EP-4735564-A1 - TREATMENT COMPOSITIONS WITH ESTERAMINES OR SALTS THEREOF

EP4735564A1EP 4735564 A1EP4735564 A1EP 4735564A1EP-4735564-A1

Abstract

A treatment composition that includes at least one perfume raw material and an esteramine or salt thereof, the esteramine or salt thereof may be obtained by a process of using catalytic amounts of at least one orthoester; and methods of treating an article or a surface, wherein the method comprises treating the article or surface with such treatment composition, optionally in the presence of water.

Inventors

MCDERMOTT, WILLIAM PETER, III
ORLANDINI, LAURA
NATOLI, SEAN N.
PANANDIKER, RAJAN, KESHAV
EBERT, SOPHIA ROSA
DEL REGNO, ANNALAURA
TRUJILLO, RAFAEL

Assignees

The Procter & Gamble Company

Dates

Publication Date: 20260506
Application Date: 20240627

Claims (15)

1. A treatment composition comprising at least one perfume raw material and an esteramine of Formula (I) or salt thereof, (Formula I) wherein independently from each other: t being an integer from 1 to 100; Ai is independently for each repetition unit t selected from the list consisting of ethyleneoxy group, 1,2-propyleneoxy group, 1,2-butyleneoxy group, 2, 3 -butyleneoxy group, i-butyleneoxy group, pentyleneoxy group, hexyleneoxy group, styryloxy group, decenyloxy group, dodecenyloxy group, tetradecenyloxy group, and hexadecanyloxy group, wherein for t equal to 1 the oxygen atom of the Ai group is bound to the B group and the following Ai group is always bound via the oxygen atom to the previous Ai group; Bi is independently from each other selected from the group consisting of a bond, linear Ci to C12 alkanediyl groups, and branched Ci to C12 alkanediyl groups; R4, Rs, and R12 being selected from the group consisting of H, linear alkyl, branched alkyl, and cycloalkyl; with the provisio that Zi is selected from the group consisting of alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, and a compound according to Formula (II), wherein said compound according to Formula (II) connects to the compound according to Formula (I) via the bond labeled with *, with the provisio of at least one group R4, Rs, and/or R12 containing at least 7 or more carbon atoms; (Formula II) with independently from each other w being an integer from 0 to 12; R13 and R14 independently for each repetition unit w being selected from the group consisting of H, linear alkyl, branched alkyl, and cycloalkyl; R15, Ri6, R17, and Ris being selected from the group consisting of H, linear alkyl, branched alkyl, and cycloalkyl.
2. The treatment composition of Claim 1, comprising the salt of the esteramine, wherein the salt is formed by at least partial protonation of the amine group by an acid being a protic organic or inorganic acid.
3. The treatment composition of Claims 1 or 2, wherein the salt is formed by at least partial protonation of the amine group by an acid being selected from the group consisting of methanesulfonic acid, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, citric acid and lactic acid.
4. The treatment composition according to any preceding claim, wherein Ai is independently for each repetition unit t selected from the list consisting of ethyleneoxy group, 1,2-propyleneoxy group, and 1,2-butyleneoxy group.
5. The treatment composition according to any preceding claim, wherein Zi is selected from the group consisting of alanine, glycine, lysine, and a compound according to Formula (II), wherein w is an integer in the range of from 1 to 4, and wherein the compound according to Formula (II) connects to the compound according to Formula (I) via the bond labeled with *, with the provisio of at least one group R4, Rs, and/or R12 containing at least 7 or more carbon atoms.
