EP0027923A2 - Sizing agent - Google Patents

Sizing agent Download PDF

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Publication number
EP0027923A2
EP0027923A2 EP80105990A EP80105990A EP0027923A2 EP 0027923 A2 EP0027923 A2 EP 0027923A2 EP 80105990 A EP80105990 A EP 80105990A EP 80105990 A EP80105990 A EP 80105990A EP 0027923 A2 EP0027923 A2 EP 0027923A2
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EP
European Patent Office
Prior art keywords
polyvinyl alcohol
alkyl
formula
sizing
group
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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.)
Granted
Application number
EP80105990A
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German (de)
French (fr)
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EP0027923B1 (en
EP0027923A3 (en
Inventor
Rolf Dr. Kleber
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Hoechst AG
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Hoechst AG
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Publication of EP0027923A2 publication Critical patent/EP0027923A2/en
Publication of EP0027923A3 publication Critical patent/EP0027923A3/en
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Publication of EP0027923B1 publication Critical patent/EP0027923B1/en
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    • 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
    • D06M15/327—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof
    • D06M15/333—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof of vinyl acetate; Polyvinylalcohol
    • 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
    • D06M13/388—Amine oxides

Definitions

  • Sizing fiber material with polyvinyl alcohol is well known in the art. Especially polyvinyl alcohols with different degrees of saponification, i.e. Different levels of residual acetyl have proven themselves in practice as sizing agents.
  • the invention thus relates to a sizing agent consisting of a polyvinyl alcohol and 1 to 30, preferably example, 5 to 15 wt .-%, based on the polyvinyl alcohol of an amine oxide of the formula wherein R 1 is C 5 -C 22 alkyl, R 2 C 1 -C 22 alkyl or a group of the formula - (CH 2 CH 2 0) n H, n is a number from 1 to 5 and R 3 C 1 -C 5 is alkyl or R 3 is a group of the formula - (CH 2 CH 2 0) m H, if R 2 is an alkyl group with more than 5 C atoms and m is a number from 1 to 10, the sum of n + m is not greater than 10.
  • amine oxides are known from DE-PS 2 326 966. They are derived from naturally occurring fatty acids, which in many cases are mixtures of products with different lengths of the alkyl chain. In addition, as is known, these natural fatty acids can also contain different amounts of unsaturated fatty acids. Accordingly, mixtures of amine oxides with different lengths of the alkyl group are also suitable according to the invention, it also being possible for these groups to be unsaturated.
  • the amine oxides are fully compatible with the types of polyvinyl alcohol and are added to the size bath in the specified concentration. The concentration of the claimed sizing agent in the sizing liquor is usually 2 to 20% by weight.
  • the sizing liquor can also contain other additives such as emulsified fats, mineral oils, starch, starch ether, etc. be added.
  • the sizing agent according to the invention is outstandingly suitable for sizing hydrophobic synthetic fibers, in particular polyester.
  • the addition of the amine oxides gives clear size films of high flexibility.
  • the amine oxides do not exude from the dried films and do not increase their hygroscopicity, but they do increase the adhesive strength of the PVAl solutes.
  • Films were cast from the polyvinyl alcohol a) or the mixtures b) - d) and annealed at 60 ° C. for 2 hours. The films were then evaluated as follows.
  • the thread closure was determined according to Melliand-Textilberichte 58 (1977), pp. 187-194.
  • the pendulum hardness was measured with a hardness tester, the numbers above indicating the number of vibrations that the pendulum executes until it stops.
  • the addition of an amine oxide according to the invention brings about an increase in the flexibility of the size films, the water absorption of which hardly increases.
  • the pendulum hardness as a measure of brittleness also decreases, while the thread closure increases as a decisive criterion for the adhesive strength.
  • the fleets contain approx. 4% of the products a) - d) and are loaded with 200% of the fleet. After drying at approx. 150 ° C (cylinder drying machines), the chains contain approx. 8% solids. When Abweben the chain showing a higher thread break numbers, while the 'b chains can be interwoven to d satisfactory.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Schlichtemittel bestehend aus einem Polyvinylalkohol und 1 bis 30, vorzugsweise 5 bis 15 Gew.%, bezogen auf den Polyvinylalkohol, eines Aminoxids der Formel <IMAGE> wobei R1 C5-C22-Alkyl, R2 C1-C22-Alkyl oder eine Gruppe der Formel -(CH2CH2O)nH, n eine Zahl von 1 bis 5 und R3 C1-C5-Alkyl ist oder R3 ist eine Gruppe der Formel -(CH2CH2O)mH, wenn R2 für eine Alkylgruppe mit mehr als 5 C-Atomen steht und m ist eine Zahl von 1 bis 10, wobei die Summe von n + m nicht größer als 10 ist.Sizing agents consisting of a polyvinyl alcohol and 1 to 30, preferably 5 to 15% by weight, based on the polyvinyl alcohol, of an amine oxide of the formula <IMAGE> where R1 is C5-C22-alkyl, R2 C1-C22-alkyl or a group of the formula - (CH2CH2O) nH, n is a number from 1 to 5 and R3 is C1-C5-alkyl or R3 is a group of the formula - (CH2CH2O) mH when R2 is an alkyl group with more than 5 C atoms and m is one Number from 1 to 10, where the sum of n + m is not greater than 10.

