JP2021534310A - 芳香族アミド分散剤 - Google Patents
芳香族アミド分散剤 Download PDFInfo
- Publication number
- JP2021534310A JP2021534310A JP2021509978A JP2021509978A JP2021534310A JP 2021534310 A JP2021534310 A JP 2021534310A JP 2021509978 A JP2021509978 A JP 2021509978A JP 2021509978 A JP2021509978 A JP 2021509978A JP 2021534310 A JP2021534310 A JP 2021534310A
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- JP
- Japan
- Prior art keywords
- acid
- dispersant
- group
- functionalized
- acrylate
- 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
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 113
- 150000008430 aromatic amides Chemical class 0.000 title abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 229920000642 polymer Polymers 0.000 claims abstract description 55
- 239000007787 solid Substances 0.000 claims abstract description 55
- 125000003118 aryl group Chemical group 0.000 claims abstract description 40
- 150000003511 tertiary amides Chemical class 0.000 claims abstract description 18
- 150000001408 amides Chemical class 0.000 claims abstract description 16
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 11
- -1 NH 2 Inorganic materials 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 229920000570 polyether Polymers 0.000 claims description 36
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 33
- 239000000049 pigment Substances 0.000 claims description 32
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 239000002609 medium Substances 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 150000008064 anhydrides Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000003973 paint Substances 0.000 claims description 21
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- 238000000034 method Methods 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
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- 125000005842 heteroatom Chemical group 0.000 claims description 12
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
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- 239000001257 hydrogen Substances 0.000 claims description 9