6. A treatment composition comprising at least one perfume raw material and an esteramine or salt thereof, the esteramine or salt thereof obtained by a process of using catalytic amounts of at least one orthoester, the process comprising the steps of: a) reaction of: i) at least one amino acid selected from alpha-, beta-, gamma-, delta-, epsilon- etc. amino acids, such as alanine, glycine, leucine, isoleucine, valine, proline, phenylalanine, arginine, asparagine, aspartic acid, aspartate, glutamine, glutamate, histidine, lysine, threonine, tryptophan, tyrosine, cysteine, methionine, serine; alphaamino acids with secondary or tertiary amino groups such as sarcosine, N,N- dimethylglycine; other amino acids such as 6-aminohexanoic acid, 4-aminobutanoic acid, 3 -aminopropanoic acid, 12-aminododecanoic acid, 11-aminoundecanoic acid; amino acids formally derived from the hydrolysis of a-lactam (three ring atoms), P- lactam (four ring atoms), y-lactam (five ring atoms) and so on; such lactams preferably being P-propiolactam, g-butyrolactam, 5-valerolactam, g-valerolactam, e-caprolactam, d-decalactam, g-decalactam, e-decalactam; preferably alanine, valine, beta-alanine, 6- amino hexanoic acid; with ii) at least one alcohol (A) bearing at least one hydroxy group, being selected from mono-, di- and polyols, all of which may be optionally alkoxylated, wherein the alkoxylation of the at least one hydroxy group takes place in a step before step a), with the alcohol being alkoxylated with at least one alkylene oxide, preferably at least 1 and up to 200, preferably 1 to 100, more preferably up to 50 moles alkylene oxide per hydroxy group; in presence of iii) at least one acid (C), being selected from inorganic and organic acids, wherein said organic or inorganic acid has preferably a pKa value in the range of from -3 and up to +5, more preferably from -2,5 to 1,5, preferably at least one organic acid, such as sulfonic acids, more preferably alkylsulfonic acid and/or arylsulfonic acid; and iv) in the presence of at least one orthoester, such as triethyl orthoformate, trimethyl orthoformate, triethyl orthoacetate, trimethyl orthoacetate, and the like; whereas the orthoester is used in sub-stoichiometric amounts, preferably catalytic amounts (referred to the amino acid); and whereas the alcohol used for the esterification is different from the alcohol-residual in the orthoester; to produce an esteramine salt; b) optional neutralization of the obtained esteramine salt with at least one base to obtain the free esteramine; wherein the treatment composition comprises, by weight of the total composition, less than 0.5% of alcohol (A) as a residual of the reaction process which was used to obtain the esteramine or salt thereof.
7. The treatment composition according to claim 6, wherein the alcohol (A) is selected from: a. mono-alcohols such as Cl- to C36-alkanols, selected from the groups non-alkoxylated linear C2- to C36-alcohols, such as mixture of such alcohols selected from C6- to C22-fatty alcohols, preferably C8- to C22-fatty alcohols, more preferably C12- and C14-fatty alcohols, most preferably C16- and C18-fatty alcohols; non-alkoxylated branched C3- to C36-alcohols such as 2-ethylhexanol, 2-propylheptanol, isotri decanol, isononanol, C9-C17 oxoalcohols; alkoxylated linear C2- to C36-alcohols such as alkoxylated mixture of C6- to C22-fatty alcohols, preferably alkoxylated mixtures of C8- to C22-fatty alcohols, more preferably alkoxylated mixtures of C12- and C14-fatty alcohols, most preferably alkoxylated mixtures of Cl 6- and C18-fatty alcohols; alkoxylated branched C3- to C36-alcohols such as alkoxylated 2-ethylhexanol, alkoxylated 2-propylheptanol, alkoxylated isotridecanol, alkoxylated isononanol, alkoxylated C9-C17 oxoalcohols; b. di-alcohols such als alkane diols, polyalkoxylated C2-C6-alkanediols bearing at least two hydroxy groups, c. oligo-alcohols such as polyalkoxylated C3-C6-alkanetriols, bearing at least three hydroxy groups, d. polyols such as sugar alcohols, polyalkoxylated C5-C6-alkane polyols, glycerols such as diglycerol, triglycerol polyglycerol, dipentaerythritol, tripentaerythritol; and/or e. phenoxy alkanols such as phenoxyethanol; with the alcohol(s) selected from the groups of mono-alcohols and alkoxylated di-, oligoalcohols and alkoxylated polyols being preferred, and the alcohols selected from the group(s) mono-alcohols and alkoxylated di -alcohols being even more preferred.
