# US 2017/0283671 A1 · 1K High Temperature Debondable Adhesive > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2017/0283671 A1 - Document ID: US20170283671A1 - Status: Published application - Kind: A1 - Application number: 15/629,804 - Filed: 2017-06-22 - Published: 2017-10-05 - Earliest claimed: 2014-12-23 - Applicants: Henkel AG & Co. KGaA; Henkel IP & Holding GmbH - Inventors: Stephen Hynes; Chunyu Sun; Jiangbo Ouyang; JinQian Chen - Web page: https://patentgrep.com/patent/US20170283671A1 ## CPC - C09J 183/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09J183/10 takes precedence) - B32B 37/12: characterised by using adhesives - C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen - C09J 5/06: involving heating of the applied adhesive - B32B 2037/1253: {curable adhesive} - C08G 77/20: containing silicon bound to unsaturated aliphatic groups - C08G 77/28: sulfur-containing groups - C08G 77/50: by carbon linkages - C08K 5/14: Peroxides - C09J 2301/416: use of irradiation - C09J 2301/502: process for debonding adherents - C09J 2483/00: Presence of polysiloxane - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract The present disclosure provides 1k high temperature debondable adhesives for use in the temporary attachment of one substrate to another substrate. The adhesives composition comprising(a) 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane, or the hydrosilation reaction product of the reaction between the vinyl groups on 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane and the terminal Si—H hydrogens on a silane or siloxane having terminal Si—H groups, or a mixture of a hydrosilation reaction product of the reaction between the vinyl groups on 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane and the terminal Si—H hydrogens on a silane or siloxane having terminal Si—H groups and a hydrosilation reaction product of the reaction between the vinyl groups on vinyl polysiloxane and the terminal Si—H hydrogens on a silane or siloxane having terminal Si—H groups, and (b) mercapto-crosslinker. The adhesive composition is cured by UVNis/LED or thermal or combined and is cured faster requiring lower energy. The present disclosure also provides assemblies including such an adhesive and methods of using the adhesives. ## Claims ### Claim 1 A 1k high temperature debondable adhesive composition comprising (a) 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane; or the hydrosilation reaction product of the reaction between the vinyl groups on 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane and the terminal Si—H hydrogens on a silane or siloxane having terminal Si—H groups; or a mixture of a hydrosilation reaction product of the reaction between the vinyl groups on 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane and the terminal Si—H hydrogens on a silane or siloxane having terminal Si—H groups and a hydrosilation reaction product of the reaction between the vinyl groups on vinyl polysiloxane and the terminal Si—H hydrogens on a silane or siloxane having terminal Si—H groups, and (b) mercapto-crosslinker. ### Claim 2 (depends on 1) The debondable adhesive composition according to claim 1, wherein the silane or siloxane having terminal. Si—H hydrogens has the structure wherein R is selected from the group consisting of a C1 to C10 alkyl group, an aryl group, an oxygen, —(O—SiMe2)n—O—, —(O—SiAr2)n—O—, —(O—SiMeAr)n—O—, and a combination of any of these groups; n is an integer of at least 1; Me is a methyl group; Ar is an aryl group; and each of R1, R2, R3, R4, R5, and R6, is independently selected from a C1 to C10 alkyl group or an aryl group. ### Claim 3 (depends on 2) The debondable adhesive composition according to claim 2, wherein the silane or siloxane having terminal Si—H hydrogens is selected from the group consisting of polydialkylsiloxane, polyalkylaryl siloxane, tetraalkyldisiloxane and polydiaryl siloxane. ### Claim 4 (depends on 1) The debondable adhesive composition according to claim 1, wherein the siloxane having substituted vinyl group has the structure wherein R7, R8 and R9 are each independently selected from the group consisting of C1 to C10 alkyl group or aryl group, and m, n denote positive integers. ### Claim 5 (depends on 4) The debondable adhesive composition according to claim 