NO319310B1 - Stabiliserte losninger av hydroksylamin - Google Patents

Stabiliserte losninger av hydroksylamin Download PDF

Info

Publication number: NO319310B1
Authority: NO; Norway
Prior art keywords: hydroxylamine; stabilizer; compound; formula; stabilized
Prior art date: 1995-12-20

Application number

NO19982848A

Other languages

English (en)

Norwegian (no)

Other versions

NO982848D0 (no

NO982848L (no

Inventor

Bernd Leutner

Hans-Michael Schneider

Original Assignee

Basf 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.)

1995-12-20

Filing date

1998-06-19

Publication date

2005-07-11

1998-06-19 Application filed by Basf Ag filed Critical Basf Ag

1998-06-19 Publication of NO982848D0 publication Critical patent/NO982848D0/no

1998-08-19 Publication of NO982848L publication Critical patent/NO982848L/no

2005-07-11 Publication of NO319310B1 publication Critical patent/NO319310B1/no

Links

AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title claims abstract description 61
150000001875 compounds Chemical class 0.000 claims abstract description 26
239000003381 stabilizer Substances 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
229920002873 Polyethylenimine Polymers 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
125000002993 cycloalkylene group Chemical group 0.000 claims description 9
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
230000000087 stabilizing effect Effects 0.000 claims description 7
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
229920000333 poly(propyleneimine) Polymers 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000000732 arylene group Chemical group 0.000 claims description 5
150000002443 hydroxylamines Chemical class 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000004450 alkenylene group Chemical group 0.000 claims description 3
125000005724 cycloalkenylene group Chemical group 0.000 claims description 3
125000004956 cyclohexylene group Chemical group 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000004419 alkynylene group Chemical group 0.000 claims description 2
IFQUWYZCAGRUJN-UHFFFAOYSA-N ethylenediaminediacetic acid Chemical compound OC(=O)CNCCNCC(O)=O IFQUWYZCAGRUJN-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 claims description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
FCKYPQBAHLOOJQ-NXEZZACHSA-N 2-[[(1r,2r)-2-[bis(carboxymethyl)amino]cyclohexyl]-(carboxymethyl)amino]acetic acid Chemical group OC(=O)CN(CC(O)=O)[C@@H]1CCCC[C@H]1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-NXEZZACHSA-N 0.000 claims 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
239000000243 solution Substances 0.000 description 33
125000004432 carbon atom Chemical group C* 0.000 description 9
238000006467 substitution reaction Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000002585 base Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
-1 mercaptoalkanols Chemical class 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000012458 free base Substances 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 2
VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 2
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
238000004448 titration Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical class SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 description 1
LVPSKWMJXFMIHR-UHFFFAOYSA-N 1-hydroxy-1-phenylthiourea Chemical compound NC(=S)N(O)C1=CC=CC=C1 LVPSKWMJXFMIHR-UHFFFAOYSA-N 0.000 description 1
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
CPPWUTNKPOSOOF-UHFFFAOYSA-N 3-ethenyl-5-ethyl-1,3-oxazolidin-2-one Chemical compound CCC1CN(C=C)C(=O)O1 CPPWUTNKPOSOOF-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
229940058934 aminoquinoline antimalarials Drugs 0.000 description 1
150000005010 aminoquinolines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000004410 anthocyanin Substances 0.000 description 1
229930002877 anthocyanin Natural products 0.000 description 1
235000010208 anthocyanin Nutrition 0.000 description 1
150000004636 anthocyanins Chemical class 0.000 description 1
229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
ITZXULOAYIAYNU-UHFFFAOYSA-N cerium(4+) Chemical class [Ce+4] ITZXULOAYIAYNU-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
229920003020 cross-linked polyethylene Polymers 0.000 description 1
239000004703 cross-linked polyethylene Substances 0.000 description 1
125000005725 cyclohexenylene group Chemical group 0.000 description 1
125000004979 cyclopentylene group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
238000007046 ethoxylation reaction Methods 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical class C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 description 1
229930003944 flavone Natural products 0.000 description 1
150000002213 flavones Chemical class 0.000 description 1
235000011949 flavones Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000004338 hydroxy anthraquinones Chemical class 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
XBUFCZMOAHHGMX-UHFFFAOYSA-N hydroxylamine;phosphoric acid Chemical compound ON.ON.ON.OP(O)(O)=O XBUFCZMOAHHGMX-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000005041 phenanthrolines Chemical class 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
150000008442 polyphenolic compounds Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
HREHOXSRYOZKNT-UHFFFAOYSA-N quinolin-2-ylmethanol Chemical class C1=CC=CC2=NC(CO)=CC=C21 HREHOXSRYOZKNT-UHFFFAOYSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/14—Hydroxylamine; Salts thereof
- C01B21/149—Stabilisation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Detergent Compositions (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Compositions Of Macromolecular Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19982848A 1995-12-20 1998-06-19 Stabiliserte losninger av hydroksylamin NO319310B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19547759A DE19547759A1 (de)	1995-12-20	1995-12-20	Stabilisierte Hydroxylaminlösungen
US08/684,910 US5783161A (en)	1995-12-20	1996-07-25	Stabilized hyroxylamine solutions
PCT/EP1996/005771 WO1997022549A1 (de)	1995-12-20	1996-12-20	Stabilisierte hydroxylaminlösungen

