Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2002-08-28
2003-06-03
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031590, C106S031860, C106S031890, C525S404000
Reexamination Certificate
active
06572691
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to ink compositions and to their methods of use.
BACKGROUND OF THE INVENTION
In the preparation of inks for various uses, the inks must possess good wetting properties, especially when used on low-energy substrates, must penetrate absorbent substrates without creating foam, should have good gloss when dry, must have good performance independent of temperature variations, exhibit low tendency to “sling” during high shear applications, i.e. have good spatter resistance, and any surfactants present must not overemulsify the ink.
SUMMARY OF THE INVENTION
The present invention relates to ink compositions possessing the above attributes, which contain at least one of the following surface-active reaction products, which are the reaction products comprised of the following reactants:
A) at least one compound of formula I
R
1
(X)
3
(I)
wherein each X group is a halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R
1
group to form an epoxy group, and R
1
is an alkanetriyl group containing from 3 to 10 carbon atoms; and
B) at least one compound having the formula II
R
2
X(AO)
n
Y (II)
wherein R
2
is a substituted or unsubstituted, saturated or unsaturated, organic group having from 1 to 36 carbon atoms; X is —O—, —S—, or NR
3
— where R
3
is hydrogen or a C
1
-C
18
alkyl group; each AO group is independently an ethyleneoxy, 1,2-propyleneoxy, or 1,2-butyleneoxy group, n is a number of from 0 to 200, preferably from 1 to 100, more preferably from 2 to 20; and Y is hydrogen, or Y can be a mercapto group or an amino group (amino or C
1
-C
6
alkylamino group) in place of a terminal —OH group, provided that when Y is mercapto or an amino group, n is at least 1.
The mole ratio of the linking compound (I) to (II) is from 0.1:1 to 5:1, preferably from 0.6:1 to 2:1, more preferably from 0.8:1 to 2:1 and most preferably from 1.0:1 to 1.5:1.
This invention also relates to methods for using the ink compositions of the invention.
DETAILED DESCRIPTION
Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients or reaction conditions used herein are to be understood as modified in all instances by the term “about”.
In the above compounds of component A), the linking compound of formula I is preferably epichlorohydrin or another epihalohydrin. Also, trihaloalkanes can be used, such as 1,2,3-trichloropropane, 1,2,4-trichlorobutane, 1,3,6-trichlorohexane, and the like. Instead of chlorine in the epihalohydrins and the trihaloalkanes, the corresponding bromine and iodine compounds can also be used, including compounds containing two or even all three of the above halogens.
The component B) compounds of formula II are organic (optionally alkoxylated) alcohols or the corresponding sulfhydryl or amine compounds.
The R
2
group can be a substituted or unsubstituted, saturated or unsaturated hydrocarbon group having from 1 to 36 carbon atoms. Examples of such hydrocarbon groups include linear or branched alkyl groups having from 1 to 36 carbon atoms, preferably from 4 to 22 carbon atoms, linear or branched alkenyl or alkynyl groups having from 2 to 36 carbon atoms, preferably from 4 to 22 carbon atoms, aryl groups having from 6 to 22 carbon atoms, and arenyl groups having from 7 to 36 carbon atoms. Arenyl groups are alkyl-substituted aromatic radicals having a free valence at an alkyl carbon atom such as a benzylic group.
The R
2
group can also be a saturated carbocyclic group, an unsaturated carbocyclic group having one or more multiple bonds, a saturated heterocyclic group, or an unsaturated heterocyclic group having one or more multiple bonds. Any of the above R
2
groups can be substituted groups, i.e. the groups can be single or multiple substituents such as one or more halogen substituents, for example Cl, Fl, I, and Br; a sulfur functionality such as a mercaptan or thio group; a nitrogen functionality such as an amine or amide functionality; an alcohol functionality, a silicon functionality, e.g., a siloxane; an ether functionality, e.g. a C
1
-C
6
alkoxy group; or any combination thereof.
