US20070203272A1 - Wax composition and its use - Google Patents

Wax composition and its use Download PDF

Info

Publication number
US20070203272A1
US20070203272A1 US11/711,229 US71122907A US2007203272A1 US 20070203272 A1 US20070203272 A1 US 20070203272A1 US 71122907 A US71122907 A US 71122907A US 2007203272 A1 US2007203272 A1 US 2007203272A1
Authority
US
United States
Prior art keywords
wax
amide
weight
composition
wax composition
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
Application number
US11/711,229
Other languages
English (en)
Inventor
Franz-Leo Heinrichs
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.)
Clariant Finance BVI Ltd
Original Assignee
Clariant International Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Clariant International Ltd filed Critical Clariant International Ltd
Publication of US20070203272A1 publication Critical patent/US20070203272A1/en
Assigned to CLARIANT INTERNATIONAL, LTD. reassignment CLARIANT INTERNATIONAL, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEINRICHS, FRANZ-LEO
Assigned to CLARIANT FINANCE (BVI) LIMITED reassignment CLARIANT FINANCE (BVI) LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CLARIANT INTERNATIONAL LTD.
Priority to US12/693,532 priority Critical patent/US8147606B2/en
Abandoned legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/20Carboxylic acid amides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C5/00Candles
    • C11C5/002Ingredients
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00Specific properties of additives
    • C08K2201/014Additives containing two or more different additives of the same subgroup in C08K

