CA1107464A - Antistatic agents particularly for coating flat textile articles - Google Patents

Antistatic agents particularly for coating flat textile articles

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Publication number
CA1107464A
CA1107464A CA256,105A CA256105A CA1107464A CA 1107464 A CA1107464 A CA 1107464A CA 256105 A CA256105 A CA 256105A CA 1107464 A CA1107464 A CA 1107464A
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CA
Canada
Prior art keywords
radical
acid
polyalkylene
composition according
glycol ether
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA256,105A
Other languages
French (fr)
Inventor
Dolf Stockhausen
Reinmar Peppmoller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Stockhausen GmbH and Co KG
Original Assignee
Chemische Fabrik Stockhausen GmbH
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Publication of CA1107464A publication Critical patent/CA1107464A/en
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D06M13/332—Di- or polyamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/487—Aziridinylphosphines; Aziridinylphosphine-oxides or sulfides; Carbonylaziridinyl or carbonylbisaziridinyl compounds; Sulfonylaziridinyl or sulfonylbisaziridinyl compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N7/00—Flexible sheet materials not otherwise provided for, e.g. textile threads, filaments, yarns or tow, glued on macromolecular material
    • D06N7/0063—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf
    • D06N7/0071—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf characterised by their backing, e.g. pre-coat, back coating, secondary backing, cushion backing
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N2209/00—Properties of the materials
    • D06N2209/04—Properties of the materials having electrical or magnetic properties
    • D06N2209/046—Anti-static
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/23907—Pile or nap type surface or component
    • Y10T428/23986—With coating, impregnation, or bond
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2418—Coating or impregnation increases electrical conductivity or anti-static quality
    • Y10T442/2459—Nitrogen containing

Abstract

ABSTRACT OF THE DISCLOSURE

An antistatic agent such as for the coating of flat textile articles such as carpets, to prevent static electricity build-up which contains one or more salts of a polymeric acid and an amine of the general formula in which A is H, -OR2, R1 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R2 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R3 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R4 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
X is a bivalent alkylene radical having 1 to 6 carbon atoms;
B is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene glycol ether or polyalkylene imine radical;
n is a small integer from 1 to 6, wherein when n = 1 the grouping

Description

--~

The invention relates to antistatic agents for coating substances which are applied to flat textile artlcles such as carpets, furniture fabrics and furnishing fabrics, to improve their fitness for use.
It i6 known that flat textile articles, especially those made of synthetic fibre material, have a tendency to become electrostati-cally charged when the air has a low humidity, and their suitability is thus considerably adversely affected. The electrostatic charge developed on carpets, in particular, leads to severe disturbance in the operation of precision electronic apparatus (for example data processing systems) as well as to the unpleasant phenomenon of electrostatic discharge "shocks" for people walking on the carpet.
There has been no lack of experiments to develop fibrous materialswhich were alleged to have antistatic properties either through the chemical structure of the fibre composltion or by the use of certain additives. Often metallic fibres have been included in the yarn during spinning, to achieve the same ends. However, it is found that even when a suitable surface structure of the flat textile articles is produced, the antistatic effect is not normally sufficient. Because of the continuous longitudinally aligned antistatic yarn in looped carpet fabric, this performs better than Velour material, where the continuity of the yarn is interrupted by cutting and clipping of the pile at each loop. It is therefore essentially always necessary, especially in cut pile antistatic fabric , to make the coating on the backing conductive also.
In German Patent DT-PS 1 217 916 and German Patent DT-PS
1 286 669, the use of carbon black as an antistatic agent or textile coatings is shown, in natural and synthetic carrier media. However, the dark~ess of the carbon black sets limits on the quantity which can be used. A large number of other antistatic agents, such as quaternary ~1--~74~4 nitrogen compounds, phosphoric acid ester salts, polyethylene glycol alkyl esters or ethers and oxalkylated amines, in carrier media have been used for textile coatings. However, in common with the carbon black these other additives have the considerable disadvantage that in the presence of water and/or organic solvents, they migrate into the textile article and form spots. The appearance of the item i9 thus considerably impaired and may become useless.
We have discovered that the drawbacks of the conventional agents can be avoided when salts of polymeric acids with mono and polyamines or with the reaction products of these amines with alkylene oxides and alkylene imines, are employed .
Polyacrylic acid, polymethacrylic acid, polyitaconic acid, polyvinyl sulphonic acid and the copolymers thereof with one another or with other polymerisaole monomers without an acid function, such as acrylon-itrile, acrylamide, etc., are preferred examples of such polymeric acids.
Mixed polymers of monomers whose polymerisability is generally only possible in conjunction with other monomers, for example maleic acid/styrene mixed polymers, may also be used as such polymeric acids.
The amines used to neutrallse the polymeric acids have the general formula:

~ -Rl in which R3 A is H 9 -OR2, - N

Rl is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;

. . . ~ . . ~

~i7464 R2 is a lower_alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R3 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R4 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
X is a bivalent alkylene radical having 1 to 6 carbon atoms;
B is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene glycol ether or polyalkylene imine radical;
n is a small integer from l to 6, wherein when n = 1, the grouping [~X - N -]

~--Rl may stand for a bivalent 5- or 6-membered heterocyclic radical having one or more hetero atoms, at least one of the radicals R1, R2~ R3, R4 and B

being a polyalkylene imine or polyalkylene glycol ether radical.
Accordingly, primary, secondary or tertiary amines as well as their oxalkylation products and reaction products with alkylene imine are suitable. Not only are open~chain amines suitable but also cyclic amines, including both iso- and heterocyclic imines.
Where the radicals Rl, R2, R3, R4 and B stand for a lower alkyl radical, a hydroxyalkyl radical or an aminoalkyl radical, then these radicals may be identical or different. In this case the alkyl radicals and alkyl proportions in hydroxyalkyl and amlnoalkyl radicals preferably do not have more than 4 carbon atoms. The straight-chain radicals are preferred from among these lower alkyl radicals.
When the radicals Rl, R2, R3 and R4 stand for a polyalkylene imine radical or a polyalkylene glycol ether radical, then the size of these radicals, expressed by the molecular weight, is ordinarily not more than 1500, preferably not more than about 1200.

~ .
~ ~ ~. r:~

~7464 For the blvalen~ alkylene radical X, those alkylene radicals are preferred whlch are derived from the alkylene oxldes whlch are readily available in industry, such as ethylene oxide (2 carbon atoms), propylene oxlde (3 carbon atoms), and butylene oxlde (4 carbon atoms).
For the polyalkylene lmine and polyalkylene glycol ether radicals too, preference is glven to alkylene radlcals having 1 to 6, especially 2 to 4 carbon atoms, which can be derived from readily available alkylene oxides.
When the grouping [ X - N ]

~ -Rl where n = 1, stands for a heterocyclic radical, then an alicyclic radical having at least one nitrogen atom is to be understood.
Nitrogen and/or oxygen may appear as further hetero atoms in the ring system.
Broadly speaking, of the amines grouped under the above formula the amines which are industrially readily available and cheap, are preferred. Suitable amines, which correspond to the above general formula are, for example, the allphatic amines, such as ethylene, diamine, propylene diamine, butylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, dlpropylene triamine, dimethyIaminopropylamlne, amines carrying hydroxyl groups, i.e. amino alcohols, such as dimethylaminoethanol, dimethylaminoisopropanol, triethanolamine, also branched-chaln amines, such as 2-dimethylpropylene diamine.
The different polyimines having molecular weights of up to about 1200 and obtained by polymerisation of polyalkylene -lmines are also suitable. Equally suitable as the above-mentioned amines are, as already mentioned, their reaction products wlth alkylene oxide and ~ ~ -4 ~1~7464 ' ', alkylene imine, Piperidine and piperazine, and morpholine ln particular, are suitable on heterocyclic compounds. Furthermore, ~-(2-aminoethyl)-morpholine, N-(2-aminoethyl)-piperazine and - N-(2-aminoethyl)-pyrrolidine may be used. Here too, their reaction products with alkylene oxide and alkylene imine may likewise be used.
Corresponding to the radicals used in the general formula the claimed ~alts of the polymeric acids are soluble even in non-aqueous media and may be used from such media.
The aqueous solutions of the polymeric salts are used at a concentration of active substance ~ from 0.01 to 20%, preferably from 1 to 5% (~elative to the weight when wet of the coating composition).
The polymeric acids used to form the salts advantageously have a molecular weight of at least 5,000. Preferably, polymers having a lecular weight of between 50,000 and 1,000,000 are used. It can also prove advantageous to use mixtures of the polymeric salts, to achieve an antistatic effect and simultaneously to prevent the formation of spots on the textile item.
Example 1 30.2 parts of a 31% aqueous solution of polyacrylic acid having a molecular weight of about 150,000 and an acid number of 4.22 milliequivalents/gram were mixed, whilst cooling with water, with ~7.9 parts of a triethanolamine polyglycol ether (containing 17 moles of ethylene oxide; titratable bases 1.12 milliequivalents/gram).
The pH value of the neutralised solution is 6.9. By adding 1.9 parts of an approximately 23% aqueous ammonia solution the pH value was lncreased to 7.1.
The resulting product was honey yellow and clear. It had a viscosity of about 5,000 cP (Brookfield RV Sp. 2/5). The solids content was about 7~%.

This antistatic agent was worked into a typical primer compound for a carpet~backing in the following manner:
360 parts of a synthetic polymer latex having 50% solid portions based on 60 parts of butadiene and 40 parts of styrene were taken first. 540 parts of chalk powder ('iJura white BLR 3" manufactured by Messrs. Merkle and having about 20 milliequivalents of bonded titratable alkali) were then stirred in. After homogenisation, 33 parts of the antistatic agent which had previously been diluted with 67 parts of water, were added to the composition and stirred well with it.
Using a lambswool roller, 1000 g/m2 (weight when wet? of the compound prepared in this manner were uniformly applied to DIN
A4 size pieces of Tufting velour pile carpet made of antistatlc fibre of various manufacturers (weight of pile: about 500 g/m2; base fabric made of polypropylene). The coated pieces of carpet were dried for 30 minutes at 80C in a hot air drying cupboard, and, after cooling, conditioned in an atmosphere of 30% relative humidity and 20C for 24 hours. Immediately following the conditioning, the surface resistances of the pile and the coated backing of the specimens as well as their current-flow resistance (pile side up) were measured according to DIN
54345. The results of the measurement can be seen from the attached Table.
Example 2 51.2 parts of the 33% aqueous solution of a copolymer consisting of 90 parts of acrylic acid and 10 parts of itaconic acid having a molecular weight of about 150,000 and an acid number of 4.43 milliequivalents/gram were taken first. The neutralisation to a pH
value of 7.5 was effected analogously to Example 1 with 43.6 parts of a triethylene tetramine polyglycol ether (10 moles of ethylene oxide;
titratable bases 5.2 milliequivalents/gram) and with 5.1 parts of a 23%

' -1~7464 ~ "' ' .
aqueous ammonia solution. The product obtained having a solids content of 62% was a dark red-brown colour and clear. The viscosity ,~ was about 10,500 cP (Brookfield RV Sp. 3/5).
The compound was composed of the following constituents:
360 parts of latex as in Example 1, 540 parts of chalk as in Example 1, 42 parts of antistatic agent, 58 parts of water.

The application and test were carried out as in Example 1.

10 The results of the measurement are given in the attached Table.
Example 3 52,6 parts of the 31% aqueous solution of a polyacrylic acid having a molecular weight of about 150,000 and an acid number of 4.22 milli-equlvalents/gram wére neutralised, as described in Example 1 to a pH value of 7.5 with 46.3 parts of a triethylene tetramine/propylene oxide adduct having 6 moles of propylene oxide (titratable bases 4.8 milli-equivalents/gram) and 1.1 parts of a 23~ aqueous solution of ammonia.
20 The resulting clear, water-soluble product having a solids content of about 63% was brown and highly viscous.The test compound had the following composition:
360 parts of latex as in Example 1, 540 parts of chalk as in Example 1, 40 parts of antistatic agent, 60 parts of water.

Application and test were effected as in Example l; results o the measurement are given in the Table.

r~ - 7 -.

~1~7464 Example 4 42.6 parts of a 34~ aqueous solution of polyacrylic acid having a molecular weight of about 70,000 and an acid number of about 4.73 milliequivalents/gram were mixed with 28.7 parts of a triethylene tetramine polyglycol ether (containlng 10 moles of ethylene oxide, titratable bases 5.2 milliequivalents/gram) and 28.7 parts of a triethanolamine polygylcol ether (containing 7 moles of ethylene oxide, titratable bases 2.0 milliequivalents/gram). The pH value of the neutralised solution was 6.9 and was increased to 7.6 with 1.0 part of 23~ ammonia solution.
The product obtained was brownish yellow and had a viscosity of 24,000 cP (Brookfield RV Sp. 4/5). The solids content was about 72%.
The compound uas composed of the following products:
360 parts of latex as in Example 1, 540 parts of chalk as in Example 1, 34 parts of antistatic agent, 66 parts of water.
Application and test were effected as in Rxample 1. The results of the measurement are summarised in the attached Table.
Example 5 21.3 parts of a 34% aqueous solution of polyacrylic acid, having a molecular weight of about 70,000 and an acid number of 4.73 milliequivalents/gram, and 25.6 pa~ts of a 33% aqueous solution of a copolymer consisting of 90 parts of acrylic acid and 10 parts of itaconic acid having a molecular weight of about 150,000 and an acid number of 4.43 milliequivalents/g,ram, were mixed with 36.1 parts of a triethylene tetramine polyglycol ether (10 moles of ethylene oxide, titratable bases 5.2 milliequivalents/gram ) and with 14.3 parts of a tri-' ...

... . .

ethanolamine polyglycol ether (containing 7 moles of ethylene oxide, titratable bases 2.0 milliequivalents/gram), The pH value W8S adjusted to 7,6 with 2.9 parts of a 23% aqueous solution of ammonia, The product obtained was brownish-yellow and had a viscosity of about 17,000 cP ( Brookfield ~V Sp. 4/5) at a solids content of 67~, The compound was composed of:
360 parts of latex as in Example l, 540 parts of chal~ as in Example l, 39 parts of antistatic agent, 61 parts of water.
Application and test were effected in accordance with Example l, The results of the measurement can be seen from the attached Table, . .
Example 6 71,0 parts of a 30% aqueous solution of polyacrylic acid having a molecular weight of about 150,000 and an acid number of 4,20 milliequivalents/gram, were neutralised with 28,0 grams of piperazine (containing 6 moles of water of crystallisation) and 1,0 part of aqueous concentrated ammonia, The pH value was 7.6.
The product obtained was light yellow and had a viscosity of 280 cP (Brookfield RV Sp. 2/lO). The solids content was about 34.0~.
The compound was composed of the following constituents:
360 parts of latex as in Example 1, 540 parts of chalk as in Example 1, 76 parts of antistatic agent, 24 parts of water.
Application and test were effected as in Example 1. The results can be seen from the Table.

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.1 N ~1 N C`J .
~ 1 ~1 ~1 ~_1 ~/ ~1 .
O ~ O ~
O O
~1 'C ~ ~C PC ~ X
h r~l ~--1 N 1~1 N
:~

,. ' ~ N O O O O O
~_) ~ X ~ ~C t'q ~q tC
~-1 ~ ~;1; `D 0~:1 ~ ~
~ ' ~ .--_ I
8 N _I G O N ~1 ~1 o ~ ~D X X PC :~C ~ X
_ ~ ~`I _ ~ _ N _ _ ~ ~' ~
_l ~ ~d X
O ~ .

