JP2017538011A - 不飽和熱硬化性ポリエステル組成物における低収縮添加剤の相分離を防止するための添加剤 - Google Patents
不飽和熱硬化性ポリエステル組成物における低収縮添加剤の相分離を防止するための添加剤 Download PDFInfo
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- JP2017538011A JP2017538011A JP2017530261A JP2017530261A JP2017538011A JP 2017538011 A JP2017538011 A JP 2017538011A JP 2017530261 A JP2017530261 A JP 2017530261A JP 2017530261 A JP2017530261 A JP 2017530261A JP 2017538011 A JP2017538011 A JP 2017538011A
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Abstract
Description
不飽和モノマーと架橋し、任意選択で繊維または微粒子により強化された不飽和樹脂成型組成物からの、低収縮添加剤の相分離を防止するための、追加の添加剤を開発できることが望ましい。
によって定義することができ、
式中:
R1は、環状、分枝状、または非分枝状のアルキル;アリール;アルキルアリールまたはアリールアルキルであってよいC1〜C36ヒドロカルビル基、望ましくはC1〜C18であり、
δは、3および/または4であり、
xは、10〜60、特に10〜40であり、
yは、0〜10、特に0であり、
−(OC2H4)および−(OCδH2δ)繰り返し単位は、ランダムまたはブロック状などの任意の順序であってよく、yはx未満でなければならず、
Wは、1〜4個の炭素原子、特に1個の炭素原子のヒドロカルビレンを任意選択で含んでいてもよい、エステル、イミド、または任意選択でアミド連結基であり、
Φは、6〜10個、特に6個の炭素原子のアリール基であり、前記アリール基は、1〜4個の炭素原子の直鎖状もしくは分枝状アルキル鎖、ハロゲン化物、および/または−NO2を含んでいてもよい置換基(単数または複数)(ナフタレンに関して最大5個もしくは6個、またはベンゼンに関して最大4個)を任意選択で有していてもよい。
a) アミン系多塩基種の残りの遊離アミノ基の1つもしくは複数と、イソシアネート、ラクトン、無水物、エポキシド、環状カーボネート、もしくは(メタ)アクリレートとの反応;
b) アミン系多塩基種の残りの遊離アミノ基の1つもしくは複数と、モノもしくはポリカルボン酸、鉱酸、リンおよびポリオキソメタレートを含有する酸、もしくは強酸との、塩形成および/もしくは反応;
c) アミン系多塩基種の残りの遊離アミノ基の1つもしくは複数の、酸化窒素への酸化;
d) アミン系多塩基種の残りの遊離アミノ基の1つもしくは複数の4級化;または
e) アミン系多塩基種の残りの遊離アミノ基の1つもしくは複数と、モノアミノ反応性基で終結するMWが150〜3000のポリマーの1つもしくは複数との反応
によって実現することができる。
a) ポリエステルは:
任意選択で、カルボン酸またはエステル官能基を含有する開始剤分子の存在下、ヒドロキシカルボン酸および/またはラクトンの1種もしくは複数;あるいは
任意選択で、カルボン酸またはエステル官能基を含有する開始剤分子の存在下、ジオールの1種または複数と二塩基酸/無水物の1種または複数と
の重合から誘導され;
b) ポリエステルアミドは:
任意選択で、カルボン酸またはエステル官能基を含有する開始剤分子の存在下、ヒドロキシカルボン酸および/またはラクトンの1種もしくは複数と、アミノカルボン酸および/またはラクタムの1種もしくは複数と
の重合から誘導され;
c) ポリアミドは:
任意選択で、カルボン酸またはエステル官能基を含有する開始剤分子の存在下、アミノカルボン酸および/またはラクタムの1種もしくは複数;あるいは任意選択で、カルボン酸またはエステル官能基を含有する開始剤分子の存在下、ジアミンの1種または複数と二塩基酸/無水物の1種または複数と
の重合から誘導される。
i) 2−ヒドロキシエチルアクリレートなどの開始剤分子を直接使用して誘導され;
ii) ヒドロキシ官能基を含有する開始剤分子を使用して、次いで後続の、(メタ)アクリレートエステルとのエステル交換反応から誘導され;
iii) 上述のカルボン酸またはエステル官能基を含有する開始剤分子を使用して、次いで後続の、2−ヒドロキシエチルアクリレートなどのヒドロキシル官能基を含有するまたはグリシジルメタクリレートなどのエポキシ官能基を含有する(メタ)アクリレートエステルとの反応から誘導される。
PAG 1、ポリエーテルアミン、C12〜15アルコールをプロピレンオキシドと反応させ(MW 1660)、その後、得られたポリエーテルアルコールの塩基触媒付加をアクリロニトリル対して行い、引き続き水素化することにより得られたアミン(85%活性)からなる、Lubrizolから入手可能。
