Odour-masked amine composition

Abstract

The present invention relates to a composition comprising: a) at least one primary, secondary or tertiary amine and b) at least one agent which masks the odor of said at least one amine, said at least one odor-masking agent comprising at least one ether (b1), optionally, but preferably, at least one terpene and/or one terpenoid (b2) and optionally, but preferably, at least one oxime (b3). The invention also relates to the use of an odor-masking agent in order to mask the odor of at least one amine.

Claims

1. A composition, comprising: (a) at least 90% by weight of at least one primary, secondary or tertiary amine represented by formula (I), relative to the total weight of the composition, ##STR00004## wherein R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, are selected independently of one another from a hydrogen atom, a linear or branched alkyl radical comprising from 1 to 12 carbon atoms, or a cycloalkyl radical comprising from 3 to 12 carbon atoms, or two of the substituents selected from R.sub.1, R.sub.2 and R.sub.3, together and with the nitrogen atom to which they are bonded, form a ring structure comprising from 2 to 12 carbon atoms, and optionally comprising one or more heteroatoms selected from oxygen, nitrogen, sulfur or phosphorus, and being optionally substituted with one or more functional groups selected from hydroxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, benzyl, fluorine, chlorine, bromine, iodine, sulfur, phosphorus or nitrogen, and at least one of is R.sub.1, R.sub.2 and R.sub.3 is not hydrogen; and (b) an odor-masking agent, wherein the composition comprises at most 10% by weight of the odor-masking agent, relative to the total weight of the composition; and the odor-masking agent comprises at least one ether represented by formula (b1):
R.sub.4OR.sub.5(b1) wherein R.sub.4 and R.sub.5, which may be identical or different, are selected independently of one another from a linear or branched alkyl radical comprising from 1 to 12 carbon atoms, a cycloalkyl radical comprising from 3 to 12 carbon atoms, an alkenyl radical comprising from 2 to 12 carbon atoms, a cycloalkenyl radical comprising from 3 to 12 carbon atoms, a phenyl radical or a benzyl radical, or R.sub.4 and R.sub.5, together and with the oxygen atom to which they are bonded, form a ring structure comprising from 3 to 20 atoms, optionally comprising one or more heteroatoms selected from oxygen, nitrogen, sulfur and phosphorus, wherein the ring structure is optionally substituted with one or more groups selected from hydroxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, phenyl, benzyl, fluorine, chlorine, bromine, iodine, sulfur, phosphorus or nitrogen.

2. The composition of claim 1, wherein the odor-masking agent further comprises: (b2) at least one terpene and/or one terpenoid.

3. The composition of claim 1, wherein the odor-masking agent further comprises: at least one oxime represented by formula (b3): ##STR00005## wherein R.sub.6 is selected from a linear or branched alkyl radical comprising from 1 to 24 carbon atoms, a cycloalkyl radical comprising from 3 to 24 carbon atoms, an alkenyl radical comprising from 2 to 24 carbon atoms, a cycloalkenyl radical comprising from 3 to 24 carbon atoms, a phenyl radical or a benzyl radical, and R.sub.7 is selected from a hydrogen atom, a linear or branched alkyl radical comprising from 1 to 24 carbon atoms, a cycloalkyl radical comprising from 3 to 24 carbon atoms, an alkenyl radical comprising from 2 to 24 carbon atoms, a cycloalkenyl radical comprising from 3 to 24 carbon atoms, a phenyl radical or a benzyl radical, or R.sub.6 and R.sub.7, together and with the carbon atom to which they are bonded, form a ring structure comprising from 3 to 20 atoms, and optionally comprising one or more heteroatoms selected from oxygen, nitrogen, sulfur or phosphorus, wherein the ring structure is optionally substituted with one or more groups selected from hydroxyl, alkoxy, phenyl, benzyl, fluorine, chlorine, bromine, iodine, sulfur, phosphorus or nitrogen.

4. The composition of claim 1, wherein the amine is a primary amine.

5. The composition of claim 1, wherein the amine is selected from the group consisting of propan-1-amine, propan-2-amine, cyclopentanamine, 2-methylpropan-2-amine, phenylmethanamine, 2-aminopentane, 3-aminopentane, 1,2-dimethylpropylamine, hexylamine, 1,3-dimethylbutylamine, n-heptylamine, n-octylamine, 2-aminooctane, 3,3,5-trimethylcyclohexylamine, ethylamine (MEA), isopropylamine, sec-butylamine, 3-ethoxypropylamine, 3-(2-methoxyethoxy)propylamine, 3-butoxypropylamine, 3-(2-ethylhexyloxy)propylamine, 3-isopropoxypropylamine, 3-methoxypropylamine, and mixtures thereof.

