US4601944A
Expired / Lapsed
US
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Polybutadiene-epoxy-anhydride laminating resins
Assignee: Isola Laminate Systems Corp
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Filing: 1985-06-05
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Granted: 1986-07-22
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Expires: 2005-06-05
Abstract
Abstract Disclosed is a composition that includes a liquid prepolymer that is the reaction product of a monoanhydride, a cycloaliphatic epoxy, and an alcohol. Also included in the composition is a maleated polybutadiene that is a reaction product of butadiene, maleic anhydride, and an oxygen scavenger. The composition also includes a tertiary amine accelerator, a free-radical initiator, and a solvent. A prepreg is prepared from the composition by immersing a porous substrate into the composition, drying and curing to the B-stage. A laminate is prepared by forming a stack of prepregs and heating under pressure to the C-stage.
Inventors
- 👤 Melvin P. Zussman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:08
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/28; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/244; H; H05; H05K; H05K1/00; H05K1/02; H05K1/03; H05K1/0313; H05K1/032; H05K1/0326; C08J2309/00; C08J2363/00; Y; Y10; Y10S; Y10S428/00; Y10S428/901; Y10T; Y10T442/00; Y10T442/20; Y10T442/2861; Y10T442/2893; Y10T442/2926; Y10T442/2951; Y10T442/30; Y10T442/3382; Y10T442/3415; Y10T442/3423
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
209 words
A composition comprising: (A) a liquid prepolymer that comprises the reaction product of (1) a monoanhydride; (2) a cycloaliphatic epoxy in an amount from about stoichiometric with said monoanhydride to about 20 mole % in excess of stoichiometric; and (3) about 0.1 to about 1% by weight, based on said monoanhydride weight plus said cycloaliphatic epoxy weight, of an alcohol; (B) maleated polybutadiene in a weight ratio with said liquid prepolymer of about 2 to 1 to about 1 to 2, said maleated polybutadiene comprising the reaction product of (1) polybutadiene having a molecular weight of about 1000 to about 5000, and having at least 80% 1,2-unsaturation; (2) about 0.05 to about 0.2 moles of maleic anhydride per repeating unit of said polybutadiene; and (3) about 0.01 to about 1.0% by weight, based on said maleated polybutadiene weight, of an oxygen scavenger; and (C) about 0.1 to about 3% by weight, based on total resin solids, of a tertiary amine accelerator; (D) about 1 to about 6% by weight, based on total resin solids, of a free radical initiator that has a half life of at least 30 minutes at 135° C.; and (E) about 30 to about 60% by weight of a solvent, based on total composition weight.
Claim 2
Dependent Claim
209 words
A composition comprising: (A) a liquid prepolymer that comprises the reaction product of (1) a monoanhydride; (2) a cycloaliphatic epoxy in an amount from about stoichiometric with said monoanhydride to about 20 mole % in excess of stoichiometric; and (3) about 0.1 to about 1% by weight, based on said monoanhydride weight plus said cycloaliphatic epoxy weight, of an alcohol; (B) maleated polybutadiene in a weight ratio with said liquid prepolymer of about 2 to 1 to about 1 to 2, said maleated polybutadiene comprising the reaction product of (1) polybutadiene having a molecular weight of about 1000 to about 5000, and having at least 80% 1,2-unsaturation; (2) about 0.05 to about 0.2 moles of maleic anhydride per repeating unit of said polybutadiene; and (3) about 0.01 to about 1.0% by weight, based on said maleated polybutadiene weight, of an oxygen scavenger; and (C) about 0.1 to about 3% by weight, based on total resin solids, of a tertiary amine accelerator; (D) about 1 to about 6% by weight, based on total resin solids, of a free radical initiator that has a half life of at least 30 minutes at 135° C.; and (E) about 30 to about 60% by weight of a solvent, based on total composition weight.
Claim 3
Dependent Claim
13 words
A composition according to claim 1 wherein said monoanhydride is saturated and aliphatic.
Claim 4
Dependent Claim
12 words
A composition according to claim 2 wherein said monoanhydride is hexahydrophthalic anhydride.
Claim 5
Dependent Claim
13 words
A composition according to claim 1 wherein said epoxy resin is a diepoxide.
