CA2513266A1 - Foamable interpolymer resin particles containing limonene as a blowing aid - Google Patents

Foamable interpolymer resin particles containing limonene as a blowing aid Download PDF

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Publication number
CA2513266A1
CA2513266A1 CA002513266A CA2513266A CA2513266A1 CA 2513266 A1 CA2513266 A1 CA 2513266A1 CA 002513266 A CA002513266 A CA 002513266A CA 2513266 A CA2513266 A CA 2513266A CA 2513266 A1 CA2513266 A1 CA 2513266A1
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CA
Canada
Prior art keywords
resin particles
weight
vinyl aromatic
foamable
limonene
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.)
Granted
Application number
CA002513266A
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French (fr)
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CA2513266C (en
Inventor
Paul Edward Arch
Edwin Niemann
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Bvpv Styrenics LLC
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Individual
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Publication of CA2513266A1 publication Critical patent/CA2513266A1/en
Application granted granted Critical
Publication of CA2513266C publication Critical patent/CA2513266C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/16—Making expandable particles
    • C08J9/18—Making expandable particles by impregnating polymer particles with the blowing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/141—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/16—Making expandable particles
    • C08J9/20—Making expandable particles by suspension polymerisation in the presence of the blowing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C08J2203/142—Halogenated saturated hydrocarbons, e.g. H3C-CF3
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02—Homopolymers or copolymers of hydrocarbons
    • C08J2325/04—Homopolymers or copolymers of styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C08J2351/06—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2425/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers

Abstract

Interpolymer resin particles comprised of 20% to 80% by weight polyolefin, e.g.polyethylene and 80% to 20% by weight of an in situ polymerized vinyl aromatic resin, e.g. polystyrene or poly(styrene.butyl acrylate) and forming an interpenetrating network of polyolefin and vinyl aromatic resin particles.
The interpolymer particles are impregnated with a volatile hydrocarbon blowing agent, and limonene, e.g. d-limonene, ranging from about 0.1 to about 5 parts, preferably 0.1 to 1 part by weight, based on 100 parts by weight of the interpolymer particles, for improved expandability and a pleasant fragrance.

Claims (18)

1. Foamable interpolymer resin particles comprising:
about 20% to about 80% by weight polyolefin and from about 80% to about 20% by weight of a polymerized vinyl aromatic resin forming an interpenetrating network of polyolefin and vinyl aromatic resin particles;
from about 1.5% by weight to about 20% by weight of a blowing agent and from about 0.1 to about 5 parts by weight limonene based on 100 parts by weight of said interpolymer particles, impregnated in said interpolymer resin particles.
2. Foamable interpolymer resin particles of claim 1 wherein said weight of said polymerized vinyl aromatic resin ranges from about 45% to about 80% by weight and wherein said weight of said polyolefin ranges from about 20% to about 55% by weight based on the weight of said interpolymer particles.
3. Foamable interpolymer resin particles of claim 1 wherein said vinyl aromatic resin is selected from the group consisting of vinyl aromatic homopolymer and vinyl aromatic copolymer, which is polymerized in said polyolefin particles.
4. Foamable interpolymer resin particles of claim 3 wherein said vinyl aromatic resin consists of vinyl aromatic copolymer.
5. Foamable interpolymer resin particles of claim 3 wherein said vinyl aromatic copolymer is a copolymer of styrene and butyl acrylate.
6. Foamable interpolymer resin particles of claim 3 wherein said vinyl aromatic resin consists of vinyl aromatic homopolymer.
7. Foamable interpolymer resin particles of claim 6 wherein said vinyl aromatic homopolymer is styrene.
8. Foamable interpolymer resin particles of claim 1 wherein said blowing agent is selected from the group consisting of n-propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, neopentane, cyclobutane, cyclopentane, methyl chloride, ethyl chloride, methylene chloride, trichlorofluoromethane, dischlorofluoromethane, dichlorodifluormethane, chlorodifluoromethane and dichloroetetrafluoroethane, and mixtures thereof.
9. Foamable interpolymer resin particles of claim 8 wherein said blowing agent is selected from the group consisting of n-pentane, iso-pentane, neopentane, cyclopentane, and mixtures thereof.
10. Foamable interpolymer resin particles of claim 1 wherein said polyolefin is polyethylene.
11. Foamable interpolymer resin particles of claim 1 wherein said limonene is selected from the group consisting of d-limonene, 1-limonene,and dl-limonene.
12. Foamable interpolymer resin particles of claim 11 wherein said limonene is d-limonene.
13. Foamable interpolymer resin particles of claim 1 wherein said limonene ranges from about 0.1 to 1 parts by weight based on 100 parts by weight of said interpolymer particles.
14. A foamed article with at least improved physical properties produced from the foamable interpolymer resin particles of claim 1.
15. A process for forming the foamable interpolymer resin particles of claim 1 comprising the steps of blending said blowing agent and said limonene together to form a mixture and adding said mixture to said interpolymer resin particles in the impregnation step of said interpolymer resin particles.
16. A process for forming the foamable interpolymer resin particles of claim comprising the steps of adding said blowing agent and said limonene separately to the interpolymer resin particles in the impregnation step of said interpolymer resin particles.
17. A process of claim 15 wherein said polyolefin is polyethylene and said vinyl aromatic resin is styrene.
18. A process of claim 16 wherein said polyolefin is polyethylene and said vinyl aromatic resin is styrene.
CA2513266A 2003-01-27 2004-01-23 Foamable interpolymer resin particles containing limonene as a blowing aid Expired - Lifetime CA2513266C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US44276103P 2003-01-27 2003-01-27
US60/442,761 2003-01-27
PCT/US2004/001824 WO2004069917A2 (en) 2003-01-27 2004-01-23 Foamable interpolymer resin particles containing limonene as a blowing aid

Publications (2)

Publication Number Publication Date
CA2513266A1 true CA2513266A1 (en) 2004-08-19
CA2513266C CA2513266C (en) 2012-01-03

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CA2513266A Expired - Lifetime CA2513266C (en) 2003-01-27 2004-01-23 Foamable interpolymer resin particles containing limonene as a blowing aid

Country Status (13)

Country Link
US (1) US6908949B2 (en)
EP (1) EP1587861B1 (en)
JP (1) JP2006515648A (en)
KR (1) KR20050104355A (en)
CN (1) CN100339423C (en)
AT (1) ATE553147T1 (en)
AU (1) AU2004209533B2 (en)
BR (1) BRPI0406930B8 (en)
CA (1) CA2513266C (en)
MX (1) MXPA05007777A (en)
NO (1) NO20053653L (en)
PL (1) PL209097B1 (en)
WO (1) WO2004069917A2 (en)

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Publication number Publication date
KR20050104355A (en) 2005-11-02
US6908949B2 (en) 2005-06-21
AU2004209533B2 (en) 2008-10-02
BRPI0406930B8 (en) 2022-08-02
CA2513266C (en) 2012-01-03
JP2006515648A (en) 2006-06-01
ATE553147T1 (en) 2012-04-15
AU2004209533A1 (en) 2004-08-19
EP1587861B1 (en) 2012-04-11
EP1587861A4 (en) 2006-03-22
PL209097B1 (en) 2011-07-29
PL377254A1 (en) 2006-01-23
BRPI0406930A (en) 2006-01-03
MXPA05007777A (en) 2005-09-30
US20040152795A1 (en) 2004-08-05
NO20053653D0 (en) 2005-07-27
WO2004069917A2 (en) 2004-08-19
NO20053653L (en) 2005-08-25
BRPI0406930B1 (en) 2014-08-26
EP1587861A2 (en) 2005-10-26
CN100339423C (en) 2007-09-26
CN1745130A (en) 2006-03-08
WO2004069917A3 (en) 2004-09-23

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