8. The treatment composition according to claims 6-7, wherein the alcohol (A) employed is an alkoxylated alcohol which is obtained by alkoxylating at least one hydroxy group of the alcohol according to Claim 2 with one or more alkylene oxides to produce alkylene oxy-chains comprising one or more moieties stemming from alkylene oxides selected from C2 to C22- alkylene oxides, preferably C2-C4-alkylene oxides, whereas the moieties stemming from the alkylene oxide(s) may be arranged in random, block or multiblock-order or combinations thereof, preferably as block, more preferably contains only one block consisting of ethylene oxide or consisting of two blocks with the first block - preferably the “inner block” directly linked to the hydroxy group of the alcohol - consisting of ethylene oxide and a second block - preferably being the “outer block linked to the ethylene oxide-block - consisting of propylene oxide, such di-block even more preferably consisting of 3 to 10 EO-derived moieties and the PO-block consisting of 1 to 10 PO-derived moieties.
9. The treatment composition according to claims 6-8, wherein the acid (C) is selected from: i) alkyl sulfonic acids, such as methanesulfonic acid, ethylsulfonic acid, propylsulfonic acid, camphorsulfonic acid; alkylarylsulfonic acids and specifically alkylbenzenesulfonic acids, such as toluenesulfonic acid (including the mixture of isomers thereof), p-toluenesulfonic acid, o- toluenesulfonic acid, m-toluenesulfonic acid, xylenesulfonic acid (mixture of isomers), 2, 6- dimethylbenzenesulfonic acid, 2, 5-dimethylbenzenesulfonic acid, 2, 4-dimethylbenzenesulfonic acid, 4-dodecylbenzenesulfonic acid, iso-propyl benzenesulfonic acid, ethylbenzenesulfonic acid, and naphthalenesulfonic acid, preferably p-toluenesulfonic acid and methanesulfonic acid, more preferably methanesulfonic acid; ii) inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid; preferably selected from group i).
10. The treatment composition according to claims 6-9, wherein the acid (C) is chosen such that the esteramine is obtained as salt in cationic form, preferably the acid chosen is methanesulfonic acid and the esteramine obtained is a salt in cationic form.
11. The treatment composition according to claims 6-10, wherein the molar ratio of amino acid to hydroxyl group of the (optionally alkoxylated) alcohol is (0.8*n) : 1 to (l*n) : 1.5, with the number of hydroxy groups of the (optionally alkoxylated) alcohol being n.
12. The treatment composition according to claims 6-11, wherein the process is carried out with the molar ratio of the acid ( C ) to the amino acid is in the range of from 0.8 : 1 to 1 : 1.2.
13. The treatment composition according to claims 6-12, wherein in the process the reaction is performed: a. at a temperature of from 50 to 200°C, preferably 70- 180°C, more preferably 80°C- 160°C, most preferably 120°C - 150°C, such as 60, 65, 75, 85, 90, 95, 100, 110, 115, 120, 125, 130, 135, 140, 145, 155, 165, 170, 190 °C; b. for a period of from 1 to 30, preferably from 2, more preferably from 3 hours, even more preferably at least 5 hours, and preferably up to 48, more preferably up to 20, even more preferably up to 15 hours, such as preferably 3 to 24, more preferably 5 to 24, most preferably 10 - 24 hour(s); and C. at from 0,001 to 10 bar pressure, such as from 0,001, more preferably from 0,005, even more preferably from 0,1, and preferably up to 8, more preferably up to 5, even more preferably up to 4 bar, such as 1 to 10, more preferably 1 to 5, even more preferably 1 to 4 bar, or such as 1 to 1000 mbar, more preferably 100 to 500 mbar.
14. The treatment composition according to claims 6-13, wherein in the process the solvents for the reaction are selected from water, toluene, xylene, heptanol, cyclohexene, and the like, preferably only being water.
15. The treatment composition according to claims 6-14, wherein during or following the reaction, preferably at least during the reaction, water and/or excess alcohol are removed, such removal preferably being carried out by application of a stream of gas such as using gas such as inert gas as nitrogen or argon, preferably nitrogen, or steam made from water, preferably using inert gas, more preferably nitrogen, and/or applying a distillation method, preferably a distillation, more preferably a distillation method under reduced pressure and/or at elevated temperature, preferably both, a more preferred method being the use of an apparatus such as a Dean-Stark-trap, most preferably using a Dean-Stark-trap, such removal more preferably carried out applying a vacuum in the range of from 0.1 mbar to 800 mbar, preferably of from 1 mbar to 500 mbar and more preferably of from 10 mbar to 100 mbar, and using elevated temperatures.

