PL97084B1 - Sposob wytwarzania nowych pochodnych benzotriazolu - Google Patents

Sposob wytwarzania nowych pochodnych benzotriazolu Download PDF

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PL97084B1
PL97084B1 PL1976186652A PL18665276A PL97084B1 PL 97084 B1 PL97084 B1 PL 97084B1 PL 1976186652 A PL1976186652 A PL 1976186652A PL 18665276 A PL18665276 A PL 18665276A PL 97084 B1 PL97084 B1 PL 97084B1
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carbon atoms
radical
formula
radicals
alkylene
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PL1976186652A
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    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • C07D249/18Benzotriazoles
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Description

Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych pochodnych benzotriaizolu majacych zdolnosc paisyiwoiwtania metali.Stosowanie pochodnych benzotriazolu do pasy- wowania metali, zwlaszcza miedzi, w róznych sro¬ dowiskach, jest znane od dawna. Jednakze stoso¬ wanie benzotatiazolu i wielu jego pochodnych do tego celu jest ograniczone, z powodu malej roz¬ puszczalnosci tych zwiazków, zwlaszcza w olejach mineralnych. Wad tyoh nie maja wytwarzane spo¬ sobem wedlug wynalazku nowe pochodne benzo¬ triazolu o ogólnym wzoTize 1, w którym X ozna¬ cza atom azotu lub grupe o wzorze =OR, w któ¬ rym R oznacza atom wodoru laib rodnik alkilowy o 1—4 atomlach wegla, A oznacza pierscien ben¬ zenowy lub naftalenowy, ewentualnie podstawio¬ ny jednym lub wieksza liczba rodników alkilo¬ wych o 1—12, zwlaszcza o 1—4 atomach wegla albo jednym lub wieksza liczba" rodników aral- kiiowych o 7—9 atomach wegla, zwlaszcza rodni¬ kiem a, a-dwanmetylobeozylowyim, a Rt i R2 sa jednakowe lub rózne i oznaczaja grupy o wzorze RsO[/alkileno/0]x —(alkilen), w którym R8 ozna¬ cza atom wodoru lub rodnik alkilowy o 1—20 atomach wefelfc, „alkilen" oznacza prosty lub roz¬ galeziony rodnik alkiienowy o 2 lub 3 atomach wegla, a x oznacza liczbe zero, 1, 2, 3 lub 4, albo Rt i R2 oznaczaja rodniki alkenylowe o 2—20 ato¬ mach wegla lub rodniki cyjanoalkilowe o 2—5 ato- mach wegla, albo tez Rx ma wyzej podane zna¬ czenie, a R2 oznacza atom wodoru, rodnik alkilo¬ wy o 1—20 atomach wegla, rodnik arylowy o 6—10 atomach wegla, rodnik cykloalkilowy o 5—12 ato¬ mach wegla, rodnik aralkilowy o 7—Q atomach wegla, rodnik heterocykliczny lub grupe o wzo¬ rze 2, w którym A i X maja wyzej podane zna¬ czenie.Sposobem wedlug wynalazku wytwarza sie rów¬ niez nowe zwiazki o wzorze objetym wzorem 1, a mianowicie griupe zwiazków jo wzorze la, w któ¬ rym X ma wyzej podane znaczenie, a korzystnie oznacza atom azotu, R4 i e£ sa. jednakowe lub rózne i oznaczaja rodniki alkilowe o 1—20 ato¬ mach wegla, rodniki arylowe o 6—10 atomach we¬ gla, rodniki cykloalkiiowe o 5—12 atomach we¬ gla, rodniki araikiiowe o 7—9 atoimach wegla lub rodniki heterocykliczne, a R6 oznacza rodnik aral¬ kilowy o 7—9 atomach wegla, korzystnie rodnik a, a^dwumetyilobeozylowy.Zwiazki o wzorze .1 sa zasadami ManniCha i ko¬ rzystne wlasciwosci majazwlaszcza