~ ~ ~1 N ~ ~ U) .~ ~ o X~ ,~ ~ ~ ~1 .-~
U) ~ O ~ C~ ~ ~ ~
U~ ~ C~ X X X X X
~1 U~ I ~ ~ ~3 ~1 oo 8 8 o ~ o P~ l~l~ h 4_1 L~ _ ~ ~ .

........ .
.

.

Claims (30)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE PROPERTY OR PRIVILEGE
IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An antistatic composition containing water or an organic solvent and an antistatically effective amount of a salt of a polymeric acid with an oxalkylated or amine-alkylated amine of the general formula wherein A is H, -OR2 or R1 is a lower alkyl, hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R2 is a lower alkyl radical, hydroxyalkyl, aminoalkyl, polyalkylene imine or polyglycol ether radical;
R3 is a lower alkyl radical, hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R4 is a lower alkyl radical, hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
X is a bivalent alkylene radical having 1 to 6 carbon atoms;
B is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene glycol ether or polyalkylene imine radical;
n is an integer from 1 to 6 wherein when n = 1 the group may be a bivalent 5- or 6-membered heterocyclic radical having 1 or more hetero atoms, at least one of the radicals R1, R2, R3, R4, and B being a polyalkylene imine or polyalkylene glycol ether radical.
2. An antistatic composition according to claim 1, characterized in that at least one of the radicals R1, R2, R3, and R4 is a polyalkylene imine or polyalkylene glycol ether radical having a molecular weight of not more than 1,500.
3. An antistatic composition according to claim 2, wherein said polyalkylene imine or polyalkylene glycol ether radical has a molecular weight of not more than 1,200.
4. An antistatic composition according to claim 1, wherein the polymeric acid comprises a polymer of polyacrylic acid, polymethacrylic acid, poly-itaconic acid, polyvinyl sulfonic acid or a copolymer thereof.
5. An antistatic composition according to claim 4, wherein the polymeric acid is a copolymer of at least two polymeric acids.
6. An antistatic composition according to claim 4, wherein the polymeric acid is a copolymer of at least one polymeric acid with a monomer free of an acid function.
7. An antistatic composition according to claim 1 wherein said polymeric acid comprises mixed polymers of monomers the polymerizability of which is only possibly in conjunction with other monomers.
8. An antistatic composition according to claim 1 wherein the polymeric or copolymeric acid has a molecular weight of at least 5,000.
9. An antistatic composition according to claim 1 wherein said composition comprises a copolymer of at least two polymeric acids having different molecular weight.
10. An antistatic composition according to claim 1 wherein said composition comprises a copolymer of at least two polymeric acids neutralized by different amines.
11. An antistatic composition according to claim 1 wherein said composition comprises a mixture of different polymeric acids.
12. An antistatic composition according to claim 1,wherein said salt is present in said composition in an amount of 0.01 to 20% by weight.
13. An antistatic composition according to claim 12,wherein said salt is present in said composition in an amount of 1 to 5% by weight.
14. A process for rendering a flat fibrous article antistatic which comprises applying thereto the composition of claim 1.
15. A process for rendering a flat fibrous article antistatic which comprises applying thereto the composition of claim 12.
16. A process according to claim 14 wherein said fibrous article is a carpet.
17. A flat fibrous article comprising textile fibers and the composition of claim 1.
18. A carpet having fiber and a carpet backing, said carpet backing containing the composition of claim 1.
19. An antistatic composition according to claim 1, for the backing of textile materials which includes a primer compound.
20. An antistatic composition according to claim 19, wherein said primer compound is a latex.
21. An antistatic composition according to claim 19, wherein the antistatic agent is one which is soluble in said primer compound.
