WO2001066629A1 - Defoamers for pigment dispersants - Google Patents
Defoamers for pigment dispersants Download PDFInfo
- Publication number
- WO2001066629A1 WO2001066629A1 PCT/US2001/007552 US0107552W WO0166629A1 WO 2001066629 A1 WO2001066629 A1 WO 2001066629A1 US 0107552 W US0107552 W US 0107552W WO 0166629 A1 WO0166629 A1 WO 0166629A1
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- WO
- WIPO (PCT)
- Prior art keywords
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/24—Epihalohydrins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
Definitions
- This invention relates to hydrophobic pigment dispersants, to compositions containing them, and to compounds for defoaming them.
- Pigment dispersants especially hydrophobic pigment dispersants, are known to both generate and stabilize large quantities of foam when added to aqueous compositions containing pigments.
- This foaming propensity is highly disadvantageous, and is particularly troublesome when the dispersants are used to disperse pigments present in water-based paints.
- This invention relates to aqueous-based compositions containing pigments and pigment dispersants, and more particularly to compositions containing pigment dispersants, especially hydrophobic pigment dispersants, and a branched polymer as a defoaming agent.
- the branched polymers used in the above compositions are the reaction products of a linking agent defined by formula (I):
- each Y group is a halogen atom or one Y group is a halogen atom and two Y groups together represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R group to form an epoxy group, and R is an alkanetriyl group containing from 3 to 10 carbon atoms, the preferred linking agent being epichlorohydrin; and at least one compound having the formula (II)
- R 1 X(EO) n (PO) m (BO) p Z (II) wherein R 1 is a substituted or unsubstituted, saturated or unsaturated, organic group having from 4 to 36 carbon atoms; x is -0-, -S-, or -NR 2 - where R 2 is hydrogen or a C ⁇ -C 4 alkyl group; Z is hydrogen, -NHR 2 in place of a terminal -O- group wherein R 2 has the meaning given above, or -SH, in which the -SH group is present in place of a terminal -O- group; n is a number of from 0 to 100, e.g., from 1 to 100; m is a number of from 0 to 50 e.g., from 1 to 50; and p is a number of from 0 to 50 e.g., from 1 to 50; provided that the sum of n, m, and p is at least 1 ; wherein EO represents the residue of ethylene oxide
- formula II compounds wherein the sum of n, m, and p is at least 2, especially at least 3, are preferred.
- R 1 groups include substituted or unsubstituted alkyl groups having from 4 to 36 carbon atoms, preferably from 4 to 22 carbon atoms, alkenyl and alkynyl groups having from 4 to 36 carbon atoms, preferably from 4 to 22 carbon atoms, aryl groups having from 6 to 26 carbon atoms, and arenyl groups having from 7 to 36 carbon atoms.
- the groups can contain single or multiple substitutions such as a halogen substitution, for example Cl, FI, I and
- a sulfur functionality such as a mercaptan or thio group
- a nitrogen functionality such as an amine or amide functionality
- a silicon functionality or any combination thereof.
- the R 1 group can be any substituted or unsubstituted, saturated or unsaturated organic moiety having from 4 to 36 carbon atoms.
- the R 1 groups can be linear or branched alkyl groups, linear or branched alkenyl or alkynyl groups, saturated carbocyclic moieties having one or more multiple bonds, saturated heterocyclic moieties, unsaturated heterocyclic moieties having one or more multiple bonds, substituted linear or branched alkyl groups, substituted linear or branched alkenyl or alkynyl groups, substituted saturated carbocyclic moieties, substituted unsaturated carbocyclic moieties having one or more multiple bonds, substituted saturated heterocyclic moieties, and substituted unsaturated heterocyclic moieties having one or more multiple bonds.
- R 1 can also be an arenyl group.
- Arenyl groups are alkyl-substituted aromatic radicals having a free valence at an alkyl carbon atom such as a benzylic group.
- Alkyl groups having from 4 to 12 carbon atoms are preferred, and alkyl groups having from
- the degree of ethoxylation is preferably from 2 to about 50, more preferably from 3 to about 50, with the most preferred being from 4 to 50, while the degree of propoxylation and butoxylation can vary from 0 to about 50, e.g. from 0 to about 10.
- the degree of propoxylation and/or butoxylation will be determined by the desired degree of water solubility or miscibility. The water solubility or miscibility will ultimately be determined by such factors as the number of carbon atoms in R 1 , the relative amounts EO, PO and BO, and the effect of PO and BO on the biodegradability of the branched polymer.
