SU749833A1 - 1-beta-aminoethyl-2-polyaminoalkyl-(aralkyl)-amidazolines as epoxy resin solidifying agents - Google Patents
1-beta-aminoethyl-2-polyaminoalkyl-(aralkyl)-amidazolines as epoxy resin solidifying agents Download PDFInfo
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- SU749833A1 SU749833A1 SU772445872A SU2445872A SU749833A1 SU 749833 A1 SU749833 A1 SU 749833A1 SU 772445872 A SU772445872 A SU 772445872A SU 2445872 A SU2445872 A SU 2445872A SU 749833 A1 SU749833 A1 SU 749833A1
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- USSR - Soviet Union
- Prior art keywords
- aminoethyl
- polyaminoalkyl
- aralkyl
- amidazolines
- beta
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims description 5
- 229920000647 polyepoxide Polymers 0.000 title claims description 5
- 239000003795 chemical substances by application Substances 0.000 title 1
- -1 β-aminoethyl Chemical group 0.000 claims description 5
- 239000004848 polyfunctional curative Substances 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 240000000489 Agave utahensis Species 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical class NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 1
- 241000252505 Characidae Species 0.000 description 1
- 102100031007 Cytosolic non-specific dipeptidase Human genes 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
- 206010070834 Sensitisation Diseases 0.000 description 1
- 240000003864 Ulex europaeus Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RWYFURDDADFSHT-RBBHPAOJSA-N diane Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1=C(Cl)C2=CC(=O)[C@@H]3CC3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RWYFURDDADFSHT-RBBHPAOJSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1one
Изобретение относитс к новым химическим соединени м, конкретно кThis invention relates to new chemical compounds, specifically to
И (ин- снг- сн- снг-иг And (in- ing-ssng-ig
г« Т11 И,сНз,СгН5, CjHs; Яг -киРНгСИгннсНгснгЩгg “T11 I, cN3, CrH5, CjHs; Yag -kRNgSigsnnsNggsngShg
- ннснг cHgHHCBjciijimcHjcii н г- nnsng cHgHHCBjciijimcHjcii n g
-НН- CHjr ««|ИН1ШгСИ Н-№НгеН2ИН)„И-NN- CHjr «« | IN1ShGSI N-№NNeN2IN) „And
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используемым дл отверждени эпо.ксид-иH N-CHj-СН (МНСН2СН.2)з-NH, (тетрасых смол.этйленпентамин.).used for curing epo.xyd-and H N-CHj-CH (MHCH2CH2) c-NH, (ethylene pentamine tetras gum.).
Известно, что полиэтиденполиамины, Эти соединени позвол ют получатьIt is known that polyethylene polyamines, These compounds allow to obtain
в состав которых вход т диэтилен-эпоксиполимеры с максимальными дл which include diethylene epoxy polymers with a maximum for
трйамины, триэтилентетрамины ТЭТА),данной группы отвердителбй прсрчнссТтетраэтиленпентамины (ТЭПА)-, высшие 2Qными и теплофизическими показател ми. полиз1тиленполиамины, а также аминр- Недостатком этих соединений вл алкил-производные пиперазина, шйро-етс их сравнительно высока летуко используетс дл отверждени эпок-честь, дерматогенна активнботь сtriamines, triethylentetramines TETA), of this group are hardened by the type of tetraethylene pentamines (TEPA), the highest values of 2Q and thermal physical indicators. poly-1-thylene-polyamine, as well as aminr- The disadvantage of these compounds is alkyl-derivatives of piperazine, their relatively high Letuchroi is used for curing epox, dermatogen active with
сидных смол l . .сенсибилизацией и мала доступность.resin resin l. . sensitization and low availability.
. Наибольший интерес в качестве 25Диэтилентриамин дл отверждени . Of greatest interest as 25 Diethylenetriamine for curing
отвердител представл ет испЬдьзр за-,эпоксидных смол может бытй использоние триэтилентетрамина и тетраэти- вай лишь в редких случа х, посколькуhardeners are used for use, epoxy resins may be used with triethylentetramine and tetraethene only in rare cases, since
ленпентаминаон летучь, по сравнению с триэтиленH2N-CH2-CH2-NH-CHj-CH2-NH-CH2-CH2-NH2тётраМином И тетраэлёнпентамином, иLenpentaminon is volatile compared to triethylene, H2N-CH2-CH2-NH-CHj-CH2-NH-CH2-CH2-NH2, TiterMine And Tetraelenpentamine, and
.(триэтилёнтетрамин);JAдает эпоксиполимеры с более низкими. (triethylenetramine); JA gives epoxy polymers with lower
1- (р-а 1иноэтил)-2-полиаминоа кил (аралкил) имидазолинам общей формулы: X/1- (p-1inoethyl) -2-polyaminoalkyl (aralkyl) imidazolines of general formula: X /
прочностными тёплофизическимн свойствами .strength thermal properties.
