JPH0513959B2 - - Google Patents

Info

Publication number: JPH0513959B2
Authority: JP; Japan
Prior art keywords: formula; lower alkyl; acid; parts; lower alkoxy
Prior art date: 1987-11-20
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

JP1040457A

Other languages

English (en)

Japanese (ja)

Other versions

JPH02221289A (ja

Inventor

Efu Fuiiman Jeimuzu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Crompton and Knowles Corp

Original Assignee

Crompton and Knowles Corp

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.)

1987-11-20

Filing date

1989-02-22

Publication date

1993-02-23

1987-11-20 Priority to US07/123,233 priority Critical patent/US4851158A/en

1989-02-15 Priority to CA000591144A priority patent/CA1338740C/en

1989-02-22 Application filed by Crompton and Knowles Corp filed Critical Crompton and Knowles Corp

1989-02-22 Priority to JP1040457A priority patent/JPH02221289A/ja

1989-03-03 Priority to EP89302151A priority patent/EP0385010A1/en

1990-09-04 Publication of JPH02221289A publication Critical patent/JPH02221289A/ja

1993-02-23 Publication of JPH0513959B2 publication Critical patent/JPH0513959B2/ja

Status Granted legal-status Critical Current

Links

125000000217 alkyl group Chemical group 0.000 claims description 32
125000003545 alkoxy group Chemical group 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
229910052744 lithium Inorganic materials 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
229910052791 calcium Inorganic materials 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
150000002894 organic compounds Chemical class 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000975 dye Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
239000002244 precipitate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229920003043 Cellulose fiber Polymers 0.000 description 3
HSMRCPIZVMDSHN-UHFFFAOYSA-N methylaminomethylphosphonic acid Chemical compound CNCP(O)(O)=O HSMRCPIZVMDSHN-UHFFFAOYSA-N 0.000 description 3
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical class NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 2
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
KMMKKNKMHUQJAW-UHFFFAOYSA-N 2-methylaminoethylphosphonic acid Chemical compound CNCCP(O)(O)=O KMMKKNKMHUQJAW-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FCKXFMPRFMWXPG-UHFFFAOYSA-N [(3-acetamido-4-methoxyphenyl)sulfonyl-methylamino]methylphosphonic acid Chemical compound COC1=CC=C(S(=O)(=O)N(C)CP(O)(O)=O)C=C1NC(C)=O FCKXFMPRFMWXPG-UHFFFAOYSA-N 0.000 description 2
YDCKDKFIHDYXLO-UHFFFAOYSA-N [(3-amino-4-methoxyphenyl)sulfonyl-methylamino]methylphosphonic acid Chemical compound COC1=CC=C(S(=O)(=O)N(C)CP(O)(O)=O)C=C1N YDCKDKFIHDYXLO-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
-1 aminophenylsulfonyl Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000005181 nitrobenzenes Chemical class 0.000 description 2
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000985 reactive dye Substances 0.000 description 2
GPYLWKMYVPRKSH-UHFFFAOYSA-N (2-methylpropylamino)methylphosphonic acid Chemical compound CC(C)CNCP(O)(O)=O GPYLWKMYVPRKSH-UHFFFAOYSA-N 0.000 description 1
MBDCBTOEWVPLSQ-UHFFFAOYSA-N (butan-2-ylamino)methylphosphonic acid Chemical compound CCC(C)NCP(O)(O)=O MBDCBTOEWVPLSQ-UHFFFAOYSA-N 0.000 description 1
FMWGIMDTFSHCKC-UHFFFAOYSA-N (decylamino)methylphosphonic acid Chemical compound CCCCCCCCCCNCP(O)(O)=O FMWGIMDTFSHCKC-UHFFFAOYSA-N 0.000 description 1
HHDGRFIBBFONJY-UHFFFAOYSA-N (heptylamino)methylphosphonic acid Chemical compound CCCCCCCNCP(O)(O)=O HHDGRFIBBFONJY-UHFFFAOYSA-N 0.000 description 1
NBVNPDBXGVDHBY-UHFFFAOYSA-N (hexylamino)methylphosphonic acid Chemical compound CCCCCCNCP(O)(O)=O NBVNPDBXGVDHBY-UHFFFAOYSA-N 0.000 description 1
DWNZJBOIDDGEJJ-UHFFFAOYSA-N (nonylamino)methylphosphonic acid Chemical compound CCCCCCCCCNCP(O)(O)=O DWNZJBOIDDGEJJ-UHFFFAOYSA-N 0.000 description 1
PNLWDYIWVDTPPO-UHFFFAOYSA-N (propan-2-ylamino)methylphosphonic acid Chemical compound CC(C)NCP(O)(O)=O PNLWDYIWVDTPPO-UHFFFAOYSA-N 0.000 description 1
FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
HFZKOYWDLDYELC-UHFFFAOYSA-N 1,2-dimethyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C HFZKOYWDLDYELC-UHFFFAOYSA-N 0.000 description 1
HDFQKJQEWGVKCQ-UHFFFAOYSA-N 1,3-dimethyl-2-nitrobenzene Chemical compound CC1=CC=CC(C)=C1[N+]([O-])=O HDFQKJQEWGVKCQ-UHFFFAOYSA-N 0.000 description 1
