US20040159415A1 - Paper products softening compositions - Google Patents
Paper products softening compositions Download PDFInfo
- Publication number
- US20040159415A1 US20040159415A1 US10/369,263 US36926303A US2004159415A1 US 20040159415 A1 US20040159415 A1 US 20040159415A1 US 36926303 A US36926303 A US 36926303A US 2004159415 A1 US2004159415 A1 US 2004159415A1
- Authority
- US
- United States
- Prior art keywords
- saturated
- amphoteric surfactant
- acid
- branched
- chain
- 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.)
- Abandoned
Links
- 0 [1*]C(=O)C([2*])N([2*])C([1*])=O Chemical compound [1*]C(=O)C([2*])N([2*])C([1*])=O 0.000 description 14
- YYRWUXSLHZARIF-UHFFFAOYSA-N C.CC(=O)O.[H]N(CCN)CCN([H])CCN([H])CCN Chemical compound C.CC(=O)O.[H]N(CCN)CCN([H])CCN([H])CCN YYRWUXSLHZARIF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/22—Agents rendering paper porous, absorbent or bulky
- D21H21/24—Surfactants
Definitions
- compositions useful for treating various surfaces including fibers, textiles, paper, hair, and human skin. More particularly, it relates to compositions and methods for treating metal, paper, and textiles which compositions comprise an amphoteric surfactant derived from ethyleneamines, long-chain fatty acids, and acrylic acid.
- the ethyleneamine used as a raw material from which the surfactant is derived is tetraethylenepentamine.
- U.S. Pat. No. 5,322,630 provides a method of acidizing a subterranean formation with an acqueous acid solution wherein the acid solution contains corrosion inhibiting amounts of an amine derivative prepared by reacting an unsaturated carboxylic acid with (a) fatty amine or polyamine, or (b) a fatty amido amine or polyamine, or (c) a fatty imidazoline amine or polyamine.
- the derivative is characterized by the absence of primary amino groups, and preferably contains only tertiary amino groups.
- amphoteric derivatives of a broad range of fatty polyamines, fatty amidoamines, fatty imidazolines and polyamines which are disclosed as being useful as oilfield corrosion inhibitors.
- U.S. Pat. Nos. 6,004,914; 6,200,938; and 6,369,007 teach amphoteric derivatives of aliphatic polyamines, such as diethylenetriamine or triethylenetetramine reacted with long chain fatty acids, esters or triglycerides from various natural or synthetic sources are effective in the softening/texture modification of substrates such as paper, textiles, human skin surfaces and hair tresses, as well as in applications for metal working and lubrication.
- the polyamines are first reacted with fatty acids, esters or triglycerides derived from various animal, vegetable or synthetic sources ranging in molecular distribution from butyric through erucic acids (e.g.
- milkfat, soy bean oil, rapeseed oil to form polyamines or imidazolines; they are then further reacted with unsaturated or halogenated carboxylic acids, carboxylated epoxy compounds or acid anhydrides (e.g. acrylic acid, itaconic acid, chloroacetic acid, maleic anhydrides octadecenyl anhydride) to form the various amphoteric structures.
- unsaturated or halogenated carboxylic acids e.g. acrylic acid, itaconic acid, chloroacetic acid, maleic anhydrides octadecenyl anhydride
- the present invention relates to amphoteric surfactants that are useful in various applications including paper softener, fabric softener, metal working and lubrication.
- An amphoteric surfactant of the present invention may be made by reacting tetraethylene pentamine (“TEPA”) with 2.5 to 3.0 moles of a fatty acid to form an intermediate amide compound which is then converted to an amphoteric compound by reacting it with 1 to 2 moles of an unsaturated acid species selected from the group consisting of: maleic acid, maleic anhydride, vinyl sulfonic acid, 2-methyl vinyl sulfonic acid, allylsulfonic acid, and acrylic acid.
- TEPA tetraethylene pentamine
- an unsaturated acid species selected from the group consisting of: maleic acid, maleic anhydride, vinyl sulfonic acid, 2-methyl vinyl sulfonic acid, allylsulfonic acid, and acrylic acid.
- x is any integer selected from the group consisting of 4, 5, and 6;
- R 1 in each occurrence is independently any alkyl group having between 5 and 25 carbon atoms, whether straight-chain, branched, cyclic, saturated or unsaturated;
- R 2 in each occurrence is independently selected from the group consisting of: 1) hydrogen; 2) any saturated or unsaturated aliphatic mono- or di-carboxylic acid moiety having one or more carboxyl functional groups and having one or more straight-chain or branched, saturated or un-saturated aliphatic chains containing from 2 to 20 carbon atoms; 3) any saturated or unsaturated aliphatic mono sulfonic acid moiety having one or more —SO 3 H functional groups and having one or more straight-chain or branched, saturated or un-saturated aliphatic chains containing from 2 to 20 carbon atoms; and 4) a radical of the formula:
- R 1 has the same meaning as that ascribed to it above.
