CS210307B1 - Method of preparation of adicts and/or polyadicts on the base of epoxide bitumens,amines and additive salts therof - Google Patents
Method of preparation of adicts and/or polyadicts on the base of epoxide bitumens,amines and additive salts therof Download PDFInfo
- Publication number
- CS210307B1 CS210307B1 CS340580A CS340580A CS210307B1 CS 210307 B1 CS210307 B1 CS 210307B1 CS 340580 A CS340580 A CS 340580A CS 340580 A CS340580 A CS 340580A CS 210307 B1 CS210307 B1 CS 210307B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- weight
- amines
- preparation
- reaction
- diluent
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 6
- 239000000654 additive Chemical class 0.000 title 1
- 230000000996 additive effect Effects 0.000 title 1
- 150000002118 epoxides Chemical class 0.000 title 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 239000003822 epoxy resin Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 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 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- -1 epoxidized soybean Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000002557 mineral fiber Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 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
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
(54) Sposob přípravy aduktov a/alebo polyaduktov na báze epoxidových živíc, amínov a ich adičných solí(54) Process for preparing adducts and / or polyadducts based on epoxy resins, amines and their addition salts
Vynález sa; týká spósobu přípravy aduktov a/alebo polyaduktov na báze epoxidových živic, aiBÍnov a ich adičných solí reakciou epoxidových živíc so zlúčeninami s primárnými a/alebo sekundárnými aminoskupinami s. neutra 1 izáciou s kyselinami.The invention; relates to a process for the preparation of adducts and / or polyadducts based on epoxy resins, albins and their addition salts by reacting epoxy resins with compounds having primary and / or secondary amino groups with a. neutralization with acids.
K úpravě skleněných a minerálnych vlákien našli široké uplatnenie rožne adukty a pólyadukty na báze epoxidových živíc, amínov a ich adičné soli s kyselinami.For the treatment of glass and mineral fibers, various adducts and polyadducts based on epoxy resins, amines and their acid addition salts have found wide application.
Pri syntézách sa používajú rožne epoxidové živíce napr. g i y c id y 1 é t er y , připravované reakciou epichlórhydrínu, me t y 1 ep í chl ór hy dr ínu cí dichlorhydrínu s fenolmi, bisfenolmi, t.ris·fenolmi, t e tr ak is f eno lm:L, alifatickými či cykloalif atickými alkoholrni alebo glykolmi. Zo skupiny glycidylesterov sú to hlavně diglycidylestery dikarboxylových aromatických a hydroaromatických kyselin. !·'.poxidov ané estery kyselin napr. epoxídovaný sojovýlanový, dehydratovaný ricínový olej a pod.Various epoxy resins, e.g. Glycidyl ethers prepared by the reaction of epichlorohydrin, methephylorohydrinic dichlorohydrin with phenols, bisphenols, trisphenols, tri- phenylene, aliphatic or cycloaliphatic alcohol or glycols. From the group of glycidyl esters, these are mainly diglycidyl esters of dicarboxylic aromatic and hydroaromatic acids. Polyester esters of acids e.g. epoxidized soybean, dehydrated castor oil and the like.
Adicia a/alebo polyadícía sa uskutočňuje za použitia rčznych alifatických, cykloalifatíckých, aromatických, heterocyklických amínov, polyamínov, polyarainoamidov, ich zmesi a pod. /aut. osv,. č. 1 87 838 ČS, britský pat. č. 1 234 23 5 /.The addition and / or polyaddition is carried out using various aliphatic, cycloaliphatic, aromatic, heterocyclic amines, polyamines, polyarainoamides, mixtures thereof and the like. / Cars. lighting ,. no. 1 87 838 MS, British Pat. no. 1,234 23 5 /.
Reakcia s ainínnii sa uskutočňuje hu<3 v tavenine, zvyeajne v nadbytku aminu, alebo v prostředí riedidiel /Lidařík M. a kol.: Epoxydové pryskyřice, SNTI. Praha 1961 s. 208/. Z dovodu, že v tavenine. je obtiažne připravit adukty s volnými epoxidovými skupinami, pretože dochádza k tvorbě gelov a v niektorých prípadoch sú aj reakcie fažko ovládatelné pre ich exotermícký prícbeh, pracuje sa v prostředí roznych riedidiel.The reaction with aininium is carried out hu < 3 in the melt, usually in excess of the amine, or in the diluent environment / Lidařík M. et al .: Epoxy resins, SNTI. Prague 1961 p. 208 /. Because of that, in the melt. It is difficult to prepare adducts with free epoxy groups because of the formation of gels and in some cases reactions are difficult to control because of their exothermic story, working in a variety of diluents.
