CN101070418B - Composition for low-odor thermoplastic resin - Google Patents

Composition for low-odor thermoplastic resin Download PDF

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CN101070418B
CN101070418B CN2006101646308A CN200610164630A CN101070418B CN 101070418 B CN101070418 B CN 101070418B CN 2006101646308 A CN2006101646308 A CN 2006101646308A CN 200610164630 A CN200610164630 A CN 200610164630A CN 101070418 B CN101070418 B CN 101070418B
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resin
alpha
unsaturated nitrile
styrene
maleimide
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CN101070418A (en
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金宰弘
郑淳俊
朴凤铉
孙东辙
李济龙
李龙哲
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Echo Plastic Co Ltd
Hyundai Motor Co
Kumho Petrochemical Co Ltd
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Echo Plastic Co Ltd
Korea Kumho Petrochemical Co Ltd
Hyundai Motor Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/02—Polymerisation in bulk
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • C08F279/04—Vinyl aromatic monomers and nitriles as the only monomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/02—Flame or fire retardant/resistant
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend

Abstract

The present invention relates to a low-odor thermoplastic resin composition. In particular the resin of the resin composition is prepared by a new bulk polymerization process that is used to reduce the characteristic chemical odor in new cars. The resin minimizes the use of the resin prepared by the conventional emulsion polymerization process, N-substituted maleimide and alpha-alkylstyrene-based heat-resistant materials which are used to improve heat resistance and the molecular weight of the matrix of the thermoplastic composition. The resin is also improves impact strength, thereby having reduced characteristic chemical odor, while having superior impact strength and heat resistance.