- a composition according to the invention comprises a mixture of at least two components each of which comprise different amphoteric surfactants which are represented by the formula:
- R 1 in each occurrence is independently any alkyl group having between 5 and 25 carbon atoms, whether straight-chain, branched, cyclic, saturated or unsaturated
- R 2 in each occurrence is independently selected from the group consisting of: 1) hydrogen; 2) any saturated or unsaturated aliphatic mono- or di-carboxylic acid moiety having one or more carboxyl functional groups and having one or more straight-chain or branched, saturated or un-saturated aliphatic chains containing from 2 to 20 carbon atoms; 3) any saturated or unsaturated aliphatic mono sulfonic acid moiety having one or more —SO 3 H functional groups and having one or more straight-chain or branched, saturated or un-saturated aliphatic chains containing from 2 to 20 carbon atoms; and 4) a radical of the formula:
- R 1 has the same meaning as that ascribed to it above.
- the above-described mixture comprises:
- amphoteric surfactant being present in any amount between 8.0% and 20.0%; the second amphoteric surfactant being present in any amount between 25.0% and 45.0%; and the third amphoteric surfactant being present in any amount between 35.0% and 60.0%, with all percentages being calculated on a weight basis with respect to all of the amphoteric surfactants present which are defined by the above formula.
- An amphoteric surfactant of the present invention is exemplified by the use of TEPA as a raw material, and other amphoteric surfactants according to the invention are readily prepared using the same general procedure but with ethyleneamines such as pentaethylenehexamine, hexaethyleneheptamine, heptaethyleneoctamine, etc.
- An amphoteric surfactant according to the invention may be prepared by first reacting TEPA as a starting material with 2.5 to 3 moles fatty acids, to form an intermediate substituted TEPA polyamide. According to one preferred form of the invention, 3 moles of fatty acid are reacted with 1 mole of TEPA to yield the triamide.
- the polyamide is subsequently reacted with 1 to 2 moles of an unsaturated acid species such as acrylic acid or vinylsulfonic acid to form an amphoteric surfactant.
- an unsaturated acid species such as acrylic acid or vinylsulfonic acid
- 2 moles of acrylic acid are reacted with one mole of polyamide, which is preferably a triamide.
- the resulting amphoteric compounds are useful as softeners for tissue paper, fabrics, hair and skin.
- the resulting amphoteric compounds are also useful as lubricants in metalworking.
- reaction (I) one mole of tetraethylenepentamine is caused to be reacted with three moles of the mono-carboxylic acid in which R may be any C 1 through C 25 alkyl group, whether straight-chain, branched, cyclic, saturated or unsaturated.
- R may be any C 1 through C 25 alkyl group, whether straight-chain, branched, cyclic, saturated or unsaturated.
- the present invention contemplates the use of both cis- and trans-isomers.
- the reactant carboxylic acid is oleic acid, although any other carboxylic acid having between about 7 and 25 carbon atoms may be used, or mixtures thereof.
- the product of the reaction between three moles of the carboxylic acid and TEPA is the triamide shown in formula (II):
- This structure represents the predominant product of such reaction according to the invention.
- a mixture of positional isomers is formed with the carboxylic acid residue being substituted upon the various possible positions of substitution having an active hydrogen atom at which the acid function of the carboxylic acid is capable of reacting, as is known to those skilled in the art.
- the resulting product is a mixture of isomers substituted at the first and second; first and third; first and fourth; first and fifth; second and third; and second and fourth positions.
- the present invention embraces all such positional isomers and mixtures thereof.
- acrylic or other unsaturated carboxylic or sulfonic acid When more than one mole of acrylic or other unsaturated carboxylic or sulfonic acid is reacted, more than one of the possible positions is substituted.
- the present invention embraces all such positional isomers.
- Monomers other than acrylic acid may of course be employed in the role just described for acrylic acid, including unsaturated acid species selected from the group consisting of maleic acid, maleic anhydride, vinyl sulfonic acid, 2-methyl vinyl sulfonic acid, and allylsulfonic acid.
- oleic acid is reacted with TEPA at 144° C. for about 6-10 hours and is subsequently reacted with acrylic acid in the presence of propylene glycol or polyethylene glycol at about 105° C. for about 8 hours, or until the reaction is complete.
- the structures of the reaction product are easily confirmed using NMR and IR spectroscopy.
- any polyalkylene polyamine can be reacted with a fatty acid to yield an amide which is subsequently reacted with acrylic acid to yield an amphoteric surfactants useful in treating hair, skin, paper, textiles and fibers according to the invention.
- TEPA tetraethylene pentamine
- the reaction is considered to be complete when the acid number is below 10 meq/gram (acid numbers referred to in this specification are measured by titrating an aqueous sample using aqueous base which is about 0.1 N to a phenolphthalein end point and calculating the acid number using the relation:
- N the Normality of the base used.
- Ethyleneamine E-100 (Huntsman Corp.) is a mixture of tetraethylenepentamine (10-15% TEPA), pentaethylenehexamine (33-38% PEHA) and hexaethyleneheptamine (45-54% HEHA). 516.4 grams of tall oil fatty acid (“TOFA”) is charged to a 1 L round bottom flask. under nitrogen purge. 162.6 grams of Ethylenamine E-100 is slowly added with stirring under nitrogen, the temperature being kept below 120° C. throughout the addition. Following the addition, the temperature of the contents of the flask is maintained at 120° C. for 30 minutes. Then the temperature is increased to 144° C. and maintained at 144° C. for an additional six hours. The reaction is considered to be complete when the acid number is below 10.