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 238000007142 ring opening reaction Methods 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 3
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims description 2
- 238000006845 Michael addition reaction Methods 0.000 claims 1
- 238000007306 functionalization reaction Methods 0.000 claims 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 claims 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 claims 1
- 239000000976 ink Substances 0.000 abstract description 40
- 238000000576 coating method Methods 0.000 abstract description 26
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- 125000000542 sulfonic acid group Chemical group 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 description 46
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 33
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- 239000011347 resin Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
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- 239000006185 dispersion Substances 0.000 description 16
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- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical class O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 6
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Abstract
Description
R’はH、またはC1〜50で任意に置換されたヒドロカルビル基もしくはC1〜50で任意に置換されたヒドロカルボニルであり、
YはC2〜4−アルキレンオキシであり、
xは2〜90であり、
qは1または2である。
米国特許公開第2015/112020号は、以下の構造によって表される顔料分散剤のためのアンカーとしての縮合芳香族イミドペンダント基の使用について記載しており、
以下の構造を有する分散剤ポリマーを含む分散剤であり、
R2がH、またはC1〜50で任意に置換されたヒドロカルビルまたはC1〜50で任意に置換されたヒドロカルボニル基であり、
Gがエーテル、エステル、アルデヒド、ケトン、アミド、ウレタン、アルコール、もしくはカルボン酸基として表されるOもしくはNなどのヘテロ原子で任意に置換されたC1〜50ヒドロカルビル基、または任意に置換されたアルキル(メタ)アクリレートもしくは(メタ)アクリルアミドの残留物(指定された反応種の化学反応の予想される反応および/または重合生成物)、または以下の式のエポキシドの開環生成物であり、
R3が線状または分枝状C1〜50、好ましくはC1〜20アルキル基であり、
Tが−C(O)−CH(R4)CH2またはC1〜5ヒドロカルビル鎖であり、
GがC1〜50ヒドロカルビルである場合、Tは−C(O)−CH(R4)CH2であり、
Gがアクリレートまたはエポキシドの残留物(指定された反応種の化学反応の予想される反応および/または重合生成物)である場合、TはC1〜5ヒドロカルビル鎖であり、
R4がHまたはMe、好ましくはHであり、
Yが独立して、各繰り返し単位でC2〜4アルキレンオキシであり、
Qが1つ以上の芳香環を含み、R1で置換され(最大3つまたは4つの環)、2つの芳香環が存在する場合に任意に縮合されているヒドロカルビレン基であり、Qに結合したカルボン酸基がQの芳香環の炭素原子に結合しており、