Description

TREATMENT COMPOSITIONS WITH ESTERAMINES OR SALTS THEREOF FIELD OF THE INVENTION The present disclosure relates to treatment compositions that include at least one perfume raw material and esteramines or salts thereof; and methods of treating an article or surface by using such compositions. The esteramines may be obtained with a process that employs a catalytic or a sub-stoichiometric amount of an orthoester. BACKGROUND OF THE INVENTION Consumers prefer treatment products (e.g., fabric treatment compositions, hard surface treatment compositions, etc.) that have a noticeably pleasant smell. The consumer products industry is continuously seeking ways to improve the delivery efficiency and/or performance benefits associated with the perfume raw materials contained in such treatment compositions. The use of perfume delivery systems (e.g., a pro-perfume) can be a useful strategy to improve delivery efficiency. Accordingly, there is continued interest in new and improved perfume delivery systems for use in treatment compositions. Moreover, due to increasing environmental concerns, consumers want products that are associated with desirable environmental or sustainability profiles. Accordingly, some important targets of the consumer products industry are to utilize more biodegradable ingredients, improve the sustainability of the cleaning formulations, avoid the accumulation of non-degradable compounds in the ecosystem, and lower CO2 emissions associated with making or using the consumer product. Hence, there is a continuing need to provide consumer products that are more environmentally friendly but don’t sacrifice performance. In combination, there is a continuing need for treatment compositions that include perfume delivery systems that enable good/increased perfume delivery performance along with possessing increased environmentally friendliness. There is also a continuing need for methods of treating an article or surface by using such treatment compositions. SUMMARY OF THE INVENTION The present disclosure relates to treatment compositions that include at least one perfume raw material and an esteramine of Formula (I) or salt thereof, (Formula I) wherein independently from each other: t being an integer from 1 to 100; Ai is independently for each repetition unit t selected from the list consisting of ethyleneoxy group, 1,2-propyleneoxy group, 1,2-butyleneoxy group, 2, 3 -butyleneoxy group, i-butyleneoxy group, pentyleneoxy group, hexyleneoxy group, styryloxy group, decenyloxy group, dodecenyloxy group, tetradecenyloxy group, and hexadecanyloxy group, wherein for t equal to 1 the oxygen atom of the Ai group is bound to the B group and the following Ai group is always bound via the oxygen atom to the previous Ai group; Bi is independently from each other selected from the group consisting of a bond, linear Ci to C12 alkanediyl groups, and branched Ci to C12 alkanediyl groups; R4, Rs, and R12 being selected from the group consisting of H, linear alkyl, branched alkyl, and cycloalkyl; with the provisio that Zi is selected from the group consisting of alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, and a compound according to Formula (II), wherein said compound according to Formula (II) connects to the compound according to Formula (I) via the bond labeled with *, with the provisio of at least one group R4, Rs, and/or R12 containing at least 7 or more carbon atoms; with independently from each other w being an integer from 0 to 12; R13 and Rw independently for each repetition unit w being selected from the group consisting of H, linear alkyl, branched alkyl, and cycloalkyl; Ris, Ri6, R17, and Ris being selected from the group consisting of H, linear alkyl, branched alkyl, and cycloalkyl. The present disclosure also relates to treatment compositions that include at least one perfume raw material and an esteramine or salt thereof, the esteramine or salt thereof obtained by a process of using catalytic amounts of at least one orthoester, the process comprising the steps of: a reaction of: 1) at least one amino acid selected from alpha-, beta-, gamma-, delta-, epsilon- etc. amino acids, such as alanine, glycine, leucine, isoleucine, valine, proline, phenylalanine, arginine, asparagine, aspartic acid, aspartate, glutamine, glutamate, histidine, lysine, threonine, tryptophan, tyrosine, cysteine, methionine, serine; alpha-amino acids with secondary or tertiary amino groups such as sarcosine, N,N-dimethylglycine; other amino acids such as 6- aminohexanoic acid, 4-aminobutanoic acid, 3 -aminopropanoic acid, 12-aminododecanoic acid, 11-aminoundecanoic acid; amino acids formally derived from the hydrolysis of a-lactam (three ring atoms), P-lactam (four ring atoms), y-lactam (five ring atoms) and so on; such lactams preferably being P-propiolactam, g-butyrolactam, 5- val