IP Library Granted Patent US 7,902,297
Granted Patent B2
US 7,902,297 · App. 11/920,880 · Granted Mar 8, 2011

Slip- and leveling agent

Assignee: BASF SE
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Quick Facts
Patent No.
US 7,902,297
App. No.
11/920,880
Granted
Mar 8, 2011
Kind
B2
Abstract

The invention relates to a slip- and leveling agent characterized in that it comprises a copolymer which is obtained by copolymerizing A. at least one unit of a mono- or di perfluoroester of an unsaturated dicarboxylic-acid; B. at least one terminal reactive polysiloxane unit; C. at least one alkyl(meth)acrylate unit or cycloalkyl(meth)acrylate unit and/or (meth)acrylic acid and/or other units originating from vinylic compounds that can form radicals.

Claims (40)

1. A slip- and leveling agent characterized in that it comprises a copolymer which is obtained by copolymerizing

A at least one unit of a mono- or di perfluoroester of an unsaturated dicarboxylic-acid;

B at least one terminal reactive polysiloxane unit;

C at least one alkyl(meth)acrylate unit or cycloalkyl(meth)acrylate unit and/or (meth)acrylic acid and/or other units originating from vinylic compounds that can form radicals.

2. A slip-and levelling agent according to claim 1 , characterized in that it comprises a copolymer which is obtained by copolymerizing

A 0.1-10 wt. % of a mono- or di perfluoroester of an unsaturated dicarboxylic-acid;

B 1-20 wt % of the terminal reactive polysiloxane compound;

C 50-99 wt % alkyl(meth)acrylate units and/or (meth)acrylic acid and/or other unit originating from vinylic compounds that can form radicals.

3. A slip-and levelling agent according to claim 1 , wherein A is represented by formula I,

wherein

R 1 is a moiety selected from the group consisting of C n F 2n+1 —(CH 2 ) m —, AC n F 2n —(CH 2 ) m —, C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —, AC n F 2n —(CH 2 ) m —(OCH 2 CHR 5 ) p , C n F 2n+1 —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —(OCH 2 CHR 5 ) p —X and C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —X—;

wherein A is selected from the group consisting of H, Cl, Br, I, C 1-12 alkyls and OC 1-12 alkyls, wherein 4≦n≦20, 0≦m≦4 and 0≦p≦20, wherein X is a spacer moiety selected from the group consisting of esters, amides, sulphonamides, mercapto groups, polyurethane groups and alkyl groups,

R 2 is selected from the group consisting of H, metal moieties, (alkyl)ammonium moieties, alkyl groups, C n F 2n+1 —(CH 2 ) m —, AC n F 2n —(CH 2 ) m —, C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —, AC n F 2n —(CH 2 ) m —(OCH 2 CHR 5 ) p , C n F 2n+1 —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —(OCH 2 —CHR5) p —X and C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —X—; wherein A is selected from the group consisting of H, Cl, Br, I, C 1-12 alkyls and OC 1-12 alkyls, wherein 4≦n≦20, 0≦m≦4 and 0≦p≦20, wherein X is a spacer moiety selected from the group consisting of esters, amides, sulphoamides, mercapto groups, polyurethane groups and alkyl groups,

R 3 and R 4 are independently selected from the group consisting of H, alkyl-groups and phenyl-groups and wherein R 5 is selected from the group consisting of H and methyl groups.

4. A slip-and levelling agent according to claim 3 , wherein

R 1 is a moiety selected from the group consisting of C n F 2n+1 —(CH 2 ) m —, C n F 2n+1 —(CH 2 ) m —(OCH 2 CH 2 ) p —, C n F 2n+1 —(CH 2 ) m —X— and C n F 2n+1 —(CH 2 ) m —(OCH 2 CH 2 ) p —X— wherein n is 4 or 6 or 8;

m is 1, 2 or 3; and p is 0, 6, 7 or 8;

R 3 and R 4 are H;

X is −O—CO(CH 2 ) x — or —CO—O(CH 2 ) x —, —NRCO(CH 2 ) x — or —CONR(CH 2 ) x —, —SO 2 NR(CH 2 ) x —; —S(CH 2 ) x —, —O—CONH(CH 2 ) x — or —NH—CO 2 (CH 2 ) x —, —O(CRHCH 2 ) x —, —(CRH) x — or —CR═CR(CRH) x —, wherein x=0-6 and R═H or C 1-6 alkyl.

5. A slip-and levelling agent according to claim 1 , wherein at least 50% of the fluorinated monomeric units A are mono-esters.

