NO117673B - - Google Patents
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- Publication number
- NO117673B NO117673B NO147520A NO14752063A NO117673B NO 117673 B NO117673 B NO 117673B NO 147520 A NO147520 A NO 147520A NO 14752063 A NO14752063 A NO 14752063A NO 117673 B NO117673 B NO 117673B
- Authority
- NO
- Norway
- Prior art keywords
- sulfonamide
- diazo
- oxo
- aromatic
- dehydroabiethyl
- Prior art date
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- -1 aromatic diazoxide sulfonamide Chemical class 0.000 claims description 24
- 229940124530 sulfonamide Drugs 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229960004042 diazoxide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical group C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- QMFJIJFIHIDENY-UHFFFAOYSA-N 1-Methyl-1,3-cyclohexadiene Chemical compound CC1=CC=CCC1 QMFJIJFIHIDENY-UHFFFAOYSA-N 0.000 description 1
- GHRZOGONMXDLAP-UHFFFAOYSA-N 1-bromocyclohexa-1,3-diene Chemical compound BrC1=CC=CCC1 GHRZOGONMXDLAP-UHFFFAOYSA-N 0.000 description 1
- GGYAEMVRZZZXGB-UHFFFAOYSA-N 1-chlorocyclohexa-1,3-diene Chemical compound ClC1=CC=CCC1 GGYAEMVRZZZXGB-UHFFFAOYSA-N 0.000 description 1
- WZMQOSYJAAMGTB-UHFFFAOYSA-N 1-ethylcyclohexa-1,3-diene Chemical compound CCC1=CC=CCC1 WZMQOSYJAAMGTB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XPWAKFLHVWAWNO-UHFFFAOYSA-N 4-chlorosulfonyl-2-diazoniophenolate Chemical compound [O-]C1=CC=C(S(Cl)(=O)=O)C=C1[N+]#N XPWAKFLHVWAWNO-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical compound NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YUGZXRNLJAFTPK-UHFFFAOYSA-N cyclohexa-1,5-diene-1-sulfonamide Chemical compound C1CC=CC(=C1)S(=O)(=O)N YUGZXRNLJAFTPK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/10—Bleaching ; Apparatus therefor
- D21C9/1026—Other features in bleaching processes
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Description
Lysfølsomt materiale. Light-sensitive material.
Denne oppfinnelse angår lysfølsomme This invention relates to photosensitive
materialer fremstilt under anvendelse av materials produced using
diazo-oksyder av aromatiske sulfonamider diazo-oxides of aromatic sulfonamides
i hvilke amidkvelstoffet er substituert av in which the amide nitrogen is substituted by
et alicyklisk radikal av høy molekylvekt. a high molecular weight alicyclic radical.
Diazo-oksyder av aromatiske sulfonamider med substituenter av høy molekylarvekt på amidkvelstoffet er blitt anbe-falt til bruk i litografi, og i denne forbindelse skal det henvises eksempelvis til de Diazo oxides of aromatic sulfonamides with high molecular weight substituents on the amide nitrogen have been recommended for use in lithography, and in this connection reference should be made, for example, to the
tyske patenter nr. 854.890, 865.108, 865.410, German Patent Nos. 854,890, 865,108, 865,410,
871.668, 872.154, 879.205 og lignende. Blant 871,668, 872,154, 879,205 and the like. Among
de stoffer som omfattes av disse patenter the substances covered by these patents
er substituentene på det nevnte kvelstoff-atom enten alkyl eller aryl. Disse forbindelser har, som klasse betegnet, en blan-det polar til ikkepolar karakter, og er av the substituents on said nitrogen atom are either alkyl or aryl. These compounds have, as a class term, a mixed polar to non-polar character, and are of
denne grunn praktisk talt bare oppløselige this reason practically only soluble
i meget kraftig virkende oppløsningsmid-ler, som f. eks. dimetylformamid, dimetyl-acetamid, dioksan og metylcellosolve. Disse in very powerful solvents, such as e.g. dimethylformamide, dimethylacetamide, dioxane and methylcellosolve. These
forbindelser har fordelaktige egenskaper compounds have beneficial properties
med hensyn til sensitivering av plater for with regard to sensitizing plates for
litografi, på grunn av deres oppløselighets-forhold, men de skaffer et problem når de lithography, due to their solubility conditions, but they present a problem when they
