US4612254A
Expired / Lapsed
US
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Aromatic carboxylic acid and metal-modified phenolic resins and methods of preparation
Assignee: SUMIKON SPECIALTIES CORP
•
Filing: 1985-03-07
•
Granted: 1986-09-16
•
Expires: 2005-03-07
Abstract
Abstract Novel metal-modified phenolic resins useful in the color developer part of a carbonless copy paper system are disclosed, as well as methods for preparing such resins. The metal-modified phenolic resins are reaction products of an aromatic carboxylic acid and a partial condensation reaction product (an oligomer) of a phenol and an aldehyde. The metal-containing compound is added either to the mixture of phenol and aldehyde in forming the oligomer or to the mixture of aromatic carboxylic acid and the oligomer. The color developer materials of the invention are coated on a paper substrate which forms a part of a pressure sensitive recording paper system. The color developer materials exhibit improved performance over prior art colored developer materials.
Inventors
- 👤 James W. Ginter
- 👤 Donald H. Thorpe
- 👤 Victor F. G. Cooke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 11:12
CPC Classifications
B; B41; B41M; B41M5/00; B41M5/124; B41M5/132; B41M5/155; C; C08; C08G; C08G8/00; C08G8/04; C08G8/08; C08G8/24; C08G8/28; Y; Y10; Y10T; Y10T428/00; Y10T428/25; Y10T428/253; Y10T428/254
Claims Analysis
Total Claims: 82
Claim 1
Independent Claim
54 words
A metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 2
Dependent Claim
54 words
A metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 3
Dependent Claim
21 words
A metal-modified phenolic resin according to claim 1 wherein said phenol is a para-substituted phenol and wherein said aldehyde is formaldehyde.
Claim 4
Dependent Claim
17 words
A metal-modified phenolic resin according to claim 2 wherein said aromatic carboxylic acid is a salicylic acid.
Claim 5
Dependent Claim
15 words
A metal-modified phenolic resin according to claim 3 wherein said metal-containing compound is zinc oxide.
Claim 6
Dependent Claim
31 words
A metal-modified phenolic resin according to claim 4 wherein said para-substituted phenol is para-butyl phenol, para-octyl phenol, para-nonyl phenol, or para-phenyl phenol; and wherein said aromatic carboxylic acid is salicylic acid.
Claim 7
Dependent Claim
22 words
A metal-modified phenolic resin according to claim 5 wherein said oligomer contains on the average between about one to four phenol radicals.
Claim 8
Dependent Claim
50 words
A metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a parasubstituted phenol, which does not contain a carboxyl group, and formaldehyde; (b) salicylic acid; and (c) zinc oxide, said oligomer having at least one reactive group thereon for reacting with said salicylic acid.
Claim 9
Dependent Claim
50 words
A metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a parasubstituted phenol, which does not contain a carboxyl group, and formaldehyde; (b) salicylic acid; and (c) zinc oxide, said oligomer having at least one reactive group thereon for reacting with said salicylic acid.
Claim 10
Dependent Claim
15 words
A metal-modified phenolic resin according to claim 7 wherein said para-substituted phenol is para-nonyl phenol.
Claim 11
Dependent Claim
35 words
A metal-modified phenolic resin according to claim 8 wherein said salicylic acid is present in an amount about 1 to 25 percent by weight based on the weight of the para-nonyl phenol and salicylic acid.
Claim 12
Dependent Claim
35 words
A metal-modified phenolic resin according to claim 9 wherein said salicylic acid is present in an amount about 10 to 18 percent by weight based on the weight of the para-nonyl phenol and salicylic acid.
Claim 13
Dependent Claim
38 words
A metal-modified phenolic resin according to claim 8 wherein the zinc in said zinc oxide is present in an amount about 0.5 to 10 percent by weight based on the weight of the para-nonyl phenol and salicylic acid.
Claim 14
Dependent Claim
38 words
A metal-modified phenolic resin according to claim 11 wherein the zinc in said zinc oxide is present in an amount about 2 to 5 percent by weight based on the weight of the para-nonyl phenol and salicylic acid.
Claim 15
Dependent Claim
56 words
A metal-modified phenolic resin according to claim 8 wherein said salicylic acid is present in an amount about 10 to 18 percent by weight and wherein the zinc in said zinc oxide is present in an amount about 2 to 5 percent by weight, both based on the weight of the para-nonyl phenol and salicylic acid.
Claim 16
Dependent Claim
32 words
An emulsion, suitable for use in a color developer of a pressure sensitive recording paper system, which comprises an emulsion of the metal-modified phenolic resin of claim 1 in an aqueous medium.
Claim 17
Dependent Claim
32 words
An emulsion, suitable for use in a color developer of a pressure sensitive recording paper system, which comprises an emulsion of the metal-modified phenolic resin of claim 4 in an aqueous medium.
Claim 18
Dependent Claim
32 words
An emulsion, suitable for use in a color developer of a pressure sensitive recording paper system, which comprises an emulsion of the metal-modified phenolic resin of claim 7 in an aqueous medium.
Claim 19
Dependent Claim
32 words
An emulsion, suitable for use in a color developer of a pressure sensitive recording paper system, which comprises an emulsion of the metal-modified phenolic resin of claim 13 in an aqueous medium.
Claim 20
Dependent Claim
76 words
A color developer material for coating onto a paper substrate in a pressure sensitive recording paper system, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 21
Dependent Claim
76 words
A color developer material for coating onto a paper substrate in a pressure sensitive recording paper system, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 22
Dependent Claim
37 words
A color developer material according to claim 18 wherein said phenol is a para-substituted phenol; wherein said aldehyde is formaldehyde; wherein said aromatic carboxylic acid is a salicylic acod; and wherein said metal-containing compound is zinc oxide.
Claim 23
Dependent Claim
24 words
A color developer material according to claim 19 wherein said para-substituted phenol is para-nonyl phenol; and wherein said aromatic carboxylic acid is salicylic acid.
Claim 24
Dependent Claim
22 words
A color developer material according to claim 20 wherein said oligomer contains on the average between about one to four phenol radicals.
Claim 25
Dependent Claim
73 words
A color developer material for coating onto a paper substrate in a pressure sensitive recording paper system, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a para-substituted phenol, which does not contain a carboxyl group, and formaldehyde; (b) a salicylic acid; and (c) zinc oxide, said oligomer having at least one reactive group thereon for reacting with said salicylic acid.
Claim 26
Dependent Claim
73 words
A color developer material for coating onto a paper substrate in a pressure sensitive recording paper system, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a para-substituted phenol, which does not contain a carboxyl group, and formaldehyde; (b) a salicylic acid; and (c) zinc oxide, said oligomer having at least one reactive group thereon for reacting with said salicylic acid.
Claim 27
Dependent Claim
56 words
A color developer material according to claim 22 wherein said salicylic acid is present in an amount about 10 to 18 percent by weight, and wherein the zinc is said zinc oxide is present in an amount about 2 to 5 percent by weight, both based on the weight of the para-nonyl phenol and salicylic acid.
Claim 28
Dependent Claim
78 words
A pressure sensitive recording paper system comprising a paper substrate having a coating of a color developer material thereon, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 29
Dependent Claim
78 words
A pressure sensitive recording paper system comprising a paper substrate having a coating of a color developer material thereon, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 30
Dependent Claim
39 words
A pressure sensitive recording paper system according to claim 24 wherein said phenol is a para-substituted phenol; wherein said aldephyde is formaldehyde; wherein said aromatic carboxylic acid is a salicylic acid; and wherein said metal-containing compound is zinc oxide.
Claim 31
Dependent Claim
26 words
A pressure sensitive recording paper system according to claim 25 wherein said para-substituted phenol is para-nonyl phenol; and wherein said aromatic carboxylic acid is salicylic acid.
Claim 32
Dependent Claim
23 words
A pressure sensitive recording paper system according to claim 26 wherein said oligomer contains on the average about one to four phenol radicals.
Claim 33
Dependent Claim
75 words
A pressure sensitive recording paper system comprising a paper substrate having a coating of a color developer material thereon, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a para-substituted phenol, which does not contain a carboxyl group, and formaldehyde; (b) a salicylic acid; and (c) zinc oxide, said oligomer having at least one reactive group thereon for reacting with said salicylic acid.
Claim 34
Dependent Claim
75 words
A pressure sensitive recording paper system comprising a paper substrate having a coating of a color developer material thereon, said color developer material comprising a metal-modified phenolic resin which comprises a reaction product of: (a) a substantially non-novolak oligomer of a para-substituted phenol, which does not contain a carboxyl group, and formaldehyde; (b) a salicylic acid; and (c) zinc oxide, said oligomer having at least one reactive group thereon for reacting with said salicylic acid.