- TOFA tall oil fatty acid
- tissue paper for use in personal care such as facial tissue and bathroom tissue is the softness of such papers.
- test solutions were made up as follows:
- Sample 1 48% (TEPA+3 moles oleic acid+2 moles acrylic acid) 52% propylene glycol.
- Sample 2 48% (TEPA+2.5 moles oleic acid+1.5 moles acrylic acid) 52% propylene glycol.
- Sample 3 48% (TEPA+2 moles oleic acid+2 moles acrylic acid) 52% propylene glycol.
- Sample 4 48% (TEPA+2 moles oleic acid+1 moles acrylic acid) 52% propylene glycol.
- Sample 5 48% (TEPA+3 moles oleic acid+1 moles acrylic acid) 52% propylene glycol.
- Sample 6 70% of sample 1 mixed with 30% of SURFONIC® E-400 MO (“monooleate”).
- Sample 7 70% of sample 2 mixed with 30% of SURFONIC® E-400 MO.
- Sample 8 70% of sample 3 mixed with 30% of SURFONIC® E-400 MO.
- Sample 9 70% of sample 4 mixed with 30% of SURFONIC® E-400 MO.
- Sample 10 70% of sample 5 mixed with 30% of SURFONIC® E-400 MO.
- Sample 11 pure SUFRONIC® E-400 MO (SURFONIC® products are available from Huntsman Corporation)
- Control 1 48% (diethylenetetramine “DETA”+2 moles TOFA (tall oil fatty acid)+1 mole acrylic acid)+52% propylene glycol.
- Control 2 70% of control 1+30% SUFRONIC® E-400 MO.
- (TEPA+2 moles oleic acid+2 moles acrylic acid) means the amphoteric surfactant produced by reacting TEPA with 2 moles of oleic acid, and subsequently reacting the product thereof with 2 moles of acrylic acid.
- the various compositions descried above in samples 1-5 were prepared by simple mixing of the specified amount of glycol and amphoteric surfactant. Similarly, for examples 6-10 the specified amounts of materials were blended together.
- SUFRONIC® E-400 MO is an ethoxylated oleic acid surfactant available from Huntsman Company LLC of Houston, Tex.
Abstract
Description
- This invention relates to compositions useful for treating various surfaces including fibers, textiles, paper, hair, and human skin. More particularly, it relates to compositions and methods for treating metal, paper, and textiles which compositions comprise an amphoteric surfactant derived from ethyleneamines, long-chain fatty acids, and acrylic acid. According to one preferred form of the invention the ethyleneamine used as a raw material from which the surfactant is derived is tetraethylenepentamine.
- U.S. Pat. No. 5,322,630 provides a method of acidizing a subterranean formation with an acqueous acid solution wherein the acid solution contains corrosion inhibiting amounts of an amine derivative prepared by reacting an unsaturated carboxylic acid with (a) fatty amine or polyamine, or (b) a fatty amido amine or polyamine, or (c) a fatty imidazoline amine or polyamine. The derivative is characterized by the absence of primary amino groups, and preferably contains only tertiary amino groups. Disclosed therein are amphoteric derivatives of a broad range of fatty polyamines, fatty amidoamines, fatty imidazolines and polyamines which are disclosed as being useful as oilfield corrosion inhibitors.
- U.S. Pat. Nos. 6,004,914; 6,200,938; and 6,369,007 teach amphoteric derivatives of aliphatic polyamines, such as diethylenetriamine or triethylenetetramine reacted with long chain fatty acids, esters or triglycerides from various natural or synthetic sources are effective in the softening/texture modification of substrates such as paper, textiles, human skin surfaces and hair tresses, as well as in applications for metal working and lubrication. The polyamines are first reacted with fatty acids, esters or triglycerides derived from various animal, vegetable or synthetic sources ranging in molecular distribution from butyric through erucic acids (e.g. milkfat, soy bean oil, rapeseed oil) to form polyamines or imidazolines; they are then further reacted with unsaturated or halogenated carboxylic acids, carboxylated epoxy compounds or acid anhydrides (e.g. acrylic acid, itaconic acid, chloroacetic acid, maleic anhydrides octadecenyl anhydride) to form the various amphoteric structures.
- The present invention relates to amphoteric surfactants that are useful in various applications including paper softener, fabric softener, metal working and lubrication. An amphoteric surfactant of the present invention may be made by reacting tetraethylene pentamine (“TEPA”) with 2.5 to 3.0 moles of a fatty acid to form an intermediate amide compound which is then converted to an amphoteric compound by reacting it with 1 to 2 moles of an unsaturated acid species selected from the group consisting of: maleic acid, maleic anhydride, vinyl sulfonic acid, 2-methyl vinyl sulfonic acid, allylsulfonic acid, and acrylic acid. Thus, the present invention concerns compositions of matter useful for treating paper, textiles, and human skin comprising an amphoteric surfactant represented by the formula:
-
- in which R1 has the same meaning as that ascribed to it above.
