Antimicrobial Acids and Salts
First Claim
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1. A method of achieving an antimicrobial, preservative and/or microorganism adhesion inhibiting effect for the protection within or on the surface of an article and/or material which method comprises applying an acid compound, acid compound mixture or acid composition comprising,an acid of the formula I, wherein R1=a linear or branched C1-C7-alky;
- Q represents a linear or branched C1-C10-alkyl moiety substituted with 1-3 functional groups independently selected from the group consisting of COOH, P(O)(OH)2 and S(O)2(OH) which are attached via a C-atom to said moiety;
m represents an integer from 1 to about 20;
o represents an integer from 0 to 15; and
the acid preferably has a polydispersity of up to about 3 and a weight-average molecular weight of 600 to about 3000;
an acid of the general formula II,wherein R1=methyl Q represents a linear or branched C1-C10-alkyl moiety substituted with 1-3 functional groups independently selected from the group consisting of COOH, P(O)(OH)2 and S(O)2(OH) which are attached via a C-atom to said moiety; and
n represents an integer from 0 to 15;
and/or an acid of the formula III,wherein;
R1=methyl Q represents a linear or branched C1-C10-alkyl moiety substituted with 1-3 functional groups independently selected from the group consisting of COOH, P(O)(OH)2 and S(O)2(OH) which are attached via a C-atom to said moiety;
p represents an integer from 1 to about 20;
q represents an integer from 1 to about 20;
r represents an integer from 0 to 15; and
the acid preferably has a polydispersity of up to about 3 and a weight-average molecular weight of 600 to about 3000;
to an article and/or material in order to achieve an antimicrobial, preservative and/or microorganism adhesion inhibiting effect for the protection of said article and/or material;
with the proviso that, if the acid compound, acid compound mixture or acid composition used is one comprising only one or more acids of the formula III wherein Q is selected solely from the group consisting of linear or branched C1-C10-alkyl moieties substituted with two functional COON groups attached via a C-atom to said moiety, the method either is limited to a method for achieving an antimicrobial and/or a preservative effect, or, the method is limited to coating or impregnation of materials comprising synthetic polymers or polymer precursors or monomeric compounds, or of articles made from such materials or to the bulk addition to a material or an article;
or in addition to one or more acids of the formula III at least another acid compound comprising an acid of the formula I as defined above, an acid of the formula II as defined above; and
/or at least one acid compound comprising an additional different acid of the formula III as mentioned above wherein at least one moiety Q is present which is a linear or branched C1-C10-alkyl moiety substituted with 1 to 3 COOH, P(O)(OH)2 and/or S(O)2(OH) groups, with the proviso that in the case of a compound of the formula III said moiety Q does not carry only 2 COOH groups, is applied in addition;
and wherein an acid of the formula I, II and/or III the mentioned COOH, P(O)(OH)2 and S(O)2(OH) groups may also be partially or completely present in negatively charged form, so that the acids of the formula I, II and/or Ill may also be partially or completely be present as salts.
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Abstract
The invention relates to novel acidic siloxane derivatives, the use, methods of use or processes making use of siloxane derivatives of this type, especially to achieve an anti-microbial, preservative and/or antiadhesive effect, for the protection of articles and/or materials, and a process for the manufacture of the novel compounds. The siloxane acids (which may also be in salt form) have the formula (I), formula (II) and/or formula (III), wherein the symbols have the meanings given in the specification.
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Citations
21 Claims
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1. A method of achieving an antimicrobial, preservative and/or microorganism adhesion inhibiting effect for the protection within or on the surface of an article and/or material which method comprises applying an acid compound, acid compound mixture or acid composition comprising,
an acid of the formula I, wherein R1=a linear or branched C1-C7-alky; -
Q represents a linear or branched C1-C10-alkyl moiety substituted with 1-3 functional groups independently selected from the group consisting of COOH, P(O)(OH)2 and S(O)2(OH) which are attached via a C-atom to said moiety; m represents an integer from 1 to about 20; o represents an integer from 0 to 15; and the acid preferably has a polydispersity of up to about 3 and a weight-average molecular weight of 600 to about 3000; an acid of the general formula II, wherein R1=methyl Q represents a linear or branched C1-C10-alkyl moiety substituted with 1-3 functional groups independently selected from the group consisting of COOH, P(O)(OH)2 and S(O)2(OH) which are attached via a C-atom to said moiety; and n represents an integer from 0 to 15; and/or an acid of the formula III, wherein; R1=methyl Q represents a linear or branched C1-C10-alkyl moiety substituted with 1-3 functional groups independently selected from the group consisting of COOH, P(O)(OH)2 and S(O)2(OH) which are attached via a C-atom to said moiety; p represents an integer from 1 to about 20; q represents an integer from 1 to about 20; r represents an integer from 0 to 15; and the acid preferably has a polydispersity of up to about 3 and a weight-average molecular weight of 600 to about 3000; to an article and/or material in order to achieve an antimicrobial, preservative and/or microorganism adhesion inhibiting effect for the protection of said article and/or material; with the proviso that, if the acid compound, acid compound mixture or acid composition used is one comprising only one or more acids of the formula III wherein Q is selected solely from the group consisting of linear or branched C1-C10-alkyl moieties substituted with two functional COON groups attached via a C-atom to said moiety, the method either is limited to a method for achieving an antimicrobial and/or a preservative effect, or, the method is limited to coating or impregnation of materials comprising synthetic polymers or polymer precursors or monomeric compounds, or of articles made from such materials or to the bulk addition to a material or an article;
or in addition to one or more acids of the formula III at least another acid compound comprising an acid of the formula I as defined above, an acid of the formula II as defined above; and
/or at least one acid compound comprising an additional different acid of the formula III as mentioned above wherein at least one moiety Q is present which is a linear or branched C1-C10-alkyl moiety substituted with 1 to 3 COOH, P(O)(OH)2 and/or S(O)2(OH) groups, with the proviso that in the case of a compound of the formula III said moiety Q does not carry only 2 COOH groups, is applied in addition;and wherein an acid of the formula I, II and/or III the mentioned COOH, P(O)(OH)2 and S(O)2(OH) groups may also be partially or completely present in negatively charged form, so that the acids of the formula I, II and/or Ill may also be partially or completely be present as salts. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 18, 19, 20, 21)
Compound 1 2 3 4 5
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7. The method according to claim 1 to achieve an antimicrobial effect.