22. An antistatic composition according to claim 1, for the coating of flat textile articles, carpets, rugs and the like comprising a substantially neutralized polymeric acid, said acid substantially neutralized with an amine of the general formula wherein A is H, -OR2, R1 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R2 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R3 is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
R4 is a lower alkyl radical, a hydroxylalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;
X is a bivalent alkylene radical having 1 to 6 carbon atoms;
B is a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene glycol ether or polyalkylene imine radical;
n is a small integer from 1 to 6, wherein n = 1 the grouping may stand for a bivalent 5- or 6-membered heterocyclic radical having one or more hetero atoms at least one of said R , R2, R3, R4 or B being a polyalkylene imine or polyalkylene glycol ether radical.
23. An antistatic composition according to claim 22, wherein said amine is an alkoxylated triethanolamine.
24. An antistatic composition according to claim 23, wherein said amine is ethoxylated triethanolamine.
25. An antistatic composition according to claim 1, for the coating of flat textile articles, carpets, rugs and the like comprising a substantially neutralized polymeric acid, said polymeric acid neutralized with an amine of the general formula wherein A is H, -OR2, or R1, R2, R3 and R4 are polyalkylene imine or polyalkylene glycol ether radicals;
X is a bivalent alkylene radical having 1 to 6 carbon atoms;
B is a polyalkylene glycol ether or polyalkylene imine radical;
n is a small integer from 1 to 6, wherein when n = 1 the grouping may stand for a bivalent 5- or 6-membered heterocyclic radical having one or more hetero atoms, said polymeric acid being selected from the group consisting of a copolymer of acrylic acid and itaconic acid, a copolymer of acrylic acid and maleic acid, polymethacrylic acid, polyacrylic acid, and a copolymer of styrene and maleic acid, at least one of said R1, R2, R3, R4, and B is a polyalkylene imine or polyalkylene glycol ether radical.
26. An antistatic composition according to claim 1, for the coating of flat textile articles, carpets, rugs and the like comprising a substantially neutralized salt of a polymeric acid, said polymeric acid neutralized with triethylene tetramine polyglycol ether.
27. An antistatic agent according to claim 26, wherein said polymeric acid is neutralized with said triethylene tetramine polyglycol ether and ammonia.
28. An antistatic composition according to claim 22, wherein the polymeric acid has been neutralized to pH 6-8.
29. An antistatic composition according to claim 25 wherein the polymeric acid has been neutralized to pH 6-8.
30. An antistatic composition according to claim 26 wherein the polymeric acid has been neutralized to pH 6-8.
CA256,105A 1975-07-04 1976-06-30 Antistatic agents particularly for coating flat textile articles Expired CA1107464A (en)

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Application Number Priority Date Filing Date Title
DE2529939A DE2529939C3 (en) 1975-07-04 1975-07-04 Antistatic preparation for coating masses of textile fabrics
DEP2529939.2 1975-07-04

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BE (1) BE842439A (en)
CA (1) CA1107464A (en)
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DE (1) DE2529939C3 (en)
DK (1) DK300176A (en)
FR (1) FR2316373A1 (en)
GB (1) GB1560787A (en)
NL (1) NL182824C (en)
PL (1) PL107125B1 (en)

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CH587958A5 (en) 1977-05-13
NL7605281A (en) 1977-01-06
BE842439A (en) 1976-12-01
AT377020B (en) 1985-01-25
DE2529939C3 (en) 1980-10-09
NL182824C (en) 1988-05-16
ATA336676A (en) 1984-06-15
GB1560787A (en) 1980-02-13
FR2316373A1 (en) 1977-01-28
NL182824B (en) 1987-12-16
DE2529939A1 (en) 1977-01-13
DE2529939B2 (en) 1977-06-08
DK300176A (en) 1977-01-05
US4256800A (en) 1981-03-17
FR2316373B1 (en) 1980-10-17
PL107125B1 (en) 1980-01-31

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