Description

Das Schlichten von Fasermaterial mit Polyvinylalkohol (PVA1) ist in der Technik gut bekannt. Besonders Polyvinylalkohole mit unterschiedlichem Verseifungsgrad, d.h. unterschiedlichem Restacetylgehalt haben sich in der Praxis als Schlichtemittel bewährt.Sizing fiber material with polyvinyl alcohol (PVA1) is well known in the art. Especially polyvinyl alcohols with different degrees of saponification, i.e. Different levels of residual acetyl have proven themselves in practice as sizing agents.

Der Einsatz von Polyvinylalkohol beim Schlichten von Filamenten ist aber in der Praxis nicht unumstritten, da speziell hydrophobe Filamente in Abhängigkeit vom Polymerisationsgrad des Polyvinylalkohols stark unterschiedliche Schlichteergebnisse zeigen. Finch beschreibt in "Polyvinylalkohole S. 261 ff" die Schwierigkeiten für Polyvinylalkohole als Schlichtemittel bei hydrophoben Filamenten, z.B. Polyester. Der PVA1-Schlichtefilm ist auf diesen Fäden sehr spröde und kann deshalb beim Weben durch Absplittern Webfehler verursachen. Verbesserungen bringen laut Finch (loc. cit.), Zusätze von plastifizierenden Additiven und Acrylatschlichten, die in Mischung mit dem Polyvinylalkohol eingesetzt werden. Jedoch können diese Additive den Polyvinylalkoholfilm klebrig und zäh machen. Die zugemischte Acrylatschlichte haftet zwar sehr gut am Polyester, jedoch ist die Acrylatschlichte hygroskopisch und in der Haftlänge und Festigkeit dem Polyvinylalkohol deutlich unterlegen. Das Problem der Empfindlichkeit von Acrylatschlichten bei Filamenten gegenüber Spulölen und Spinnpräparation soll hier nur ergänzend erwähnt werden.The use of polyvinyl alcohol in the sizing of filaments is not without controversy in practice, since hydrophobic filaments in particular show very different sizing results depending on the degree of polymerization of the polyvinyl alcohol. Finch in "Polyvinyl alcohols p. 261 ff" describes the difficulties for polyvinyl alcohols as sizing agents in hydrophobic filaments, e.g. Polyester. The PVA1 size film is very brittle on these threads and can therefore cause weaving errors due to splintering during weaving. According to Finch (loc. Cit.), Improvements result in additions of plasticizing additives and acrylate sizes, which are used in a mixture with the polyvinyl alcohol. However, these additives can make the polyvinyl alcohol film sticky and tough. The admixed acrylate size adheres very well to the polyester, but the acrylate size is hygroscopic and clearly inferior in length and strength to the polyvinyl alcohol. The problem of the sensitivity of acrylic sizes in filaments to winding oils and spin preparation should only be mentioned here in addition.

