CN1273593A - Magnetic polyester compositions - Google Patents

Magnetic polyester compositions Download PDF

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Publication number
CN1273593A
CN1273593A CN 98809846 CN98809846A CN1273593A CN 1273593 A CN1273593 A CN 1273593A CN 98809846 CN98809846 CN 98809846 CN 98809846 A CN98809846 A CN 98809846A CN 1273593 A CN1273593 A CN 1273593A
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Prior art keywords
residue
phenyl
accounts
polymkeric substance
composition
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CN 98809846
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Chinese (zh)
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L·A·明尼克
T·J·皮克瑞尼
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Eastman Chemical Co
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Eastman Chemical Co
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Priority claimed from US09/160,487 external-priority patent/US5919848A/en
Application filed by Eastman Chemical Co filed Critical Eastman Chemical Co
Publication of CN1273593A publication Critical patent/CN1273593A/en
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    • 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
    • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
    • C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds

Abstract

Disclosed are magnetic polyester compositions comprising a thermoplastic polyester polymer, certain epoxy-containing ethylene polymers, an aromatic phosphite compound, and elemental or magnetite iron.

Description

Magnetic polyester compositions
Invention field
The present invention relates to certain novel magnetic polymer blend, it comprises thermoplastic polyester polymer, certain contains ethene polymers, aromatic phosphite compound and element or the magnetite iron of epoxy.
Summary of the invention
Novel thermoplastic provided by the invention, magnetic polyester compositions comprise following ingredients:
I. about 39.5～about 72.9wt% thermoplastic polyester comprises following ingredients:
(A) comprise 50mol% terephthalic acid residue's diacid residues at least; And
(B) comprise at least 50mol% by the diol residue of ethylene glycol, 1,4 cyclohexane dimethanol or its mixture deutero-residue;
II. about 2～about 10wt%1 kind or multiple general formula are the ethene polymers that contains epoxy of X/Y/Z, wherein:
X represents the ethene residue, and it accounts for about 50～95wt% of polymkeric substance X/Y/Z;
Y representative is by vinyl acetate between to for plastic or have the residue of the compound deriving of following formula:
Figure A9880984600051
R wherein 1Be the alkyl or cycloalkyl group that contains the highest about 12 carbon atoms, perhaps phenyl or alkyl phenyl group, moieties wherein contains the highest about 12 carbon atoms; R 2Be hydrogen, methyl or ethyl, preferred hydrogen; Y accounts for about 4～35 wt% of polymkeric substance E/X/Y, preferred 15～30wt%;
The Z representative is by the residue or the monomeric unit of the monomer derived that contains epoxide group that is selected from glycidyl acrylate and glycidyl methacrylate, and Z accounts for about 1～15wt% of polymkeric substance X/Y/Z, preferred about 1～10wt%;
III. about 0.1～about 0.5wt%1 kind or multiple aromatic phosphite compound; And
IV. about 25～about 50wt% is selected from Fe 3O 4The ferrous components of ferric oxide and elemental iron; And wherein polyester composition I is based on 100mol% diacid residues and 100mol% diol residue, and the weight percentage of each is that gross weight in composition I, II, III and IV is a benchmark among composition I, II, III and the IV.
Find unexpectedly, polymer blend of the present invention since for improve the magnetic adding wherein filler or the raising of iron oxide content had toughness or extension at break.This kind polymer blend can adopt extrusion method to be configured as articles of sheet material.This kind articles of sheet material can be used for requiring to make the purposes of response or generation suction in magnetic field.
