# US 11,078,366 B2 · Bis-azo colorants for use as bluing agents

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- Number: US 11,078,366 B2
- Document ID: US11078366B2
- Status: Granted
- Kind: B2
- Application number: 16/666,868
- Filed: 2019-10-29
- Published: 2020-02-27
- Granted: 2021-08-03
- Earliest claimed: 2016-01-29
- Assignees: Milliken & Company
- Applicants: Milliken & Company
- Inventors: Sanjeev K. Dey; Eduardo Torres; Gregory S. Miracle; Daniel D. Ditullio, Jr.
- Web page: https://patentgrep.com/patent/US11078366B2

## CPC

- C09B 31/053: Amino naphthalenes
- C09B 69/00: Dyes not provided for by a single group of this subclass
- C11D 3/40: Dyes {; Pigments}
- C11D 3/42: Brightening agents {; Blueing agents}
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.

## Claims

### Claim 1

A treated situs comprising:
(a) a textile substrate; and
(b) a bluing agent, wherein the bluing agent is comprised of: (i) at least one chromophore component that comprises a bis-azo colorant, and (ii) at least one polymeric component; wherein said chromophore and said polymeric component are covalently bound to one another and wherein the bluing agent is selected from the following structure:
and
mixtures thereof;
wherein R1 is a polyoxyalkylene chain having from 2 to 100 repeating units; R2 and R3 are independently selected from the group consisting of H, alkyl, alkoxy, alkyleneoxy, capped alkyleneoxy, polyalkyleneoxy and capped polyalkyleneoxy; R4 is selected from H, C(O)H and C(O)R5; wherein R5 is independently selected from the group consisting of C1-7 alkyl, C6-10 aryl, and C7-11 arylalkyl; wherein said capping groups are independently selected from C(O)R5 and R5; wherein the A ring may be further substituted with one or more groups selected from the group consisting of C1-8 alkyl, C1-8 alkoxy, nitro and OR6; wherein R6 is selected from the group consisting of H, hydroxyalkyl, a polyalkyleneoxy and a capped polyalkyleneoxy; wherein each M is independently selected from the group consisting of an alkali metal cation, an ammonium ion and an alkaline earth metal cation.

### Claim 2 (depends on 1)

A treated situs according to claim 1 in which in the bluing agent R2 and R3 are independently selected from the group consisting of H, alkyl, alkoxy, alkyleneoxy, and capped alkyleneoxy.

### Claim 3 (depends on 1)

A treated situs according to claim 1 in which in the bluing agent, R2 and R3 are independently selected from the group consisting of H, C1-4 alkyl, and C1-4 alkoxy.

### Claim 4 (depends on 1)

A treated situs according to claim 1 in which in the bluing agent, R1 is a polyoxyalkylene chain having from 4 to 50 repeating units.

### Claim 5 (depends on 1)

A treated situs according to claim 1, wherein the polyoxyalkylene chain comprises ethyleneoxide for at least 50% of the units.

### Claim 6 (depends on 1)

A treated situs according to claim 1 wherein the bluing agent's chromophore exhibits an absorbance spectrum maximum in water of from about 560 nanometers to about 640 nanometers.

### Claim 7 (depends on 1)

A treated situs according to claim 1 wherein the bluing agent exhibits an absolute hue angle in the range of 220° to 3200.

### Claim 8 (depends on 5)

A treated situs according to claim 5 wherein R2 is alkyl and R3 is selected from C1-4 alkyl and C1-4 alkoxy groups.

### Claim 9 (depends on 5)

A treated situs according to claim 5 wherein R2 and R3 are C1-4 alkoxy groups.

### Claim 10 (depends on 9)

A treated situs according to claim 9, wherein R4 is H or C(O)CH3.

### Claim 11 (depends on 10)

A treated situs according to claim 10, wherein R4 is H or C(O)CH3.

### Claim 12 (depends on 3)

A treated situs according to claim 3, wherein the A ring is substituted with another group selected from alkyl, alkoxy and OR1.

### Claim 13 (depends on 1)

A treated situs according to claim 1 wherein the bluing agent exhibits an absolute hue angle in the range of 240° to 310°.

### Claim 14 (depends on 1)

A treated situs according to claim 1 wherein the bluing agent exhibits an absolute hue angle in the range of 250° to 300°.

### Claim 15 (depends on 1)

A treated situs according to claim 1 wherein the textile substrate a fabric.

### Claim 16 (depends on 15)

A treated situs according to claim 15 wherein the fabric is comprised of fiber selected from the group consisting of cellulose, polyester, and polyamide.

### Claim 17 (depends on 16)

A treated situs according to claim 16 wherein cellulose is cotton.

### Claim 18 (depends on 16)

A treated situs according to claim 16 wherein polyamide is nylon.