skal anvendes i forbindelse med forskjellige shall be used in connection with different
harpikssubstrater. Grunnen hertil er den, resin substrates. The reason for this is that,
at' de kraftig virkende oppløsningsmidler that' the powerful solvents
som behøves for å legge ned disse sensiti-veringsmidler trenger gjennom og sveller which is needed to put down these sensitizers penetrates and swells
eller løser opp harpikssubstratet, hvorved or dissolves the resin substrate, whereby
trykkflaten skades. Det foreligger derfor the pressure surface is damaged. It is therefore available
avgjort et behov for høymolekylære diazo-oksyder som til tross for det ovennevnte determined a need for high molecular weight diazo oxides which despite the above
kan avsettes som belegg på harpikssubstrater fra forholdsvis enkle organiske opp-løsningsmidler, f. eks. fra alkylestere, keto-ner og lignende. can be deposited as a coating on resin substrates from relatively simple organic solvents, e.g. from alkyl esters, ketones and the like.
Tysk patent nr. 879.205 gir ingen løs- German patent no. 879,205 provides no solution
ning av dette problem. De eneste diazo-oksyder av aromatiske sulfonamider som nevnes i dette patent er nemlig de som er avledet fra |5-naftylamid. Det turde være selvinnlysende at det ikke foreligger noen ning of this problem. Namely, the only diazo oxides of aromatic sulfonamides mentioned in this patent are those derived from β-naphthylamide. It should be self-evident that there are none
likhet i strukturen av naf tylamid-halvdelen similarity in the structure of the naphthylamide moiety
og de høymolekylære alicykliske halvdeler som den foreliggende oppfinnelse dreier seg om. and the high molecular weight alicyclic moieties to which the present invention relates.
Denne strukturforskjell gir seg også til kjenne ved en forskjell i diazooksydenes egenskaper. I det tyske patent nevnes som det eneste oppløsningsmiddel for dets diazooksyder dioksan, og i denne forbindelse This structural difference is also manifested by a difference in the properties of the diazo oxides. In the German patent, dioxane is mentioned as the only solvent for its diazo oxides, and in this connection
henvises det til eksempel I. Dette er et meget kraftig oppløsningsmiddel, hvilket refer to example I. This is a very powerful solvent, which
fremgår av at det er i stand til å oppløse de harpikser som er nevnt av patentinne-haveren. Diazooksydene i nærværende krav derimot er oppløselige i enkle organiske opløsningsmidler, som ikke har noen innvirkning på harpikssubstrater. Det foreligger derfor en klar forskjell mellom oppfinnelsen i det tyske patent og i kravet. I Oppfinnerne har funnet, at diazo-oksyder av aromatiske sulfonamider, i hvilke substituenten på amidokvelstoffet er et høymolekylært alicyklisk radikal, har meget fordelaktige egenskaper som sensiti-veringsmidler for litografiske plater. Således har disse forbindelser en struktur av mettet, ikke konjugert, ikke polar karakter, hvorfor de er lett oppløselige i vanlige organiske oppløsningsmidler, og dette til tross for at disse forbindelser har en meget høy molekylarvekt, d. v. s. noe over 1000. appears from the fact that it is able to dissolve the resins mentioned by the patent holder. The diazo oxides in the present claim, on the other hand, are soluble in simple organic solvents, which have no effect on resin substrates. There is therefore a clear difference between the invention in the German patent and in the claim. I The inventors have found that diazo oxides of aromatic sulfonamides, in which the substituent on the amido nitrogen is a high molecular weight alicyclic radical, have very advantageous properties as sensitizers for lithographic plates. Thus, these compounds have a structure of a saturated, non-conjugated, non-polar character, which is why they are easily soluble in common organic solvents, and this despite the fact that these compounds have a very high molecular weight, i.e. something over 1000.