式中の任意の酸の水素を金属、アミン、またはアンモニウムカチオンによって置き換えて、分散剤を塩の形態にすることができ、
xが2〜90である。
一実施形態では、Qは、アミド連結を有するベンゼン環に基づくことができる。1つの好ましい実施形態では、Qは、1,2,4−ベンゼントリカルボン酸無水物から誘導される。Qに結合しているカルボン酸またはスルホン酸基は、Qの芳香環炭素に結合している。
R1が独立して、CO2HまたはSO3Hであり、aが1〜2または3であり、
R2がH、またはC1〜50で任意に置換されたヒドロカルビルまたはC1〜50で任意に置換されたヒドロカルボニル基であり、
Gがエーテル、エステル、アルデヒド、ケトン、アミド、ウレタン、アルコール、もしくはカルボン酸基として提示される/表されるOもしくはNなどのヘテロ原子で任意に置換されたC1〜50ヒドロカルビル基、または任意に置換されたアルキル(メタ)アクリレートもしくは(メタ)アクリルアミドの残留物(指定された反応種の化学反応の予想される反応および/または重合生成物)、または以下の式のエポキシドの開環生成物であり、
R3が線状または分枝状C1〜50、好ましくはC1〜20アルキル基であり、
Tが−C(O)−CH(R4)CH2またはC1〜5ヒドロカルビル鎖であり、
GがC1〜50ヒドロカルビルである場合、Tは−C(O)−CH(R4)CH2であり、
Gがアクリレートまたはエポキシドの残留物(指定された反応種の化学反応の予想される反応および/または重合生成物)である場合、TはC1〜5ヒドロカルビル鎖であり、
R4がHまたはMe、好ましくはHであり、
Yが独立して、各繰り返し単位でC2〜4アルキレンオキシであり、
Qが1つ以上の芳香環を含み、R1で置換され(最大3つまたは4つの環)、2つの芳香環が存在する場合に任意に縮合されているヒドロカルビレン基であり、Qに結合したカルボン酸基がQの芳香環の炭素原子に結合しており、
式中の任意の酸の水素を金属、アミン、またはアンモニウムカチオンによって置き換えて、分散剤を塩の形態にすることができ、
xが2〜90である。
一実施形態では、Qは、アミド連結を有するベンゼン環に基づくことができる。1つの好ましい実施形態では、Qは、1,2,4−ベンゼントリカルボン酸無水物から誘導されたベンゼン環である。Qに結合しているカルボン酸基および任意のスルホン酸基は、Qの芳香環の炭素原子に結合している。
実施形態1では、ポリエーテルアミンは、マイケル反応を介して(メタ)アクリレート(任意に置換されている)と反応して、二級アミンを作成し、次いで二級アミンは酸官能化芳香族無水物と反応する。これは、式IIa、IIb、IIc、IIIa、IIIb、IVa、およびIVbでカバーされている。
0〜60重量%のプロピレンオキシド、および40〜100重量%のエチレンオキシド、または
0〜50重量%のプロピレンオキシド、および50〜100重量%のエチレンオキシド、または
0〜30重量%のプロピレンオキシド、および70〜100重量%のエチレンオキシド、または
0〜20重量%のプロピレンオキシド、および80〜100重量%のエチレンオキシド、または
0〜15重量%のプロピレンオキシド、および85〜100重量%のエチレンオキシド。
0〜60重量%のエチレンオキシド、および40〜100重量%のプロピレンオキシド、または
0〜50重量%のエチレンオキシド、および50〜100重量%のプロピレンオキシド、または
0〜30重量%のエチレンオキシド、および70〜100重量%のプロピレンオキシド、または
0〜20重量%のエチレンオキシド、および80〜100重量%のプロピレンオキシド、または
0〜15重量%のエチレンオキシド、および85〜100重量%のプロピレンオキシド。
実施形態2では、ポリアルキレングリコール(メタ)アクリレートは一級アミンと反応し、次いで酸官能化芳香族無水物と反応する。一級アミン反応物は、エチレンオキシド、プロピレンオキシド、ブチレンオキシド、およびスチレンオキシドなどのアルキレンオキシド単位を含有する、100〜10000、より望ましくは400〜2500の数平均分子量を有するポリエーテルアミンであり得るか、あるいは、一級アミンは、1〜50個、より望ましくは1〜20個の炭素原子を有するヒドロカルビルまたはヒドロカルボニル基を含有し、1個もしくは2個(より望ましくは、1個のみ)の一級アミンおよび最大1個もしくは2個の二級アミン、またはアミド連結などの他の窒素含有基を含有する、線状、分枝状、環状、さらには芳香族などの低分子量の非ポリマーアミンであり得る。望ましくは、一級アミン反応物は、一級アミン分子あたり、酸素、窒素、および任意に硫黄の各々最大4個のヘテロ原子の量で、酸素および窒素(および任意に硫黄)などの他のヘテロ原子を含有し得る。1つの好ましい実施形態では、一級アミンは、前述のSurfonamine(登録商標)ポリエーテルアミンなどのポリエーテルアミンである。別の好ましい実施形態では、一級アミンは、一級アミンの窒素以外のヘテロ原子を含まないアルキルアミンである。別の好ましい実施形態では、一級アミンは、C1〜20を含有するアミノカルボン酸であり、酸素および窒素(および任意に硫黄)などの他のヘテロ原子を含有し得る。別の好ましい実施形態では、一級アミンは、C1〜20を含有するアミノアルコールであり、酸素および窒素(および任意に硫黄)などの他のヘテロ原子を含有し得る。別の好ましい実施形態では、一級アミンは、C1〜20を含有する芳香族アミンであり、酸素および窒素(および任意に硫黄)などの他のヘテロ原子を含有し得る。