6. The composition of claim 1, wherein the amine is selected from the group consisting of N-methylethanamine, N-ethylethanamine, N-methylpentan-3-amine, N-3-dimethylbutan-2-amine, di(sec-butyl)amine, diamylamine, isopropylbenzylamine, dihexylamine, diethylamine, diisopropylamine, N-isopropylmethylamine, N-butylmethylamine, N-(sec-butyl)methylamine, N-isobutylmethylamine, N-(tert-butyl)methylamine, N-methylpentylamine, N-hexylmethylamine, N-methylcyclohexylamine, N-heptylmethylamine, N-octylmethylamine, N-ethylmethylamine, N-ethylpropylamine, N-ethylisopropylamine, N-butylethylamine, N-(sec-butyl)ethylamine, N-ethylcyclohexylamine, N-ethylbenzylamine, and mixtures thereof.

7. The composition of claim 1, wherein the amine is selected from the group consisting of trimethylamine, N-methylaziridine, dimethylethylamine (DMEA), N-methylazetidine, N-ethylaziridine, diethylmethylamine (DEMA), dimethylisopropylamine (DMIPA), dimethyl(n-propyl)amine (DMPA), N-(n-propyl)aziridine, N-isopropylaziridine, N-ethylazetidine, N-methylpyrrolidine, N,N,N,N-tetramethyldiaminomethane, triethylamine (TEA), methylethyl(n-propyl)amine, methylethylisopropylamine, dimethyl(n-butyl)amine, dimethyl(sec-butyl)amine, dimethylisobutylamine, dimethyl(tert-butyl)amine, N-ethylpyrrolidine, N-methylpiperidine, hexamethylenetetramine, dimethylpiperazine, N,N,N,N-tetramethyldiaminoethane, dimethylpentylamines, methylethylbutylamines, diethylamines, dipropylmethylamines, N-propylpyrrolidines, N-ethylpiperidine, dimethylhexylamines, methylethylpentylamines, diethylbutylamines, dipropylethylamines, N-butylpyrrolidines, N-propylpiperidines, diethylpiperazine, dimethylheptylamines, methylethylhexylamines, diethylpentylamines, tripropylamines, N-pentylpyrrolidines, N-butylpiperidines, dimethyloctylamines, methylethylheptylamines, diethylhexylamines, ethylpropylpentylamines, dipropylbutylamines, N-pentylpiperidines, ethyldiisopropylamine, and mixtures thereof.

8. The composition of claim 1, wherein the amine is selected from the group consisting of DMEA, DMIPA, DEMA, DMPA, TEA, and mixtures thereof.

9. The composition of claim 1, wherein the amine comprises DMEA.

10. The composition of claim 1, wherein the ether represented formula (b1) is selected from the group consisting of phenoxybenzene, diphenyl ether, methoxynaphthalenes, 1-methoxy-4-methyl-(4-methylanisole), 2-(2,4-dimethylcyclohex-3-en-1-yl)-5-methyl-(1-methylpropyl)-1,3-dioxane, methoxymethane, methoxyethane, ethoxyethane, 2-ethoxypropane, oxacyclopropane, oxacyclopentane, oxacyclohexane, 1,4-dioxacyclohexane, dimethoxymethane, diisopropyl ether, tetrahydrofuran, 1,4-dioxane, pyrans, dihydropyrans, phenylpyrans, dihydrophenylpyrans, pyrans and dihydropyrans substituted by at least one of a phenyl or an alkyl group, and mixtures thereof.

11. The composition of claim 1, wherein the odor-masking agent further comprises: (b2) at least one terpene/terpenoid selected from the group consisting of terpinenes, myrcene, limonene, terpinolene, pinenes, sabinene, camphene, ocimene, eucalyptol, citral, menthol, camphor, menthone, terpineol, isoborneol, nerol, citronellal, citronellol, linalool, geraniol, myrcenol, essential oils based on terpenes and/or terpenoids, and mixtures thereof.

12. The composition of claim 1, wherein the odor-masking agent further comprises (b3) at least one oxime selected from the group consisting of cinnamaldehyde oxime, 2-methylbutanal oxime, 3-methylbutanal oxime, methyl ethyl ketoxime, 3-heptanone oxime, 5-methyl-3-heptanone oxime, glyoxime, dimethylglyoxime, diaminoglyoxime, pralidoxime, obidoxime, perillartine, asoxime chloride, salicylaldoxime, and mixtures thereof.

13. The composition of claim 1, wherein the odor-masking agent further comprises: (b2) at least one terpene/terpenoid, and (b3) at least one oxime.

