US 2011/0086791 A1Published application

Surface treatment composition containing phosphonic acid compounds

AssigneeDequest AG

InventorsPatrick Notte, Albert Devaux, Luc Feyt

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Abstract

Surface treatment compositions containing selected phosphonic acid compounds are disclosed. The compositions contain major levels of surface-active agents in combination with additive levels of the phosphonic acid compounds, and, in accordance with needs and objectives, conventional optional ingredients and additive agents. The inventive compositions can provide significant performance benefits, among others novel synergies and eminently desirable regulatory and environmental acceptability.

Claims12

Dependent claims

A surface treatment composition comprising a surface-active agent, and optionally further components and additives, characterized in that the composition comprises:

(a) from 99.9 to 40% by weight (based on the sum of (a) and (b)) of a surface-active agent;
and
(b) from 0.1 to 60% by weight (based on the sum of (a) and (b)) of a phosphonic acid compound selected from the group of:
(I) amino acid alkylene phosphonic acids having the formula
A1-(B)x
wherein A1 has the formula
HOOC-A-NH2
wherein A is independently selected from C2-C20 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbon groups, optionally substituted by OH, COOH and/or NH2 moieties, and
B is an alkylene phosphonic acid moiety having from 1 to 6 carbon atoms in the alkyl group and x is an integer of from 1 to 10;
(II) aminoacid alkylene phosphonic acids having the formula
A2-By
wherein A2 has the formula
HOOC—C(NH2)(R)(R′)
wherein R and R′ are independently selected from C1-C20 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbons groups, optionally substituted by OH, NH2 and/or COOH, and one of R or R′ can be hydrogen,
with the proviso of excluding:
compounds wherein R and/or R′ are electron rich moieties containing, at least, one lone pair of electrons, which moiety is directly attached to an aromatic moiety by a covalent bond;
or aromatics wherein at least one of the carbon atoms has been substituted by a heteroatom;
and compounds, in the event R is —C(X)(R″)(R′″) and R′, R″ and R′″ are hydrogen wherein X is an electron withdrawing group selected from NO2, CN, COOH, SO3H, OH and halogen, and
with the further proviso that when:
A2 is L-lysine, at least one L-lysine amino radical carries 2 (two) alkylene phosphonic acid moieties;
and when
A2 is L-glutamic acid, the term glutamic acid phosphonate represents a combination of from 50-90% by weight pyrrolidone carboxylic acid N-methylene phosphonic acid and from 10-50% by weight of L-glutamic acid diphosphonic acid, expressed on the basis of the reaction products;
and
B is an alkylene phosphonic acid moiety having from 1 to 6 carbon atoms in the alkyl group and y is an integer in the range of from 1 to 10;
(III) a phosphonate compound of the general formula:
T-B
wherein B is a phosphonate containing moiety having the formula:
—X—N(W)(ZPO3M2)
wherein X is selected from C2-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′ and SR′ moieties, wherein R′ is a C1-C12 linear, branched, cyclic or aromatic hydrocarbon moiety;
and [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
Z is a C1-C6 alkylene chain;
M is selected from H, C1-C20 linear, branched, cyclic or aromatic hydrocarbon moieties and from alkali, earth alkali and ammonium ions and from protonated amines;
W is selected from H, ZPO3M2 and [V—N(K)]nK, wherein V is selected from:
a C2-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by C1-C12 linear, branched, cyclic or aromatic groups, (which moieties and/or groups are) optionally substituted by OH, COOH, F, OR′ or SR′ moieties wherein R′ is a C1-C12 linear, branched, cyclic or aromatic hydrocarbon moiety;
and from [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
and
K is ZPO3M2 or H and n is an integer from 0 to 200;
and wherein T is a moiety selected from the group of:
MOOC—X—N(U)—;
(i)
MOOC—C(X2)2—N(U)—;
(ii)
MOOC—X—S—;
(iii)
[X(HO)n,(N—U)n′]n″;
(iv)
U—N(U)—[X—N(U)]n′″—;
(v)
D-S—;
(vi)
CN—;
(vii)
MOOC—X—O—;
(viii)
MOOC—C(X2)2-0-;
(ix)
NHR″—;
and (x)
(DCO)2—N—;
(xi)
wherein M, Z, W and X are as defined above;
U is selected from linear, branched, cyclic or aromatic C1-C12 hydrocarbon moieties, H and X—N(W)(ZPO3M2);
X2 is independently selected from H, linear, branched, cyclic or aromatic C1-C20 hydrocarbon moieties, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbon groups, optionally substituted by OH, COOH, R′ O, R′S and/or NH2 moieties;
n′, n″ and n′″ are independently selected from integers of from 1 to 100;
D and R″ are independently selected from C1-C50 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′ and SR′ moieties, wherein R′ is a C1-C12 linear, branched, cyclic or aromatic hydrocarbon moiety;
and A′O-[A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety, x is an integer from 1 to 200 and A′ is selected from C1-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′ and SR′ moieties, wherein R′ has the meaning given above;
with the further proviso that D can also be represented by H;
(IV) linear or branched hydrocarbon compounds having from 6 to 2.106 carbon atoms containing amino groups substituted by alkylene phosphonic acid substituents and/or —X—N(W)(ZPO3M2), with respect to the hydrocarbon group, in either terminal or branched positions whereby the molar ratio of the aminoalkylene phosphonic acid substituents to the number of carbon atoms in the hydrocarbon group is in the range of from 2:1 to 1:40 whereby at least 30% of the available NH functionalities have been converted into the corresponding aminoalkylene phosphonic acid and/or into —X—N(W)(ZPO3M2) substituted groups and wherein the alkylene moiety is selected from C1-C6;
and X, W, Z and M have the same meaning as given above;
and
(V) alkylamino alkylene phosphonic acids having the formula:
Y—[X—N(W)(ZPO3M2)]s
the structural elements having the following meaning:
X is selected from C2-C50 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′, R2O [A-O]x— wherein R2 is a C10-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, and SR′ moieties, wherein R′ is a C10-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbon groups, (said moieties and/or groups can be) optionally substituted by COOH, OH, F, OR′ and SR′;
and [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
Z is a C1-C6 alkylene chain;
M is selected from H, C1-C20 linear, branched, cyclic or aromatic hydrocarbon moieties and from alkali, earth alkali and ammonium ions and from protonated amines;
W is selected from H, ZPO3M2 and [V—N(K)]nK, wherein V is selected from:
a C2-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by C1C12 linear, branched, cyclic or aromatic groups, (which moieties and/or groups can be) optionally substituted by OH, COOH, F, OR′, R2O [A-O]x— wherein R2 is a C1-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, and SR′ moieties;
and from [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
K is ZPO3M2 or H and n is an integer from 0 to 200;
and
Y is a moiety selected from NH2, NHR′, N(R′)2, NH, N, OH, OR′, S, SH, and S—S wherein R′ is as defined above with the proviso that when Y is OH or OR′, X is, at least, C4;
and
s is 1 in the event Y stands for NH2, NHR′, N(R′)2, HS, OR′, or OH;
s is 2 in the event Y stands for NH, NR′, S or S—S;
and s is 3 in the event Y stands for N.

