилбензолом с винилпиридином .A known method for producing copolymers by suspension copolymerization of styrene or a mixture of styrene with divinylbenzene with vinylpyridine.
Предлагаемый способ отличаетс от известного тем, что в качестве ненасыщенного соединени , сополимеризующегос со стиролом или смесью стирола с дивинилбензолом, примен ют виниловый или диаллиловый эфир оксипроизводного конденсированного ароматического углеводорода.The proposed method differs from that in that the vinyl or diallyl ether of the hydroxy derivative of the condensed aromatic hydrocarbon is used as the unsaturated compound copolymerizable with styrene or a mixture of styrene with divinylbenzene.
При этОМ в качестве виниловых эфиров примен ют виниловые эфиры З-оксиаценафтена , 2-оксифлуорена, Ьокси-Б-амино-аитрахинона , в качестве диаллиловых эфиров - диаллилоБые эфиры а-амино-9,10-ант1рагидрохинона и 1,4-диамино-9,10-аитрагидрохинона.In this case, vinyl ethers of 3-hydroxyacene-naphthene, 2-hydroxyfluorene, hydroxy-B-amino-aitraquinone are used as vinyl esters, diallyl esters of a-amino-9,10-anthilohydroquinone and 1,4-diamino-9 as diallyl ethers , 10-aitrahydroquinone.
Предлагаемый способ позвол ет получать полимерные материалы, обладающие повышениой теплостойкостью. Использование в качестве сомономеров виниловых и диаллиловых эфиров аминоантрагидрохинонов позвол ет получать светостойкие структурноокрашенные полимеры.The proposed method allows to obtain polymeric materials with enhanced heat resistance. Using vinyl and diallyl ethers of aminoanthrahydroquinones as comonomers makes it possible to obtain light-resistant structurally colored polymers.
Сополимеризацию стирола с указанными виниловыми и диаллиловыми эфирами осуществл ют в водной суспензии в присутствииThe copolymerization of styrene with the indicated vinyl and diallyl ethers is carried out in an aqueous suspension in the presence of
в качестве стабилизатора трикальцийфосфата и инипиаторОБ - перекиси бензоила (ПБ) и третбутплпербензоата (ТБПБ).as a stabilizer of tricalcium phosphate and initiator OB - benzoyl peroxide (PB) and tert-butyl perbenzoate (TBPB).
Температура сополимеризации в присутстБии ПБ составл ет 80-90°, в присутствии ТБПБ -95-100°.The temperature of copolymerization in the presence of PB is 80-90 °, in the presence of TBPB -95-100 °.
Количество виниловых эфиров в исходной смеси мономе;ров равно IQ-12%. При получении сшитых сополимеров соотношение мономеров следующее: стирола 90%, дивинилбензола 8-10% и виниловых и диаллиловых эфиров антрагидрохиноиа 1-2%.The amount of vinyl ethers in the initial monome mixture; the ditch is IQ-12%. In the preparation of crosslinked copolymers, the ratio of monomers is as follows: styrene 90%, divinylbenzene 8-10% and vinyl and diallyl ethers of anthrahydroquinone 1-2%.
Применение диаллиловых эфиров аминоаптрагидрохинона дает возмолсность получить интенсивно окрашенные сополимеры, устойчиБые к действию высоких температур, органических растворителей, кислот и щелочей .The use of diallyl ethers of aminoaptrahydroquinone makes it possible to obtain intensely colored copolymers that are resistant to high temperatures, organic solvents, acids and alkalis.
Пример 1. В трехгорлую колбу емкостью 1 л загружают предварительно приготовленный водный раствор трикальпийфосфата (избыток Саз(РО4)2 составл ет 0,35%) s количестве 350 мл. К раствору стабилизатора приExample 1. A three-neck flask with a capacity of 1 l is loaded with a previously prepared aqueous solution of tricalpium phosphate (an excess of Chaz (PO4) 2 is 0.35%) of 350 ml. To stabilizer solution at
работающей мешалке добавл ют масл ную фазу в количестве 360 мл следующего состава: стирол - 90%, дивинплбеизол - 8%, диаллиловый эфир 1,4-диаминоантрахинана - 2%, перекись бензола - 0,7%, третбутилпербензоат - 0,7% от веса смеси.the oil mixer in the amount of 360 ml of the following composition is added to the working mixer: styrene - 90%, divinplbeizol - 8%, diallyl ester of 1,4-diaminoanthraquinane - 2%, benzene peroxide - 0.7%, tert-butyl perbenzoate - 0.7% of weight of the mixture.
В течение одного часа реакционную массу нагревают до 80°С и при этой температуре содержимое колбы выдерживают в течение 2 час. Затем температуру повышают до 95- 98°С и выдерживают при этой температуре 4 час.Within one hour, the reaction mass is heated to 80 ° C and at this temperature, the contents of the flask is maintained for 2 hours. Then the temperature is raised to 95-98 ° C and kept at this temperature for 4 hours.
Через каждый 1 -1,5 часа проводитс проверка сополимера на твердость гранзл. По достижении необходимой степени сополимеризации содержимое колбы охлаждают до комнатной температуры, разрушают стабилизатор разбавленной сол ной кислотой, отмывают сополимер до нейтральной среды (по универсальной индикаторной бумаге) и сушат conoj лимер на воздухе. Получают нерастворимый и неплавкий сополимер цвета бордо с высокой термической устойчивостью: изменение цвета наблюдаетс при 350°С; разложение образца начинаетс при 370°С.Every 1-1.5 hours, the copolymer is checked for hardness of the granule. Upon reaching the required degree of copolymerization, the contents of the flask are cooled to room temperature, the stabilizer is destroyed with dilute hydrochloric acid, the copolymer is washed to neutral medium (using universal indicator paper), and the mixture is dried in air. An insoluble and non-meltable bordeaux color copolymer with high thermal stability is obtained: a color change is observed at 350 ° C; sample decomposition begins at 370 ° C.