Description

Composition for low-odor thermoplastic resin
The cross reference of related application
The application's requirement is right of priority with on May 10th, 2006 and on July 7th, 2006 to korean patent application No.10-2006-0042060 and the 10-2006-0062058 that Korea S Department of Intellectual Property proposes, and the disclosed content of above-mentioned application is hereby incorporated by reference.
Invention field
The present invention relates to composition for low-odor thermoplastic resin.
Background technology
Normally used acrylonitrile-butadiene-styrene (ABS) (" ABS ") copolymer resin also is referred to as the grafted rubber components of domain structure (domain) by a) being in disperse phase; And b) be in external phase, acrylonitrile-styrene (" the SAN ") copolymer resin that also is referred to as matrix (matrix) is formed.In requiring the product of excellent heat resistance (as electrical/electronic application, outdoor advertising and trolley part), some monomers are replaced to improve thermotolerance with alpha-alkyl phenylethylene, alpha-alkyl phenylethylene has high glass-transition temperature (Tg), thereby make the zone have higher thermotolerance mutually, to improve thermotolerance.Selectively, some matrixes are replaced with alpha-alkyl phenylethylene or N-substituted maleimide amine type resin.
Usual method is favourable obtaining aspect good impact property and the thermotolerance.Yet, because grafted rubber components and alpha-alkyl phenylethylene type resin etc. form by emulsion polymerization prepared, 80% or more lower molecular weight additive remain in the final product.Especially for automobile inner part, these residual additives are emitted volatile organic compounds, and its distinctive chemical odor makes the passenger unhappy.
Along with automotive industry with the needs of the trend that changes day by day, concerning the material producer, when keeping good physical, improve chemical odor and become important problem.
Summary of the invention
The invention provides a kind of composition for low-odor thermoplastic resin, it comprises: a) about 25wt% is to the unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of the mass polymerization of the volume particle size of about 45wt%; B) about 5wt% is to the unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of the letex polymerization of about 15wt%; C) about 20wt% is to the unsaturated nitrile-aromatic vinyl monomer resin of the mass polymerization of about 30wt%; D) about 10wt% is to the alpha-alkyl phenylethylene-unsaturated nitrile-styrene resin of the mass polymerization of about 20wt%; And e) about 10wt% is to the N-substituted maleimide amine-unsaturated ethylene thiazolinyl monomer resin of the solution polymerization of about 20wt%.
In an exemplary embodiment of the present invention embodiment, composition for low-odor thermoplastic resin comprises a) unsaturated nitrile, is selected from vinyl cyanide, methacrylonitrile and ethyl acrylonitrile (ethacrylonitrile); B) elastoprene is selected from divinyl rubber and synthetic polyisoprene; C) aromatic vinyl monomer, be selected from vinylbenzene, alpha-methyl styrene, Vinyl toluene, t-butyl styrene, halogenated styrenes, and composition thereof; D) alpha-alkyl phenylethylene is selected from alpha-methyl styrene, α-ethyl styrene and methyl-alpha-methyl styrene; And e) N-substituted maleimide amine is selected from N-phenylmaleimide, N-(2-aminomethyl phenyl) maleimide, N-dodecyl maleimide, N-benzyl maleimide, N-chloro-phenyl-maleimide and N-dichlorophenyl maleimide.
In another illustrative embodiments of the present invention, composition for low-odor thermoplastic resin comprises that granularity is the unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of about 1 μ m to the mass polymerization of about 4 μ m.
Description of drawings
Fig. 1 illustrates the structure of ABS resin.
Fig. 2 illustrates an exemplary embodiment of the present invention.
Embodiment
In order to solve the major issue that comprises multiple low molecule additive in the conventional emulsion polymerization product, the invention provides a kind of unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of mass polymerization of volume particle size, described low molecule additive produces volatile organic compound, is the main cause that produces chemical odor.The invention provides the bulk polymerization of the cause of removing chemical odor.The present invention has reduced the use of the letex polymerization unsaturated nitrile-elastoprene-aromatic vinyl monomer that adds for the raising impact property.The present invention makes the ratio optimization of mass polymerization alpha-alkyl phenylethylene-unsaturated nitrile-styrene resin and solution polymerization N-substituted maleimide amine-unsaturated ethylene thiazolinyl monomer resin, described ratio satisfy the necessary thermotolerance requirement of automotive interior material.Because the adding of N-substituted maleimide amine may reduce impact property, the present invention adopts high molecular to compensate impact property.
In one embodiment, provide a kind of composition for low-odor thermoplastic resin that when keeping excellent heat resistance and impact property, reduces chemical odor.
The invention is characterized in composition for low-odor thermoplastic resin, it comprises: approximately 25wt% is to the unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of the mass polymerization of the volume particle size of about 45wt%, approximately 5wt% is to the unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of the letex polymerization of about 15wt%, approximately 20wt% is to the unsaturated nitrile-aromatic vinyl monomer resin of the mass polymerization of about 30wt%, and approximately 10wt% extremely approximately 83Alpha-alkyl phenylethylene-the unsaturated nitrile of the mass polymerization of 20wt%-styrene resin and about 10wt% are to the N-substituted maleimide amine-unsaturated ethylene thiazolinyl monomer resin of the solution polymerization of about 20wt%.
The present invention relates to the composition for low-odor thermoplastic resin that chemical odor obviously reduces when possessing excellent heat resistance.Particularly, by mixing about 25wt% to the unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of the approximately mass polymerization of the volume particle size of 45wt%, approximately 5wt% is to the unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of the approximately letex polymerization of 15wt%, approximately 20wt% is to the unsaturated nitrile-aromatic vinyl monomer resin of the approximately mass polymerization of 30wt%, approximately 10wt% is to approximately 107Alpha-alkyl phenylethylene-the unsaturated nitrile of the mass polymerization of 20wt%-styrene resin and about 10wt% are to the thermoplastic resin composition that N-substituted maleimide amine-unsaturated ethylene thiazolinyl monomer resin is prepared from of the solution polymerization of about 20wt%, its impact (notch shock) intensity is about 15 to about 20, tensile strength is about 470 to about 510, heat deflection temperature (HDT) (HDT) is about 100 ℃ to about 107 ℃, and oder levels is about 4.0.
