IP Library Granted Patent US 9,453,143
Granted Patent B2
US 9,453,143 · App. 13/261,892 · Granted Sep 27, 2016

Use of modified polysiloxanes in coating material compositions and molding materials

Inventors: Marc Hans (Wesel, DE); Wojciech Jaunky (Wesel, DE); Petra Della Valentina (Dinslaken, DE); Jüergen Hartmann (Oberhausen, DE); Verena Wintermeyer (Krefeld, DE)
Assignee: BYK-Chemie GmbH
C09D183/14C08G77/452C08G77/54C09D183/10
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Quick Facts
Patent No.
US 9,453,143
App. No.
13/261,892
Granted
Sep 27, 2016
Kind
B2
Abstract

The present invention relates to the use of modified polysiloxanes in thermally curing coating material compositions and molding materials, and to thermally curing coating material compositions and molding materials comprising modified polysiloxanes. The present invention also relates to coatings on a substrate, and to moldings which have been produced with such a coating material composition or molding material.

Claims (35)

1. A composition comprising a thermally curing coating material and polysiloxane-polyoxazoline copolymers or a thermally curing molding compound composition and polysiloxane-polyoxazoline copolymers,

wherein the polysiloxane-polyoxazoline copolymers comprise polysiloxane blocks which consist of the following structural formula (II)

where

o is 5 to 200 and p is 5 to 200;

R 1 and R 2 independently of one another are saturated linear alkyl radicals having 1 to 6 carbon atoms, saturated branched alkyl radicals having 3 to 6 carbon atoms, saturated cyclic alkyl radicals having 4 to 6 carbon atoms, linear alkenyl radicals having 2 to 6 carbon atoms, branched alkenyl radicals having 3 to 6 carbon atoms, cyclic alkenyl radicals having 4 to 6 carbon atoms, aryl radicals, alkylaryl radicals or arylalkyl radicals having 6 to 12 carbon atoms, the radicals being optionally halogen-substituted;

R 5 and R 6 independently of one another are R 1 or R 2 or are R 4 [SiR 1 R 2 O] q , in which q is 1 to 400 and

R 4 is a saturated linear alkyl radical having 1 to 30 carbon atoms; a branched alkyl radical having 3 to 30 carbon atoms; a cyclic alkyl radical having 4 to 30 carbon atoms; or an aryl radical, an alkylaryl radical, or an arylalkyl radical having 6 to 30 carbon atoms, the radicals being optionally halogen-substituted;

A and C independently of one another are B or R 4 , and

B is a linear or branched alkyl or aralkyl radical or a linker having a linear or branched alkylene or aralkylene structure which may comprise nitrogen and oxygen atoms, with the proviso that there is at least one such linker per siloxane block (II),

wherein the linker is an amino-functional linker (CH 2 ) t —R 10 —R 11 —R 12 —NR 14 —, where t is 2 to 30;

R 10 is (CH 2 ) u , O, S, NR 14 or C 6 (R 15 ) 4 , where u is 0 or 1 and R 14 is hydrogen, a saturated linear alkyl radical having 1 to 6 carbon atoms, a saturated branched alkyl radical having 3 to 6 carbon atoms, an aryl radical, an alkylaryl radical or an arylalkyl radical having 6 to 9 carbon atoms, and R 15 is hydrogen, or an alkyl radical having 1 to 6 carbon atoms:

R 11 is (CH 2 ) v or (CH 2 CHR 16 O) w , where v is 0 to 30 and w is 0 to 50 and R 16 is hydrogen, a saturated linear alkyl radical having 1 to 6 carbon atoms, a saturated branched alkyl radical having 3 to 6 carbon atoms, or a saturated cyclic alkyl radical having 4 to 6 carbon atoms; and

R 12 is (CH 2 ) x , in which x is 0 to 3:

wherein the composition comprises 0.005 to 5 wt % of the polysiloxane-polyoxazoline copolymers, based on the overall composition comprising the coating material and the polysiloxane-polyoxazoline copolymers or the overall composition comprising the molding compound composition and the polysiloxane-polyoxazoline copolymers,

wherein the composition when cured exhibits at least one of high scratch resistance, low slip resistance, substantially reduced emergence of the polysiloxane-polyoxazoline copolymers from the cured composition, and effective dirt repellence in conjunction with effective recoatability; and

wherein the composition cures at temperatures above 100° C. to about 400° C.