Detailed Description Of The Invention
The diacid residues of polyester composition I comprises 50mol% terephthalic acid residue at least.This diacid composition can comprise the highest about 50mol%1 kind or multiple other diacid residues except that terephthalic acid, as aromatic dicarboxylic acid, preferably has 8～14 carbon atoms; Aliphatic dicarboxylic acid preferably has 4～12 carbon atoms; Or the cycloaliphatic dicarboxylic acid, preferably have 8～12 carbon atoms.The example of these dicarboxylic acid comprises phthalic acid, m-phthalic acid, naphthalene-2,6-dicarboxylic acid, cyclohexane dicarboxylic acid, cyclohexanediacetic, phenylbenzene-4,4 '-dicarboxylic acid, succsinic acid, pentanedioic acid, hexanodioic acid, nonane diacid, sebacic acid etc.Polyester composition I can be by two or more above-mentioned dicarboxylic acid preparations.The diacid residues of polyester composition I can be by dicarboxylic acid, its ester and acyl chlorides, and in some cases, the acid anhydrides of dicarboxylic acid is derived.
The diol residue of polyester composition I comprises at least 50mol% by ethylene glycol, 1,4 cyclohexane dimethanol or its mixture deutero-residue.This diol component can comprise the highest about 50mol%1 kind or multiple other diol residue, as cycloaliphatic diol, preferably has 6～20 carbon atoms; Or aliphatic diol, preferably have 3～20 carbon atoms.The example of other glycol of this kind comprises glycol ether, triglycol, propane-1, the 3-glycol, butane-1, the 4-glycol, pentane-1, the 5-glycol, hexane-1, the 6-glycol, 3-methyl pentanediol-(2,4), 2 hexylene glycol-(1,4), 2,2,4-neopentyl glycol-(1,3), 2-Rutgers 612-(1,3), 2,2-diethyl propane-1, the 3-glycol, 1, the 3-hexylene glycol, 1, two (2-hydroxyl-oxethyl) benzene of 4-, 2, two (4-hydroxy-cyclohexyl) propane of 2-, 1,1,3,3-tetramethyl--2, the 4-cyclobutanediol, 2, two (3-hydroxyl-oxethyl the phenyl)-propane and 2 of 2-, two (the 4-hydroxyl propoxy-phenyl) propane of 2-.Polyester composition I can be by two or more above-mentioned glycol preparations.
The preferred polyester composition comprises the PCT polyester, and wherein diacid (dicarboxylic acid) residue is made up of the 100mol% terephthalic acid residue, and perhaps this dicarboxylic acid residue is made up of with about 35mol% isophthalic acid residues about 65mol% terephthalic acid residue.Preferably, diol residue is by 100mol%1, and 4-cyclohexanedimethanol residue is formed.Another kind of preferred polyester composition comprises the PET polyester, and wherein diacid residues is made up of the 100mol% terephthalic acid residue, and diol residue is by about 96～100mol% glycol residue and 0～4mol%1,4-cyclohexanedimethanol residue composition.The polyester composition also can comprise on a small quantity, as the trifunctional of the highest about 1mol% or the residue of four sense comonomers, this type of monomer for example is trimellitic acid 1,2-anhydride, TriMethylolPropane(TMP), 1,2,4,5-pyromellitic acid dianhydride, tetramethylolmethane and technical general known other generate the polyprotonic acid or the polyvalent alcohol of polyester.
Can be used for implementing polyester of the present invention and can have the wider molecular weight scope, for example its limiting viscosity is in the scope of about 0.4～1.2dL/g, and this numerical value is to adopt the solution of 0.5g sample in 100mL60/40 weight ratio phenol/tetrachloroethane to measure under 25 ℃ temperature.The limiting viscosity that preferred this polyester has is in about 0.5～1.0dL/g scope.