4, wherein the vinyl polysiloxane is selected from the group consisting of copolymer of methylvinylsiloxane and dimethylsiloxane; copolymer of methylvinylsiloxane and diethylsiloxane; copolymer of methylvinylsiloxane and methylethylsiloxane; copolymer of ethylvinylsiloxane and dimethylsiloxane; copolymer of ethylvinylsiloxane and diethylsiloxane; copolymer of ethylvinylsiloxane and methylethylsiloxane; copolymer of propylvinylsiloxane and dimethylsiloxane; copolymer of propylvinylsiloxane and diethylsiloxane; copolymer of propylvinylsiloxane and methylethylsiloxane; copolymer of phenylvinylsiloxane and dimethylsiloxane; copolymer of phenylvinylsiloxane and diethylsiloxane; copolymer of phenylvinylsiloxane and methylethylsiloxane; and combinations thereof. ### Claim 6 (depends on 1) The debondable adhesive composition according to claim 1, wherein the mercapto-crosslinker is selected from the group consisting of hydrogen sulphide; tricarballylic mercaptan; isopentyl tetramercaptan; m-triethanethiol benzene; p-diethanethiol benzene; isopentyl tetraacetatemercaptan; mercapto-polysiloxane with structure of wherein R10, R11, R12, R13 are each independently selected from the group consisting of C1 to C10 alkyl group or aryl group, x denotes an integer more than 1, y denotes 0 or a positive integer; and combinations thereof. ### Claim 7 (depends on 1) The debondable adhesive composition according to claim 1, wherein the mercapto-crosslinker has the structure wherein, m and n are each positive integer numbers. ### Claim 8 (depends on 1) The debondable adhesive composition according to claim 1; further comprising a radical curing initiator (c). ### Claim 9 (depends on 1) The debondable adhesive composition according to claim 1, further comprising a radical curing initiator selected from the group consisting of a-hydroxy ketones; benzophenones; phenyl glyoxylic acids; acyl-phosphine oxides; bis-acyl-phosphine oxides; dicumene peroxide; cumene hydroperoxide; 2-hydroxy-2-methyl-1-phenyl propan-1-one; and combinations thereof. ### Claim 10 (depends on 1) The debondable adhesive composition according to claim 1, further comprising filler (d). ### Claim 11 (depends on 1) The debondable adhesive composition according to claim 1, wherein the (a) reaction product is selected from at least one of the structures: ### Claim 12 (depends on 1) The debondable adhesive composition according to claim 1, comprising: 50 to 95 wt. % of the (a) 1,3,5,7-tetravinyl-113,5,7-tetramethylcyclotetrasiloxane; or the hydrosilation reaction product; 5 to 50 wt.% of the (b) mercapto-crosslinker; optionally 0.1 to 5 wt. % of a radical initiator; and optionally 0.5 to 40 wt. % of filler; wherein all wt. % are by weight of the total composition. ### Claim 13 (depends on 1) Cured reaction products of the debondable adhesive composition according to claim 1. ### Claim 14 (depends on 1) Cured reaction products of the debondable adhesive composition according to claim 1, wherein the cured reaction products have a thermal stability weight loss of less than 5.5% at 400° C. and a mechanical debond peel force (ASTM D2095) of less than 0.5 MPa. ### Claim 15 (depends on 1) An assembly comprising a substrate and a carrier, including the debondable adhesive composition according to claim 1 disposed between the carrier and the substrate. ### Claim 16 (depends on 1) A method for bonding a substrate to a carrier comprises steps of: (i) providing a substrate and a carrier; (ii) disposing the debondable adhesive composition according to claim 1 on the substrate and/or the carrier; (iii) contacting the substrate and carrier so that the debondable adhesive composition is disposed between the carrier and the substrate, forming an assembly; and (iv) radically curing the debondable adhesive by heating the assembly, or exposing the assembly to radiation, or exposing the assembly to radiation followed by heating. ### Claim 17 (depends on 1) A method for debonding a substrate from a carrier comprises steps of: (i) providing a substrate bonded to a carrier by cured reaction products of the debondable adhesive composition according to claim 1; and (ii) mechanically separating the substrate and the carrier, optionally after allowing the assembly to come to ambient temperature and/or one or more steps of processing the substrate.