- the compounds of formula (II) are alkoxylated amines.
- n is a number from 0 to 50, preferably from 1 to 50
- m is a number from 0 to 50
- p is a number from 0 to 50, preferably from 1 to 50, provided that the sum of n, m, and p is at least 1.
- alkoxylated amines useful for the purposes of the invention include but are not limited to, alkoxylated dibutyl amine, alkoxylated dicyclohexyl amine, alkoxylated diethylethanolamine, and alkoxylated dioctylamine.
- the mole ratio of the linking compound (I) to (II) is from about 0.4/1 to about 5/1 , preferably from about 0.4/1 to about 2/1 and more preferably from about 0.6/1 to about 1.6/1.
- an additional component 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 the reaction.
- the ratio of formula (I) to formula (II) plus the glycidyl ether or glycidyl amine is preferably from about 0.8 to about 1.4.
- glycidyl ethers examples include but are not limited to, PEG 600 Diglycidyl ether, TETRONICTM 701 Tetraglycidyl ether, Triglycidyl Dl or Triethanolamine, Polyoxyethylene (POE) 200 Tallow amine diglycidyl ether, Propoxylated (POP10) Trimethylol propane triglycidyl ether, Propoxylated (POP7) Pentaerythritol tetraglycidyl ether.
- PEG 600 Diglycidyl ether examples include but are not limited to, PEG 600 Diglycidyl ether, TETRONICTM 701 Tetraglycidyl ether, Triglycidyl Dl or Triethanolamine, Polyoxyethylene (POE) 200 Tallow amine diglycidyl ether, Propoxylated (POP10) Trimethylol propane triglycidyl ether, Propoxylated (POP7) Pentaerythritol tetraglycid
- Glycidyl amines include but are not limited to, Tetraglycidyl-1 ,6- Hexane diamine, Tetraglycidyl JEFFAMINETM EDR-148, and Tetraglycidyl Isophorone diamine.
- the linking agent of formula (I) is preferably epichlorohydrin although other epihalohydrins can be used.
- trihaloalkanes can be used, such as 1 , 2, 3-trichloropropane, 1 , 2, 4- trichlorobutane, 1 , 3, 6-trichlorohexane and the like.
- chlorine in the epihalohydrins and the trihaloalkanes the corresponding bromine and iodine compounds can also be used, including compounds containing two or even three of the above halogens.
- the corresponding compound of formula II wherein Z is -OH can be converted to -Cl or -Br and then reacted with ammonia or a C C 4 primary amine.
- Z is -SH
- the corresponding compound in which Z is -OH can be converted to the mercaptan by methods well known to the art, e.g. by the reaction of the corresponding -Cl or -Br compound with sodium hydrosulfide.
- Preferred compounds of formula II have the following formula III: R 1 0(EO) n (PO) m (BO) p H (III) in which R 1 , n, m, and p have the meanings given above.
- EO stands for the residue of ethylene oxide
- PO stands for the residue of propylene oxide
- BO stands for the residue of butylene oxide.
- the EO, PO, and BO groups when present, can be in any order with respect to the R 1 X or R 1 0 group, and can be in blocks and/or in random distribution, although the alkoxide groups present are preferably present in the order shown in formulae II and III.
- the reaction between reactants A) and B) can be carried out by reacting the components at a temperature in the range of from 90 to 150°C, preferably from 100 to 110°C, in the presence of a basic catalyst, such as a concentrated aqueous alkali or alkaline earth metal hydroxide. Sodium hydroxide and potassium hydroxide are preferred.
- the reaction is preferably carried out in the presence of an inert organic solvent that azeotropes water, i.e. toluene, and at a temperature that drives off the azeotrope.
- the pigment dispersants are anionic polymeric pigment dispersants, and are usually copolymers or terpolymers of maleic anhydride or maleic acid, e.g. diisobutylene/maleic anhydride copolymer and a terpolymer of maleic anhydride/methacrylic acid/styrene.
- compositions containing a pigment dispersant and a branched polymer can be used as an additive to disperse pigments in aqueous-based products. These compositions can be anhydrous or can be diluted with water if desired.
- the branched polymer is present in the compositions in a quantity of from 0.05% to 20%, preferably from 0.05 to 5% and more preferably from 0.1 to 2.5%, based on the weight of pigment dispersant.
- Such relatively small quantities of branched polymer results in virtually no stable foam when the composition is added to pigment-containing aqueous based products, such as latex paints and the like.