te zwiazki o wzorze 1, w którym X oznacza atom azotu i A oznacza pierscien benzenowy, jak równiez zwiazki o wzorrze la, w którym wszystkie symbole maja wyzej podane znaczenie.Korzystnie jest równiez, gdy podstawnik przy atomie azotu w zwiazku o wzorze 1 tworzy funkcje polarna, a szczególnie, gdy co najmniej jeden z 970843 97084 4 pcwlstawników R± i R2, a zwlaszcza kazdy z nich, oznacza grupe o wzorze R80[/iailkii]]en/iO]x-/alikilen/, w którym R8 ma wyzej podane znaczenie, a ko¬ rzystnie oznaoza atom wodoru i x oznacza ko¬ rzystnieizero. 5 Gdy X oznacza grupe =C-R, w którym R ozna¬ cza rodnik alkilowy o 1—4 atomach wegla, wów¬ czas korzystnie R oznacza rodnik metylowy.Gdy A oznacza podstawiony rodnik fenylowy lub naftylowy, wówczas korzystnie jest to rodnik io fenylowy, zawierajacy jako podstawniki rodniki alkilowe o 1—4 atomach wegla, zwlaszcza rodniki metylowe, albo rodniki aralkilowe, zwlaszcza rod- mik a, a-dwumetylobenzylowy.Gdy Rt i/albo R2 oznaczaja rodniki alkenyilowe, 15 wówczas rodnika te zawieraja korzystnie 3—20 atomów wegla i oznaczaja na przyklad rodniki alkilowe, butenylowe, oktenylowe, decenylowe, do- decenylowe, tetradeoenylowe i oiktadecenyliawe (oleilowe). 20 Gdy Rj i/albo R2 oznaczaja grupy o wzorze R80[/alkilen/0]x/alkilen/, wówczas we wzorze tym R8 korzystnie oznacza atom wodoru lufo rodnik alkilowy o 1—18, zwlaszcza o 1—8 atomach we¬ gla, na przyklad grupy hydiroksyetylowe, meto- 25 ksyetylowe, n-butoksyetylowe, metoksyetoksyetylo- we, n-butoksyetoksyetylowe i nHoktyloksypropylo- ksyflowe. ' Jiako grupy cyjanoalkiilowe podstawniki R± i/albo R2 korzystnie oznaczaja grupy cyjanometylowe i cy- 30 %janoetylowe.Gdy Ri ma wyzej podane znaczenie, R2 moze tez oznaczac atom wodoru, rodmiik alkilowy, airy- lowy, cykloalkilowy, aralkilowy lub heterocyklicz¬ ny albo grupe o wzorze 2, w którym A i X maja 35 wyzej podane znaczenie.Gdy R2 oznacza rodnik alkilowy, to korzystnie zawiera on 1—12 atomów wegla, jako rodndk ary- lowy oznaoza korzystnie rodmiik fenylowy lub naf- tyloiwy, jako rodnik cykloadfciilowy oznacza zwlasz- 40 cza rodnik cykloheksylowy, jako rodnik arailkilo- wy oznacza korzystnie rodnik benzylowy, a jiako irodndk heterocykliczny zwlaszcza rodnik piperydy- nowy lub morfolinowy.R4 i R5 korzystnie maja znaczenie podane wy- 45 zaj dla R2.Najkorzystniejsze wlasciwosci maja jednak zwia¬ zki o wzorze 1, w którym A oznacza pierscien ben¬ zenowy, ewentualnie podstawiony rodnikiem me¬ tylowym lub dwumetylobenzylowym, a Ri i R2 sa 50 jednakowe lub rózne i oznaczaja grupy o wzorze R^O[/alkilen/0]x-/alkilen/, w którym R8 oznacza a/tom wodoru lub nizszy rodnik alkilowy, a x ko¬ rzystnie oznacza zero, albo Ri oznacza grupe o tym wzorze, a R2 oznacza atom wodoru lub niz- 55 szy rodnik alkilowy.Przykladami zwiazków wytwarzanych sposobem wedlug wynalazku sa nastepujace zwiazki: 1Hdwuetanoloamliinlometylobenzotriaizol, lndwuetanoloaminomety^beinziimiidazioi, 60 lHdwutiizopropanoloamiinlom 1^dwiuizoprjopanoloamiinomety^ N,Nnbis/!l'-foenzotriazolailometylo/^etan^ N,Njbis^l%benziimidaizolilarr^ na, 65 