De diazooksyder det dreier seg om kan mer spesifikt representeres ved de gene-relle formler: The diazo oxides in question can be more specifically represented by the general formulas:
hvor R' — CH2 er et alicyklisk radikal, f. eks. dehydroabietyl, dihydroabietyl, tetrahydroabietyl eller dekstropimaryl, hvor R betegner vannstoff, alkyl som f. eks. metyl, etyl eller lignende, hydroksyl som hydrok-syetyl, hydroksypropyl eller lignende, eller alkylen som f. eks. etylen; hvor R2 betegner vannstoff, alkyl eller hydroksyalkyl som nevnt ovenfor, og Z betyr de atomer som er nødvendige for å komplettere en cykloheksadienring, f. eks. 1,5-cykloheksa-dien, alkylcykloheksadien, d. v. s. metyl-cykloheksadien, etylcykloheksadien og lignende, halogencykloheksadien som f. eks. where R' — CH2 is an alicyclic radical, e.g. dehydroabietyl, dihydroabietyl, tetrahydroabietyl or dextropyramyl, where R denotes hydrogen, alkyl such as e.g. methyl, ethyl or the like, hydroxyl such as hydroxyethyl, hydroxypropyl or the like, or the alkylene such as e.g. ethylene; where R2 denotes hydrogen, alkyl or hydroxyalkyl as mentioned above, and Z denotes the atoms necessary to complete a cyclohexadiene ring, e.g. 1,5-cyclohexadiene, alkylcyclohexadiene, i.e. methylcyclohexadiene, ethylcyclohexadiene and the like, halocyclohexadiene such as e.g.
kl<p>rcykloheksadien, bromcykloheksadien og lignende, eller en di- eller polyhydro-naftalinring; hvor = N2 og = O alltid inntar nabostillinger i den samme ring, og hvor n betegner et helt tall som ikke er større enn 2, og n alltid er lik 2 hvis R er alkylen. chlorocyclohexadiene, bromocyclohexadiene and the like, or a di- or polyhydro-naphthalene ring; where = N2 and = O always occupy adjacent positions in the same ring, and where n denotes an integer not greater than 2, and n is always equal to 2 if R is alkylene.
Som eksempler på forbindelser som faller innenfor de ovennevnte formler kan nevnes følgende: 1) N-dehydroabietyl-6-diazo-5 (6) - okso-l-naftalinsulfonamid, hvis sannsynlige formel er: 2) N-dehydroabietyl-3-diazo-4-okso-1,5-sykloheksadien-l-sulfonamid med sannsynlig formel: 3) N-dehydroabietyl-N-2-hydroksyetyl- 6-diazo-5(6)-okso-l-naftalinsulfon-amid med sannsynlig formel: 4) N-dehydroabietyl-N-etyl-6-diazo-5(6)-okso-l-naftalinsulfonamid med sannsynlig formel: 5) N,N'-didehydroabietyl-N,N'-etylen- bis-(6-diazo-5(6)-okso-l-naftalin-sulfonamid) av den sannsynlige formel: 6) N-dehydroabietyl-3-diazo-6-metyl- 4-okso-l,5-sykloheksadien-l-sulfonamid av den sannsynlige formel: 7) N-dehydroabietyl-3-klor-5-diazo-6-okso-l,3-sykloheksadien-l-sulfonamid. 8) N-dehydroabietyl-3-diazo-4(3)-okso-l-naftalinsulfonamid av den sannsynlige formel: 9) N-dehydroabietyl-5,6,7,8-tetrahydro- 4-diazo-3 (4)-okso-2-naf talinsulf onamid av den sannsynlige formel: 10) N,N'-didehydroabietyl-3-diazo- 4(3)-oksy-l,6-naftalindisulfonamid av den sannsynlige formel: 11) N-dihydroabietyl-3-diazo-4-okso-1,5-sykloheksadien-l-sulfonamid. 