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WO2017119304A1 - Composition de résine ignifuge - Google Patents

Composition de résine ignifuge Download PDF

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Publication number
WO2017119304A1
WO2017119304A1 PCT/JP2016/088179 JP2016088179W WO2017119304A1 WO 2017119304 A1 WO2017119304 A1 WO 2017119304A1 JP 2016088179 W JP2016088179 W JP 2016088179W WO 2017119304 A1 WO2017119304 A1 WO 2017119304A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
phosphorus
resin composition
flame
flame retardant
Prior art date
Application number
PCT/JP2016/088179
Other languages
English (en)
Japanese (ja)
Inventor
徹也 飯塚
忠 山▲崎▼
孝 高橋
Original Assignee
丸善石油化学株式会社
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 丸善石油化学株式会社 filed Critical 丸善石油化学株式会社
Priority to JP2017560102A priority Critical patent/JPWO2017119304A1/ja
Publication of WO2017119304A1 publication Critical patent/WO2017119304A1/fr

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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
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds

Definitions

  • the present invention relates to a flame retardant resin composition
  • a flame retardant resin composition comprising a specific phosphorus-containing compound as a flame retardant.
  • halogen-based flame retardants have been widely used as typical flame retardants for flame retardants used in thermoplastic resins.
  • halogen-based flame retardants generate toxic gases depending on incineration conditions, they have been refrained from the viewpoint of environment and safety in recent years.
  • phosphate ester type flame retardants reduce the molecular weight of the resin by transesterification when heated and kneaded at high temperatures with resins having an ester bond such as polycarbonate resins, polyester resins, and polyacrylic resins. There is a problem that the mechanical strength and the like are lowered. Furthermore, depending on the usage environment, phosphate ester type flame retardant reacts with moisture in the air and gradually hydrolyzes to produce phenol derivatives, phosphoric acid, etc., resulting in reduced flame retardant performance or molecular weight of the resin There is a problem of further lowering.
  • phosphorus-containing compounds derived from 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (hereinafter referred to as “DOPO”) have a cyclic phosphinic ester structure. Since hydrolysis hardly occurs, it is expected as a suitable flame retardant for resins that require heat kneading at high temperatures such as polycarbonate resins and polyester resins, and various compounds have been disclosed (for example, Patent Document 1).
  • Patent Documents 3 and 4 disclose a phosphorus-containing compound represented by the following formula (A2) (hereinafter referred to as “compound (A2)”), and the phosphorus compound has a very high melting point and 13 It has been shown that a flame retardant property can be imparted with a smaller addition amount to a resin having a very high phosphorus element content of .5% by mass and requiring heat kneading at a high temperature.
  • A2 a phosphorus-containing compound represented by the following formula (A2) (hereinafter referred to as “compound (A2)”), and the phosphorus compound has a very high melting point and 13 It has been shown that a flame retardant property can be imparted with a smaller addition amount to a resin having a very high phosphorus element content of .5% by mass and requiring heat kneading at a high temperature.
  • phosphorus compounds containing two 9,10-dihydro-9-oxo-10-phosphaphenanthrene-10-oxide-10-yl groups such as compound (A1) and compound (A2), have a melting point It is high and can be used suitably for high Tg resins such as polycarbonate resins and polyester resins, but the melting point is too high for polyacrylic resins, etc. It was difficult to use for optical materials and the like.
  • Patent Document 6 discloses 9,10-dihydro-9-oxa-10-phenoxy-10-phosphaphenanthrene-10-oxide (hereinafter referred to as “compound (A4) as a flame retardant usable in various transparent resins. ) ”) Is disclosed.
  • the compound (A4) has a relatively small molecular weight and is excellent in thermal stability, since it has only one phosphorus element per molecule, the phosphorus element content is as low as 10% by mass and sufficient flame retardancy. In order to impart the properties, it is necessary to increase the amount of addition, and there is a problem that the heat resistance and mechanical properties of the resin are significantly lowered.
  • JP-A-53-56250 Japanese Patent No. 3897138 Special table 2012-527469 gazette Special table 2013-525276 gazette JP 2010-202718 A JP 2012-12666 A
  • R 1 and R 2 are the same or different and are an alkoxy group having 1 to 4 carbon atoms, a phenoxy group, or a phenyl group.
  • fusing point and phosphorus content are the values measured by the method of description of an Example, and the structure of a compound was also determined by the method of description of an Example.
  • the phosphorus-containing compound used as a flame retardant is represented by the following general formula (1). It is represented by
  • R 1 and R 2 in the formula (1) are the same or different and are a hydrogen atom, hydroxyl group, alkyl group, cycloalkyl group, aryl group, aralkyl group, heteroaryl group, alkenyl group, cycloalkenyl group, alkoxy group.
  • the number of carbon atoms in the cycloalkenyl group is suitably 3 to 15, preferably 4 to 10, more preferably 5 to 7.
  • Examples of the cycloalkenyl group include a 2-cyclopenten-1-yl group and a 2-cyclohexen-1-yl group.
  • Alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, n-butoxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, neo Examples include a pentyloxy group, a tert-pentyloxy group, an n-hexyloxy group, and an isohexyloxy group.
  • the phosphorus-containing compound represented by the general formula (1) includes, for example, a phosphorus compound (DOPO) having a PH group represented by the formula (2) and a formula (3), as shown in Scheme 1.
  • phosphorus compounds containing an alkenyl group having 2 to 4 carbon atoms which is represented (R 1 and R 2, the formula (1) shows the same as) can be obtained by the addition reaction of.
  • a highly transparent resin such as a polycarbonate resin, an amorphous polyester resin, or a polyacrylic resin is particularly preferable.
  • Appearance Test specimens 80 mm ⁇ 10 mm ⁇ 4 mm were prepared by injection molding, and the transparency and the presence or absence of coloring were observed by visual observation ( ⁇ : colorless and transparent, ⁇ : transparent but colored, ⁇ : opaque).
  • the flame-retardant resin composition of the present invention can have a phosphorus content of 1% by mass or more with respect to the resin component, and can impart sufficient flame retardancy. At the same time, it was possible to provide a flame retardant resin composition that substantially maintained the transparency and heat resistance inherent to the amorphous resin.
  • the flame retardant resin composition using the flame retardant B-3 containing a DOPO structure but having a high melting point becomes opaque in a low Tg resin such as PMMA and cannot maintain transparency.
  • the flame retardant resin composition using the resinous flame retardant B-4 having a DOPO structure became opaque without being compatible with PMMA and polycarbonate.
  • the flame-retardant resin composition using the phosphoric ester-type flame retardant B-5 transparency is maintained, but when the phosphorus element content exceeds 1% by mass, Tg rapidly decreases. Since heat resistance fell, it was shown that the compounding quantity of a flame retardant cannot be increased and sufficient flame retardance cannot be provided.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fireproofing Substances (AREA)

Abstract

L'invention aborde le problème consistant à fournir une composition de résine ignifuge qui possède d'excellentes propriétés en termes d'ignifugation et de transparence. La composition de résine ignifuge, avec laquelle ce problème a été résolu, est caractérisée en ce qu'elle comprend un composé de phosphore représenté par la formule générale suivante (1), et un composant à base de résine. (Dans la formule, R1 et R2 sont identiques ou différents et représentent chacun un atome d'hydrogène ou un groupe hydroxy, alkyle, cycloalkyle, aryle, aralkyle, hétéroaryle, alcényle, cycloalcényle, alcoxy, aryloxy, ou acyle, et n est un entier de 2 à 4.)<sp /> <sp />
PCT/JP2016/088179 2016-01-08 2016-12-21 Composition de résine ignifuge WO2017119304A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2017560102A JPWO2017119304A1 (ja) 2016-01-08 2016-12-21 難燃性樹脂組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-002876 2016-01-08
JP2016002876 2016-01-08

Publications (1)

Publication Number Publication Date
WO2017119304A1 true WO2017119304A1 (fr) 2017-07-13

Family

ID=59274275

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/088179 WO2017119304A1 (fr) 2016-01-08 2016-12-21 Composition de résine ignifuge

Country Status (2)

Country Link
JP (1) JPWO2017119304A1 (fr)
WO (1) WO2017119304A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013525276A (ja) * 2010-03-31 2013-06-20 アルベマール・コーポレーシヨン Ｄｏｐｏ由来の化合物およびその組成物の調製のためのプロセス

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013525276A (ja) * 2010-03-31 2013-06-20 アルベマール・コーポレーシヨン Ｄｏｐｏ由来の化合物およびその組成物の調製のためのプロセス

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
TAKAYOSHI HIRAI ET AL.: "Air-induced anti- Markovnikov addition of secondary phosphine oxides and H-phosphinates to alkens", ORGANIC LETTERS, vol. 9, no. 1, 2007, pages 53 - 55, XP002508390 *
YUTA SAGA ET AL.: "A salt-free synthesis of 1,2- bisphosphorylethanes via an efficient PMe3- catalyzed addition of >P(O)H to vinylphosphoryl conmpounds", TETRAHEDRON LETTERS, vol. 56, no. 38, 2015, pages 5303 - 5305, XP029259653 *

Also Published As

Publication number Publication date
JPWO2017119304A1 (ja) 2018-11-08

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