CH618187A5 - - Google Patents

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Info

Publication number: CH618187A5
Authority: CH; Switzerland
Prior art keywords: cellulose; acid; ch2ch2; mol; formula
Prior art date: 1974-08-05

Application number

CH1002875A

Other languages

German (de)

English (en)

Inventor

Karl Heinrich Prof Dr Lieser

Peter Dr Burba

Original Assignee

Riedel De Haen Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-08-05

Filing date

1975-07-31

Publication date

1980-07-15

1974-08-05 Priority claimed from DE2437594A external-priority patent/DE2437594A1/de

1975-07-31 Application filed by Riedel De Haen Ag filed Critical Riedel De Haen Ag

1980-07-15 Publication of CH618187A5 publication Critical patent/CH618187A5/de

Links

229920002678 cellulose Polymers 0.000 claims description 63
239000001913 cellulose Substances 0.000 claims description 62
235000010980 cellulose Nutrition 0.000 claims description 62
150000002500 ions Chemical class 0.000 claims description 29
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 19
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 11
229960004889 salicylic acid Drugs 0.000 claims description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
239000005725 8-Hydroxyquinoline Substances 0.000 claims description 8
229960003540 oxyquinoline Drugs 0.000 claims description 8
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical class OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 claims description 5
229920000168 Microcrystalline cellulose Polymers 0.000 claims description 5
239000008108 microcrystalline cellulose Substances 0.000 claims description 5
235000019813 microcrystalline cellulose Nutrition 0.000 claims description 5
229940016286 microcrystalline cellulose Drugs 0.000 claims description 5
HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 claims description 4
YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 claims description 3
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical class NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 claims description 3
235000007708 morin Nutrition 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
JKYKXTRKURYNGW-UHFFFAOYSA-N 3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(O)C(S(O)(=O)=O)=C2 JKYKXTRKURYNGW-UHFFFAOYSA-N 0.000 claims 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
239000002904 solvent Substances 0.000 claims 2
229960005181 morphine Drugs 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
-1 aminophenyl Chemical group 0.000 description 8
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
125000000524 functional group Chemical group 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 6
239000003513 alkali Substances 0.000 description 5
238000006193 diazotization reaction Methods 0.000 description 5
238000004043 dyeing Methods 0.000 description 5
239000000843 powder Substances 0.000 description 5
XJWCMSMUESXHFG-UHFFFAOYSA-N 2-hydroxy-5-(2-sulfooxyethylsulfonyl)benzoic acid Chemical compound OC(=O)C1=CC(S(=O)(=O)CCOS(O)(=O)=O)=CC=C1O XJWCMSMUESXHFG-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
QTCQXOXUIPNFNH-UHFFFAOYSA-N 2-hydroxy-5-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC(S)=CC=C1O QTCQXOXUIPNFNH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
ISWQCIVKKSOKNN-UHFFFAOYSA-L Tiron Chemical compound [Na+].[Na+].OC1=CC(S([O-])(=O)=O)=CC(S([O-])(=O)=O)=C1O ISWQCIVKKSOKNN-UHFFFAOYSA-L 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical group [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
229910001410 inorganic ion Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000004448 titration Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
RHFLLWVVJXIKDZ-UHFFFAOYSA-N 2-hydroxy-5-(2-hydroxyethylsulfanyl)benzoic acid Chemical compound OCCSC1=CC=C(O)C(C(O)=O)=C1 RHFLLWVVJXIKDZ-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
229920001425 Diethylaminoethyl cellulose Polymers 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
FSVHTWITPYPMHK-UHFFFAOYSA-L barium(2+);2-carboxyphenolate Chemical compound [Ba+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O FSVHTWITPYPMHK-UHFFFAOYSA-L 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000010559 graft polymerization reaction Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
HKPHUICWPSKEMR-UHFFFAOYSA-M sodium;chloromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCl HKPHUICWPSKEMR-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000000954 titration curve Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/22—Cellulose or wood; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Biochemistry (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Wood Science & Technology (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

CH1002875A 1974-08-05 1975-07-31 CH618187A5 (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2437594A DE2437594A1 (de)	1974-08-05	1974-08-05	Ionenaustauscher auf cellulosebasis und verfahren zu seiner herstellung

Publications (1)

Publication Number	Publication Date
CH618187A5 true CH618187A5 (fi)	1980-07-15

Family

ID=5922440

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1002875A CH618187A5 (fi)	1974-08-05	1975-07-31

Country Status (4)

