CS220290B1 - High molecular weight copolyaminohydroxyether bitumina - Google Patents
High molecular weight copolyaminohydroxyether bitumina Download PDFInfo
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- CS220290B1 CS220290B1 CS861481A CS861481A CS220290B1 CS 220290 B1 CS220290 B1 CS 220290B1 CS 861481 A CS861481 A CS 861481A CS 861481 A CS861481 A CS 861481A CS 220290 B1 CS220290 B1 CS 220290B1
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- Czechoslovakia
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- molecular weight
- copolyaminohydroxyether
- high molecular
- resin
- bitumina
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- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 206010003645 Atopy Diseases 0.000 claims 1
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 description 13
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 3
- 229940043276 diisopropanolamine Drugs 0.000 description 3
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 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 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical class NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
Vynález sa týká vysokomolekulárnych kopolyaminohydroxyéterových živíc a ich adičných solí s vo vodě rozpustnými kyselinami.The invention relates to high molecular weight copolyaminohydroxyether resins and their addition salts with water-soluble acids.
S neustálým rastom výroby stále nových, skleněným vláknom vystužených plastov a s vývojom technologii výroby Iaminátov je úzsko spatý aj vývoj povrchových úprav skleněných vlákien a s ním spojený vývoj róznych lubrikačných zložiek. Použitie priamych lubrikácií je známy spósob úpravy skleněných vlákien, ktorý však prináša so sebou celý rad problémov s výberom a syntézou róznych lubrikačných látok.With the constant growth in the production of new glass fiber reinforced plastics and the development of laminate technology, the development of glass fiber surface treatments and the development of various lubricating components are closely linked. The use of direct lubricants is a known method for treating glass fibers, which, however, presents a number of problems with the selection and synthesis of different lubricants.
Významné uplatnenie v tomto obore ako filmotvorné látky s vysokou odolnosťou voči abrázií a dobrými klznými vlastnosfami našli kopolyaminohydroxyéterové živice, zvlášť na báze díalkanolamínov, alifatickýchCopolyaminohydroxyether resins, especially based on dialkanolamines, aliphatic resins, have found significant application in this field as film-forming substances with high abrasion resistance and good slip properties.
HOCH2CHX \HOCH2CHX \
//
HOCH2CHX polyamínov a nízskomolekulárnych epoxidových živíc na báze diánu. Avšak aj tieto živice nemajú univerzálně použitie. Sú vhodné k úpravě skleněných vlákien používaných k výrobě tkanin pře potřeby elektropriemyslu, no nevhodné pre spracovanie vlákien k výrobě prepregov alebo technológiou striekanía. Pri týchto postupoch sa vyžaduje zvýšená tuhost a pružnost prameňa skleněných vlákien, ktorá zlepšuje ich sekateínosť pri róznych technologických operáciách. Při aplikačnom výskume sme zistili, že týmto náročným požiadavkám vyhovujú živice pódia vynálezu.HOCH2CHX polyamines and low molecular weight epoxy resins based on dianes. However, these resins are not universally used. They are suitable for treating glass fibers used to produce fabrics for the electrical industry, but not suitable for fiber processing for prepreg production or spraying technology. These processes require increased stiffness and elasticity of the glass fiber strand, which improves their susceptibility to various technological operations. In application research, we have found that the resins of the invention meet these demanding requirements.
Vynález popisuje nové vysokomolekulárne kopolyaminohydroxyéterové živice obecného vzorcaThe present invention provides novel high molecular weight copolyaminohydroxyether resins of the general formula
OH OHOH OH
I I sCHCHa—M—CH2CHCH2NH—R1—NHR2CHCH2-M-CH2CHCH2NH-R1-NHR2
22029Θ kde M je zbytok o štruktúreWhere M is a residue of structure
X je atóm vodíku alebo metyl,X is hydrogen or methyl,
Ri je alkylénový Či izoalkylénový zbytok s 2 až 6 atómami uhlíka alebo zbytok o štruktúreR 1 is an alkylene or isoalkylene radical having 2 to 6 carbon atoms or a radical of structure
-R3-NH-R 3 -NH
R2 je atém vodíka alebo zbytok o štruiktúreR 2 is a hydrogen atom or a radical of structure
řř>řř>
—CH2( OH 1CHCH2MCH2Í OH 1CHGH2N {XCHCH2OH )2—CH 2 (OH 1 CHCH 2 MMCH 2 OH 1 CHGH 2 N (XCHCH 2 OH) 2
Rí je alkylénový zbytok s 2 alebo 3 atómami uhlíka, nje 3 až 13, m je 1 až 3, a ich adičné soli s vo vodě rozpustnými kyselinami.R 1 is an alkylene radical having 2 or 3 carbon atoms, n is 3 to 13, m is 1 to 3, and their addition salts with water-soluble acids.
Základný štruuktúrny skelet týchto živíc je vytvořený z epoxidových zbytkov na báze diánu a epichlórhydrínu o priemernej molekulovej hmotnosti 1200 až 4100.The basic structural skeleton of these resins is formed from epoxy residues based on dian and epichlorohydrin having an average molecular weight of 1200 to 4100.
Přípravu živíc podlá vynálezu možno uskutočniť nasledovným postupom. Reakciou epoxidovej živice s alkanolamínom obecného vzorcaThe preparation of the resins according to the invention can be carried out as follows. Reaction of the epoxy resin with an alkanolamine of formula
t. j. za použitia dietanolamínu alebo diizopropanolamínu sa připraví monoepoxid. Poměr reaktantov sa riadi stechlometriou reakcie a adíciu je výhodné viesť v prostředí vo vodě rozpustného organikého rozpúšťadla. Výhodné je použit éteralkoholy s 3 až 5 atómami uhlíka ako etylénglykolmonoetyléter, etylénglykolmonometyléter, etylénglykolmono-n-propyléter, dioxán a pod. pri teplote 50 °C až pri bode varu rozpúšťadla. Takto připravené monoepoxidy sa podrobia reakcii s alifatickými polyamínami obecných vzorcov:t. j. monoepoxide is prepared using diethanolamine or diisopropanolamine. The ratio of the reactants is controlled by the reaction stechlametry and the addition is preferably conducted in a water-soluble organic solvent. Preferred are C 3 -C 5 ether alcohols such as ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, ethylene glycol mono-n-propyl ether, dioxane and the like. at 50 ° C to the boiling point of the solvent. The monoepoxides thus prepared are reacted with aliphatic polyamines of the formulas:
HN(XCHCH2OH]2 ,HN (XCHCH 2 OH) 2,
NH^Rf NH^ & NI-L--R-NU príkladom ktorých je etyldiamín až hexametyléndiamín, dietyléntriamín, dipropyléntriamín, trietyléntetramín, tetraetylénpentamín v molárnom pomere monoepoxid : : polyamín rovnajúcom sa 1 až 2 :1. Polyamíny je možné používat nielen v čistej formě, ale aj vo formě technických produktov aminolýzy chlórovaných uhlovodíkov. Přípravu adičných solí vo vodě rozpustných kyselin, či už minerálnych alebo organických je možno uskutečnit’ jednoduchým zmiešaním roztoku živice s kyselinou buď tesne po ukončení syntézy alebo pre ich aplikačným použitím.NH ^Rf NH ^ &NI-L-R-NU exemplified by ethyldiamine to hexamethylenediamine, diethylenetriamine, dipropylenetriamine, triethylenetetramine, tetraethylenepentamine in a monoepoxide: polyamine molar ratio of 1 to 2: 1. Polyamines can be used not only in pure form, but also in the form of technical products of aminolysis of chlorinated hydrocarbons. The preparation of water-soluble acid addition salts, whether mineral or organic, can be accomplished by simply mixing the resin solution with the acid either immediately after the synthesis or for their application.
Vynález je ďalej objasněný formou príkladov v ktorých zloženie je uvádzané v hmotnostnej koncentrácii.The invention is further elucidated by way of examples in which the composition is given in weight concentration.
Příklad 1Example 1
Do sklenenej banky s miešadlom, spatným chladičom, kontaktným teplomerom a oddělovacím lievikom sa předložilo 1500 g 50% roztoku epoxidovej živice na báze dianu a priemernej molekulovej hmotnosti 1500 v etylénglykolmonoetylétery (etylglykol). Z oddelovacieho lievika pri teplote 50 °C sa přidalo 105 g 50% dietanolamínu v etylglykole a násada sa udržovala pri miernom refluxe 1,5 hod. K 300 g roztoku monoepoxidu sa přidal polyamín a etylglykol v hmotnostnom pomere 1:1a násada sa zahrievala pri teplote refluxu 2 hodiny. Navážky polyamínov a vlastností živíc sú uvedené v tabulke I.A glass flask with stirrer, reflux condenser, contact thermometer, and separatory funnel was charged with 1500 g of a 50% diane based epoxy resin solution and an average molecular weight of 1500 in ethylene glycol monoethyl ethers (ethyl glycol). 105 g of 50% diethanolamine in ethyl glycol were added from a separatory funnel at 50 ° C and the batch was maintained at gentle reflux for 1.5 hours. To a 300 g monoepoxide solution was added polyamine and ethyl glycol in a 1: 1 weight ratio and the batch was heated at reflux temperature for 2 hours. The weights of polyamines and resin properties are given in Table I.
TABULKA ITABLE I
Stanovenie viskozity sa robilo podía ČSN 67 3014 a určenia farby podía ČSN 67 3011.Determination of viscosity was made according to ČSN 67 3014 and color determination according to ČSN 67 3011.
Příklad 2Example 2
Do banky sa pedložilo 300 g roztoku monoepoxidu připraveného podía příkladu 1 a 19 g 50 % roztoku technickej zmesi alifatic-etylglykole o zložení uvedenom v tabufke II.The flask was charged with 300 g of the monoepoxide solution prepared according to Example 1 and 19 g of a 50% solution of the aliphatic-ethylglycol technical composition of the composition shown in Table II.
TABULKA IITABLE II
Násada sa zahriala pri miernom refluxe 2 hodiny. Živica má viskozitu pri 20 °C 3099 bPa . s a farbu 10 mg J2.The batch was heated at moderate reflux for 2 hours. The resin has a viscosity at 20 ° C of 3099 bPa. with a color of 10 mg J2.
Příklad 3Example 3
Do banky sa předložilo 1000 g 50% roztoku epoxidovej živice na báze dianu o priemernej molekulovej hmotnosti 1200 v etylglykole. Z oddelovacieho lievika sa přidalo 88 g 50 % dietanolaminu v etylglykole a násada sa udržovala pri miernom refluxe 1,5 hod. K 300 g roztoku monoepoxidu sa přidal polyamín a etylglykol v hmotnostnom pomere 1:1 a násada sa zahrievala pri teplote refluxu 2 hodiny. Navážky polyamínov a vlastností živíc sú uvedené v tabulke III.The flask was charged with 1000 g of a 50% solution of an epian resin based on diane with an average molecular weight of 1200 in ethyl glycol. 88 g of 50% diethanolamine in ethyl glycol were added from the separatory funnel and the batch was maintained at gentle reflux for 1.5 hours. To a 300 g monoepoxide solution was added polyamine and ethyl glycol in a 1: 1 weight ratio and the batch was heated at reflux temperature for 2 hours. The weights of polyamines and resin properties are given in Table III.
TABULKA III.TABLE III.
Polyamín Navážka (%) Viskozita Farba (mg Jz) (mPa.s/20 CC)Polyamine Weight (%) Viscosity Color (mg Jz) (mPa.s / 20 C C)
Příklad 4Example 4
Násada:handle:
200 g epoxidovej živice na báze dianu o priemernej molekulovej hmotnosti 3800, g diizopropanolamínu,200 g of Diane based epoxy resin with an average molecular weight of 3800, g of diisopropanolamine,
7,7 g trietyléntetramínu,7.7 g triethylenetetramine,
215 g etylénglykolmono-n-butyléteru (butylglykol).215 g of ethylene glycol mono-n-butyl ether (butyl glycol).
Do banky sa předložila živica a butylglykol. Po jej rozpuštění sa přidal diizopropanolamín a násada sa zahrievala pri 120 °CThe resin and butyl glycol were charged to the flask. After dissolution, diisopropanolamine was added and the batch was heated at 120 ° C
1,5 hodiny. Z oddelovacieho lievika sa přidal trietyléntetramín a násada sa udržovala na 130 °C 2 hodiny. Připravená živica má viskozitu pri 20 °C 39 560 mPa . s a farbu 4 mg J2.1.5 hours. Triethylenetetramine was added from the separatory funnel and the batch was maintained at 130 ° C for 2 hours. The prepared resin has a viscosity at 20 ° C of 39,560 mPa. s and a color of 4 mg J2.
o priemernej molekulovej hmotnosti 3800,with an average molecular weight of 3800,
5,5 g dietanolaminu, g tetraetylénpentamínu,5,5 g diethanolamine, g tetraethylenepentamine,
216 g butylglykolu.216 g of butyl glycol.
Do banky sa předložila živica a butylglykol. Po jej rozpuštění sa přidá dietanolamín a násada sa zahrievala pri 120 °C 1,5 hodiny. Z oddelovacieho lievika sa přidal polyamín a násada sa udržovala při 130 °C 2 hodiny. Připravená živica má viskozitu pri 20 °C 57 550 mPa . s a farbu 6 mg J2.The resin and butyl glycol were charged to the flask. After dissolution, diethanolamine was added and the batch was heated at 120 ° C for 1.5 hours. Polyamine was added from the separatory funnel and the batch was kept at 130 ° C for 2 hours. The prepared resin has a viscosity at 20 ° C of 57,550 mPa. with a color of 6 mg J2.
Příklad 6Example 6
Živica připravená podl'a příkladu 2, v množstve 30 g sa zmiešala s kyselinou a přidala do 500 ml vody. Navážky kyselin a vlastnosti roztokov sú uvedené v tabulke IV.The resin prepared according to Example 2, in an amount of 30 g, was mixed with acid and added to 500 ml of water. The acid weights and solution properties are shown in Table IV.
Přiklad 5Example 5
Násada:handle:
200 g epoxidovej živice na báze dianu200 g of epian resin based on diane
220293220293
Kyselinaacid
TABULKA IVTABLE IV
Navážka (g) Vlastnosti roztoku octová mravčia (85 °/o)Weight (g) Properties of the formic acid solution (85 ° / o)
1,71.7
1,5 opalescentný opalescentný1.5 opalescent opalescent
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861481A CS220290B1 (en) | 1981-11-24 | 1981-11-24 | High molecular weight copolyaminohydroxyether bitumina |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861481A CS220290B1 (en) | 1981-11-24 | 1981-11-24 | High molecular weight copolyaminohydroxyether bitumina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS220290B1 true CS220290B1 (en) | 1983-03-25 |
Family
ID=5436954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS861481A CS220290B1 (en) | 1981-11-24 | 1981-11-24 | High molecular weight copolyaminohydroxyether bitumina |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS220290B1 (en) |
-
1981
- 1981-11-24 CS CS861481A patent/CS220290B1/en unknown
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