Es wurde nun gefunden, daß man Schlichten aus Polyvinylalkohol sehr flexibel und weich machen kann, so daß sie mit sehr gutem Erfolg für das Schlichten hydrophober Fasern eingesetzt werden können, wenn man den üblichen Polyvinylalkoholschlichten ein Aminoxid zusetzt.It has now been found that sizes made from polyvinyl alcohol can be made very flexible and soft, so that they can be used with very good results for the size of hydrophobic fibers if an amine oxide is added to the usual polyvinyl alcohol sizes.

Gegenstand der Erfindung ist somit ein Schlichtemittel bestehend aus einem Polyvinylalkohol und 1 bis 30, vorzugsweise 5 bis 15 Gew.-%, bezogen auf den Polyvinylalkohol eines Aminoxids der Formel

Figure imgb0001
wobei R 1 C5-C22-Alkyl, R2 C1-C22-Alkyl oder eine Gruppe der Formel -(CH2CH20)nH, n eine Zahl von 1 bis 5 und R3 C1-C5-Alkyl ist oder R3 ist eine Gruppe der Formel -(CH2CH20)mH, wenn R2 für eine Alkylgruppe mit mehr als 5 C-Atomen steht und m ist eine Zahl von 1 bis 10, wobei die Summe von n + m nicht größer als 10 ist.The invention thus relates to a sizing agent consisting of a polyvinyl alcohol and 1 to 30, preferably example, 5 to 15 wt .-%, based on the polyvinyl alcohol of an amine oxide of the formula
Figure imgb0001
 wherein R 1 is C 5 -C 22 alkyl, R 2 C 1 -C 22 alkyl or a group of the formula - (CH 2 CH 2 0) n H, n is a number from 1 to 5 and R 3 C 1 -C 5 is alkyl or R 3 is a group of the formula - (CH 2 CH 2 0) m H, if R 2 is an alkyl group with more than 5 C atoms and m is a number from 1 to 10, the sum of n + m is not greater than 10.

Diese Aminoxide sind aus der DE-PS 2 326 966 bekannt. Sie leiten sich ab von natürlich vorkommenden Fettsäuren, die in vielen Fällen Gemische darstellen von Produkten mit unterschiedlicher Länge der Alkylkette. Daneben können diese natürlichen Fettsäuren bekanntlich auch unterschiedliche Mengen an ungesättigten Fettsäuren enthalten. Dementsprechend kommen erfindungsgemäß auch Mischungen von Aminoxiden mit unterschiedlicher Länge der Alkylgruppe infrage, wobei diese Gruppen außerdem ungesättigt sein können. Die Aminoxide sind mit den Polyvinylalkohol-typen voll verträglich und werden'dem Schlichtebad in der angegebenen Konzentration zugegeben. Die Konzentration des beanspruchten Schlichtemittels in der Schlichteflotte beträgt üblicherweise 2 - 20 Gew.-%. Neben dem Polyvinylalkohol und dem Aminoxid können der Schlichteflotte auch andere Additive wie emulgierte Fette, Mineralöle, Stärke, Stärkeäther u.a. zugesetzt werden. Das erfindungsgemäße Schlichtemittel eignet sich hervorragend zum Schlichten von hydrophoben Synthesefasern, ins-besondere von Polyester.These amine oxides are known from DE-PS 2 326 966. They are derived from naturally occurring fatty acids, which in many cases are mixtures of products with different lengths of the alkyl chain. In addition, as is known, these natural fatty acids can also contain different amounts of unsaturated fatty acids. Accordingly, mixtures of amine oxides with different lengths of the alkyl group are also suitable according to the invention, it also being possible for these groups to be unsaturated. The amine oxides are fully compatible with the types of polyvinyl alcohol and are added to the size bath in the specified concentration. The concentration of the claimed sizing agent in the sizing liquor is usually 2 to 20% by weight. In addition to polyvinyl alcohol and amine oxide, the sizing liquor can also contain other additives such as emulsified fats, mineral oils, starch, starch ether, etc. be added. The sizing agent according to the invention is outstandingly suitable for sizing hydrophobic synthetic fibers, in particular polyester.