-
-
- in which R1 has the same meaning as that ascribed to it above. According to yet a further embodiment, the above-described mixture comprises:
- a) a first amphoteric surfactant, having a value for x of 4;
- b) a second amphoteric surfactant, having a value for x of 5;
- c) a third amphoteric surfactant, having a value for x of 6,
- with the first amphoteric surfactant being present in any amount between 8.0% and 20.0%; the second amphoteric surfactant being present in any amount between 25.0% and 45.0%; and the third amphoteric surfactant being present in any amount between 35.0% and 60.0%, with all percentages being calculated on a weight basis with respect to all of the amphoteric surfactants present which are defined by the above formula.
- An amphoteric surfactant of the present invention is exemplified by the use of TEPA as a raw material, and other amphoteric surfactants according to the invention are readily prepared using the same general procedure but with ethyleneamines such as pentaethylenehexamine, hexaethyleneheptamine, heptaethyleneoctamine, etc. An amphoteric surfactant according to the invention may be prepared by first reacting TEPA as a starting material with 2.5 to 3 moles fatty acids, to form an intermediate substituted TEPA polyamide. According to one preferred form of the invention, 3 moles of fatty acid are reacted with 1 mole of TEPA to yield the triamide. According to a preferred form of the invention, the polyamide is subsequently reacted with 1 to 2 moles of an unsaturated acid species such as acrylic acid or vinylsulfonic acid to form an amphoteric surfactant. According to one preferred form of the invention, 2 moles of acrylic acid are reacted with one mole of polyamide, which is preferably a triamide. The resulting amphoteric compounds are useful as softeners for tissue paper, fabrics, hair and skin. The resulting amphoteric compounds are also useful as lubricants in metalworking.
-
-
- in which the R portion is supplied by the oleic acid.
- This structure represents the predominant product of such reaction according to the invention. In practice, a mixture of positional isomers is formed with the carboxylic acid residue being substituted upon the various possible positions of substitution having an active hydrogen atom at which the acid function of the carboxylic acid is capable of reacting, as is known to those skilled in the art. When fewer than three moles of acid are reacted per mole of TEPA, the resulting product is a mixture of isomers substituted at the first and second; first and third; first and fourth; first and fifth; second and third; and second and fourth positions. The present invention embraces all such positional isomers and mixtures thereof.
-
-
- for the case where one mole of acrylic acid is reacted. When an unsaturated sulfonate such as vinylsulfonic acid or allylsulfonic acid is employed, the carboxylic acid group in the above structure is replaced by the group —SO3H thus providing an amphoteric surfactant with a sulfonate anionic portion. The structure above represents the predominant product of such reaction according to the invention. In practice, a mixture of positional isomers is formed with the acrylic residue being substituted upon the various possible positions of substitution having an active hydrogen atom at which the unsaturated function of the acrylic acid is capable of reacting, as is known to those skilled in the art. When more than one mole of acrylic or other unsaturated carboxylic or sulfonic acid is reacted, more than one of the possible positions is substituted. The present invention embraces all such positional isomers. Monomers other than acrylic acid may of course be employed in the role just described for acrylic acid, including unsaturated acid species selected from the group consisting of maleic acid, maleic anhydride, vinyl sulfonic acid, 2-methyl vinyl sulfonic acid, and allylsulfonic acid.
- According to one preferred form of the invention, oleic acid is reacted with TEPA at 144° C. for about 6-10 hours and is subsequently reacted with acrylic acid in the presence of propylene glycol or polyethylene glycol at about 105° C. for about 8 hours, or until the reaction is complete. The structures of the reaction product are easily confirmed using NMR and IR spectroscopy.
- The following examples are illustrative of the present invention and should not be construed as being delimitive thereof in any way. In general, any polyalkylene polyamine can be reacted with a fatty acid to yield an amide which is subsequently reacted with acrylic acid to yield an amphoteric surfactants useful in treating hair, skin, paper, textiles and fibers according to the invention.
- 505.8 grams (1.8 moles) of oleic acid is charged to a 1 L round bottom flask equipped with a mechanical stirrer and nitrogen purge. 113.6 grams (0.60 moles) tetraethylene pentamine (“TEPA”) is slowly added with stirring under nitrogen at such a rate that the temperature is not permitted to exceed 120° C. Following the addition the temperature of the contents of the flask are maintained at 120° C. for 30 minutes, after which time the heat is increased to cause the reactor contents to reach 144° C., at which temperature the reactor contents are maintained for 6 hours further. Condensate is collected in a Dean-Stark trap (theoretical=32.4 ml). The reaction is considered to be complete when the acid number is below 10 meq/gram (acid numbers referred to in this specification are measured by titrating an aqueous sample using aqueous base which is about 0.1 N to a phenolphthalein end point and calculating the acid number using the relation:
- meq/gram=((B)×(N)×56.1)/(weight of sample in grams)
- in which B=the total number of milliliters of base used; and
- N=the Normality of the base used.
- The resulting product is a waxy solid at room temperature. Total yield=93.0% of theoretical, as determined by NMR and IR spectra. The resulting product is a waxy solid at room temperature. Total yield=93.0% of theoretical, as determined by NMR and IR spectra.
