PREPOLYMER, METHOD OF PREPARING THE SAME, RESIN COMPOSITION AND ARTICLE MADE THEREFROM

• US 20200131286A1
• Filed: 12/20/2018
• Published: 04/30/2020
• Est. Priority Date: 10/31/2018
• Status: Active Grant

• Current Assignee: Elite Electronic Material (Zhongshan) Co., Ltd.
• Original Assignee: Elite Electronic Material (Zhongshan) Co., Ltd.
• Inventors: WANG, Rongtao, ZHANG, Yan, LI, Bingbing
• Granted Patent: US 10,954,322 B2
• Time in Patent Office: Days
• CPC Class Codes: C08F 12/34 Monomers containing two or more unsaturated aliphatic radicals
• CPC Class Codes: C08F 16/32 Monomers containing two or more unsaturated aliphatic radicals
• CPC Class Codes: C08F 212/12 Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
• CPC Class Codes: C08F 212/34 Monomers containing two or more unsaturated aliphatic radicals
• CPC Class Codes: C08F 212/36 Divinylbenzene
• CPC Class Codes: C08F 226/06 by a heterocyclic ring containing nitrogen
• CPC Class Codes: C08F 2500/01 High molecular weight, e.g. >800,000 Da.
• CPC Class Codes: C08K 3/36 Silica
• CPC Class Codes: C08K 5/01 Hydrocarbons C08K5/0091 takes precedence
• CPC Class Codes: C08K 5/06 Ethers; Acetals; Ketals; Ortho-esters
• CPC Class Codes: C08K 5/08 Quinones
• CPC Class Codes: C08K 5/13 Phenols; Phenolates
• CPC Class Codes: C08K 5/14 Peroxides
• CPC Class Codes: C08K 5/18 with aromatically bound amino groups
• CPC Class Codes: C08K 5/34924 containing cyanurate groups; Tautomers thereof
• CPC Class Codes: C08K 5/37 Thiols
• CPC Class Codes: C08K 5/38 Thiocarbonic acids; Derivatives thereof, e.g. xanthates ; i.e. compounds containing -X-C(=X)- groups, X being oxygen or sulfur, at least one X being sulfur
• CPC Class Codes: C08K 5/46 with oxygen or nitrogen in the ring
• CPC Class Codes: C08K 5/49 Phosphorus-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08L 2203/16 used for films
• CPC Class Codes: C08L 2203/20 : use in electrical or conductive gadgets
• CPC Class Codes: C08L 25/10 : with conjugated dienes
• CPC Class Codes: C08L 33/08 : Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 35/02 : Homopolymers or copolymers of esters C08L35/06, C08L35/08 take precedence
• CPC Class Codes: C08L 55/005 : Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
• CPC Class Codes: C08L 63/00 : Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 67/00 : Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 71/12 : Polyphenylene oxides
• CPC Class Codes: C08L 71/126 : modified by chemical after-treatment
• CPC Class Codes: C08L 79/08 : Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Abstract

A prepolymer, which is prepared by subjecting an unsaturated bond-containing compound and a bis(vinylphenyl) compound monomer or a polymer thereof to a prepolymerization reaction, is provided. The bis(vinylphenyl) compound contains between 80% and 99% of para-para vinyl groups and has a monomer content of between 80% and 100%. Moreover, a resin composition comprising the prepolymer and an additive, a method of preparing the prepolymer, and an article made from the resin composition are also provided.

Claims

1. A prepolymer prepared by subjecting an unsaturated bond-containing compound and a bis(vinylphenyl) compound monomer of Formula (I) or a polymer thereof to a prepolymerization reaction,

2. The prepolymer of claim 1, wherein the unsaturated bond-containing compound comprises acrylate, styrene, t-butyl styrene, divinylbenzene, triallyl isocyanurate, triallyl cyanurate, 1,2,4-trivinyl cyclohexane, polyphenylene oxide, cyanate ester, maleimide resin or a combination thereof.