Claim 6
Dependent Claim
14 words
A composition according to claim 4 wherein said epoxy resin is (3,4-epoxy-cyclohexylmethyl)-3,4-epoxy cyclohexane carboxylate.
Claim 7
Dependent Claim
12 words
A composition according to claim 1 wherein said alcohol is propylene glycol.
Claim 8
Dependent Claim
12 words
A composition according to claim 1 wherein said tertiary amine is benzyldimethylamine.
Claim 9
Dependent Claim
43 words
A composition according to claim 1 wherein said free radical initiator is a mixture of about 0.5 to about 3% by weight, based on total solids, of bis(t-butylperoxy)diisopropyl benzene, and about 0.5 to about 3% by weight, based on total solids, of 2,5-dimethyl2,5-di(t-butylperoxy)hexane.
Claim 10
Dependent Claim
23 words
A composition according to claim 1 wherein said solvent is selected from the group consisting of aromatic hydrocarbons, aliphatic ketones, and mixtures thereof.
Claim 11
Dependent Claim
23 words
A prepreg comprising a sheet of a porous material impregnated with a composition according to claim 1, dried and cured to the B-stage.
Claim 12
Dependent Claim
26 words
A prepreg according to claim 10 wherein said porous material is a woven fabric selected from the group consisting of quartz, poly(p-phenylene terephthalamide), and mixtures thereof.
Claim 13
Dependent Claim
17 words
A laminate comprising a stack of prepregs according to claim 10, heated under pressure to the C-stage.
Claim 14
Dependent Claim
20 words
A laminate according to claim 12 wherein a copper foil is bonded to at least one surface of said laminate.
Claim 15
Dependent Claim
29 words
A multilayer printed wiring board comprising a stack of prepregs according to claim 10, said stack including at least two sheets of copper foil, bonded into a solid mass.
Claim 16
Dependent Claim
216 words
A composition comprising: (A) a liquid prepolymer that comprises the reaction product of (1) an aliphatic, saturated monoanhydride; (2) a cycloaliphatic diepoxide in an amount from about 5 to about 12 mole % in excess of stoichiometric with said monoanhydride; (3) about 0.1 to about 1% by weight, based on monoanydride weight plus diepoxide weight, of a difunctional alcohol; (B) a maleated polybutadiene in a weight ratio with said liquid prepolymer of about 0.8 to 1 to about 1.2 to 1, said maleated polybutadiene comprising the reaction product of (1) polybutadiene having a molecular weight of about 3000 to about 4000, having at least 90% 1,2-unsaturation; (2) about 0.1 to about 0.15 moles of maleic anhydride per repeating unit of said polybutadiene; (3) about 0.3 to about 0.6% by weight, based on total solids, of an oxygen scavenger; and (C) about 0.25 to about 0.75% by weight, based on total solids, of a tertiary amine catalyst; (D) about 2 to about 4% by weight, based on total solids, of a peroxide free radical initiator that has a half life of at least 30 minutes at 135° C. and (E) about 35 to about 50% by weight, based on total solids, of a solvent selected from the group consisting of aromatic hydrocarbons, aliphatic ketones, and mixtures thereof.
Claim 17
Dependent Claim
216 words
A composition comprising: (A) a liquid prepolymer that comprises the reaction product of (1) an aliphatic, saturated monoanhydride; (2) a cycloaliphatic diepoxide in an amount from about 5 to about 12 mole % in excess of stoichiometric with said monoanhydride; (3) about 0.1 to about 1% by weight, based on monoanydride weight plus diepoxide weight, of a difunctional alcohol; (B) a maleated polybutadiene in a weight ratio with said liquid prepolymer of about 0.8 to 1 to about 1.2 to 1, said maleated polybutadiene comprising the reaction product of (1) polybutadiene having a molecular weight of about 3000 to about 4000, having at least 90% 1,2-unsaturation; (2) about 0.1 to about 0.15 moles of maleic anhydride per repeating unit of said polybutadiene; (3) about 0.3 to about 0.6% by weight, based on total solids, of an oxygen scavenger; and (C) about 0.25 to about 0.75% by weight, based on total solids, of a tertiary amine catalyst; (D) about 2 to about 4% by weight, based on total solids, of a peroxide free radical initiator that has a half life of at least 30 minutes at 135° C. and (E) about 35 to about 50% by weight, based on total solids, of a solvent selected from the group consisting of aromatic hydrocarbons, aliphatic ketones, and mixtures thereof.