V případe aplikácie reakčných produktov do lubrikačných kompozřcií na úpravu skleněných a minerálnych vlákien sa reakcia uskutočňuje v róznych prchavých riedidlách. Zvyčajne sa používajú rožne nižšie alkoholy, ketony, dioxan, dimethylformamid a pod.In the case of application of the reaction products to the glass and mineral fiber lubricating compositions, the reaction is carried out in various volatile diluents. Typically, various lower alcohols, ketones, dioxane, dimethylformamide and the like are used.
Reakčné produkty je možné v závislosti od ich aplikačného použitia neutralizovat buď rainerálnými alebo organickými kyselinami hned po ukončení reakcie alebo tesne před ich aplikačným použitím.Depending on their application, the reaction products can be neutralized either with raineral or organic acids immediately after the reaction is completed or just prior to their application.
Po aplikácii lubrikačných kompozici! s obsahom roztokov aduktov a/alebo polyaduktov k úpravě vlákien rozpústadlá použité pri ich syntéze pri sušení vlákien prchajú, t. j. dochádza k ich znehodnoteníu. Týmto sposobom dochádza zároveň k znečišťovaniu ovzdušia a zvyšuje sa nebezpeČenstvo požiaru v suŠiarnach vlákien.After applying the lubricating compositions! containing solutions of fiber adducts and / or polyadducts, the solvents used in their synthesis during the drying of the fibers are volatile, i. j. they are depreciated. This also causes air pollution and increases the risk of fire in the fiber dryer.
Uvedené nevýhody sa odstránia pri použití spósobu přípravy podlá vynálezu.These disadvantages are overcome by the preparation method of the invention.
Vynález popisuje spósob přípravy aduktov a/alebo polyaduktov na báze epoxidových živíc, aminov a ich adičných solí, reakciou so zlúčeninami s primárnými a/alebo sekundárnými arainoekupinami a neutralizáciou s kyselinami v prostředí riedidla na báze zlúčenín alkylénoxidov s 2 a/alebo 3 atómami uhlíka s vodou a/alebo organickou kyslíkatou látkou s 3 až 20 atómami' uhlíka s najmenej jedným aktívnym vodíkom, ktorých priemerná molekulová hmotnost je 250 až 6 000, s výhodou 300 až 1 500jalebo v prostředí glycerolu.The present invention relates to a process for the preparation of adducts and / or polyadducts based on epoxy resins, amines and their addition salts, by reaction with compounds with primary and / or secondary araino groups and neutralization with acids in a diluent based on alkylene oxide compounds having 2 and / or 3 carbon atoms. water and / or an organic oxygen substance having from 3 to 20 carbon atoms with at least one active hydrogen having an average molecular weight of 250 to 6,000, preferably 300 to 1,500, or in a glycerol environment.
Reakčná násada móže obsahovat 10 až' 90 Z, s výhodou 40 až 60 Z hmot. riedidiel, ktoré móžu obsahovat stopy až 50 Z, 9 výhodou 5 až 25 Z hmot. vody.The reaction batch may contain from 10 to 90% by weight, preferably from 40 to 60% by weight. diluents which may contain traces of up to 50% by weight, preferably 5 to 25% by weight. water.
Podlá druhu riedidla, toto v lubrikačných kompozíciach zastáva buď funkciu mazadla, zmáčadla, antistatika, zvláčňovadla či zraakčovadlá. Týmto spósobom sa zároveň ulahčí práca pri príprave lubrikačných kompozici!.Depending on the type of diluent, this in lubricant compositions functions either as a lubricant, wetting agent, antistatic agent, emollient or scraper. This also facilitates the preparation of lubricant compositions.