一例は、ブチルアミンとポリ(エチレングリコール)(メタ)アクリレートMn1000との反応、それに続く酸官能化芳香族無水物との反応である。
実施形態3では、ポリアルキレングリコール(メタ)アクリレートは、ポリエーテルアミンと反応し、次いで酸官能化芳香族無水物と反応する。
例は、Surfonamine(登録商標)L100とポリ(エチレングリコール)アクリレートMn350との反応、次いでトリカルボン酸ベンゼン無水物との反応であろう。
実施形態4では、ポリエーテルアミンは、エポキシド(以前に定義されたように)と反応して、二級アミンを作成し、次いでこれは、酸官能化芳香族無水物と反応する。例は、Surfonamine(登録商標)L207と1,2−エポキシ−3−フェノキシプロパンとの反応、次いでトリカルボン酸ベンゼン無水物との反応であろう。
本組成物中に存在する粒子状固体は、考慮される温度で有機媒体に実質的に不溶性、および/または水に不溶性であり、それらの中で微細な分割形態で安定化することが所望される任意の無機または有機固体材料であり得る。粒子状固体は、粒状材料、繊維、小板の形態、または粉末の形態、多くの場合、吹き付けられた粉末の形態であり得る。一実施形態では、粒子状固体は、顔料である。
(a)0.5〜80部の粒子状固体と、
(b)0.1〜79.6部の式Iのポリマーと、
(c)19.9〜99.4部の有機液体および/または水と、を含み、ここで、すべての相対部は重量であり、量は(a)+(b)+(c)=100である。
XJT−507をSurfonamine(登録商標)L207に置き換えたことを除いて、米国特許公開2005/0120911の実施例1に従って分散剤を調製した。1,2,4−ベンゼントリカルボン酸無水物(14.4部)およびポリエーテルアミン(150.0部、Surfonamine(登録商標)L207、MW:2000、Huntsman社製)を、IR分光法によって決定される場合、無水物がなくなるまで、120℃で1時間、次いで160℃で4時間、窒素雰囲気下で撹拌した。最終生成物は、27.4mgKOH/gの酸価および1714.9cm−1のイミドピークを有した。
実施例1(EX1)−2−カルボキシエチルアクリレート、次いで1,2,4−ベンゼントリカルボン酸無水物と反応させたポリエーテルアミン。
分散剤を、分散剤CE1およびEX1(0.68部)を水(10.43部)に溶解することによって調製した。これに、消泡剤(0.14部、BYK(登録商標)024、BYK−Chemie、Altana Group社製)、3mmのガラスビーズ(120部)、および白色顔料(33.75部、Kronos(登録商標)2360、Kronos社製)を添加し、内容物をScandexシェーカー上で1時間粉砕した。EX1を使用して得られた分散剤は流体ミルベースを生成し、CE1はゲルを生成した。
XJT−507をSurfonamine(登録商標)L100に置き換えたことを除いて、米国特許公開2005/0120911の実施例1に従って分散剤を調製した。1,2,4−ベンゼントリカルボン酸無水物(11.85部)およびポリエーテルアミン(64.77部、Surfonamine(登録商標)L100、MW:1000、Huntsman社製)を、IR分光法によって決定される場合、無水物がなくなるまで、110℃で1時間、次いで170℃で5時間、窒素雰囲気下で撹拌した。最終生成物は、48.16mgKOH/gの酸価および1713cm−1のイミドピークを有した。
ポリエーテルアミン(85.91部、Surfonamine(登録商標)L207、MW:2000、Huntsman社製)およびフェノチアジン(0.026部)を空気雰囲気下、50℃で撹拌した。この混合物に、アクリル酸(3.07部)を添加し、反応温度を80℃に増加し、1H NMR分光法によって決定される場合、ビニルピークが存在しなくなるまで、混合物を5.5時間攪拌した。次いで温度を50℃に低減した後、1,2,4−ベンゼントリカルボン酸無水物(8.19部)を窒素雰囲気下で添加した。無水物が溶解するまで反応混合物を24時間撹拌し、IR分光法によって決定すると無水物のピークは残っていなかった。最終生成物は74.40mgKOH/gの酸価を有し、IR分光法は1637cm−1に三級アミドカルボニルピークを示した。
ポリエーテルアミン(212.93部、Surfonamine(登録商標)L100、MW:1000、Huntsman社製)および3,5−ジ−tert−ブチル−4−ブチルヒドロキシトルエン(0.84部)を空気雰囲気下、50℃で撹拌した。この混合物に、2−カルボキシエチルアクリレート(28.85部)を50分かけて滴下し、1H NMR分光法によって決定される場合、ビニルピークが存在しなくなるまで、50℃で30分、次いで80℃で3時間放置した。次いで温度を50℃に低減した後、1,2,4−ベンゼントリカルボン酸無水物(39.11部)を窒素雰囲気下で添加した。無水物が完全に溶解するまで反応混合物を撹拌し、次いでIR分光法によって決定される場合、無水物のピークがなくなるまで、それをさらに10時間加熱した。最終生成物は117.71mgKOH/gの酸価を有し、IR分光法は1633cm−1に三級アミドカルボニルピークを示した。
ポリエーテルアミン(101.64部、Surfonamine(登録商標)L100、MW:1000、Huntsman社製)および3,5−ジ−tert−ブチル−4−ブチルヒドロキシトルエン(0.36部)を空気雰囲気下、50℃で撹拌した。この混合物に、1,2−エポキシ−3−フェノキシプロパン(15.17部)を10分かけて滴下し、50℃で30分間撹拌したままにした。IRまたは1H NMR分光法によって決定される場合、エポキシドピークが存在しなくなるまで、反応混合物を50℃でさらに18時間撹拌した。このとき、1,2,4−ベンゼントリカルボン酸無水物(19.47部)を窒素雰囲気下で添加した。無水物が完全に溶解するまで反応混合物を撹拌し、次いでIR分光法によって決定される場合、無水物がなくなるまで、さらに10時間攪拌した。最終生成物は81.79mgKOH/gの酸価を有し、IR分光法は1665cm−1に三級アミドカルボニルピークを示した。
分散剤の比較例(CE−1およびCE−2)および実施例(EX1〜4)(0.15部)を水(3.32部)に溶解することによって、分散剤を調製した。これに、(0.03部、BYK(登録商標)024、BYK−Chemie、Altana Group社製)、3mmのガラスビーズ(17部)、および白色顔料(6.50部、Kronos(登録商標)2360、Kronos社製)を添加し、内容物を水平シェーカー上で16時間粉砕した。次いで、得られた分散剤の流動性を評価した。
分散剤の比較例(CE−1およびCE−2)および実施例(EX1〜3)(0.15部)を酢酸1−メトキシ−2−プロピル(2.35部)に溶解することによって、分散剤を調製した。これに、3mmのガラスビーズ(17部)、白色顔料(7.50部、Kronos(登録商標)2360、Kronos社製)を添加し、内容物を水平シェーカーで16時間粉砕した。得られた分散剤の粒径(D50およびD90)を、Microtrac DLS Nanoフレックス粒径分析装置によって決定した。
Claims (19)
- 以下の構造を有する分散剤ポリマーを含む分散剤またはその塩であって、
R2がH、またはC1〜50の必要に応じて置換されたヒドロカルビルまたはC1〜50の必要に応じて置換されたヒドロカルボニル基であり、
Tが−C(O)−CH(R4)CH2またはC1〜5ヒドロカルビル鎖であり、
GがC1〜50ヒドロカルビルである場合、Tは−C(O)−CH(R4)CH2であり、
Gがマイケル付加反応で窒素と反応したアクリレートまたは開環エポキシ重合によって開環したエポキシドの残留物の場合、TはC1〜5ヒドロカルビル鎖であり、
R4がHまたはMe、好ましくはHであり、
Gがエーテル、エステル、アルデヒド、ケトン、アミド、ウレタン、アルコール、もしくはカルボン酸基として表されるOもしくはNなどのヘテロ原子で必要に応じて置換されたC1〜50ヒドロカルビル基、または必要に応じて置換されたアルキル(メタ)アクリレートもしくは(メタ)アクリルアミドの残留物、または次式のエポキシドの開環生成物であり、
R3が線状または分枝状C1〜50、好ましくはC1〜20アルキル基であり、
各繰り返し単位におけるYが独立して、C2〜4アルキレンオキシであり、
Qが、必要に応じてR1で置換された1つ以上の芳香環を含み(最大3つまたは4つの環)、2つの芳香環が存在する場合に必要に応じて縮合されているヒドロカルビレン基であり、Qに結合したカルボン酸基が前記Qの芳香環の炭素原子に結合しており、
前記式中の任意の酸の水素を金属、アミン、またはアンモニウムカチオンによって置き換えて、前記分散剤を塩の形態にすることができ、
xが2〜90である、分散剤またはその塩。 - Qがナフタレンを含み、より望ましくはQが酸官能化(例えば、カルボン酸またはスルホン酸)1,2−ナフタレン酸アミド、酸官能化2,3−ナフタレン酸アミド、もしくは酸官能化1,8−ナフタレン酸アミド、またはそれらの混合物に由来するナフタレンを含む、請求項1に記載の分散剤。
- Qが、ビフェニルを含む、請求項1に記載の分散剤。
- Qが、フェニルを含む、請求項1に記載の分散剤。
- ステップ(1):(メタ)アクリレートまたは官能化(メタ)アクリレートなどのマイケルアクセプターを、ポリエーテルアミンなどの求核性ポリマー鎖の窒素原子と反応させて、ポリエーテル官能化二級アミンを形成することであって、前記(メタ)アクリレートまたは官能化(メタ)アクリレートが、以下を含むことができ、
UがOまたはNHであり、
x1が1〜50、より望ましくは1〜20である、形成することと、
ステップ(2):前記ポリエーテル官能化二級アミンを、酸官能化(例えば、カルボン酸またはスルホン酸)芳香族二酸またはその無水物、例えば、酸官能化2,3−ナフタル酸無水物、もしくは例えば1,2,4−ベンゼントリカルボン酸無水物と反応させて、前記芳香族酸と前記ポリエーテルとの間に三級アミド連結基を形成することと、を含むプロセスによって得られる/得ることが可能である、先行請求項1〜4のいずれかに記載の分散剤。 - 前記第1のステップが約0℃〜150℃、より望ましくは約30℃〜80℃の温度で行われ、三級アミドを形成するための前記反応の前記第2のステップが約50℃〜120℃、より優先的には約30℃〜80℃の温度で実施される、請求項5に記載の分散剤。
- ステップ(1):MPEGアクリレートなどの不飽和アクリレート官能基を有する(メタ)アクリレートまたは官能化(メタ)アクリレートモノマーを、求核性脂肪族アミンと反応させて、MPEG官能化二級アミンを形成することと、
ステップ(2):ステップ(1)からの前記MPEG官能化二級アミンを、酸官能化芳香族二酸またはその無水物、例えば、酸(例えば、カルボン酸またはスルホン酸)官能化2,3−ナフタル酸無水物、もしくは例えば1,2,4−ベンゼントリカルボン酸無水物と反応させて、前記二酸またはその無水物の酸基のうちの1つから三級アミド連結を形成し、前記MPEGを前記芳香族二酸に接続すること(ここで酸/アミドになる)、を含むプロセスによって得られる/得ることが可能であり、前記第1のステップである前記マイケル反応が、約0℃〜150℃、より望ましくは約30℃〜80℃の温度で実施することができ、前記三級アミドを形成するための前記反応の前記第2のステップが、約0℃〜120℃、より望ましくは約30℃〜80℃のアミド化のための温度で実施される、先行請求項1〜4のいずれかに記載の分散剤。 - ステップ(1):ヒドロキシエチルアクリレート(必要に応じて、エトキシル化されているか、またはヒドロキシル基からのエステル重合を有する)などのヒドロキシルアクリレートを求核性脂肪族アミンと反応させて、脂肪族二級アミンを形成することと、
ステップ(2):前記脂肪族二級アミンを酸官能化芳香族二酸または四酸またはその無水物と反応させて、三級アミドを形成することと、
ステップ(3):必要に応じて、前記脂肪族二級アミドの前記ヒドロキシルをエポキシドまたは環状エステル(前記環状エステルは、必要に応じてカプロラクトンである)と反応させ、かつ/または前記エポキシドもしくは環状エステルを重合して、ポリマーポリエーテル鎖またはポリエステル鎖を形成することと、を含むプロセスによって得られる/得ることが可能であり、前記第1のステップ、すなわち前記マイケル反応が、約0℃〜150℃、より望ましくは約30℃〜80℃の温度で実施することができ、前記三級アミドを形成するための前記反応の前記第2のステップが、約50℃〜120℃、より望ましくは約30℃〜80℃の温度で実施され、前記エポキシドまたは環状エステルを重合する前記第3のステップが、約100℃〜200℃の温度で実施される、先行請求項1〜4のいずれかに記載の分散剤。 - 粒子状固体(典型的には、顔料または充填剤)、水性媒体または極性有機溶媒媒体、および少なくともを有するポリマー鎖を含む組成物であって、前記ポリマーが、先行請求項1〜12のいずれかに記載のポリマーによって表される、組成物。
- 前記媒体が、水性媒体を含む、請求項13に記載の組成物。
- 前記媒体が、極性有機媒体を含む、請求項13に記載の組成物。
- 前記組成物が、ミルベース、塗料、またはインクである、請求項13、14、または15に記載の組成物。
- 前記粒子状固体が、顔料または充填剤である、先行請求項13〜16のいずれかに記載の組成物。
- 結合剤をさらに含む、先行請求項13〜17のいずれかに記載の組成物。
- 前記分散剤が、総組成物重量に基づいて、0.1重量%〜79.6重量%、または0.5重量%〜30重量%、または1重量%〜25重量%の範囲の量で存在する、先行請求項13〜18のいずれかに記載の組成物。
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