JP2011511142A - 湿潤分散剤 - Google Patents
湿潤分散剤 Download PDFInfo
- Publication number
- JP2011511142A JP2011511142A JP2010545394A JP2010545394A JP2011511142A JP 2011511142 A JP2011511142 A JP 2011511142A JP 2010545394 A JP2010545394 A JP 2010545394A JP 2010545394 A JP2010545394 A JP 2010545394A JP 2011511142 A JP2011511142 A JP 2011511142A
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- Prior art keywords
- component
- water
- acid
- mixture
- aliphatic
- Prior art date
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- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/044—Suspensions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
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Abstract
Description
I 少なくとも一つのエチレン性不飽和、フェニル基含有モノマーと少なくとも一つの好ましくは脂肪族のα,β−不飽和モノカルボン酸および/または少なくとも一つの好ましくは脂肪族のα,β−不飽和ジカルボン酸の、および場合によってはそれらの誘導体の重合単位を含む、少なくとも50%塩化されたコポリマー10重量%から80重量%と、
II 末端OH末端基を含有し、少なくとも25重量%まではエチレンオキシド単位から合成される少なくとも一つの水溶性、線状、好ましくは脂肪族のポリエーテル1重量%から30重量%と、
III 400g/molから1000g/molの数平均分子量を好ましくは有する脂肪族ジカルボン酸の、および≦2000g/molの数平均分子量を好ましくは有する成分IIの少なくとも一つの水溶性ポリエーテルの、または≦2000g/molの数平均分子量を好ましくは有する成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、少なくとも一つのエステル化生成物5重量%から80重量%と、
IV ≦2000g/molの数平均分子量を好ましくは有する成分IIの少なくとも一つの水溶性ポリエーテルで、または≦2000g/molの数平均分子量を好ましくは有する成分IIの少なくとも一つの水溶性ポリエーテルを含有するポリエーテルの混合物で、3個から5個のカルボキシル基を含有し、500g/molから1500g/molの分子量を好ましくは有する少なくとも一つの脂肪族カルボン酸をエステル化することによって得ることができる、少なくとも一つのスターポリマー3重量%から80重量%とから構成される低VOC混合物を含み、成分I−IVの重量%は、それぞれの場合、成分I−IVの総重量に基づき、ならびに、成分IからIVの重量%の合計は、常に100重量%である必要がある。
そのプロセスとは、例えばPolym.Int.2000,49.993.Aust.J.Chem.2005,58,379、J.Polym.Sci.Part A:Polym.Chem.2005,43,5347、米国特許第6,291,620号、国際公開第98/01478号、国際公開第98/58974号、および国際公開第99/31144号に記載されているような、可逆的付加フラグメント化連鎖移動プロセス(RAFT)(このプロセスは、一定の重合調節剤が使用されるとき、MADIXおよび付加フラグメント化連鎖移動と呼ばれることもあり、この状況ではRAFTとして特定される)である。
また、例えばChem.Rev.2001,101,3661に開示されているような、重合調節剤(NMP)としてニトロキシル化合物を用いる制御された重合も、挙げられる。
場合によっては水素化されていることがある、二量体化脂肪酸。これは、当業者にはダイマー酸としても公知である。これらのダイマー酸は、好ましくは、12から22個のC原子を有する不飽和脂肪酸のオリゴマー化によって、好ましくは、オレイン酸、リノレイン酸および/またはエルカ酸のオリゴマー化によって、得ることができる。36個以下のC原子の炭素鎖を有する二量体化脂肪酸、すなわちダイマー酸が好ましい。
環式、脂肪族、場合によっては不飽和の無水ジカルボン酸と脂肪族ジオールまたはジアミンとの、好ましくは2:1の比率での、反応生成物。これに関連して、好ましくは、環式無水ジカルボン酸、例えば無水マレイン酸または無水コハク酸を使用することができる。
場合によっては水素化されていることがある、三量体化脂肪酸。これは、当業者にはトリマー酸としても公知である。54個以下のC原子の炭素鎖を有する三量体化脂肪酸が好ましい。
