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US4224422A Expired / Lapsed US ⏱️ 0.0 years remaining

Modified epoxy resin-polyisocyanate resin system

Assignee: 3M Co
•
Filing: 1979-06-28
•
Granted: 1980-09-23
•
Expires: 1999-06-28
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Abstract

Abstract Curable expoy resin-polyisocyanate systems which incorporate a minor amount of a cationically polymerizable, ethylenically unsaturated monomer and which are catalyzed by a Lewis acid.

Inventors

  • 👤 Harold E. Rude
  • 👤 Richard G. Newell

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 00:00
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/58; C08G18/63; C08G18/637; C08F; C08F299/00; C08F299/02; C08F299/06; C08G18/003; Y; Y10; Y10S; Y10S525/00; Y10S525/936

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 114 words
A curable liquid resin system which comprises (A) 0.01-5.0 parts of one or more Lewis acids, (B) 1-30 parts of one or more polyols which are liquid or soluble waxy solids having hydroxy equivalent weight of from about 30 to 2000, (C) 1-50 parts of one or more polyisocyanates having equivalent weights of up to about 380 and functionalities of from about 2 to about 6, (D) 20-90 parts of one or more epoxy resins having epoxide functionalities greater than one and which are substantially free of hydroxyl groups and (E) 1-40 parts of one or more cationically polymerizable ethylenically unsaturated monomers, the sum of (A), (B), (C), (D) and (E) being 100 parts.
Claim 2
Dependent Claim 114 words
A curable liquid resin system which comprises (A) 0.01-5.0 parts of one or more Lewis acids, (B) 1-30 parts of one or more polyols which are liquid or soluble waxy solids having hydroxy equivalent weight of from about 30 to 2000, (C) 1-50 parts of one or more polyisocyanates having equivalent weights of up to about 380 and functionalities of from about 2 to about 6, (D) 20-90 parts of one or more epoxy resins having epoxide functionalities greater than one and which are substantially free of hydroxyl groups and (E) 1-40 parts of one or more cationically polymerizable ethylenically unsaturated monomers, the sum of (A), (B), (C), (D) and (E) being 100 parts.
Claim 3
Dependent Claim 31 words
A resin system according to claim 1 comprising 0.1 to 2 parts of (A), 1.5-20 parts of (B), 20-40 parts of (C), 40-70 parts of (D) and 5-15 parts of (E).
Claim 4
Dependent Claim 15 words
A resin system according to claim 1 wherein the Lewis acid component is boron trifluoride.
Claim 5
Dependent Claim 13 words
A resin system according to claim 1 wherein the polyol component is glycerol.
Claim 6
Dependent Claim 29 words
A resin system according to claim 1 wherein the polyisocyanate component is a polymethylene-polyphenylisocyanate having a molecular weight of about 380 and an average isocyanate equivalent weight of 133.
Claim 7
Dependent Claim 15 words
A resin system according to claim 1 wherein the epoxy resin component contains 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate.
Claim 8
Dependent Claim 17 words
A resin system according to claim 1 wherein the epoxy resin component contains bisphenol A diglycidyl ether.
Claim 9
Dependent Claim 15 words
A resin system according to claim 1 wherein the ethylenically unsaturated monomer component is styrene.
Claim 10
Dependent Claim 15 words
A resin system according to claim 1 wherein the ethylenically unsaturated monomer component is limonene.
Claim 11
Dependent Claim 146 words
A curable one-part liquid resin system according to claim 1 which comprises rupturable, impermeable microcapsules ranging in size from about 0.1 to 20 microns having (1) shell walls of a crosslinked interfacial polyurethane-polyether reaction product of an aromatic polyisocyanate having an equivalent weight of up to about 380 and a functionality of from about 2 to 6, glycerol and a cycloaliphatic polyepoxide having an equivalent weight of from about 70 to 220 and a functionality of from about 2 to 3, and (2) liquid fills comprising a Lewis acid-glycerol complex, and a Lewis base scavenger for the Lewis acid having a pK b of from about 6 to 11, there being 0.1 to 35 mole percent of the scavenger based on the moles of Lewis acid in the microcapsules, and a liquid mixture of a polyisocyanate, an epoxy resin and a cationically polymerizable, ethylenically unsaturated monomer.
Claim 12
Dependent Claim 95 words
A curable one-part liquid system according to claim 10 which comprises rupturable, impermeable microcapsules ranging in size from about 0.1 to 20 microns having (1) shell walls of a crosslinked interfacial polyurethane-polyether reaction product of a polymethylene polyphenylisocyanate having a molecular weight of about 380 and an average isocyanate equivalentl weight of 133, glycerol and 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, and (2) liquid fills comprising a boron trifluorideglycerol complex, dimethylformamide as the scavenger, and a liquid mixture of an aromatic isocyanate as defined above, bisphenol A diglycidyl ether and an ethylenically unsaturated monomer selected from styrene and limonene.
Claim 13
Dependent Claim 66 words
A curable one-part liquid system according to claim 11 which comprises substantially (A) 0.64 part of boron trifluoride, (B) 2.56 parts of glycerol, (C) 28 parts of the aromatic polysiocyanate, (D) 0.80 part of the cycloaliphatic polyepoxide and 57 parts of the bisphenol A diglycidyl ether, (E) 11 parts of styrene, and 2.4 mole percent of dimethylformamide scavenger based on the amount of boron trifluoride present.
Claim 14
Dependent Claim 66 words