PAG 2、ポリエーテルアミン、C12〜15アルコールをブチレンオキシドと反応させ(MW 1700)、その後、得られたポリエーテルアルコールの塩基触媒付加をアクリロニトリルに対して行い、引き続き水素化することにより得られたアミン(80%活性(active)))、Lubrizol製。
1,2,4−ベンゼントリカルボン酸無水物、Sigma Aldrichから入手可能、ポリ(プロピレングリコール)モノブチルエーテル、分子量1000g/mol、Sigma−Aldrichから入手可能。
ホモフタル酸、Sigma Aldrichから入手可能
オルトリン酸触媒、Fisherから入手可能
Surfonamine(商標)B100、分子量1000g/ml、Huntsmanから入手可能
Surfonamine(商標)B−200 分子量2000g/mol、Huntsmanから入手可能
EPOMIN(商標)SP−200 日本触媒から入手可能なMw 10,000g/molのポリエチレンイミン
EPOMIN(商標)SP−018、日本触媒から入手可能なMw 1800g/molのポリエチレンイミン
EPOMIN(商標)SP−006、日本触媒から入手可能なMw 600g/molのポリエチレンイミン
テトラエチレンペンタミン、Sigma Aldrichから入手可能
トリエチレンテトラミン、Sigma Aldrichから入手可能
スチレン、Sigma Aldrichから入手可能
Palapreg(商標)H814−01、スチレン中にポリスチレンを含む低収縮添加剤、DSMから入手可能
Palapreg(商標)P17−02、オルトフタル酸および標準のジオールからの不飽和ポリエステル樹脂、DSMから入手可能
中間体
中間体1
PAG 1、79.91重量部(PAG 1=ポリエーテルアミン、C12〜15アルコールをプロピレンオキシドと反応させ(MW 1660)、その後、得られたポリエーテルアルコールの塩基触媒付加をアクリロニトリル対して行い、引き続き水素化することにより得られたアミン(85%活性)からなる、Lubrizolから入手可能)を、反応フラスコに投入し、撹拌しながら窒素ブランケット下で70℃に加熱する。温度が上昇したら、1,2,4−ベンゼントリカルボン酸無水物(MW 192.13、Sigma Aldrich製、5.72部)をフラスコに投入し、次いで120℃に加熱し、8時間撹拌することにより、褐色の液体が得られる。これが中間体1である。
中間体2
ポリ(プロピレングリコール)モノブチルエーテル(MW 1000、Sigma Aldrich製、75.78部)、ホモフタル酸(MW 180.16、Sigma Aldrich製、13.69部)、およびオルトリン酸触媒(Fisher製、0.27部)を反応フラスコに投入し、窒素ブランケット下で180℃に加熱し、14時間撹拌することにより、褐色の液体の生成物が得られる。これが中間体2である。
中間体3
Surfonamine B100(MW 1000、Huntsman製、91.74部)を反応フラスコに投入し、窒素ブランケット下で70℃に加熱し、次いで1,2,4−ベンゼントリカルボン酸無水物(MW 192.13、Sigma Aldrich製、17.62部)をフラスコに投入し、120℃に加熱し、14時間撹拌することにより、褐色の液体の生成物が得られる。これが中間体3である。
中間体4
PAG 2、94.2部(PAG 2=ポリエーテルアミン、C12〜15アルコールをブチレンオキシドと反応させ(MW 1700)、その後、得られたポリエーテルアルコールの塩基触媒付加をアクリロニトリルに対して行い、引き続き水素化することにより得られたアミン(80%活性)、Lubrizol製)、および1,2,4−ベンゼントリカルボン酸無水物(MW 192.13、Sigma Aldrich製、7.8部)を反応フラスコに投入し、窒素ブランケット下で80℃に加熱し、3時間撹拌し、次いで120℃に加熱し、12時間撹拌し、次いで150℃に加熱し、8時間撹拌することにより、褐色の液体の生成物が得られる。これが中間体4である。
中間体5
Surfonamine B200(MW 2435、Huntsman製、89.32部)を反応フラスコに投入し、窒素ブランケット下で70℃に加熱し、次いで1,2,4−ベンゼントリカルボン酸無水物(MW 192.13、Sigma Aldrich製、7.047部)をフラスコに投入し、120℃に加熱し、11.5時間撹拌し、次いで150℃に4時間加熱することにより、褐色の液体の生成物が得られる。これが中間体5である。
剤(agent)
中間体1(56.29部)を反応フラスコに投入し、窒素下で90℃に加熱し、予熱したEPOMIN SP−018(MW 1800、日本触媒製、3.75部)を投入し、1.5時間撹拌し、次いで120℃に加熱し、1時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤1である。
