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US4205145A Expired / Lapsed US ⏱️ 0.0 years remaining

Resins for printing inks

Assignee: Eneos Corp
•
Filing: 1978-03-16
•
Granted: 1980-05-27
•
Expires: 1998-03-16
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Abstract

Abstract A resin for printing inks, prepared by the reaction of (A) a conjugated double bond-containing five-membered cyclic compound such as dicyclopentadiene, (B) a phenolic compound such as phenol, (C) an unsaturated carboxylic acid such as maleic anhydride and (D) a resol-type phenol resin obtained from phenol or an alkyl-substituted phenol and formaldehyde. In one embodiment, this invention relates to a process for the preparation of said resin for printing inks.

Inventors

  • 👤 Shozo Tsuchiya
  • 👤 Akio Oshima
  • 👤 Hideo Hayashi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 06:36
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/02; C09D11/10; C09D11/102; C09D11/103; Y; Y10; Y10S; Y10S260/00; Y10S260/38

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 225 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR2## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and 1, m and n are each an integer of 0-6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound in a ratio by weight of from 60:40 to 95:5 in the absence or presence of a catalyst at 150°-330° C. for 10 minutes-20 hours to produce a resin, addition reacting the thus produced resin with (C) an unsaturated carboxylic acid in an amount by weight of 2-20 parts per 100 parts by weight of the resin at 150°-250° C. for 30 minutes-7 hours to produce an acid-modified resin and then reacting the thus produced acid-modified resin with (D) a resol-type phenol resin in an amount by weight of 5-40 parts per 100 parts by weight of the acid-modified resin at 160°-300° C. for 30 minutes-15 hours, the resol-type phenol resin (D) being obtained by reacting with formaldehyde in the presence of a basic catalyst phenol or an alkyl-substituted phenol selected from the group consisting of cresol, ethylphenol, isopropylphenol, tert.-butylphenol, tert.-octylphenol and nonylphenol, thereby to prepare the resin for printing inks.
Claim 2
Dependent Claim 225 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR2## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and 1, m and n are each an integer of 0-6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound in a ratio by weight of from 60:40 to 95:5 in the absence or presence of a catalyst at 150°-330° C. for 10 minutes-20 hours to produce a resin, addition reacting the thus produced resin with (C) an unsaturated carboxylic acid in an amount by weight of 2-20 parts per 100 parts by weight of the resin at 150°-250° C. for 30 minutes-7 hours to produce an acid-modified resin and then reacting the thus produced acid-modified resin with (D) a resol-type phenol resin in an amount by weight of 5-40 parts per 100 parts by weight of the acid-modified resin at 160°-300° C. for 30 minutes-15 hours, the resol-type phenol resin (D) being obtained by reacting with formaldehyde in the presence of a basic catalyst phenol or an alkyl-substituted phenol selected from the group consisting of cresol, ethylphenol, isopropylphenol, tert.-butylphenol, tert.-octylphenol and nonylphenol, thereby to prepare the resin for printing inks.
Claim 3
Dependent Claim 227 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR3## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and 1, m and n are each an integer of 0-6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound in a ratio by weight of from 60:40 to 95:5 in the presence of a Friedel-Crafts type catalyst at -30° to 60° C. for 10 minutes-20 hours to produce a resin, addition reacting the thus produced resin with (C) an unsaturated carboxylic acid in an amount by weight of 2-20 parts per 100 parts by weight of the resin at 150°-250° C. for 30 minutes-7 hours to produce an acid-modified resin and then reacting the thus produced acid-modified resin with (D) a resol-type phenol resin in an amount by weight of 5-40 parts per 100 parts by weight of the acid-modified resin at 160°-300° C. for 30 minutes-15 hours, the resol-type phenol resin (D) being obtained by reacting with formaldehyde in the presence of a basic catalyst phenol or an alkyl-substituted phenol selected from the group consisting of cresol, ethylphenol, isopropylphenol, tert.-butylphenol, tert.-octylphenol and nonylphenol, thereby to prepare the resin for printing inks.
Claim 4
Dependent Claim 227 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR3## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and 1, m and n are each an integer of 0-6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound in a ratio by weight of from 60:40 to 95:5 in the presence of a Friedel-Crafts type catalyst at -30° to 60° C. for 10 minutes-20 hours to produce a resin, addition reacting the thus produced resin with (C) an unsaturated carboxylic acid in an amount by weight of 2-20 parts per 100 parts by weight of the resin at 150°-250° C. for 30 minutes-7 hours to produce an acid-modified resin and then reacting the thus produced acid-modified resin with (D) a resol-type phenol resin in an amount by weight of 5-40 parts per 100 parts by weight of the acid-modified resin at 160°-300° C. for 30 minutes-15 hours, the resol-type phenol resin (D) being obtained by reacting with formaldehyde in the presence of a basic catalyst phenol or an alkyl-substituted phenol selected from the group consisting of cresol, ethylphenol, isopropylphenol, tert.-butylphenol, tert.-octylphenol and nonylphenol, thereby to prepare the resin for printing inks.