Claim 18
Dependent Claim
22 words
A prepreg comprising a sheet of porous material impregnated with a composition according to claim 15, dried and cured to the B-stage.
Claim 19
Dependent Claim
18 words
A laminate comprising a stack of prepregs according to claim 16, bonded together and cured to the C-stage.
Claim 20
Independent Claim
226 words
A method of making a resin composition comprising: (A) preparing a liquid prepolymer by heating at about 80° to about 120° C. for about 4 to about 8 hours, a mixture that comprises: (1) a monoanhydride; (2) a cycloaliphatic epoxy in an amount from about stoichiometric with said monoanydride to about 20 mole % in excess of stoichiometric; and (3) about 0.1 to about 1% by weight, based on said monoanhydride weight plus said cycloaliphatic epoxy weight, of an alcohol; (B) mixing, in a weight ratio of about 2 to 1 to about 1 to 2, said liquid prepolymer with maleated polybutadiene that comprises the reaction product of (a) polybutadiene having a molecular weight of about 1000 to about 5000, and having at least 80% 1,2-unsaturation; (b) about 0.05 to about 0.2 moles of maleic anhydride per repeating unit of said polybutadiene; and (c) about 0.01 to about 1.0% by weight, based on maleated polybutadiene weight, of an oxygen scavenger; and (c) about 0.1 to about 3% by weight, based on total solids, of a tertiary amine catalyst; (d) about 1 to about 6% by weight, based on total resin solids, of a free radical initiator that has a half life of at least 30 minutes at 135° C.; and (e) about 30 to about 60% by weight of a solvent, based on total composition weight.
Claim 21
Independent Claim
226 words
A method of making a resin composition comprising: (A) preparing a liquid prepolymer by heating at about 80° to about 120° C. for about 4 to about 8 hours, a mixture that comprises: (1) a monoanhydride; (2) a cycloaliphatic epoxy in an amount from about stoichiometric with said monoanydride to about 20 mole % in excess of stoichiometric; and (3) about 0.1 to about 1% by weight, based on said monoanhydride weight plus said cycloaliphatic epoxy weight, of an alcohol; (B) mixing, in a weight ratio of about 2 to 1 to about 1 to 2, said liquid prepolymer with maleated polybutadiene that comprises the reaction product of (a) polybutadiene having a molecular weight of about 1000 to about 5000, and having at least 80% 1,2-unsaturation; (b) about 0.05 to about 0.2 moles of maleic anhydride per repeating unit of said polybutadiene; and (c) about 0.01 to about 1.0% by weight, based on maleated polybutadiene weight, of an oxygen scavenger; and (c) about 0.1 to about 3% by weight, based on total solids, of a tertiary amine catalyst; (d) about 1 to about 6% by weight, based on total resin solids, of a free radical initiator that has a half life of at least 30 minutes at 135° C.; and (e) about 30 to about 60% by weight of a solvent, based on total composition weight.
Claim 22
Dependent Claim
28 words
A method according to claim 18 wherein said maleated polybutadiene is prepared by heating at about 160° to about 190° C. for about 3 to about 6 hours.
Claim 23
Dependent Claim
58 words
A method according to claim 18 including the additional last steps of (1) impregnating a porous sheet with said composition; (2) evaporating the solvent from said impregnated sheet; and (3) heating said sheet at about 125° to about 160° C. for about 3 to about 10 minutes to cure said composition to the B-stage and form a prepreg.
Claim 24
Dependent Claim
57 words
A method according to claim 20 including the additional last steps of (1) forming a stack which comprises at least two of said prepregs; (2) heating said stack at about 180° to about 220° C. for about 40 minutes to about 2 hours under a pressure of about 500 to about 1500 psi. to form a laminate.
Claim 25
Dependent Claim
10 words
A prepreg made according to the method of claim 20.
Claim 26
Dependent Claim
10 words
A laminate made according to the method of claim 21.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-07-21 | 1990-01-20 | 1990-07-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-07-21 | 1994-01-20 | 1994-07-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-07-21 | 1998-01-20 | 1998-07-22 | $7700.00 | Window Closed / Lapsed |