Definitions

  • the invention relates to a wax composition composed of at least three components and to its use as additive in plastics processing, as matting agent, as rheological agent, as slip additive, or for the preparation of dispersions.
  • the components present in the wax composition have been selected from the amide waxes group.
  • plastics such as PVC or styrene
  • engineering thermoplastics such as polyamide, polycarbonate, polyalkylene terephthalate, polyoxymethylene, polyphenylene oxide, or thermoplastic polyurethane are widely processed by the injection-molding technique. Process optimization therefore places particular importance on what is known as mold-release behavior and flow behavior of the relevant plastics. Small amounts of external processing aids are added to the plastics in order to adjust these features. Important factors with these processing aids are both their internal action and their external action.
  • fatty acids are excellent processing aids, they promote polymer degradation and at the, often high, processing temperatures reached by plastics during injection molding they are volatile and escape in the form of fume. Soaps can easily decompose in the presence of acidic constituents and then behave in exactly the same way as fatty acids.
  • Fatty acid esters are often excessively polar and in polar plastics exhibit only internal action, whereas in nonpolar plastics a marked tendency toward migration is observed.
  • the behavior of the amides of stearic acid, erucic acid, or oleic acid is similar to that of the fatty acid esters.
  • the preferred trend is therefore in the direction of longer-chain compounds, for example those derivable from montan wax acid and from its derivatives, or toward reaction products of long-chain fatty acids with diamines.
  • the prior art uses reaction products of stearic acid or of palmitic acid with ethylenediamine.
  • the ideal balance has not yet been found between internal action and external action.
  • amide waxes is intended to be defined as a collective term for a product group which is the result of reaction of a long-chain carboxylic acid with a mono- or polyfunctional amine or with ammonia.
  • the invention achieves the object via a wax composition of the type mentioned at the outset which comprises a combination composed of at least three amide waxes A, B, and C, and the characterizing feature of which is that
  • Reaction products of ethylenediamine and stearic acid or palmitic acid, olamide, erucaamide, stearylamide are available industrially.
  • inventive wax composition composed of the amide waxes A, B, and C, these being surprisingly suitable as processing aids during the injection molding of plastics with optimized internal and external action, in contrast, suitable amounts of three different components A, B, and C are combined with one another.
  • Amide wax A is reaction products of alkylenediamine, preferably of ethylenediamine, with linear fatty acids or mixtures of fatty acids, for example tallow fatty acid, coconut fatty acid, stearic acid, palmitic acid, behenic acid, or erucic acid, having the structure
  • n from 6 to 20.
  • Amide wax B is the reaction product of alkylenediamine, preferably of ethylenediamine, with 12-hydroxystearic acid, preferably having the following composition:
  • Amide wax C is the reaction product of alkylenediamine, preferably of ethylenediamine, with 12-hydroxystearic acid and with linear fatty acids, preferably having the structure:
  • n from 6 to 20.
  • the inventive wax composition preferably comprises an amount in the range from 1 to 85% by weight of amide wax A, an amount in the range from 1 to 85% by weight of amide wax B, and an amount in the range from 1 to 50% by weight of amide wax C, based in each case on the total weight of the wax composition.
  • the wax composition comprises an amount in the range from 5 to 75% by weight of amide wax A, an amount in the range from 5 to 75% by weight of amide wax B, and an amount in the range from 1 to 40% by weight of amide wax C, again based in each case on the total weight of the wax composition.
  • the reaction of the starting materials with alkylenediamine, preferably with ethylenediamine, for preparation of the amide waxes takes place at temperatures above 100° C.
  • the fatty acid mixtures are placed in a reactor where they are melted under an inert gas.
  • ethylenediamine is metered, with stirring, into the resultant melt.
  • the temperature is further increased to 190° C., and stirring is continued, with removal of the water of reaction by distillation, until both the acid number AcN and the alkali number AIN have fallen below the value 6.
  • the acid number AcN is determined to DIN EN ISO 3682 to monitor the progress of the reaction, the alkali number AIN being determined to DGF method H III 2a (92).
  • inventive wax compositions are then prepared from the amide waxes A, B, and C of the preparation examples via mixing.
  • the precise composition of the wax compositions is analyzed by gas chromatography.
  • inventive wax compositions comprising at least the amide waxes A, B, and C have particular suitability as processing aids for the injection molding of conventional plastics, such as PVC or styrene, or of engineering thermoplastics, such as polyamide, polycarbonate, polyalkylene terephthalate, polyoxymethylene, polyphenylene oxide, or for thermoplastic polyurethane.
  • the amounts of the wax composition inventively added as processing aid to the plastics are in the range from 0.1 to 10% by weight, preferably from 0.2 to 5% by weight, particularly preferably from 0.2 to 2% by weight, based in each case on the total weight of plastic plus processing aid.
  • inventive wax compositions can be employed as pure substances or can be mixed with known prior-art mixture components, such as polyethylene waxes, polypropylene waxes, amide waxes, Fischer-Tropsch waxes, and then can be micronized.
  • the particle size here is advantageously adjusted within the range from 10 to 20 ⁇ m.
  • inventive wax compositions can moreover also be dissolved in solvents at an elevated temperature and be precipitated via cooling. Pastes thus prepared can be used in print applications for control of viscosity and of slip behavior.
  • the wax compositions are then prepared from the amide waxes A, B, and C of preparation examples 1 to 5.
  • the exact composition of the inventive wax compositions is analyzed by means of GC.
  • the composition by weight of the inventive wax compositions WC 1 to WC 4 and of the comparative mixture c 1 and c 2 of the prior art have been listed in the table below. These were then tested as processing aid in engineering plastics and in micronized form as additives in the coating.
  • thermoplastic polyurethane (TPU) An amount of 0.4% by weight of the wax compositions, based on the weight of the mixture composed of esterdiol and wax composition, was inserted into the esterdiol component during the preparation of thermoplastic polyurethane (TPU).
  • inventive products comprising wax compositions WC 1 to WC 4 , the mixture 1 , and pure EBS c 2 , and also on a commercially available derivative of montan wax acid.
  • inventive products can significantly improve migration behavior at an adequate level of demolding force.
  • c 1 is Hostalub FA 1
  • c 3 is Hostalub FA 5.
  • the experiments showed that the inventive wax compositions improved flow behavior and migration behavior at identical demolding force.
  • the inventive products remain within the matrix and do not exude even when the amounts added are relatively high.
  • inventive mixtures were also tested in PVC against standard amide waxes and montan wax derivatives.
  • test formulation 100 parts of Vinnolit S 3160, PVC from Vinnolit, 1.5 parts of Mark 17 MOK, 5 parts of Kane ABE-58A, 1 part of Paraloid K 120 N, 0.3 part of Loxiol G 16, 0.4 part of test product or comparative product.
  • c 1 Hostalub FA1 amide wax
  • c 3 Hostalub FA 5 amide wax
  • the behavior of the inventive products was the same as that of the standard in terms of release action and lubricant action, and when compared with the prior-art products they were poorer in terms of color but better in terms of exudation behavior.
  • Action was tested in a test formulation composed of 100 parts of Makrolon 3108, 0.5 part of wax composition/comparative product.
  • the mixtures WC 1 and WC 2 were tested against Licolub FA1 and Licolub FA 5. Color, transparency, release action and melt index were tested.
  • the table shows that the inventive wax compositions have good compatibility with polycarbonate and remain within the matrix even when the amounts added are relatively high. In terms of external action, no increase occurs in demolding force.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
US11/711,229 2006-02-28 2007-02-27 Wax composition and its use Abandoned US20070203272A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/693,532 US8147606B2 (en) 2006-02-28 2010-01-26 Wax compositions and its use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006009097.7 2006-02-28
DE102006009097A DE102006009097A1 (de) 2006-02-28 2006-02-28 Wachszusammensetzung und deren Verwendung

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/693,532 Division US8147606B2 (en) 2006-02-28 2010-01-26 Wax compositions and its use

Publications (1)

Publication Number Publication Date
US20070203272A1 true US20070203272A1 (en) 2007-08-30