The polyester that can be used as polyester composition I be supply on the market and/or can adopt the technical traditional polycondensation program preparation of knowing.These methods comprise the direct condensation of a kind or multiple dicarboxylic acid and a kind or multiple glycol, perhaps adopt the transesterify of dicarboxylic acid dialkyl esters.For example, dimethyl terephthalate ester such as dimethyl terephthalate (DMT) and a kind or the high temperature transesterify of multiple glycol in the presence of catalyzer.Decide on the desired polymerization degree, polyester also can adopt method for solid phase polymerization further to process.
Polyester composition I can be such PCT polyester, and it comprises 50mol% terephthalic acid residue and at least 98～50mol%1 at least, 4-cyclohexanedimethanol.This PCT polymkeric substance is optional can to adopt the highest 50mol%1 kind or multiple different dicarboxylic acid except that terephthalic acid to carry out modification.The example of the dicarboxylic acid that this kind is different provides in the above.In addition, this PCT polyester also can adopt 2～50mol%1 kind or multiple different glycol except that 1,4 cyclohexane dimethanol to carry out modification.The other glycol of this kind comprises cycloaliphatic diol, preferably has 6～20 carbon atoms; Or aliphatic diol, preferably have 2～20 carbon atoms.Can cooperate 1, the 4-cyclohexanedimethanol in conjunction with the example of this type of glycol of entering is together: ethylene glycol, glycol ether, triglycol, propane-1, the 3-glycol, butane-1, the 4-glycol, pentane-1, the 5-glycol, hexane-1, the 6-glycol, 3-methyl pentanediol-(2,4), 2 hexylene glycol-(1,4), 2,2,4-neopentyl glycol-(1,3), 2-Rutgers 612-(1,3), 2,2-diethyl propane-1, the 3-glycol, 1, the 3-hexylene glycol, 1, two (hydroxyl-oxethyl) benzene of 4-, 2, two (4-hydroxy-cyclohexyl) propane of 2-, 1,1,3,3-tetramethyl--2,4-cyclobutanediol, 2, two (3-hydroxyl-oxethyl the phenyl)-propane and 2 of 2-, two (the 4-hydroxyl propoxy-phenyl) propane of 2-.The dicarboxylic acid part of PCT polyester preferably is made up of the 100mol% terephthalic acid residue, and perhaps this dicarboxylic acid part is made up of 65mol% terephthalic acid residue and 35mol% isophthalic acid residues.Preferably, glycol moiety is by 100mol%1, and 4-cyclohexanedimethanol residue is formed.
Alternatively, polyester composition I contains 90mol% terephthalic acid residue's and at least 98～50mol% glycol residue pet polymer at least.This pet polymer can be randomly carries out modification with the highest 10mol%1 kind or multiple different dicarboxylic acid except that terephthalic acid.The example of the different dicarboxylic acid of this kind provides in the above.In addition, pet polymer can be randomly carries out modification with the highest about 2～50mol%1 kind or multiple different glycol except that ethylene glycol.The other glycol of this kind comprises cycloaliphatic diol, preferably has 6～20 carbon atoms; Or aliphatic diol, preferably have 3～20 carbon atoms.This kind cooperates ethylene glycol in conjunction with the example of the glycol of entering to be: glycol ether, triglycol, 1, the 4-cyclohexanedimethanol, propane-1, the 3-glycol, butane-1, the 4-glycol, pentane-1, the 5-glycol, hexane-1, the 6-glycol, 3-methyl pentanediol-(2,4), 2 hexylene glycol-(1,4), 2,2,4-neopentyl glycol-(1,3), 2-Rutgers 612-(1,3), 2,2-diethyl propane-1, the 3-glycol, 1, the 3-hexylene glycol, 1, two (hydroxyl-oxethyl) benzene of 4-, 2, two (4-hydroxy-cyclohexyl) propane of 2-, 1,1,3,3-tetramethyl--2,4-cyclobutanediol, 2, two (the 3-hydroxyl-oxethyl phenyl) propane and 2 of 2-, two (the 4-hydroxyl propoxy-phenyl) propane of 2-.1,4 cyclohexane dimethanol is preferred.
Constitute and be applicable to that the ethene polymers that contains epoxy of composition II of the present invention has general formula:
X/Y/Z wherein X is monomeric unit or the residue that is generated by ethene, and its amount that exists in polymkeric substance is preferably about 50～about 95wt%.Preferably, the amount that exists in multipolymer of X is about 60～about 84wt%.Y is generated or deutero-monomeric unit or residue by vinyl acetate between to for plastic or monomer with following array structure:
Figure A9880984600081
R wherein 1Be to contain 1～about 12 carbon atoms of having an appointment, the alkyl or cycloalkyl group of preferred about 1～about 6 carbon atoms.R 1Most preferably be ethyl group or methyl group.R 1Can also be phenyl or alkyl phenyl group, its moieties contains 1～about 12 carbon atoms of having an appointment, preferred about 1～about 6 carbon atoms.R 2Can be hydrogen, methyl or ethyl, preferably hydrogen.Y most preferably represents acrylate or vinyl acetate.The amount that Y exists in polymkeric substance is about 4～about 35wt%, and the amount that preferably exists in polymkeric substance is about 15～about 30wt%.
Z is monomeric unit or the residue that contains epoxide group, is selected from the monomer such as glycidyl acrylate and glycidyl methacrylate.Z is glycidyl methacrylate preferably.The amount that Z exists in polymkeric substance is about 1～about 15wt%, and the amount that preferably exists in polymkeric substance is about 1～about 10wt%.
The ethene polymers preferred content with about 2～about 10wt% in the present composition that contains epoxy exists.The content of this about 2～10wt% can be made up of a kind or the multiple ethene polymers that contains epoxy.Be suitable for the ethene polymers that contains epoxide group of the present invention and can adopt the random or direct copolymerization process preparation of block well known to those skilled in the art.Block polymer is preferred.
Polymer blend of the present invention also comprises aromatic phosphite.Typical aromatic phosphite comprises three (2, the 4-di-tert-butyl-phenyl) phosphorous acid ester, is sold by trade(brand)name Irgafos168 by Ciba-Geigy; 4, two (the 3-methyl-6-tert butyl phenyl-double tridecyl) phosphorous acid esters of 4 '-Ding fork are sold by trade(brand)name Mark P by Adeka Argus chemical company; Three (single nonyl phenyl) phosphorous acid ester, four (2, the 4-di-tert-butyl-phenyl) 4,4 '-diphenylene, two phosphinates (diphenylilenediphosphonite) and two (2, the 4-di-tert-butyl-phenyl) diphosphites of tetramethylolmethane is sold by trade(brand)name ULTRANOX 626 by GE special chemical article company.Can use a kind or multiple aromatic phosphite compound of the present invention.The content that aromatic phosphite composition III is present in the polymer blend of the present invention is about 0.1～5wt%.
The ferrous components IV of the present composition is selected from Fe 3O 4Ferric oxide (magnetite ferric oxide) and element (reductive) iron.Ferrous components IV preferably accounts for about 25～about 50wt% of polymer blend, preferred about 30～about 45wt%.Owing to added elemental iron or Fe 3O 4Ferric oxide (magnetite ferric oxide), this polymer blend shows the magnetism to magnetic field.
The present invention can obtain by the embodiment of its following preferred embodiment further to illustrate, but will know that the purpose that provides these embodiment only is to illustrate, and does not intend scope of the present invention made and defines, unless specifically indicate in addition.
Embodiment
By extrude the composition that the compounding preparation is made up of following ingredients with twin screw extruder: 67.26wt% gathers (ethylene glycol terephthalate), 30wt%Fe 3O 4The diphosphites and 0.09% calcium stearate (demoulding compound) of ferric oxide, 2.5wt% ethylene/methyl acrylate/glycidyl methacrylate copolymer, 0.15% pair of (2, the 4-di-tert-butyl-phenyl) tetramethylolmethane.The composition that is obtained can be configured as the tough and tensile sheet material that is included in the stay hook that uses in conventional hook/ring technique for fixing.The sheet material that is obtained/hook product will show suction in magnetic field.This sheet material/hook product can adopt the production of sheet material extrusion molding.

