Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2001-08-27
2002-10-22
Szekely, Peter (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C523S161000, C524S594000
Reexamination Certificate
active
06469125
ABSTRACT:
TECHNICAL FIELD
The present invention relates generally to resins, more specifically to resins prepared from tall oil pitch, phenolic compounds and formaldehyde or reactive equivalent thereof, and to the use of such resins in inks and coatings, particularly inks for lithographic, gravure and letterpress printing.
BACKGROUND OF THE INVENTION
The reaction products of phenolic compounds and formaldehyde or reactive equivalents thereof are very well known. See, e.g., Peter W. Kopf, “Phenolic Resins,”
Encyclopedia of Polymer Science and Engineering,
vol. 11, pp. 45-94 John Wiley & Sons, N.Y., 1988. These resins may be used as binders in various inks and coatings, however their use is somewhat limited by their high cost. Less expensive phenolic-type resins are prepared when rosin is included among the reactants that form a phenolic resin. These so-called “rosin-phenolic” resins are very widely used today in lithographic printing processes. See, e.g., Roger E. Burke, “Rosin-based Printing Inks,”
Naval Stores,
Chapter 10, Pulp Chemicals Association (1989). However, the increasingly popular use of rosin in other applications, such as tackifiers and other types of resins for various printing and coating processes, has increased competition for an essentially fixed amount of rosin, and increased the incentive to find alternatives to rosin-phenolic resins.
A by-product of the sulfate pulping process is crude tall oil (CTO), and a by-product of CTO fractionation is tall oil pitch. While tall oil pitch has found many commercial applications, there is presently an abundant supply of tall oil pitch that is available at a reasonable price.
Accordingly, there is a need in the art for useful products that can take advantage of the unique composition and reactivity of tall oil pitch. There is also a need in the art for processes that can be used to convert/incorporate tall oil pitch into useful products. There is a further need in the art for viable alternatives to phenolic and rosin-phenolic ink resins. The present invention addresses these long-standing needs, and provides other related advantages, as discussed below.
SUMMARY OF THE INVENTION
Tall oil pitch may be reacted with a phenol-containing organic compound and formaldehyde or reactive equivalent thereof to prepare a resin. The reactants may further include polyhydric organic compound, &agr;,&bgr;-unsaturated carboxyl compound or ester, and hydroxyl-containing non-phenolic organic compound. The resin may be formulated with a colorant to provide an ink for lithographic, gravure or letterpress printing.
Thus, in one aspect, the present invention provides a resin composition prepared from reactants comprising tall oil pitch, phenol-containing organic compound, and formaldehyde or reactive equivalent thereof. The phenol-containing organic compound may be selected from phenol and derivatives of phenol wherein 1-3 aromatic phenol hydrogens are replaced with an equal number of substituents independently selected from hydroxyl, C
1
-C
12
alkyl, C
1
-C
12
alkyl substituted with 1 or 2 groups selected from hydroxyl and phenyl, phenyl, and phenyl substituted with 1 or 2 groups selected from hydroxyl and C
1
-C
12
alkyl. For instance, the phenol-containing organic compound may be a para-C
1
-C
12
alkylphenol. The formaldehyde or reactive equivalent thereof may be formalin or paraformaldehyde. In one aspect, the reactants include at least 55 wt % pitch, or 55-65 wt % pitch, based on the total weight of the reactants, and the equivalent ratio of hydroxyl from phenol-containing organic compound to aldehyde from formaldehyde or reactive equivalent thereof ranges from 1:2 to 1:4. In a preferred aspect, the composition is completely soluble in tetrahydrofuran at 25 wt % solids.
In preparing the composition, the reactants may further include polyhydric non-phenolic organic compound, also known as polyol. The polyol may, in one aspect of the invention, be selected from C
2
-C
36
dihydric compounds, C
3
-C
36
trihydric compounds, C
5
-C
36
tetrahydric compounds, C
5
-C
36
pentahydric compounds and C
6
-C
36
hexahydric compounds. In another aspect, the polyol is selected from ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, butanediol, glycerol, trimethylolpropane, triethylolpropane, pentaerythritol, carbohydrate, dimerized trimethylolpropane, dimerized pentaerythritol and mixtures containing any of these listed alcohols. Thus, in one aspect, the reactants include at least 50 wt % tall oil pitch, the equivalent ratio of hydroxyl from phenol-containing organic compound to aldehyde from formaldehyde or reactive equivalent thereof ranges from 1:2 to 1:4, and the equivalent ratio of hydroxyl from phenol-containing organic compound to hydroxyl from polyol ranges from 1:0.1 to 1:1.
In preparing the composition, the reactants may further include rosin and &agr;,&bgr;-unsaturated carboxylic compound. Thus, in one aspect, the tall oil pitch contributes about 5-40 wt % of the total weight of the reactants, the phenol-containing organic compound and formaldehyde or reactive equivalent thereof each contributes less than 10 wt % of the total weight of the reactants, polyol contributes less than 15 wt % of the total weight of the reactants, &agr;,&bgr;-unsaturated carboxylate compound or ester thereof contributes less than 10 wt % of the total weight of the reactants, and rosin contributes 30-70 wt % of the total weight of the reactants. In a related aspect, the tall oil pitch contributes about 10-25 wt % of the total weight of the reactants, the phenol-containing organic compound and formaldehyde or reactive equivalent thereof each independently contributes about 4-7 wt % of the total weight of the reactants, polyol contributes less than 15 wt % of the total weight of the reactants, &agr;,&bgr;-unsaturated carboxylate compound or ester thereof contributes less than 10 wt % of the total weight of the reactants and rosin contributes 30-70 wt % of the total weight of the reactants.
Thus, in one aspect of the invention, the resin composition is prepared from reactants that include tall oil pitch, rosin, phenol-containing organic compound, formaldehyde or reactive equivalent thereof, &agr;,&bgr;-unsaturated carboxylic acid or ester thereof, and polyhydric non-phenolic organic compound.
The present invention also provide an ink composition that includes any of the resins described herein, in admixture with a colorant. The ink composition may be formulated for lithographic printing, in essentially the same manner as lithographic inks are currently formulated using rosin-phenolic resins. The ink composition may be formulated for gravure printing.
The present invention also provides methods of printing with these ink compositions.
In another aspect, the present invention provides a process for preparing a tall oil pitch-modified phenolic resin. The process include heating, within a temperature range of 100-300° C., reactants that include distilled tall oil that includes pitch, phenol-containing organic compound, formaldehyde or reactive equivalent thereof, and hydroxyl-containing non-phenolic organic compound.
These and other aspects of this invention will become apparent upon reference to the following detailed description.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides for the preparation of useful resins from tall oil pitch, phenol-containing organic compound, and formaldehyde or reactive equivalent thereof. In particular, it has been surprisingly found that pitch may be used to replace some or all of the rosin that is traditionally used to prepare rosin-modified phenolic resins, and yet still provide products that are useful binders in lithographic, gravure and letterpress inks.
The resins of the invention are prepared from components (which may also be called reactants or starting materials) that include tall oil pitch, phenol-containing organic compound (which may also be called a phenolic compound), and formaldehyde or its reactive equivalent. In a preferred embodiment, the components further include a polyhydroxyl
Fontana Thomas A.
West James C.
Arizona Chemical Company
Seed Intellectual Property Law Group PLLC
Szekely Peter
LandOfFree
Tall oil pitch-modified phenolic resin and methods related... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Tall oil pitch-modified phenolic resin and methods related..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Tall oil pitch-modified phenolic resin and methods related... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2984688