12) N-tetrahydroabietyl-3-diazo-4-okso-1,5-sykloheksadien-1 -sulf onamid. 13) N-dekstropimaryl-3-diazo-4-oksoT 1,5-sykloheksadien-l-sulfonamid. 14) N-dihydroabietyl-6-diazo-5(6)-okso-n-naftalinsulf onamid. 15) N-tetrahydroabietyl-6-diazo-5 (6) - okso- 1-naf talinsulf onamid. 16) N-dekstropimaryl-6-diazo-5(6)-okso-1 -naf talinsulf onamid. As examples of compounds that fall within the above-mentioned formulas, the following can be mentioned: 1) N-dehydroabietyl-6-diazo-5 (6)-oxo-l-naphthalene sulfonamide, whose probable formula is: 2) N-dehydroabietyl-3-diazo- 4-oxo-1,5-cyclohexadiene-1-sulfonamide with probable formula: 3) N-dehydroabiethyl-N-2-hydroxyethyl-6-diazo-5(6)-oxo-l-naphthalene sulfonamide with probable formula: 4 ) N-dehydroabiethyl-N-ethyl-6-diazo-5(6)-oxo-1-naphthalene sulfonamide of probable formula: 5) N,N'-didehydroabiethyl-N,N'-ethylene-bis-(6-diazo- 5(6)-oxo-1-naphthalene-sulfonamide) of the probable formula: 6) N-dehydroabiethyl-3-diazo-6-methyl-4-oxo-1,5-cyclohexadiene-1-sulfonamide of the probable formula: 7) N-dehydroabiethyl-3-chloro-5-diazo-6-oxo-1,3-cyclohexadiene-1-sulfonamide. 8) N-dehydroabiethyl-3-diazo-4(3)-oxo-1-naphthalene sulfonamide of the probable formula: 9) N-dehydroabiethyl-5,6,7,8-tetrahydro-4-diazo-3 (4)- oxo-2-naphthalene sulfonamide of the probable formula: 10) N,N'-didehydroabiethyl-3-diazo-4(3)-oxy-1,6-naphthalene disulfonamide of the probable formula: 11) N-dihydroabiethyl-3- diazo-4-oxo-1,5-cyclohexadiene-1-sulfonamide. 12) N-tetrahydroabiethyl-3-diazo-4-oxo-1,5-cyclohexadiene-1-sulfonamide. 13) N-dextropimaryl-3-diazo-4-oxoT 1,5-cyclohexadiene-1-sulfonamide. 14) N-dihydroabiethyl-6-diazo-5(6)-oxo-n-naphthalene sulfonamide. 15) N-tetrahydroabiethyl-6-diazo-5 (6)-oxo-1-naphthalene sulfonamide. 16) N-dextropimaryl-6-diazo-5(6)-oxo-1-naphthalene sulfonamide.
Mange av de ovenfor nevnte forbindelser kan fremstilles ved å la et passende diazooksyd av et aromatisk sulfonylklorid reagere med et egnet alicyklisk amin. Reaksjonsmediumet kan være en hvilken som helst væske som er et tilstrekkelig godt oppløsningsmiddel for utgangsmaterialene til å muliggjøre reaksjon mellom disse og som er tilstrekkelig inert i forhold til sulfonylklorid til å hindre gjensidig reaksjon under de herskende forhold. Som oppløs-ningsmidler foretrekkes isopropylalkohol og dioksan. Many of the above compounds can be prepared by reacting a suitable diazo oxide of an aromatic sulphonyl chloride with a suitable alicyclic amine. The reaction medium can be any liquid which is a sufficiently good solvent for the starting materials to enable reaction between them and which is sufficiently inert in relation to sulfonyl chloride to prevent mutual reaction under the prevailing conditions. The preferred solvents are isopropyl alcohol and dioxane.