Цель изобретени - улучшение свойств отвердител эпоксидных смол. Это достигаетс соединени ми формулы (1), которые получают алкилированием диэтилейтриамйна алкил (арил) акрилатом с последующим амиДолизом эфира и циклизацией амида.The purpose of the invention is to improve the properties of hardener epoxy resins. This is achieved by compounds of formula (1), which are obtained by alkylation of diethyl triamine alkyl (aryl) acrylate, followed by amylation of the ester and cyclization of the amide.
Пример 1. В круглодонную четырёхгорлую колбу снабжеййуй термометром , мешалкой, барботером дл подачи HHiepTHOro газа и ректификационной колонкой, соединенной с пр мым холодильником и сборником, загружают одндвремемно 100,1г(1 м) метилметакрилат и 206 г (2 м) диэтилентриамина . Смесь нагревают до и при температуре при перемешивании и непрерывной подаче азота выдерживают , в течение 3-х час. Затем температуру реакцион1йой массы постепенно поднимают до , одновременно отгон необходимое количесгвр метанола 32 г (1 м). После этого температуру реакционной массы медленно поднимают до 200-230°С одно- временной отгонкой реакцйойной воды. Яри реакционную смесь выдерживают до полного выделени воды. Получают 250 г 1-(2-аминоэтил)-2-(-9 метил-1 ,4,7-триазононил-9) имидазолина (98,5%.от теории), представл ющего собой темно-окрашенную ниэков зкую жидкость. . . Example 1. A round-bottom four-neck flask was equipped with a thermometer, a stirrer, a bubbler to supply HHiepTHOro gas and a distillation column connected to a direct cooler and a collector, one time, 100.1 g (1 m) of methyl methacrylate and 206 g (2 m) of diethylenetriam were charged. The mixture is heated to and at temperature with stirring and continuous supply of nitrogen is maintained for 3 hours. Then the temperature of the reaction mass is gradually raised to, at the same time the necessary quantity of methanol 32 g (1 m) is distilled. After that, the temperature of the reaction mass is slowly raised to 200-230 ° C by simultaneous distillation of the reaction water. Yari the reaction mixture is maintained until complete separation of water. 250 g of 1- (2-aminoethyl) -2 - (- 9 methyl-1, 4,7-triazononyl-9) imidazoline (98.5% of theory) are obtained, which is a dark-colored, non-viscous liquid. . .
Результаты испытаний приведена в табл. 1.The test results are given in table. one.
Пример 2. В услови х примера 1 иэ 200,2 г (2 м) метилметакрилата и 309 г (3 м) диэтилентриамина получают 402 г (98,5% от теории) среднев зкрго темно-окрашенного продукта , представл ющего собой технически чистый 1,11-бис 1-(lJ-аминоэтил) -имидазолил-2 -i,11-диметил-3,6,9 тетразаундекан.Example 2. Under the conditions of example 1, 200.2 g (2 m) of methyl methacrylate and 309 g (3 m) of diethylenetriamine give 402 g (98.5% of theory) of an average dark colored product, which is technically pure. 11-bis 1- (lJ-aminoethyl) -imidazolyl-2-i, 11-dimethyl-3,6,9 tetrazoundecane.
Пример 3. В колбу, снабженную Термометром, мешалкой и обратным холодильником загружают одновременно 30 г продукта, полученного пО примеру 1, 118 г продукта, полученногр пр Примеру 2, и 52 г диэтйлёнтриами Йа. месь нагревают до и при темдер атуре и перемешивании выдерживают в течение 1 час. Получают 200 г (99,5 от эагруж.) срёднёв зкого TeMHOr-pKpiameHHoird продукта. Н и мер -4. В услови х примеа i из 100 г (1 м) метилметакрилаТа 292 г (2 м) трйэтйлентетрамина пручают 338 г (98,5% от теории) сред- ; нёй экрго темнр-Ркр ашеннРгР продук-. : та, прёдс авл кю1его собой 1-( 12 меил- 1,4,7,10 тетразадодецил-12)-2 (1,4-диазагек Зил-б )-имидазолин.Example 3. In a flask equipped with a thermometer, a stirrer and a reflux condenser, 30 g of the product obtained in Example 1 was charged simultaneously, 118 g of the product obtained in Example 2, and 52 g of diethyl acetate Tri. Mons are heated before and at Temder ature and stirred for 1 hour. Receive 200 g (99.5 from the product load) of the medium TeMHOr-pKpiameHHoird product. And measures -4. Under the conditions of application, out of 100 g (1 m) of methyl methacrylateTa 292 g (2 m) of triethylentetramine, 338 g (98.5% of theory) of medium- are twisted; Ney Ekrgo Dark-Rcr AshennRgR Products-. : ta, predv avl kyu1a 1- (12 meyl-1,4,7,10 tetrazadodecyl-12) -2 (1,4-diazagek Zyl-b) -imidazoline.