Claims (7)

1. a thermoplasticity, magnetic polyester compositions comprise:
I. about 39.5～about 72.9wt% thermoplastic polyester comprises following ingredients:
(A) comprise 50mol% terephthalic acid residue's diacid residues at least; And
(B) comprise at least 50mol% by the diol residue of ethylene glycol, 1,4 cyclohexane dimethanol or its mixture deutero-residue;
II. about 2～about 10wt%1 kind or multiple general formula are the ethene polymers that contains epoxy of X/Y/Z, wherein:
X represents the ethene residue, and it accounts for about 50～95wt% of polymkeric substance X/Y/Z;
Y representative is by vinyl acetate or have the residue of the compound deriving of following formula:
Figure A9880984600021
R wherein 1Be the alkyl or cycloalkyl group that contains the highest about 12 carbon atoms, or phenyl or alkyl phenyl group, moieties wherein contains the highest about 12 carbon atoms; R 2Be hydrogen, methyl or ethyl; Y accounts for about 4～35wt% of polymkeric substance E/X/Y;
The Z representative is by the residue of the monomer derived that contains epoxide group that is selected from glycidyl acrylate and glycidyl methacrylate, and Z accounts for about 1～15wt% of polymkeric substance X/Y/Z;
III. about 0.1～about 0.5wt%1 kind or multiple aromatic phosphite compound; And
IV. about 25～about 50wt% is selected from Fe 3O 4The ferrous components of ferric oxide and elemental iron;
Wherein polyester composition I is based on 100mol% diacid residues and 100mol% diol residue, and the weight percentage of each is that gross weight in composition I, II, III and IV is a benchmark among composition I, II, III and the IV.
2. the composition of claim 1, wherein the limiting viscosity of polyester composition I is in the scope of about 0.5～1.0dL/g, and this numerical value is to adopt the solution of 0.5g sample in 100mL60/40 weight ratio phenol/tetrachloroethane to measure under 25 ℃ temperature.
3. the composition of claim 2, wherein composition II has general formula X/Y/Z, wherein:
X represents the ethene residue, and it accounts for about 60～84wt% of polymkeric substance X/Y/Z;
Y representative is by vinyl acetate or have the residue of the compound deriving of following formula:
Figure A9880984600031
R wherein 1It is the alkyl group that contains 1～about 6 carbon atoms; R 2Be hydrogen, methyl or ethyl; Y accounts for about 15～30wt% of polymkeric substance E/X/Y;
The Z representative is by the residue of the monomer derived that contains epoxide group that is selected from glycidyl acrylate and glycidyl methacrylate, and Z accounts for about 1～10wt% of polymkeric substance X/Y/Z.
4. the thermoplasticity of claim 1, magnetic polyester compositions comprise:
I. about 39.5～about 72.9wt% thermoplastic polyester, its limiting viscosity are in the scope of about 0.5～1.0dL/g, and this numerical value is to adopt the solution of 0.5g sample in 100mL60/40 weight ratio phenol/tetrachloroethane to measure under 25 ℃ temperature, comprises following ingredients:
(A) diacid residues is formed with about 35mol% isophthalic acid residues by the 100mol% terephthalic acid residue or by about 65mol% terephthalic acid residue; And
(B) comprise at least 50mol% by the diol residue of ethylene glycol, 1,4 cyclohexane dimethanol or its mixture deutero-residue;
II. about 2～10wt%1 kind or multiple general formula are the ethene polymers that contains epoxy of X/Y/Z, wherein:
X represents the ethene residue, and it accounts for about 60～84wt% of polymkeric substance X/Y/Z;
Y represents the residue by the compound deriving with following formula: R wherein 1It is the alkyl group that contains 1～about 6 carbon atoms; R 2Be hydrogen, methyl or ethyl; Y accounts for about 15～30wt% of polymkeric substance E/X/Y; With
The Z representative is by the residue of the monomer derived that contains epoxide group that is selected from glycidyl acrylate and glycidyl methacrylate, and Z accounts for about 1～10wt% of polymkeric substance X/Y/Z.
5. the composition of claim 4, wherein the diol residue of thermoplastic polyester is by 100mol%1, and 4-cyclohexanedimethanol residue is formed; Y is methyl or ethyl; And composition III is selected from three (2, the 4-di-tert-butyl-phenyl) phosphorous acid ester, 4, two (3-methyl-6-tert butyl phenyl-double tridecyl) phosphorous acid ester, three (the single nonyl phenyl) phosphorous acid esters, four (2 of 4 '-Ding fork, the 4-di-tert-butyl-phenyl) 4,4 '-diphenylene, two phosphinates (diphenylilenediphosphonite) and the diphosphites of two (2, the 4-di-tert-butyl-phenyl) tetramethylolmethane.
6. the thermoplasticity of claim 1, magnetic polyester compositions comprise:
I. about 39.5～about 72.9wt% thermoplastic polyester, its limiting viscosity are in the scope of about 0.5～1.0dL/g, and this numerical value is to adopt the solution of 0.5g sample in 100mL60/40 weight ratio phenol/tetrachloroethane to measure under 25 ℃ temperature, comprises following ingredients:
(A) diacid residues of forming by the 100mol% terephthalic acid residue; And
(B) by about 96～100mol% glycol residue and 0～about 4mol%1, the diol residue that 4-cyclohexanedimethanol residue is formed;
II. about 2～10wt%1 kind or multiple general formula are the ethene polymers that contains epoxy group(ing) of X/Y/Z, wherein:
X represents the ethene residue, and it accounts for about 60～84wt% of polymkeric substance X/Y/Z;
Y represents the residue by the compound deriving with following formula: R wherein 1It is the alkyl group that contains 1～about 6 carbon atoms; R 2Be hydrogen, methyl or ethyl; Y accounts for about 15～30wt% of polymkeric substance E/X/Y;
The Z representative is by the residue of the monomer derived that contains epoxide group that is selected from glycidyl acrylate and glycidyl methacrylate, and Z accounts for about 1～10wt% of polymkeric substance X/Y/Z.
7. the composition of claim 6, wherein Y is methyl or ethyl; And composition III is selected from three (2, the 4-di-tert-butyl-phenyl) phosphorous acid ester, 4, two (3-methyl-6-tert butyl phenyl-double tridecyl) phosphorous acid ester, three (the single nonyl phenyl) phosphorous acid esters, four (2 of 4 '-Ding fork, the 4-di-tert-butyl-phenyl) 4, the diphosphites of 4 '-diphenylene, two phosphinates (diphenylilenediphosphonite) and two (2, the 4-di-tert-butyl-phenyl) tetramethylolmethane.
CN 98809846 1997-10-03 1998-09-29 Magnetic polyester compositions Pending CN1273593A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US6303797P 1997-10-03 1997-10-03
US60/063,037 1997-10-03
US09/160,487 1998-09-25
US09/160,487 US5919848A (en) 1997-10-03 1998-09-25 Magnetic polyester compositions

