KR930013005A - Fiber-reactive disazo compounds - Google Patents

Fiber-reactive disazo compounds Download PDF

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KR930013005A
KR930013005A KR1019920024705A KR920024705A KR930013005A KR 930013005 A KR930013005 A KR 930013005A KR 1019920024705 A KR1019920024705 A KR 1019920024705A KR 920024705 A KR920024705 A KR 920024705A KR 930013005 A KR930013005 A KR 930013005A
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radical
compound
hydrogen
alkyl
phenyl
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KR100236804B1 (en
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기즐러 마르쿠스
왈드 롤랑
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쟝 크라머, 한스 루돌프 하우스
산도즈 리미티드
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    • 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
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
    • C09B62/24—Azo dyes
    • C09B62/25—Disazo or polyazo dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/10—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems
    • 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
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/022—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring the heterocyclic ring being alternatively specified
    • C09B62/026—Azo dyes
    • C09B62/03—Disazo or polyazo dyes
    • 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
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes
    • C09B62/09—Disazo or polyazo dyes
    • 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
    • C09B62/4401—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4424—Azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

유리산 또는 염 형태의 하기 일반식의 섬유-반응성 디스아조 화합물 및 이의 혼합물은, 예를 들면, 가죽, 및 천연 또는 합성 폴리아미드 또는 재생 셀룰로오즈를 포함하는 섬유물질, 가장 바람직하게는 면을 포함하는 텍스타일 물질과 같은 하이드록시 그룹- 또는 질소-함유 유기 기재를 염색 또는 날염하는데 유용하다.Fiber-reactive disazo compounds of the following general formula in free acid or salt form and mixtures thereof include, for example, leather and fibrous material comprising natural or synthetic polyamides or regenerated cellulose, most preferably cotton It is useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates such as textile materials.

수득한 염색물 및 날염물은 양호한 일반적인 견뢰성, 예를 들면 양호한 광견뢰도, 습윤 견뢰도 및 산화 작용에 대한 내성을 나타낸다.The dyeings and printings obtained exhibit good general fastnesses, for example good light fastness, wet fastness and resistance to oxidation.

Description

섬유-반응성 디스아조 화합물Fiber-reactive disazo compounds

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (17)

하기 일반식(Ⅰ)의 화합물 및 그의 염, 또는 이러한 화합물 또는 염들의 혼합물.The compounds of formula (I) and salts thereof, or mixtures of such compounds or salts. R1및 R3는 각각 독립적으로 수소, -COOH 또는 -SO3H 이고, R2및 R4각각 독립적으로 수소, C1-4알킬 또는 C2-4하이드록시 -알킬이며, Q는 헤테로환상 섬유-반응성 라디칼, 또는 -COCHY2-CH2Y1, -COCY2=CH2또는 -COCH2Y1의 그룹(여기서, Y1은 염소, 브롬, -OSO3H 또는 -SSO3H이며, Y2는 수소, 염소 또는 브롬이다)이고, m은 1또는 2이며, n은 0, 1 또는 2이고, z는이며, 단, 각각의 아조 라디칼은 디설포나프틸 라디칼의 아미노 또는 하이드록시 그룹에 대해 오르토 위치에 결합된다.R 1 and R 3 are each independently hydrogen, —COOH, or —SO 3 H, each of R 2 and R 4 is independently hydrogen, C 1-4 alkyl, or C 2-4 hydroxy-alkyl, and Q is heterocyclic fiber-reactive radicals are, or -COCHY 2 -CH 2 Y 1, -COCY 2 = CH 2 or a group -COCH 2 Y 1 (where, Y 1 is chlorine, bromine, -OSO 3 H or -SSO 3 H, Y 2 is hydrogen, chlorine or bromine), m is 1 or 2, n is 0, 1 or 2, z is With the proviso that each azo radical is bonded at the ortho position relative to the amino or hydroxy group of the disulfonaphthyl radical. 제1항에 있어서, 헤테로 환상 섬유-반응성 라디칼로서의 Q가 불안정한 할로겐 치환체를 함유하는 피리미디닐 또는 트리아지닐 라디칼인 화합물.The compound of claim 1, wherein Q as a heterocyclic fiber-reactive radical is a pyrimidinyl or triazinyl radical containing an unstable halogen substituent. 제1항 또는 2항에 있어서, D가 일반식(a)의 라디칼인 화합물.The compound of claim 1 or 2 wherein D is a radical of formula (a). 제1항 내지 제3항중 어느 한 항에 있어서, R1이 R1a이고, R1a가 -COOH 또는 -SO3H이며, R3이 R3a이고, R3a가 수소 또는 -SO3H인 화합물.The compound of any one of claims 1-3, wherein R 1 is R 1a , R 1a is —COOH or —SO 3 H, R 3 is R 3a , and R 3a is hydrogen or —SO 3 H. . 제1항 내지 제3항중 어느 한 항에 있어서, R2이 R2a이고, R4이 R4a이며, R2a및 R4a가 각각 독립적으로 수소, 메틸, 에틸, 또는 2-하이드록시에틸인 화합물.The compound of any one of claims 1-3, wherein R 2 is R 2a , R 4 is R 4a , and R 2a and R 4a are each independently hydrogen, methyl, ethyl, or 2-hydroxyethyl . 제1항 내지 제5항중 어느 한 항에 있어서, Q가 Qa이며, Qa가 라디칼(C), -COCHY2-CO2Y1또는 -COCHY2=CH2이고, Y1이 염소, 브롬, -OSO3H 또는 -SSO3H 이며, Y2가 수소, 염소 또는 브롬이고,또는 =N-이며, YO가 H, F, Cl, -CN, -CHO, -SR5, -SOR5, -SO2R5또는 -SO2F이고, Z1이 H, F, Cl, Br, -NR6R7또는 -OR5이며, Z2가 F, Cl, Br 또는A이고, A-가 비발색성 음이온이며, R5가 수소, C1-4알킬, C1-4하이드록시알킬, 페닐, 또는 카복시 또는 설포에 의해 일치환된 페닐이고, R6및 R7이 각각 독립적으로 수소; C1-4알킬, C2-4하이드록시알킬=페닐 또는 C1-4알킬, C1-4알콕시, 설포 또는 카복시에 의해 일치환된 페닐; 페닐 (C1-3알킬), 또는 페닐환이 C1-4알킬, C1-4알콕시, 설포 또는 카복시에 의해 일치환된 페닐(C1-3알킬); -(CH2)t-SO2-X, -CH2CH2-O-(CH2)t-SO2-X 또는(여기서, t는 2 또는 3이고; X는 -CH=CH2또는 -CH2CH2-Y이며, Y는 하이드록시, 또는 알칼리성 조건하에 분리될 수 있는 라디칼이다) 이거나, 또는 -NR6R7이 피페리딘, 피페라진, N-메틸-피페라진 또는 모르폴리 환이며, R8이 하이드록시, -NH2, 메톡시 또는 에콕시인 화합물.The compound according to any one of claims 1 to 5, wherein Q is Q a and Q a is a radical (C). And, -COCHY 2 -CO 2 Y 1 = CH 2 and 2 or -COCHY, Y 1 is chlorine, and bromine, -OSO 3 H or -SSO 3 H, Y 2 is hydrogen, chlorine or bromine, Or = N-, Y O is H, F, Cl, -CN, -CHO, -SR 5 , -SOR 