Z dóvodu, že reakčné produkty připravované v prostředí riedidiel podlá vynálezu sú silné viskózne, pastovité až tuhé hmoty, je výhodné ich po ukončení syntézy riedit, s výhodou vodou, připadne ich kombinovat s dalšími zložkami lubrikačných kompozici! na viskozitu, ktorá umožňuje ich automatické davkovanie a váženie.Since the reaction products prepared in the diluent environment according to the invention are strong viscous, pasty to solid masses, it is advantageous to dilute them, preferably with water, or to combine them with the other components of the lubricating compositions after the synthesis is complete! viscosity, which allows them to be metered and weighed automatically.
Predovšetkým z ekonomických příčin a lahkej dostupnosti je najvýhodnejšie použitie polyetylénglykolu s priemernou molekulovou hmotnosčou 300.Particularly for economic reasons and easy availability, the use of polyethylene glycol with an average molecular weight of 300 is most preferred.
Vynález je ďalej objasněný formou príkladov, v ktorých zloženie je uvádzané v hmotnostných Z.The invention is further elucidated by way of examples in which the composition is given in weight Z.
Příklad 1Example 1
Syntéza sa uskutočňovala v prostředí oxyetylovaných zlúčenín vzorcovíThe synthesis was carried out in an environment of oxyethylated compounds of the formula
A - oxyetylovaný nonylfenol vzorcaA - oxyethylated nonylphenol of formula
B - blokový kopolymér etylénoxidu a propylénoxidu vzorcaB - block copolymer of ethylene oxide and propylene oxide of formula
kde a + c 13,6; b * 15,5 C - polyetylénglykol vzorcawhere a + c 13.6; b * 15.5 C - polyethylene glycol of formula
2103 O 7 hoch2ch2/och2ch2/ och2ch2oh2103 O 7 hoch 2 ch 2 / och 2 ch 2 / och 2 ch 2 oh
Do banky sa předložil© 200 g epoxidovej živice na báze dianu a epichlorhydrinu o obsahu 0,51 epoxiekv. /100 g, 110 g dietáno 1 aminu a 300 g riedidla. Násada sa za miešania vyhriala na teplotu 40 až 50 °C, potom sa reakčným teplom vyhriala na 100 až 130 °C. Reakcia sa nechala prebiehať pri 100 °C 1,5 hodiny. Po ochladení násady na 60 až 70 °C sa přidalo 32 g kyseliny octovej a žívica sa riedila vodou na 50 Vlastnosti reakčných produktov sú uvedené v tabulke .Banky 200 g of epian resin based on dian and epichlorohydrin containing 0.51 epoxies were introduced into the flask. 100 g, 110 g diethan 1 amine and 300 g diluent. The batch was heated to 40-50 ° C with stirring, then heated to 100-130 ° C by reaction heat. The reaction was allowed to proceed at 100 ° C for 1.5 hours. After cooling the batch to 60-70 ° C, 32 g of acetic acid was added and the resin was diluted with water to 50. The properties of the reaction products are shown in the table.
C 1 ,5C 1, 5
Příklad 3Example 3
Syntéza sa uskutočnovala v prostředí polyetylénglykolu vzorca:The synthesis was carried out in the environment of polyethylene glycol of the formula:
roch2ch2/och2ch2/ och2ch2ohroch 2 ch 2 / och 2 ch 2 / och 2 ch 2 oh
474474
Do banky sa předložilo 50 g 3 , 4-epoxicyklohexylmetýl“3,4-e.poxicyklohexankarboxylátu 85 g po 1 y e t y 1 e.ng 1 yko lu , 30 g vody a 38 g piperidínu. Reakčná zmes sa za miešania udržovala • pri teplote 60 °Č 2 hodiny. Přidáním 27 g kyseliny octovej sa násada zneutra 1izovala a zmiesala s 120 g vody. Reakčný produkt má viskozitu 26 mPa.s/20 °C a farbu 60 mg J .50 g of 3,4-epoxy-cyclohexylmethyl-3,4-epoxy-cyclohexanecarboxylate, 85 g of polyglycol, 30 g of water and 38 g of piperidine were introduced into a flask. The reaction mixture was kept under stirring at 60 ° C for 2 hours. The batch was neutralized by addition of 27 g acetic acid and mixed with 120 g water. The reaction product has a viscosity of 26 mPa · s / 20 ° C and a color of 60 mg J.