- the branched polymer is miscible in the pigment dispersant, resulting in a clear, homogeneous product.
- compositions containing the pigment dispersant and the branched polymer are used to disperse pigments in aqueous-based paint compositions, substrates coated with the resulting paint exhibit a coating that is even, bubble-free, and has exceptionally high gloss combined with very high water resistance.
- branched polymers are preferably combined with pigment dispersants to be used as additives to pigment - containing aqueous-based products
- the pigment dispersants and the branched polymers can of course be added separately.
- the same relative quantity of branched polymer, based on the quantity of pigment dispersant, is added to the pigment-containing aqueous based product.
- the pigment dispersant whether combined with the branched polymer as an additive, or added separately, is generally added in a quantity of from 0.05 to 2.0% dispersant solids, based on the weight of the pigment in the product.
- the pigment-containing aqueous based products can be paints or other pigment-containing products such as filled adhesives, rubber/polymeric materials (e.g. carpet backing), stucco, grouts, textured coatings, cements, concrete, pigment dispersion concentrates, caulks, sealants, paper coatings, and highly filled thermosetting poymer systems.
- paints or other pigment-containing products such as filled adhesives, rubber/polymeric materials (e.g. carpet backing), stucco, grouts, textured coatings, cements, concrete, pigment dispersion concentrates, caulks, sealants, paper coatings, and highly filled thermosetting poymer systems.
- Latex paint compositions can contain, in addition to pigments, latex polymer particles, thickeners, protective colloids, flow agents, surfactants, catalysts, wetting agents, other defoamers, and plasticizers.
- Pigments that can be used in latex paints include, but are not limited to, titanium dioxide (rutile), mica, calcium carbonate, clay, talc, silica and wollastonite. Some of the above pigments are sometimes referred to as extender pigments. The invention will be illustrated but not limited by the following examples.
- Haas Co. which is a copolymer pigment dispersant prepared by the copolymerization of diisobutylene and maleic anhydride, was prepared in a
- Example 3 The process of Example 1 was repeated except that instead of the reaction product of epichlorohydrin and decyl alcohol • 4EO, the reaction product of epichlorohydrin and dodecyl alcohol • 4EO in a 1 :1 epi : OH ratio was employed. The same results were obtained.
- Example 4 The process of Example 1 was repeated except that instead of the reaction product of epichlorohydrin and decyl alcohol • 4EO, the reaction product of epichlorohydrin and decyl alcohol • 6EO in a 1 :1 epi : OH ratio was employed.
- Example 5 The process of Example 1 was repeated except that instead of the reaction product of epichlorohydrin and decyl alcohol • 4EO, the reaction product of epichlorohydrin and nonyl phenol • 4EO in a 1 :1 epi: OH ratio was employed.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020027011628A KR20020079940A (en) | 2000-03-09 | 2001-03-09 | Defoamers for pigment dispersants |
CA002402292A CA2402292A1 (en) | 2000-03-09 | 2001-03-09 | Defoamers for pigment dispersants |
EP01916512A EP1268638A4 (en) | 2000-03-09 | 2001-03-09 | Defoamers for pigment dispersants |
JP2001565792A JP2003532514A (en) | 2000-03-09 | 2001-03-09 | Antifoaming agent for pigment dispersant |
MXPA02008379A MXPA02008379A (en) | 2000-03-09 | 2001-03-09 | Defoamers for pigment dispersants. |
AU2001243529A AU2001243529A1 (en) | 2000-03-09 | 2001-03-09 | Defoamers for pigment dispersants |
NZ521007A NZ521007A (en) | 2000-03-09 | 2001-03-09 | A composition containing branched polymer defoamers and hydrophobic pigment dispersants |
BR0109071-2A BR0109071A (en) | 2000-03-09 | 2001-03-09 | Composition |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18809100P | 2000-03-09 | 2000-03-09 | |
US60/188,091 | 2000-03-09 | ||
US09/801,509 US6509395B2 (en) | 2000-03-09 | 2001-03-08 | Defoamers for pigment dispersants |