5 , -SO 2 R 5 or -SO 2 F, and Z 1 is H, F, Cl, Br, -NR 6 R 7 or -OR 5 , Z 2 is F, Cl, Br or A , A − is a non-chromogenic anion, R 5 is hydrogen, C 1-4 alkyl, C 1-4 hydroxyalkyl, phenyl, or phenyl monosubstituted by carboxy or sulfo, and R 6 and R 7 are each Independently hydrogen; C 1-4 alkyl, C 2-4 hydroxyalkyl = phenyl or C 1-4 alkyl, phenyl monosubstituted by C 1-4 alkoxy, sulfo or carboxy; Phenyl (C 1-3 alkyl), or phenyl ring is C 1-4 alkyl, C 1-4 alkoxy, sulfo or carboxy-substituted phenyl (C 1-3 alkyl) by; -(CH 2 ) t -SO 2 -X, -CH 2 CH 2 -O- (CH 2 ) t -SO 2 -X or Where t is 2 or 3; X is -CH = CH 2 or -CH 2 CH 2 -Y and Y is hydroxy, or a radical that can be separated under alkaline conditions) or -NR 6 R 7 is a piperidine, piperazine, N-methyl-piperazine or morpholin ring, and R 8 is hydroxy, -NH 2 , methoxy or epoxy. 제1항에 있어서, 하기 일반식(Ⅰa)에 상응하는 화합물 및 그의 염.The compound and salt thereof according to claim 1, which correspond to the following general formula (Ia). 상기식에서, Z는 제1항에서 정의된 바와 같고, R1 -는 -COOH 또는 -SO3H이며, R2X는 수소, 메틸 또는 에틸이고; D2는 하기 라디칼(a2) 또는 (b3)이며;Wherein Z is as defined in claim 1 , R 1 - is -COOH or -SO 3 H, and R 2X is hydrogen, methyl or ethyl; D 2 is the following radical (a2) or (b3); (여기서, m은 1 또는 2이고, n'는 0 또는 1이며, 이 경우, (CH2)n'-NH-Qd및 (SO3H)m의 위치는 다음과 같다: ⅰ)n'가 1이고, -CH2-NH-Qd는 5-위치에 존재하고; m이 1이고, 설포그룹은 1-위치에 존재하며; ii) n'가1이고, -CH2-NH-Qd는 5-위치에 존재하고; m이 2이고, 설포그룹은 1- 및 7-위치에 존재하며; ⅲ) n'가 0이고, -NH-Qd는 6-위치에 존재하고; m이 2이고, 설포그룹은 4-및 8-위치에 존재한다); Qo는 라디칼(C1')또는 (C2')이고, Qd는 라디칼(C2')이며, 라디칼(C1')는 하기 라디칼(C1)이고, 라디칼(C2')는 하기 라디칼(C2)이며,Wherein m is 1 or 2 and n 'is 0 or 1, in which case the positions of (CH 2 ) n ' -NH-Q d and (SO 3 H) m are as follows: i) n ' Is 1 and -CH 2 -NH-Q d is at the 5-position; m is 1 and the sulfo group is in the 1-position; ii) n 'is 1 and -CH 2 -NH-Q d is at the 5-position; m is 2 and the sulfogroup is in the 1- and 7-positions; Iii) n 'is 0 and -NH-Q d is in the 6-position; m is 2 and the sulfogroup is in the 4- and 8-positions); Q o is a radical (C 1 ′) or (C 2 ′), Q d is a radical (C 2 ′), a radical (C 1 ′) is a radical (C 1 ), and a radical (C 2 ′) is Is a radical (C 2 ), Z1'는 염소 또는 -NR6aR7a이고, R6a및 R7a는 각각 독립적으로 수소, 메틸, 에틸, 2-하이드록시에틸, 페닐 또는 메틸, 메톡시, 설포 또는 카복시에 의해 일치환된 페닐, -(CH2)t-SO2-Xa또는 -CH2CH2-O(CH2)t-SO2-Xa(여기서, t는 2 또는 3이고, Xa는 -CH=CH2, -CH2CH2OH 또는 -CH2CH2OSO3H이다) 이거나, 또는 -NR6aR7a가 피페리딘 또는 모르폴린환이고, Z2'는 F또는 Cl이며, YO'는 수소, Cl 또는 -CN이고, Z1" 및 Z2"는 각각 F 또는 Cl이며, 단 , 각각의 아조 라디칼은 디설포나프틸 라디칼의 아미노 또는 하이드록시 라디칼에 의해 오르토 위치에 결합 된다.Z 1 ′ is chlorine or —NR 6a R 7a , and R 6a and R 7a are each independently hydrogen, methyl, ethyl, 2-hydroxyethyl, phenyl or phenyl monosubstituted by methyl, methoxy, sulfo or carboxy ,-(CH 2 ) t -SO 2 -X a or -CH 2 CH 2 -O (CH 2 ) t -SO 2 -X a , where t is 2 or 3 and X a is -CH = CH 2 , -CH 2 CH 2 OH or -CH 2 CH 2 OSO 3 H), or -NR 6a R 7a is a piperidine or morpholine ring, Z 2 'is F or Cl, Y O ' is hydrogen , Cl or -CN, Z 1 "and Z 2 " are each F or Cl, provided that each azo radical is bonded at the ortho position by the amino or hydroxy radical of the disulfonafyl radical. 