BYFNZOKBMZKTSC-UHFFFAOYSA-N 1,3-dimethyl-5-nitrobenzene Chemical compound CC1=CC(C)=CC([N+]([O-])=O)=C1 BYFNZOKBMZKTSC-UHFFFAOYSA-N 0.000 description 1
ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
NWESJZZPAJGHRZ-UHFFFAOYSA-N 1-chloro-4-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C([N+]([O-])=O)=C1 NWESJZZPAJGHRZ-UHFFFAOYSA-N 0.000 description 1
HQCZLEAGIOIIMC-UHFFFAOYSA-N 1-methoxy-2-methyl-3-nitrobenzene Chemical compound COC1=CC=CC([N+]([O-])=O)=C1C HQCZLEAGIOIIMC-UHFFFAOYSA-N 0.000 description 1
MGBRGNWARSQECY-UHFFFAOYSA-N 1-methoxy-3-methyl-2-nitrobenzene Chemical compound COC1=CC=CC(C)=C1[N+]([O-])=O MGBRGNWARSQECY-UHFFFAOYSA-N 0.000 description 1
UGAXDAGIKIVCQB-UHFFFAOYSA-N 1-nitro-2-propylbenzene Chemical compound CCCC1=CC=CC=C1[N+]([O-])=O UGAXDAGIKIVCQB-UHFFFAOYSA-N 0.000 description 1
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
BBUPBICWUURTNP-UHFFFAOYSA-N 2,4-dimethyl-1-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=C1 BBUPBICWUURTNP-UHFFFAOYSA-N 0.000 description 1
NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
CTRQRTFVPNGRFV-UHFFFAOYSA-N 2-amino-5-[methyl(phosphonomethyl)sulfamoyl]benzoic acid Chemical compound OP(=O)(O)CN(C)S(=O)(=O)C1=CC=C(N)C(C(O)=O)=C1 CTRQRTFVPNGRFV-UHFFFAOYSA-N 0.000 description 1
LLYXJBROWQDVMI-UHFFFAOYSA-N 2-chloro-4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1Cl LLYXJBROWQDVMI-UHFFFAOYSA-N 0.000 description 1
XCSNRORTQRKCHB-UHFFFAOYSA-N 2-chloro-6-nitrotoluene Chemical compound CC1=C(Cl)C=CC=C1[N+]([O-])=O XCSNRORTQRKCHB-UHFFFAOYSA-N 0.000 description 1
XCOUVPWGTSKINY-UHFFFAOYSA-N 2-methoxy-4-methyl-1-nitrobenzene Chemical compound COC1=CC(C)=CC=C1[N+]([O-])=O XCOUVPWGTSKINY-UHFFFAOYSA-N 0.000 description 1
CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
WGYFINWERLNPHR-UHFFFAOYSA-N 3-nitroanisole Chemical compound COC1=CC=CC([N+]([O-])=O)=C1 WGYFINWERLNPHR-UHFFFAOYSA-N 0.000 description 1
QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 1
XWPDPFLBSAPRCO-UHFFFAOYSA-N 4-(chloromethoxy)aniline Chemical compound NC1=CC=C(OCCl)C=C1 XWPDPFLBSAPRCO-UHFFFAOYSA-N 0.000 description 1
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
SQFLFRQWPBEDHM-UHFFFAOYSA-N 4-chloro-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C=C1[N+]([O-])=O SQFLFRQWPBEDHM-UHFFFAOYSA-N 0.000 description 1
ABEUJUYEUCCZQF-UHFFFAOYSA-N 4-chloro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(Cl)=CC=C1[N+]([O-])=O ABEUJUYEUCCZQF-UHFFFAOYSA-N 0.000 description 1
IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
JBORNNNGTJSTLC-UHFFFAOYSA-N 4-methoxy-1-methyl-2-nitrobenzene Chemical compound COC1=CC=C(C)C([N+]([O-])=O)=C1 JBORNNNGTJSTLC-UHFFFAOYSA-N 0.000 description 1
RTZOGYCMIMOVHU-UHFFFAOYSA-N 4-methoxy-2-methyl-1-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(C)=C1 RTZOGYCMIMOVHU-UHFFFAOYSA-N 0.000 description 1
ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
NKBOJCPVEOSSNU-UHFFFAOYSA-N [(4-acetamidophenyl)sulfonyl-methylamino]methylphosphonic acid Chemical compound OP(=O)(O)CN(C)S(=O)(=O)C1=CC=C(NC(C)=O)C=C1 NKBOJCPVEOSSNU-UHFFFAOYSA-N 0.000 description 1
WWZMZMWKUFAPHM-UHFFFAOYSA-N [(4-aminophenyl)sulfonyl-methylamino]methylphosphonic acid Chemical compound OP(=O)(O)CN(C)S(=O)(=O)C1=CC=C(N)C=C1 WWZMZMWKUFAPHM-UHFFFAOYSA-N 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UNKFIRCNNMNOLJ-UHFFFAOYSA-N butylaminomethylphosphonic acid Chemical compound CCCCNCP(O)(O)=O UNKFIRCNNMNOLJ-UHFFFAOYSA-N 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
QZJYHWXRWTVKSH-UHFFFAOYSA-N ethylaminomethylphosphonic acid Chemical compound CCNCP(O)(O)=O QZJYHWXRWTVKSH-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
SHLTXWFNRJQZTQ-UHFFFAOYSA-N n-chloro-2-methylaniline Chemical compound CC1=CC=CC=C1NCl SHLTXWFNRJQZTQ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
HKTBRYQNVRPBCF-UHFFFAOYSA-N nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 HKTBRYQNVRPBCF-UHFFFAOYSA-N 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
MWFXTGOTJMBMJI-UHFFFAOYSA-N propylaminomethylphosphonic acid Chemical compound CCCNCP(O)(O)=O MWFXTGOTJMBMJI-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/523—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl amido or hydroxyalkyl amino sulfonyl group, a quaternised or non-quaternised amino alkyl sulfonyl amido group, or a substituted alkyl amino sulfonyl group, or a halogen alkyl sulfonyl amido or halogen alkyl amino sulfonyl group or a vinyl sulfonylamido or a substituted vinyl sulfonamido group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)