The R
2
group in formula II is preferably a branched chain alkyl group containing from 4 to 36 carbon atoms, preferably from 4 to 12 carbon atoms, and more preferably from 8 to 10 carbon atoms.
When the X group of formula II is an —S— group, the R
2
group will preferably have from about 4 to about 22 carbon atoms, examples of which include but are not limited to, dodecyl mercapto and 1-hexadecanethiol.
When the R
2
X— group of formula II is a secondary or tertiary amino group, the group preferably contains from 4 to 22 carbon atoms, and n is preferably a number of from 1 to 50. Examples of primary and secondary amines useful for obtaining the R
2
X— group include, but are not limited to, dibutyl amine, cyclohexyl amine, isodecyl amine, and dioctylamine.
Optionally an additional component C) can be reacted with the linking agent of formula I and the compound of formula II. A glycidyl ether or amine can be added to the reaction of formula I and formula II. The amount of the glycidyl ether or glycidyl amine is from about 1 to about 20 mole percent based on the moles of the compounds of formula II used in reaction. When the glycidyl ether or glycidyl amine is added, the ratio of component A) plus the glycidyl ether or glycidyl amine to component B) is preferably from about 1.2:1 to about 5:1. Examples of glycidyl ethers include, but are not limited to, PEG 600 diglycidyl ether, TETRONIC™ 701 tetraglycidyl ether, triglycidyl di or triethanolamine, polyoxyethylene (POE) 200 tallow amine diglycidyl ether, propoxylated (POP10) trimethylol propane triglycidyl ether, propoxylated (POP7) pentaerythritol tetraglycidyl ether. Examples of glycidyl amines include, but are not limited to, tetraglycidyl 1,6-hexane diamine, tetraglycidyl JEFFAMINE™ EDR-148, and tetraglycidyl isophorone diamine.
When Y in formula II is an amine or sulfhydryl group, the resulting compounds can be readily prepared from the corresponding alcohols wherein the terminal hydroxy group is replaced by an —SH group or by an amine nitrogen. For example, a compound of formula II where Y is —OH can be subjected to a catalyzed ammoniation (with ammonia, or a lower alkylamine) for replacement of the hydroxyl.
In the compounds of formula II, the AO groups when present are preferably all ethyleneoxy groups. However, as stated above, each OA group can be independently an ethyleneoxy (EO), 1,2-propyleneoxy (PO), or 1,2-butyleneoxy (BO) group, i.e. any one or more of such groups can be present, and they can be present in any order, as well as be present in blocks, e.g. compounds of formula III:
R
2
O(EO)
m
(PO)
p
(BO)
q
H (III)
wherein R
2
has the meaning given above, m is a number of from 0 to 100, preferably from 1 to 50, more preferably from 4 to 50, p is a number of from 0 to 50, e.g. from 1 to 50, and q is a number of from 0 to 50, e.g. from 1 to 50. Compounds of formula III in which R
2
is a branched chain alkyl group having from 4 to 12 carbon atoms, m is a number of from 2 to 20, and p and q are 0 are preferred.
The degree of hydrophilic and hydrophobic properties of the reaction products of components A) and B) can be readily controlled by controlling the type and number of alkyleneoxy groups in component B). For example, the greater the number of ethylenoxy groups present, the greater the water solubility, while the presence of 1,2-propyleneoxy groups and/or 1,2-butylenoxy groups for example, will decrease water solubility.
In general, the compounds of formula III wherein the sum of n, m, and p is at least 1, and especially at least 2 or 3 are preferred for use herein.
The above reaction products can be prepared by the process disclosed in U.S. Pat. No. 5,827,453, the disclosure of which is expressly incorporated herein by reference.
In general, the component A) and B) (and C if present) reactants are rea
Breindel Kenneth
Broadbent Ronald W.
Brown David W.
Wiggins Michael S.
Cognis Corporation
Drach John E.
Klemanski Helene
Millson, Jr. Henry E.
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