中間体1(74.22部)を反応フラスコに投入し、窒素下で70℃に加熱し、予熱したEPOMIN SP−200(MW 10,000、日本触媒製、3.17部)を投入し、次いで120℃に加熱し、6時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤2である。
中間体1(64.6部)を反応フラスコに投入し、窒素下70℃に加熱し、予熱したEPOMIN SP−018(MW 1800、日本触媒製、2.48部)を投入し、次いで120℃に加熱し、6時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤3である。
中間体1(64.94部)を反応フラスコに投入し、窒素下で70℃に加熱し、予熱したEPOMIN SP−200(MW 10,000、日本触媒製、2.17部)を投入し、次いで120℃に加熱し、6時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤4である。
中間体1(33.98部)を反応フラスコに投入し、窒素下で70℃に加熱し、予熱したEPOMIN SP−200(MW 10,000、日本触媒製、0.97部)を投入し、次いで120℃に加熱し、6時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤5である。
中間体1(109.98部)を反応フラスコに投入し、窒素下で70℃に加熱し、予熱したEPOMIN SP−200(MW 10,000、日本触媒製、2.75部)を投入し、次いで120℃に加熱し、6時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤6である。
中間体1(52.69部)を反応フラスコに投入し、窒素下で90℃に加熱し、予熱したEPOMIN SP−018(MW 1800、日本触媒製、1.06部)を投入し、1.5時間撹拌し、次いで120℃に加熱し、1時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤7である。
中間体1(73.44部)を反応フラスコに投入し、窒素下で90℃に加熱し、予熱したテトラエチレンペンタミン(MW 189.30、Sigma Aldrich製、2.82部)を投入し、1.5時間撹拌し、次いで120℃に加熱し、1時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤8である。
中間体1(37.46部)を反応フラスコに投入し、窒素下で90℃に加熱し、予熱したトリエチレンテトラミン(MW 146.23、Sigma Aldrich製、1.44部)を投入し、1.5時間撹拌し、次いで120℃に加熱し、1時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤9である。
中間体1(20.76部)を反応フラスコに投入し、窒素下で90℃に加熱し、予熱したEPOMIN SP−006(MW 600、日本触媒製、0.8部)を投入し、1.5時間撹拌し、次いで120℃に加熱し、1時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤10である。
中間体2(42.75部)を反応フラスコに投入し、窒素下で70℃に加熱し、予熱したEPOMIN SP−200(MW 10,000、日本触媒製、2.51部)を投入し、次いで120℃に加熱し、6時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤11である。
中間体3(66.78部)を反応フラスコに投入し、窒素下で90℃に加熱し、予熱したEPOMIN SP−018(MW 1800、日本触媒製、2.56部)を投入し、1.5時間撹拌し、次いで120℃に加熱し、1時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤12である。
中間体4(40.52部)を反応フラスコに投入し、窒素下で70℃に加熱し、予熱したEPOMIN SP−200(MW 10,000、日本触媒製、1.35部)を投入し、次いで120℃に加熱し、6時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤13である。
中間体5(47.27部)を反応フラスコに投入し、窒素下で90℃に加熱し、予熱したEPOMIN SP−018(MW 1800、日本触媒製、1.82部)を投入し、1.5時間撹拌し、次いで120℃に加熱し、1時間撹拌することにより、褐色の粘性液体生成物が得られる。これが剤14である。
樹脂分離試験
Claims (15)
- 不飽和樹脂成型組成物であって、
相分離を防止する添加剤と、
50,000g/molよりも高い数平均分子量を有し、および前記組成物中に分散された相として存在すると特徴付けられる、低収縮用の付加重合ポリマー(D)と、
ラジカル共重合性不飽和樹脂と、
重合性不飽和モノマーと
を含み、
