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US 2026/0308841 A1Published application
Disperse dyes for dyeing polyester fibres
AssigneeUniversity of Leeds
InventorsRichard Simon BLACKBURN, Christopher Mark RAYNER, Nathaniel Beaumont CROMPTON, Harrison George OATES
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Abstract
The present invention relates to compounds of formula (I): wherein R1 is a dye, and L′, R2 and R3 are as defined herein. The compounds of the invention reversibly convert from a hydrophobic form to a hydrophilic form upon contact with water and carbon dioxide. The present invention also relates to methods of dyeing fibres, and methods of decolouring dyed fibres. The method is particularly useful for dyeing polyester fibres.
Claims25
A method of dyeing fibres, the method comprising the following steps:
- a) subjecting the fibres to a dye liquor comprising water to provide the fibres wetted with the dye liquor;
- b) heating the fibres wetted with the dye liquor to a temperature of from 90° C. to 180° C., to provide dyed fibres wetted with an exhausted dye liquor comprising water;
- and
- c) removing the dyed fibres from the exhausted dye liquor,
- wherein the dye liquor of step a) further comprises:
- i) a compound of Formula (I) and carbon dioxide:
- ii) a salt of Formula (II), a carbamate of Formula (III), or mixtures thereof:
- or
- iii) a salt of Formula (IV) and a metal bicarbonate salt:
- wherein:
- R1a is a dye, optionally substituted with a further L1NR2R3 group;
- R1b is a dye, optionally substituted with a L1NR2R3 group or a further L1NH+R2R3·−OC(O)OH group;
- R1c is a dye, optionally substituted with a L1NR2R3 group, a further L1N+H2R3 group and/or a further L1N(CO2−)R3 group;
- R1d is a dye, optionally substituted with a L1NR2R3 group or a further L1NH+R2R3·−A group;
- A− is an anionic counterion derived from a Brønsted acid;
- L1 is independently at each occurrence selected from —C1-5-alkylene-X—C0-5-alkylene- or —C0-5-alkylene-X—C1-5-alkylene-, wherein X is absent or selected from C3-6-cycloalkylene, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R2 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- L1 and R2 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl optionally substituted, where chemically possible, by 1 to 3 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2Ra, ORa, SRa, S(O)Ra, S(O)2Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein the heterocyclyl has 0 to 2 additional heteroatom ring vertices selected from the group consisting of O, N, and S;
- R3 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- R2 and R3 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl;
- R4 is independently at each occurrence selected from:
- C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R5 is independently at each occurrence selected from:
- OR6, CO2R6, NR6R7, CONR6R7, SR6, and S(O)2NR6R7;
- R6 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl;
- R7 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C(O)R8, S(O)2R8;
- and
- R8 is independently at each occurrence C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- wherein any R1-R8 group that is an alkyl, alkylene, cycloalkyl, heterocyclyl, phenyl or heteroaryl may be optionally substituted, where chemically possible, by 1 to 5 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2Ra, ORa, SRa, S(O)R8, S(O)2Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein Ra is independently at each occurrence selected from H and unsubstituted C1-C4-alkyl;
- and Rb is independently at each occurrence selected from H, unsubstituted C1-C4-alkyl, unsubstituted C(O)—C1-C4-alkyl, and unsubstituted S(O)2—C1-C4-alkyl.
33 more elements
A salt of Formula (II):
- wherein:
- R1b is a dye, optionally substituted with a L1NR2R3 group or a further L1NH+R2R3·−OC(O)OH group;
- L1 is independently at each occurrence selected from —C1-5-alkylene-X—C0-5-alkylene- or —C0-5-alkylene-X—C1-5-alkylene-, wherein X is absent or selected from C3-6-cycloalkylene, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R2 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- L1 and R2 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl optionally substituted, where chemically possible, by 1 to 3 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2Ra, ORa, SRa, S(O)Ra, S(O)2Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein the heterocyclyl has 0 to 2 additional heteroatom ring vertices selected from the group consisting of O, N, and S;
- R3 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- R2 and R3 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl;
- R4 is independently at each occurrence selected from:
- C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R5 is independently at each occurrence selected from:
- OR6, CO2R6, NR6R7, CONR6R7, SR6, and S(O)2NR6R7;
- R6 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl;
- R7 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C(O)R8, S(O)2R8;
- and
- R8 is independently at each occurrence C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- wherein any R1-R8 group that is an alkyl, alkylene, cycloalkyl, heterocyclyl, phenyl or heteroaryl may be optionally substituted, where chemically possible, by 1 to 5 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2Ra, ORa, SRa, S(O)Ra, S(O)2Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein Ra is independently at each occurrence selected from H and unsubstituted C1-C4-alkyl;
- and Rb is independently at each occurrence selected from H, unsubstituted C1-C4-alkyl, unsubstituted C(O)—C1-C4-alkyl, and unsubstituted S(O)2—C1-C4-alkyl.
20 more elements
A carbamate of Formula (III):
- wherein:
- R1a is a dye, optionally substituted with a L1NR2R3 group, a further L1N+H2R3 group and/or a further L1N(CO2−)R3 group;
- L1 is independently at each occurrence selected from —C1-5-alkylene-X—C0-5-alkylene- or —C0-5-alkylene-X—C1-5-alkylene-, wherein X is absent or selected from C3-6-cycloalkylene, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R2 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- L1 and R2 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl optionally substituted, where chemically possible, by 1 to 3 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2Ra, ORa, SRa, S(O)Ra, S(O)2Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein the heterocyclyl has 1 to 2 additional heteroatom ring vertices selected from the group consisting of O, N, and S;
- R3 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- R2 and R3 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl;
- R4 is independently at each occurrence selected from:
- C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R5 is independently at each occurrence selected from:
- OR6, CO2R6, NR6R7, CONR6R7, SR6, and S(O)2NR6R7;
- R6 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl;
- R7 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C(O)R8, S(O)2R8;
- and
- R8 is independently at each occurrence C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- wherein any R1-R8 group that is an alkyl, alkylene, cycloalkyl, heterocyclyl, phenyl or heteroaryl may be optionally substituted, where chemically possible, by 1 to 5 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2Ra, ORa, SRa, S(O)Ra, S(O)2Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONR2R2, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein Ra is independently at each occurrence selected from H and unsubstituted C1-C4-alkyl;
- and Rb is independently at each occurrence selected from H, unsubstituted C1-C4-alkyl, unsubstituted C(O)—C1-C4-alkyl, and unsubstituted S(O)2—C1-C4-alkyl.
20 more elements
A salt of Formula (IV):
- wherein:
- R1d is a dye, optionally substituted with a L1NR2R3 group or a further L1NH+R2R3·−A group;
- A− is an anionic counterion derived from a Brønsted acid;
- L1 is independently at each occurrence selected from —C1-5-alkylene-X—C0-5-alkylene- or —C0-5-alkylene-X—C1-5-alkylene-, wherein X is absent or selected from C3-6-cycloalkylene, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R2 is independently at each occurrence selected from H, C1-5-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- L1 and R2 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl optionally substituted, where chemically possible, by 1 to 3 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2a, ORa, SRa, S(O)a, S(O)2Ra, S(O)2NRa, CO2Ra, C(O)a, CONRaRa, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein the heterocyclyl has 0 to 2 additional heteroatom ring vertices selected from the group consisting of O, N, and S;
- R3 is independently at each occurrence selected from H, C1-6alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C1-4-alkylene-R4, and C2-4-alkylene-R5;
- or
- R2 and R3 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl;
- R4 is independently at each occurrence selected from:
- C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- R5 is independently at each occurrence selected from:
- OR6, CO2R6, NR6R7, CONR6R7, SR6, and S(O)2NR6R7;
- R6 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl;
- R7 is independently at each occurrence selected from H, C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, C(O)R8, S(O)2R8;
- and
- R8 is independently at each occurrence C1-6-alkyl, C3-6-cycloalkyl, 4- to 7-membered heterocyclyl, 5- to 10-membered heteroaryl and phenyl;
- wherein any R1-R8 group that is an alkyl, alkylene, cycloalkyl, heterocyclyl, phenyl or heteroaryl may be optionally substituted, where chemically possible, by 1 to 5 substituents which are each independently selected at each occurrence from:
- oxo, ═NRa, ═NORa, halo, nitro, cyano, NRaRb, NRaS(O)2Ra, NRaC(O)Ra, NRaCONRaRa, NRaCO2Ra, ORa, SRa, S(O)Ra, S(O)2Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa, unsubstituted C1-C4-alkyl, unsubstituted C2-C4-alkenyl, unsubstituted C2-C4-alkynyl and unsubstituted C1-C4-haloalkyl;
- wherein Ra is independently at each occurrence selected from H and unsubstituted C1-C4-alkyl;
- and Rb is independently at each occurrence selected from H, unsubstituted C1-C4-alkyl, unsubstituted C(O)—C1-C4-alkyl, and unsubstituted S(O)2—C1-C4-alkyl.
21 more elements
The method, salt, or carbamate according to any preceding claim, wherein R1a, R1b, R1c and R1d is a disperse dye.
Dependencies are inferred from the claim text.