3. The prepolymer of claim 1, wherein the prepolymerization reaction is performed in the presence of a peroxide.

4. The prepolymer of claim 3, wherein the peroxide comprises benzoyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, 2,5-dimethyl-2,5-di(t-butylperoxy)-3-hexyne, di-t-butyl peroxide, di(t-butylperoxyisopropyl)benzene, di(t-butylperoxy)phthalate, di(t-butylperoxy)isophthalate, t-butyl peroxybenzoate, 2,2-di(t-butylperoxy)butane, 2,2-di(t-butylperoxy)octane, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, lauroyl peroxide, t-hexyl peroxypivalate, dibutylperoxyisopropylbenzene, bis(4-t-butylcyclohexyl) peroxydicarbonate or a combination thereof.

5. The prepolymer of claim 1, wherein the prepolymerization reaction is performed in the presence of a molecular weight regulator.

6. The prepolymer of claim 5, wherein the molecular weight regulator comprises n-butyl mercaptan, dodecyl mercaptan, mercaptoacetic acid, mercaptopropanoic acid, mercaptoethanol, 2,4-diphenyl-4-methyl-1-pentene or a combination thereof.

7. The prepolymer of claim 1, wherein the prepolymerization reaction is performed in the presence of a polymerization inhibitor.

8. The prepolymer of claim 7, wherein the polymerization inhibitor comprises hydroquinone, 4-methoxyphenol, p-benzoquinone, phenothiazine, β

-phenylnaphthylamine, 4-t-butylcatechol, methylene blue, 4,4′

-butylidenebis(6-t-butyl-3-methylphenol), 2,2′

-methylenebis (4-ethyl-6-t-butylphenol) or a combination thereof.

9. The prepolymer of claim 1, wherein the polymerization reaction has a conversion rate of between 10% and 90%.

10. The prepolymer of claim 1, which contains a reactive vinyl group.

11. The prepolymer of claim 1, which has a weight average molecular weight of between 1000 and 200000.

12. A resin composition comprising the prepolymer of claim 1 and an additive.

13. The resin composition of claim 12, comprising 1 to 300 parts by weight of the additive relative to 100 parts by weight of the prepolymer.

14. The resin composition of claim 12, wherein the additive comprises polyphenylene oxide, cyanate ester, maleimide resin, polyolefin, acrylate, styrene, t-butyl styrene, divinylbenzene, bis(vinylbenzyl) ether, bis(vinylphenyl) ethane, triallyl isocyanurate, triallyl cyanurate, 1,2,4-trivinyl cyclohexane or a combination thereof.

15. The resin composition of claim 12, further comprising epoxy resin, phenoxy resin, benzoxazine resin, styrene maleic anhydride, acrylic resin, polyester, amine curing agent, diallyl bisphenol A, polyamide, polyimide or a combination thereof.

16. The resin composition of claim 12, further comprising flame retardant, inorganic filler, curing accelerator, solvent, molecular weight regulator, polymerization inhibitor, toughening agent, coupling agent or a combination thereof.

17. The resin composition of claim 12, wherein a varnish made from the resin composition has a shelf life of greater than or equal to 1 day.

18. A method of preparing the prepolymer of claim 1, comprising subjecting an unsaturated bond-containing compound and a bis(vinylphenyl) compound monomer of Formula (I) or a polymer thereof to a prepolymerization reaction.

19. The method of claim 18, further comprising adding a peroxide, a molecular weight regulator, a polymerization inhibitor or a combination thereof.

20. An article made from the resin composition of claim 12, comprising a resin film, a prepreg, a laminate or a printed circuit board.

21. The article of claim 20, having a glass transition temperature as measured by using a dynamic mechanical analyzer by reference to IPC-TM-650 2.4.24.4 of greater than or equal to 216°

C.

22. The article of claim 20, having a Z-axis ratio of thermal expansion as measured by using a thermomechanical analyzer by reference to IPC-TM-650 2.4.24.5 of less than or equal to 2.70%.

23. The article of claim 20, having a copper foil peeling strength as measured by using a tensile strength tester by reference to IPC-TM-650 2.4.8 of greater than or equal to 3.0 lb/in.

24. The article of claim 20, characterized in that no delamination occurs after moisture absorption of 5 hours as measured by reference to IPC-TM-650 2.6.16.1 and then subject to a solder dip test by reference to IPC-TM-650 2.4.23.

25. The article of claim 20, having at least one of the following properties:

a dissipation factor as measured by reference to JIS C2565 of less than or equal to 0.0020; and

a dielectric constant as measured by reference to JIS C2565 of less than or equal to 3.10.