84 more elements

Dependencies are inferred from the claim text.

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Abstract

A surface treatment composition comprising a surface-active agent, and optionally further components and additives, characterized in that the composition comprises:

(a) from 99.9 to 40% by weight (based on the sum of (a) and (b)) of a surface-active agent;
and
(b) from 0.1 to 60% by weight (based on the sum of (a) and (b)) of a phosphonic acid compound selected from the group of:
(I) amino acid alkylene phosphonic acids having the formula
A1-(B)x
wherein A1 has the formula
HOOC-A-NH2
wherein A is independently selected from C2-C20 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbon groups, optionally substituted by OH, COOH and/or NH2 moieties, and
B is an alkylene phosphonic acid moiety having from 1 to 6 carbon atoms in the alkyl group and x is an integer of from 1 to 10;
(II) aminoacid alkylene phosphonic acids having the formula
A2-By
wherein A2 has the formula
HOOC—C(NH2)(R)(R′)
wherein R and R′ are independently selected from C1-C20 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbons groups, optionally substituted by OH, NH2 and/or COOH, and one of R or R′ can be hydrogen,
with the proviso of excluding:
compounds wherein R and/or R′ are electron rich moieties containing, at least, one lone pair of electrons, which moiety is directly attached to an aromatic moiety by a covalent bond;
or aromatics wherein at least one of the carbon atoms has been substituted by a heteroatom;
and compounds, in the event R is —C(X)(R″)(R′″) and R′, R″ and R′″ are hydrogen wherein X is an electron withdrawing group selected from NO2, CN, COOH, SO3H, OH and halogen, and
with the further proviso that when:
A2 is L-lysine, at least one L-lysine amino radical carries 2 (two) alkylene phosphonic acid moieties;
and when
A2 is L-glutamic acid, the term glutamic acid phosphonate represents a combination of from 50-90% by weight pyrrolidone carboxylic acid N-methylene phosphonic acid and from 10-50% by weight of L-glutamic acid diphosphonic acid, expressed on the basis of the reaction products;
and
B is an alkylene phosphonic acid moiety having from 1 to 6 carbon atoms in the alkyl group and y is an integer in the range of from 1 to 10;
(III) a phosphonate compound of the general formula:
T-B
wherein B is a phosphonate containing moiety having the formula:
—X—N(W)(ZPO3M2)
wherein X is selected from C2-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′ and SR′ moieties, wherein R′ is a C1-C12 linear, branched, cyclic or aromatic hydrocarbon moiety;
and [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
Z is a C1-C6 alkylene chain;
M is selected from H, C1-C20 linear, branched, cyclic or aromatic hydrocarbon moieties and from alkali, earth alkali and ammonium ions and from protonated amines;
W is selected from H, ZPO3M2 and [V—N(K)]nK, wherein V is selected from:
a C2-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by C1-C12 linear, branched, cyclic or aromatic groups, (which moieties and/or groups are) optionally substituted by OH, COOH, F, OR′ or SR′ moieties wherein R′ is a C1-C12 linear, branched, cyclic or aromatic hydrocarbon moiety;
and from [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
and
K is ZPO3M2 or H and n is an integer from 0 to 200;
and wherein T is a moiety selected from the group of:
MOOC—X—N(U)—;
(i)
MOOC—C(X2)2—N(U)—;
(ii)
MOOC—X—S—;
(iii)
[X(HO)n,(N—U)n′]n″;
(iv)
U—N(U)—[X—N(U)]n′″—;
(v)
D-S—;
(vi)
CN—;
(vii)
MOOC—X—O—;
(viii)
MOOC—C(X2)2-0-;
(ix)
NHR″—;
and (x)
(DCO)2—N—;
