IP Library Granted Patent US 11,001,737
Granted Patent B2
US 11,001,737 · App. 16/312,330 · Granted May 11, 2021

Permeation-inhibiting release coating

Inventors: Juergen Pomorin (Essen, DE); Dieter Grauer (Remseck, DE); Hardi Doehler (Essen, DE); Ingo Schoenemann (Muelheim an der Ruhr, DE); Mike Brand (Essen, DE)
Assignee: Evonik Operations GmbH
C09J183/10B32B27/10B32B27/283C08F283/124C08G77/442C09D183/10D21H19/32B32B2307/7265B32B2383/00B32B2405/00B32B2554/00C08G77/20C09J2483/005
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Quick Facts
Patent No.
US 11,001,737
App. No.
16/312,330
Granted
May 11, 2021
Kind
B2
Abstract

The invention relates to compositions containing at least one siloxane which comprises ethylenically unsaturated, radically polymerizing groups, and at least one hydrocarbon with ethylenically unsaturated, radically polymerizing groups, which have, when used as a separating coating, an improved barrier effect.

Claims (64)

1. A permeation-inhibiting release coating obtained by curing a composition comprising components (I), (II) and optionally (III):

(I) 20 to 90% by weight, based on a sum total of components (I), (II) and (III) of the composition, comprises silicon-free hydrocarbons which consist of carbon, hydrogen and oxygen and which have at least one ethylenically unsaturated free-radically polymerizable group and has no oxyethylene groups,

wherein component (I) has a hydrocarbon to an extent of at least 80 and up to 100% by weight, based on a total mass of component (I), having two or more ethylenically unsaturated free-radically polymerizable groups and at least one aromatic group;

(II) 10 to 90% by weight, based on a sum total of components (I), (II) and (III) of the composition, of one or more organomodified silicones having 50 to 500 silicon atoms, wherein 0.4 to 10% of silicon atoms optionally have ethylenically unsaturated free-radically polymerizable groups; and

(III) 0 to 70% by weight, based on a sum total of components (I), (II) and (III) of the composition, of one or more organomodified silicones having 4 to 40 silicon atoms, wherein 15 to 100% of silicon atoms have ethylenically unsaturated free-radically polymerizable groups; and

optionally an additive;

wherein the permeation-inhibiting release coating has a permeation barrier against butyl acetate, and the permeation-inhibiting release coating has a delta-L* value of from 1 to 20.

2. The permeation-inhibiting release coating according claim 1 , wherein the delta-L* value is from 1 to 18.

3. The permeation-inhibiting release coating according to claim 1 , wherein the permeation-inhibiting release coating has a release force of at most 80 cN/2.5 cm, wherein a lower value of the release force is greater than 1 cN/2.5 cm, and wherein the release force is determined in accordance with FINAT Handbook 8th Edition, The Hague/NI, 2009 under the designation FTM 10.

4. The permeation-inhibiting release coating according to claim 1 , wherein the ethylenically unsaturated free-radically polymerizable groups in components (I) and (III) and/or ethylenically unsaturated free-radically polymerizable groups, if present in component (II) are groups selected from an acrylic ester function, a methacrylic ester function or both.

5. The permeation-inhibiting release coating according to claim 1 , wherein

component (I) is present at 20 to 70% by weight,

component (II) is present at 30 to 80% by weight, and

component (III) is present at 0 to 40% by weight, all based on the sum total of components (I), (II) and (III) of the composition.

6. The permeation-inhibiting release coating according to claim 1 , wherein the component (II) comprises a compound of formula (I):

M 1 a M 2 b D 1 c D 2 d   (I)

wherein M 1 =[R 1 3 SiO 1/2 ],

M 2 =[R 1 2 R 2 SiO 1/2 ],

D 2 =[R 1 2 SiO 2/2 ],

D 2 =[R 1 R 2 SiO 2/2 ],

a=0to 2,

b=0to 2, and a+b=2,

c=50 to 490,

d=0 to 15, and

a ratio of the sum (b+d) to the sum (c+d+2) is from 0.004 up to 0.1,

the sum (c+d+2) is 50 to 500,

R 1 denotes identical or different aliphatic hydrocarbons having 1 to 10 carbon atoms or aromatic hydrocarbons having 6 to 12 carbon atoms, and

R 2 denotes identical or different hydrocarbons which have 1 to 5 identical or different ester functions, and the hydrocarbon is linear, cyclic, branched and/or aromatic.

