WO1997007158A1 - Improved waxes for actuators - Google Patents

Improved waxes for actuators Download PDF

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Publication number
WO1997007158A1
WO1997007158A1 PCT/US1996/007986 US9607986W WO9707158A1 WO 1997007158 A1 WO1997007158 A1 WO 1997007158A1 US 9607986 W US9607986 W US 9607986W WO 9707158 A1 WO9707158 A1 WO 9707158A1
Authority
WO
WIPO (PCT)
Prior art keywords
tert
wax
composition
butyl
pentaerythritol diphosphite
Prior art date
Application number
PCT/US1996/007986
Other languages
French (fr)
Inventor
Joseph D. Menczel
Barbara J. Long
James B. Stamatoff
David Rademacher
M. Ishaq Haider
Original Assignee
Hoechst Celanese Corporation
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 Hoechst Celanese Corporation filed Critical Hoechst Celanese Corporation
Publication of WO1997007158A1 publication Critical patent/WO1997007158A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/527—Cyclic esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C08L91/06—Waxes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof

Definitions

  • This invention relates to the field of thermally expandable materials for actuators, especially to thermally expandable wax compositions containing one or more additives to increase thermooxidative stability, increase viscosity, and/or decrease hardness of the composition.
  • thermally expandable material Actuators that use a thermally expandable material are well-known in the art.
  • a commonly used thermally expandable material is a type of wax, although plastics and metals have also been employed in actuators and similar devices that use thermally expandable materials.
  • Waxes have the advantage of a low melting point, so that the large expansion that occurs when the solid melts into liquid occurs at relatively low operating temperatures.
  • the stability of a wax composition e.g. resistance to oxidation and thermal breakdown, and the viscosity and hardness of the composition are significant factors in the performance of a wax composition in an actuator.
  • thermooxidative stability is very desirable.
  • Increased viscosity is highly desirable where additives are used, e.g., relatively dense metal powders added to increase thermal conductivity may tend to settle in a low viscosity medium.
  • decreased hardness is desirable to avoid the formation of hard plugs in the actuator.
  • wax refers to a substance that is a plastic solid at room temperature and melts at a relatively moderate temperature to form a relatively low viscosity liquid.
  • Waxes are generally contain a complex combination of organic compounds, especially long-chained organic acids, esters and hydrocarbons. Waxes include beeswax, waxes taken from plants (e.g., carnauba wax, bayberry wax, and the like), and mineral waxes derived from petroleum or coal. Montan wax is an example of the latter, being derived by solvent extraction of lignite. Paraffin is a well- known type of petroleum wax, obtained by crude oil distillation/separation.
  • Low molecular weight hydrocarbon polymers also form waxes, especially polyethylene and polypropylene waxes; these waxes may be made by polymerization or obtained by thermally degrading higher molecular weight polymers. Unlike other waxes, these polymers tend to contain molecules that are of the same type, although as in all waxes the molecular weights of the molecules vary.
  • composition of any type of wax varies based on the origin of the wax and the treatment it has undergone.
  • Waxes of the same type may vary in purity, color, melting point, hardness, and other properties and characteristics.
  • U.S. Patent Number 3,194,009 issued to Baker discloses thermal actuators having a composition prepared from a molten wax and a liquid monomer of elastomeric material, which composition is vulcanized or cured to a dry semi-solid elastomeric material.
  • the present invention is a thermally expandable wax composition for use in actuators comprising a wax and a thermooxidative stabilizer.
  • stabilizers include tetrakis(3,5-di-tert-butyl-4-hydroxycinnamate)) methane, calcium bis (monethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate), bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, diestearyl pentaerythritol diphosphite, and similar compounds, and combinations thereof.
  • the composition may also include a viscosity enhancer, e.g.
  • the stabilizer typically comprises about 0.1 - 2.0% by weight of the total composition, preferably about 0.1 - 0.5%.
  • a polyethylene wax e.g., PE-190 polyethylene wax available from Hoechst
  • each stabilizer comprises about 0.5% by weight of the wax composition.
  • the calcium bis (monethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate) may be replaced by 0.5% diestearyl pentaerythritol diphosphite.
  • an oxidized polyethylene wax or a Montan wax e.g., PED-521 oxidized polyethylene wax or Montan wax E, both available from Hoechst A.G. of
  • each stabilizer comprises about 0.1 - 0.5% by weight of each wax composition.
  • the calcium bis (monethyl (3, 5-di- tert-butyl-4-hydroxybenzyl) phosphonate) may be replaced by 0.1 - 0.5% diestearyl pentaerythritol diphosphite in each composition.
  • a polypropylene wax e.g., Hoechst A.G.'s PP-230 polypropylene wax
  • tetrakis methylene (3,5-di-tert-butyl-4-hydroxycinnamate)
  • methane e.g., 1,3-di-tert-butyl-4-hydroxycinnamate
  • each stabilizer comprises about 0.1 - 0.5% by weight of the wax composition.
  • the bis(2,4-di-tert-butyl ⁇ henyl) pentaerythritol diphosphite may be replaced by 0.1 - 0.5% diestearyl pentaerythritol diphosphite.
  • thermooxidative stabilizers To test the effectiveness of the thermooxidative stabilizers, four different waxes were tested, both with stabilizers according to the present invention and without stabilizers (control). The tests consisted of measuring weight loss for wax compositions held at 200EC or 225EC for one hour, both in a nitrogen atmosphere and in air. The weight loss in the nitrogen atmosphere is believed to be the result of evaporation of the more volatile components of the composition, whereas the weight loss in air includes the evaporation of additional volatile species that are generated by the oxidative degradation of the wax.
  • stabilizer A is tetrakis (methylene (3,5-di-tert- butyl-4-hydroxycinnamate)) methane
  • stabilizer B is calcium bis (monethyl
  • stabilizer C is bis(2,4-di- tert-butylphenyl) pentaerythritol diphosphite; and the waxes are identified by the Hoechst A.G. names introduced above. Table 1
  • Wax Stabilizers EC Wt loss in Wt loss in air N 2
  • the data in table 1 shows that weight loss in a non-oxidative environment, i.e. nitrogen, is not affected much by the presence of the stabilizers, but that in an oxidative environment, i.e. air, these waxes suffer a much greater weight loss without the stabilizers.
  • the stabilized wax compositions according to the present invention had dramatically reduced weight losses in air; in most cases, the weight losses were reduced almost to the level of the weight losses in the non-oxidative environment.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A thermally expandable wax composition for use in actuators having a high stability toward thermooxidative decomposition. This composition contains a wax and a thermooxidative stabilizer. Examples of such stabilizers include tetrakis(methylene(3,5-di-tert-butyl-4-hydroxycinnamate)) methane, calcium bis(monethyl(3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate), bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, and diestearyl pentaerythritol diphosphite, and combinations thereof. Optionally, the composition may also include a viscosity enhancer, e.g. ethylene-vinyl acetate copolymer, and/or an oil, e.g. paraffin oil, added to reduce hardness.