De alicykliske aminer som kan anvendes er dehydroabietylamin-, dihydro-abietylamin, tetrahydroabietylamin, dekstropimarylamin, 2-dehydroabietyl-aminoetanol, N-metyldehydroabietylamin, N-etyldehydroabietylamin, N,N'-etylen-didehydroabietylamin og liknende. Disse aminer kan skaffes som sådanne eller i blanding med hverandre, og det kan anvendes såvel de enkelte aminer som blan-dinger av dem. Spesielt fordelaktig er det i handelen forekommende prdoukt «Rosin Amine D» som inneholder ca. 90 pst. dehydroabietylamin. The alicyclic amines which can be used are dehydroabiethylamine, dihydroabiethylamine, tetrahydroabiethylamine, dextropyramylamine, 2-dehydroabiethylaminoethanol, N-methyldehydroabiethylamine, N-ethyldehydroabiethylamine, N,N'-ethylene-didehydroabiethylamine and the like. These amines can be obtained as such or in a mixture with each other, and both the individual amines and mixtures of them can be used. Particularly advantageous is the commercially available product "Rosin Amine D", which contains approx. 90 percent dehydroabiethylamine.
Blant sulfonylklorider der kan anvendes som sådanne er 6-diazo-5(6)-okso-l-naftalensulfonylklorid, som har den føl-gende formel: Among sulfonyl chlorides that can be used as such are 6-diazo-5(6)-oxo-1-naphthalenesulfonyl chloride, which has the following formula:
3 -diazo-4 (3) -okso-1 -naf talinsulf onyl-klorid med følgende formel 3-diazo-4-okso-l,5-sykloheksadien-l-sulfonylklorid med den følgende formel: 3-diazo-4 (3)-oxo-1-naphthalene sulfonyl chloride of the following formula 3-diazo-4-oxo-1,5-cyclohexadiene-1-sulfonyl chloride of the following formula:
Forbindelse kan også som sulfonyl-halvdel inneholde 5,6,7,8-tetrahydro-4-diazo-3- (4) -okso-2-naftalinsulfonyl av formelen: Compound can also contain as sulfonyl moiety 5,6,7,8-tetrahydro-4-diazo-3-(4)-oxo-2-naphthalenesulfonyl of the formula:
3-diazo-4(3)-okso-l,6-naftalindisulfonyl av formelen: 3-klor-5-diazo-6-okso-l,3-sykloheksadien-1-sulfonyl av formelen: 3-diazo-5-metyl-4-okso-l,5-sykloheksa-diensulfonyl av formelen: 3-diazo-6-metyl-4-okso-l,5-sykloheksa-diensulfonyl av formelen: 3-diazo-4(3)-oxo-1,6-naphthalenedisulfonyl of the formula: 3-chloro-5-diazo-6-oxo-1,3-cyclohexadiene-1-sulfonyl of the formula: 3-diazo-5-methyl -4-oxo-1,5-cyclohexadiensulfonyl of the formula: 3-diazo-6-methyl-4-oxo-1,5-cyclohexadiensulfonyl of the formula:
og liknende. | and similar. |
Disse halvdeler kan innføres i det alicykliske amin eksempelvis på den måte som er generelt beskrevet i de tyske patenter nr. 888 204 og 871 668. Hvis det aromatiske sulfonylradikal er monocyklisk kan således den tilsvarende aminohydrok-sulfonsyre omdannes til et benzoksalon-sulfonylklorid, som igjen kan bringes til å reagere med det ønskede alicykliske amin. Benzoksalonringen kan så spaltes ved opp-hetning med alkali, og det resulterende aminohydroksysulfonamid kan omdannes til sammes hydroklorid. Hydrokloridet kan deretter, eventuelt uten først å isoleres, diazoteres og gi det ønskede diazooksyd. These moieties can be introduced into the alicyclic amine, for example, in the manner generally described in German patents no. 888,204 and 871,668. If the aromatic sulfonyl radical is monocyclic, the corresponding aminohydrosulfonic acid can thus be converted into a benzoxalone sulfonyl chloride, which in turn can be reacted with the desired alicyclic amine. The benzoxalone ring can then be cleaved by heating with alkali, and the resulting aminohydroxysulfonamide can be converted to the same hydrochloride. The hydrochloride can then, possibly without first being isolated, be diazotized and give the desired diazo oxide.
