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US 7,442,780 B2Granted
Reactive dye compounds
AssigneeNorth Carolina State University
InventorsWei Dong He, Peter Jeffrey Broadbent, David Malcolm Lewis
Life of this patent
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Abstract
New, highly multifunctional reactive dye compounds are provided. The number of leaving groups in the non-chromophoric part of the molecule added to the number of chromophore moieties is at least equal to 5, preferably in the range of from 5 to 12, more preferably from 5 to 6. The new reactive dye compounds preferably have at least two asymmetric bridges.
Claims17
A reactive dye compound having the formula (I) below:
- wherein
- D is a chromophore;
- L is a linking moiety, preferably selected from the group consisting of —NR—, —C(O)NR—, —NRSO2—, —(CH2)k— and —SO2—(CH2)k— wherein R is H or C1-C4 alkyl which can be substituted by halogen, preferably fluorine or chlorine, hydroxyl, cyano, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato and wherein k is an integer with a value between 1 and 4;
- Z is any moiety forming at least three covalent bonds with other moieties, preferably selected from the group consisting of nitrogen (N),
- and aromatic compounds, more preferably from the group consisting of aromatic compounds activated by electron withdrawing groups and N-heterocycles, even more preferably from the group consisting of triazine, pyrimidine, quinoxaline, pyrimidinone, phthalazine, pyridazone, pyrazine and
- still more preferably from the group consisting of triazine, pyrimidine, and quinoxaline, still even more preferably from triazine;
- Y is any leaving group, preferably selected from the group consisting of —Cl, —Br, —F, —I, —SO3H, —OSO3H, —SSO3H, —O—C6H4—SO3H, —OCO—CH3, —OPO3H2, —OCO—C6H5, —OSO2—C1-C4 alkyl, —OSO2—N(C1-C4 alkyl)2,
- and quaternized nitrogen derivatives, more preferably selected from the group consisting of —Cl, —Br, —F and —OSO3H, even more preferably from the group consisting of —F and —Cl when Y is bonded to an N-containing heterocycle and —Br when Y is bonded to
- G1 is selected from the group consisting of Y and —B—G2;
- G2 is selected from the group consisting of
- B is a bridging moiety selected from the group consisting of —S—,
- and —S—CR′2—CR′2—
- wherein R′ is selected from the group consisting of H, C1-C10 alkyl group, C1-C10 carboxylic acid and sulphonate, preferably H;
- and
- wherein R″ is selected from the group consisting of H, C1-C4 alkyl group and —CR′2—CR′2—S—G2;
- B preferably being —NH—CH2—CH2—S— or —NH—CHCOOH—CH2—S—,
- wherein when there is more than one D, R, R′, R″, L, Z, Y, G1, G2 or B these are not necessarily the same;
- and
- wherein the reactive dye compound comprises at least one group G2;
- and salts and esters thereof.
17 more elements
A reactive dye compound having the formula (II):
- wherein
- D is a chromophore;
- L is a linking moiety, preferably selected from the group consisting of —NR—, —C(O)NR—, —NRSO2—, —(CH2)k— and —SO2—(CH2)k— wherein R is H or C1-C4 alkyl which can be substituted by halogen, preferably fluorine or chlorine, hydroxyl, cyano, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato and wherein k is an integer with a value between 1 and 4;
- Z is any moiety forming at least three covalent bonds with other moieties, preferably selected from the group consisting of nitrogen (N),
- and aromatic compounds, more preferably from the group consisting of aromatic compounds activated by electron withdrawing groups and N-heterocycles, even more preferably from the group consisting of triazine, pyrimidine, quinoxaline, pyrimidinone, phthalazine, pyridazone, pyrazine and
- still more preferably from the group consisting of triazine, pyrimidine, and quinoxaline, still even more preferably from triazine;
- Y is any leaving group, preferably selected from the group consisting of —Cl, —Br, —F, —I, —SO3H, —OSO3H, —SSO3H, —O—C6H4—SO3H, —OCO—CH3, —OPO3H2, —OCO—C6H5, —OSO2—C1-C4 alkyl, —OSO2—N(C1-C4 alkyl)2,
- and quaternized nitrogen derivatives, more preferably selected from the group consisting of —Cl, —Br, —F and —OSO3H, even more preferably from the group consisting of —F and —Cl when Y is bonded to an N-containing heterocycle and —Br when Y is bonded to
- B is
- wherein R′ is selected from the group consisting of H, C1-C10 alkyl group, C1-C10 carboxylic acid and sulphonate, preferably H;
- and
- R″ is selected from the group consisting of H, C1-C4 alkyl group,
- B preferably being —NH—CH2—CH2—S— or —NH—CHCOOH—CH2—S—,
- wherein when there is more than one D, L, Z, Y, R, R′, R″ or B group these are not necessarily the same;
- and salts and esters thereof.
12 more elements
A reactive dye compound having the formula (IV):
- wherein
- D is a chromophore;
- L is a linking moiety, preferably selected from the group consisting of —NR—, —C(O)NR—, —NRSO2—, —(CH2)k— and —SO2—(CH2)k— wherein R is H or C1-C4 alkyl which can be substituted by halogen, preferably fluorine or chlorine, hydroxyl, cyano, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato and wherein k is an integer with a value between 1 and 4;
- Z is any moiety forming at least three covalent bonds with other moieties, preferably selected from the group consisting of nitrogen (N),
- and aromatic compounds, more preferably from the group consisting of aromatic compounds activated by electron withdrawing groups and N-heterocycles, even more preferably from the group consisting of triazine, pyrimidine, quinoxaline, pyrimidinone, phthalazine, pyridazone, pyrazine and
- still more preferably from the group consisting of triazine, pyrimidine, and quinoxaline, still even more preferably from triazine;
- Y is any leaving group, preferably selected from the group consisting of —Cl, —Br, —F, —I, —SO3H, —OSO3H, —SSO3H, —O—C6H4—SO3H, —OCO—CH3, —OPO3H2, —OCO—C6H5, —OSO2—C1-C4 alkyl, —OSO2—N(C1-C4 alkyl)2,
- and quaternized nitrogen derivatives, more preferably selected from the group consisting of —Cl, —Br, —F and —OSO3H, even more preferably from the group consisting of —F and —Cl when Y is bonded to an N-containing heterocycle and —Br when Y is bonded to
- G1 is selected from the group consisting of Y and —B-G2;
- G2 is selected from the group consisting of
- B is a bridging moiety selected from the group consisting of —S—,
- wherein R′ is selected from the group consisting of H, C1-C10 alkyl group, C1-C10 carboxylic acid and sulphonate, preferably H;
- and
- wherein R″ is selected from the group consisting of H, C1-C4 alkyl group and —CR′2—CR′2—S-G2,
- wherein at least one, and preferably all, B is —S—;
- wherein when there is more than one B, D, R, L, Z, Y, G1 or G2 within the same molecule these are not necessarily the same;
- and
- wherein the reactive dye compound comprises at least one group G2;
- and salts and esters thereof.
16 more elements
A reactive dye compound having the formula (V):
- wherein
- D is a chromophore;
- L is a linking moiety, preferably selected from the group consisting of —NR—, —C(O)NR—, —NRSO2—, —(CH2)k— and —SO2—(CH2)k — wherein R is H or C1-C4 alkyl which can be substituted by halogen, preferably fluorine or chlorine, hydroxyl, cyano, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato and wherein k is an integer with a value between 1 and 4;
- Z is any moiety forming at least three covalent bonds with other moieties, preferably selected from the group consisting of nitrogen
- and aromatic compounds, more preferably from the group consisting of aromatic compounds activated by electron withdrawing groups and N-heterocycles, even more preferably from the group consisting of triazine, pyrimidine, quinoxaline, pyrimidinone, phthalazine, pyridazone, pyrazine and
- still more preferably from the group consisting of triazine, pyrimidine, and quinoxaline, still even more preferably from triazine;
- Y is any leaving group, preferably selected from the group consisting of —Cl, —Br, —F, —I, —SO3H, OSO3H, —SSO3H, —O—C6H4—SO3H, —OCO—CH3, —OPO3H2, —OCO—C6H5, —OSO2—C1-C4 alkyl, —OSO2—N(C1-C4 alkyl)2,
- and quaternized nitrogen derivatives, more preferably selected from the group consisting of —Cl, —Br, —F and —OSO3H, even more preferably from the group consisting of —F and —Cl when Y is bonded to an N-containing heterocycle and —Br when Y is bonded to
- G1 is selected from the group consisting of Y and —B-G2;
- G2 is selected from the group consisting of
- B is a bridging group selected from the group consisting of
- and —S—CR′2—CR′2;
- wherein R″ is selected from the group consisting of H, C1-C4 alkyl group and —CR′2—CR′2—S-G2;
- and
- wherein R′ is selected from the group consisting of H, C1-C10 alkyl group, C1-C10 carboxylic acid and sulphonate, preferably H,
- wherein when there is more than one D, R, R′, R″, L, Z, Y, G1, G2, or B group they are not necessarily the same;
- and
- wherein the reactive dye compound comprises at least one bridging group B wherein R″ is —CR′2—CR′2—S-G2;
- and salts and esters thereof.
16 more elements
A reactive dye compound having the formula (VI)
- wherein
- D is a chromophore;
- L is a linking moiety, preferably selected from the group consisting of —NR—, —C(O)NR—, —NRSO2—, —(CH2)k— and —SO2—(CH2)k— wherein R is H or C1-C4 alkyl which can be substituted by halogen, preferably fluorine or chlorine, hydroxyl, cyano, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato and wherein k is an integer with a value between 1 and 4;
- Z is any moiety forming at least three covalent bonds with other moieties, preferably selected from the group consisting of nitrogen (N),
- and aromatic compounds, more preferably from the group consisting of aromatic compounds activated by electron withdrawing groups and N-heterocycles, even more preferably from the group consisting of triazine, pyrimidine, quinoxaline, pyrimidinone, phthalazine, pyridazone, pyrazine and
- still more preferably from the group consisting of triazine, pyrimidine, and quinoxaline, still even more preferably from triazine;
- Y is any leaving group, preferably selected from the group consisting of —Cl, —Br, —F, —I, —SO3H, —OSO3H, —SSO3H, —O—C6H4—SO3H, —OCO—CH3, —OPO3H2, —OCO—C6H5, —OSO2—C1-C4 alkyl, —OSO2—N(C1-C4 alkyl)2,
- and quaternized nitrogen derivatives, more preferably selected from the group consisting of —Cl, —Br, —F and —OSO3H, even more preferably from the group consisting of —F and —Cl when Y is bonded to an N-containing heterocycle and —Br when Y is bonded to
- G1 is selected from the group consisting of Y and —B-G2;
- G2 is selected from the group consisting of
- B is a bridging moiety, preferably selected from the group consisting of —S—,
- and —S—CR′2—CR′2
- wherein R″ is selected from the group consisting of H, C1-C4 alkyl group and —CR′2 CR′2S-G2
- wherein R′ is selected from the group consisting of H, C1-C10 alkyl group C1-C10 carboxylic acid and sulphonate, preferably H,
- B preferably being —NH—CH2—CH2—S— or —NH—CHCOOH—CH2—S—,
- wherein when there is more than one D, R, R′, R″, L, Z, Y, G1, G2 or B group they are not necessarily the same;
- wherein the reactive dye compound comprises at least one group G2;
- and salts and esters thereof.
15 more elements
A method for synthesizing a reactive dye compound of Formula (I):
- wherein:
- D is a chromophore;
- L is a linking moiety, preferably selected from the group consisting of —NR—, —C(O)NR—, —NRSO2—, —(CH2)k— and —SO2—(CH2)k— wherein R is H or C1-C4 alkyl which can be substituted by halogen, preferably fluorine or chlorine, hydroxyl, cyano, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato and wherein k is an integer with a value between 1 and 4;
- Z is any moiety forming at least three covalent bonds with other moieties, preferably selected from the group consisting of nitrogen (N),
- and aromatic compounds, more preferably from the group consisting of aromatic compounds activated by electron withdrawing groups and N-heterocycles, even more preferably from the group consisting of triazine, pyrimidine, quinoxaline, pyrimidinone, phthalazine, pyridazone, pyrazine and
- still more preferably from the group consisting of triazine, pyrimidine, and quinoxaline, still even more preferably from triazine;
- Y is any leaving group, preferably selected from the group consisting of —Cl, —Br, —F, —I, —SO3H, —OSO3H, —SSO3H, —O—C6H4—SO3H, —OCO—CH3, OPO3H2, —OCO—C6H5, —OSO2—C1-C4 alkyl, —OSO2—N(C1-C4 alkyl)2,
- and quaternized nitrogen derivatives, more preferably selected from the group consisting of —Cl, —Br, —F and —OSO3H, even more preferably from the group consisting of —F and —Cl when Y is bonded to an N-containing heterocycle and —Br when Y is bonded to
- G1 is selected from the group consisting of Y and —B-G2;
- G2 is selected from the group consisting of
- B is a dissymmetric bridging moiety having the formula —S—CR′2—CR′2—N(R″)—, wherein R′ is selected from the group consisting of H, C1-C10 alkyl group, C1-C10 carboxylic acid, and sulphonate;
- and R″ is selected from the group consisting of H and C1-C4 alkyl group;
- wherein when there is more than one D, R, R′, R″, L, Z, Y, G1, G2, or B these are not necessarily the same;
- wherein the reactive dye compound comprises at least one group G2;
- and
- wherein at least one R′ is COOH;
- and
- salts and esters thereof;
- wherein said method comprises the steps of:
- a) reacting a starting reactive dye compound with a first group of bridging moiety B and forming one bond, and
- b) reacting a second group of said bridging moiety B with a moiety Z.
18 more elements
Dependencies are inferred from the claim text.