7. The permeation-inhibiting release coating according to claim 1 , wherein the component (III) comprises a compound of formula (II):

M 1 e M 3 f D 1 g D 3 h   (II)

wherein

M 1 =[R 1 3 SiO 1/2 ],

M 3 =[R 1 2 R 3 SiO 1/2 ],

D 1 =[R 1 2 SiO 2/2 ],

D 3 =[R 1 R 3 SiO 2/2 ],

e=0 to 2 ,

f=0 to 2, and e+f=2,

g=0 to 38,

h=0 to 20 and

a ratio of the sum (f+h) to the sum (g+h+2) is from 0.15 up to 1,

the sum (g+h+2) is from 4 to 40,

R 1 denotes identical or different aliphatic hydrocarbons having 1 to 10 carbon atoms or aromatic hydrocarbons having 6 to 12 carbon atoms, and

R 3 denotes identical or different hydrocarbons which have 1 to 5 identical or different ester functions, and the hydrocarbon is linear, cyclic, branched and/or aromatic.

8. The permeation-inhibiting release coating according to claim 1 , wherein component (III) comprises ester groups that are not free-radically polymerizable.

9. The permeation-inhibiting release coating according to claim 1 , wherein ester groups that are not free-radically polymerizable are not present in component (II) and ester groups that are not free-radically polymerizable are present in component (III) in a numerical proportion of 5 to 15%, based on the number of all ester functions in component (III).

10. A method for preparing the permeation-inhibiting release coating according to claim 1 , the method comprising:

radiation-curing the permeation-inhibiting release coating.

11. A topcoat for thermal papers, comprising:

a permeation-inhibiting release coating obtained by curing a composition comprising components (I), (II) and optionally (III):

(I) 20 to 90% by weight, based on a sum total of components (I), (II) and (III) of the composition, comprises silicon-free hydrocarbons which consist of carbon, hydrogen and oxygen and which have at least one ethylenically unsaturated free-radically polymerizable group and have no oxyethylene groups,

wherein component (I) has a hydrocarbon to an extent of at least 80 and up to 100% by weight, based on a total mass of component (I), having two or more ethylenically unsaturated free-radically polymerizable groups and at least one aromatic group;

(II) 10 to 90% by weight, based on a sum total of components (I), (II) and (III) of the composition, of one or more organomodified silicones having 50 to 500 silicon atoms; and

(III) 0 to 70% by weight, based on a sum total of components (I), (II) and (III) of the composition, of one or more organomodified silicones having 4 to 40 silicon atoms, wherein 15 to 100% of silicon atoms have ethylenically unsaturated free-radically polymerizable groups; and

optionally an additive;

wherein the permeation-inhibiting release coating has a permeation barrier against butyl acetate, and the permeation-inhibiting release coating has a delta-L* value of from 1 to 20.

12. The topcoat according to claim 11 , wherein the thermal paper is self-adhesive and is designed as adhesive tape.

13. A radiation-curing coating composition for preparing a permeation-inhibiting release coating having a permeation barrier against butyl acetate, the permeation-inhibiting release coating comprising components (I), (II) and optionally (III):

(I) 20 to 90% by weight, based on a sum total of components (I), (II) and (III) of the composition, comprises silicon-free hydrocarbons which consist of carbon, hydrogen and oxygen and which have at least one ethylenically unsaturated free-radically polymerizable group and have no oxyethylene groups,

wherein component (I) has a hydrocarbon to an extent of at least 80 and up to 100% by weight, based on a total mass of component (I), having two or more ethylenically unsaturated free-radically polymerizable groups and at least one aromatic group;

(II) 10 to 90% by weight, based on a sum total of components (I), (II) and (III) of the composition, of one or more organomodified silicones having 50 to 500 silicon atoms; and

(III) 0 to 70% by weight, based on a sum total of components (I), (II) and (III) of the composition, of one or more organomodified silicones having 4 to 40 silicon atoms, wherein 15 to 100% of the silicon atoms have ethylenically unsaturated free-radically polymerizable groups; and

an additive,

wherein the permeation-inhibiting release coating has a delta-L* value of from 1 to 20.

14. The radiation-curing coating composition according to claim 13 , wherein the additive is at least one selected from the group consisting of a photoinitiator, a photosensitizer, a filler, a pigment, a solvent, a phosphorus-containing compound which polymerizes under UV light, a stabilizer, an anti-misting additive and an amine synergist.

Assignments (2)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2018
From: POMORIN, JUERGEN; GRAUER, DIETER; DOEHLER, HARDI; SCHOENEMANN, INGO; BRAND, MIKE
To: EVONIK DEGUSSA GMBH
Reel/Frame 047838/0935 →
Priority Claims (1)
EP 16176339 · Jun 27, 2016 · regional
Continuity (1)
Related Publication 20190161656A1 · May 30, 2019
Cited By (1)
US 12,674,030