Publications (3)

Publication Number	Publication Date
NO982848D0 NO982848D0 (no)	1998-06-19
NO982848L NO982848L (no)	1998-08-19
NO319310B1 true NO319310B1 (no)	2005-07-11

Family

ID=26021482

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19982848A NO319310B1 (no)	1995-12-20	1998-06-19	Stabiliserte losninger av hydroksylamin

Country Status (18)

Country	Link
US (1)	US5783161A (es)
EP (1)	EP0868397B1 (es)
JP (1)	JP4204068B2 (es)
CN (2)	CN1295144C (es)
AT (1)	ATE191435T1 (es)
AU (1)	AU706540B2 (es)
BR (1)	BR9612078A (es)
CA (1)	CA2239805C (es)
DE (2)	DE19547759A1 (es)
DK (1)	DK0868397T3 (es)
ES (1)	ES2145510T3 (es)
GR (1)	GR3033334T3 (es)
HR (1)	HRP960602B1 (es)
IL (1)	IL124738A (es)
NO (1)	NO319310B1 (es)
PT (1)	PT868397E (es)
TR (1)	TR199801162T2 (es)
WO (1)	WO1997022549A1 (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5906805A (en) *	1997-04-30	1999-05-25	Alliedsignal Inc.	Stabilized hydroxylamine solutions
DE10008080A1 (de) *	2000-02-22	2001-08-23	Basf Ag	Stabilisator für Hydroxylaminlösungen
JP4582602B2 (ja) *	2000-03-24	2010-11-17	ビーエーエスエフソシエタス・ヨーロピア	ヒドロキシルアミン水溶液およびその製造方法
KR100887695B1 (ko)	2001-10-03	2009-03-11	바스프 에스이	안정화된 히드록실아민 용액 및 히드록실아민 용액의 안정화 방법
US7396519B2 (en) *	2004-01-26	2008-07-08	San Fu Chemical Company, Ltd.	Preparation of a high purity and high concentration hydroxylamine free base
CN100504419C (zh) *	2005-06-20	2009-06-24	中国科学院半导体研究所	一种热光开关阵列光电特性测试装置及方法
JP2007119277A (ja) *	2005-10-26	2007-05-17	Showa Denko Kk	ヒドロキシルアミンの安定化剤、安定化方法および安定化されたヒドロキシルアミン溶液