US09/801,509 | 2001-03-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001066629A1 true WO2001066629A1 (en) | 2001-09-13 |
Family
ID=26883712
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/007552 WO2001066629A1 (en) | 2000-03-09 | 2001-03-09 | Defoamers for pigment dispersants |
Country Status (10)
Country | Link |
---|---|
US (1) | US6509395B2 (en) |
EP (1) | EP1268638A4 (en) |
JP (1) | JP2003532514A (en) |
KR (1) | KR20020079940A (en) |
AU (1) | AU2001243529A1 (en) |
BR (1) | BR0109071A (en) |
CA (1) | CA2402292A1 (en) |
MX (1) | MXPA02008379A (en) |
NZ (1) | NZ521007A (en) |
WO (1) | WO2001066629A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6576736B2 (en) | 2001-04-06 | 2003-06-10 | Cognis Corporation | Compounds and compositions useful as surfactants and methods for their preparation |
US6770129B1 (en) * | 2002-01-29 | 2004-08-03 | Cognis Corporation | Coating compositions for paper |
US6960304B1 (en) * | 2002-07-18 | 2005-11-01 | Cognis Corporation | Wastewater treatment |
US20040237841A1 (en) * | 2003-01-29 | 2004-12-02 | Brown David W. | Nonaqueous spray applied compositions and methods for applying them |
CA2582349A1 (en) * | 2004-11-10 | 2006-05-18 | Frank S. Bates | Amphiphilic block copolymer-toughened epoxy resins |
JP2007297558A (en) * | 2006-05-02 | 2007-11-15 | Sony Corp | Recording liquid, recording method using the same and liquid cartridge |
JP6876329B2 (en) * | 2017-10-27 | 2021-05-26 | サンノプコ株式会社 | Dispersion aid |
CN109206609B (en) * | 2018-09-04 | 2020-10-30 | 济南大学 | Preparation and application of hyperbranched polyether air entraining agent |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5623004A (en) * | 1994-05-25 | 1997-04-22 | The Dow Chemical Company | Graft copolymer coating compositions |
US5766812A (en) * | 1997-03-14 | 1998-06-16 | Xerox Corporation | Substrates containing magnetic coatings |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3623988A (en) * | 1970-06-08 | 1971-11-30 | Continental Oil Co | Use of polyether-substituted chlorohydrins as a low-foam, caustic stable cleaning agent |
DE3820000A1 (en) * | 1988-06-11 | 1989-12-14 | Basf Ag | POLYETHER |
US5827453A (en) | 1997-01-14 | 1998-10-27 | Henkel Corporation | Defoaming compositions |
US5895605A (en) | 1997-01-14 | 1999-04-20 | Henkel Corporation | Defoaming compositions |
US6110977A (en) | 1997-01-14 | 2000-08-29 | Henkel Corporation | Alkyl polyglycoside compositions having reduced viscosity and inhibited crystallization |
-
2001
- 2001-03-08 US US09/801,509 patent/US6509395B2/en not_active Expired - Lifetime
- 2001-03-09 EP EP01916512A patent/EP1268638A4/en not_active Withdrawn
- 2001-03-09 NZ NZ521007A patent/NZ521007A/en not_active Application Discontinuation
- 2001-03-09 CA CA002402292A patent/CA2402292A1/en not_active Abandoned
- 2001-03-09 BR BR0109071-2A patent/BR0109071A/en not_active Application Discontinuation
- 2001-03-09 KR KR1020027011628A patent/KR20020079940A/en not_active Application Discontinuation
- 2001-03-09 WO PCT/US2001/007552 patent/WO2001066629A1/en not_active Application Discontinuation
- 2001-03-09 MX MXPA02008379A patent/MXPA02008379A/en not_active Application Discontinuation
- 2001-03-09 AU AU2001243529A patent/AU2001243529A1/en not_active Abandoned
- 2001-03-09 JP JP2001565792A patent/JP2003532514A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5623004A (en) * | 1994-05-25 | 1997-04-22 | The Dow Chemical Company | Graft copolymer coating compositions |
US5766812A (en) * | 1997-03-14 | 1998-06-16 | Xerox Corporation | Substrates containing magnetic coatings |
Non-Patent Citations (1)
Title |
---|
See also references of EP1268638A4 * |
Also Published As
Publication number | Publication date |
---|---|
EP1268638A1 (en) | 2003-01-02 |
JP2003532514A (en) | 2003-11-05 |
BR0109071A (en) | 2003-06-03 |
MXPA02008379A (en) | 2002-12-13 |
CA2402292A1 (en) | 2001-09-13 |
KR20020079940A (en) | 2002-10-19 |
US6509395B2 (en) | 2003-01-21 |
US20010031813A1 (en) | 2001-10-18 |
EP1268638A4 (en) | 2004-12-01 |
AU2001243529A1 (en) | 2001-09-17 |
NZ521007A (en) | 2004-04-30 |
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