WO2004074572A2 - Paper products softening compositons - Google Patents
Paper products softening compositons Download PDFInfo
- Publication number
- WO2004074572A2 WO2004074572A2 PCT/US2004/004337 US2004004337W WO2004074572A2 WO 2004074572 A2 WO2004074572 A2 WO 2004074572A2 US 2004004337 W US2004004337 W US 2004004337W WO 2004074572 A2 WO2004074572 A2 WO 2004074572A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- saturated
- amphoteric surfactant
- acid
- branched
- chain
- Prior art date
Links
- 0 CC(CCCCNC(*)=O)CCN(CCN(CCC(O)=O)CCN(C1CCCC1)C(*)=O)C(*)=O Chemical compound CC(CCCCNC(*)=O)CCN(CCN(CCC(O)=O)CCN(C1CCCC1)C(*)=O)C(*)=O 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 ethyl eneamine used as a raw material from which the surfactant is derived is tetraethylenepentamine.
- US Patent 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.
- US Patents 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.
- Ri 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:
- 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:
- Ri 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:
- 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.
- FIGURE 1 shows softness test results using of oleic acid and acrylic acid according to the present invention.
- 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 Ci through C 25 alkyl group, whether straight-chain, branched, cyclic, saturated or unsaturated.
- R may be any Ci 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.
- 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.
- Example 1 Preparation of TEPA + 3 moles oleic acid (TEPA triamide) 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 addition the TEPA + 3 moles oleic acid (TEPA triamide) 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 TEPA + 3 moles oleic acid (TEPA triamide) 505.8 grams (1.8 moles) of oleic acid is charged
- the resulting product is a waxy solid at room temperature.
- Total yield 93.0 % of theoretical, as determined by NMR and LR spectra .
- the resulting product is a waxy solid at room temperature.
- Total yield 93.0 % of theoretical, as determined by NMR and TJR. spectra.
- reaction may be terminated when at least
- 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 1L round bottom flask. under nitrogen purge. 162.6 grams of Ethylenamine E-100 is slowly added with stirring
- the temperature of the contents of the flask is maintained at 120°C for 30
- Sample 2 48% (TEPA + 2.5 moles oleic acid + 1.5 moles acrylic acid) 52%o propylene glycol.
- Sample 3 48% (TEPA + 2 moles oleic acid + 2 moles acrylic acid) 52%) propylene glycol.
- Sample 6 70% of sample 1 mixed with 30% of SURFONIC® E-400 MO ("mono- oleate").
- 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 .
- 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.
- SUFRONIC® E-400 MO is an ethoxylated oleic acid surfactant available from Huntsman Company LLC of Houston, Texas.
- 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
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006503569A JP2006518014A (en) | 2003-02-18 | 2004-02-13 | Paper product softening composition |
EP04711213A EP1594601A4 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositons |
US10/545,858 US20060247324A1 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositions |
CA002516297A CA2516297A1 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositons |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/369,263 US20040159415A1 (en) | 2003-02-18 | 2003-02-18 | Paper products softening compositions |
US10/369,263 | 2003-02-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004074572A2 true WO2004074572A2 (en) | 2004-09-02 |
WO2004074572A3 WO2004074572A3 (en) | 2005-01-20 |
Family
ID=32850304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2004/004337 WO2004074572A2 (en) | 2003-02-18 | 2004-02-13 | Paper products softening compositons |
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 |
Family Cites Families (24)
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 |
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 |
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 |
US4441962A (en) * | 1980-10-15 | 1984-04-10 | The Procter & Gamble Company | Soft, absorbent tissue paper |
US4351699A (en) * | 1980-10-15 | 1982-09-28 | 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 |
GB8621086D0 (en) * | 1986-09-01 | 1986-10-08 | Sandoz Ltd | Organic compounds |
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 |
GB9116684D0 (en) * | 1991-08-02 | 1991-09-18 | Exxon Chemical Patents Inc | Corrosion inhibitors |
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 |
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 |
EP0822859B1 (en) * | 1995-04-27 | 2004-04-07 | Goldschmidt Chemical Corporation | Compositions containing diol |
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 |
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 |
US6547928B2 (en) * | 2000-12-15 | 2003-04-15 | The Procter & Gamble Company | Soft tissue paper having a softening composition containing an extensional viscosity modifier deposited thereon |
-
2003
- 2003-02-18 US US10/369,263 patent/US20040159415A1/en not_active Abandoned
-
2004
- 2004-02-13 WO PCT/US2004/004337 patent/WO2004074572A2/en not_active Application Discontinuation
- 2004-02-13 CA CA002516297A patent/CA2516297A1/en not_active Abandoned
- 2004-02-13 US US10/545,858 patent/US20060247324A1/en not_active Abandoned
- 2004-02-13 EP EP04711213A patent/EP1594601A4/en not_active Withdrawn
- 2004-02-13 JP JP2006503569A patent/JP2006518014A/en active Pending
- 2004-12-15 US US11/013,079 patent/US20050153866A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of EP1594601A4 * |
Also Published As
Publication number | Publication date |
---|---|
US20050153866A1 (en) | 2005-07-14 |
US20040159415A1 (en) | 2004-08-19 |
WO2004074572A3 (en) | 2005-01-20 |
JP2006518014A (en) | 2006-08-03 |
CA2516297A1 (en) | 2004-09-02 |
EP1594601A2 (en) | 2005-11-16 |
EP1594601A4 (en) | 2006-10-04 |
US20060247324A1 (en) | 2006-11-02 |
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