CS247344B1 - Thermoplastic adduct - Google Patents
Thermoplastic adduct Download PDFInfo
- Publication number
- CS247344B1 CS247344B1 CS324285A CS324285A CS247344B1 CS 247344 B1 CS247344 B1 CS 247344B1 CS 324285 A CS324285 A CS 324285A CS 324285 A CS324285 A CS 324285A CS 247344 B1 CS247344 B1 CS 247344B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- adduct
- triethanolamine
- thermoplastic
- epoxy resin
- water
- Prior art date
Links
- 229920001169 thermoplastic Polymers 0.000 title claims description 4
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 12
- 239000003822 epoxy resin Substances 0.000 claims description 11
- 229920000647 polyepoxide Polymers 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 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 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 229960004418 trolamine Drugs 0.000 description 10
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003365 glass fiber Substances 0.000 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 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
Vynález sa týká termoplastického aduktu epoxidové] živice a trietanol aminu o teplote maknutia 25 až 85 °C a amínovom čísle 80 až 200 mg KOH/g, vhodného vo formě soli s vo vodě rozpustnými kyselinami na povrchová úpravu skleněných vlákien.The present invention relates to a thermoplastic adduct of epoxy resin and triethanol amine having a melt temperature of 25-85 ° C and an amine number of 80-200 mg KOH / g, suitable in the form of a salt with water-soluble acids for surface treatment of glass fibers.
Adukty na báze epoxidových živíc sú známe a majú široké priemyselné uplatnenie, hlavně v oblasti nátěrových hmot. Pri syntézách sa využívá predovšetkým reaktivita epoxidovej skupiny so zlúčeninami obsahujúcimi hydroxylové, karboxylové a aminové skupiny. Najviac sa pri výrobě používajú rožne difenolické zlúčeniny a diepoxidy (čs. pat. č 122 687, 135 615), připadne rožne glykoly, či ich kombinácie s difenolmi (čs. pat. č. 132 676).Additives based on epoxy resins are known and have a wide industrial application, especially in the field of paints. In the syntheses, the reactivity of the epoxide group with compounds containing hydroxyl, carboxyl and amine groups is mainly used. Various diphenol compounds and diepoxides (U.S. Pat. Nos. 122,687, 135,615), or various glycols, or combinations thereof with diphenols (U.S. Pat. No. 132,676) are the most widely used.
K povrchovej úpravě skleněných vlákien našli významné uplatnenie adukty na báze epoxidových živíc a primárných alebo sekundárných alkanolamínov (čs. aut. osv. č. 224 025), predovšetkým dietanolamínu s epoxidovými živicami na báze dianu. Zlepšenie aplikačných vlastností týchto aduktov sa dosiahlo přípravou zmesných aduktov reakciou epoxidovej živice s dietanolamínom a alifatickými polyamínmi (čs. aut. osv. č. 211 723). Z důvodu, že pri sušení upravených skleněných vlákien, spravidla nad 100 °C dochádza k nežiaducému sfarbeniu vlákien, používajú sa tieto adukty buď v menších koncentráciach, alebo pri technológiach, kde sa nevyžaduje sušenie vlákien.The adducts based on epoxy resins and primary or secondary alkanolamines have been found to be of great importance for the surface treatment of glass fibers (es. Aut. En. Improvements in the application properties of these adducts were achieved by preparing mixed adducts by reacting the epoxy resin with diethanolamine and aliphatic polyamines (cf. no. 211 723). Because of the undesirable coloration of the fibers when drying the treated glass fibers, typically above 100 ° C, these adducts are used either in smaller concentrations or in technologies where fiber drying is not required.
Pri aplikačnom výskume sme zistili, že uvedené nevýhody sa odstránia pri použití aduktov podfa vynálezu k povrchovej úpravě skleněných vlákien.In the application research we have found that these disadvantages are overcome by the use of the adducts of the invention for the surface treatment of glass fibers.