N,N^bis/l%ber^otriazo'M'lometyW4 na, 1-/N^metyloetanoloamiinometylo/-benzotriazol, NjNHbis/r-lbeniztaidazol^ butanol, N,N^is/l/^benzimidiazolilometylo/-3-metoksypropy- loamina, l-dwualJiloajndinjometylo-2-butylobenziinidazol, l-/NHmety]oe4anoloamiinome daizol, N,N-ibdisyir^benGotriazoiiloimetylo/-etoiksyetoiksyp(ro- ipyloamiina, N,N-'bis tt,N-fo,is/l%benizotriaz0lilometylo/^^ N,N-ibiis/il'^Denzotaiazolilometylo/^allitó NjN^iMsi/^S-iaya^diwuimetylObenzylo-l^benzotriazolilo- metyilo/^dodecyloaimina i Wdwunn-ibutyilloamiinometylo/^^ benzyiloZ-benzotriazol.Sposobem (wedlug wynalazku zwiazki o wzorze 1, w którym wszystkie symbole maja wyzeó po¬ dane iznaozenie, wytwarza sie przez reakcje zwiaz¬ ku o wzorze 3, w którym A i X maja wyzej po¬ dane znacznie, z aldehydem mrówkowym i z ami¬ na o wzorze 4, w którym Rj i A maja wyzej po¬ dane znacznie.Zwiazki o wzorze 3, nadajace sie jako produkty wyjsciowe w tym procesie, obejmuj% benzotria- • zole, benzimidazole i zwiazki znane z brytyjskiego opisu patentowego benzoitriazole. Korzystnie jednak jako zwiazek o wzorze 3 stosuje sie sam benzotriazol.Aldehyd mrówkowy korzystnie stosuje sie w ta¬ kiej postaci, w j«akiej wystepuje on w handlu, na przyklad w postaci formaliny lub papaformalde- hydu.Przykladami odpowiednich amin o wzorze 4 sa aminy pierwszorzedowe o wzoirze RiNH2, w któ- ryim iRt ima wyzej podane znaczenie i drugotize- dowe aminy o wzorze (Ri) (/R2) NH, w którym Rt i R2 maja wyzej podane znaczenie.Skladniki reakcji, to jest zwiazki o wzorach 3 i 4 oraz aildehyd mrówkowy, stosuje sie w róz¬ nych stosunkach wzajemnych, w zaleznosci od te¬ go, czy zwiazek o wzorze* 4 jest amina pierwszo- rzedowa czy dnugorzedowa. Jezeli zwiazek o wzo¬ rze 4 jest amina ipienwiszorzedowa, to stosunek mo¬ lowy zwiazku o wzorze 3, aldehydu mrówkowego i aminy io wzorze 4 moze zasadniczo wynosic 2,0 : 2,0 :1,0 albo 1,0 :1,0 :1,0 zas gdy zwiazek o wzoirze 4 jest amina drugorzedowa, to stosunek ten wynosi korzystnie zasadniczo 1,0 :1,0 :1,0.Slposobem wedlug wynalazku proces prowadzi sie korzystnie utrzymujac wszystkie skladniki re¬ akcji w podwyzszonej temperaturze, na przyklad 50—il20°C. W razie potrzeby mozna najpierw pod¬ dawac reakcji zwiazek o wzorze 3 z aldehydem mrówkowym i otrzymany izwiazek N-imetylolowy poddawac reakcji z aimina o wzorze 4.Stwierdzono, ze zwiazki o wzorach 1 i la, w których wszystkie symbole maja wyzej podane zniaczenie, maja bardzo dobra zdolnosc ipasywo- wania metali, a równoczesnie sa dobrze rozpusz¬ czalne w wielu cieczach stosowanyah do róznych celów tjotez nadaja sie do wytwarzania srodków97084 do pasywowania metali. Srodka tafcie korzystnie zawieraja 0,001—&/o wagowych zwiazku o wzorze 1 lub la w stosunku do calkowitej masy.Przykladami cieklych czynników stosowanych w takich sirodkach sa smary na podstawie oleju mi¬ neralnego lub syntetycznego eatru kar.boksyilowego, ciecze hydrauliczne na podstawie olejów mineral¬ nych, estirów fosforanowych, wodnych (mieszanin poiiiglikolu z estrem poliglikolowym, ukladSw gli- kolowych, albo emulsja typu olej w wodzie albo woda w oleju, jiak równiez ciecze