(xi)
wherein M, Z, W and X are as defined above;
U is selected from linear, branched, cyclic or aromatic C1-C12 hydrocarbon moieties, H and X—N(W)(ZPO3M2);
X2 is independently selected from H, linear, branched, cyclic or aromatic C1-C20 hydrocarbon moieties, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbon groups, optionally substituted by OH, COOH, R′ O, R′S and/or NH2 moieties;
n′, n″ and n′″ are independently selected from integers of from 1 to 100;
D and R″ are independently selected from C1-C50 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′ and SR′ moieties, wherein R′ is a C1-C12 linear, branched, cyclic or aromatic hydrocarbon moiety;
and A′O-[A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety, x is an integer from 1 to 200 and A′ is selected from C1-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′ and SR′ moieties, wherein R′ has the meaning given above;
with the further proviso that D can also be represented by H;
(IV) linear or branched hydrocarbon compounds having from 6 to 2.106 carbon atoms containing amino groups substituted by alkylene phosphonic acid substituents and/or —X—N(W)(ZPO3M2), with respect to the hydrocarbon group, in either terminal or branched positions whereby the molar ratio of the aminoalkylene phosphonic acid substituents to the number of carbon atoms in the hydrocarbon group is in the range of from 2:1 to 1:40 whereby at least 30% of the available NH functionalities have been converted into the corresponding aminoalkylene phosphonic acid and/or into —X—N(W)(ZPO3M2) substituted groups and wherein the alkylene moiety is selected from C1-C6;
and X, W, Z and M have the same meaning as given above;
and
(V) alkylamino alkylene phosphonic acids having the formula:
Y—[X—N(W)(ZPO3M2)]s
the structural elements having the following meaning:
X is selected from C2-C50 linear, branched, cyclic or aromatic hydrocarbon moieties, optionally substituted by a C1-C12 linear, branched, cyclic, or aromatic group, (which moiety and/or which group can be) optionally substituted by OH, COOH, F, OR′, R2O [A-O]x— wherein R2 is a C10-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, and SR′ moieties, wherein R′ is a C10-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by C1-C12 linear, branched, cyclic or aromatic hydrocarbon groups, (said moieties and/or groups can be) optionally substituted by COOH, OH, F, OR′ and SR′;
and [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
Z is a C1-C6 alkylene chain;
M is selected from H, C1-C20 linear, branched, cyclic or aromatic hydrocarbon moieties and from alkali, earth alkali and ammonium ions and from protonated amines;
W is selected from H, ZPO3M2 and [V—N(K)]nK, wherein V is selected from:
a C2-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, optionally substituted by C1C12 linear, branched, cyclic or aromatic groups, (which moieties and/or groups can be) optionally substituted by OH, COOH, F, OR′, R2O [A-O]x— wherein R2 is a C1-C50 linear, branched, cyclic or aromatic hydrocarbon moiety, and SR′ moieties;
and from [A-O]x-A wherein A is a C2-C9 linear, branched, cyclic or aromatic hydrocarbon moiety and x is an integer from 1 to 200;
K is ZPO3M2 or H and n is an integer from 0 to 200;
and
Y is a moiety selected from NH2, NHR′, N(R′)2, NH, N, OH, OR′, S, SH, and S—S wherein R′ is as defined above with the proviso that when Y is OH or OR′, X is, at least, C4;
and
s is 1 in the event Y stands for NH2, NHR′, N(R′)2, HS, OR′, or OH;
s is 2 in the event Y stands for NH, NR′, S or S—S;
and s is 3 in the event Y stands for N.

84 more elements