Vynález popisuje termoplastický adukt epoxidovej živice a trietanolamínu o teplote maknutia 25 až 85 °C a amínovom čísle 80 až 200 mg KOH/g, pripravitetný reakciou epoxidovej živice na báze dianu o priemernej molekulovej hmotnosti do 900 s trietanolamínom v molárnom pomere, epoxidová živica : trietanolamínu rovnajúcom sa 1 : 1,2 až 2,3 pri teplote 120 až 200 °C a jeho soli s vo vodě rozpustnými kyselinami.The invention discloses a thermoplastic adduct of epoxy resin and triethanolamine having a melt temperature of 25-85 ° C and an amine number of 80-200 mg KOH / g, prepared by reacting a diane based epoxy resin of average molecular weight up to 900 with triethanolamine in molar ratio. equal to 1: 1.2 to 2.3 at 120 to 200 ° C and its salts with water-soluble acids.
Štruktúru aduktov podfa vynálezu nie je možné jednoznačné popísať obecným vzorcom. Z důvodu, že už samotné východzie epoxidové živice sú tvořené vačším počtom zlúčenín a sú dvojfunkčné, pri adičnej reakcii s trojfunkčným trietanolamínom vznikajú živice o zložitej, prevažne rozvetvenej štruktúre. Vzniknutá štruktúra je však podmienkou dosiahnutia účinku podfa vynálezu.The structure of the adducts of the invention cannot be clearly described by the general formula. Since the starting epoxy resins themselves are composed of a greater number of compounds and are bifunctional, the addition reaction with trifunctional triethanolamine results in resins having a complex, predominantly branched structure. However, the resulting structure is a prerequisite for achieving the effect of the invention.
Aby sa predišlo polymerizácii epoxidu na tuhý, netavitefný termoset, je výhodné trietanolamín přidávat k živici vyhriatej na reakčnú teplotu. Suroviny použité pri výrobě sú známe a bežne komerčně dostupné. Syntézu je vhodné viesť v tavenine bez přítomnosti organických rozpúšťadiel. Po klesnutí teploty násady pod 100 °C je výhodné adukt neutralizovat vo vodě rozpustnými kyselinami, pričom priemyselne má váčší význam kyselina octová a nariedit vodou na požadovaná koncentráciu. Týmto postupom sa odstránia hygienické a ekologické problémy, spojené s používáním organických riedidiel, nakofko adukty podta vynálezu sú polotuhej až tuhej konzistencie. Teplota maknutia sa merala metodou krúžok — gulička podfa CSN 65 7060.To avoid polymerization of the epoxide to a solid, non-fusible thermoset, it is preferred to add triethanolamine to the resin heated to the reaction temperature. The raw materials used in the production are known and commercially available. It is convenient to conduct the synthesis in the melt without the presence of organic solvents. After the feed temperature has fallen below 100 ° C, it is advantageous to neutralize the adduct with water-soluble acids, with acetic acid being more industrially important and diluting with water to the desired concentration. This procedure avoids the hygienic and ecological problems associated with the use of organic diluents, since the adducts of the invention are of a semi-solid to solid consistency. The annealing temperature was measured by the ring-ball method according to CSN 65 7060.
Vynález je ďalej objasněný formou príkladov.The invention is further illustrated by way of examples.
Příklad 1Example 1
Do banky opatrenej miešadlom a teplomerom sa předložilo 120 g epoxidovej živice na báze dianu o priemernej molekulovej hmotnosti 380. Živica sa vyhriala na 130 °C a za miešania sa přidal trietanolamín. Exotermom teplota násady vystúpila na 170 CC až 200 °C a udržovala sa po klesnutí na 130 °C 1,5 hod. Množstvo trietanolamínu a vlastnosti aduktov sú uvedené v tabulke 1.Into a flask equipped with a stirrer and a thermometer was charged 120 g of a dian based epoxy resin having an average molecular weight of 380. The resin was heated to 130 ° C and triethanolamine was added with stirring. The exotherm of the batch temperature rose to 170 ° C to 200 ° C and was maintained for 1.5 hours after falling to 130 ° C. The amounts of triethanolamine and adduct properties are given in Table 1.
Tabulka 1Table 1
K 50 g aduktu 1 vyhriateho na 90 °C sa přidalo 7,7 g kyseliny octovej a 109 g vody. Připravený číry roztok živice má pri 20 °C viskozitu 4 870 mPa . s a farbu 5 mg J2. K 50 g aduktu 5 sa přidalo pri 80 °C 6,2 g kyseliny octovej a 110,5 g vody. Roztok živice je číry s viskozitou pri 20 CC 598 mPa. s a farbou 6 mg J2.To 50 g of adduct 1 heated to 90 ° C were added 7.7 g of acetic acid and 109 g of water. The prepared clear resin solution has a viscosity of 4870 mPa at 20 ° C. take a color of 5 mg J2. To 50 g of adduct 5 was added at 80 ° C 6.2 g of acetic acid and 110.5 g of water. The resin solution is clear with a viscosity at 20 ° C of 598 mPa. with a color of 6 mg J2.
Příklad 2Example 2
Do banky sa předložilo 100 g epoxidovej živice na báze dianu o priemernej molekulovej hmotnosti 480. Po vyhriatí živice na 150 °C sa přidalo 62,2 g trietanolamínu a násada sa udržovala pri uvedenej teplote 2 hod. Připravený adukt o amínovom čísle100 g of Diane based epoxy resin having an average molecular weight of 480 were charged to the flask. After heating the resin to 150 ° C, 62.2 g of triethanolamine was added and the batch was kept at that temperature for 2 hours. Prepared amine number adduct
4747
143 mg KOH/g má teplotu maknutia 46 °C.143 mg KOH / g has a melting point of 46 ° C.
K 50 g aduktu sa pri 90 °C přidalo 8,6 g kyseliny octovej a 108,1 g vody. Připravený číry roztok aduktu má pri 20 °C viskozitu 43,2 mPa . s a farbu 5 mg J2.To 50 g of the adduct at 90 ° C were added 8.6 g of acetic acid and 108.1 g of water. The clear adduct solution prepared has a viscosity at 20 ° C of 43.2 mPa. with a color of 5 mg J2.
Příklad 3Example 3
Do banky sa předložilo 90 g epoxidovejThe flask was charged with 90 g of epoxy
4 živice na báze dianu o priemernej molekulovej hmotnosti 900. Po vyhriatí živice na 180 °C sa přidalo 30 g trietanolamínu a zohrievalo 2 hod. Připravený adukt o amínovom čísle 93 mg KOH/g má teplotu maknutia 69 °C. K 30 g aduktu sa pri 90 CC přidalo 4,5 g kyseliny octovej a 265,5 g vody. Vodný roztok připraveného aduktu má pri 20 °C viskozitu 1,7 mPa . s.After heating the resin to 180 ° C, 30 g of triethanolamine was added and heated for 2 hours. The prepared amine adduct of 93 mg KOH / g has a melting point of 69 ° C. 4.5 g of acetic acid and 265.5 g of water were added to 30 g of the adduct at 90 ° C. The aqueous solution of the prepared adduct has a viscosity of 1.7 mPa at 20 ° C. with.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS324285A CS247344B1 (en) | 1985-05-05 | 1985-05-05 | Thermoplastic adduct |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS324285A CS247344B1 (en) | 1985-05-05 | 1985-05-05 | Thermoplastic adduct |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS247344B1 true CS247344B1 (en) | 1986-12-18 |
Family
ID=5371929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS324285A CS247344B1 (en) | 1985-05-05 | 1985-05-05 | Thermoplastic adduct |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS247344B1 (en) |
-
1985
- 1985-05-05 CS CS324285A patent/CS247344B1/en unknown
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