Nach dem Trocknen erhält man durch den Zusatz der Aminoxide klare Schlichtefilme hoher Flexibilität. Die Aminoxide schwitzen nicht aus den getrockneten Filmen aus und erhöhen auch nicht deren Hygroskopizität, verstärken aber die Klebkraft der PVAl-Solichten.After drying, the addition of the amine oxides gives clear size films of high flexibility. The amine oxides do not exude from the dried films and do not increase their hygroscopicity, but they do increase the adhesive strength of the PVAl solutes.

Beispiel 1example 1

  • a) Polyvinylalkohol, Viskosität bei 85°C in 10 %iger Lösung: 5 cPa) Polyvinyl alcohol, viscosity at 85 ° C in 10% solution: 5 cP
  • b) PVAl + 2 % Kokosdimethylaminoxidb) PVAl + 2% coconut dimethylamine oxide
  • c) PVA1 + 5 % Kokosdimethylaminoxidc) PVA1 + 5% coconut dimethylamine oxide
  • d) PVA1 + 20 % Sojalkyldiglykol-aminoxidd) PVA1 + 20% soy alkyl diglycol amine oxide

Aus dem Polyvinylalkohol a) bzw. den Mischungen b) - d) wurden Filme gegossen und 2 Stunden bei 60°C getempert. Danach wurden die Filme wie folgt beurteilt.

Figure imgb0002
Films were cast from the polyvinyl alcohol a) or the mixtures b) - d) and annealed at 60 ° C. for 2 hours. The films were then evaluated as follows.
Figure imgb0002

Der Fadenschluß wurde bestimmt nach Melliand-Textilberichte 58 (1977), S. 187 - 194. Die Pendelhärte wurde mit einem Härteprüfgerät gemessen, wobei die obigen Zahlen die Anzahl der Schwingungen angibt, die das Pendel bis zum Stillstand ausführt. Der erfindungsgemäße Zusatz eines Aminoxids.bewirkt eine Erhöhung der Flexibilität der Schlichtefilme, wobei deren Wasseraufnahme kaum steigt. Die Pendelhärte als Maß für die Sprödigkeit geht ebenfalls zurück, während der Fadenschluß als entscheidendes Kriterium für die Klebkraft ansteigt.The thread closure was determined according to Melliand-Textilberichte 58 (1977), pp. 187-194. The pendulum hardness was measured with a hardness tester, the numbers above indicating the number of vibrations that the pendulum executes until it stops. The addition of an amine oxide according to the invention brings about an increase in the flexibility of the size films, the water absorption of which hardly increases. The pendulum hardness as a measure of brittleness also decreases, while the thread closure increases as a decisive criterion for the adhesive strength.

Beispiel 2Example 2

Ein texturiertes Polyester-Filamentgarn (dtex 167 f 32) wird an einer Schlichtemaschine mit folgenden Produkten beaufschlagt:

  • a) PVA1 analog Beispiel 1
  • b) PVA1 analog Beispiel 1, enthaltend 10 % Laurylhexaglykolaminoxid
  • c) wie a + Behenyldiethylaminoxid (10 %)
  • d) wie a + Hexyldibutylaminoxid (10 %)
A textured polyester filament yarn (dtex 167 f 32) is treated with the following products on a sizing machine:
  • a) PVA1 analogous to example 1
  • b) PVA1 analogous to Example 1, containing 10% laurylhexaglycolamine oxide
  • c) as a + behenyldiethylamine oxide (10%)
  • d) as a + hexyldibutylamine oxide (10%)

Die Flotten enthalten ca. 4 % der Produkte a) - d) und werden mit 200 % Flottenaufnahme beaufschlagt. Nach dem Trocknen bei ca. 150°C (Zylindertrocknungsmaschinen) enthalten die Ketten ca. 8 % an Feststoff. Beim Abweben zeigt die Kette a erhöhte Fadenbruchzahlen, während die'Ketten b bis d zufriedenstellend sich verweben lassen.The fleets contain approx. 4% of the products a) - d) and are loaded with 200% of the fleet. After drying at approx. 150 ° C (cylinder drying machines), the chains contain approx. 8% solids. When Abweben the chain showing a higher thread break numbers, while the 'b chains can be interwoven to d satisfactory.