stosowane przy obróbce metali, majace jako podstawe oleje mi¬ neralne lub ulady wodne, a takze wodno-giikloilowe srodki zapobiegajace zamarzamiiu.W zaleznosci od rodzaju cieklego czynnika srod¬ ki te zawieraja jeden lub wieksza liczbe dodat¬ ków. Przykladami takich dodatków w cieklych czynnikach nie opartych na wodzie sa antyutle- niacze, inne pasywatory metali, initabfiltory rdzy, substancje polepszajace lepkosc, substancje obni- zaijace (temperature plynnosci, dyspergaifcory, de¬ tergenty i dzialajace pod wysokim cisnieniem sub- istanicje przeoiwscierne.Przyklady I—XIV. 23,82 czesci benzotriazolu i 21,03 czesci dwuetanoioaminy miesza sie z 75 czesciami etanolu i "6,0 czesciami aldehydu mrów- ^JbOfwego, dodanego w postaci 36«/o roztworu wod¬ nego i mieszanine -utrzymuje w stanie wrzenia pod idhlodndca zwrotna w ciagu 8 godzin, po iczyim chlo¬ dzi i odparowuje rozpuszczalnik pod cisnieniem obnizonym za pomoca stoumieniowej pampy wod¬ nej. Pozostalosc przedestylowuje sie pod takim -sa¬ mym cisnieniem azeotropowOj stosujac 3 porcje po 50 ml etanolu. Otrzymuje sie 1-dwuetanoloami- no-metylobenzotriazol z wydajnoscia wynoszaca 0W0 wydajnosci iteoretycznej.Dalsze próby prowadzi sie w sposób analogiczny do wyzej opisanego, przy czyni jezeli jako pro¬ dukt wyjsciowy stosuje sie amine pierwszarze- ckarwa, to ilosc jej w stosunku molowym jest o po¬ lowe mniejsza. W przypadku stosowania amin o wyzszych ciezarach czasteczkowych, w celu uzy¬ skania dobrej wydajnosci reakcje prowadzi sie w czasie dluzszym od 8 godzin, a mianowicie do okolo 16 godzin. Jezeli otrzymane produkty sta¬ nowia ciala stale, to korzystnie przekiryat&lizorwuje rie je z octanu etylu.Otozyirnane zwiazki sa przewaznie zwiazkami podstawionymi przy atomie azotu w pozycji 1, aczkolwiek widmo rnagnetyoznego rezonansu ja¬ drowego wykazuje, ze w pewnej mierze (do 20§/o) powstaja równiez produkty podstawione przy ato¬ mie azotu w pozycji 2.W tablicy 1 podano zwiazki o wzorze 1, w któ¬ rym A oznacza pierscien benzenowy, wytworzone z drugorzedowych amin, w tablicy 2 — zwiazki o wzorze 5 wytworzone z pierwszorzedowych amin i w tablicy 3 — zwiazki o wzorze 6 otrzymane z drugorzedowych amin (modyfikowane benzo- triazoie). Znaczenie symboli we wzorach podano w tablicach, w których tez podano wyniki analizy elementarnej produktów, przy czym waartosci po¬ dane w górnym wierszu stanowia wartosci obli¬ czone teoretycznie, a w dolnym wierszu wartosci otrzymane w wyniku analizy. 3 fcl 1 1* 11 ni IV V VI X N CH N CH N CH Ki 7 -CH2CH2OH -CH2CH2OH -CHaCH^CH -CH2CH2OH —CH2CH^OH2 -CHjiCH=CH2 1 . 1R2 -CH2CH2OH -CH^HjOH -CHS -CH8 -\^Hf\*ix ^ C^Hj -CHflCH= CHj Tabl •0 f . 80 72 95 62 ' 71 91 i ca 1 Konsys¬ tencja iproduktu cialo stale cialo stale syrop cialo stale olej olej • Tempera¬ tura top¬ nienia lub wrzenia °C /2—54 00—01 — 79—80 temperatu¬ ra wrzenia il26°C/0,4 mim Hg C 55,93 55,56 61,28 61,24 58,25 58,20 64,39 64,10 68,42 68,19 74,01 73,38 Analiza °; H 6,78 6,88 7,23 7,37 6,80 6,49 7,32 7,42 7,01 7,27 7,49 7,67 <9 1 N I 4 m 23,73 23,55 17,87 17,60 2748 ft7,98 ,49 ,21 24,56 24,83 18,50 18,7697084 Tatoli ca 2 3 ST lad i* a i.VII VIII IX X XI XII X N CH N CH N CH R -Ci8HS5 -CisH,5 -CHgCH =CH2 -OH2CH=CH2 -CH^OCH, -CHs/jrOCH, Wydajnosc °/o 90 95 76 82 75 68 Konsystencja produktu wosk syrop cialo stale cialo stale cialo stale cialo stale Tempera¬ tura top¬ nienia °C — czystosci 114—115 111—112 98—100*) 120—121 C 72,59 72,21 Analiza ° H 8,88 9,12 /o N 18,53 18,46 produktu tylko 90% 63,95 63,91 71,92 72,12 61,54 60,56 74,01 73,88 ,33 ,48 ,99 6,23 ,98 ,99 7,49 7,67 ,72 ,84 22,08 22,09 '27,92 27,57 18,50 18,76 * po przekrystalizowaniu z etanolu Tablica 3 3 Nume przyk XIII XIV Ri n-C4H9 C13H27" R2 n-C4H9 C1SH27" Wydajnosc •/• 91 91 Konsysten¬ cja pro¬ duktu syrop syrop Tempera¬ tura top¬ nienia — C 76,19 75,88 80,00 79,61 Analiza °/o H 8,99 9,02 11,35 11,35 _ N 14,81 14,80 8,89 8,94 "C13Hfr7„ oznacza srednia wartosc rodników alkilowych w preparacie Kemamine S 650 firmy Hunka Che¬ mical Products PL

Claims (2)

  1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych ben- zotiriazolu o ogólnym wzorze 1, w którym X ozna¬ cza latam azotu lub grupe o wzorze =C-R, w któ¬ rym R oznacza atom wodoru lub rodnik alkilowy o .1—4 atomach wegla, A oznacza pierscien ben¬ zenowy lub naftalenowy, ewentualnie podstawio¬ ny jednym lub wieksza liczba rodników alkilo¬ wych o 1^12 atomach wegla albo jednym lub wieksza liczbo rodników arialkilowyoh o 7—9 ato¬ mach V wegla, a Ri ii ,R2 sa jednakowe lub rózne i oznaczaja grupy o wzorze R^O[/alkilen/0]x-/alki- len/, w którym R8 oznacza atom wodoru lub rod¬ nik lalikilowy o 1—20 atomach wegla, alkilen ozna¬ cza rodnik alkilenoiwy o lancuchu prostym lub rozgalezionym, zawierajacym 2 lub 3 atomy we¬ gla, a x oznacza liczbe zero, 1, 2, 3 albo^ 4, albo 45 Ri i R2 oznaczaja, rodniki alkenylowe o 2—20 ato¬ mach wegla lub rodniki cyjamoalkiipfwe o 2—5 atomach wegla, albo tez Ri ma wyzej podane zli¬ czenie, a R2 oznacza atom wodoru, rodnik alkilo¬ wy o 1—20 atomach weglia, rodnik aryloiwy o 6—10 5° atomach wegla, rodnik cykloalkilowy o 5—12 ato¬ mach wegla, rodnik aralkilowy o 7—9 atomach wegla, rodnik heterocykliczny lub grupe o wzo¬ rze 2, w którym A i X maja wyzej podane zna¬ czenie, znamienny tym, ze zwiazek o ogólnym wzo- 55 rze 3, w którym A i X maja wyzej podane zna¬ czenie, poddaje sie reakcji z aldehydem mrówko¬ wym i ze zwiazkiem o ogólnym wizorze 4, w któ¬ rym Rx i R2 maja wyzej podane znaczenie.
  2. 2. Sposób wedlug zastrz. 1, znamienny tym, ze 60 jako zwiazek o wzorze 3 stosuje sie benzotriazol.97084 *xN^ R< CH2N^ ¦R« ¦R. Hzar fa rN, -n\: XH2- tizór Z AJ H- rNkY LN/X (i Vitor 5 -N<^ Wzór 4 VR297084 ;x CH; NR Wzór 5 CH*N' Wzdrc R< R2 Drukarnia Narodowa Zaklad Nr 6, zam. 219/78 Cena 45 zl PL
PL1976186652A 1975-01-23 1976-01-20 Sposob wytwarzania nowych pochodnych benzotriazolu PL97084B1 (pl)

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DE2601719A1 (de) 1976-07-29
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CH597198A5 (pl) 1978-03-31
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CA1077047A (en) 1980-05-06
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