JP1040457A 1987-11-20 1989-02-22 Ｎ‐アルキル‐ｎ‐（アミノフエニルスルホニル）‐アミノアルキルホスホン酸及びその製造方法 Granted JPH02221289A (ja)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
US07/123,233 US4851158A (en)	1987-11-20	1987-11-20	N-alkyl-N-(aminophenylsulfonyl)-aminoalkylphosphonic acids
CA000591144A CA1338740C (en)	1987-11-20	1989-02-15	N-alkyl-n(aminophenylsulfonyl)-aminoalkylphosphonic acids
JP1040457A JPH02221289A (ja)	1987-11-20	1989-02-22	Ｎ‐アルキル‐ｎ‐（アミノフエニルスルホニル）‐アミノアルキルホスホン酸及びその製造方法
EP89302151A EP0385010A1 (en)	1987-11-20	1989-03-03	N-alkyl-N-(Aminophenylsulfonyl)-aminoalkylphosphonic acids and salts

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US07/123,233 US4851158A (en)	1987-11-20	1987-11-20	N-alkyl-N-(aminophenylsulfonyl)-aminoalkylphosphonic acids
CA000591144A CA1338740C (en)	1987-11-20	1989-02-15	N-alkyl-n(aminophenylsulfonyl)-aminoalkylphosphonic acids
JP1040457A JPH02221289A (ja)	1987-11-20	1989-02-22	Ｎ‐アルキル‐ｎ‐（アミノフエニルスルホニル）‐アミノアルキルホスホン酸及びその製造方法
EP89302151A EP0385010A1 (en)	1987-11-20	1989-03-03	N-alkyl-N-(Aminophenylsulfonyl)-aminoalkylphosphonic acids and salts

Publications (2)

Publication Number	Publication Date
JPH02221289A JPH02221289A (ja)	1990-09-04
JPH0513959B2 true JPH0513959B2 (2)	1993-02-23

Family

ID=27426632

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1040457A Granted JPH02221289A (ja)	1987-11-20	1989-02-22	Ｎ‐アルキル‐ｎ‐（アミノフエニルスルホニル）‐アミノアルキルホスホン酸及びその製造方法

Country Status (4)

Country	Link
US (1)	US4851158A (2)
EP (1)	EP0385010A1 (2)
JP (1)	JPH02221289A (2)
CA (1)	CA1338740C (2)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1401201A (en) *	1972-04-28	1975-07-16	Ici Ltd	Aryl sulphonamides containing fluorocarbon groups
DE2261081A1 (de) *	1972-12-14	1974-06-27	Bayer Ag	Amidomethanphosphonsaeure-derivate
US3996040A (en) *	1974-06-28	1976-12-07	Monsanto Company	Increasing sucrose content of sugar cane employing N-phenylsulfonamido-N-phosphonomethyl glycine and certain derivatives thereof
US3910969A (en) *	1974-06-28	1975-10-07	Monsanto Co	N-phenylsulfonamido-n-phosphonomethyl glycine and certain derivatives thereof

1987
- 1987-11-20 US US07/123,233 patent/US4851158A/en not_active Expired - Fee Related
1989
- 1989-02-15 CA CA000591144A patent/CA1338740C/en not_active Expired - Fee Related
- 1989-02-22 JP JP1040457A patent/JPH02221289A/ja active Granted
- 1989-03-03 EP EP89302151A patent/EP0385010A1/en not_active Withdrawn

Also Published As

Publication number	Publication date
JPH02221289A (ja)	1990-09-04
US4851158A (en)	1989-07-25
CA1338740C (en)	1996-11-26
EP0385010A1 (en)	1990-09-05

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