# US 10,440,950 B2 · Methods of making triamine solids

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- Number: US 10,440,950 B2
- Document ID: US10440950B2
- Status: Granted
- Kind: B2
- Application number: 15/267,508
- Filed: 2016-09-16
- Published: 2017-03-23
- Granted: 2019-10-15
- Earliest claimed: 2015-09-17
- Assignees: Ecolab USA Inc.
- Applicants: Ecolab USA Inc.
- Inventors: Erik C. Olson; Carter M. Silvernail; Gregory G. Griese
- Web page: https://patentgrep.com/patent/US10440950B2

## CPC

- A01N 33/04: Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
- A01N 25/12: Powders or granules (A01N25/26 takes precedence)
- A01N 25/22: containing ingredients stabilising the active ingredients
- A01P 1/00: Disinfectants; Antimicrobial compounds or mixtures thereof
- C07C 209/00: Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C 209/68: from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C10M 105/00: Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M 105/58: Amines, e.g. polyalkylene polyamines, quaternary amines (polyalkylene polyamines with eleven or more monomer units C10M107/44)
- C11D 3/2082: {Polycarboxylic acids-salts thereof}
- C11D 3/48: Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
- C11D 7/265: {Carboxylic acids or salts thereof}
- C11D 7/3209: {Amines or imines with one to four nitrogen atoms; Quaternized amines}
- C10M 2215/041: used as base material
- C10N 2030/16: Antiseptic; {(micro)} biocidal {or bactericidal}
- C11D 2111/14: Hard surfaces
- C12Y 301/01003: Triacylglycerol lipase (3.1.1.3)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01P: BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C12Y: ENZYMES

## Abstract

Methods of making triamine solids are disclosed. Solids including free-flowing powders, to pressed, cast, extruded or other solids are disclosed. Compositions employing the solid triamines are provided and methods of use thereof are particularly suitable for cleaning, disinfecting, sanitizing, rinsing and/or lubricating are disclosed.

## Claims

### Claim 1

A method of making a solid triamine composition comprising:
mixing a triamine and an acid, wherein the acid is a monoacid and/or a diacid, wherein the triamine has the following formula:
wherein R is a straight chain C1-C12 alkyl group, and wherein the ratio of the acid to the triamine is from about 1:10 to about 1:1; and
at least partially neutralizing the triamine to a pH of about 6 to about 11 to form a solid amine salt;
wherein the method forms a solid composition at a temperature between about 70° F. (21° C.) and 130° F. (55° C.) without requiring casting, extrusion, or cooling step;
wherein the monoacid has the formula R—COOH,
wherein R is a branched or linear C4-C20 alkane or alkene, and wherein the diacid is selected from the group consisting of the structure of (a), (b), (c) and combinations thereof, as shown:
wherein:
n=1-20,
R1 is H, C1-C8 alkyl or COOH,
R2 is H, C1-C8 alkyl, NH2, OH, or COOH, and
R1 and R2 substitution occurs on at least one carbon within C1-C20 chain;
R1 and R2 are each COOH; R3, R4, R5 and R6 independently are H, C1-C8 alkyl, OH, or NH2
R1 and R3 are each COOH; R2, R4, R5 and R6 independently are H, C1-C8 alkyl, OH, or NH2
R1 and R4 are each COOH; R2, R3, R5 and R6 independently are H, C1-C8 alkyl, OH, or NH2
R1 and R5 are each COOH; R2, R3, R4 and R6 independently are H, C1-C8 alkyl, OH, or NH2 or
R1 and R6 are each COOH; R2, R3, R4 and R5 independently are H, C1-C8 alkyl, OH, or NH2;
R1 and R2 are each COOH; R3, R4, and R5 independently are H, C1-C8 alkyl, OH, or NH2:
R1 and R3 are each COOH; R2, R4, and R5 independently are H, C1-C8 alkyl, OH, or NH2
R1 and R4 are each COOH; R2, R3, and R5 independently are H, C1-C8 alkyl, OH, or NH2;
R1 and R5 are each COOH; R2, R3, and R4 independently are H, C1-C8 alkyl, OH, or NH2.

### Claim 2 (depends on 1)

The method of claim 1, wherein the concentration of the triamine is between about 10 and about 99 wt-% and the concentration of the acid is between about 1 and about 50 wt-%, and wherein the solid triamines remains solid at temperatures up to about 50° C.

### Claim 3 (depends on 1)

The method of claim 1, wherein the solid is a powder, paste or hardened solid and wherein the solid has a water content of less than about 10 wt-%.

### Claim 4 (depends on 1)

The method of claim 1, wherein the step of at least partially neutralizing the triamine neutralizes the pH to about 6.5 to about 9.5.

### Claim 5 (depends on 1)

The method of claim 1, wherein the step of at least partially neutralizing the triamine neutralizes the pH to about 7 to about 9.

### Claim 6 (depends on 1)

The method of claim 1, wherein the step of at least partially neutralizing the triamine occurs prior to solidification to stabilize the solid triamine.

### Claim 7 (depends on 1)

The method of claim 1, wherein the mixing occurs in a mixing vessel to provide a substantially homogenous mixture.

### Claim 8 (depends on 1)

The method of claim 1, wherein the mixing occurs in a continuous or batch process, and wherein the formation of the solid triamines occurs over a period from about 15 minutes to about 48 hours.

### Claim 9 (depends on 1)

The method of claim 1, wherein the ratio of the diacid to the biocidal triamine is from about 1:5 to about 1:1.

### Claim 10 (depends on 1)

The method of claim 1, wherein the solidification does not require a melt and/or conventional casting and/or extruding to compress the solid triamine through a die.

### Claim 11 (depends on 1)

The method of claim 1, wherein the monoacid and/or diacid is citric, tartaric, malic, maleic, malonic, succinic, adipic, aspartic, glutamic, dipicolinic, and/or dodecanoic acid.

### Claim 12 (depends on 1)

The method of claim 1, wherein no water is added to the reaction and/or a chelant is added to reduce the water content of the solid composition.

### Claim 13 (depends on 1)

A method of cleaning, sanitizing and/or disinfecting comprising:
generating a solid triamine according to claim 1; and
optionally adding additional functional ingredients to the solid triamine and/or forming a composition comprising the solid triamine and additional functional ingredients, and
contacting an article or surface with a use solution of the solid triamine and/or a use solution of the composition for cleaning, sanitizing, and/or disinfecting.

### Claim 14 (depends on 13)

The method of claim 13, wherein the cleaning, sanitizing, and/or disinfecting is a rinse step and/or lubricating step.

### Claim 15 (depends on 13)

The method of claim 13, wherein the use solution of the solid triamine and/or compositions comprising the solid triamines provides between about 1 ppm to about 1000 ppm triamine, and between about 1 ppm to about 500 ppm acid.