Country	Link
US (1)	US4022964A (fi)
CH (1)	CH618187A5 (fi)
FR (1)	FR2281378A1 (fi)
GB (1)	GB1470492A (fi)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4109080A (en) *	1976-07-01	1978-08-22	Riedel-De Haen Aktiengesellschaft	Ion exchange compounds on cellulose basis and process for the manufacture thereof
US4401743A (en) *	1980-04-30	1983-08-30	Minnesota Mining And Manufacturing Company	Aqueous developable photosensitive composition and printing plate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2539704A (en) *	1948-07-07	1951-01-30	Us Rubber Co	Treatment of hydroxylated polymers
US3720500A (en) *	1959-12-31	1973-03-13	Deering Milliken Res Corp	Textile materials and processes for making the same
US3414367A (en) *	1963-11-06	1968-12-03	Agriculture Usa	Process for making n-substituted aminoethylsulfonylethyl ethers of cellulose

1975
- 1975-07-30 US US05/600,298 patent/US4022964A/en not_active Expired - Lifetime
- 1975-07-31 CH CH1002875A patent/CH618187A5/de not_active IP Right Cessation
- 1975-08-05 GB GB3272875A patent/GB1470492A/en not_active Expired
- 1975-08-05 FR FR7524338A patent/FR2281378A1/fr active Granted

Also Published As

Publication number	Publication date
FR2281378B1 (fi)	1979-01-05
FR2281378A1 (fr)	1976-03-05
US4022964A (en)	1977-05-10
GB1470492A (en)	1977-04-14

Publication	Publication Date	Title
DE2504031C2 (fi)	1988-06-30
EP0214543A2 (de)	1987-03-18	Verfahren zur Herstellung von 1-Aminoaphthalin-2,4,7-trisulfonsäure und 1-Aminonaphthalin-7-sulfonsäure
DE2229064A1 (de)	1973-12-20	Verfahren zur herstellung von fruktose
CH618187A5 (fi)	1980-07-15
DE1695071B2 (de)	1976-06-24	3-hydroxy-2-imino-1 (2h)-pyridinsulfonsaeure-monohydrat
EP0980711B1 (de)	2004-06-30	Verfahren zur Herstellung von Selektivaustauschern
DE2437594A1 (de)	1976-02-26	Ionenaustauscher auf cellulosebasis und verfahren zu seiner herstellung
EP0012260B1 (de)	1981-09-16	Neue sulfierungsprodukte des Naphthalins, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0044029A1 (de)	1982-01-20	Verfahren zur Herstellung von Hydroxylammoniumperchlorat
AT397504B (de)	1994-04-25	Diosminderivat und verfahren zu dessen herstellung
US3047556A (en)	1962-07-31	Process for the production of polyvinyl hydrogen sulphates
EP0037510B1 (de)	1983-03-09	Verfahren zur Herstellung von 1-Naphthylamin-4,6-disulfonsäure und 1-Naphthylamin-2,4,6-trisulfonsäure
DE3390129C2 (de)	1987-09-10	Verfahren zur Herstellung von kristallinem Dl-Cystein
CH625786A5 (en)	1981-10-15	Process for preparing 1-amino-2-sulphophenyl 5-beta-sulphatoethyl sulphone and 5-vinyl sulphone and alkali and alkaline earth metal salts thereof
EP0038999B1 (de)	1983-07-13	Verfahren zur Herstellung von 2-Chlor-5-formylbenzolsulfonsäure
DE3118903A1 (de)	1982-12-02	Verfahren zur herstellung von 1-benzoylamino-8-hydroxy-naphthalin-4.6.-disulfonsaeure (benzoyl-k-saeure)
DE2830060C2 (de)	1986-08-28	Schwefelsäurehalbester des 4-Hydroxybenzylcyamids und Verfahren zu deren Herstellung
DE1793428A1 (de)	1972-03-02	Neue Thiosulfatverbindungen und Verfahren zu deren Herstellung
AT357982B (de)	1980-08-11	Verfahren zur herstellung von neuen vernetzten hydrophilen polymer-gelen
DE1618015C3 (de)	1976-05-26	Verfahren zur Sulfonierung von mehrkernigen aromatischen oder heterocyclischen Aminen sowie von Aminoantrachinonen oder metallhaltigen Amino-azo-Farbstoffen der Naphthalinreihe und neue so erhaltene Sulfonlerungsprodukte
AT357981B (de)	1980-08-11	Verfahren zur herstellung von neuen vernetzten hydrophilen affinitaetschromatographie-gelen
DE1086434B (de)	1960-08-04	Verfahren zur Herstellung von Polyvinylhydrogensulfat
DE1695071C3 (de)	1977-02-10	3-Hydroxy-2-imino-1 (2H) -pyridinsulfonsäure-monohydrat
DE2058776A1 (de)	1972-06-08	Verfahren zur Herstellung von Vinylsulfonaten und Vinylsulfonsaeure aus Carbylsulfat
JPS6141358B2 (fi)	1986-09-13

Legal Events

Date	Code	Title	Description
1986-03-27	PL	Patent ceased
2024-10-31	PL	Patent ceased