# US 9,518,194 B2 · Toughened arylcyclobutene polymers

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- Number: US 9,518,194 B2
- Document ID: US9518194B2
- Status: Granted
- Kind: B2
- Application number: 15/055,987
- Filed: 2016-02-29
- Published: 2016-10-13
- Granted: 2016-12-13
- Earliest claimed: 2015-04-10
- Assignees: Dow Global Technologies LLC; Rohm and Haas Electronic Materials LLC
- Applicants: Dow Global Technologies LLC; Rohm and Haas Electronic Materials LLC
- Inventors: Zhifeng Bai; Michael K. Gallagher; Zidong Wang; Christopher J. Tucker; Matthew T. Bishop; Elissei Iagodkine; Mark S. Oliver
- Web page: https://patentgrep.com/patent/US9518194B2

## CPC

- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- B05D 3/007: {After-treatment}
- B05D 3/10: by other chemical means
- C08G 61/02: Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08L 27/06: Homopolymers or copolymers of vinyl chloride
- C08L 51/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 71/02: Polyalkylene oxides
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 143/04: Homopolymers or copolymers of monomers containing silicon
- C09J 165/00: Adhesives based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09J107/00 - C09J157/00, C09J161/00 take precedence); Adhesives based on derivatives of such polymers
- H05K 3/285: {Permanent coating compositions}
- H10P 72/74: {using temporarily an auxiliary support}
- C08G 2261/3424: non-conjugated, e.g. paracyclophanes or xylenes
- C08G 2261/344: containing heteroatoms
- C08G 2261/65: Electrical insulator
- C08L 25/10: with conjugated dienes
- C08L 25/16: Homopolymers or copolymers of alkyl-substituted styrenes
- C08L 51/04: grafted on to rubbers
- C08L 51/06: grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
- H10P 72/7412: {the auxiliary support including means facilitating the separation of a device or wafer from the auxiliary support}
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

Arylcyclobutene polymers having improved toughness are provided. Compositions and methods for coating arylcyclobutene polymers having improved toughness are also provided.

## Claims

### Claim 1

A composition comprising: a) a curable material chosen from one or more arylcyclobutene monomers, one or more polymers comprising one or more arylcyclobutene monomers as polymerized units, and mixtures thereof; and b) one or more toughening agents having the formula: R1—(O-A)x(OCH2CH2)y—OR2; wherein A is CH2CHR or CHRCH2; R is a C2-8 hydrocarbyl moiety; R1 and R2 are independently chosen from H, C1-20 alkyl, C6-20 aryl, C7-40 substituted aryl, C2-20 alkenyl, C2-20 alkynyl, maleimide, maleamide/ester, maleamide/carboxylic acid, and (meth)acryloyl; x is an integer from 2 to 500; and y is an integer from 0 to 500.

### Claim 2 (depends on 1)

The composition of claim 1 wherein at least one of R1 and R2 is H.

### Claim 3 (depends on 1)

The composition of claim 1 wherein R1 and R2 are independently chosen from H, C1-20 alkyl, C6-20 aryl, and C7-40 substituted aryl.

### Claim 4 (depends on 1)

The composition of claim 1 wherein R1 and R2 are independently chosen from C2-20 alkenyl, C2-20 alkynyl, maleimide, maleamide/ester, maleamide/carboxylic acid, and (meth)acryloyl.

### Claim 5 (depends on 1)

The composition of claim 1 wherein x is an integer from 5 to 250 and y is an integer from 0 to 250.

### Claim 6 (depends on 1)

The composition of claim 1 wherein y is an integer from 5 to 50.

### Claim 7 (depends on 1)

The composition of claim 1 wherein R is a C2-6 hydrocarbyl moiety.

### Claim 8 (depends on 7)

The composition of claim 7 wherein R is a C2-4 hydrocarbyl moiety.

### Claim 9 (depends on 1)

The composition of claim 1 wherein the one or more arylcyclobutene monomers have the formula:
wherein B is an n-valent linking group; Ar is a polyvalent aryl group and the carbon atoms of the cyclobutene ring are bonded to adjacent carbon atoms on the same aromatic ring of Ar; n is an integer of 1 or more; and R5 is a monovalent group.

### Claim 10 (depends on 9)

The composition of claim 9 wherein B has the formula) —[C(R10)═CR11]xZ, wherein R10 and R11 are independently chosen from hydrogen, C1-6 alkyl, and aryl; Z is chosen from hydrogen, C1-6 alkyl, aryl, siloxanyl, —CO2R12; each R12 is independently chosen from H, C1-6 alkyl, aryl, aralkyl, and alkaryl; and x=1 or 2.

### Claim 11 (depends on 9)

The composition of claim 9 wherein one or more arylcyclobutene monomers has the formula:
wherein each R6 is independently chosen from H, C1-6 alkyl, and C1-6 alkoxy; each R7 is independently chosen from C1-6 alkyl, tri-C1-6-alkylsilyl, C1-6 alkoxy, and halo; each R8 is independently a divalent, ethylenically unsaturated organic group; each R9 is independently chosen from H, C1-6 alkyl, aralkyl and phenyl; p is an integer of 1 or more; and q is an integer from 0-3.

### Claim 12 (depends on 1)

The composition of claim 1 wherein the one or more toughening agents are present in an amount of 0.1 to 35 wt %, based on the total weight of the one or more curable polymers.

### Claim 13 (depends on 1)

The composition of claim 1 wherein the composition is substantially free of polybutyleneoxide monododecylphenyl ether.

### Claim 14 (depends on 1)

The composition of claim 1 further comprising one or more organic solvents.

### Claim 15 (depends on 14)

A method comprising: coating on a substrate a layer of the composition of claim 14; at least partially removing the one or more organic solvents; and curing the one or more curable polymers to form a cured polymer coating.