Description

IMPROVED WAXES FOR ACTUATORS
Background Of The Invention
This invention relates to the field of thermally expandable materials for actuators, especially to thermally expandable wax compositions containing one or more additives to increase thermooxidative stability, increase viscosity, and/or decrease hardness of the composition.
Actuators that use a thermally expandable material are well-known in the art. A commonly used thermally expandable material is a type of wax, although plastics and metals have also been employed in actuators and similar devices that use thermally expandable materials. Waxes have the advantage of a low melting point, so that the large expansion that occurs when the solid melts into liquid occurs at relatively low operating temperatures.
The stability of a wax composition, e.g. resistance to oxidation and thermal breakdown, and the viscosity and hardness of the composition are significant factors in the performance of a wax composition in an actuator.
Repetitive heating and cooling cycles in an oxidative environment are a typical part of most actuator performance; for this reason, thermooxidative stability is very desirable. Increased viscosity is highly desirable where additives are used, e.g., relatively dense metal powders added to increase thermal conductivity may tend to settle in a low viscosity medium. Furthermore, decreased hardness is desirable to avoid the formation of hard plugs in the actuator.
The term wax refers to a substance that is a plastic solid at room temperature and melts at a relatively moderate temperature to form a relatively low viscosity liquid. Waxes are generally contain a complex combination of organic compounds, especially long-chained organic acids, esters and hydrocarbons. Waxes include beeswax, waxes taken from plants (e.g., carnauba wax, bayberry wax, and the like), and mineral waxes derived from petroleum or coal. Montan wax is an example of the latter, being derived by solvent extraction of lignite. Paraffin is a well- known type of petroleum wax, obtained by crude oil distillation/separation. Low molecular weight (about 10,000 g/mole or less) hydrocarbon polymers also form waxes, especially polyethylene and polypropylene waxes; these waxes may be made by polymerization or obtained by thermally degrading higher molecular weight polymers. Unlike other waxes, these polymers tend to contain molecules that are of the same type, although as in all waxes the molecular weights of the molecules vary.
The exact composition of any type of wax varies based on the origin of the wax and the treatment it has undergone. Waxes of the same type may vary in purity, color, melting point, hardness, and other properties and characteristics.
U.S. Patent Number 3,194,009 issued to Baker discloses thermal actuators having a composition prepared from a molten wax and a liquid monomer of elastomeric material, which composition is vulcanized or cured to a dry semi-solid elastomeric material.
Summary Of The Invention
The present invention is a thermally expandable wax composition for use in actuators comprising a wax and a thermooxidative stabilizer. Such stabilizers include tetrakis(3,5-di-tert-butyl-4-hydroxycinnamate)) methane, calcium bis (monethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate), bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, diestearyl pentaerythritol diphosphite, and similar compounds, and combinations thereof. Optionally, the composition may also include a viscosity enhancer, e.g. ethylene-vinyl acetate copolymer, and/or an oil, e.g. paraffin oil, added to reduce hardness. The stabilizer typically comprises about 0.1 - 2.0% by weight of the total composition, preferably about 0.1 - 0.5%.
It is an object of the present invention to provide a wax composition having improved resistance to thermooxidative decomposition.
It is another object of the present invention to provide a wax composition having increased viscosity and decreased hardness.
Other objects and advantages of the present invention will be apparent to those skilled in the art from the following description and the appended claims.
Detailed Description Of The Preferred Embodiments