Family

ID=38001721

Family Applications (2)

Application Number Title Priority Date Filing Date
US11/711,229 Abandoned US20070203272A1 (en) 2006-02-28 2007-02-27 Wax composition and its use
US12/693,532 Active US8147606B2 (en) 2006-02-28 2010-01-26 Wax compositions and its use

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/693,532 Active US8147606B2 (en) 2006-02-28 2010-01-26 Wax compositions and its use

Country Status (5)

Country Link
US (2) US20070203272A1 (es)
EP (1) EP1826235B1 (es)
JP (1) JP5455288B2 (es)
DE (2) DE102006009097A1 (es)
ES (1) ES2330264T3 (es)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110146537A1 (en) * 2009-12-18 2011-06-23 Xerox Corporation Low molecular weight pigment dispersants for phase change ink
US20110151123A1 (en) * 2009-12-18 2011-06-23 Xerox Corporation Pigmented Phase Change Inks Containing Low Molecular Weight Pigment Dispersants
US8329854B2 (en) 2010-09-27 2012-12-11 Xerox Corporation Synthesis of tri-component resins
US8367751B2 (en) 2010-09-27 2013-02-05 Xerox Corporation Tri-component resins for pigmented ink
US20160017178A1 (en) * 2013-03-15 2016-01-21 Clariant International Ltd. Cellulose-Containing Paint Systems

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006009096B4 (de) * 2006-02-28 2009-06-10 Bayer Materialscience Ag Thermoplastisch verarbeitbare Polyurethane, Verfahren zu ihrer Herstellung und ihre Verwendung
DE102012112637A1 (de) 2012-12-19 2014-06-26 Contitech Antriebssysteme Gmbh Elastischer Artikel, insbesondere Antriebsriemen
CN103060713B (zh) * 2013-01-22 2015-07-08 中国石油天然气集团公司 一种高钢级抗硫钻杆材料及其制备方法
KR102279328B1 (ko) * 2016-09-13 2021-07-21 도레이 카부시키가이샤 중공 성형품 및 중공 성형품의 제조 방법
US10351798B2 (en) 2017-01-20 2019-07-16 Iowa State University Research Foundation, Inc. Fatty acid ester-based wax compositions and methods of making thereof
US10851046B2 (en) 2017-03-22 2020-12-01 Iowa State University Research Foundation, Inc. Vegetable oil-based material as a substitute for carnauba wax
CN115873304B (zh) * 2022-12-16 2024-03-19 青岛赛诺新材料有限公司 润滑分散助剂复合ebs、制备方法及其应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5810919A (en) * 1997-10-30 1998-09-22 Alliedsignal Inc. High temperature protective wax blend
US5936018A (en) * 1996-11-28 1999-08-10 Bayer Aktiengesellschaft Melt-processable polyurethanes containing special wax mixtures
US6761764B2 (en) * 2000-05-12 2004-07-13 Clariant Gmbh Use of wax mixtures for coatings
US20060041101A1 (en) * 2002-06-05 2006-02-23 Franz-Leo Heinrichs Conversion products of mixtures of long-chained fatty acids and aliphatic diamines, and the use thereof

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR998053A (fr) 1949-09-28 1952-01-14 Standard Francaise Petroles Amélioration de la stabilité à la chaleur des propriétés adhésives des liants hydrocarbones
JPS5229293B2 (es) * 1971-08-06 1977-08-01
JPH03152148A (ja) * 1989-11-07 1991-06-28 Sekisui Chem Co Ltd 押出成形用硬質塩素化塩化ビニル樹脂組成物
DE19546073A1 (de) * 1995-12-11 1997-06-12 Hoechst Ag Stabile wäßrige Wachsdispersionen
AU4829300A (en) 1999-05-10 2000-11-21 Goldschmidt Chemical Company Road repair methods and fast breaking asphalt emulsion compositions useful therewith
DE19942962B4 (de) * 1999-09-09 2004-12-23 Clariant Gmbh Wachsmischung für wäßrige Anwendungen
WO2005003230A1 (ja) * 2003-07-08 2005-01-13 Kaneka Corporation 硬化性組成物
JP2006131882A (ja) * 2004-10-06 2006-05-25 Unitika Ltd 水性分散体、塗膜および積層体
DE102006009096B4 (de) * 2006-02-28 2009-06-10 Bayer Materialscience Ag Thermoplastisch verarbeitbare Polyurethane, Verfahren zu ihrer Herstellung und ihre Verwendung

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5936018A (en) * 1996-11-28 1999-08-10 Bayer Aktiengesellschaft Melt-processable polyurethanes containing special wax mixtures
US5810919A (en) * 1997-10-30 1998-09-22 Alliedsignal Inc. High temperature protective wax blend
US6761764B2 (en) * 2000-05-12 2004-07-13 Clariant Gmbh Use of wax mixtures for coatings
US20060041101A1 (en) * 2002-06-05 2006-02-23 Franz-Leo Heinrichs Conversion products of mixtures of long-chained fatty acids and aliphatic diamines, and the use thereof

