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US5045381A Expired / Lapsed US ⏱️ 0.0 years remaining

Thermosetting resin composition, printed circuit board using the resin composition and process for producing printed circuit board

Assignee: Hitachi Ltd
•
Filing: 1989-09-27
•
Granted: 1991-09-03
•
Expires: 2009-09-27
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Abstract

Abstract A thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR1## wherein X is a fluorine atom, a bromine atom and a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR2## m is an integer of 1 to 4 and n is an integer of 5 to 100, and further containing a compound having at least one N-substituted unsaturated imido group, if required, can produce a printed circuit board of high flame retardness, low dielectric constant, low moisture absorption and a high mechanical strength at an elevated temperature.

Inventors

  • 👤 Masao Suzuki
  • 👤 Junichi Katagiri
  • 👤 Akira Nagai
  • 👤 Masahiro Suzuki
  • 👤 Akio Takahashi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 22:16
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/09; C08G18/092; C08G18/28; C08G18/40; C08G18/62; C08G18/6275; C08G18/67; C08G18/6705; C08G18/675; C08G18/677; C08G18/678; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1035; C08L; C08L25/00; C08L25/18; H; H01; H01B; H01B3/00; H01B3/18; H01B3/30; H01B3/302; H01B3/303; H05; H05K; H05K1/00; H05K1/02; H05K1/03; H05K1/0313; H05K1/032; H05K1/0346; Y; Y10; Y10S; Y10S428/00; Y10S428/901; Y10T; Y10T156/00; Y10T156/10; Y10T428/00; Y10T428/24; Y10T428/24802; Y10T428/24917; Y10T428/31504; Y10T428/31547; Y10T428/31678

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 189 words
A printed circuit board, which comprises a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR26## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR27## m is an integer of 1 to 4 and n is an integer of 5 to 100; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 2
Dependent Claim 189 words
A printed circuit board, which comprises a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR26## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR27## m is an integer of 1 to 4 and n is an integer of 5 to 100; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 3
Dependent Claim 200 words
A printed circuit board, which comprises a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR28## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR29## m is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 4
Dependent Claim 200 words
A printed circuit board, which comprises a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR28## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR29## m is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 5
Dependent Claim 364 words
A multi-layered, printed circuit board, which comprises a lamination of a plurality of printed circuit boards each comprising a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I) A--R.sub.1 A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR30## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR31## m is an integer of 1 to 4 and n is an integer of 5 to 100, or printed circuit boards each comprising a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR32## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR33## is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 6
Dependent Claim 364 words
A multi-layered, printed circuit board, which comprises a lamination of a plurality of printed circuit boards each comprising a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I) A--R.sub.1 A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR30## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR31## m is an integer of 1 to 4 and n is an integer of 5 to 100, or printed circuit boards each comprising a conductor of a metallic foil and an insulating layer made of a fibrous substrate material impregnated and cured with a thermosetting resin composition, the thermosetting resin composition comprising a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR32## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR33## is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 7
Dependent Claim 315 words
A curable material which comprises a woven fabric or non-woven fabric of inorganic fibers or organic fibers, impregnated with a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR34## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR35## m is an integer of 1 to 4 and n is an integer of 5 to 100 or a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR36## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR37## m is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 8
Dependent Claim 315 words
A curable material which comprises a woven fabric or non-woven fabric of inorganic fibers or organic fibers, impregnated with a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR34## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR35## m is an integer of 1 to 4 and n is an integer of 5 to 100 or a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR36## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR37## m is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 9
Dependent Claim 160 words
A thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR38## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR39## m is an integer of 1 to 4 and n is an integer of 5 to 100; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 10
Dependent Claim 160 words
A thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR38## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR39## m is an integer of 1 to 4 and n is an integer of 5 to 100; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 11
Dependent Claim 170 words
A thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR40## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR41## is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated amido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 12
Dependent Claim 170 words
A thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR40## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR41## is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated amido group; a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight.
Claim 13
Dependent Claim 235 words
A process for producing a printed circuit board, which comprises: a step of heating a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR42## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR43## m is an integer of 1 to 4 and n is an integer of 5 to 100, thereby forming a prepolymer, a mixing ratio of the cyanate compound of isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight; a step of dissolving the prepolymer in a solvent, thereby forming an impregnation varnish, impregnating a fibrous substrate material with the impregnation varnish, followed by drying, thereby preparing a prepreg; and a step of laminating a plurality of the thus obtained prepregs, thereby obtaining a laminate, and pressing the laminate together with conductor metal foils with heating.
Claim 14
Dependent Claim 235 words
A process for producing a printed circuit board, which comprises: a step of heating a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR42## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR43## m is an integer of 1 to 4 and n is an integer of 5 to 100, thereby forming a prepolymer, a mixing ratio of the cyanate compound of isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight; a step of dissolving the prepolymer in a solvent, thereby forming an impregnation varnish, impregnating a fibrous substrate material with the impregnation varnish, followed by drying, thereby preparing a prepreg; and a step of laminating a plurality of the thus obtained prepregs, thereby obtaining a laminate, and pressing the laminate together with conductor metal foils with heating.
Claim 15
Dependent Claim 246 words
A process for producing a printed circuit board, which comprises: a step of heating a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR44## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR45## m is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group, thereby forming a prepolymer, a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight; a step of dissolving the prepolymer in a solvent, thereby forming an impregnation varnish, impregnating a fibrous substrate material with the impregnation varnish, followed by drying, thereby preparing a prepreg; and a step of laminating a plurality of the thus obtained prepregs, thereby obtaining a laminate, and pressing the laminate together with conductor metal foils with heating.
Claim 16
Dependent Claim 246 words
A process for producing a printed circuit board, which comprises: a step of heating a thermosetting resin composition which comprises a cyanate compound or an isocyanate compound represented by the following general formula (I): A--R.sub.1 --A (I) wherein R 1 is an aromatic group, an alicyclic group or a mixed group thereof and A is a cyanate group or an isocyanate group, and a poly-(p-hydroxystyrene) derivative represented by the following general formula (II): ##STR44## wherein X is a fluorine atom, a bromine atom or a chlorine atom, R 2 is an alkenyl group and an unsaturated carboxyl group, each having 2 to 4 carbon atoms, B is any one of a polymerization initiator residue, a polymerization-terminating agent residue, H and ##STR45## m is an integer of 1 to 4 and n is an integer of 5 to 100 and a compound having at least one N-substituted unsaturated imido group, thereby forming a prepolymer, a mixing ratio of the cyanate compound or isocyanate compound represented by the general formula (I) to the poly-(p-hydroxystyrene) derivative represented by the general formula (II) is in the range of 20:80 to 80:20 by weight; a step of dissolving the prepolymer in a solvent, thereby forming an impregnation varnish, impregnating a fibrous substrate material with the impregnation varnish, followed by drying, thereby preparing a prepreg; and a step of laminating a plurality of the thus obtained prepregs, thereby obtaining a laminate, and pressing the laminate together with conductor metal foils with heating.

References Cited (Backward Citations)

US4774634A Cited
JPS63281152A Cited
EP0364785A1 Cited

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