- To a 3-neck 1 L round bottom flask equipped with a mechanical stirrer, nitrogen purge, and addition funnel is charged 130.6 grams of propylene glycol and 98.3 grams (0.1 moles) of the oleic acid triamide of TEPA prepared from example 1 above. The contents of the flask are heated with stirring to 90° C. until the contents became homogeneous. 7.2 grams (0.1 mole) of acrylic acid are added slowly, and the contents of the flask are maintained at 105° C. for 3 hours. Alternatively, the reaction may be terminated when at least 90% of the acrylic acid has reacted, as determined by quantitative IR spectroscopy.
- Ethyleneamine E-100 (Huntsman Corp.) is a mixture of tetraethylenepentamine (10-15% TEPA), pentaethylenehexamine (33-38% PEHA) and hexaethyleneheptamine (45-54% HEHA). 516.4 grams of tall oil fatty acid (“TOFA”) is charged to a 1 L round bottom flask. under nitrogen purge. 162.6 grams of Ethylenamine E-100 is slowly added with stirring under nitrogen, the temperature being kept below 120° C. throughout the addition. Following the addition, the temperature of the contents of the flask is maintained at 120° C. for 30 minutes. Then the temperature is increased to 144° C. and maintained at 144° C. for an additional six hours. The reaction is considered to be complete when the acid number is below 10.
- To a 3-neck 1 L round bottom flask equipped with a mechanical stirrer, nitrogen purge, and addition funnel is charged 120.6 grams of propylene glycol and 98.3 grams (0.1 moles) of the oleic acid triamide of TEPA prepared from example 3 above. The contents of the flask are heated with stirring to 90° C. until the contents became homogeneous. 6.5 grams (0.090 mole) of acrylic acid are added slowly, and the contents of the flask are maintained at 105° C. for 3 hours. Alternatively, the reaction may be terminated when at least 90% of the acrylic acid has reacted, as determined by quantitative IR spectroscopy.
- One important aspect of tissue paper for use in personal care such as facial tissue and bathroom tissue is the softness of such papers. In order to evaluate the effect of a compound according to the present invention, several test solutions were made up as follows:
- Sample 1: 48% (TEPA+3 moles oleic acid+2 moles acrylic acid) 52% propylene glycol.
- Sample 2: 48% (TEPA+2.5 moles oleic acid+1.5 moles acrylic acid) 52% propylene glycol.
- Sample 3: 48% (TEPA+2 moles oleic acid+2 moles acrylic acid) 52% propylene glycol.
- Sample 4: 48% (TEPA+2 moles oleic acid+1 moles acrylic acid) 52% propylene glycol.
- Sample 5: 48% (TEPA+3 moles oleic acid+1 moles acrylic acid) 52% propylene glycol.
- Sample 6: 70% of sample 1 mixed with 30% of SURFONIC® E-400 MO (“monooleate”).
- Sample 7: 70% of sample 2 mixed with 30% of SURFONIC® E-400 MO.
- Sample 8: 70% of sample 3 mixed with 30% of SURFONIC® E-400 MO.
- Sample 9: 70% of sample 4 mixed with 30% of SURFONIC® E-400 MO.
- Sample 10: 70% of sample 5 mixed with 30% of SURFONIC® E-400 MO.
- Sample 11: pure SUFRONIC® E-400 MO (SURFONIC® products are available from Huntsman Corporation)
- Control 1: 48% (diethylenetetramine “DETA”+2 moles TOFA (tall oil fatty acid)+1 mole acrylic acid)+52% propylene glycol.
- Control 2: 70% of control 1+30% SUFRONIC® E-400 MO.
- In the above samples, the terminology reminiscent of “(TEPA+2 moles oleic acid+2 moles acrylic acid)” means the amphoteric surfactant produced by reacting TEPA with 2 moles of oleic acid, and subsequently reacting the product thereof with 2 moles of acrylic acid. The various compositions descried above in samples 1-5 were prepared by simple mixing of the specified amount of glycol and amphoteric surfactant. Similarly, for examples 6-10 the specified amounts of materials were blended together. SUFRONIC® E-400 MO is an ethoxylated oleic acid surfactant available from Huntsman Company LLC of Houston, Tex.
- Solutions for treating tissue paper were prepared by making up a 1.0% solution of each of the above samples in water. Evaluations of the effect of each solution were made by immersing a swatch of untreated tissue in each of the 1.0% aqueous solutions containing the material in the samples above. The treated tissue swatches were held in the solution for one minute, and withdrawn. The treated tissue swatches were then dried in an oven at 25° C. The tissues so treated were evaluated for their softness to the touch by several members of our research staff and each given a rating based on the scale: 0=poor/harsh texture; 1=fair; 2=good; 3=very good; 4=excellent/very soft texture. The results of the softness testing is tabulated in the table I below:
TABLE I softness feel test results Sample ID Softness DI Water 0 Sample 6 2.4 Sample 7 2.4 Sample 8 1.2 Sample 9 1.8 Sample 10 3.8 Sample 11 1.4 Sample 5 4.0 Control 1 2.5 Control 2 2.4 - Sample 6 and sample 7 are comparable to the prior art; however, sample 10 and sample 5 are superior to the prior art. In the graph below is the surface response curve for the above samples. It can be seen from the contour plot below of the softness test results that the maximum performance occurs with 3 moles of oleic acid and 1 mole of acrylic acid:
- Consideration must be given to the fact that although this invention has been described and disclosed in relation to certain preferred embodiments, obvious equivalent modifications and alterations thereof will become apparent to one of ordinary skill in this art upon reading and understanding this specification and the claims appended hereto. Accordingly, the presently disclosed invention is intended to cover all such modifications and alterations, and is limited only by the scope of the claims which follow.