Claim 5
Dependent Claim 211 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR4## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and l, m and n are each an integer of 0 to 6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound and (C) an unsaturated carboxylic acid at 150°-330° C. for 10 minutes-20 hours in such amounts that the ratio by weight of the compound (A) to the compound (B) is in the range of from 60:40 to 95:5 and the ratio by weight of the compound (C) to the total of the compounds (A) and (B) is in the range of from 2:100 to 20:100 to produce an acid-modified resin and then reacting the thus produced acid-modified resin with (D) a resol-type phenol resin at 160°-300° C. for 30 minutes-15 hours, the resol-type phenol resin (D) being obtained by reacting with formaldehyde in the presence of a basic catalyst phenol or an alkyl-substituted phenol selected from the group consisting of cresol, ethylphenol, isopropylphenol, tert.-butylphenol, tert.-octylphenol and nonylphenol, thereby to prepare the resin for printing inks.
Claim 6
Dependent Claim 211 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR4## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and l, m and n are each an integer of 0 to 6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound and (C) an unsaturated carboxylic acid at 150°-330° C. for 10 minutes-20 hours in such amounts that the ratio by weight of the compound (A) to the compound (B) is in the range of from 60:40 to 95:5 and the ratio by weight of the compound (C) to the total of the compounds (A) and (B) is in the range of from 2:100 to 20:100 to produce an acid-modified resin and then reacting the thus produced acid-modified resin with (D) a resol-type phenol resin at 160°-300° C. for 30 minutes-15 hours, the resol-type phenol resin (D) being obtained by reacting with formaldehyde in the presence of a basic catalyst phenol or an alkyl-substituted phenol selected from the group consisting of cresol, ethylphenol, isopropylphenol, tert.-butylphenol, tert.-octylphenol and nonylphenol, thereby to prepare the resin for printing inks.
Claim 7
Dependent Claim 176 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR5## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and l, m and n are each an integer of 0-6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound, (C) an unsaturated carboxylic acid and (D) resol-type phenol resin at 150°-330° C. for 10 minutes-20 hours in such amounts that the ratio by weight of the compound (A) to the compound (B) is in the range of from 60:40 to 95:5, the ratio by weight of the compound (C) to the total of the compounds (A) and (B) in the range of from 2:100 to 20:100 and the ratio by weight of the compound (D) to the total of the compounds (A), (B) and (C) in the range of from 5:100 to 40:100, thereby to prepare the resin for printing inks.
Claim 8
Dependent Claim 176 words
A process for the preparation of a resin for printing inks, comprising the steps of: reacting (A) a conjugated double bond-containing five-membered cyclic compound represented by the following formula ##STR5## wherein H is hydrogen, R is an organic residue having 1-24 carbon atoms, X is halogen, and l, m and n are each an integer of 0-6 with the total thereof being 6, or a Diels-Alder reaction product thereof, with (B) a phenolic compound, (C) an unsaturated carboxylic acid and (D) resol-type phenol resin at 150°-330° C. for 10 minutes-20 hours in such amounts that the ratio by weight of the compound (A) to the compound (B) is in the range of from 60:40 to 95:5, the ratio by weight of the compound (C) to the total of the compounds (A) and (B) in the range of from 2:100 to 20:100 and the ratio by weight of the compound (D) to the total of the compounds (A), (B) and (C) in the range of from 5:100 to 40:100, thereby to prepare the resin for printing inks.
Claim 9
Dependent Claim 12 words
A resin for printing inks, prepared by the process of claim 1.
Claim 10
Dependent Claim 12 words
A resin for printing inks, prepared by the process of claim 2.
Claim 11
Dependent Claim 12 words
A resin for printing inks, prepared by the process of claim 3.
Claim 12
Dependent Claim 12 words
A resin for printing inks, prepared by the process of claim 4.

References Cited (Backward Citations)

US2521359A Cited
US2778806A Cited
US3083174A Cited
US3887641A Cited
US4028291A Cited
US3969321A Cited
US4085085A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-05-27 1983-11-26 1984-05-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-05-27 1987-11-26 1988-05-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-05-27 1991-11-26 1992-05-27 $7700.00 Window Closed / Lapsed

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