I det tilfelle at en halvdel som inneholder to sulfonylgrupper skal innføres, oppnås dette på den måte som er beskrevet i eks. 10 i tysk patent nr. 871 668. In the event that a half containing two sulfonyl groups is to be introduced, this is achieved in the manner described in ex. 10 of German patent no. 871 668.
Oppfinnelsen vil bli illustrert videre ved de følgende eksempler: Eksempel 1: N-dehydroabietyl-6-diazo-5(6)-okso-l- naftalinsulfonamid. The invention will be further illustrated by the following examples: Example 1: N-dehydroabiethyl-6-diazo-5(6)-oxo-1- naphthalene sulfonamide.
Til en omrørt oppløsning av 28,5 g «Rosin Amine D» (laget av Hercules Powder Company) i 160 ml dioksan settes det 28,5 g 6-diazo-5(6)-okso-l-naftalin-sulfonylklorid. Temperaturen steg til 42° C, klor-idet ble oppløst og i løpet av ca. 5 minutter ble det tilsatt 40 ml av en 3N natrium-karbonatoppløsning. Under fortsatt om-røring ble det langsomt tilsatt 300 ml isvann, sammen med podningskrystaller fra et tidligere fremstilt preparat. Den olje som først skilte seg ut stivnet langsomt til små kuler. Etter to timers forløp ble det gule produkt oppsamlet, vasket og tørket under nedsatt trykk. Utbyttet var praktisk talt kvantitativt. Rensing kunne skje ved at stoffet ble oppløst i alkoholisk natrium-hydroksyd, filtrering og felning med vandig ediksyre (sm.p. 115—36° C spaltning) eller enklere ved omkrystallisering fra al-koholer, etylacetat, aceton eller vandig dioksan. To a stirred solution of 28.5 g of "Rosin Amine D" (made by Hercules Powder Company) in 160 ml of dioxane is added 28.5 g of 6-diazo-5(6)-oxo-1-naphthalene-sulfonyl chloride. The temperature rose to 42° C, the chloride was dissolved and within approx. After 5 minutes, 40 ml of a 3N sodium carbonate solution was added. With continued stirring, 300 ml of ice water was slowly added, together with seed crystals from a previously prepared preparation. The oil that first separated slowly solidified into small globules. After two hours, the yellow product was collected, washed and dried under reduced pressure. The yield was practically quantitative. Purification could take place by dissolving the substance in alcoholic sodium hydroxide, filtering and precipitation with aqueous acetic acid (m.p. 115-36° C decomposition) or more simply by recrystallization from alcohols, ethyl acetate, acetone or aqueous dioxane.
Det i eks. III, IV og V anvendte sulfonylklorid ble fremstilt etter en metode som var lik den som er beskrevet i tysk patent nr. 865 410, side 2, linje 98—103. That in e.g. The sulfonyl chloride used in III, IV and V was prepared by a method similar to that described in German Patent No. 865,410, page 2, lines 98-103.
Eksempel 2: N-dehydroabietyl-3-diazo-4-okso-l,5- sykloheksadien-l-sulfonamid. Example 2: N-dehydroabiethyl-3-diazo-4-oxo-1,5- cyclohexadiene-1-sulfonamide.
En oppløsning av 8,6 g «Rosin amine D» i 50 ml dioksan ble behandlet med 6,6 g A solution of 8.6 g of "Rosin amine D" in 50 ml of dioxane was treated with 6.6 g
3-diazo-4-okso-l,5-sykloheksadien-l- 3-diazo-4-oxo-1,5-cyclohexadiene-1-
sulfonylklorid (sm.p. 111—2° C med spaltn. sulfonyl chloride (m.p. 111-2° C with cleavage
(korrigert) hvoretter det ble tilsatt 12 ml vandig natriumkarbonat av 3N. Reaksjons- (corrected) after which 12 ml of aqueous sodium carbonate of 3N was added. reaction
blandingen, som spontant ble oppvarmet til 40—50° C ble omrørt i 1—i<y>2 time, og ble deretter langsomt tilsatt 100 ml koldt vann. Den olje som falt ut etter kjøling natten over ble skilt fra og tørket i vakuum. the mixture, which was spontaneously heated to 40—50° C., was stirred for 1—i<y>2 hours, and then 100 ml of cold water was slowly added. The oil that precipitated after cooling overnight was separated and dried in vacuum.
Etter denne behandling var produktet et After this treatment, the product was a
mørkt, skjørt, fotofølsomt stoff. dark, fragile, photosensitive fabric.
Det ovenfor nevnte anvendte sulfonyl- The above-mentioned used sulfonyl-
klorid 'var fremstilt på den måte som er beskrevet i tysk patent nr. 888 204, side 10, chloride' was prepared in the manner described in German patent no. 888 204, page 10,
linje 23—27. lines 23-27.
Eksempel 3: N-dehydroabietyl-N-2-hydroksyetyl-6-diazo-5(6),-okso-l-naftalensulf onamid. Example 3: N-dehydroabiethyl-N-2-hydroxyethyl-6-diazo-5(6),-oxo-1-naphthalenesulfonamide.
Reaksjon mellom 33 g 2-dehydroabietyl-aminoetanol (Hercules «Polyrad 0100») Reaction between 33 g of 2-dehydroabiethyl-aminoethanol (Hercules "Polyrad 0100")
og 28,5 g 6-diazo-5(6)-okso-l-naftalin- and 28.5 g of 6-diazo-5(6)-oxo-1-naphthalene-
sulfonylklorid i 160 ml dioksan ble utført på den i eks. I beskrevne måte. Det er- sulfonyl chloride in 160 ml of dioxane was carried out on that in ex. In the described manner. It is-
holdte gule produkt var meget fotofølsomt. remained yellow product was very photosensitive.
Det smeltet under ' spaltning, ved ca. 95— It melted during 'fission, at approx. 95—
105° C. 105°C.
Eksempel 4: N,N'-didehydroabietyl-N,N'etylenbis (6-di azo-5(6)-okso-l-naftalinsulfonamid). Example 4: N,N'-didehydroabiethyl-N,N'ethylenebis (6-di azo-5(6)-oxo-1-naphthalene sulfonamide).
Reaksjonen mellom 15 g N,N'-etylen-didehydroabietylamin i 80 ml dioksan, 14,2 g 6-diazo-5(6)-okso-l-naftalin-sulfonylklo- The reaction between 15 g of N,N'-ethylene-didehydroabiethylamine in 80 ml of dioxane, 14.2 g of 6-diazo-5(6)-oxo-1-naphthalene-sulfonychloro-
rid i 20 ml natriumkarbonat av 3N ble fore- rid in 20 ml sodium carbonate of 3N was pre-
tatt på den i eks. 1 beskrevne måte. Pro- taken on it in ex. 1 described way. Pro-
duktet, en mørkfarget tjære som krystalli- ducted, a dark-colored tar that crystallizes
serte langsomt, smeltet under spaltning ved ca. 105° C. serted slowly, melted during cleavage at approx. 105°C.
Etylendiamin-mellomproduktet ble The ethylenediamine intermediate was
fremstilt ved å la de teoretiske mengder av «Rosin Amine D) og etylenbromid reagere ved 140° i xylol, fulgt av behandling med natriumhydroksydoppløsning for å fri ba- prepared by allowing the theoretical quantities of "Rosin Amine D) and ethylene bromide to react at 140° in xylol, followed by treatment with sodium hydroxide solution to free ba-
sen fra dihydrobromidet. late from the dihydrobromide.
Eksempel 5: N-dehydroabietyl-6-diazo-5(6)-okso-l- naf talinsulf onamid. Example 5: N-dehydroabiethyl-6-diazo-5(6)-oxo-1- naphthalene sulfonamide.