2. The composition of claim 1 , wherein the linker is (CH 2 ) 3 —NH—.

3. The composition of claim 1 , wherein the coating material comprises at least one of polyurethane, polyester, polyesterpolyol, polyacrylate, polymethacrylate, mixed poly(meth)acrylate, polyesteracrylate, epoxy, phenol/formaldehyde, poly(amide-imide) and alkyd resins as binders; and at least one of amino resins, monomeric and polymeric polyisocyanates and hydroxyalkylamides as crosslinking agents.

4. The composition of claim 1 , wherein the molding compound comprises at least one of unsaturated polyester resins, vinyl resins, polyurethane resins, polyamide resins, phenol/formaldehyde resins and epoxy resins.

5. The composition of claim 4 , wherein the molding compound comprises at least one of unsaturated polyester resins and/or vinyl resins and the composition further comprises at least one of polystyrene, polyvinyl acetate, polymethyl methacrylate and styrene/butadiene copolymers.

6. A coated substrate comprising the composition of claim 1 .

7. A composition comprising a thermally curing coating material and polysiloxane-polyoxazoline copolymers or a thermally curing molding compound composition and polysiloxane-polyoxazoline copolymers,

wherein the polysiloxane-polyoxazoline copolymers comprise polysiloxane blocks which consist of the following structural formula (II)

where

o is 5 to 200 and p is 5 to 200;

R 1 and R 2 independently of one another are saturated linear alkyl radicals having 1 to 6 carbon atoms, saturated branched alkyl radicals having 3 to 6 carbon atoms, saturated cyclic alkyl radicals having 4 to 6 carbon atoms, linear alkenyl radicals having 2 to 6 carbon atoms, branched alkenyl radicals having 3 to 6 carbon atoms, cyclic alkenyl radicals having 4 to 6 carbon atoms, aryl radicals, alkylaryl radicals or arylalkyl radicals having 6 to 12 carbon atoms, the radicals being optionally halogen-substituted;

R 5 and R 6 independently of one another are R 1 or R 2 or are R 4 [SiR 1 R 2 O] q , in which q is 1 to 400 and

R 4 is a saturated linear alkyl radical having 1 to 30 carbon atoms; a branched alkyl radical having 3 to 30 carbon atoms; a cyclic alkyl radical having 4 to 30 carbon atoms; or an aryl radical, an alkylaryl radical, or an arylalkyl radical having 6 to 30 carbon atoms, the radicals being optionally halogen-substituted;

A and C independently of one another are B or R 4 , and

B is a linear or branched alkyl or aralkyl radical or a linker having a linear or branched alkylene or aralkylene structure which may comprise nitrogen and oxygen atoms, with the proviso that there is at least one such linker per siloxane block (II),

wherein the linker is an amino-functional linker (CH 2 ) t —R 10 —R 11 —R 12 —NR 14 —, where t is 2 to 30;

R 10 is (CH 2 ) u , O, S, NR 14 or C 6 (R 15 ) 4 , where u is 0 or 1 and R 14 is hydrogen, a saturated linear alkyl radical having 1 to 6 carbon atoms, a saturated branched alkyl radical having 3 to 6 carbon atoms, an aryl radical, an alkylaryl radical or an arylalkyl radical having 6 to 9 carbon atoms, and R 15 is hydrogen, or an alkyl radical having 1 to 6 carbon atoms;

R 11 is (CH 2 ) v or (CH 2 CHR 16 O) w , where v is 0 to 30 and w is 0 to 50 and R 16 is hydrogen, a saturated linear alkyl radical having 1 to 6 carbon atoms, a saturated branched alkyl radical having 3 to 6 carbon atoms, or a saturated cyclic alkyl radical having 4 to 6 carbon atoms; and

R 12 is (CH 2 ) x , in which x is 0 to 3:

wherein the composition comprises 0.005 to 5 wt % of the polysiloxane-polyoxazoline copolymers, based on the overall composition comprising the coating material and the polysiloxane-polyoxazoline copolymers or the overall composition comprising the molding compound composition and the polysiloxane-polyoxazoline copolymers, wherein the composition cures at temperatures from above 100° C. to about 400° C.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2015
From: HANS, MARC; JAUNKY, WOJCIECH; DELLA VALENTINA, PETRA; HARTMANN, JÜRGEN; WINTERMEYER, VERENA
To: BYK-CHEMIE GMBH
Reel/Frame 036385/0201 →
Priority Claims (1)
EP 11189026 · Nov 14, 2011 · regional
Continuity (1)
Related Publication 20140296417A1 · Oct 2, 2014