6. A slip-and levelling agent according to claim 1 , which is obtained by polymerizing

A at least one unit of a mono- or di perfluoroester of maleic acid;

B a mono-(meth)acrylic functional polydimethylsiloxane or a mono-maleic functional polydimethylsiloxane; and

C an alkyl(meth)acrylate unit, cycloalkyl(meth)acrylate unit or a styrene unit.

7. A coating, printing ink or plastic compound comprising a slip- and leveling agent according to claim 1 , a pigment and optionally a dispersant.

8. A dispersion, comprising 0-85% by weight of pigment and/or extender, 0.1-5% by weight of a copolymer according to claim 1 , 10-95% by weight of a resin, 0-90% by weight of water and/or non-aqueous liquid and 0-15% by weight of dispersant.

9. A slip-and levelling agent according to claim 2 , wherein A is represented by formula I,

wherein

R 1 is a moiety selected from the group consisting of C n F 2n+1 —(CH 2 ) m —, AC n F 2n —(CH 2 ) m —, C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —, AC n F 2n —(CH 2 ) m —(OCH 2 CHR 5 ) p , C n F 2n+1 —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —(OCH 2 CHR 5 ) p —X and C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —X—;

wherein A is selected from the group consisting of H, Cl, Br, I, C 1-12 alkyls and OC 1-12 alkyls, wherein 4≦n≦20, 0≦m≦4 and 0≦p≦20, wherein X is a spacer moiety selected from the group consisting of esters, amides, sulphonamides, mercapto groups, polyurethane groups and alkyl groups,

R 2 is selected from the group consisting of H, metal moieties, (alkyl)ammonium moieties, alkyl groups, C n F 2n+1 —(CH 2 ) m —, AC n F 2n —(CH 2 ) m —, C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —, AC n F 2n —(CH 2 ) m (OCH 2 CHR 5 ) p , C n F 2n+1 —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —X—, AC n F 2n —(CH 2 ) m —(OCH 2 CHR 5 ) p —X and C n F 2n+1 —(CH 2 ) m —(OCH 2 CHR 5 ) p —X—; wherein A is selected from the group consisting of H, Cl, Br, I, C 1-12 alkyls and OC 1-12 alkyls, wherein 4≦n≦20, 0≦m≦4 and 0≦p≦20, wherein X is a spacer moiety selected from the group consisting of esters, amides, sulphoamides, mercapto groups, polyurethane groups and alkyl groups,

R 3 and R 4 are independently selected from the group consisting of H, alkyl-groups and phenyl-groups and wherein R 5 is selected from the group consisting of H and methyl groups.

10. A slip-and levelling agent according to claim 9 , wherein

R 1 is a moiety selected from the group consisting of C n F 2n+1 —(CH 2 ) m —, C n F 2n+1 —(CH 2 ) m —(OCH 2 CH 2 ) m , C n F 2n+1 —(CH 2 ) m —X— and C n F 2n+1 —(CH 2 ) m —(OCH 2 CH 2 ) p —X— wherein n is 4 or 6 or 8;

m is 1, 2 or 3; and p is 0, 6, 7 or 8;

R 3 and R 4 are H;

X is —O—CO(CH 2 ) x — or —CO—O(CH 2 ) x —, —NRCO(CH 2 ) x — or —CONR(CH 2 ) x —, —SO 2 NR(CH 2 ) x —; —S(CH 2 ) x —, —O—CONH(CH 2 ) x — or —NH—CO 2 (CH 2 ) x —, —O(CRHCH 2 ) x —, —(CRH) x — or —CR═CR(CRH) x —, wherein x=0-6 and R═H or C 1-6 alkyl.

11. A slip-and levelling agent according to claim 5 , wherein 90-100% of the fluorinated monomeric units A are mono-esters.

12. A slip-and levelling agent according to claim 2 , wherein at least 50% of the fluorinated monomeric units A are mono-esters.

13. A slip-and levelling agent according to claim 12 , wherein 90-100% of the fluorinated monomeric units A are mono-esters.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2011
From: CIBA CORPORATION
To: BASF SE
Reel/Frame 025686/0722 →
CHANGE OF NAME Recorded Jan 24, 2011
From: CIBA SPECIALITY CHEMICAL CORPORATION
To: CIBA CORPORATION
Reel/Frame 025686/0747 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 24, 2009
From: ENGELBRECHT, LOTHAR ALEXANDER; PIRRUNG, FRANK OLIVER HEINRICH; HARBERS, PETRUS JOHANNES; NOORDAM, AREND; PHILIPOOM, MARTIN
To: CIBA SPECIALTY CHEMICALS CORP.
Reel/Frame 022591/0968 →
Priority Claims (2)
EP 05104525 · May 26, 2005 · regional
EP 06110309 · Feb 23, 2006 · regional
Continuity (1)
Related Publication 20090186979A1 · Jul 23, 2009