If the content of the mass polymerization unsaturated nitrile-elastoprene-aromatic vinyl monomer resin of granularity big (about 1 μ m is to about 4 μ m) is less than about 25wt%, shock strength may reduce.On the contrary, if surpass about 45wt%, tensile strength may be obviously weak.If the consumption of letex polymerization unsaturated nitrile-elastoprene-aromatic vinyl monomer resin is less than about 5wt%, shock strength may reduce.On the contrary, if surpass about 15wt%, chemical odor may not can reduce.If the consumption of mass polymerization unsaturated nitrile-aromatic vinyl monomer resin is less than about 20wt%, shock strength may reduce.On the contrary, if surpass about 30wt%, thermotolerance may weaken.If the consumption of mass polymerization alpha-alkyl phenylethylene-unsaturated nitrile-aromatic vinyl monomer resin can not obtain enough thermotolerances less than about 10wt%.On the contrary, if surpass about 20wt%, shock strength may weaken and the good thermotolerance of very difficult acquisition.If the consumption of solution polymerization N-substituted maleimide amine-unsaturated ethylene thiazolinyl monomer resin less than about 10wt%, is difficult to obtain good thermotolerance, on the contrary, if surpass about 20wt%, shock strength may weaken.
Typical elastoprene includes but not limited to divinyl rubber and synthetic polyisoprene.Typical unsaturated nitrile includes but not limited to vinyl cyanide, methacrylonitrile and ethyl acrylonitrile.Typical aromatic vinyl monomer include but not limited to vinylbenzene, alpha-methyl styrene, Vinyl toluene, t-butyl styrene, halogenated styrenes, and composition thereof.Typical alpha-alkyl phenylethylene includes but not limited to alpha-methyl styrene, α-ethyl styrene and methyl-alpha-methyl styrene.Typical N-substituted maleimide amine includes but not limited to N-phenylmaleimide, N-(2-aminomethyl phenyl) maleimide, N-dodecyl maleimide, N-benzyl maleimide, N-chloro-phenyl-maleimide and N-dichlorophenyl maleimide.
The invention provides the bulk polymerization that reduces chemical odor.Consider final physicals, the resin of letex polymerization is minimized.In order to improve thermotolerance, N-substituted maleimide amine uses with alpha-alkyl phenylethylene.And the molecular weight of increase thermoplastic compounds matrix is with the shock strength of compensation minimizing.Therefore, providing excellent impact strength and the stable on heating chemical odor that makes simultaneously to reduce to minimum.
Embodiment 1-5
Resin compound comprises a) as impact-resistance modified dose the acrylonitrile-butadiene-styrene (ABS) bulk copolymerization thing and acrylonitrile-butadiene-styrene (ABS) emulsion copolymers, the b of volume particle size) alpha-methyl styrene-acrylonitrile-styrene bulk copolymerization thing and as N-phenylmaleimide-styrene solution multipolymer, the c of heat-stable material) as the molecular-weight average (M of impact modifying agent w) be about 150,000 dalton to about 250,000 daltonian acrylonitrile-styrene bulk copolymerization things, d) as the N of lubricant, N '-ethylenebisstearamide and e) the phenyl antioxidant, with it with about 10 minutes of rotary drum uniform mixing.Subsequently, with mixture forcing machine (25 Φ twin screw extruders, W﹠amp; P) extrude to about 260 ℃ bowl temperature at about 195 ℃, obtain particle.In order to measure thermotolerance and other physicals, particle was descended dry about 3 hours at about 90 ℃ in traditional baking oven.Measuring result is listed in the following table 1.
A) measurement of physicals: use 4.0-ounce (ounce) forcing machine (DongShin Hydraulics) or coordinator by the granules preparation specimen according to the ASTM standard, be used to measure IZOD shock strength, tensile strength and heat deflection temperature (HDT).
B) measurement of total volatile organic compound (" VOC "): about 1000mg particulate samples is placed in vitro.By collection and confinement of gases, pyrolysis and desorption, with the H.S.S-GC/MASS spectrometer content of volatile organic compounds is carried out quantitative analysis, volatile organic compounds is the main reason of chemical odor.
C) smell test: test is carried out according to the MS 300-34 standard of Hyundai Motor Company, and this standard is similar with the testing standard of external main motor corporation (Ford, GM, Toyota etc.).
A. standard test condition
23 ± 2 ℃, R.H.65 ± 5%, unless otherwise indicated.
Specimen should be preserved 25 hours under this condition at least.
B. sampling
The specimen size: 100mm is wide, and 100mm is long.
C. specimen places in the 3L container.With container sealing, and in 80 ± 2 ℃ thermostatic bath, placed 3 hours.3 or 4 assessors hear the smell of sample and carry out the sample ranking.
D. oder levels
Grade
5 Odorlessness.
4 Smell slightly.
3 A little smells, but can accept.
2 Smell consumingly, but be not to stand.
1 Smell is pungent, is difficult to stand.
[0033]Table 1
Figure G061G4630820061222D000061
Comparative example 1-5
Resin compound comprises a) acrylonitrile-butadiene-styrene (ABS) emulsion copolymers, the b as anti-impact modifier) alpha-methyl styrene-acrylonitrile emulsion multipolymer, c) as N-phenylmaleimide-styrene solution multipolymer, the d of heat-stable material) molecular-weight average (M w) be about 80,000 dalton to about 110,000 daltonian low molecular weight propylene nitrile-vinylbenzene bulk copolymerization things, e) as the N of lubricant, N '-ethylenebisstearamide and f) the phenyl antioxidant, with it with about 10 minutes of rotary drum uniform mixing.Subsequently, with mixture through forcing machine (25 Φ twin screw extruders, W﹠amp; Q) extrude to about 260 ℃ bowl temperature at about 195 ℃, obtain particle.In order to measure thermotolerance and other physicals, particle descended dry about 3 hours at about 90 ℃ in common baking oven.Measuring result is listed in the following table 2.
Physicals, total VOC and smell are according to the described method test of the foregoing description.
Table 2
Figure G061G4630820061222D000071
By replacing the conventional emulsion polymerization process with new bulk polymerization, the present invention has significantly reduced distinctive chemical odor in the new cars.
And N-substituted maleimide amine and alpha-alkyl phenylethylene heat-stable material strengthen thermotolerance, and the molecular weight of thermoplastic compounds matrix is increased, and therefore the reduction of compensation shock strength is keeping excellent impact strength and the stable on heating chemical odor that makes simultaneously to minimize.
It will be recognized by those skilled in the art that disclosed notion and embodiment are easy to as the basis that changes and design the alternate manner of realizing the object of the invention in aforementioned specification.Those skilled in the art will recognize that also these are equal to embodiment and do not break away from the spirit and scope of the present invention that claims are set forth.

Claims (2)

1. composition for low-odor thermoplastic resin comprises:
A) unsaturated nitrile-elastoprene of the mass polymerization of the volume particle size of 25wt% to 45wt%-aromatic vinyl monomer resin;
B) unsaturated nitrile-elastoprene of the letex polymerization of 5wt% to 15wt%-aromatic vinyl monomer resin;
C) unsaturated nitrile of the mass polymerization of 20wt% to 30wt%-aromatic vinyl monomer resin;
D) alpha-alkyl phenylethylene-unsaturated nitrile of the mass polymerization of 10wt% to 20wt%-styrene resin; With
E) the N-substituted maleimide amine of the solution polymerization of 10wt% to 20wt%-unsaturated ethylene thiazolinyl monomer resin, wherein:
A) described unsaturated nitrile is selected from vinyl cyanide, methacrylonitrile and ethyl acrylonitrile;
B) described elastoprene is selected from divinyl rubber and synthetic polyisoprene;
C) described aromatic vinyl monomer be selected from vinylbenzene, alpha-methyl styrene, Vinyl toluene, t-butyl styrene, halogenated styrenes, and composition thereof;
D) described alpha-alkyl phenylethylene is selected from alpha-methyl styrene, α-ethyl styrene and methyl alpha-methyl styrene; And
E) described N-substituted maleimide amine is selected from N-phenylmaleimide, N-(2-aminomethyl phenyl) maleimide, N-dodecyl maleimide, N-benzyl maleimide, N-chloro-phenyl-maleimide and N-dichlorophenyl maleimide.
2. composition for low-odor thermoplastic resin according to claim 1, the granularity of the unsaturated nitrile-elastoprene of wherein said mass polymerization-aromatic vinyl monomer resin are 1 μ m to 4 μ m.
CN2006101646308A 2006-05-10 2006-11-28 Composition for low-odor thermoplastic resin Active CN101070418B (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR10-2006-0042060 2006-05-10
KR20060042060 2006-05-10
KR1020060042060 2006-05-10
KR1020060062058A KR100757600B1 (en) 2006-05-10 2006-07-03 Composition for the low-smelled thermoplastic resin
KR1020060062058 2006-07-03
KR10-2006-0062058 2006-07-03

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1053075A (en) * 1990-01-02 1991-07-17 陶氏化学公司 Have the three peak distribution ABS compositions that good gloss and gloss susceptibility reduce
CN1383444A (en) * 2000-07-03 2002-12-04 Lg化学株式会社 Process for preparing thermoplastic resin having superior heat-stability
CN1106429C (en) * 1996-11-28 2003-04-23 拜尔公司 Improved thermoplastic moulding compositions of the ABS type
CN1140579C (en) * 1998-12-18 2004-03-03 拜尔公司 Highly impact-resistant ABS moulding materials

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100546784B1 (en) * 1999-12-14 2006-01-25 제일모직주식회사 Thermoplastic resin composition with good resistance against chemical
KR100417061B1 (en) * 2000-12-13 2004-02-05 주식회사 엘지화학 Method for preparing high temperature copolymer
KR100643742B1 (en) * 2004-12-27 2006-11-10 제일모직주식회사 Thermoplastic Resin Composition with Good Adhesion of Metal Plate and High Impact Strength

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1053075A (en) * 1990-01-02 1991-07-17 陶氏化学公司 Have the three peak distribution ABS compositions that good gloss and gloss susceptibility reduce
CN1106429C (en) * 1996-11-28 2003-04-23 拜尔公司 Improved thermoplastic moulding compositions of the ABS type
CN1140579C (en) * 1998-12-18 2004-03-03 拜尔公司 Highly impact-resistant ABS moulding materials
CN1383444A (en) * 2000-07-03 2002-12-04 Lg化学株式会社 Process for preparing thermoplastic resin having superior heat-stability

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JP特开2003-246871A 2003.09.05

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