IP Library Granted Patent US 8,377,326
Granted Patent B2
US 8,377,326 · App. 12/922,857 · Granted Feb 19, 2013

Use of polyamino and/or polyammonium-polysiloxane-copolymer compounds

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Quick Facts
Patent No.
US 8,377,326
App. No.
12/922,857
Granted
Feb 19, 2013
Kind
B2
Abstract

The invention relates to the use of polyamino and/or polyammonium-polysiloxane-copolymer compounds or aqueous emulsions thereof for of the first finishing of fibrous materials, aqueous emulsions of the polyamino and/or polyammonium-polysiloxane-copolymer compounds, as well as a method for the first finishing of fibrous materials.

Claims (539)

1. A method of first finishing of a fiber material comprising applying to the fiber material a polyamino and/or polyammonium-polysiloxane-copolymer compounds comprising units of the formula (I):

-[Q-V]—  (I)

wherein Q is selected from the group consisting of:

—NR—,

—N + R 2 —

a saturated or unsaturated diamino-functional heterocycle of the formulae:

 as well as an aromatic diamino-functional heterocycle of the formula:

a trivalent residue of the formula:

a trivalent residue of the formula:

a tetravalent residue of the formula:

wherein R respectively represents hydrogen or a monovalent organic residue,

wherein Q does not bond to a carbonyl carbon atom,

V is selected from the group consisting of V 11 , V 12 , V 2 and V 3 , wherein

V 2 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms (wherein the carbon atoms of the polysiloxane residue Z 2 defined below are not included in this number), which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 represents hydrogen, a monovalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups selected from

—O—,

—NH—,

—C(O)— and

—C(S)—,

and which may optionally be substituted by one or more substituents selected from the group consisting of:

a hydroxyl group,

an optionally substituted heterocyclic group preferably containing one or more nitrogen atoms,

amino,

alkylamino,

dialkylamino,

ammonium,

polyether residues and

polyether ester residues,

wherein, if several groups —CONR 2 are present, they may be the same or different,

—C(O)— and

—C(S)—, and

the residue V 2 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue, and

the residue V 2 contains at least one group —Z 2 — of the formula

wherein

R 1 may be the same or different and is selected from the group consisting of:

C 1 to C 22 -alkyl,

fluoro(C 1 -C 10 )alkyl, C 6 -C 10 -aryl and

—W—Si(OR) 3-a (R′) a , wherein

R, R′ and a are defined as above, and

W is

—O— or

a divalent, straight-chained or cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups

 —C(O)—,

 —O—,

 —NH—, and

 —S— and

may optionally be substituted by hydroxyl groups, and

n 1 =20 to 52,

V 11 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 is as defined above, wherein the groups R 2 in the groups V 11 and V 2 may be the same or different,

—C(O)—,

—C(S)— and

—Z 1 —, wherein

—Z 1 — is a group of the formula

 wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 11 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 11 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that the residue V 11 comprises (poly)alkyleneoxide units,

V 12 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 is as defined above, wherein the groups R 2 in the groups V 12 and V 2 may be the same or different,

—C(O)—,

—C(S)— and

—Z 1 —, wherein

—Z 1 — is a group of the formula

 wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 12 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 12 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that the residue V 12 comprises no (poly)alkyleneoxide units, and

V 3 represents a tri- or higher-valent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein R 2 is as defined above,

—C(O)—,

—C(S)—,

—Z 1 —, which is as defined above,

—Z 2 — which is as defined above, and

Z 3 , wherein Z 3 is a tri- or higher-valent organopolysiloxane unit, and

which may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that

the polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one residue V 11 and at least one residue V 12 ,

the above-mentioned polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one group —Z 1 —, —Z 2 — or Z 3 , and

that the tri- and tetravalent residues Q either serve for branching the main chain formed from Q and V, so that the valences which do not serve for bonding in the main chain carry further branchings formed from -[Q-V]— units, or the tri- and tetravalent residues Q are saturated with residues V 3 within a linear main chain without forming a branching, and

wherein the positive charges resulting from ammonium groups are neutralized by organic or inorganic acid anions,

wherein V comprises repeating units of the formula V 11 , V 12 and V 2 , wherein the polyamino and/or polyammonium-polysiloxane-copolymer compounds comprise the formula (III):

Q, V 11 , V 12 and V 2 are defined as above and wherein v1 to v2 to w represent the molar ratio of the corresponding units -Q—V 11 —,-Q—V 12 —and -Q—V 2 —, and wherein the molar ratio of w to v1 in mol- % is from 80 to 99, relative to the sum of w and v1.

2. The method of claim 1 , wherein the molar ratio of v1 to v2 in mol- % is between 0 to 100.

3. The method of claim 1 , wherein, on average, the polyamino and/or polyammonium-polysiloxane-copolymer compounds comprise at least two repeating units of the formula (I).

4. The method of claim 1 , wherein the groups V 11 and V 12 are selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 600 carbon atoms, which may optionally contain one or more groups selected from —O—, —CONH—,—CONR 2 —, wherein R 2 is as defined above, —C(O)—,—C(S)— and —Z 1 —, wherein —Z 1 — is a group of the formula

wherein

R 1 is C 1 -C 18 alkyl, which may optionally be substituted with one or more fluorine atoms, or phenyl, and n 2 is as defined above, provided that the residue V 11 is a (poly)alkyleneoxide-containing residue and that the residue V 12 is a residue that contains no (poly)alkyleneoxide residue.

5. The method of claim 1 , wherein the group V 2 is a group of the formula

—V 2 *—Z 2 —V 2 *—

wherein Z 2 is as defined above and V 2* represents a divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 40 carbon atoms, which may optionally contain one or more groups selected from —O—,—CONH—,—CONR 2 —, wherein R 2 is as defined above, —C(O)—and —C(S)—, and the residue V 2* may optionally be substituted by one or more hydroxyl groups.

6. The method of claim 1 , wherein V 12 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 100 carbon atoms, which may optionally contain one or more groups selected from

—Z 1 —, wherein

—Z 1 — is a group of the formula

wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 12 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 12 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue.

7. The method of claim 1 , wherein the group V 12 is a residue —R 9 —, wherein R 9 represents a divalent, saturated or mono- or polyunsaturated, straight-chained or branched hydrocarbon residue with two to 25 carbon atoms.

8. The method of claim 1 , wherein group V 11 is selected from

—(CH 2 ) u C(O)O—[(CH 2 CH 2 O) q —(CH 2 CH(CH 3 )O) r ]—C(O)(CH 2 ) u —

—(CH 2 ) u C(O)O—R 9 —O—C(O)(CH 2 ) u —, wherein R 9 is as defined above,

—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH 2 —,

—CH(CH 3 )CH 2 O[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH(CH 3 )—

—CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 — and

—CH 2 CH(OH)CH 2 O—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH(OH)CH 2 —

wherein

u is 1 to 3,

q and r are each 0 to 5, and

q+r>0.

9. The method of claim 1 , wherein group V 11 is selected from

—(CH 2 )C(O)O—[(CH 2 CH 2 O) q ]—C(O)(CH 2 )—

wherein q=1 or 2.

10. The method of claim 1 , wherein at least one further polydiorganosiloxane compound different therefrom is applied.

11. The method of claim 1 , wherein the fiber materials are selected from natural and synthetic fibrous materials including cellulose, wool, cotton, silk and synthetic fibers.

12. A method of finishing of a fiber material comprising applying to the fiber material a polyamino and/or polyammonium-polysiloxane-copolymer compounds comprising units of the formula (I):

-[Q—V]—  (I)

wherein Q is selected from the group consisting of:

—NR—,

—N + R 2 —

a saturated or unsaturated diamino-functional heterocycle of the formulae:

 as well as an aromatic diamino-functional heterocycle of the formula:

a trivalent residue of the formula:

a trivalent residue of the formula:

a tetravalent residue of the formula:

wherein R respectively represents hydrogen or a monovalent organic residue,

wherein Q does not bond to a carbonyl carbon atom,

V is selected from the group consisting of V 11 , V 12 , V 2 and V 3 , wherein

V 2 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms (wherein the carbon atoms of the polysiloxane residue Z 2 defined below are not included in this number), which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 represents hydrogen, a monovalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups selected from

—O—,

—NH—,

—C(O)—and

—C(S)—,

and which may optionally be substituted by one or more substituents selected from the group consisting of:

a hydroxyl group,

an optionally substituted heterocyclic group preferably containing one or more nitrogen atoms,

amino,

alkylamino,

dialkylamino,

ammonium,

polyether residues and

polyether ester residues,

wherein, if several groups —CONR 2 are present, they may be the same or different,

—C(O)—and

—C(S)—, and

the residue V 2 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue, and

the residue V 2 contains at least one group —Z 2 — of the formula

wherein

R 1 may be the same or different and is selected from the group consisting of:

C 1 to C 22 -alkyl,

fluoro(C 1 -C 10 )alkyl, C 6 -C 10 -aryl and

—W—Si(OR) 3-a (R′) a , wherein

R, R′ and a are defined as above, and

W is

—O— or

a divalent, straight-chained or cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups

 —C(O)—,

 —O—,

 —NH—, and

 —S— and

may optionally be substituted by hydroxyl groups, and

n 1 =20 to 52,

V 11 is selected from the group consisting of

—(CH 2 ) u C(O)O—[(CH 2 CH 2 O) q —(CH 2 CH(CH 3 )O) r ]—C(O)(CH 2 ) u —

—(CH 2 ) u C(O)O—R 9 —O—C(O)(CH 2 ) u —, wherein R 9 is as defined above,

—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH 2 —,

—CH(CH 3 )CH 2 O[CH 2 CH 2 O] q —[CH 2 CH(CH 3 O] r —CH 2 CH(CH 3 )—

—CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 — and

—CH 2 CH(OH)CH 2 O—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH(OH)CH 2 —

wherein

u is 1 to 3,

q and r are each 0 to 5, and

q+r>0,

V 12 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 is as defined above, wherein the groups R 2 in the groups V 12 and V 2 may be the same or different,

—C(O)—,

—C(S)— and

—Z 1 —, wherein

—Z 1 — is a group of the formula

wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 12 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 12 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that the residue V 12 comprises no (poly)alkyleneoxide units, and

V 3 represents a tri- or higher-valent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein R 2 is as defined above,

—C(O)—,

—C(S)—,

—Z 1 —, which is as defined above,

—Z 2 — which is as defined above, and

Z 3 , wherein Z 3 is a tri- or higher-valent organopolysiloxane unit, and

which may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that

the polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one residue V 11 and at least one residue V 12 ,

the above-mentioned polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one group —Z 1 —, —Z 2 —or Z 3 , and

that the tri- and tetravalent residues Q either serve for branching the main chain formed from Q and V, so that the valences which do not serve for bonding in the main chain carry further branchings formed from -[Q-V]— units, or the tri- and tetravalent residues Q are saturated with residues V 3 within a linear main chain without forming a branching, and

wherein the positive charges resulting from ammonium groups are neutralized by organic or inorganic acid anions,

wherein V comprises repeating units of the formula V 11 , V 12 and V 2 .

13. method of finishing of a fiber material comprising applying to the fiber material a polyamino and/or polyammonium-polysiloxane-copolymer compounds comprising units of the formula (I):

-[Q-V]—  (I)

wherein Q is selected from the group consisting of:

—NR—,

—N + R 2 —

a saturated or unsaturated diamino-functional heterocycle of the formulae:

as well as an aromatic diamino-functional heterocycle of the formula:

a trivalent residue of the formula:

a trivalent residue of the formula:

a tetravalent residue of the formula:

wherein R respectively represents hydrogen or a monovalent organic residue,

wherein Q does not bond to a carbonyl carbon atom,

V is selected from the group consisting of V 11 , V 12 , V 2 and V 3 , wherein

V 2 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms (wherein the carbon atoms of the polysiloxane residue Z 2 defined below are not included in this number), which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 represents hydrogen, a monovalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups selected from

—O—,

—NH—,

—C(O)— and

—C(S)—,

and which may optionally be substituted by one or more substituents selected from the group consisting of:

a hydroxyl group,

an optionally substituted heterocyclic group preferably containing one or more nitrogen atoms,

amino,

alkylamino,

dialkylamino,

ammonium,

polyether residues and

polyether ester residues,

wherein, if several groups —CONR 2 are present, they may be the same or different,

—C(O)— and

—C(S)—, and

the residue V 2 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue, and

the residue V 2 contains at least one group —Z 2 — of the formula

wherein

R l may be the same or different and is selected from the group consisting of:

C 1 to C 22 -alkyl,

fluoro(C 1 —C 10 )alkyl, C 6 —C 10 -aryl and

—W—Si(OR) 3-a (R′) a , wherein

R, R′ and a are defined as above, and

W is

—O— or

a divalent, straight-chained or cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups

 —C(O)—,

 —O—,

 —NH—, and

 —S— and

may optionally be substituted by hydroxyl groups, and

n 1 =20 to 52,

V 11 is selected from the group consisting of

—(CH 2 ) u C(O)O—[(CH 2 CH 2 O) q —(CH 2 CH(CH 3 )O) r ]—C(O)(CH 2 ) u —

—(CH 2 ) u C(O)O—R 9 —O—C(O)(CH 2 ) u —, wherein R 9 is as defined above,

—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH 2 —,

—CH(CH 3 )CH 2 O[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O]—CH 2 CH(CH 3 )—

—CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 — and

—CH 2 CH(OH)CH 2 O—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH(OH)CH 2 —

wherein

u is 1 to 3,

q and r are each 0 to 5, and

q +r>0,

V 12 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 is as defined above, wherein the groups R 2 in the groups V 12 and V 2 may be the same or different,

—C(O)—,

—C(S)— and

—Z 1 —, wherein

—Z 1 — is a group of the formula

wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 12 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 12 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that the residue V 12 comprises no (poly)alkyleneoxide units, and

V 3 represents a tri- or higher-valent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein R 2 is as defined above,

—C(O)—,

—C(S)—,

—Z 1 —, which is as defined above,

—Z 2 — which is as defined above, and

Z 3 , wherein Z 3 is a tri- or higher-valent organopolysiloxane unit, and

which may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that

the polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one residue V 11 and at least one residue V 12 ,

the above-mentioned polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one group —Z 1 —, —Z 2 — or Z 3 , and

that the tri- and tetravalent residues Q either serve for branching the main chain formed from Q and V, so that the valences which do not serve for bonding in the main chain carry further branchings formed from -[Q-V]— units, or the tri- and tetravalent residues Q are saturated with residues V 3 within a linear main chain without forming a branching, and

wherein the positive charges resulting from ammonium groups are neutralized by organic or inorganic acid anions,

wherein the polyamino and/or polyammonium-polysiloxane-copolymer compounds comprise the formula (III):

Q, V 11 , V 12 and V 2 are defined as above, and wherein v1 to v2 to w represent the molar ratio of the corresponding units -Q-V 11 —,-Q-V 12 — and -Q-V 2 —.

14. The method of claim 13 , wherein the molar ratio of w to v1 in mol- % is from 80 to 99, relative to the sum of w and v1.

15. Polyamino and/or polyammonium-polysiloxane-copolymer compounds comprising units of the formula (I):

-[Q-V]—  (I)

wherein Q is selected from the group consisting of:

—NR—,

—N + R 2 —

a saturated or unsaturated diamino-functional heterocycle of the formulae:

 as well as an aromatic diamino-functional heterocycle of the formula:

a trivalent residue of the formula:

a trivalent residue of the formula:

a tetravalent residue of the formula:

wherein R respectively represents hydrogen or a monovalent organic residue,

wherein Q does not bond to a carbonyl carbon atom,

V is selected from the group consisting of V 11 , V 12 , V 2 and V 3 , wherein

V 2 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms (wherein the carbon atoms of the polysiloxane residue Z 2 defined below are not included in this number), which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 represents hydrogen, a monovalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups selected from

—O—,

—NH—,

—C(O)— and

—C(S)—,

and which may optionally be substituted by one or more substituents selected from the group consisting of:

a hydroxyl group,

an optionally substituted heterocyclic group preferably containing

one or more nitrogen atoms,

amino,

alkylamino,

dialkylamino,

ammonium,

polyether residues and

polyether ester residues,

wherein, if several groups —CONR 2 are present, they may be the same or different,

—C(O)— and

—C(S)—, and

the residue V 2 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue, and

the residue V 2 contains at least one group —Z 2 — of the formula

wherein

R l may be the same or different and is selected from the group consisting of:

C 1 to C 22 -alkyl,

fluoro(C 1 -C 10 )alkyl, C 6 -C 10 -aryl and

—W—Si(OR) 3-a (R′) a , wherein

R, R′ and a are defined as above, and

W is

—O— or

a divalent, straight-chained or cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups

 —C(O)—,

 —O—,

 —NH—, and

 —S— and

may optionally be substituted by hydroxyl groups, and

n 1 =20 to 52,

V 11 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 is as defined above, wherein the groups R 2 in the groups V 11 and V 2 may be the same or different,

—C(O)—,

—C(S)— and

—Z 1 —, wherein

—Z 1 — is a group of the formula

wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 11 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 11 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that the residue V 11 comprises (poly)alkyleneoxide units,

V 12 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 is as defined above, wherein the groups R 2 in the groups V 12 and V 2 may be the same or different,

—C(O)—,

—C(S) — and

—Z 1 —, wherein

—Z 1 — is a group of the formula

wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 12 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 12 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that the residue V 12 comprises no (poly)alkyleneoxide units, and

V 3 represents a tri- or higher-valent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein R 2 is as defined above,

—C(O)—,

—C(S)—,

—Z 1 —, which is as defined above,

—Z 2 — which is as defined above, and

Z 3 , wherein Z 3 is a tri- or higher-valent organopolysiloxane unit, and

which may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that

the polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one residue V 11 and at least one residue V 12 ,

the above-mentioned polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one group —Z 1 —, —Z 2 — or Z 3 , and

that the tri- and tetravalent residues Q either serve for branching the main chain formed from Q and V, so that the valences which do not serve for bonding in the main chain carry further branchings formed from -[Q-V]— units, or the tri- and tetravalent residues Q are saturated with residues V 3 within a linear main chain without forming a branching, and

wherein the positive charges resulting from ammonium groups are neutralized by organic or inorganic acid anions, wherein V comprises repeating units of the formula V 11 , V 12 and V 2 , wherein the polyamino and/or polyammonium-polysiloxane-copolymer compounds comprise the formula (III):

Q, V 11 , V 12 and V 2 are defined as above, and wherein v1 to v2 to w represent the molar ratio of the corresponding units -Q-V 11 —,-Q-V 12 — and -Q-V 2 —, and wherein the molar ratio of w to v1 in mol- % is from 80 to 99, relative to the sum of w and v1.

16. Polyamino and/or polyammonium-polysiloxane-copolymer compounds comprising units of the formula (I):

-[Q-V]—  (I)

wherein Q is selected from the group consisting of:

—NR—,

—N + R 2 —

a saturated or unsaturated diamino-functional heterocycle of the formulae:

 as well as an aromatic diamino-functional heterocycle of the formula:

a trivalent residue of the formula:

a trivalent residue of the formula:

a tetravalent residue of the formula:

wherein R respectively represents hydrogen or a monovalent organic residue,

wherein Q does not bond to a carbonyl carbon atom,

V is selected from the group consisting of V 11 , V 12 , V 2 and V 3 , wherein

V 2 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms (wherein the carbon atoms of the polysiloxane residue Z 2 defined below are not included in this number), which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 represents hydrogen, a monovalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups selected from

—O—,

—NH—,

—C(O)— and

—C(S)—,

and which may optionally be substituted by one or more substituents selected from the group consisting of:

a hydroxyl group,

an optionally substituted heterocyclic group preferably containing one or more nitrogen atoms,

amino,

alkylamino,

dialkylamino,

ammonium,

polyether residues and

polyether ester residues,

wherein, if several groups —CONR 2 are present, they may be the same or different,

—C(O)— and

—C(S)—, and

the residue V 2 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue, and

the residue V 2 contains at least one group —Z 2 — of the formula

wherein

R l may be the same or different and is selected from the group consisting of:

C 1 to C 22 -alkyl,

fluoro(C 1 -C 10 )alkyl, C 6 -C 10 -aryl and

—W—Si(OR) 3-a (R′) a , wherein

R, R′ and a are defined as above, and

W is

—O— or

a divalent, straight-chained or cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups

 —C(O)—,

 —O—,

 —NH—, and

 —S— and

may optionally be substituted by hydroxyl groups, and

n 1 =20 to 52,

V 11 is selected from the group consisting of

—(CH 2 ) u C(O)O—[(CH 2 CH 2 O) q —(CH 2 CH(CH 3 )O) r ]—C(O)(CH 2 ) u —

—(CH 2 ) u C(O)O—R 9 —O—C(O)(CH 2 ) u —, wherein R 9 is as defined above,

—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH 2 —,

—CH(CH 3 )CH 2 O[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH(CH 3 )—

—CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 — and

—CH 2 CH(OH)CH 2 O—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —CH 2 CH(OH)CH 2 —

wherein

u is 1 to 3,

q and r are each 0 to 5, and

q+r>0,

V 12 is selected from divalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residues with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein

R 2 is as defined above, wherein the groups R 2 in the groups V 12 and V 2 may be the same or different,

—C(O)—,

—C(S)— and

—Z 1 , wherein

—Z 1 — is a group of the formula

wherein

R 1 is as defined above, wherein the groups R 1 in the groups V 12 and V 2 may be the same or different, and

n 2 =0 to 19, and

the residue V 12 may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that the residue V 12 comprises no (poly)alkyleneoxide units, and

V 3 represents a tri- or higher-valent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 1000 carbon atoms, which may optionally contain one or more groups selected from

—O—,

—CONH—,

—CONR 2 —, wherein R 2 is as defined above,

—C(O)—,

—C(S)—,

—Z 1 —, which is as defined above,

—Z 2 — which is as defined above, and

Z 3 , wherein Z 3 is a tri- or higher-valent organopolysiloxane unit, and

which may optionally be substituted by one or more hydroxyl groups and/or by

—Si(OR) 3-a (R′) a

wherein a is an integer from 0 to 2, and R and R′ may be the same or different from each other, and each represent an organic residue,

provided that

the polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one residue V 11 and at least one residue V 12 ,

the above-mentioned polyamino and/or polyammonium-polysiloxane-copolymer compounds contain at least one group —Z 1 —, —Z 2 — or Z 3 , and

that the tri- and tetravalent residues Q either serve for branching the main chain formed from Q and V, so that the valences which do not serve for bonding in the main chain carry further branchings formed from -[Q-V]— units, or the tri- and tetravalent residues Q are saturated with residues V 3 within a linear main chain without forming a branching, and

wherein the positive charges resulting from ammonium groups are neutralized by organic or inorganic acid anions, wherein V comprises repeating units of the formula V 11 , V 12 and V 2 .

17. An aqueous emulsion, comprising the polyamino and/or polyammonium-polysiloxane-copolymer compound of claim 16 , and optionally one or more surfactants and optionally one or more nitrogen-free polysiloxane compounds.

18. A method of finishing of a fiber material comprising applying the aqueous emulsion of claim 17 to the fiber material.

Assignments (2)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded May 4, 2023
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063548/0281 →
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054336/0023 →