In one preferred embodiment of the present invention, a polyethylene wax (e.g., PE-190 polyethylene wax available from Hoechst
A.G. of Germany) is blended with tetrakis (methylene (3,5-di-tert-butyl-4- hydroxycinnamate)) methane and calcium bis (monethyl (3,5-di-tert-butyl- 4-hydroxybenzyl) phosphonate) which provide thermooxidative stability to the wax. Preferably, each stabilizer comprises about 0.5% by weight of the wax composition. In an alternate preferred embodiment, the calcium bis (monethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate) may be replaced by 0.5% diestearyl pentaerythritol diphosphite.
In other preferred embodiments of the present invention, an oxidized polyethylene wax or a Montan wax (e.g., PED-521 oxidized polyethylene wax or Montan wax E, both available from Hoechst A.G. of
Germany) is blended with tetrakis (methylene (3,5-di-tert-butyl-4- hydroxycinnamate)) methane and calcium bis (monethyl (3,5-di-tert-butyl- 4-hydroxybenzyl) phosphonate) which provide thermooxidative stability to the wax. Preferably, each stabilizer comprises about 0.1 - 0.5% by weight of each wax composition. Alternatively, the calcium bis (monethyl (3, 5-di- tert-butyl-4-hydroxybenzyl) phosphonate) may be replaced by 0.1 - 0.5% diestearyl pentaerythritol diphosphite in each composition.
In another preferred embodiment, a polypropylene wax (e.g., Hoechst A.G.'s PP-230 polypropylene wax) is blended with tetrakis (methylene (3,5-di-tert-butyl-4-hydroxycinnamate)) methane and bis(2,4- di-tert-butylphenyl) pentaerythritol diphosphite. Preferably, each stabilizer comprises about 0.1 - 0.5% by weight of the wax composition. Alternatively, the bis(2,4-di-tert-butylρhenyl) pentaerythritol diphosphite may be replaced by 0.1 - 0.5% diestearyl pentaerythritol diphosphite. The following Examples are presented to illustrate the present invention, but should not be construed as limiting the scope of this invention.
EXAMPLES
To test the effectiveness of the thermooxidative stabilizers, four different waxes were tested, both with stabilizers according to the present invention and without stabilizers (control). The tests consisted of measuring weight loss for wax compositions held at 200EC or 225EC for one hour, both in a nitrogen atmosphere and in air. The weight loss in the nitrogen atmosphere is believed to be the result of evaporation of the more volatile components of the composition, whereas the weight loss in air includes the evaporation of additional volatile species that are generated by the oxidative degradation of the wax. The results are shown in Table 1 , below, in which: stabilizer A is tetrakis (methylene (3,5-di-tert- butyl-4-hydroxycinnamate)) methane; stabilizer B is calcium bis (monethyl
(3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate); stabilizer C is bis(2,4-di- tert-butylphenyl) pentaerythritol diphosphite; and the waxes are identified by the Hoechst A.G. names introduced above. Table 1
Wax Stabilizers EC Wt loss in Wt loss in air N2
Montan Wax E None (Control) 200 7.05% 3.23% Montan Wax E 0.5% A + 0.5% B 200 3.49% 2.43%
PP-230 None (Control) 225 58.85% 2.21% PP-230 0.5% A + 0.5% C 225 2.62% 2.29%
PED-521 None (Control) 200 11.42% 3.28% PED-521 0.5% A + 0.5% B 200 7.43% 3.24%
PE-190 None (Control) 225 10.33% 0.61% PE-190 0.5% A + 0.5% B 225 0.85% 0.67%
The data in table 1 shows that weight loss in a non-oxidative environment, i.e. nitrogen, is not affected much by the presence of the stabilizers, but that in an oxidative environment, i.e. air, these waxes suffer a much greater weight loss without the stabilizers. The stabilized wax compositions according to the present invention had dramatically reduced weight losses in air; in most cases, the weight losses were reduced almost to the level of the weight losses in the non-oxidative environment. These data clearly show the effectiveness of the stabilizers in reducing the thermooxidative decomposition of these waxes.
Many variations of the present invention not illustrated herein will occur to those skilled in the art. The present invention is not limited to the embodiments illustrated and described herein, but encompasses all the subject matter within the scope of the appended claims.