Пример 5. В услови х примеа 1 из 100 г (1 м) метилметакрилата.Example 5. Under the conditions of application, 1 out of 100 g (1 m) of methyl methacrylate.
749833749833
103 г (1 м диэтилентриамина и 146 г (1м) трйэтйлентетрамина получают ,292 г (98% от теории) срёднёв зкого темно-окрашенного продукта, представл к дегр собой смесь изомерных имидазолинов .103 g (1 m of diethylenetriamine and 146 g (1 m) of triethylentetramine), 292 g (98% of theory) of a middle dark colored product are obtained, representing a mixture of isomeric imidazolines.
Пример 6. В услови х примера 1 из 72 г (1 м) акриловой кислоты и 206 г (2 м) диэтилентриамина полу-, чают 240 г (98,8% от теории) среднев зкого темно-окрашенного продукта,Example 6. Under the conditions of example 1, out of 72 g (1 m) of acrylic acid and 206 g (2 m) of diethylenetriamine, 240 g (98.8% of theory) of an average dark colored product are obtained,
представл ющего собой 1-(2-аминоэтил) -2-(1,4,7-триаэононил-9)-имидазолины.representing 1- (2-aminoethyl) -2- (1,4,7-triaenonyl-9) -imidazolines.
Пример 7. В услови х примера 1 из 148,16 г (1 м) фенилакриловой кислоты и 206 г (2 м) диэтилентриами5 на получают 340 г (98,5% от теории), в зкого темно-окрашенного продукта, представл ющего собой 1-(2-аминоэтил ) -2- (9-фенил-1, 4 ,7-триазанонил-9 )-имидазолин.Example 7. Under the conditions of example 1, out of 148.16 g (1 m) of phenylacrylic acid and 206 g (2 m) of diethylenetriam5, 340 g (98.5% of theory) of viscous dark colored product are obtained. 1- (2-aminoethyl) -2- (9-phenyl-1, 4, 7-triazanonyl-9) -imidazoline.
0- Характеристика полученных продуктов приведена в табл. 1.0- Characteristics of the products obtained are given in table. one.
Испытание полученного соединени как отвердител эпоксидных смол.Test of the obtained compound as an epoxy resin hardener.
5 Пример 8. Смесь 90 г эпоксидиановой смолы ЭД-22, 10 г бутилглицидноГо эфира и 22,5 г продукта, полученного в услови х примера 1, отверждают по следующему режиму: при5 Example 8. A mixture of 90 g of ED-22 epoxy diane resin, 10 g of butylglycic ether and 22.5 g of the product obtained under the conditions of example 1 is cured according to the following mode:
Q комнатной температуре - 24 час иQ room temperature - 24 hours and
При - 5 час. Свойства полученного эпоксиполимера приведены в табл. 2.At - 5 o'clock Properties of the obtained epoxy polymer are given in table. 2
П р и м е р 9. Смесь 90 г смолыPRI me R 9. A mixture of 90 g of resin
с ЭД-22, 10 г бутилглицидного эфира и 30,6 г продукта, полученного в услови х примера 2, отверждают пО ре- . жиму примера 8.with ED-22, 10 g of butylglycid ether and 30.6 g of the product obtained under the conditions of example 2 are cured with re-. press example 8.