相分離を防止する前記添加剤が、式:
R1−(OCδH2δ)x−(OCH2CH2)y−W−Φ−COOH
の官能化ポリエーテルと、分子当たり少なくとも3個の第1級および/または第2級アミン基を有し100から100,000g/molの数平均分子量を有するアミン系多塩基種との反応生成物を含み、前記R1−(OCδH2δ)x−(OCH2CH2)y−W−Φ−COOH:アミン系多塩基種の重量比が10:1から60:1であり、
式中、
R1は、環状、分枝状、または非分枝状のアルキル;アリール;アルキルアリールまたはアリールアルキルであってよいC1〜C36ヒドロカルビル基であり、
δは、3および/または4であり、
xは、10〜60であり、
yは、0〜10であり、
−(OCδH2δ)および−(OCH2CH2)繰り返し単位は、ランダムまたはブロック状などの任意の順序であってよく、yはx未満でなければならず、
Wは、1〜4個の炭素原子、特に1個の炭素原子のヒドロカルビレンを任意選択で含んでいてもよい、エステル、イミド、または任意選択でアミド連結基であり、
Φは、6〜10個の炭素原子のアリール基であり、前記アリール基は、1〜4個の炭素原子の直鎖状もしくは分枝状アルキル鎖、ハロゲン化物、および/または−NO2を含む置換基(単数または複数)を任意選択で有していてもよい、
不飽和樹脂成型組成物。 - 前記R1−(OCδH2δ)x−(OCH2CH2)y−W−Φ−COOH対前記アミン系多塩基種の前記重量比が、15:1から50:1である、請求項1に記載の不飽和樹脂組成物。
- 前記アミン系多塩基種が、約140から約75,000g/molの数平均分子量を有する、請求項1または2に記載の不飽和樹脂組成物。
- xが10から40である、前記請求項のいずれかに記載の不飽和樹脂組成物。
- Wがエステル連結を含む、請求項1から4のいずれかに記載の不飽和樹脂組成物。
- Wがイミド連結を含む、請求項1から4のいずれかに記載の不飽和樹脂組成物。
- 前記アミン系多塩基種が、約140から約20,000g/molの数平均分子量を有する、前記請求項のいずれかに記載の不飽和樹脂組成物。
- 前記ラジカル共重合性不飽和樹脂が、不飽和ポリエステルまたはビニルエステル樹脂である、前記請求項のいずれかに記載の不飽和樹脂組成物。
- 前記低収縮添加剤が、スチレンホモポリマー、またはスチレンモノマーから誘導された少なくとも33wt%の繰り返し単位を有するコポリマーである、前記請求項のいずれかに記載の不飽和樹脂組成物。
- 前記アミン系多塩基種が、ポリエチレンイミンである、前記請求項のいずれかに記載の不飽和樹脂組成物。
- ラジカル共重合性不飽和樹脂:重合性不飽和モノマーの重量比が、30〜90:10〜70である、前記請求項のいずれかに記載の不飽和樹脂組成物。
- 前記組成物が、前記不飽和樹脂成型組成物の全重量に対して、少なくとも3wt%の細断された、織られた、または巻かれた繊維をさらに含む、前記請求項のいずれかに記載の不飽和樹脂組成物。
- 前記請求項のいずれかに記載の不飽和樹脂組成物を含む、前記不飽和モノマーが重合され前記不飽和樹脂が架橋された、成型後の成型物品。
- 相分離を防止する前記添加剤の量が、前記不飽和樹脂および不飽和モノマーの総量100重量部に対して約0.5から約5重量部の範囲内にある、請求項1から12のいずれかに記載の不飽和樹脂組成物。
- 式
R1−(OCδH2δ)x−(OCH2CH2)y−W−Φ−COOH
の官能化ポリエーテルとアミン系多塩基種との反応生成物である、相分離を防止する前記添加剤が、モノもしくはポリカルボン酸、鉱酸、リンおよびポリオキソメタレートを含有する酸または強酸の群から選択される酸種との塩形成反応によってさらに官能化されるの1つまたは複数の未反応のアミノ基を含む、請求項1から12および14のいずれかに記載の不飽和樹脂組成物。
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TW201638189A (zh) | 2016-11-01 |
KR20170092681A (ko) | 2017-08-11 |
WO2016094026A1 (en) | 2016-06-16 |
ES2785558T3 (es) | 2020-10-07 |
EP3230037B1 (en) | 2020-04-08 |
TWI684620B (zh) | 2020-02-11 |
EP3230037A1 (en) | 2017-10-18 |
CN107207849A (zh) | 2017-09-26 |
JP6822956B2 (ja) | 2021-01-27 |
CN107207849B (zh) | 2020-05-12 |
US20180265696A1 (en) | 2018-09-20 |
KR102400084B1 (ko) | 2022-05-18 |
US10246584B2 (en) | 2019-04-02 |
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