Claims (2)

1. Schlichtemittel bestehend aus einem Polyvinylalkohol und 1 bis 30, vorzugsweise 5 bis 15 Gew.-%, bezogen auf den Polyvinylalkohol, eines Aminoxids der Formel
Figure imgb0003
wobei R1 C5-C22-Alkyl, R2 C1-C22-Alkyl oder eine Gruppe der Formel -(CH2CH2O)nH, n eine Zahl von 1 bis 5 und R3 C1-C5-Alkyl ist oder R3 ist eine Gruppe der Formel -(CH 2CH20)mH, wenn R2 für eine Alkylgruppe mit mehr als 5 C-Atomen steht und m ist eine Zahl von 1 bis 10, wobei die Summe von n + m nicht größer als 10 ist.1. sizing agent consisting of a polyvinyl alcohol and 1 to 30, preferably 5 to 15 wt .-%, based on the polyvinyl alcohol, of an amine oxide of the formula
Figure imgb0003
 where R 1 is C 5 -C 22 alkyl, R 2 C 1 -C 22 alkyl or a group of the formula - (CH 2 CH 2 O) n H, n is a number from 1 to 5 and R 3 C 1 -C 5 -alkyl or R 3 is a group of the formula - (C H 2 CH 2 0) m H when R 2 is an alkyl group with more than 5 C atoms and m is a number from 1 to 10, the Sum of n + m is not greater than 10. 2. Schlichteflotte enthaltend 2 bis 20 Gew.-% des Schlichtemittels nach Anspruch 1.2. sizing liquor containing 2 to 20 wt .-% of the sizing agent according to claim 1.
EP80105990A 1979-10-18 1980-10-03 Sizing agent Expired EP0027923B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2942156 1979-10-18
DE19792942156 DE2942156A1 (en) 1979-10-18 1979-10-18 SLIMING AGENT

Publications (3)

Publication Number Publication Date
EP0027923A2 true EP0027923A2 (en) 1981-05-06
EP0027923A3 EP0027923A3 (en) 1982-03-17
EP0027923B1 EP0027923B1 (en) 1984-03-14

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EP80105990A Expired EP0027923B1 (en) 1979-10-18 1980-10-03 Sizing agent

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US (1) US4309510A (en)
EP (1) EP0027923B1 (en)
JP (1) JPS5663076A (en)
DE (2) DE2942156A1 (en)