Claim 35
Dependent Claim
58 words
A pressure sensitive recording paper system according to claim 28 wherein said salicylic acid is present in an amount about 1 to 25 percent by weight, and wherein the zinc in said zinc oxide is present in an amount about 0.5 to 10 percent by weight, both based on the weight of the para-nonyl phenol and salicylic acid.
Claim 36
Dependent Claim
58 words
A pressure sensitive recording paper system according to claim 29 wherein said salicylic acid is present in an amount about 10 to 18 percent by weight, and wherein the zinc in said zinc oxide is present in an amount about 2 to 5 percent by weight, both based on the weight of the para-nonyl phenol and salicylic acid.
Claim 37
Dependent Claim
55 words
A process for preparing a metal-modified phenolic resin which comprises reacting: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 38
Dependent Claim
55 words
A process for preparing a metal-modified phenolic resin which comprises reacting: (a) a substantially non-novolak oligomer of a phenol, which does not contain a carboxyl group, and an aldehyde; (b) an aromatic carboxylic acid; and (c) a metal-containing compound, said oligomer having at least one reactive group thereon for reacting with said aromatic carboxylic acid.
Claim 39
Dependent Claim
35 words
A process according to claim 31 wherein said phenol is a para-substituted phenol; wherein said aldehyde is formaldehyde; wherein said aromatic carboxylic acid is a salicylic acid; and wherein said metal-containing compound is zinc oxide.
Claim 40
Dependent Claim
29 words
A process according to claim 32 wherein said para-substituted phenol is para-butyl phenol, para-octyl phenol, para-nonyl phenol, or para-phenyl phenol; and wherein said aromatic carboxylic acid is salicylic acid.
Claim 41
Dependent Claim
56 words
A process for preparing a metal-modified phenolic resin which comprises: (1) reacting a para-substituted phenol, which does not contain a carboxyl group, with an aldehyde in the presence of a catalyst to produce a substantially non-novolak oligomer, and (2) reacting said oligomer with a salicylic acid and a metal oxide to produce a metal-modified phenolic resin.
Claim 42
Dependent Claim
56 words
A process for preparing a metal-modified phenolic resin which comprises: (1) reacting a para-substituted phenol, which does not contain a carboxyl group, with an aldehyde in the presence of a catalyst to produce a substantially non-novolak oligomer, and (2) reacting said oligomer with a salicylic acid and a metal oxide to produce a metal-modified phenolic resin.
Claim 43
Dependent Claim
33 words
A process according to claim 34 wherein said para-substituted phenol is para-nonyl phenol; wherein said aldehyde is formaldehyde; wherein said salicylic acid is salicylic acid; and wherein said metal oxide is zinc oxide.
Claim 44
Dependent Claim
54 words
A process according to claim 35 wherein said salicylic acid is present in an amount about 1 to 25 percent by weight, and wherein the zinc in said zinc oxide is present in an amount about 0.5 to 10 percent by weight, both based on the weight of the para-nonyl phenol and salicylic acid.
Claim 45
Dependent Claim
54 words
A process according to claim 35 wherein said salicylic acid is present in an amount about 10 to 18 percent by weight, and wherein the zinc in said zinc oxide is present in an amount about 2 to 5 percent by weight, both based on the weight of the para-nonyl phenol and salicylic acid.
Claim 46
Dependent Claim
42 words
A process according to claim 31 wherein said phenol is a para-substituted phenol; wherein said aldehyde is formaldehyde; and wherein said oligomer is prepared by the reaction of said para-substituted phenol with formaldehyde under conditions favoring the formation of a resole-type oligomer.
Claim 47
Dependent Claim
47 words
A process according to claim 38 wherein said para-substituted phenol is para-butyl phenol, para-octyl phenol, para-nonyl phenol, or para-phenyl phenol; and wherein said reaction conditions favoring the formation of a resole-type oligomer comprise a reaction temperature of about 50°-100° C. in the presence of an alkaline catalyst.
Claim 48
Dependent Claim
19 words
A process according to claim 39 wherein said alkaline catalyst is an alkali metal hydroxide or a tertiary amine.
