IP Library Granted Patent US 9,238,757
Granted Patent B2
US 9,238,757 · App. 13/823,759 · Granted Jan 19, 2016

Bonding method, bondability improving agent, surface modification method, surface modifying agent, and novel compound

Inventors: Kunio Mori (Morioka, JP); Yusuke Matsuno (Morioka, JP); Katsuhito Mori (Morioka, JP); Takahiro Kudo (Morioka, JP)
Assignees: Kunio Mori; Sulfur Chemical Laboratory Incorporated
C09J5/00C07F5/068C07F7/1836C09J2205/31C09J2483/00Y10T428/31536
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Quick Facts
Patent No.
US 9,238,757
App. No.
13/823,759
Granted
Jan 19, 2016
Kind
B2
Abstract

To provide a technique by which an —OH group can be effectively formed on a material surface for the purpose of making the material suitable for bonding (for example, for molecular bonding) that utilizes a chemical reaction (chemical binding). [Solution] A bonding method for bonding a substrate A and a substrate B, which comprises: a step for applying an agent that contains the compound (α) described below on the surface of the substrate A; a step for arranging the substrate B so as to face the compound (α) that is present on the surface of the substrate A; and a step for integrally bonding the substrate A and the substrate B by applying a force onto the substrate A and/or the substrate B. The compound (α) is a compound that has an OH group or an OH-forming group, an azide group and a triazine ring in each molecule, and the substrate A is configured using a polymer.

Claims (97)

1. A method of bonding a base A and a base B, the method comprising:

(i) applying an agent comprising a compound α onto a surface of the base A;

(ii) arranging the base B so that the base B faces the compound α on the base A; and

(iii) applying force onto the base A, the base B, or both the base A and the base B to integrally bond the base A and the base B;

wherein the compound α is a compound comprising an OH group or an OH yielding group, an azide group, and a triazine ring per molecule; and

the base A is configured by employing a polymer.

2. The method according to claim 1 , wherein in said applying (iii), the force is applied such that the OH group of the compound α on the base A or OH groups generated from the OH yielding group of the compound α on the base A contact a surface of the base B.

3. The method according to claim 1 , wherein said applying (iii) occurs at a temperature of from 0 to 300° C.

4. The method according to claim 1 , further comprising:

(iv) irradiating the compound on the surface of the base A with a light having a predetermined pattern.

5. The method according to claim 4 , wherein in said irradiating (iv), the base A and the azide group of the compound α react to each other, and the compound α is bonded to the surface of the base A.

6. The method according to claim 4 , wherein the light is an ultraviolet ray.

7. The method according to claim 1 , wherein the OH group or the OH yielding group is an alkoxysilyl group.

8. The method according to claim 1 , wherein the compound α is a compound of a general formula [I],

wherein:

E is an arbitrary group;

F is the OH group or the OH yielding group; and

-Q is —N 3 or —NR 1 (R 2 ), wherein

each R 1 and R 2 is independently H, a hydrocarbon group comprising from 1 to 24 carbons, or a —RSi(R′) n (OA) 3-n , wherein

R is a chain hydrocarbon group comprising from 1 to 12 carbons, R′ is a chain hydrocarbon group comprising from 1 to 4 carbons, A is H or a chain hydrocarbon group comprising from 1 to 4 carbons, and n is an integer of from 0 to 2.

9. The method according to claim 1 , wherein the compound α is a compound of a general formula [Io],

wherein:

-Q is —N 3 or —NR 1 (R 2 );

each R 1 and R 2 is independently H, a hydrocarbon group comprising from 1 to 24 carbons, or a —RSi(R′) n (OA) 3-n , wherein

R is a chain hydrocarbon group comprising from 1 to 12 carbons, R′ is a chain hydrocarbon group comprising from 1 to 4 carbons, A is H or a chain hydrocarbon group comprising from 1 to 4 carbons, and n is an integer of from 0 to 2; and

at least one of R 1 and R 2 is —RSi(R′) n (OA) 3-n .

10. The method according to claim 1 , wherein the compound α is a compound of a general formula [Ia],

wherein:

each R 1 and R 2 is independently H, a hydrocarbon group comprising from 1 to 24 carbons, or a —RSi(R′) n , (OA) 3-n ; wherein

R is a chain hydrocarbon group comprising from 1 to 12 carbons, R′ is a chain hydrocarbon group comprising from 1 to 4 carbons, A is H or a chain hydrocarbon group comprising from 1 to 4 carbons, and n is an integer of from 0 to 2; and

at least one of R 1 and R 2 is —RSi(R′) n (OA) 3-n .

11. The bending method according to claim 1 , wherein the compound α is a compound of a general formula [Ib],

wherein:

each R 1 and R 2 is independently H, a hydrocarbon group number of comprising from 1 to 24 carbons, or a —RSi(R′) n (OA) 3-n ; wherein

R is a chain hydrocarbon group comprising from 1 to 12 carbons, R′ is a chain hydrocarbon group comprising from 1 to 4 carbons, A is H or a chain hydrocarbon group comprising from 1 to 4 carbons, and n is an integer of from 0 to 2; and

at least one of all R 1 s and all R 2 s is —RSi(R′) n (OA) 3-n .

12. The method according to claim 1 , further comprising:

(v) applying a substance of a general formula [II] onto a surface of the compound α after said applying (i) and before said arranging (ii),

wherein:

each of X′ and Y′ is independently Si or Ti;

Z is Al;

G is a hydrocarbon group comprising from 1 to 3 carbons or an alkoxy group comprising from 1 to 3 carbons;

B is an alkoxy group comprising from 1 to 3 carbons;

n and m each is an integer of from 0 to 200, (wherein 2≦n+m≦400; and

p is an integer of from 0 to 100.

13. The method according to claim 12 , further comprising:

(vi) applying a compound β comprising an alkoxysilyl group, an alkoxy alminate group, or an alkoxy titanate group onto the surface of the compound α after said applying (v) and before said arranging (ii).

14. The method according to claim 13 , wherein the compound β is a compound of a general formula [T],

L-Si(M′)n(OM)3- n   General formula [T]

wherein:

L is an organic group, which optionally is aliphatic, aromatic, a chain, or cyclic and optionally comprises elements other than carbon and hydrogen;

each M′ is independently a chain hydrocarbon group comprising from 1 to 4 carbons;

each M is H or a chain hydrocarbon group comprising from 1 to 4 carbons; and

n is an integer of from 0 to 2.

15. The method according to claim 13 , wherein the compound β is a compound of a general formula [III],

wherein:

R 5 is a hydrocarbon group comprising 1 to 12 carbon;

R 6 is H or a hydrocarbon group comprising 1 to 10 carbon;

each X″ is independently H or a hydrocarbon group comprising 1 to 10 carbon;

each Y″ is independently an alkyloxy group comprising 1 to 10 carbon;

n is an integer of from 1 to 3; and

M′ is H, Li, Na, K, or Cs.

16. The bonding method according to claim 13 , wherein the compound β is a compound of a general formula [IV],

wherein:

R 5 is a hydrocarbon group comprising from 1 to 12 carbons;

R 7 is a hydrocarbon group comprising from 1 to 12 carbons;

each X″ is independently H or a hydrocarbon group comprising from 1 to 10 carbons;

each Y″ is independently an alkyloxy group comprising from 1 to 10 carbons;

n and m each is an integer of from 1 to 3; and

M′ is H, Li, Na, K or Cs.

17. The method according to claim 1 , further comprising:

(vi) applying a compound β comprising an alkoxysilyl group, an alkoxy alminate group, or an alkoxy titanate group onto a surface of the compound α after said applying (i) and before said arranging (ii).

18. The method according to claim 17 , wherein the compound β is a compound of a general formula [T],

L-Si(M′) n (OM) 3-n   General formula [T]

wherein:

L is an organic group, which optionally is aliphatic, aromatic, a chain, or cyclic and optionally comprises elements other than carbon and hydrogen;

each M′ is independently a chain hydrocarbon group comprising from 1 to 4 carbons;

each M is independently H or a chain hydrocarbon group comprising from 1 to 4 carbons; and

n is an integer of from 0 to 2.

19. The method according to claim 17 , wherein the compound β is a compound of a general formula [III],

wherein:

R 5 is a hydrocarbon group comprising from 1 to 12 carbons;

R 6 is H or a hydrocarbon group comprising from 1 to 10 carbons;

each X″ is independently H or a hydrocarbon group comprising from 1 to 10 carbons;

each Y″ is independently an alkyloxy group comprising from 1 to 10 carbons;

n is an integer of from 1 to 3; and

M 1 is H, Li, Na, K or Cs.

20. The method according to claim 17 , wherein the compound β is a compound of a general formula [IV],

wherein:

R 5 is a hydrocarbon group comprising from 1 to 12 carbons;

R 7 is a hydrocarbon group comprising from 1 to 12 carbons;

each X″ is independently H or a hydrocarbon group comprising from 1 to 10 carbons;

each Y″ is independently an alkyloxy group comprising from 1 to 10 carbons;

n and m each is an integer of from 1 to 3; and

M 1 is H, Li, Na, K or Cs.

