# US 10,308,755 B2 · Sheet-forming body, adhesive sheet, and laminate

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- Number: US 10,308,755 B2
- Document ID: US10308755B2
- Status: Granted
- Kind: B2
- Application number: 15/303,802
- Filed: 2015-03-31
- Published: 2017-02-09
- Granted: 2019-06-04
- Earliest claimed: 2014-04-18
- Assignees: Bridgestone Corporation
- Applicants: Bridgestone Corporation
- Inventors: Takenobu Ishihara; Shuyou Akama; Atsushi Hara
- Web page: https://patentgrep.com/patent/US10308755B2

## CPC

- C08G 18/3876: {containing mercapto groups}
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 15/095: comprising polyurethanes
- B32B 15/18: comprising iron or steel {(B32B15/011, B32B15/012 and B32B15/013 take precedence)}
- B32B 25/08: of synthetic resin
- B32B 25/12: comprising natural rubber
- B32B 25/14: comprising {synthetic rubber copolymers (B32B25/18 and B32B25/20 take precedence)}
- B32B 27/28: comprising synthetic resins not wholly covered by any one of the sub-groups {B32B27/30 - B32B27/42}
- C08G 18/092: {oligomerisation to isocyanurate groups}
- C08G 18/1808: {having alkylene polyamine groups}
- C08G 18/3855: {having sulfur}
- C08G 18/6453: {having sulfur}
- C08G 18/73: acyclic
- C08G 18/7831: {containing biuret groups}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08G 75/00: Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C09J 7/10: without carriers
- C09J 175/04: Polyurethanes
- C09J 181/00: Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- B32B 2250/03: 3 layers
- B32B 2250/24: All layers being polymeric
- B32B 2270/00: Resin or rubber layer containing a blend of at least two different polymers
- C09J 175/06: from polyesters
- C09J 2475/00: Presence of polyurethane
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- 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)

## Abstract

The present invention provides a sheet-forming body containing a thiourethane bond-having compound and a thiol group-having compound, wherein, in an IR absorption spectrum thereof, the ratio of the peak intensity A of the absorption peak based on the carbonyl group in the thiourethane bond to the peak intensity B of the absorption peak based on the thiol group (A/B) is 20 or more and 250 or less. Using the sheet-forming body, rubber members, especially vulcanized rubber members can be strongly bonded, and the sheet-forming body and an adhesive sheet, which are excellent in handleability and workability, and a laminate produced by bonding rubber layers using the sheet-forming body are provided.

## Claims

### Claim 1

A laminate comprising two or more layers bonded to each other, wherein:
at least one layer is a rubber layer, and
the at least one rubber layer is adhered to the adjacent layer via a sheet-forming body comprising a thiourethane bond-having compound and a thiol group-having compound, wherein:
in an IR absorption spectrum thereof, the ratio of the peak intensity A of the absorption peak based on the carbonyl group in the thiourethane bond to the peak intensity B of the absorption peak based on the thiol group (A/B) is 20 or more and 250 or less.

### Claim 2 (depends on 1)

The laminate according to claim 1, wherein at least a polythiol compound (A) and an isocyanate group-containing compound (B) are blended.

### Claim 3 (depends on 2)

The laminate according to claim 2, wherein a radical generator (C) is further blended.

### Claim 4 (depends on 3)

The laminate according to claim 3, wherein the radical generator (C) is a thermal radical generator containing a peroxide.

### Claim 5 (depends on 3)

The laminate according to claim 3, wherein the content of the peroxide, as measured through liquid chromatography mass spectrometry, is 2% by mass or more.

### Claim 6 (depends on 2)

The laminate according to claim 2, wherein the ratio of the total molar number of the isocyanate group contained in the isocyanate group-containing compound (B) to the total molar number of the thiol group contained in the polythiol compound (A) (isocyanate group/thiol group) is 0.2 or more and 0.78 or less.

### Claim 7 (depends on 4)

The laminate according to claim 4, wherein the ratio of the total molar number of the radical generator (C) to the total molar number of the thiol group contained in the polythiol compound (A) (radical generator (C)/thiol group) is 0.025 or more.

### Claim 8 (depends on 1)

An adhesive sheet provided with the laminate of claim 1.