Claim 49
Dependent Claim
21 words
A process according to claim 40 wherein said para-substituted phenol is para-nonyl phenol; wherein said reaction temperature is about 70°-100° C.
Claim 50
Dependent Claim
14 words
A process according to claim 41 wherein said reaction temperature is about 100° C.
Claim 51
Dependent Claim
57 words
A process according to claim 39 wherein said aromatic carboxylic acid is salicylic acid; wherein said metal-containing compound is zinc oxide; and wherein said resole-type oligomer is reacted with said salicylic acid and zinc oxide at a pH for the reacting mixture of less than 7.0 and at a reaction temperature of up to about 165° C.
Claim 52
Dependent Claim
28 words
A process according to claim 43 wherein said reaction temperature is initially maintained at about 100° C. and subsequently raised to about 150°-165° C. under a partial vacuum.
Claim 53
Dependent Claim
43 words
A process according to claim 31 wherein said phenol is a para-substituted phenol; wherein said aldehyde is formaldehyde; and wherein said oligomer is prepared by the reaction of said para-substituted phenol with formaldehyde under conditions favoring the formation of a benzyl ether-type oligomer.
Claim 54
Dependent Claim
51 words
A process according to claim 45 wherein said para-substituted phenol is para-butyl phenol, para-octyl phenol, para-nonyl phenol, or para-phenyl phenol; and wherein said reaction conditions favoring the formation of a benzyl ether-type oligomer comprise a reaction temperature of about 100° C. or less in the presence of a metal salt catalyst.
Claim 55
Dependent Claim
31 words
A process according to claim 46 wherein said para-substituted phenol is para-nonyl phenol; wherein said reaction temperature is about 100° C.; and wherein said metal salt catalyst is a zinc salt.
Claim 56
Dependent Claim
22 words
A process according to claim 47 wherein said zinc salt is a salt of a carboxylic acid containing about 1-12 carbon atoms.
Claim 57
Dependent Claim
24 words
A process according to claim 47 wherein said zinc salt of a carboxylic acid is zinc diformate, zinc diacetate, zinc dipropionate, or zinc disalicylate.
Claim 58
Dependent Claim
20 words
A process according to claim 49 wherein said zinc dipropionate is formed in situ by zinc oxide and propionic acid.
Claim 59
Dependent Claim
46 words
A process according to claim 45 wherein said aromatic carboxylic acid is salicylic acid; wherein said metal-containing compound is zinc oxide; and wherein said benzyl ether-type oligomer is reacted with said salicylic acid and zinc oxide at a reaction temperature of up to about 165° C.
Claim 60
Dependent Claim
28 words
A process according to claim 51 wherein said reaction temperature is initially maintained at about 100° C. and subsequently raised to about 150°-165° C. under a partial vacuum.
Claim 61
Dependent Claim
66 words
A method for emulsifying the metal-modified phenolic resin of claim 1 which comprises mixing said resin with a first emulsifying agent and an aqueous medium to obtain a first emulsion of said aqueous medium in said resin, and mixing said first emulsion with a second emulsifying agent and additional amount of said aqueous medium to obtain a second emulsion of said resin in said aqueous medium.
Claim 62
Dependent Claim
66 words
A method for emulsifying the metal-modified phenolic resin of claim 4 which comprises mixing said resin with a first emulsifying agent and an aqueous medium to obtain a first emulsion of said aqueous medium in said resin, and mixing said first emulsion with a second emulsifying agent and additional amount of said aqueous medium to obtain a second emulsion of said resin in said aqueous medium.
Claim 63
Dependent Claim
66 words
A method for emulsifying the metal-modified phenolic resin of claim 7 which comprises mixing said resin with a first emulsifying agent and an aqueous medium to obtain a first emulsion of said aqueous medium in said resin, and mixing said first emulsion with a second emulsifying agent and additional amount of said aqueous medium to obtain a second emulsion of said resin in said aqueous medium.
Claim 64
Dependent Claim
66 words
A method for emulsifying the metal-modified phenolic resin of claim 13 which comprises mixing said resin with a first emulsifying agent and an aqueous medium to obtain a first emulsion of said aqueous medium in said resin, and mixing said first emulsion with a second emulsifying agent and additional amount of said aqueous medium to obtain a second emulsion of said resin in said aqueous medium.
Claim 65
Dependent Claim
35 words
A method for emulsifying the metal-modified phenolic resin of claim 1 which comprises mixing said resin with an emulsifying agent and an aqueous medium to obtain an emulsion of said resin in said aqueous medium.
Claim 66
Dependent Claim
35 words
A method for emulsifying the metal-modified phenolic resin of claim 4 which comprises mixing said resin with an emulsifying agent and an aqueous medium to obtain an emulsion of said resin in said aqueous medium.
Claim 67
Dependent Claim
35 words
A method for emulsifying the metal-modified phenolic resin of claim 7 which comprises mixing said resin with an emulsifying agent and an aqueous medium to obtain an emulsion of said resin in said aqueous medium.
Claim 68
Dependent Claim
35 words
A method for emulsifying the metal-modified phenolic resin of claim 13 which comprises mixing said resin with an emulsifying agent and an aqueous medium to obtain an emulsion of said resin in said aqueous medium.
Claim 69
Dependent Claim
30 words
The metal-modified phenolic resin of claim 1 wherein said oligomer is prepared by the reaction of said phenol with said aldehyde under conditions favoring the formation of a resole-type oligomer.
Claim 70
Dependent Claim
31 words
The metal-modified phenolic resin of claim 1 wherein said oligomer is prepared by the reaction of said phenol with said aldehyde under conditions favoring the formation of a benzyl ether-type oligomer.
Claim 71
Dependent Claim
32 words
An emulsion, suitable for use in a color developer of a pressure sensitive recording paper system, which comprises an emulsion of the metal-modified phenolic resin of claim 61 in an aqueous medium.
Claim 72
Dependent Claim
32 words
An emulsion, suitable for use in a color developer of a pressure sensitive recording paper system, which comprises an emulsion of the metal-modified phenolic resin of claim 62 in an aqueous medium.
Claim 73
Dependent Claim
29 words
The color developer of claim 18 wherein said oligomer is prepared by the reaction of said phenol with said aldehyde under conditions favoring the formation of a resole-type oligomer.
Claim 74
Dependent Claim
30 words
The color developer of claim 18 wherein said oligomer is prepared by the reaction of said phenol with said aldehyde under conditions favoring the formation of a benzyl ether-type oligomer.
Claim 75
Dependent Claim
32 words
The pressure sensitive recording paper system of claim 24 wherein said oligomer is prepared by the reaction of said phenol with said aldehyde under conditions favoring the formation of a resole-type oligomer.
Claim 76
Dependent Claim
33 words
The pressure sensitive recording paper system of claim 24 wherein said oligomer is prepared by the reaction of said phenol with said aldehyde under conditions favoring the formation of a benzyl ether-type oligomer.
Claim 77
Dependent Claim
66 words
A method for emulsifying the metal-modified phenolic resin of claim 61 which comprises mixing said resin with a first emulsifying agent and an aqueous medium to obtain a first emulsion of said aqueous medium in said resin, and mixing said first emulsion with a second emulsifying agent and additonal amount of said aqueous medium to obtain a second emulsion of said resin in said aqueous medium.
Claim 78
Dependent Claim
66 words
A method for emulsifying the metal-modified phenolic resin of claim 62 which comprises mixing said resin with a first emulsifying agent and an aqueous medium to obtain a first emulsion of said aqueous medium in said resin, and mixing said first emulsion with a second emulsifying agent and addional amount of said aqueous medium to obtain a second emulsion of said resin in said aqueous medium.
Claim 79
Dependent Claim
35 words
A method for emulsifying the metal-modified phenolic resin of claim 61 which comprises mixing said resin with an emulsifying agent and an aqueous medium to obtain an emulsion of said resin in said aqueous medium.
Claim 80
Dependent Claim
35 words
A method for emulsifying the metal-modified phenolic resin of claim 62 which comprises mixing said resin with an emulsifying agent and an aqueous medium to obtain an emulsion of said resin in said aqueous medium.
Claim 81
Dependent Claim
23 words
The method of claim 55 wherein said resin mixed with the first emulsifying agent and an aqueous medium is in the molten state.
Claim 82
Dependent Claim
13 words
The method of claim 73 wherein said second emulsifying agent is polyvinyl alcohol.
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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) | 1989-09-15 | 1990-03-17 | 1990-09-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-09-15 | 1994-03-17 | 1994-09-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-09-15 | 1998-03-17 | 1998-09-16 | $7700.00 | Window Closed / Lapsed |