Claims

Claims
1. A thermally expandable wax composition for use in actuators comprising a wax and a thermooxidative stabilizer.
2. The composition of claim 1 wherein said stabilizer is selected from the group consisting of tetrakis(3,5-di-tert-butyl-4- hydroxycinnamate)) methane, calcium bis(3,5-di-tert-butyl-4- hydroxybenzyl) phosphonate), bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, diestearyl pentaerythritol diphosphite, and combinations thereof,
3. The composition of claim 2 wherein said stabilizer comprises
0.1-2.0% by weight of the total composition.
4. The composition of claim 1 wherein said stabilizer comprises 0.1-2.0% by weight of the total composition.
5. The composition of claim 1 further comprising ethylene-vinyl acetate copolymer and 5-30% by weight paraffin oil.
6. A thermally expandable wax composition for use in actuators comprising: a wax;
0.1-2.0% by weight of a thermooxidative stabilizer selected from the group consisting of tetrakis(3,5-di-tert- butyl-4-hydroxycinnamate)) methane, calcium bis(3,5-di-tert- butyl-4-hydroxybenzyl) phosphonate), bis(2,4-di-tert- butylphenyl) pentaerythritol diphosphite, diestearyl pentaerythritol diphosphite, and combinations thereof; 5-30% by weight paraffin oil; and, ethylene-vinyl acetate copolymer.
PCT/US1996/007986 1995-08-15 1996-05-30 Improved waxes for actuators WO1997007158A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51547695A 1995-08-15 1995-08-15
US08/515,476 1995-08-15

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997031081A1 (en) * 1996-02-23 1997-08-28 Hoechst Celanese Corporation Thermally expandable, viscosity modified wax compositions and method of use in actuators
WO2010069854A2 (en) * 2008-12-19 2010-06-24 Basf Se Modified polyolefin waxes
WO2019211235A1 (en) * 2018-05-03 2019-11-07 SI Group Switzerland (Chaa) Gmbh Antidegradant blend

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB685168A (en) * 1950-01-03 1952-12-31 Standard Oil Dev Co Improvements in or relating to petroleum wax compositions
FR1330473A (en) * 1961-08-04 1963-06-21 Shell Int Research Stable gloss paraffin wax compositions
US3905782A (en) * 1973-05-14 1975-09-16 Phillips Petroleum Co Odor inhibition for paraffin hydrocarbons
EP0393518A2 (en) * 1989-04-19 1990-10-24 Hoechst Aktiengesellschaft Polyolefin moulding composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB685168A (en) * 1950-01-03 1952-12-31 Standard Oil Dev Co Improvements in or relating to petroleum wax compositions
FR1330473A (en) * 1961-08-04 1963-06-21 Shell Int Research Stable gloss paraffin wax compositions
US3905782A (en) * 1973-05-14 1975-09-16 Phillips Petroleum Co Odor inhibition for paraffin hydrocarbons
EP0393518A2 (en) * 1989-04-19 1990-10-24 Hoechst Aktiengesellschaft Polyolefin moulding composition

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997031081A1 (en) * 1996-02-23 1997-08-28 Hoechst Celanese Corporation Thermally expandable, viscosity modified wax compositions and method of use in actuators
US5772949A (en) * 1996-02-23 1998-06-30 Hoechst Celanese Corp. Thermally expandable, viscosity modified wax compositions and method of use in actuators
WO2010069854A2 (en) * 2008-12-19 2010-06-24 Basf Se Modified polyolefin waxes
WO2010069854A3 (en) * 2008-12-19 2010-09-02 Basf Se Modified polyolefin waxes
WO2019211235A1 (en) * 2018-05-03 2019-11-07 SI Group Switzerland (Chaa) Gmbh Antidegradant blend
CN112004879A (en) * 2018-05-03 2020-11-27 瑞士新集团有限公司 Antidegradant blends
US11879050B2 (en) 2018-05-03 2024-01-23 Si Group, Inc. Antidegradant blend

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