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8. The method according to claim 1 which comprises applying a composition comprising one or more acid compounds of the formulae I, II or III and/or a salt thereof, wherein the acid compound(s) is present in 0.01 to 50% by weight.
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9. The method according to claim 1 for the protection within or on the surface of an article and/or material wherein, the acid compound used is one comprising Q selected from the group consisting of linear or branched C1-C10-alkyl moieties substituted with COOH, and the materials comprise synthetic polymers or polymer precursors or monomeric compounds, and the articles are articles made from such materials.
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18. The method according to claim 2, wherein the acid compound, acid compound mixture or composition comprising at least one acid compound with an acid of the formula I is used in the absence of acids of the formula II and III.
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19. The method according to claim 3, wherein the acid compound, acid compound mixture or composition comprising at least one acid compound with an acid of the formula II is used in the absence of acids of the formula I and Ill, and/or in each case a salt thereof.
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20. The method according to claim 4, wherein the acid compound, acid compound mixture or composition each comprising at least one acid compound with an acid of the formula III, and/or in each case a salt thereof is used in the absence of acids of the formula I and II.
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21. The method according to claim 8 which comprises applying a composition comprising one or more acid compounds of the formulae I, II or III and/or a salt thereof, wherein the acid compound(s) is present in 0.01 to 10% by weight.
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10-11. -11. (canceled)
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12. An acid compound, compound mixture or composition comprising
at least one acid comprising at least one moiety Q which represents a linear or branched C1-C10-alkyl moiety substituted with 1-3 functional groups independently selected from the group consisting of COOH, P(O)(OH)2 and S(O)2(OH) which are attached via a C-atom to said moiety, wherein said at least one acid is selected from one or more acids from the group consisting of one or more acids of the formula I, wherein R1=a linear or branched C1-C7-alkyl; -
m represents an integer from 1 to about 20; o represents an integer from 0 to 15; and the acid preferably has a polydispersity of up to about 3 and a weight-average molecular weight of 600 to about 3000; one or more acids of the general formula II, wherein R1=methyl n represents an integer from 0 to 15; and/or one or more acid of the formula III, wherein; R1=methyl p represents an integer from 1 to about 20; q represents an integer from 1 to about 20; r represents an integer from 0 to 15; and the acid preferably has a polydispersity of up to about 3 and a weight-average molecular weight of 600 to about 3000; in free form and/or as salt(s); with the proviso that if only acids of the formula III are present in a given compound, compound mixture or composition, at least in a part, preferably in all, of the molecules of the formula III one of the moieties Q is a linear or branched C1-C10-alkyl moiety substituted with 1 to 3 functional groups selected from P(O)(OH)2 and S(O)2(OH), or with 1 or 3 COOH groups. - View Dependent Claims (13, 14, 15, 16, 17)
Compound 2 3 5
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17. A process for the manufacture of an acid compound according to claim 12, comprising
(a) for the manufacture of an acid of the formula I, reacting a compound of the formula IA, wherein R1 and m are as defined for an acid of the formula I, under hydrosilylation conditions with a vinyl compound of the formula IV, wherein Q and o are as defined for an acid of the formula I, or (b) for the manufacture of an acid of the formula II, reacting a compound of the formula IIA, wherein R1 is as defined for an acid of the formula II, under hydrosilylation conditions with a vinyl compound of the formula IV*, wherein Q and n are as defined for an acid of the formula II, or (c) for the manufacture of an acid of the formula III, reacting a compound of the formula IIIA, wherein R1, p and q are as defined for an acid of the formula III, under hydrosilylation conditions with a vinyl compound of the formula IV**, wherein Q and r as defined for an acid of the formula III, with the proviso that in any of the starting materials of the formula IV, IV* and IV**, functional groups COOH, P(O)(OH)2 and S(O)2(OH) are present in protected form; -
and subsequently removing the protection from the functional groups; or leading two or more of the reactions under (a), (b) and (c) and the subsequent removal of protecting groups in parallel in order to directly obtain mixtures of acid compounds with acids of the formula I, II and/or III; and, optionally conversion into a salt of an acid compound obtained according to a process according to a), b) and/or c) or conversion of one acid salt is a different salt with a different cation.
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Specification
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Current AssigneeAndrea Preuss, Hölzl, Werner
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Original AssigneeAndrea Preuss, Hölzl, Werner
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InventorsHölzl, Werner, Preuss, Andrea
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Application NumberUS12/227,674Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/63CPC Class CodesA01N 37/04 polybasicA01N 41/04 Sulfonic acids; Derivatives...A01N 55/00 Biocides, pest repellants o...A01N 57/04 containing acyclic or cyclo...A01N 57/08 containing heterocyclic rad...C08L 83/06 containing silicon bound to...