Příklad 4’Example 4 ’
Pri syntéze sa použil ρo 1yety1éng1yko1 ako v příklade 3. Do banky sa předložilo 65,1 g epoxidovej živice na báze dianu aminu, 31,6 g benzidínu a 125 g 2 hodiny. Po ochladení na 60 až a epichlorhydrinu o obsahu 0,51 epoxiekv./ 100 g, 18 g díetanol0 po ly e t y 1 englyko lu . Nasada aa zahnevala pn teplote 100 C oSynthesis was carried out as described in Example 3. A flask was charged with 65.1 g of an amine diane epoxy resin, 31.6 g of benzidine and 125 g of 2 hours. After cooling to 60 to a. Epichlorohydrin of 0.51 epoxy / 100 g, 18 g of ethanol / polyethylene glycol. The seed was heated at 100 ° C
C sa přidalo 20,6 g kyseliny octovej a 250 g vody. Reakčný produkt má viskozitu 7 95 mřa.s/2'0 C a farbu 40 mg JC was added 20.6 g acetic acid and 250 g water. The reaction product has a viscosity of 7 95 mPa · 2 ° C and a color of 40 mg J
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS340580A CS210307B1 (en) | 1980-05-16 | 1980-05-16 | Method of preparation of adicts and/or polyadicts on the base of epoxide bitumens,amines and additive salts therof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS340580A CS210307B1 (en) | 1980-05-16 | 1980-05-16 | Method of preparation of adicts and/or polyadicts on the base of epoxide bitumens,amines and additive salts therof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS210307B1 true CS210307B1 (en) | 1982-01-29 |
Family
ID=5374002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS340580A CS210307B1 (en) | 1980-05-16 | 1980-05-16 | Method of preparation of adicts and/or polyadicts on the base of epoxide bitumens,amines and additive salts therof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS210307B1 (en) |
-
1980
- 1980-05-16 CS CS340580A patent/CS210307B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3356645A (en) | Process for curing epoxy resins with a salt of an imidazole and compositions thereof | |
| US3793278A (en) | Method of preparing sulfonium group containing compositions | |
| US2872428A (en) | Polyepoxide emulsions and method of treating textiles therewith | |
| KR900007873B1 (en) | Durable coating composition and epoxy resin adduct useful therein | |
| DE69615857T2 (en) | LATENT HARDENER COMPOSITIONS AND METHOD FOR THEIR PRODUCTION | |
| CA1113643A (en) | Method of water-solubilizing high performance polyether epoxide resins, the solubilized resins and thermoset, hydrophobic coatings derived therefrom | |
| US3896082A (en) | Epoxy powder coatings and method therefor | |
| KR870007877A (en) | Method of preparing aminourethane | |
| GB1057292A (en) | Water soluble epoxides and coating compositions containing such compounds | |
| DE1545049B2 (en) | Process for the production of polyadducts | |
| EP0000605A1 (en) | Hardeners for aqueous dispersions of epoxy resins, their preparation and use | |
| US3129133A (en) | Colloidal dispersions of partially cured polyepoxides, their preparation and use for preparing wet strength paper | |
| US4554342A (en) | Heat-curable compositions comprising an epoxy resin, an amine and a sulfonium salt | |
| US3391097A (en) | Epoxy resins from 1, 1'-methylene bis | |
| EP1436339B1 (en) | Low viscosity curing agents compositions in epoxy resin systems for low temperature cure applications | |
| US3945972A (en) | Curable epoxy resin composition comprising an epoxy resin and a reactive diluent | |
| GB804294A (en) | Improvements in or relating to the preparation of curing agents for polyepoxides | |
| US3417140A (en) | Amido-amine compositions | |
| EP1040150B1 (en) | Novolaks as water-unaffected accelerators for epoxy resin hardeners | |
| US4178426A (en) | Epoxy resin compositions | |
| CA1278136C (en) | Process for producing self-crosslinking ced-binders | |
| EP0305802A2 (en) | Epoxy resin adhesive composition | |
| DE1595484C3 (en) | Process for the production of castor oil polyglycidyl ether and its use for the production of a hardenable composition | |
| DE69132698T2 (en) | Water emulsifiable epoxy resin composition | |
| US3418333A (en) | Salts of imidazoles and benzimidozoles |