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CN1273593A true CN1273593A (en) 2000-11-15

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JP (1) JP2001519452A (en)
CN (1) CN1273593A (en)
BR (1) BR9812719A (en)
WO (1) WO1999018158A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110527411A (en) * 2019-09-12 2019-12-03 安徽神剑新材料股份有限公司 A kind of powdery paints and preparation method thereof with magnetic polyester resin

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SE526078C2 (en) * 2003-02-21 2005-06-28 Grindfill Ab Passively magnetic foil for notice device for posting information or advertisement on supportive structure, includes layer containing iron material and coated with coating material that forms additional layer directly on the layer
WO2004092268A1 (en) * 2003-04-15 2004-10-28 The Yokohama Rubber Co. Ltd. Resin composition for molding and application and noise reducing material using the same

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EP0174343B1 (en) * 1984-02-24 1992-04-29 E.I. Du Pont De Nemours And Company Toughened thermoplastic polyester compositions
US5356984A (en) * 1994-02-14 1994-10-18 General Electric Company Method for molding magnets and compositions for use therein
JPH09165502A (en) * 1995-12-18 1997-06-24 Bridgestone Corp Composition for bond magnet

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110527411A (en) * 2019-09-12 2019-12-03 安徽神剑新材料股份有限公司 A kind of powdery paints and preparation method thereof with magnetic polyester resin

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