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DE3028016A1 (en) 1980-07-24 1982-02-25 Hoechst Ag, 6000 Frankfurt PREPARATION AGENTS FOR SYNTHESIS FIBERS AND THE USE THEREOF
US4530876A (en) * 1983-08-12 1985-07-23 Ppg Industries, Inc. Warp sizing composition, sized warp strands and process
US4797127A (en) * 1985-10-09 1989-01-10 Air Products And Chemicals, Inc. Low foaming, high weaving efficiency polyvinyl alcohol size composition
US4845140A (en) * 1986-07-07 1989-07-04 Air Products And Chemicals, Inc. Waxless polyvinyl alcohol size composition
ATE125890T1 (en) * 1990-04-12 1995-08-15 George Bodnar METHOD FOR STABILIZING A TISSUE.
CA2106173A1 (en) * 1992-09-23 1994-03-24 Kalliopi S. Haley Fabric finish stiffening composition
US5954683A (en) * 1996-04-15 1999-09-21 Playtex Products, Inc. Composition and coating for a disposable tampon applicator and method of increasing applicator flexibility
US5804653A (en) * 1997-03-07 1998-09-08 Playtex Products, Inc. Polyvinyl alcohol compound
WO2008156454A1 (en) * 2007-06-21 2008-12-24 Kimberly-Clark Worldwide, Inc. Wiping products having enhanced oil absorbency
US8444811B2 (en) * 2005-12-15 2013-05-21 Kimberly-Clark Worldwide, Inc. Process for increasing the basis weight of sheet materials
US7883604B2 (en) 2005-12-15 2011-02-08 Kimberly-Clark Worldwide, Inc. Creping process and products made therefrom
US7837831B2 (en) * 2005-12-15 2010-11-23 Kimberly-Clark Worldwide, Inc. Tissue products containing a polymer dispersion
US7842163B2 (en) * 2005-12-15 2010-11-30 Kimberly-Clark Worldwide, Inc. Embossed tissue products
US7879189B2 (en) * 2005-12-15 2011-02-01 Kimberly-Clark Worldwide, Inc. Additive compositions for treating various base sheets
US7820010B2 (en) * 2005-12-15 2010-10-26 Kimberly-Clark Worldwide, Inc. Treated tissue products having increased strength
US7879188B2 (en) * 2005-12-15 2011-02-01 Kimberly-Clark Worldwide, Inc. Additive compositions for treating various base sheets
US7807023B2 (en) * 2005-12-15 2010-10-05 Kimberly-Clark Worldwide, Inc. Process for increasing the basis weight of sheet materials
US7879191B2 (en) * 2005-12-15 2011-02-01 Kimberly-Clark Worldwide, Inc. Wiping products having enhanced cleaning abilities
US20070137811A1 (en) * 2005-12-15 2007-06-21 Kimberly-Clark Worldwide, Inc. Premoistened tissue products
US7785443B2 (en) 2006-12-07 2010-08-31 Kimberly-Clark Worldwide, Inc. Process for producing tissue products
US20080230196A1 (en) * 2007-03-22 2008-09-25 Kou-Chang Liu Softening compositions for treating tissues which retain high rate of absorbency
US7588662B2 (en) 2007-03-22 2009-09-15 Kimberly-Clark Worldwide, Inc. Tissue products containing non-fibrous polymeric surface structures and a topically-applied softening composition
US8105463B2 (en) 2009-03-20 2012-01-31 Kimberly-Clark Worldwide, Inc. Creped tissue sheets treated with an additive composition according to a pattern

Citations (4)

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GB1087414A (en) * 1963-06-25 1967-10-18 Marchon Products Ltd Improvements in or relating to amine oxides as surfaceactive agents
GB1159984A (en) * 1965-08-19 1969-07-30 Monsanto Co Polymer Complexes
DE2326966B2 (en) * 1973-05-26 1976-07-29 Hoechst Ag, 6000 Frankfurt PREPARATION AGENT FOR SYNTHESIS FIBERS
DE2917276A1 (en) * 1978-05-01 1979-11-15 Du Pont Easily removed dressing for warp yarn, esp. polyester - contg. PVA, quat. ammonium surfactant and softener

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GB1087414A (en) * 1963-06-25 1967-10-18 Marchon Products Ltd Improvements in or relating to amine oxides as surfaceactive agents
GB1159984A (en) * 1965-08-19 1969-07-30 Monsanto Co Polymer Complexes
DE2326966B2 (en) * 1973-05-26 1976-07-29 Hoechst Ag, 6000 Frankfurt PREPARATION AGENT FOR SYNTHESIS FIBERS
DE2917276A1 (en) * 1978-05-01 1979-11-15 Du Pont Easily removed dressing for warp yarn, esp. polyester - contg. PVA, quat. ammonium surfactant and softener

Also Published As

Publication number Publication date
EP0027923B1 (en) 1984-03-14
US4309510A (en) 1982-01-05
JPS5663076A (en) 1981-05-29
DE3067009D1 (en) 1984-04-19
EP0027923A3 (en) 1982-03-17
DE2942156A1 (en) 1981-04-30

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