A curable one-part liquid system according to claim 11 which comprises substantially (A) 0.64 part of boron trifluoride, (B) 2.56 parts of glycerol, (C) 27 parts of the aromatic polyisocyanate, (D) 0.80 part of the cycloaliphatic polyepoxide and 56 parts of the bisphenol A diglycidyl ether, (E) 13 parts of limonene, and 2.4 mole percent of dimethylformamide scavenger based on the amount of boron trifluoride present.
Claim 15
Dependent Claim 114 words
A solid, cured, polymeric reaction product of (A) 0.01-5.0 parts of one or more Lewis acid, (B) 1-30 parts of one or more polyols which are liquid or soluble waxy solids having hydroxy equivalent weight of from about 30 to 2000, (C) 1-50 parts of one or more polyisocyanates having equivalent weights of up to about 380 and functionalities of from about 2 to about 6, (D) 20-90 parts of one or more epoxy resins having epoxide functionalities greater than one and which are substantially free of hydroxyl groups, and (E) 1-40 parts of one or more cationically polymerizable, ethylenically unsaturated monomers, the sum of (A), (B), (C), (D) and (E) being 100 parts.
Claim 16
Dependent Claim 114 words
A solid, cured, polymeric reaction product of (A) 0.01-5.0 parts of one or more Lewis acid, (B) 1-30 parts of one or more polyols which are liquid or soluble waxy solids having hydroxy equivalent weight of from about 30 to 2000, (C) 1-50 parts of one or more polyisocyanates having equivalent weights of up to about 380 and functionalities of from about 2 to about 6, (D) 20-90 parts of one or more epoxy resins having epoxide functionalities greater than one and which are substantially free of hydroxyl groups, and (E) 1-40 parts of one or more cationically polymerizable, ethylenically unsaturated monomers, the sum of (A), (B), (C), (D) and (E) being 100 parts.
Claim 17
Dependent Claim 35 words
A cured solid according to claim 14 comprising the reaction product of 0.1 to 2 parts of (A), 1.5-20 parts of (B), 20-40 parts of (C), 40-70 parts of (D) and 5-15 parts of (E).
Claim 18
Dependent Claim 15 words
A cured solid according to claim 14 wherein the Lewis acid component is boron trifluoride.
Claim 19
Dependent Claim 13 words
A cured solid according to claim 14 wherein the polyol component is glycerol.
Claim 20
Dependent Claim 30 words
A cured solid according to claim 14 wherein the polyisocyanate component is a polymethylene polyphenylisocyanate having a molecular weight of about 380 and an average isocyanate equivalent weight of 133.
Claim 21
Dependent Claim 15 words
A cured solid according to claim 14 wherein the epoxy resin component contains 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate.
Claim 22
Dependent Claim 17 words
A cured solid according to claim 14 wherein the epoxy resin component contains bisphenol A diglycidyl ether.
Claim 23
Dependent Claim 15 words
A cured solid according to claim 14 wherein the ethylenically saturated monomer component is styrene.
Claim 24
Dependent Claim 15 words
A cured solid according to claim 14 wherein the ethylenically unsaturated monomer component is limonene.
Claim 25
Dependent Claim 143 words
A solid, cured polymeric reaction product according to claim 14 of rupturable, impermeable microcapsules ranging in size from about 0.1 to 20 microns having (1) shell walls of a crosslinked interfacial polyurethane-polyether reaction product of an aromatic polyisocyanate having an equivalent weight of up to about 380 and a functionality of from about 2 to 6, glycerol and a cycloaliphatic polyepoxide having an equivalent weight of from about 70 to 220 and a functionality of from about 2 to 3, and (2) liquid fills comprising a Lewis acid-glycerol complex, and a Lewis base scavenger for the Lewis acid having a pK b of from about 6 to 11, there being 0.1 to 35 mole percent of the scavenger based on the moles of Lewis acid in the microcapsules, and a mixture of polyisocyanate, an epoxy resin and a cationically polymerizable, ethylenically unsaturated monomer.
Claim 26
Dependent Claim 90 words
A product according to claim 23 of rupturable, impermeable microcapsules ranging in size from about 0.1 to 20 microns having (1) shell walls of a crosslinked interfacial polyurethane-polyether reaction product of a polymethylene polyphenylisocyanate having a molecular weight of about 380 and an average isocyanate equivalent weight of 133, glycerol and 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, and (2) liquid fills comprising a boron trifluorideglycerol complex, dimethylformamide as the scavenger, and a mixture of an aromatic isocyanate as defined above, bisphenol A diglycidyl ether and an ethylenically unsaturated monomer selected from styrene and limonene.
Claim 27
Dependent Claim 61 words
A product according to claim 24 of (A) 0.64 part of boron trifluoride, (B) 2.56 parts of glycerol, (C) 28 parts of the aromatic polyisocyanate, (D) 0.8 part of the cycloaliphatic polyepoxide and 57 parts of the bisphenol A diglycidyl ether, (E) 11 parts of styrene, and 2.4 mole percent of dimethylformamide scavenger based on the amount of boron trifluoride present.
Claim 28
Dependent Claim 61 words
A product according to claim 24 of (A) 0.64 part of boron trifluoride, (B) 2.56 parts of glycerol, (C) 28 parts of the aromatic polyisocyanate, (D) 0.8 part of the cycloaliphatic polyepoxide and 56 parts of the bisphenol A diglycidyl ether, (E) 13 parts of limonene, and 2.4 mole percent of dimethylformamide scavenger based on the amount of boron trifluoride present.

References Cited (Backward Citations)

US3198851A Cited
US3242108A Cited
US3318824A Cited
US3702839A Cited
US3781229A Cited
US4118373A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-09-23 1984-03-24 1984-09-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-23 1988-03-24 1988-09-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-23 1992-03-24 1992-09-23 $7700.00 Window Closed / Lapsed

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