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3145082A (en) *	1959-12-07	1964-08-18	Dow Chemical Co	Stabilized hydroxylamine and its method of preparation
US3462269A (en) *	1966-08-01	1969-08-19	Minnesota Mining & Mfg	Stabilized color developing solution containing diethylenetriamine pentaacetic acid
US3544270A (en) *	1968-08-13	1970-12-01	Sinclair Oil Corp	Aqueous hydroxylamine solutions stabilized with hydroxyurea or hydroxythiourea derivatives
DE2246610C3 (de) *	1972-09-22	1980-01-03	Agfa-Gevaert Ag, 5090 Leverkusen	Photographischer Farbentwickler
EP0093536B1 (en) *	1982-04-29	1986-10-08	EASTMAN KODAK COMPANY (a New Jersey corporation)	Stabilised photographic color developer compositions and processes
IT1255179B (it) *	1992-06-26	1995-10-20	Enzo Cereda	Azaciclo e azabiciclo alchiliden idrossilamine

1995
- 1995-12-20 DE DE19547759A patent/DE19547759A1/de not_active Withdrawn
1996
- 1996-07-25 US US08/684,910 patent/US5783161A/en not_active Expired - Lifetime
- 1996-12-19 HR HR960602A patent/HRP960602B1/xx not_active IP Right Cessation
- 1996-12-20 IL IL12473896A patent/IL124738A/xx not_active IP Right Cessation
- 1996-12-20 CA CA002239805A patent/CA2239805C/en not_active Expired - Lifetime
- 1996-12-20 WO PCT/EP1996/005771 patent/WO1997022549A1/de active IP Right Grant
- 1996-12-20 CN CNB961800704A patent/CN1295144C/zh not_active Expired - Lifetime
- 1996-12-20 EP EP96944046A patent/EP0868397B1/de not_active Expired - Lifetime
- 1996-12-20 DE DE59604916T patent/DE59604916D1/de not_active Expired - Lifetime
- 1996-12-20 TR TR1998/01162T patent/TR199801162T2/xx unknown
- 1996-12-20 AU AU13774/97A patent/AU706540B2/en not_active Expired
- 1996-12-20 ES ES96944046T patent/ES2145510T3/es not_active Expired - Lifetime
- 1996-12-20 CN CN2006101628668A patent/CN1962417B/zh not_active Expired - Lifetime
- 1996-12-20 PT PT96944046T patent/PT868397E/pt unknown
- 1996-12-20 JP JP52252297A patent/JP4204068B2/ja not_active Expired - Lifetime
- 1996-12-20 AT AT96944046T patent/ATE191435T1/de active
- 1996-12-20 DK DK96944046T patent/DK0868397T3/da active
- 1996-12-20 BR BR9612078A patent/BR9612078A/pt not_active IP Right Cessation
1998
- 1998-06-19 NO NO19982848A patent/NO319310B1/no not_active IP Right Cessation
2000
- 2000-04-26 GR GR20000401018T patent/GR3033334T3/el unknown

Also Published As

Publication number	Publication date
BR9612078A (pt)	1999-02-17
CN1962417A (zh)	2007-05-16
NO982848D0 (no)	1998-06-19
ES2145510T3 (es)	2000-07-01
CN1209107A (zh)	1999-02-24
WO1997022549A1 (de)	1997-06-26
JP2000502035A (ja)	2000-02-22
HRP960602B1 (en)	2001-08-31
DE19547759A1 (de)	1997-06-26
US5783161A (en)	1998-07-21
TR199801162T2 (xx)	1998-08-21
IL124738A0 (en)	1999-01-26
AU1377497A (en)	1997-07-14
PT868397E (pt)	2000-09-29
HRP960602A2 (en)	1998-02-28
ATE191435T1 (de)	2000-04-15
CA2239805C (en)	2006-12-19
GR3033334T3 (en)	2000-09-29
EP0868397A1 (de)	1998-10-07
DK0868397T3 (da)	2000-07-17
DE59604916D1 (de)	2000-05-11
CN1962417B (zh)	2010-05-19
CN1295144C (zh)	2007-01-17
CA2239805A1 (en)	1997-06-26
IL124738A (en)	2001-01-28
EP0868397B1 (de)	2000-04-05
MX9804789A (es)	1998-10-31
AU706540B2 (en)	1999-06-17
JP4204068B2 (ja)	2009-01-07
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Date	Code	Title	Description
2016-12-27	MK1K	Patent expired

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