Granted Patent B2

US 12,297,325 · App. 17/485,138 · Granted May 13, 2025

Inventor: Yoshiaki Honda (Osaka, JP)

Assignee: DAIKIN INDUSTRIES, LTD.

C08G77/46C08L71/02

Abstract

Claims (51)

1. An article comprising an electronic member and a cured product,

wherein

the cured product is formed by curing a curable composition;

the cured product is filled into a void of the electronic member;

the curable composition comprising:

(A) a compound which is a compound having two or more alkenyl groups and a perfluoro (poly) ether group in one molecule;

(B) an organosilicon compound which has two or more hydrogen atoms each bonding to a silicon atom, in one molecule; and

(C) a catalyst,

wherein

(A) the compound having two or more alkenyl groups and a perfluoro (poly) ether group in one molecule is a compound represented by formula (I):

CH 2 ═CH—R k1 -PFPE 1 -R k1 —CH—CH 2   (I)

wherein each R k1 , at each occurrence, independently represents a single bond, a C 1-20 alkylene group, —R 31 —X c —R 32 —, or —X d —R 32 —,

R 31 represents a single bond, —(CH 2 ) s ′—, or an o-, m-or p-phenylene group,

s′ is an integer of 1 to 20,

R 32 represents a single bond, —(CH 2 ) t ′—, or an o-, m-or p-phenylene group,

t′ is an integer of 1 to 20,

X c represents —O—, —S—, —C(O)O—, —CONR 34 —, —O—CONR 34 —, —Si(R 33 ) 2 —, —(Si(R 33 ) 2 O)m′—Si(R 33 ) 2 —, —O—(CH 2 ) u ′—(Si(R 33 ) 2 O) m ′—Si(R 33 ) 2 —, —O—(CH 2 ) u ′-Si(R 33 ) 2 —O—Si(R 33 ) 2 —CH 2 CH 2 —Si(R 33 ) 2 , —O—Si(R 33 ) 2 —, —O—(CH 2 ) u ′-Si(OCH 3 ) 2 OSi(OCH 3 ) 2 —, —CONR 34 —(CH 2 ) u ′—(Si(R 33 ) 2 O) m ′—Si(R 33 ) 2 —, —CONR 34 —(CH 2 ) u ′-N(R 34 )—, or —CONR 34 -(o-, m-or p-phenylene)-Si(R 33 ) 2 —,

R 33 , at each occurrence, independently represents a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group,

R 34 , at each occurrence, independently represents a hydrogen atom, or a C 1-6 alkyl group,

X d represents —S—, —C(O)O—, —CONR 34 —, —CONR 34 —, (CH 2 ) u ′—(Si(R 33 ) 2 O) m ′—Si(R 33 ) 2 —, —CONR 34 —(CH 2 ) u ′-N(R 34 )—, or —CONR 34 -(o-, m-or p-phenylene)-Si(R 33 ) 2 —,

m′ at each occurrence, is independently an integer of 1 to 100,

u′ is an integer of 1 to 20,

each PFPE 1 , at each occurrence, independently represents

(OC 6 F 12 ) a —(OC 5 F 10 ) b —(OC 4 F 8 ) c —(OC 3 X 10 6 ) d —(OC 2 F 4 ) e —(OCF 2 ) f —,

a, b, c and d are each independently an integer of 0 or more and 30 or less, e and f are each independently an integer of 5 or more and 200 or less, the sum of a, b, c, d, e and f is at least 10 or more, the occurrence order of the respective repeating units in parentheses with the subscript a, b, c, d, e or f is not limited in the formula, a ratio of e to f is less than 1.0, and each X 10 , at each occurrence, is independently a hydrogen atom, a fluorine atom or a chlorine atom,

the organosilicon compound is at least one represented by the following formula:

wherein

Rf, at each occurrence, independently represents a chlorine atom, a fluorine atom, or an alkyl group having 1 to 16 carbon atoms, the alkyl group being optionally substituted with one or more fluorine atoms or chlorine atoms,

R k3 , at each occurrence, is independently an alkyl group having 1 to 10 carbon atoms or an alkoxy group represented by OR k7 ,

R k4 , at each occurrence, is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxy group represented by OR k7 ,

R k5 , at each occurrence, is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxy group represented by OR k7 ,

R k6 , at each occurrence, is independently a hydrogen atom, a fluorine atom, or an alkylene group where one or more hydrogen atoms are each substituted with a fluorine atom,

R k7 , at each occurrence, is independently an alkyl group having 1 to 10 carbon atoms,

R k8 , is represented by —(O—(CH 2 ) a5 ) a6 —,

PFPE 2 is represented by formula:

—(OC 6 F 12 ) a ″—(OC 5 F 10 ) b ″—(OC 4 F 8 ) c ″—(OC 3 F 6 ) d ″—(OC 2 F 4 ) e ″—(OCF 2 ) f ″—,

wherein a″, b″, c″ and d″ are each independently an integer of 0 or more and 30 or less,

e″ and f″ are each independently an integer of 1 or more and 200 or less,

α1, at each occurrence, is independently an integer of 1 to 10,

α2, at each occurrence, is independently an integer of 1 to 50,

α3, at each occurrence, is independently an integer of 1 to 50,

α4, at each occurrence, is independently an integer of 1 to 50,

α5 is an integer of 1 to 6, and

α6 is 0 or 1.

2. The article according to claim 1 , wherein a hydrogen atom bonding to a silicon atom in (B) the organosilicon compound which has two or more hydrogen atoms each bonding to a silicon atom, in one molecule, is comprised in the range from 0.5 to 5.0 mol based on 1 mol of an alkenyl group in (A) the compound having two or more alkenyl groups and a perfluoro (poly) ether group in one molecule.

3. The article according to claim 1 , wherein the catalyst is a transition metal catalyst.

4. The article according to claim 1 , wherein the catalyst comprises at least one comprising platinum, rhodium, ruthenium, iridium and palladium.

5. The article according to claim 1 , wherein the catalyst comprises platinum.

6. The article according to claim 1 , comprising 0.1 to 500 ppm by mass of the catalyst in terms of metal atom relative to (A) the compound having two or more alkenyl groups and a perfluoro (poly) ether group in one molecule.

7. The article according to claim 1 , wherein a ratio of the sum of e and f to the sum of a, b, c, d, e and f is 0.80 or more in (A) the compound having two or more alkenyl groups and a perfluoro (poly) ether group in one molecule.

8. The article according to claim 1 , wherein X 10 is a fluorine atom.

Assignments (1)

Priority Claims (1)

Continuity (2)

References Cited (16)