14. The composition of claim 1, wherein the amine is a secondary amine.

15. The composition of claim 1, wherein the amine is a tertiary amine.

16. The composition of claim 1, comprising at least 95% by weight of (a) and at most 5% by weight of (b), relative to the total weight of the composition.

17. The composition of claim 1, comprising at least 99% by weight of (a) and at most 1% by weight of (b), relative to the total weight of the composition.

18. The composition of claim 1, comprising at least 99.5% by weight of (a) and at most 0.5% by weight of (b), relative to the total weight of the composition.

19. A method of preparing the composition of claim 1, comprising combining (a) and (b).

20. A method of manufacturing a polymer, comprising manufacturing a polymer in the presence of the composition of claim 1.

21. A method of manufacturing a foundry mold, comprising manufacturing a foundry mold in the presence of the composition of claim 1.

22. A foundry mold obtained by crosslinking a binder mixed with an aggregate in the presence of the composition of claim 1.

23. A method of masking the odor of a secondary or tertiary amine, comprising combining at least one secondary or tertiary amine with an effective amount of an odor-masking agent comprising: at least one ether represented by formula (b1):
R.sub.4OR.sub.5(b1) wherein R.sub.4 and R.sub.5, which may be identical or different, are selected independently of one another from a linear or branched alkyl radical comprising from 1 to 12 carbon atoms, a cycloalkyl radical comprising from 3 to 12 carbon atoms, an alkenyl radical comprising from 2 to 12 carbon atoms, a cycloalkenyl radical comprising from 3 to 12 carbon atoms, a phenyl radical or a benzyl radical, or R.sub.4 and R.sub.5, together and with the oxygen atom to which they are bonded, form a ring structure comprising from 3 to 20 atoms, optionally comprising one or more heteroatoms selected from oxygen, nitrogen, sulfur and phosphorus, wherein the ring structure is optionally substituted with one or more groups selected from hydroxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, phenyl, benzyl, fluorine, chlorine, bromine, iodine, sulfur, phosphorus or nitrogen, and at least one oxime represented by formula (b3): ##STR00006## wherein R.sub.6 is selected from a linear or branched alkyl radical comprising from 1 to 24 carbon atoms, a cycloalkyl radical comprising from 3 to 24 carbon atoms, an alkenyl radical comprising from 2 to 24 carbon atoms, a cycloalkenyl radical comprising from 3 to 24 carbon atoms, a phenyl radical or a benzyl radical, and R.sub.7 is selected from a hydrogen atom, a linear or branched alkyl radical comprising from 1 to 24 carbon atoms, a cycloalkyl radical comprising from 3 to 24 carbon atoms, an alkenyl radical comprising from 2 to 24 carbon atoms, a cycloalkenyl radical comprising from 3 to 24 carbon atoms, a phenyl radical or a benzyl radical, or R.sub.6 and R.sub.7, together and with the carbon atom to which they are bonded, form a ring structure comprising from 3 to 20 atoms, and optionally comprising one or more heteroatoms selected from oxygen, nitrogen, sulfur or phosphorus, wherein the ring structure is optionally substituted with one or more groups selected from hydroxyl, alkoxy, phenyl, benzyl, fluorine, chlorine, bromine, iodine, sulfur, phosphorus or nitrogen.

Description

EXAMPLES

Example 1: Composition Based on Odor-Masked Tertiary Amine

(1) In order to characterize a perfuming composition which may serve as masking agent, i.e. which makes it possible to improve, reduce or eliminate the odor of a tertiary amine, an olfactory test procedure and an examination of stability were developed.

(2) Operating Conditions:

(3) In order to carry out this olfactory test, an amount of 1 ml of composition (amine and odor-masking agent) is placed in a container. The container containing the composition is then placed in a 10 liter dessicator.

(4) The dessicator is left in the open air at room temperature (25 C.). After total evaporation (approximately 30 minutes), a panel composed of 10 people inhale the composition in order to grade the odor (hedonic test).

(5) When the panelists have smelt the compositions, they note the odor of the composition. Depending on their preference, they allocate one or more crosses to each of the compositions to be tested. The number of crosses given by the panelists ranges from 1 (most unpleasant product) to 3 (most pleasant product).

(6) For the examination of stability, the compositions are stored at room temperature (25 C.) for a duration ranging from 1 month to more than 1 year.

(7) Preparation of Test Specimens:

(8) Each composition is prepared with a tertiary amine, dimethylethylamine (DMEA) provided by Arkema. The DMEA has a purity of greater than or equal to 99%.

(9) A reference sample is produced with pure DMEA and is named A1. Three samples comprising 99.92% by weight relative to the total weight of the DMEA sample and 0.08% by weight relative to the total weight of the sample of a perfuming composition are also prepared. The samples are named: A.sub.2, A.sub.3 and A.sub.4.