Claims (14)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/369,263 US20040159415A1 (en) | 2003-02-18 | 2003-02-18 | Paper products softening compositions |
CA002516297A CA2516297A1 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositons |
JP2006503569A JP2006518014A (en) | 2003-02-18 | 2004-02-13 | Paper product softening composition |
US10/545,858 US20060247324A1 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositions |
PCT/US2004/004337 WO2004074572A2 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositons |
EP04711213A EP1594601A4 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositons |
US11/013,079 US20050153866A1 (en) | 2003-02-18 | 2004-12-15 | Paper products softening process using amphoteric surfactants |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/369,263 US20040159415A1 (en) | 2003-02-18 | 2003-02-18 | Paper products softening compositions |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/013,079 Continuation-In-Part US20050153866A1 (en) | 2003-02-18 | 2004-12-15 | Paper products softening process using amphoteric surfactants |
US11/545,858 Continuation US20070241250A1 (en) | 2005-10-10 | 2006-10-10 | Angle bracket |
Publications (1)
Publication Number | Publication Date |
---|---|
US20040159415A1 true US20040159415A1 (en) | 2004-08-19 |
Family
ID=32850304
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/369,263 Abandoned US20040159415A1 (en) | 2003-02-18 | 2003-02-18 | Paper products softening compositions |
US10/545,858 Abandoned US20060247324A1 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositions |
US11/013,079 Abandoned US20050153866A1 (en) | 2003-02-18 | 2004-12-15 | Paper products softening process using amphoteric surfactants |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/545,858 Abandoned US20060247324A1 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositions |
US11/013,079 Abandoned US20050153866A1 (en) | 2003-02-18 | 2004-12-15 | Paper products softening process using amphoteric surfactants |
Country Status (5)
Country | Link |
---|---|
US (3) | US20040159415A1 (en) |
EP (1) | EP1594601A4 (en) |
JP (1) | JP2006518014A (en) |
CA (1) | CA2516297A1 (en) |
WO (1) | WO2004074572A2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4633075B2 (en) * | 2007-02-28 | 2011-02-16 | 大王製紙株式会社 | Sanitary tissue paper |
Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3554862A (en) * | 1968-06-25 | 1971-01-12 | Riegel Textile Corp | Method for producing a fiber pulp sheet by impregnation with a long chain cationic debonding agent |
US4351699A (en) * | 1980-10-15 | 1982-09-28 | The Procter & Gamble Company | Soft, absorbent tissue paper |
US4441962A (en) * | 1980-10-15 | 1984-04-10 | The Procter & Gamble Company | Soft, absorbent tissue paper |
US4720383A (en) * | 1986-05-16 | 1988-01-19 | Quaker Chemical Corporation | Softening and conditioning fibers with imidazolinium compounds |
US4940513A (en) * | 1988-12-05 | 1990-07-10 | The Procter & Gamble Company | Process for preparing soft tissue paper treated with noncationic surfactant |
US4941983A (en) * | 1986-09-01 | 1990-07-17 | Sandoz Ltd. | Fluid loss-reducing additives for oil-based well working fluids |
US4959125A (en) * | 1988-12-05 | 1990-09-25 | The Procter & Gamble Company | Soft tissue paper containing noncationic surfactant |
US5240562A (en) * | 1992-10-27 | 1993-08-31 | Procter & Gamble Company | Paper products containing a chemical softening composition |
US5322630A (en) * | 1992-05-14 | 1994-06-21 | Exxon Chemical Patents Inc. | Amine derivatives as corrosion inhibitors |
US5385642A (en) * | 1993-05-13 | 1995-01-31 | The Procter & Gamble Company | Process for treating tissue paper with tri-component biodegradable softener composition |
US5538595A (en) * | 1995-05-17 | 1996-07-23 | The Proctor & Gamble Company | Chemically softened tissue paper products containing a ploysiloxane and an ester-functional ammonium compound |
US5643864A (en) * | 1994-08-19 | 1997-07-01 | Rhone-Poulenc, Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
US5656586A (en) * | 1994-08-19 | 1997-08-12 | Rhone-Poulenc Inc. | Amphoteric surfactants having multiple hydrophobic and hydrophilic groups |
US5753079A (en) * | 1995-04-27 | 1998-05-19 | Witco Corporation | Obtaining enhanced paper production using cationic compositions containing diol and/or diol alkoxylate |
US6004914A (en) * | 1998-08-20 | 1999-12-21 | Mona Industries, Inc. | Amphoteric derivatives of aliphatic polyamines with fatty acids, esters or triglycerides, which are useful for various consumer products and industrial applications |