21. The method according to claim 1 , wherein the compound α is at least one selected from the group consisting of 6-azide-2,4-bis(ethanolamino)-1,3,5-triazine, 6-azide-2,4-bis(hexanolamino)-1,3,5-triazine, 6-azide-2,4-bis(decanolamino)-1,3,5-triazine, 6-azide-2,4-bis(3,4-bishydroxyphenyl)amino)-1,3,5-triazine, 6-azide-2,4-bis(2,2-dihydroxymethyl)ethylamino-1,3,5-triazine, 6-azide-2,4-bis(tris methanol methyl)methylamino-1,3,5-triazine, 6-azide-2,4-(1,2-dihydroxypropyl)amino-1,3,5-triazine, 6-azide-2,4-bis(3-triethoxysilyl)propylamino-1,3,5-triazine (TE-MAZ), 6-azide-2,4-bis(3-methylethylketoxyminosilyl)propylamino-1,3,5-triazine, 6-azide-2,4-bis(3-methylethylketoxyminosilyl)propylamino-1,3,5-triazine, 6-azide-2,4-bis(3-triisopropoxysilyl)propylamino-1,3,5-triazine, 6-azide-2,4-bis(3-triacetoxysilyl)propylamino-1,3,5-triazine, 6-azide-2,4-bis(3-triisopropoxysilyl)propylamino-1,3,5-triazine, 6-azide-2,4-bis(3-triisopropoxysilyl)propylamino-1,3,5-triazine, 6-azide-2,4-bis(3-tribenzoxysilyl)propylamino-1,3,5-triazine, 6-azide-2,4-bis(diethanolamino)-1,3,5-triazine, 6-azide-2,4-bis(dihexanolamino)-1,3,5-triazine, 6-azide-2,4-bis(didecanolamino)-1,3,5-triazine, 6-azide-2,4-bis(3-triethoxysilylpropyl)amino-1,3,5-triazine, 6-azide-2,4-bis(6-triethoxysilylhexyl)amino-1,3,5-triazine, 6-azide-2,4-bis(10-triethoxysilyldodecyl)amino-1,3,5-triazine, 2,4-diazide-6-(N,N-diethanol)amino-1,3,5-triazine (DEA-DAZ), 2,4-diazide-6-(N,N-didecanol)amino-1,3,5-triazine, 2,4-diazide-6-(3,4-bishydroxyphenyl)amino-1, 3,5-triazine, 2,4-diazide-6-(2,2-dihydroxymethyl)ethylamino-1,3,5-triazine, 2,4-diazide-6-(tris methanol methyl)methylamino-1,3,5-triazine, 2,4-diazide-6-(1,2-dihydroxypropyl)amino-1,3,5-triazine, 2,4-diazide-6-(3-triethoxysilylpropyl)amino-1,3,5-triazine (TE-DAZ), 2,4-diazide-6-bis(3-methylethylketoxyminosilyl)propylamino-1,3,5-triazine, 2,4-diazide-6-bis(3-methylethylketoxyminosilyl)propylamino-1,3,5-triazine, triisopropoxysilyl)propylamino-1,3,5-triazine, 2,4-diazide-6-(3-triacetoxysilyl)propylamino-1,3,5-triazine, 2,4-diazide-6-(3-triisopropoxysilyl)propylamino-1,3,5-triazine, 2,4-diazide-6-(3-triisopropoxysilyl)propylamino-1,3,5-triazine, 2,4-diazide-6-(3-tribenzoxysilyl)propylamino-1,3,5-triazine, 2,4-diazide-6-bis(dihydroxyethyl)amino-1,3,5-triazine, 2,4-diazide-6-(N,N-dihexanol)amino-1,3,5-triazine, 2,4-diazide-6-(N,N-didecanol)amino-1,3,5-triazine, 2,4-diazide-6-(N,N-bis(3-triethoxysilylpropyl)amino-1,3,5-triazine (BTE-DAZ), 2,4-diazide-6-(N,N-bis(6-triethoxysilylhexyl)amino-1,3,5-triazine, 6-(11-triethoxysilylundecyl)amino-1,3,5-triazine-2,4-diazide (TEU-DAZ), 6-(3-diethoxymethylsilylpropyl)amino-1,3,5-triazine-2,4-diazide (DEM-DAZ), and 6-(4-triethoxysilylbutyl)amino-1,3,5-triazine-2,4-diazide (TEB-DAZ).

22. A bonded body produced by the method according to claim 1 .

Assignments (2)
CHANGE OF NAME Recorded Jul 9, 2014
From: SULFUR CHEMICAL INSTITUTE INCORPORATED
To: SULFUR CHEMICAL LABORATORY INCORPORATED
Reel/Frame 033282/0060 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2013
From: MORI, KUNIO; MATSUNO, YUSUKE; MORI, KATSUHITO; KUDO, TAKAHIRO
To: MORI, KUNIO; SULFUR CHEMICAL INSTITUTE INCORPORATED
Reel/Frame 030030/0614 →
Priority Claims (1)
JP 2010-220512 · Sep 30, 2010 · national
Continuity (1)
Related Publication 20130177770A1 · Jul 11, 2013