(10) The nature of the masking agent of each of the samples A.sub.2, A.sub.3 and A.sub.4 is given below, in which the percentages are expressed by weight relative to the total weight of the masking agent:

(11) Sample A.sub.2 (Comparative Test): Odor-Masking Agent: OMA-A2

(12) 30% to 70% esters (2-tert-butylcyclohexyl acetate, 3-methylbutyl butyrate, 2-propylene-3-cyclohexyl propanoate, 4-undecanolide, isopentyl acetate),

(13) 15% to 35% ketones (5-methyl-3-heptanone, 1-cyclooct-3-enylethanone),

(14) 15% to 35% ethers (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylindeno[5,6-c]pyran),

(15) in which the sum of the constituents represents 100% by weight of the masking agent.

(16) Sample A.sub.3 (Comparative Test): Odor-Masking Agent: OMA-A3

(17) 30% to 50% esters (3a,4,5,6,7,7a-hexahydro-4,7-methano-1-inden-5(6)-yl acetate, methyl benzoate, 2-acetyl-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene),

(18) 30% to 50% ketones and aldehydes (3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, 2-methylundecanal, heptan-2-one, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one, 3-phenyl-2-propenal, 3-phenylbutanal),

(19) 1% to 10% alcohols (3,7-dimethyloctan-3-ol, 3,7-dimethyl-2,6-octadien-1-ol),

(20) 1% to 10% ethers (2-methoxynaphthalene),

(21) in which the sum of the constituents represents 100% by weight of the masking agent.

(22) Sample A.sub.4 (According to the Invention): Odor-Masking Agent: OMA-B1

(23) 10% to 98% ethers (phenoxybenzene, 2-methoxynaphthalene),

(24) from 10% to 98% terpenes/terpenoids (limonene, eucalyptol),

(25) from 1% to 10% oximes (5-methyl-3-heptanone oxime),

(26) from 0.1% to 1% additives, mainly esters (triethyl citrate, isopropyl tetradecanoate),

(27) in which the sum of the constituents represents 100% by weight of the masking agent.

(28) Results:

(29) The results of example 1 are reproduced in the following table 1:

(30) TABLE-US-00001 TABLE 1 Storage stability Sample to be tested Odor (at room temperature) A.sub.1 + Colorless, stable (more than one year) A.sub.2 ++ Yellow (after 1 month), unstable A.sub.3 ++ Yellow (after 1 month), unstable A.sub.4 ++++ Colorless, stable (after 3 months)

(31) In example 1 of the present invention, the perception of the odor of the composition according to the invention A.sub.4 is considerably more pleasant than in samples A.sub.1, A.sub.2 and A.sub.3.

(32) Moreover, sample A.sub.4 remains colorless and stable after 3 months of storage at room temperature, whereas samples A.sub.2 and A.sub.3, which are unstable, become yellow in color after 1 month of storage at room temperature.

Example 2: Composition Based on Odor-Masked Tertiary Amine According to the Invention

(33) The operating procedure of example 1 is reproduced in order to prepare two new samples A.sub.5 and A.sub.6, which differ from sample A.sub.4 in terms of the content of masking agent, as indicated below:

(34) Sample A.sub.4 (According to the Invention):

(35) DMEA: 99.92% by weight relative to the total weight of the sample, and odor-masking agent OMA-B1: 0.08% by weight relative to the total weight of the sample.
Sample A.sub.5 (According to the Invention):

(36) DMEA: 99.86% by weight relative to the total weight of the sample, and

(37) odor-masking agent OMA-B1: 0.14% by weight relative to the total weight of the sample.

(38) Sample A.sub.6 (According to the Invention):

(39) DMEA: 99.75% by weight relative to the total weight of the sample, and

(40) odor-masking agent OMA-B1: 0.25% by weight relative to the total weight of the sample.

(41) Results:

(42) The results of example 2 are reproduced in the following table 2:

(43) TABLE-US-00002 TABLE 2 Storage stability Sample to be tested Odor (at room temperature) A.sub.1 + Colorless, stable (more than one year) A.sub.4 ++++ Colorless, stable (after 3 months) A.sub.5 ++++ Colorless, stable (after 3 months) A.sub.6 ++ Colorless, stable (after 3 months)

(44) The results from table 2 show that the perception of the odor of the compositions according to the invention A.sub.4, A.sub.5 and A.sub.6 is considerably more pleasant than in sample A.sub.1, and that the increase in the dose of odor-masking agent leads to a slight decrease in the pleasant olfactory perception of the composition.

(45) Moreover, samples A.sub.4, A.sub.5 and A.sub.6 remain colorless and stable after 3 months of storage at room temperature, irrespective of the amount of masking agent incorporated into the DMEA.