П ри м е р 10. Смесь 90 г смолы , 10 г бутилглицидного эфира и 10 г продукта, полученного вFor example 10. A mixture of 90 g of resin, 10 g of butylglycid ether and 10 g of product obtained in
услови х примера 3, отверждают по режйму примера 8. Свойства эпоксиполимера приведены в табл. 2.the conditions of example 3 are cured according to the mode of example 8. The properties of the epoxy polymer are given in table. 2
Как видно из данных табл. 2, соединение по примеру 1 (аналог ТЭТА) дает эпрксиполимеры, которые незначительно уступают по прочностным показател м эпоксйполимарам на основе As can be seen from the data table. 2, the compound of Example 1 (TETA analogue) gives eprxypolymers that are slightly inferior in strength indicators to epoxy polymers based on
- чистого ТЭТА и несколькр превосходит- pure THETA and several times superior
их по деформациРнной теплостойкости. Наиболее.важным вл етс то, что синтезированные соединени позвол ют получать полиэтиленполиамины заданйого состава (смесь по примеру 3),their deformation of heat resistance. Most importantly, the synthesized compounds can produce polyethylene polyamines of a given composition (mixture according to Example 3),
5 которые дают более прочные полимеры, чем НЭПА (пр мого Синтеза из аммиака идихлорэтана). Кроме того, деформацирнна теплостойкость полимеров на Основе предлагаемых полиэтиленполи0 аминов за;цайного состава на 110135 0 превышает этот показатель полимеров на бснове Промышленных ПЭПА и их фракций (ДЭТА,ТЭТА и др.).5 which give stronger polymers than NEPA (direct Synthesis from ammonia and dichloroethane). In addition, the deformability of heat resistance of polymers on the basis of the proposed polyethylene polyamines for tamper composition by 110135 0 exceeds that of polymers based on Industrial PEPA and their fractions (DETA, TETA, etc.).
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СЬавнение свойств эпоксиполимеров на основе известных и предлагаеких полиаминов Comparison of properties of epoxy polymers based on known and proposed polyamines
Таб.лица 2Table 2
гg
Предел грочности/ кгс/смLimit of danger / kgf / cm
Claims (1)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU772445872A SU749833A1 (en) | 1977-01-18 | 1977-01-18 | 1-beta-aminoethyl-2-polyaminoalkyl-(aralkyl)-amidazolines as epoxy resin solidifying agents |
| GB1169/78A GB1566841A (en) | 1977-01-18 | 1978-01-12 | 1-( -aminoethyl) - 2 - polyamino-alkyl(aralkyl)-imidazolines and method of preparing same |
| IT7841506A IT7841506A0 (en) | 1977-01-18 | 1978-01-17 | 1-(B-AMINOETHYL)-2-POLYAMINOALKYL(OR ARALKYL)-IMIDAZOLINES AND PROCEDURE TO OBTAIN THEM. |
| DE19782802072 DE2802072A1 (en) | 1977-01-18 | 1978-01-18 | 1- SQUARE BRACKETS ON BETA-AMINOAETHYL (-2-POLYAMINOALKYL) ARALKYL SQUARE BRACKETS FOR-IMIDAZOLINE AND METHOD FOR PRODUCING IT |
| JP342578A JPS53130663A (en) | 1977-01-18 | 1978-01-18 | 11*betaaaminoethyl**22 polyaminoalkyl*imidazolines and process for preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU772445872A SU749833A1 (en) | 1977-01-18 | 1977-01-18 | 1-beta-aminoethyl-2-polyaminoalkyl-(aralkyl)-amidazolines as epoxy resin solidifying agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU749833A1 true SU749833A1 (en) | 1980-07-23 |
Family
ID=20692968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772445872A SU749833A1 (en) | 1977-01-18 | 1977-01-18 | 1-beta-aminoethyl-2-polyaminoalkyl-(aralkyl)-amidazolines as epoxy resin solidifying agents |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS53130663A (en) |
| DE (1) | DE2802072A1 (en) |
| GB (1) | GB1566841A (en) |
| IT (1) | IT7841506A0 (en) |
| SU (1) | SU749833A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7005087B2 (en) * | 2003-12-30 | 2006-02-28 | Nalco Energy Services, L.P. | Composition and method for preventing fouling in (meth)acrylic acid processes |
-
1977
- 1977-01-18 SU SU772445872A patent/SU749833A1/en active
-
1978
- 1978-01-12 GB GB1169/78A patent/GB1566841A/en not_active Expired
- 1978-01-17 IT IT7841506A patent/IT7841506A0/en unknown
- 1978-01-18 JP JP342578A patent/JPS53130663A/en active Pending
- 1978-01-18 DE DE19782802072 patent/DE2802072A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2802072A1 (en) | 1978-07-20 |
| IT7841506A0 (en) | 1978-01-17 |
| JPS53130663A (en) | 1978-11-14 |
| GB1566841A (en) | 1980-05-08 |
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