제7항에 있어서, 하기 일반식(Ⅰb)에 상응하는 화합물 및 그의 염.8. Compounds and salts thereof according to claim 7, which correspond to the following general formula (Ib). 상기식에서, R2b및 Z는 제7항에서 정의된 바와 같고, -NR2b-Z는 4- 또는 5-위치에 존재하며, D3는 제7항에서 정의된 라디칼(a2)이다.Wherein R 2b and Z are as defined in claim 7, -NR 2b -Z are in the 4- or 5-position and D 3 is the radical (a 2 ) as defined in claim 7. 제8항에 있어서, R2b가 수소인 화합물.The compound of claim 8, wherein R 2b is hydrogen. 제9항에 있어서, -CH-Z가 5-위치에 존재하는 화합물.The compound of claim 9, wherein —CH—Z is at the 5-position. 실제로 실시예 1 내지 42중 어느 하나를 참고로하여 상세한 설명에 기술한 바와 같은 화합물.Indeed a compound as described in the detailed description with reference to any one of Examples 1-42. 1-아미노-8-하이드록시나프탈렌-3,6- 또는 -4,6-디설폰산을, 한편으로는 하기 일반식(Ⅱ)의 아민의 디아조늄염과 반응시키고, 다른 한편으로는 하기 일반식(Ⅲ)의 아민의 디아조늄염과 반응시킴을 포함하는, 제1항에서 정의된 바와 같은 일반식(Ⅰ)의 화합물 또는 이러한 화합물들의 혼합물을 제조하는 방법.1-amino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid is reacted with the diazonium salt of the amine of the following general formula (II) on the one hand, and on the other hand A process for preparing a compound of formula (I) or a mixture of such compounds as defined in claim 1 comprising reacting with a diazonium salt of the amine of (III). 상기식에서, D, R1, R2및 Z는 제1항에서 정의된 바와 같다.Wherein D, R 1 , R 2 and Z are as defined in claim 1. 실제로 실시예 1 내지 42중 어느 하나를 참고로 하여 상세한 설명에 기술한 바와 같은 제1항에서 정의된 일반식(Ⅰ)의 화합물의 제조방법.In fact a process for the preparation of a compound of formula (I) as defined in claim 1 as described in the detailed description with reference to any one of Examples 1-42. 제12항 또는 제13항의 방법에 의해 수득된 일반식(Ⅰ)의 화합물.A compound of formula (I) obtained by the method of claim 12 or 13. 제1항 내지 제10항 및 제14항중 어느 한항의 화합물 또는 이들의 혼합물을 하이드록시 그룹- 또는 질소-함유 유기 기재에 적용시킴을 포함하는, 상기 기재를 염색 또는 날염하는 방법.A method of dyeing or printing a substrate, comprising applying the compound of any one of claims 1 to 10 and 14 or a mixture thereof to a hydroxy group- or nitrogen-containing organic substrate. 제15항에 있어서, 상기 기재가 천연 또는 재생 셀룰로오즈를 포함하는 섬유 물질인 방법.The method of claim 15, wherein the substrate is a fibrous material comprising natural or regenerated cellulose. 실제로 적용실시예 A 내지 C중 어느 하나를 참고로 하여 상세한 설명에 기술한 바와 같은 기재의 염색 및 날염 방법.Process for dyeing and printing substrates as actually described in the detailed description with reference to any of Examples A-C. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
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