Fremgangsmåten var den samme som i The procedure was the same as in
eks. I, med den unntakelse at det i stedet for dioksan ble anvendt 200 ml isopropanyl- e.g. I, with the exception that instead of dioxane, 200 ml of isopropanyl
alkohol og at mengden av isvann ble ned- alcohol and that the amount of ice water was reduced
satt fra 300 ml til 100 ml. Ved å bruke iso- set from 300 ml to 100 ml. By using iso-
propylalkohol unngår man den første at- propyl alcohol, one avoids the first at-
skillelse av produktet i form av en olje og det fås et findelt gult fast stoff, som er lett å tørke, ikke krever noen rensing og som regel smelter ved over 150° C. separation of the product in the form of an oil and a finely divided yellow solid is obtained, which is easy to dry, does not require any purification and usually melts at over 150° C.
Den beskrevne oppfinnelse kan modi- The described invention can modi-
fiseres på forskjellige måter. Det er f. eks. are faced in different ways. It is e.g.
klart, at hvilke, som helst av de angitte sulfonylklorider kan benyttes i forbindelse med hvilke som helst av de angitte alicyk- clear, that any of the specified sulfonyl chlorides can be used in connection with any of the specified alicyclic
liske aminer. Enn videre kan hvilken som helst av de alicykliske aminer bli forbun- lish amines. Still further, any of the alicyclic amines can be linked
det med de nevnte sulfonylhalvdeler ved i og for seg kjente arbeidsmåter. that with the aforementioned sulfonyl moieties by working methods known per se.
Claims (5)
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NO117673B true NO117673B (en) | 1969-09-08 |
Family
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NO147520A NO117673B (en) | 1962-02-14 | 1963-02-13 |
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NO (1) | NO117673B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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SE333299B (en) * | 1967-11-10 | 1971-03-08 | Sunds Ab | PROCEDURE AND DEVICE FOR BLEACHING PREFERRED CELLULOSA MASS WITH GASY BLEACHING |
US3884752A (en) * | 1973-09-17 | 1975-05-20 | Int Paper Co | Single vessel wood pulp bleaching with chlorine dioxide followed by sodium hypochlorite or alkaline extraction |
CA1151363A (en) * | 1979-04-17 | 1983-08-09 | Henri Lemoyne | Process for the delignification of unbleached chemical pulp |
FR2479295A2 (en) * | 1980-03-31 | 1981-10-02 | Europeen Cellulose | Delignification of chemical pulp - by peroxide oxidation in alkaline medium followed by mechanical pressing |
NO164310C (en) * | 1984-03-05 | 1990-09-19 | Kamyr Inc | PROCEDURE FOR THE TREATMENT OF A MECHANICAL MASS WITH HYDROSULPHITE-BLEACH CHEMICALS. |
US5589036A (en) * | 1992-05-18 | 1996-12-31 | Champion International Corporation | Controlling pulp flow in an upflow pulp treatment tower |
US5372679A (en) * | 1992-06-08 | 1994-12-13 | Air Products And Chemicals, Inc. | Reactor system for treating cellulosic pulp at a constant upward flow velocity |
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US1643566A (en) * | 1925-10-16 | 1927-09-27 | Thorne Carl Busch | Process for bleaching and the like purposes |
US2089992A (en) * | 1932-03-14 | 1937-08-17 | Int Paper Co | Continuous bleaching process and apparatus |
US2474862A (en) * | 1942-10-15 | 1949-07-05 | Kamyr Ab | Process and apparatus for continuous digestion of fibrous materials |
US2662821A (en) * | 1949-05-03 | 1953-12-15 | Celotex Corp | Fiber preparation device |
US2711359A (en) * | 1953-10-19 | 1955-06-21 | Kamyr Ab | Bleaching plant and method of bleaching cellulose pulp |
US2769710A (en) * | 1954-01-12 | 1956-11-06 | Cellulose Dev Corp Ltd | Process for the continuous treatment of vegetable fibers |
DE1034968B (en) * | 1956-01-11 | 1958-07-24 | Hans Werner Meyer | Continuous process for the chemical breakdown of cellulosic fibers into cellulose or semi-cellulose and device for its implementation |
FR1229425A (en) * | 1958-07-09 | 1960-09-07 | Kamyr Ab | Process and installation for the continuous cooking of cellulose |
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1963
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