Пример 2. Сшитый сополимер из стирола , дивинилбензола и диаллилового эфира аамино-9 ,10-антрагидрохинона получают по методике , описанной в примере 1, при следующих соотношени х компонентов: стирол - 90%, дивинилбензол -8%, диаллиловый эфир а-аМИ1НО-9,10-а1нтрагидрохинона - 2%, ПБ - 0,7%, ТБПБ -0,7% от веса смеси.Example 2. A crosslinked copolymer of styrene, divinylbenzene and amino-9, 10-anthrahydroquinone diallyl ether is prepared according to the procedure described in Example 1, with the following ratios of components: styrene — 90%, divinylbenzene —8%, diallyl ether a-AMI1OHO 9,10-a1ntrahydroquinone - 2%, PB - 0.7%, TBPB -0.7% by weight of the mixture.
Получают сшитый сополимер оранжевого цвета с цветоустойчивостью до 260°С, разложение начинаетс ри температуре выше 320°С.A crosslinked copolymer of orange color with color stability up to 260 ° C is obtained, decomposition begins at a temperature above 320 ° C.
Пример 3. Сшитый сополимер стирола, дивинилбензола и винилового эфира 1-окси-5амвноантрахинона получают по методике, описанной в примере 1, -при загрузке веш;еств: стирол-90%, дивинил-бензол-8%, виниловый эфир 1-окси-5-аминоантрахинона - 2%, ПБ - 0,7%, ТБПБ -0,7%.Example 3. A crosslinked copolymer of styrene, divinylbenzene and vinyl ester of 1-hydroxy-5-benzo anthraquinone is obtained according to the procedure described in example 1, when loading vesh; properties: styrene-90%, divinyl-benzene-8%, vinyl ester of 1-hydroxy- 5-aminoanthraquinone - 2%, PB - 0.7%, TBPB -0.7%.
Получают структурносшитый сополимер красного цвета, устойчивый до 260°С, разложение сополимера начинаетс выше 320°С.A red-colored structural copolymer stable up to 260 ° C is obtained, decomposition of the copolymer begins above 320 ° C.
Пример 4. Сополимер стирола и винилового эфира 3-оксиаценафтена получают по методике, описанной в примере 1, при следующих соотношени х компонентов: стирол -Example 4. A copolymer of styrene and vinyl ester of 3-hydroxyacenefathene was prepared according to the procedure described in Example 1, with the following ratios of the components: styrene -
90%, виниловый эфир 3-оксиаценафтена - 10%, ПБ -0,7%, ТБПБ -0,7%.90%, vinyl ester of 3-hydroxyacetylene - 10%, PB -0.7%, TBPB -0.7%.
Получают сополимер линейной структуры, растворимый в большинстве органических растворителей. Мол. в. 4000-8000. Температура начала разложени 275°С.A linear structure copolymer soluble in most organic solvents is obtained. Mol at. 4000-8000. The decomposition start temperature is 275 ° C.
Пример 5. Сополимер стирола и винилового эфира 2-окси-:флуорена получают по методике , описанной в примере 1, при следующих количествах исходных веществ: стирол - 90%, виниловый эфир 2-оксифлуорена - 10%, ПБ -0,7%, ТБПБ -0,7%.Example 5. A copolymer of styrene and vinyl ester of 2-hydroxy-: fluorene is obtained according to the method described in example 1, with the following amounts of starting materials: styrene - 90%, vinyl ester of 2-hydroxyfluorene - 10%, PB -0.7%, TBPB -0.7%.
Получают сополимер по свойствам, аналогичный сополимеру, полученному в примере 4.Get the copolymer on the properties similar to the copolymer obtained in example 4.
Пример 6. Сополимер стирола и винилового эфира 9-окси-антрахиНОна получают по методике, описанной в примере 1, при следующих количествах исходных компонентов: стирол - 90%, виниловый эфир 1-оксиантрахино на-10% , ПБ -0,7%, ТБПБ -0,7%.Example 6. A copolymer of styrene and vinyl ester of 9-hydroxy-anthrahonone is obtained according to the procedure described in Example 1 with the following amounts of the starting components: styrene — 90%, 1-hydroxyanthrachino vinyl ester at -10%, PB -0.7%, TBPB -0.7%.
СополИлМер аналогичен по свойствам сополимерам , полученным в примерах 4 и 5. Температура начала разложени сополимера 28ГС.Copolymer is similar in properties to the copolymers obtained in Examples 4 and 5. The temperature at which decomposition of the copolymer starts to 28 ° C.
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Предмет изобретени Subject invention
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1774813A SU436830A1 (en) | 1972-04-18 | 1972-04-18 | The method of producing copolymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1774813A SU436830A1 (en) | 1972-04-18 | 1972-04-18 | The method of producing copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU436830A1 true SU436830A1 (en) | 1974-07-25 |
Family
ID=20511260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1774813A SU436830A1 (en) | 1972-04-18 | 1972-04-18 | The method of producing copolymers |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU436830A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5073269A (en) * | 1987-01-10 | 1991-12-17 | Basf Corporation | Preparation of water-soluble copolymers of maleic acid and use thereof as water treatment agents |
-
1972
- 1972-04-18 SU SU1774813A patent/SU436830A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5073269A (en) * | 1987-01-10 | 1991-12-17 | Basf Corporation | Preparation of water-soluble copolymers of maleic acid and use thereof as water treatment agents |
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