環式、脂肪族、場合によっては不飽和の無水ジカルボン酸と、合計3から5個のOH基を有する脂肪族ポリオールまたは3から5個の1級および2級アミノ基を有するポリアミンとの、一個の無水物官能基に対して一個のアミノ基という化学量論比での反応生成物。これに関連して使用することができる環式無水カルボン酸としては、好ましくは、無水マレイン酸または無水コハク酸が挙げられる。
(ポリマー1: 2:1のスチレン対MAn比を有する交互SMA樹脂)
27.3gの酢酸メトキシプロピル、4.2gの2,4−ジフェニル−4−メチル−1−ペンテン、および3.3gのスチレンを140℃に加熱する。反応温度に達したとき、21.7gの酢酸メトキシプロピルに部分的に溶解した14.4gの無水マレイン酸および2.3gのAMBNを100分より長い間計量し、ならびに26.8gのスチレンを85分より長い間計量する。
残留2,4−ジフェニル−4−メチル−1−ペンテン含量:0.1%
Mn:2775g/mol
11.3gの酢酸メトキシプロピル、5.8gの2,4−ジフェニル−4−メチル−1−ペンテンを140℃に加熱する。反応温度に達したら、38.1gの酢酸メトキシプロピルに部分的に溶解した20.4gの無水マレイン酸および2.8gのAMBNを100分より長い間計量し、ならびに21.6gのスチレンを100分より長い間計量する。
残留2,4−ジフェニル−4−メチル−1−ペンテン含量:0.1%
Mn:1886g/mol
27.3gの酢酸メトキシプロピルおよび4.2gの2,4−ジフェニル−4−メチル−1−ペンテンを140℃に加熱する。反応温度に達したら、21.7gの酢酸メトキシプロピルに部分的に溶解した14.4gの無水マレイン酸および2.3gのAMBNを100分より長い間計量し、ならびに26.8gのスチレンを85分より長い間計量する。15分の後続反応時間の後、10gの酢酸メトキシプロピルに部分的に溶解した1gのAMBN、および10gのスチレンを100分より長い間計量する。
残留2,4−ジフェニル−4−メチル−1−ペンテン含量:0.08%
Mn:3156g/mol
22.8gの酢酸メトキシプロピル、13.8gのBlocBuilder、および31.2gのスチレンを120℃に加熱する。反応温度に達したら、7.6gの酢酸メトキシプロピルに部分的に溶解した24.7gのアクリル酸を100分より長い間計量する。2時間の後続反応時間の後、そのポリマー溶液を室温に冷却する。
Mn:2835g/mol
(ポリマー溶液1)
酢酸メトキシプロピル中のポリマー1の溶液100gを10.7gのNaOHおよび91.05gの水と混合し、100℃に加熱して、その酢酸メトキシプロピルを共沸物として蒸留除去する。
酢酸メトキシプロピル中のポリマー2の溶液100gを23.6gのKOHおよび110.4gの水と混合し、100℃に加熱して、その酢酸メトキシプロピルを共沸物として蒸留除去する。
酢酸メトキシプロピル中のポリマー2の溶液100gを21.4gのジメチルアミノプロピルアミンおよび107.1gの水と混合し、100℃に加熱して、その酢酸メトキシプロピルを共沸物として蒸留除去する。
12.2gのKOHを60gの水に溶解し、その後、27.78gのSMA 1000樹脂を80℃で溶解する。
酢酸メトキシプロピル中のポリマー4の溶液100gを21.5gのKOHおよび122.3gの水と混合し、100℃に加熱して、その酢酸メトキシプロピルを共沸物として蒸留除去する。
16gのKOHを250gの水に溶解し、その後、50gのSMA 1000樹脂を80℃で溶解する。その後、150gのアルコキシル化3級アミン(米国特許第2006/0089426号からの実施例9)を添加する。
(エステル1)
10.04gのPripol 1022に29.92gのPluriol A 750 Eおよび0.1gのp−トルエンスルホン酸を導入し、この初期混合物を210℃で反応させ、形成された水を分離除去する。カルボキシル基の90%がエステル化されたとき、反応を終了する。その後、水で固形分を40重量%に調整する。
24.35gのPripol 1022に202.7gのPluriol A2300PEおよび0.15gのp−トルエンスルホン酸を導入し、この初期混合物を210℃で反応させ、形成された水を分離除去する。カルボキシル基の90%がエステル化されたとき、反応を終了する。その後、水で固形分を40重量%に調整する。
10.04gのPripol 1022に14.96gのPluriol A 750 Eおよび0.06gのp−トルエンスルホン酸を導入し、この初期混合物を210℃で反応させ、形成された水を分離除去する。カルボキシル基の50%だけがエステル化されたとき、反応を終了する。その後、水で固形分を40重量%に調整する。
8.72gのタル油脂肪酸に26.1gのPluriol A 750 Eおよび0.06gのp−トルエンスルホン酸を導入し、この初期混合物を210℃で反応させ、形成された水を分離除去する。カルボキシル基の90%がエステル化されたとき、反応を終了する。その後、水で固形分を40重量%に調整する。
(湿潤分散剤1(本発明のもの)(W&D1))
50gのポリマー溶液4を50gのエステル1と混合し、均質化する。
50gのポリマー溶液4を50gのエステル3と混合し、均質化する。
50gのポリマー溶液4を50gのエステル4と混合し、均質化する。
Claims (31)
- 揮発性有機化合物(VOC)含有量が低い混合物であって、
I 少なくとも一つのエチレン性不飽和、フェニル基含有モノマーと少なくとも一つのα,β−不飽和モノカルボン酸および/または少なくとも一つのα,β−不飽和ジカルボン酸の、および場合によってはそれらの誘導体の、少なくとも50%塩化されたコポリマー10重量%から80重量%と、
II 末端OH末端基を含有し、少なくとも25モル%まではエチレンオキシドから合成される少なくとも一つの水溶性の線状ポリエーテル1重量%から30重量%と、
III 脂肪族ジカルボン酸の、および≦2000g/molの数平均分子量を好ましくは有する成分IIの水溶性ポリエーテルの少なくとも一つの、または≦2000g/molの数平均分子量を好ましくは有する成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、少なくとも一つのエステル化生成物5重量%から80重量%と、
IV ≦2000g/molの数平均分子量を好ましくは有する成分IIの水溶性ポリエーテルの少なくとも一つで、または≦2000g/molの数平均分子量を好ましくは有する成分IIの少なくとも一つの水溶性ポリエーテルを含有するポリエーテルの混合物で、3個から5個のカルボキシル基を含有する少なくとも一つの脂肪族カルボン酸をエステル化することによって得ることができる、少なくとも一つのスターポリマー3重量%から80重量%と
から構成され、成分IからIVの前記重量%の合計が、常に100重量%である必要があり、ならびに成分I−IVの前記重量%が、それぞれの場合、成分I−IVの前記総重量に基づく混合物。 - 30重量%から70重量%の成分Iと、
2重量%か10重量%の成分IIと、
10重量%から50重量%の成分IIIと、
5重量%から20重量%の成分IVと
を含み、成分IからIVの前記重量%の合計が、常に100重量%である必要があり、ならびに成分IからIVの前記重量%が、それぞれの場合、成分IからIVの前記総重量に基づくことを特徴とする、請求項1に記載の混合物。 - 成分Iが、少なくとも75%塩化されることを特徴とする、請求項1または2に記載の混合物。
- 成分Iが、アルカリ金属、アルカリ土類金属またはアンモニウム塩の形態、好ましくはナトリウムまたはカリウム塩の形態であることを特徴とする、請求項1から3のいずれかに記載の混合物。
- 前記成分Iの塩化コポリマーが、8から20個のC原子を好ましくは有する、少なくとも一つのエチレン性不飽和、フェニル基含有モノマー(該フェニルラジカルは、場合によっては少なくとも一回、置換されている可能性がある)と、3から8個の炭素原子を好ましくは有する少なくとも一つのα,β−不飽和モノカルボン酸および/または4から10個の炭素原子を好ましくは有するα,β−不飽和ジカルボン酸および/またはその環式無水物を、ならびに場合によってはそれらのそれぞれの誘導体、好ましくはエステルおよびアミドを重合させることによって調製されていることを特徴とする、請求項1から4のいずれかに記載の混合物。
- スチレン、ベンジル(メタ)アクリラート、およびフェニルアクリラート(該フェニルラジカルは、場合によっては1回から4回、置換されている可能性がある)を含む群から選択された少なくとも一つのモノマー、好ましくは場合によっては置換されているスチレンが、前記エチレン性不飽和、フェニル基含有モノマーとして使用されたことを特徴とする、請求項5に記載の混合物。
- アクリル酸またはメタクリル酸が、α,β−不飽和モノカルボン酸、および少なくとも一つのジカルボン酸(マレイン酸、フマル酸、およびイタコン酸および/または無水マレイン酸を含む群から選択される)として、ならびに場合によっては、それらのそれぞれの誘導体、好ましくはエステルまたはアミドとして使用され、少なくとも一つのC1−C6アルキルアクリラートおよび/またはC1−C6アルキルメタクリラートが、α,β−不飽和ジカルボン酸および/またはその環式無水物として使用されていることを特徴とする、請求項5または6に記載の混合物。
- 成分Iが、1:1から8:1の、好ましくは1:1から2:1のスチレン対無水マレイン酸比を有する塩化されたスチレン/無水マレイン酸コポリマーであることを特徴とする、請求項1から7のいずれかに記載の混合物。
- 成分IIが、少なくとも50mol%までエチレンオキシドから合成された少なくとも一つの水溶性ポリエーテルであることを特徴とする、請求項1から8のいずれかに記載の混合物。
- 成分IIが、エチレンオキシドの単位から、ならびに少なくとも一つの他のアルキレンオキシド、好ましくはプロピレンオキシド、ブチレンオキシドおよび/またはスチレンオキシドの単位から合成された少なくとも一つの水溶性ポリエーテルであることを特徴とする、請求項1から9のいずれかに記載の混合物。
- 成分IIが、エチレンオキシド単位から、ならびに3から20個のC原子を有する少なくとも一つの脂肪族もしくは芳香族グリシジルエーテル、好ましくはイソプロピルグリシジルエーテル、n−ブチルグリシジルエーテル、フェニルグリシジルエーテルもしくは2−エチルヘキシルポリグリシジルエーテルの単位から、および/または3から10個のC原子を有する少なくとも一つの脂肪族ラクトン、好ましくはプロピオラクトン、バレロラクトンおよび/またはε−カプロラクトンの単位から合成された少なくとも一つの水溶性ポリエーテルであることを特徴とする、請求項1から9のいずれかに記載の混合物。
- 成分IIIが、成分IIの少なくとも一つの水溶性ポリエーテルの、または成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、および12から22個のC原子を有する不飽和脂肪酸をオリゴマー化することによって得ることができる脂肪族の場合によっては飽和されているダイマー酸の、エステル化生成物であることを特徴とする、請求項1から11のいずれかに記載の混合物。
- 成分IIIが、成分IIの少なくとも一つの水溶性ポリエーテルの、または成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、および場合によっては不飽和の脂肪族ジカルボン酸無水物、好ましくは無水マレイン酸もしくは無水コハク酸とC2からC20を有する少なくとも一つの脂肪族ジオールとを反応させることによって得ることができる、場合によっては部分的にエステル化されている脂肪族ジカルボン酸であって、3から10個のC原子を有する少なくとも一つの脂肪族ラクトンに基づく、末端にジヒドロキシを有する脂肪族ポリエステルとの反応の結果として場合によっては連鎖延長されていることがある該ジカルボン酸の、エステル化生成物であることを特徴とする、請求項1から11のいずれかに記載の混合物。
- 成分IIIが、成分IIの少なくとも一つの水溶性ポリエーテルの、または成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、および場合によっては不飽和の脂肪族ジカルボン酸無水物、好ましくは無水マレイン酸もしくは無水コハク酸と二個の第一アミノ基を含有し且つ2から20個のC原子を有する少なくとも一つの直鎖状または分岐、脂肪族または環状脂肪族ジアミンとを反応させることによって得ることができる、場合によっては部分的にアミド化されている脂肪族ジカルボン酸の、エステル化生成物であることを特徴とする、請求項1から11のいずれかに記載の混合物。
- 成分IVが、成分IIの水溶性ポリエーテルの少なくとも一つの、または成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、および12から22個のC原子を有する不飽和脂肪酸をオリゴマー化することによって得ることができる、場合によっては飽和されているトリマー酸の、エステル化生成物であることを特徴とする、請求項1から14のいずれかに記載の混合物。
- 成分IVが、成分IIの少なくとも一つの水溶性ポリエーテルの、または成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、および3から5個のカルボキシル基を含有する少なくとも一つの場合によっては部分的にエステル化されている脂肪族多価カルボン酸であって、場合によっては不飽和の脂肪族ジカルボン酸無水物、好ましくは無水マレイン酸もしくは無水コハク酸と3から5個のOH基を有する少なくとも一つの脂肪族ポリオールとを反応させることによって得ることができ、場合によっては、3から10個のC原子を有する脂肪族ラクトンに基づくポリエステルとの1:1の前記無水物官能基対前記ヒドロキシル官能基の化学量論比での反応の結果として連鎖延長されていることがある前記多価カルボン酸の、エステル化生成物であることを特徴とする、請求項1から14のいずれかに記載の混合物。
- 成分IVが、成分IIの少なくとも一つの水溶性ポリエーテルの、または成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物の、および3から5個のカルボキシル基を含有する少なくとも一つの場合によってはアミド化されている脂肪族多価カルボン酸であって、場合によっては不飽和の脂肪族ジカルボン酸無水物、好ましくは無水マレイン酸もしくは無水コハク酸と合計3から5個の第一および/または第二アミノ基を有する脂肪族ポリアミンとを、1:1の前記無水物官能基対前記アミノ官能基の化学量論比で反応させることによって得ることができる前記多価カルボン酸の、エステル化生成物であることを特徴とする、請求項1から14のいずれかに記載の混合物。
- 成分IIIおよびIVが、12から22個のC原子を有する不飽和脂肪酸を成分IIの水溶性ポリエーテルの少なくとも一つでまたは成分IIの少なくとも一つの水溶性ポリエーテルを含むポリエーテルの混合物でオリゴマー化することによって得ることができる、ダイマー酸とトリマー酸の混合物のエステル化生成物であることを特徴とする、請求項1から15のいずれかに記載の混合物。
- 使用されるダイマー酸とトリマー酸との混合物における前記ダイマー酸のトリマー酸に対する比率が、10:90から90:10であることを特徴とする、請求項18に記載の混合物。
- 前記ダイマー酸が、36個以下のC原子を有し、および前記トリマー酸が、54個以下のC原子を有することを特徴とする、請求項19に記載の混合物。
- 低VOC湿潤分散剤としての、請求項1から20のいずれかに記載の混合物の使用。
- 固体を分散させるための、請求項21に記載の使用。
- 顔料を分散させるための、請求項21または22に記載の使用。
- 低VOC、水性顔料濃縮物を調製するための、請求項23に記載の使用。
- コーティング材料、好ましくは塗料を製造するための、請求項24に記載の顔料濃縮物としての使用。
- 請求項1から20のいずれかに記載の混合物を湿潤分散剤として含む、水性、低VOC顔料濃縮物。
- 少なくとも一つの顔料と、請求項1から20のいずれかに記載の混合物と、水性分散媒と、場合によっては低VOC、有機ビヒクルと、場合によっては他の助剤とを含むペイントまたはペースト。
- 請求項1から20のいずれかに記載の混合物でコーティングされた、分散性、多粒子状および/または繊維状固体。
- 顔料であることを特徴とする、請求項28に記載の分散性、多粒子状固体。
- インク、好ましくは非衝撃式印刷プロセス用の水性インクを製造するための、請求項1から20のいずれかに記載の混合物の使用。
- 化粧用製剤、好ましくはW/OエマルジョンもしくはO/Wエマルジョン、溶液、ゲル、クリーム、ローションまたはスプレー剤における湿潤分散剤としての、請求項1から20のいずれかに記載の混合物の使用。
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- 2009-02-03 EP EP09708255A patent/EP2240543B1/de active Active
- 2009-02-03 JP JP2010545394A patent/JP5762751B2/ja active Active
- 2009-02-03 KR KR1020107017629A patent/KR101631330B1/ko active IP Right Grant
- 2009-02-03 CN CN200980111885XA patent/CN101983222B/zh active Active
- 2009-02-03 WO PCT/EP2009/000699 patent/WO2009098025A1/de active Application Filing
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2013515106A (ja) * | 2009-12-22 | 2013-05-02 | ビック−ケミー ゲゼルシャフト ミット ベシュレンクテル ハフツング | 安定なポリオール混合物を含む組成物 |
JP2017528540A (ja) * | 2014-07-01 | 2017-09-28 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングBASF Coatings GmbH | ダイマー脂肪酸を主体としたカルボキシ官能性反応生成物、および前記反応生成物を含む水性ベースコート材料 |
JP2020517756A (ja) * | 2016-10-28 | 2020-06-18 | ジョヴァンニ ブロッジー | プラスチックの着色および強化のための万能的な色素製剤 |
JP7064504B2 (ja) | 2016-10-28 | 2022-05-10 | ジョヴァンニ ブロッジー | プラスチックの着色および強化のための万能的な色素製剤 |
KR20240033249A (ko) | 2021-07-15 | 2024-03-12 | 산 노프코 가부시키가이샤 | 분산제 및 수계 코팅 조성물 |
Also Published As
Publication number | Publication date |
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US20100322879A1 (en) | 2010-12-23 |
KR101631330B1 (ko) | 2016-06-16 |
JP5762751B2 (ja) | 2015-08-12 |
CN101983222A (zh) | 2011-03-02 |
US8097076B2 (en) | 2012-01-17 |
ES2393560T3 (es) | 2012-12-26 |
EP2240543A1 (de) | 2010-10-20 |
DE102008007713A1 (de) | 2009-08-06 |
CN101983222B (zh) | 2013-03-13 |
EP2240543B1 (de) | 2012-08-29 |
KR20100121482A (ko) | 2010-11-17 |
WO2009098025A1 (de) | 2009-08-13 |
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