Latently-curable organosilicone release coating composition

• US 4,533,575 A
• Filed: 12/18/1984
• Issued: 08/06/1985
• Est. Priority Date: 09/23/1983
• Status: Expired due to Term

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Melancon, Kurt C.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/683,212
• Time in Patent Office: 231 Days
• Field of Search: 427/387, 428/447, 428/450, 428/451, 428/452, 528/15, 528/31, 528/32, 525/478
• US Class Current: 427/387
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/24 halogen-containing groups
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08G 77/80 Siloxanes having aromatic substituents, e.g. phenyl side groups
• CPC Class Codes: C08L 2666/34 Oxygen-containing compounds, including ammonium and metal salts
• CPC Class Codes: C08L 2666/36 Nitrogen-containing compounds
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31667 Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product

Abstract

A latently-curable, organosilicone composition comprises a metal catalyzed organosilicone composition capable of undergoing hydrosilation and, as hydrosilation inhibitor, an organic monohydrogen derivative of an unsaturated aliphatic 1,4-dicarboxylic acid, i.e., maleic acid or acetylene dicarboxylic acid. The organic monohydrogen derivatives of use in this invention effectively inhibit catalyzed hydrosilation reactions at low or room temperature while allowing efficient hydrosilation reaction rates to occur at elevated temperatures. These monohydrogen derivatives perform their inhibitive function effectively at low concentration. The latently curable composition may be coated on a substrate to provide a release surface for an adjacent adhesive layer.

Claims

1. A process comprising the steps:

(a) providing a latently-curable organosilicone composition by mixing at ambient temperatures

(1) an ethylenically-unsaturated polysiloxane,

(2) a polyhydrosiloxane,

(3) an effective amount of a metal-containing hydrosilation catalyst to facilitate the addition cure reaction of components (1) and (2), and

(4) an amount of a hydrosilation inhibitor 1,4-dicarboxylic acid compound sufficient to inhibit premature gelation of the mixture of components (1), (2), and (3) at low, ambient or room temperature but insufficient in amount to prevent hydrosilation of the mixture at an elevated temperature, said hydrosilation inhibitor having the structural formula ##STR10## wherein R² is ethynylene or cis-ethenylene;

R³ is a saturated or unsaturated organic group having 1 to 12 carbon atoms which is unsubstituted or substituted by 1 to 23 halogen atoms, and has up to 25 hydrogen atoms; and

X is --O-- or ##STR11## in which R⁴ is the same as defined for R³, and R³ and R⁴ together with the N can form a saturated azacyclic ring,

(b) coating a substrate with said admixture, and

(c) elevating the temperature of the resulting coated admixture when cure of said admixture is to be effected.

2. The process according to claim 1 wherein said latently-curable organosilicone composition further comprises 2 to 100 parts of a release modifier per 100 parts of said composition.

3. The process according to claim 2 wherein said release modifier is an MQ resin.

4. A release liner for adhesive materials comprising a substrate coated on at least one surface thereof with a cured adhesive composition comprising the following components:

(a) an ethylenically-unsaturated polysiloxane,

(b) a polyhydrosiloxane,

(c) an amount of a platinum or other metal-containing hydrosilation catalyst sufficient to facilitate the reaction of components (a) and (b), and

(d) an amount of an organic hydrosilation inhibitor sufficient to inhibit premature gelation of the mixture of components (a), (b), and (c) at low, ambient or room temperature but insufficient in amount to prevent hydrosilation of the mixture at an elevated temperature, said organic hydrosilation inhibitor having the structural formula ##STR12## wherein R² is ethynylene or cis-etheynlene;

R³ is a saturated or unsaturated organic group having 1 to 12 carbon atoms which is unsubstituted or substituted by 1 to 23 halogen atoms, and has up to 25 hydrogen atoms, and 0 to 5 non-peroxidic catenary oxygen atoms; and

X is --O-- or ##STR13## in which R⁴ is the same as defined for R³, and R³ and R⁴ together can form an alkylene group which with the N can form a 5- or 6-atom membered saturated azacyclic ring.

5. The release liner according to claim 4 wherein in said adhesive composition said hydrosilation inhibitor is 2-ethylhexyl hydrogen maleate.

6. The release liner for adhesive material according to claim 4 bearing on each surface thereof said cured adhesive composition, said composition on at least one of said surfaces further comprising a release modifier so as to provide an adhesive release differential of at least 10 percent.

7. The release liner of claim 6 wherein said release modifier is an MQ resin.

8. The release liner for adhesive material according to claim 6 wherein in the composition on one surface R is methyl, and in the composition on the second surface 2 to 50 mole percent of R is phenyl and the remaining R is methyl.