Release Coating Compositions and Articles Therefrom

Patent metadata

Field	Value
Publication number	US-2022010171-A1
Application number	US-201917289329-A
Country	US
Kind code	A1
Filing date	Dec 19, 2019
Priority date	Dec 21, 2018
Publication date	Jan 13, 2022
Grant date	—

Abstract

Described herein is a release coating composition, articles made with the release coating composition and methods of making a release liner. The release coating composition comprising: (i) a sulfonated polyester siloxane polymer derived from: (a) at least one organic diol monomer, (b) at least one organic diacid monomer, at least one diester monomer or mixtures thereof; (c) at least one carbinol terminated polydimethylsiloxane, at least one carboxy terminated polydimethylsiloxane or mixtures thereof; and (d) at least one ion salt on a sulfonate difunctional monomer; (ii) a water-soluble or water-dispersible second polymer; and (iii) a thermally activated curing system, comprising a multifunctional compound.

First claim

1 . A release coating composition comprising:
(i) a sulfonated polyester siloxane polymer derived from:
(a) at least one organic diol monomer;
(b) at least one organic diacid monomer, at least one diester monomer or mixtures thereof,
(c) at least one carbinol terminated polydimethylsiloxane, at least one carboxy terminated polydimethylsiloxane, or mixtures thereof, and
(d) at least one ion salt on a sulfonate difunctional monomer;
(ii) a water-soluble or water-dispersible second polymer; and (iii) a thermally activated curing system, comprising a multifunctional compound.

2 . The release coating composition of claim 1 , wherein the sulfonated polyester siloxane polymer is represented by the following randomly chemically attached segments:

wherein the segments m, n and o represent the random units of the sulfonated polyester siloxane polymer, and wherein the sum of m, n, and o is from about 10 to about 500; p represents the repeating segment of the polydimethylsiloxane and is from about 20 to about 150 units; R 1 is an arylene; R 2 is an alkylene; R 3 is an alkali arylene sulfonate or an alkali alkylene-sulfonate, and R 4 is an alkylene, and optionally, wherein R 1 contains from about 1 to about 18 carbon atoms, and R 2 contains a carbon chain length of from 2 to 36 carbon atoms.

3 . The release coating composition of claim 1 , wherein the ion salt of the sulfonate difunctional monomer comprises hydrogen, sodium, potassium, cesium, or rubidium salt of dimethyl-5-sulfo-isophthalate, 4-sulfo-phthalic acid, sulfo-terephthalic acid, dimethyl-sulfo-terephthalate, dialkyl-sulfo-terephthalate or combinations thereof.

4 . The release coating composition of claim 2 , wherein R 3 is an alkali arylenesulfonate of the formulas

wherein M is selected from at least one of hydrogen, lithium, sodium, potassium, rubidium, or cesium.

5 . The release coating composition of claim 1 , wherein the organic diol is ethylene glycol, 1,6-hexylene glycol, 1,4-cyclohexane dimethanol, neopentyl glycol, or mixtures thereof.

6 . The release coating composition of claim 1 , wherein the sulfonated polyester siloxane polymer is derived from 45 to 55 mole percent of the organic diol, wherein the organic diol is ethylene glycol, 1,6-hexylene glycol, 1,4-cyclohexane dimethanol, neopentyl glycol, or mixtures thereof.

7 . The release coating composition of claim 1 , wherein the organic diacid or diester is terephthalic acid, isophthalic acid, phthalic acid, maleic anhydride, dialkyl esters thereof, or mixtures thereof, wherein the organic diacid or diester each is selected in an amount of from 5 to 55 percent of the sulfonated polyester siloxane polymer.

8 . The release coating composition of claim 1 , wherein the sulfonated polyester siloxane polymer is comprised of 5 to 30 weight percent of the carbinol terminated polydimethylsiloxane or the carboxy terminated polydimethylsiloxane, wherein the carbinol terminated polydimethylsiloxane or the carboxy terminated polydimethylsiloxane is bis-(1,3-hydroxypropyl)-polydimethylsiloxane.

9 . The release coating composition of claim 1 , as represented by the following chemically bonded random segments

wherein the segments m, n and o represent the random units of the sulfonated polyester siloxane polymer and wherein the sum of m, n, and o is from about 10 to about 500; p represents the repeating segment of the polydimethylsiloxane and is from about 20 to about 150 units; R 1 is an arylene; R 2 is an alkylene, R 3 is an phenylenesulfonate, isophthalylene-5-sulfonate, terephthalylene-sulfonate, phthalylene-sulfonate, or naphthylene-sulfonate, and optionally wherein R 3 is of the formula

wherein M is hydrogen, an alkali (I) metal of lithium, sodium, potassium, rubidium, or cesium and R 4 is ethylene, propylene or butylene.

10 . The release coating composition of claim 1 , wherein the sulfonated polyester siloxane polymer is poly(ethylene terephthalate)-co-(1,4-cyclohexane dimethylene terephthalate)-co-(ethylene isophthalate)-co-(1,4-cyclohexane dimethylene isophthalate)-co-(ethylene 5-sulfoisophthalate)-co-(1,4-cyclohexane dimethylene 5-sulfoisophthalate)-co-(polydimethylsiloxane propylene terephthalate)-co-(polydimethylsiloxane propylene isophthalate)-co-(polydimethylsiloxane propylene 5-sulfoisophthalate) or poly(ethylene sebacate)-co-(2,2-dimethylpropylene sebacate)-co-(ethylene isophthalate)-co-(2,2-dimethylpropylene isophthalate)-co-(ethylene 5-sulfoisophthalate)-co-(2,2-dimethylpropylene 5-sulfoisophthalate)-co-(polydimethylsiloxane propylene sebacate)-co-(polydimethylsiloxane propylene isophthalate)-co-(polydimethylsiloxane propylene 5-sulfoisophthalate).

11 . The release coating composition of claim 1 , wherein the at least one organic diacid monomer or at least one diester monomer is selected from at least one of terephthalic acid, dimethyl terephthalate, and combinations thereof.

12 . The release coating composition of claim 1 , wherein the multifunctional compound comprises at least one of melamine, diazine, urea, cyclic ethylene urea, cyclic propylene urea, thiourea, cyclic ethylene thiourea, alkyl melamines, aryl melamines, benzo guanamines, guanamines, alkyl guanamines, aryl guanamines with an aldehyde, and combinations thereof.

13 . The release coating composition of claim 1 , wherein the multifunctional compound is present at from 0.1 to 2 percent solids by weight based on the weight of the release coating composition.

14 . The release coating composition of claim 1 , comprising less than 10 wt % of the multifunctional compound versus the sulfonated polyester siloxane polymer.

15 . The release coating composition of claim 1 , comprising 1 to 50 wt % of the water-soluble or water-dispersible second polymer versus the sulfonated polyester siloxane polymer.

16 . A coated substrate comprising:
A first layer disposed on a polyester substrate, wherein the first layer is a cured product of the release coating composition of claim 1 .

17 . The coated substrate of claim 16 , wherein the thickness of the layer is 50 nm to 0.5 micron.

18 . The coated substrate of claim 16 , wherein at least a portion of the layer interpenetrates the polyester substrate.

19 . A method of making a release coated article, the method comprising:
coating a substrate with the release coating composition according to claim 1 to form a coated article, and drawing the substrate in at least one of the longitudinal or machine direction and optionally wherein the coated article is drawn.

20 . The method of claim 19 , wherein the substrate is drawn prior to coating the substrate.

Assignees

• 3M Innovative Properties Co

Inventors

• Ho Victor
• Benson Karl E
• Huseby Kevin T
• Johnson Stephen A
• Clausen Anna
• Peterson Jeffrey A

Classifications

• C09D183/10 Primary

  Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00) · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• C08G77/445

  containing polyester sequences · CPC title

• C08G77/28

  sulfur-containing groups · CPC title

• C08G63/183

  Terephthalic acids · CPC title