Adhesive composition, a process of producing the adhesive composition, a bonding method using the adhesive composition, and a structure having the adhesive composition applied thereon

Patent metadata

Field	Value
Publication number	US-11634617-B2
Application number	US-201716478369-A
Country	US
Kind code	B2
Filing date	Dec 20, 2017
Priority date	Jan 31, 2017
Publication date	Apr 25, 2023
Grant date	Apr 25, 2023

Abstract

The present invention has for its object to provide an adhesive composition that is based on a naturally occurring material less likely to have adverse influences on the human body and has a tensile shear strength (adhesive strength) of at least 1 MPa with respect to a variety of adherends. The present invention provides an adhesive composition including at least a first pack and a second pack, wherein the first pack contains a tannic acid derivative in which a hydrogen atom in at least some hydroxyl group of tannic acid is substituted by a chain hydrocarbon group having at least one hydroxyl group, and the second pack contains a hydrocarbon having at least two cyanate groups or a derivative of the hydrocarbon.

First claim

What is claimed is:

1. An adhesive composition comprising at least a first pack and a second pack, wherein:
the first pack contains a tannic acid derivative in which a hydrogen atom in at least some hydroxyl group of tannic acid is substituted by a chain hydrocarbon group having a constitutional unit which results from ring-opening polymerization of a compound having a furan ring, and
the second pack contains a hydrocarbon having at least two cyanate groups or a derivative of the hydrocarbon.

2. The adhesive composition according to claim 1 , wherein the chain hydrocarbon group is derived from a compound having an epoxy group comprising a three-membered ring.

3. The adhesive composition according to claim 2 , wherein the compound having an epoxy group is one or more selected from the group consisting of propylene oxide, 1,2-epoxyhexane, 1,2-epoxyoctane, 1,2-epoxydecane, epibromohydrin, epichlorohydrin, epifluorohydrin, and epiiodohydrin.

4. The adhesive composition according to claim 1 , wherein the chain hydrocarbon group in the tannic acid derivative is grafted by the constitutional unit which results from ring-opening polymerization of the compound having the furan ring.

5. The adhesive composition according to claim 4 , wherein the compound having a furan ring is tetrahydro-furan or 2-methyltetrahydrofuran.

6. The adhesive composition according to claim 1 , wherein a molar ratio between the tannic acid and the chain hydrocarbon group is no less than 1:1 to no greater than 1:50.

7. The adhesive composition according to claim 1 , wherein the number of carbons in the hydrocarbon or hydrocarbon derivative in the second pack is no less than 2 to no greater than 64.

8. The adhesive composition according to claim 1 , wherein the second pack is one or more selected from the group consisting of hexamethylene diisocyanate, tetramethylene diisocyanate, diphenyl-methane diisocyanate, and isophorone diisocyanate.

9. The adhesive composition according to claim 1 , wherein in the tannic acid derivative, a hydrogen atom in some hydroxyl group positioned in a terminal aromatic ring of the tannic acid is substituted by the chain hydrocarbon group.

10. The adhesive composition according to claim 1 , comprising the first pack, the second pack, and a filler.

11. A structure, wherein a mixture of the first and second packs of the adhesive composition according to claim 1 is applied to at least a portion of an exposed surface thereof.

12. A process of producing an adhesive composition including at least a first pack and a second pack, comprising:
a step of providing tannic acid and a chain hydrocarbon having an epoxy group;
a step of producing the first pack by mixing together the tannic acid and the chain hydrocarbon having an epoxy group in a solvent containing a compound having a furan ring to react the tannic acid with the chain hydrocarbon having an epoxy group thereby forming a tannic acid derivative in which a hydrogen atom in at least some hydroxyl group of the tannic acid is substituted by a chain hydrocarbon group having a constitutional unit which results from ring-opening polymerization of a compound having a furan ring; and
a step of providing the second pack containing a hydrocarbon having two or more cyanate groups or a derivative of the hydrocarbon.

13. The process of producing an adhesive composition according to claim 12 , wherein the chain hydrocarbon having an epoxy group is a compound having an epoxy group comprising a three-membered ring.

14. The process of producing an adhesive composition according to claim 13 , wherein the compound having an epoxy group comprising a three-membered ring is one or more selected from the group consisting of propylene oxide, 1,2-epoxyhexane, 1,2-epoxyoctane, 1,2-epoxydecane, epibromohydrin, epichlorohydrin, epifluorohydrin, and epiiodohydrin.

15. The process of producing an adhesive composition according to claim 12 , wherein the compound having a furan ring is tetrahydrofuran or 2-methyltetrahydrofuran.

16. The process of producing an adhesive composition according to claim 12 , wherein a molar ratio between the tannic acid and the chain hydrocarbon group having at least one hydroxyl group is no less than 1:1 to no greater than 1:50.

17. The process of producing an adhesive composition according to claim 12 , wherein the hydrocarbon having at least two cyanate groups or the hydrocarbon derivative in the second pack is one or more selected from the group consisting of hexamethylene diisocyanate, tetramethylene diisocyanate, diphenylmethane diisocyanate, and isophorone diisocyanate.

18. A bonding method including:
a step of preparing a liquid mixture by mixing the first and second packs of the adhesive composition according to claim 1 together with a solvent,
a step of applying the liquid mixture to an adherend, and
a step of carrying out heat treatment,

wherein an amount of the second pack is no less than 5% by weight to no greater than 50% by weight relative to a total weight of the first and second packs.

19. The bonding method according to claim 18 , wherein the heat treatment is carried out at a temperature of no lower than 23° C. to no higher than 200° C.

20. The bonding method according to claim 18 , wherein the heat treatment is carried out for a time period of no less than 15 minutes to no longer than 60 minutes.

Assignees

• Nat Inst Materials Science

Inventors

• Naito Masanobu
• Das Sandip
• PAYRA Debabrata

Classifications

• C08K7/14

  Glass · CPC title

• C08K5/1515

  Three-membered rings · CPC title

• C09J7/35

  Heat-activated · CPC title

• C08G18/7657

  containing two or more aromatic rings · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title