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110146537A1 (en) * 2009-12-18 2011-06-23 Xerox Corporation Low molecular weight pigment dispersants for phase change ink
US20110151123A1 (en) * 2009-12-18 2011-06-23 Xerox Corporation Pigmented Phase Change Inks Containing Low Molecular Weight Pigment Dispersants
US7973186B1 (en) 2009-12-18 2011-07-05 Xerox Corporation Low molecular weight pigment dispersants for phase change ink
US8507041B2 (en) 2009-12-18 2013-08-13 Xerox Corporation Pigmented phase change inks containing low molecular weight pigment dispersants
US8329854B2 (en) 2010-09-27 2012-12-11 Xerox Corporation Synthesis of tri-component resins
US8367751B2 (en) 2010-09-27 2013-02-05 Xerox Corporation Tri-component resins for pigmented ink
US20160017178A1 (en) * 2013-03-15 2016-01-21 Clariant International Ltd. Cellulose-Containing Paint Systems

Also Published As

Publication number Publication date
US20100126385A1 (en) 2010-05-27
EP1826235A1 (de) 2007-08-29
US8147606B2 (en) 2012-04-03
DE502007001209D1 (de) 2009-09-17
EP1826235B1 (de) 2009-08-05
DE102006009097A1 (de) 2007-08-30
ES2330264T3 (es) 2009-12-07
JP2007231273A (ja) 2007-09-13
JP5455288B2 (ja) 2014-03-26

Similar Documents

Publication Publication Date Title
US8147606B2 (en) Wax compositions and its use
EP1327660B1 (de) Stabilisatorkombinationen für chlorhaltige Polymere
US12076888B2 (en) Stabilized compositions and process for producing same
EP0792317B1 (en) Liquid pvc stabilizers and lubricants
DE69126479T2 (de) Methode und Zusammensetzung zur Verbesserung der Verarbeitbarkeit von Kautschuk und Kunststoffen
US20050006627A1 (en) Sterically hindered phenol antioxidant granules having balanced hardness
EP2545116B1 (de) Stabilisatormischungen für halogenhaltige kunststoffe durch unterwassergranulierung
MX2012015012A (es) Concentrado aditivo para polimeros.
JP4952248B2 (ja) 熱可塑性樹脂組成物
EP2714799A2 (en) Thermoplastic elastomers moldable under low shear conditions
DE10351820B4 (de) PVC-Formmassen mit verbesserter Verarbeitbarkeit
JPH07304967A (ja) 熱可塑性樹脂組成物
DE10060819A1 (de) Verwendung von Polyetheramin-Derivaten zur dauerhaften Verbesserung der Klebstoff- und/oder Beschichtungs-Kompatibilität von Polyethylen-basierten Formkörpern, Fasern und Folien
US11518881B2 (en) Polysiloxanes in thermoplastic elastomer compounds for overmolded thermoplastic articles
KR920005544B1 (ko) 열가소성 수지용 고농축 이형제(Master Batch)와 그 제조방법
KR100314706B1 (ko) 자동차 내장재용 열가소성 수지 조성물
EP1209188B1 (de) Verfahren zur Herstellung von Polypropylen-basierten Formkörpern, Fasern und Folien
US20230357471A1 (en) High molecular weight acrylic processing aid concentrate for thermoplastic processing
DE10060818A1 (de) Verwendung von Polyetheraminen zur dauerhaften Verbesserung der Klebstoff- und/oder Beschichtungs-Kompatibilität von Polyethylen-basierten Formkörpern, Fasern und Folien
EP1641872A1 (de) Verwendung von zusammensetzungen auf basis von zinksalzen aromatischer und nichtaromatischer carbons uren zur stabilisierung von halogenhaltigen organischen kunststoffen
JP2004168056A5 (es)
JPH10204502A (ja) 無機物粉末射出成形用組成物および焼結体

Legal Events

Date Code Title Description
AS Assignment

Owner name: CLARIANT INTERNATIONAL, LTD., SWITZERLAND

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HEINRICHS, FRANZ-LEO;REEL/FRAME:023037/0733

Effective date: 20070308

AS Assignment

Owner name: CLARIANT FINANCE (BVI) LIMITED, VIRGIN ISLANDS, BR

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CLARIANT INTERNATIONAL LTD.;REEL/FRAME:023357/0527

Effective date: 20090929

Owner name: CLARIANT FINANCE (BVI) LIMITED,VIRGIN ISLANDS, BRI

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CLARIANT INTERNATIONAL LTD.;REEL/FRAME:023357/0527

Effective date: 20090929

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION