# US 9,518,355 B2 · Processes and compositions for dyeing or finishing fibrous materials

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- Number: US 9,518,355 B2
- Document ID: US9518355B2
- Status: Granted
- Kind: B2
- Application number: 14/406,837
- Filed: 2013-06-28
- Published: 2015-06-11
- Granted: 2016-12-13
- Earliest claimed: 2012-07-02
- Assignees: Huntsman Textile Effects (Germany) GmbH
- Applicants: Huntsman Textile Effects (Germany) GmbH
- Inventors: Harald Chrobaczek; Günther Tschida; Tanja Refle; Ernst Jan Siewers
- Web page: https://patentgrep.com/patent/US9518355B2

## CPC

- D06M 15/53: Polyethers (polyacetals D06M15/39)
- C08G 65/329: with organic compounds
- C08G 65/331: containing oxygen {(cyclic ether compounds C08G65/26)}
- C08G 65/3324: {cyclic}
- C08G 65/336: containing silicon
- D06M 11/76: with carbon oxides or carbonates (D06M11/75 takes precedence; with percarbonic acids or their salts D06M11/50; with urea D06M13/432)
- D06M 13/513: with at least one carbon-silicon bond
- D06M 15/643: containing silicon in the main chain
- D06M 23/105: {Processes in which the solvent is in a supercritical state}
- D06P 1/94: using dyes dissolved in solvents which are in the supercritical state
- C08G 2650/50: containing nitrogen, e.g. polyetheramines or Jeffamines(r)
- C08L 2203/12: used for fibers
- D06M 2101/32: Polyesters
- Y02P 20/54: using solvents, e.g. supercritical solvents or ionic liquids
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- D06P: DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Compositions comprising a specific ethoxylated/propoxylated product as well as an alkylene carbonate, an epoxysilane or a polysiloxane are useful for dyeing or finishing fibrous materials. Reaction products formed from said products are also very useful for these purposes. Said products are preferably used as solutions in supercritical carbon dioxide.

## Claims

### Claim 1

A process for dyeing or finishing fibrous materials which comprises applying to the fibrous materials a solution comprising:
i) a product of formula (Ia) and/or a product of formula (Ib),
each dissolved in a liquid in the supercritical state, and optionally in admixture with a product selected from a product of formula (II), a product of formula (III), a product of formula (IV), an α-aminocarboxylic acid and a mixture thereof,
where
E represents hydrogen or R1,
R1 represents alkyl of 1 to 13 carbon atoms,
one of R2 and R3 represents —CH3 while the other represents H,
R4 represents H, —CH3, —CH2—CH3 or —CH2—OH,
R5 in each occurrence independently represents R1 or —OH or —OR1,
R6 in either occurrence independently represents R5 or R8,
R7 in each occurrence independently represents R1,
R8 in each occurrence independently represents a radical of formula (V) or of formula (VI),
R9 in each occurrence independently represents hydrogen or —CH3,
—X—NH2 (V)
—Y—NH—Z—NH2 (VI)
b represents 0 or 1 in the case of formula (Ia) and a number from 0 to 15 in the case of formula (Ib),
t represents a number from 5 to 14 and the b:t ratio represents a number from 0 to 0.2 in formula (Ia) and from 0 to 1.1 in formula (Ib),
k represents a number from 0 to 1000, and
X and Y each independently represent a linear or branched alkylene radical of 1 to 4 carbon atoms and Z represents a linear or branched alkylene radical of 2 to 4 carbon atoms; and/or
ii) a product dissolved in a liquid in the supercritical state obtained by reacting one or more products of formulae (Ia) and/or (Ib) as defined above with one or more products of formulae (II) and/or (III) as defined above.

### Claim 2 (depends on 1)

The process as claimed in claim 1 wherein the liquid in the supercritical state is supercritical carbon dioxide.

### Claim 3 (depends on 2)

The process as claimed in claim 2 wherein the concentration of the product of i) dissolved in supercritical carbon dioxide and/or the product of ii) dissolved in supercritical carbon dioxide is in the range from 0.0005% to 0.5% by weight.

### Claim 4 (depends on 1)

The process as claimed in claim 1 wherein said solution further comprises iii) an acrylic ester or a polydialkylsiloxane with or without substitution by OH or by OR1 groups or by radicals having amino groups.

### Claim 5 (depends on 1)

The process as claimed in claim 1 wherein the product of i) and/or the product of ii): is soluble in water at not less than 0.0001 mol per mole of water; and, is soluble in the liquid the supercritical state at not less than 0.0001 mol per mole of liquid in the supercritical state.

### Claim 6 (depends on 5)

The process as claimed in claim 5 wherein the product of i) and/or the product of ii): has a solubility in water of 0.001 mol to 1 mol per mole of water; and, a solubility in the liquid in supercritical state of 0.001 mol to 1 mol per mole of liquid in the supercritical state.

### Claim 7 (depends on 1)

The process as claimed in claim 1 wherein R1 represents in formula (Ia) represents —CH3 or isotridecyl and/or t represents a number from 8 to 10.

### Claim 8 (depends on 1)

The process as claimed in claim 1 wherein one or more than one R5 in formula (III) represents —OR1.

### Claim 9 (depends on 1)

The process as claimed in claim 1 wherein R6 in formula (IV) as attached to a terminal silicon atom represents R1 in each occurrence.

### Claim 10

A composition comprising
a) a product of formula (Ia) or formula (Ib) or a mixture thereof,
and
b) a product selected from a product of formula (II), a product of formula (III), a product of formula (IV), an α-aminocarboxylic acid, and a mixture thereof,
where
E represents hydrogen or R1,
R1 represents alkyl of 1 to 13 carbon atoms,
one of R2 and R3 represents —CH3 while the other represents H,
R4 represents H, —CH3, —CH2—CH3 or —CH2—OH,
R5 in each occurrence independently represents R1 or —OH or —OR1,
R6 in either occurrence independently represents R5 or R8,
R7 in each occurrence independently represents R1,
R8 in each occurrence independently represents a radical of formula (V) or of formula (VI),
R9 in each occurrence independently represents hydrogen or —CH3,
—X—NH2 (V)
—Y—NH—Z—NH2 (VI)
b represents 0 or 1 in the case of formula (Ia) and a number from 0 to 15 in the case of formula (Ib),
t represents a number from 5 to 14 and the b:t ratio represents a number from 0 to 0.2 in formula (Ia) and from 0 to 1.1 in formula (Ib),
k represents a number from 0 to 1000, and
X and Y each independently represent a linear or branched alkylene radical of 1 to 4 carbon atoms and Z represents a linear or branched alkylene radical of 2 to 4 carbon atoms.

### Claim 11 (depends on 10)

A solution comprising the composition of claim 10 dissolved in supercritical carbon dioxide.

### Claim 12

A reaction product obtained by reacting a product of formula (Ia) or formula (Ib) or a mixture thereof
with at least one product of formula (II) or (III),
where
E represents hydrogen or R1,
R1 represents alkyl of 1 to 13 carbon atoms,
one of R2 and R3 represents —CH3 while the other represents H,
R4 represents H, —CH3, —CH2—CH3 or —CH2—OH,
R5 in each occurrence independently represents R1 or —OH or —OR1,
R9 in each occurrence independently represents hydrogen or —CH3,
b represents 0 or 1 in the case of formula (Ia) and a number from 0 to 15 in the case of formula (Ib),
t represents a number from 5 to 14 and the b:t ratio represents a number from 0 to 0.2 in formula (Ia) and from 0 to 1.1 in formula (Ib).

### Claim 13 (depends on 12)

The reaction product as claimed in claim 12 wherein the reaction product is soluble in water and in supercritical carbon dioxide at not less than 0.0001 mol per mole of water/supercritical carbon dioxide.

### Claim 14

The reaction product as claimed in 13 wherein the reaction product has a solubility in water of 0.001 mol to 1 mol per mole of water and a solubility in supercritical carbon dioxide of 0.001 mol to 1 mol per mole of supercritical carbon dioxide.

### Claim 15 (depends on 12)

The reaction product as claimed in claim 12 wherein R1 in formula (Ia) represents —CH3 or isotridecyl and/or t represents a number from 8 to 10.

### Claim 16 (depends on 12)

The reaction product as claimed in claim 12 wherein one or more than one R5 in formula (III) represents —OR1.

### Claim 17 (depends on 12)

The reaction product as claimed in claim 12 wherein R6 in formula (IV) as attached to a terminal silicon atom represents R1 in each occurrence.

### Claim 18 (depends on 12)

A solution comprising the reaction product of claim 12 dissolved in supercritical carbon dioxide.