US6179961B1 (en) * | 1997-10-08 | 2001-01-30 | The Procter & Gamble Company | Tissue paper having a substantive anhydrous softening mixture deposited thereon |
US6245197B1 (en) * | 1999-10-20 | 2001-06-12 | Fort James Corporation | Tissue paper products prepared with an ion-paired softener |
US6315866B1 (en) * | 2000-02-29 | 2001-11-13 | Nalco Chemical Company | Method of increasing the dry strength of paper products using cationic dispersion polymers |
US20020112831A1 (en) * | 2000-12-15 | 2002-08-22 | The Procter & Gamble Company | Soft tissue paper having a softening composition containing an extensional viscosity modifier deposited thereon |
US6458343B1 (en) * | 1999-05-07 | 2002-10-01 | Goldschmidt Chemical Corporation | Quaternary compounds, compositions containing them, and uses thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3091522A (en) * | 1959-04-27 | 1963-05-28 | Dow Chemical Co | Method and composition for improving soil |
JPS55336A (en) * | 1978-06-17 | 1980-01-05 | Kawaken Fine Chem Co Ltd | Preparation of amine amide compound |
US4332737A (en) * | 1980-04-18 | 1982-06-01 | E. I. Du Pont De Nemours And Company | Acid reaction products of polymeric amines |
GB9116684D0 (en) * | 1991-08-02 | 1991-09-18 | Exxon Chemical Patents Inc | Corrosion inhibitors |
-
2003
- 2003-02-18 US US10/369,263 patent/US20040159415A1/en not_active Abandoned
-
2004
- 2004-02-13 EP EP04711213A patent/EP1594601A4/en not_active Withdrawn
- 2004-02-13 US US10/545,858 patent/US20060247324A1/en not_active Abandoned
- 2004-02-13 JP JP2006503569A patent/JP2006518014A/en active Pending
- 2004-02-13 CA CA002516297A patent/CA2516297A1/en not_active Abandoned
- 2004-02-13 WO PCT/US2004/004337 patent/WO2004074572A2/en not_active Application Discontinuation
- 2004-12-15 US US11/013,079 patent/US20050153866A1/en not_active Abandoned
Patent Citations (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3554862A (en) * | 1968-06-25 | 1971-01-12 | Riegel Textile Corp | Method for producing a fiber pulp sheet by impregnation with a long chain cationic debonding agent |
US4351699A (en) * | 1980-10-15 | 1982-09-28 | The Procter & Gamble Company | Soft, absorbent tissue paper |
US4441962A (en) * | 1980-10-15 | 1984-04-10 | The Procter & Gamble Company | Soft, absorbent tissue paper |
US4720383A (en) * | 1986-05-16 | 1988-01-19 | Quaker Chemical Corporation | Softening and conditioning fibers with imidazolinium compounds |
US4941983A (en) * | 1986-09-01 | 1990-07-17 | Sandoz Ltd. | Fluid loss-reducing additives for oil-based well working fluids |
US4959125A (en) * | 1988-12-05 | 1990-09-25 | The Procter & Gamble Company | Soft tissue paper containing noncationic surfactant |
US4940513A (en) * | 1988-12-05 | 1990-07-10 | The Procter & Gamble Company | Process for preparing soft tissue paper treated with noncationic surfactant |
US5322630A (en) * | 1992-05-14 | 1994-06-21 | Exxon Chemical Patents Inc. | Amine derivatives as corrosion inhibitors |
US5240562A (en) * | 1992-10-27 | 1993-08-31 | Procter & Gamble Company | Paper products containing a chemical softening composition |
US5385642A (en) * | 1993-05-13 | 1995-01-31 | The Procter & Gamble Company | Process for treating tissue paper with tri-component biodegradable softener composition |
US5914310A (en) * | 1994-08-19 | 1999-06-22 | Rhodia Inc. | Amphoteric surfactants having multiple hydrophobic and hydrophilic groups |
US5643864A (en) * | 1994-08-19 | 1997-07-01 | Rhone-Poulenc, Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
US5656586A (en) * | 1994-08-19 | 1997-08-12 | Rhone-Poulenc Inc. | Amphoteric surfactants having multiple hydrophobic and hydrophilic groups |
US5753079A (en) * | 1995-04-27 | 1998-05-19 | Witco Corporation | Obtaining enhanced paper production using cationic compositions containing diol and/or diol alkoxylate |
US5538595A (en) * | 1995-05-17 | 1996-07-23 | The Proctor & Gamble Company | Chemically softened tissue paper products containing a ploysiloxane and an ester-functional ammonium compound |
US6179961B1 (en) * | 1997-10-08 | 2001-01-30 | The Procter & Gamble Company | Tissue paper having a substantive anhydrous softening mixture deposited thereon |
US6004914A (en) * | 1998-08-20 | 1999-12-21 | Mona Industries, Inc. | Amphoteric derivatives of aliphatic polyamines with fatty acids, esters or triglycerides, which are useful for various consumer products and industrial applications |
US6200938B1 (en) * | 1998-08-20 | 2001-03-13 | Mona Industries, Inc. | Amphoteric derivatives of aliphatic polyamines with fatty acids, esters or triglycerides for consumer products and industrial applications |
US6369007B1 (en) * | 1998-08-20 | 2002-04-09 | Mona Industries, Inc. | Amphoteric derivatives of aliphatic polyamines with fatty acids, esters or triglycerides, which are useful for various consumer products and industrial applications |
US6458343B1 (en) * | 1999-05-07 | 2002-10-01 | Goldschmidt Chemical Corporation | Quaternary compounds, compositions containing them, and uses thereof |
US6245197B1 (en) * | 1999-10-20 | 2001-06-12 | Fort James Corporation | Tissue paper products prepared with an ion-paired softener |
US6315866B1 (en) * | 2000-02-29 | 2001-11-13 | Nalco Chemical Company | Method of increasing the dry strength of paper products using cationic dispersion polymers |
US20020112831A1 (en) * | 2000-12-15 | 2002-08-22 | The Procter & Gamble Company | Soft tissue paper having a softening composition containing an extensional viscosity modifier deposited thereon |
Also Published As
Publication number | Publication date |
---|---|
JP2006518014A (en) | 2006-08-03 |
CA2516297A1 (en) | 2004-09-02 |
US20060247324A1 (en) | 2006-11-02 |
WO2004074572A2 (en) | 2004-09-02 |
WO2004074572A3 (en) | 2005-01-20 |
EP1594601A4 (en) | 2006-10-04 |
US20050153866A1 (en) | 2005-07-14 |
EP1594601A2 (en) | 2005-11-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH04506804A (en) | Production method of quaternary ammonium compound | |
JP2008516104A (en) | Fatty acid esters of alkanolamines and their use as softeners | |
ZA200105408B (en) | Cationic gemini and related multiple hydrophilic/hydrophobic functional compounds and their use as surfactants. | |
CN101575299A (en) | Method for synthesizing dual-long-chain ester based quaternary ammonium salt | |
MXPA06003567A (en) | Processes for the production of carboxylic acid amides and derivatives thereof. | |
KR100789346B1 (en) | Fabric softener composition | |
JPS63146848A (en) | Quaternary ammonium compound, and its production and use thereof as post-treatment agent of fiber product | |
US20040159415A1 (en) | Paper products softening compositions | |
JPS62286971A (en) | Quaternary 2-alkylimidazolinium salt, manufacture and use | |
US4267350A (en) | Imidazolinium compounds | |
JP3502680B2 (en) | Method for producing quaternary ammonium salt | |
US2781376A (en) | Detergent sulphonic acid and sulphate salts of certain amphoteric detergents | |
CN106758211B (en) | Environment-friendly softening agent and preparation method thereof | |
US5182033A (en) | Polyamide salts | |
JP3502679B2 (en) | Method for producing quaternary ammonium salt | |
Abe et al. | Long chain carboxylic acids containing ether linkage: IV. The antibacterial activities of 0-(2-alkylaminoethyl)-3-oxypropionic and N-(2-alkyloxyethyl)-3-aminopropionic acids | |
US3001997A (en) | Carboxylic acid amides of n-aminoalkylene-heterocyclic amines | |
US2781382A (en) | Detergent sulphonic acid and sulphate salts of certain amphoteric detergents | |
US2781370A (en) | Detergent sulphonic acid and sulphate salts of certain amphoteric detergents | |
US2781378A (en) | Detergent sulphonic acid and sulphate salts of certain amphoteric detergents | |
US4529803A (en) | Process for preparing imidazolinium compounds | |
KR20040014075A (en) | Fabric Softner a composition and making method therefor | |
JP2005503431A (en) | Method for producing cationic surfactant and fiber softener composition containing the same | |
JP3984401B2 (en) | Cationic surfactant composition containing ester bond and method for producing the same | |
RU2008103278A (en) | OLIGOMERIC AMIDOAMINES OR AMIDO SUBSTITUTED QUARTERLY AMMONIUM COMPOUNDS FOR TREATMENT OF TISSUE OR HAIR |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: HUNTSMAN PETROCHEMICAL CORPORATION, TEXAS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:NGUYEN, DUY T.;ASHRAWI, SAMIR S.;REEL/FRAME:013786/0530;SIGNING DATES FROM 20030210 TO 20030211 |
|
AS | Assignment |
Owner name: DEUTSCHE BANK TRUST COMPANY AMERICAS (FORMERLY KNO Free format text: GRANT OF SECURITY INTEREST IN U.S. TRADEMARKS AND PATENTS;ASSIGNOR:HUNTSMAN PETROCHEMICAL CORPORATION;REEL/FRAME:014782/0186 Effective date: 20030930 |
|
AS | Assignment |
Owner name: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS AGENT, NE Free format text: SECURITY AGREEMENT;ASSIGNOR:HUNSTMAN PETROCHEMICAL CORPORATION;REEL/FRAME:015661/0547 Effective date: 20041014 Owner name: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS AGENT,NEW Free format text: SECURITY AGREEMENT;ASSIGNOR:HUNSTMAN PETROCHEMICAL CORPORATION;REEL/FRAME:015661/0547 Effective date: 20041014 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |