TW202204461A - Cmp研磨墊用中空微球 - Google Patents
Cmp研磨墊用中空微球 Download PDFInfo
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- TW202204461A TW202204461A TW110111892A TW110111892A TW202204461A TW 202204461 A TW202204461 A TW 202204461A TW 110111892 A TW110111892 A TW 110111892A TW 110111892 A TW110111892 A TW 110111892A TW 202204461 A TW202204461 A TW 202204461A
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- Prior art keywords
- component
- resin
- acid
- cmp polishing
- compound
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Abstract
本發明之CMP研磨墊用中空微球係由選自由三聚氰胺樹脂、脲樹脂,及醯胺樹脂所成群組之至少1種樹脂所構成之平均粒徑為1~100μm。
依據本發明時,可提供用於CMP研磨墊時,可發揮優異之研磨特性,CMP研磨墊製造時,可安定地製造CMP研磨墊的CMP研磨墊用中空微球。
Description
本發明係有關CMP研磨墊用中空微球。
微球(microballoon)自以往作為包含護膚(skin care)成分、香料成分、染料成分、鎮痛成分、消臭成分、抗氧化成分、殺菌成分、蓄熱成分等的微球、或微球內部為中空的中空微球,在農藥、醫藥、香料、液晶、接著劑、電子材料零件、建築材料等之許多領域中使用。
特別是近年來,在晶圓研磨用之聚胺基甲酸酯(脲)製CMP(Chemical Mechanical Polishing)研磨墊,設置細孔之目的,而檢討中空微球。
以往,作為CMP研磨墊用的中空微球,為了提高對作為CMP研磨墊之基材之一般用之聚胺基甲酸酯(脲)樹脂之分散性,在中空微球之表面均勻黏附了無機粒子之偏二氯乙烯樹脂等的微球為人所知(專利文獻1),但是該無機粒子可能成為晶圓之缺點的主要原因。
因此,本發明人等提案藉由將高彈性,且與CMP研磨墊之基材之聚胺基甲酸酯(脲)樹脂之相容性良好的聚胺基甲酸酯(脲)樹脂所構成的中空微球用於CMP研磨墊中,而具有優異研磨特性的CMP研磨墊(參照專利文獻2)。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開2019-63903號
[專利文獻2]國際公開第2019/198675號
[發明所欲解決之課題]
專利文獻2確實藉由使用由聚胺基甲酸酯(脲)樹脂之所構成之中空微球,可展現優異的研磨特性。但是因用於CMP研磨墊之樹脂之聚合性單體的種類,由聚胺基甲酸酯(脲)樹脂所構成之中空微球的耐溶劑性有疑慮。具體而言,特別是該中空微球與該聚合性單體之混合物長時間保存時,對於該中空微球,該聚合性單體由於滲透或部分溶解,該中空微球有變形的情形,故所期望之CMP用研磨墊之安定製造仍有改善的餘地。
因此,本發明之目的係可提供用於CMP研磨墊時,不僅優異之研磨特性,且中空微球具有優異之耐溶劑性,CMP研磨墊製造時,可安定地製造CMP研磨墊的中空微球。
[用以解決課題之手段]
本發明人等為了解決上述課題而精心檢討的結果,發現由選自由三聚氰胺樹脂、脲樹脂,及醯胺樹脂所成群組之至少1種樹脂所構成,且特定範圍之平均粒徑的中空微球,可解決上述課題,遂完成本發明。
亦即,本發明係有關以下[1]~[9]。
[1]一種CMP研磨墊用中空微球,其係由選自由三聚氰胺樹脂、脲樹脂,及醯胺樹脂所成群組之至少1種樹脂所構成之平均粒徑為1~100μm。
[2]如上述[1]之CMP研磨墊用中空微球,其中前述中空微球之體積密度(bulk density)
為0.01~0.6g/cm3
。
[3]如上述[1]或[2]之CMP研磨墊用中空微球,其中該中空微球設為100質量份時,前述中空微球之灰分(ash)為0.5質量份以下。
[4]一種CMP研磨墊,其係由包含如上述[1]~[3]中任一項之CMP研磨墊用中空微球與聚胺基甲酸酯(脲)樹脂而成。
[5]如上述[4]之CMP研磨墊,其中蕭氏硬度(shore D hardness)為30A~70D。
[6]如上述[4]或[5]之CMP研磨墊,其中前述聚胺基甲酸酯(脲)樹脂為使含有(B)多官能異氰酸酯化合物與(CA)具有2個以上之胺基之化合物的聚合性組成物,進行聚合的樹脂。
[7]如上述[4]~[6]中任一項之CMP研磨墊,其中前述聚胺基甲酸酯(脲)樹脂為使含有(B)多官能異氰酸酯化合物、(CA)具有2個以上之胺基之化合物及(CB)具有3個以上之羥基及/或硫醇基之化合物的聚合性組成物,進行聚合的樹脂。
[8]如上述[7]之CMP研磨墊,其中前述聚合性組成物中之前述(B)多官能異氰酸酯化合物、前述(CA)具有2個以上之胺基之化合物及前述(CB)具有3個以上之羥基及/或硫醇基之化合物的調配比例為(B)成分、(CA)成分、及(CB)成分之合計100質量份時,(B)成分為60~95質量份,(CA)成分為2~20質量份,及(CB)成分為1~30質量份。
[9]如上述[7]~[8]中任一項之CMP研磨墊,其中前述(CB)具有3個以上之羥基及/或硫醇基之化合物為具有3個以上之羥基及/或硫醇基的聚輪烷。
[發明效果]
本發明之CMP研磨墊用中空微球係由選自由三聚氰胺樹脂、脲樹脂,及醯胺樹脂所成群組之至少1種樹脂所構成,且平均粒徑為1~100μm的中空微球,用於CMP研磨墊為特徵。因此,可展現優異的研磨特性。例如可降低對晶圓產生的缺點。此外,該中空微球因具有優異的耐溶劑性,故CMP研磨墊製造時,可安定地製造CMP研磨墊。
又,本發明之CMP研磨墊用中空微球係適合CMP研磨墊用途的中空微球,除了CMP研磨墊用途外,也可在感熱記錄材料、農藥、醫藥、香料、液晶、接著劑、電子材料零件、建築材料等其他的領域使用。
又,本說明書中,CMP研磨墊用中空微球有時僅單純記載中空微球。
[實施發明之形態]
本發明之CMP研磨墊用中空微球為該中空微球之樹脂為選自由三聚氰胺樹脂、脲樹脂、及醯胺樹脂所構成群組之至少1種樹脂所構成。
其中,本發明較佳之樹脂為三聚氰胺樹脂。
又,本發明中,三聚氰胺樹脂係指主鏈為包含三聚氰胺之多官能胺與甲醛之聚縮合所得的樹脂,脲樹脂係指主鏈為脲(進一步有包含多官能胺的情形)與甲醛之聚縮合所得的樹脂,醯胺樹脂係指主鏈具有醯胺鍵的樹脂。
本發明之CMP研磨墊用中空微球之平均粒徑為1~100μm。藉由在此範圍,調配於CMP研磨墊時,可展現優異的研磨特性。此外,該中空微球之平均粒徑,較佳為5~80μm,更佳為10~50μm。
中空微球之平均粒徑之測定,可採用習知的方法即可,具體而言,可使用圖像解析法。藉由使用圖像解析法,可容易測定粒子尺寸。又,平均粒徑為一次粒子的平均粒徑。藉由圖像解析法測定平均粒徑,例如可使用掃描型電子顯微鏡(SEM)等測定。例如,藉由SEM,測定100個中空微球的粒徑,將此平均,可求平均粒徑。
本發明之CMP研磨墊用中空微球之體積密度,無特別限制,較佳為0.01~0.6g/cm3
,更佳為0.02~0.4g/cm3
。藉由在此範圍,可在CMP研磨墊之研磨面形成最佳的細孔。
本發明之CMP研磨墊用中空微球之灰分,無特別限制,在後述之實施例所記載的方法中,該中空微球為100質量份時,較佳為0.5質量份以下,又更佳為0.3質量份以下,更佳為0.1質量份以下,最佳為無法測定。藉由在此範圍,用於CMP研磨墊時,可降低晶圓的缺點。
本發明之CMP研磨墊用中空微球係如前述,由三聚氰胺樹脂、脲樹脂及醯胺樹脂之至少1種樹脂所構成。又,通常,此等樹脂係將以下所示之聚合性單體進行聚合所得。
本發明中,構成此等樹脂的聚合性單體,可列舉以下者。
前述CMP研磨墊用中空微球為由三聚氰胺樹脂所構成時,作為聚合性單體,使用三聚氰胺與甲醛,必要時使用其他的多官能胺即可,其中,較佳為使用三聚氰胺甲醛預聚物化合物。
前述三聚氰胺甲醛預聚物化合物係三聚氰胺與甲醛之三聚氰胺-甲醛初期縮合物,可以常法製造。三聚氰胺與甲醛之三聚氰胺-甲醛初期縮合物,可列舉例如羥甲基三聚氰胺等。又,三聚氰胺甲醛預聚物化合物,可適宜使用市售者。例如BECKAMINE APM、BECKAMINE M-3、BECKAMINE M-3(60)、BECKAMINE MA-S、
BECKAMINE J-101、BECKAMINE J-1 01LF(DIC股份公司製)、Nika Resin S-176、Nika Resin S-260(NIPPON CARBIDE股份公司製)、Mirbane resin SM-800(昭和高分子股份公司製)等。
前述CMP研磨墊用中空微球為由脲樹脂所構成時,作為聚合性單體,使用脲與甲醛,必要時使用其他之多官能胺即可,其中,較佳為使用脲甲醛預聚物化合物。
前述脲甲醛預聚物化合物係脲與甲醛之脲-甲醛初期縮合物,可以常法製造。脲與甲醛之脲-甲醛初期縮合物,可列舉例如羥甲基脲等。又,脲甲醛預聚物化合物,可適宜使用市售者。可列舉例如8HSP(昭和高分子股份公司製)等。
前述CMP研磨墊用中空微球為由醯胺樹脂所構成時,作為聚合性單體,使用具有至少2個羧基的多官能羧酸化合物與具有至少2個胺基之多官能胺化合物即可。
前述具有至少2個羧基的多官能羧酸化合物,較佳為二羧酸化合物,可列舉二羧酸、二羧酸二鹵化物。
前述二羧酸,可列舉琥珀酸、己二酸、癸二酸、十二烯基琥珀酸、壬二酸、癸二酸、十四烷二酸、十八烷二羧酸、十二烯基琥珀酸、十五碳烯琥珀酸、十八烯基琥珀酸、馬來酸、富馬酸等之伸烷基二羧酸、癸基琥珀酸、十二烷基琥珀酸、十八烷基琥珀酸、苯二甲酸、間苯二甲酸、對苯二甲酸、萘二甲酸等。
又,前述二羧酸二鹵化物,可列舉脂肪族二羧酸二鹵化物、脂環族二羧酸二鹵化物、及芳香族二羧酸二鹵化物。
前述脂肪族二羧酸二鹵化物,可列舉草酸二氯化物、丙二酸二氯化物、琥珀酸二氯化物、富馬酸二氯化物、戊二酸二氯化物、己二酸二氯化物、黏康酸(Muconic acid)二氯化物、癸二酸二氯化物、壬酸二氯化物、十一烷酸二氯化物、草酸二溴化物、丙二酸二溴化物、琥珀酸二溴化物、富馬酸二溴化物等。
前述脂環族二羧酸二鹵化物,可列舉1,2-環丙烷二羧酸二氯化物、1,3-環丁烷二羧酸二氯化物、1,3-環戊烷二羧酸二氯化物、1,3-環己烷二羧酸二氯化物、1,4-環己烷二羧酸二氯化物、1,3-環戊烷二羧酸二氯化物、1,2-環丙烷二羧酸二溴化物、1,3-環丁烷二羧酸二溴化物等。
前述芳香族二羧酸二鹵化物,可列舉苯二甲酸二氯化物、間苯二甲酸二氯化物、對苯二甲酸二氯化物、1,4-萘二甲酸二氯化物、1,5-(9-氧代茀)二羧酸二氯化物、1,4-蒽二羧酸二氯化物、1,4-蒽醌二羧酸二氯化物、2,5-聯苯基二羧酸二氯化物、1,5-聯苯二甲酸二氯化物、4,4’-聯苯基二羰基氯化物、4,4’-亞甲基二苯甲酸二氯化物、4,4’-異亞丙基二苯甲酸二氯化物、4,4’-聯苄二羧酸二氯化物、4,4’-茋二羧酸二氯化物、4,4’-伸乙基聯苯二甲酸(Ethynylenedibenzoic acid)二氯化物、4,4’-羰基二苯甲酸二氯化物、4,4’-羥基二苯甲酸二氯化物、4,4’-磺醯基二苯甲酸二氯化物、4,4’-二硫代二苯甲酸二氯化物、p-伸苯基二乙酸二氯化物、3,3’-p-伸苯基二丙酸二氯化物、苯二甲酸二溴化物、間苯二甲酸二溴化物、對苯二甲酸二溴化物等。
本發明中,具有至少2個羧基的多官能羧酸化合物,就聚合速度的觀點,較佳為二羧酸二鹵化物。
此等具有至少2個羧基的多官能性羧酸化合物,可單獨使用,也可組合2種類以上使用。
又,前述具有至少2個胺基的多官能胺化合物,只要是1分子中具有2個以上之胺基的化合物時,即可使用無特別限制。本發明中,可較適合使用之具有至少2個胺基的多官能胺化合物為水溶性多胺化合物。
前述水溶性多胺化合物係至少局部在水中有溶解性,相較於疏水性相,在親水性相中,具有較高親和性的化合物,一般而言,可選擇在室溫下,如水之親水性溶劑中之溶解性為具有至少1g/l之溶解性者,可列舉較佳為在親水性溶劑中,具有20g/l以上之溶解性的水溶性化合物。
前述水溶性多胺化合物係在分子內具有2個以上之胺基之水溶性的多官能胺,具體而言,可列舉乙二胺、丙二胺、1,4.-二胺基丁烷、己二胺、1.8-二胺基辛烷、1.10-二胺基癸烷、二丙烯三胺、雙(六亞甲基)三胺、三(2-胺基乙基)胺、哌嗪、2-甲基哌嗪、異佛爾酮二胺、二伸乙三胺、三伸乙四胺、四伸乙五胺、肼、聚乙烯亞胺類、聚氧化烯胺類、聚乙烯亞胺、伸苯基二胺(o-,m-,p-)、4,4-二胺基二苯基甲烷等。
此等具有至少2個胺基的多官能性胺化合物,可單獨使用,也可組合2種類以上使用。
本發明之CMP研磨墊用中空微球之製造方法,可使用習知的方法無限制。可採用例如將構成樹脂之聚合性單體,作為水相與油相所得的乳膠,然後,以凝聚法、In-situ、或界面聚合等的方法進行聚合製作微球後,藉由去除內部的液體,製造中空微球的方法即可。具體而言,可列舉以下的方法,但是不限於以下的方法。前述CMP研磨墊用中空微球為由三聚氰胺樹脂或脲樹脂所構成時,形成油中水(O/W)乳膠(以下也稱為O/W乳膠)後,可適合藉由In-situ聚合製作。下述表示具體例,本發明的製造方法,不限定於此。
將前述CMP研磨墊用中空微球為由三聚氰胺樹脂、或脲樹脂所構成時之O/W乳膠的聚合方法細分時,可分類成以下步驟:第1步驟:調製(a)包含有機溶劑的油相(以下也稱為(a)成分)的步驟,第2步驟:調製(A)含有乳化劑的水相(以下也稱為(A)成分)的步驟,第3步驟:將前述(a)成分與前述(A)成分進行混合‧攪拌,調製前述水相為連續相,前述油相為分散相所成之O/W乳膠的步驟,第4步驟:在前述O/W乳膠中,添加三聚氰胺甲醛預聚物化合物(三聚氰胺樹脂時)、或脲甲醛預聚物(脲樹脂時),在前述O/W乳膠之界面上進行In-situ聚合,使形成樹脂膜,作為微球,得到分散有微球之微球分散液的步驟,第5步驟:由前述微球分散液分離微球的步驟,第6步驟:由前述微球之內部,去除有機溶劑溶液,作為中空微球的步驟。
第1步驟:
第1步驟係調製O/W乳膠中成為分散相之(a)包含有機溶劑之油相的步驟。
第2步驟:
第2步驟係調製在O/W乳膠中成為連續相之(A)包含乳化劑與水之水相的步驟,必要時包含調製pH的步驟。
此步驟係在水中,使後述之乳化劑溶解,必要時包含調製pH的步驟。pH之調製等,以習知的方法調合即可。
本發明中,相對於水相100質量份,乳化劑之使用量為0.01~20質量份,較佳為0.1~10質量份。在此範圍時,可避免O/W乳膠中之分散相之液滴的凝聚,可容易得到平均粒徑完整的微球。
又,較佳之pH為pH未達7,又更佳為pH為3.5~6.5,最佳為pH調製成為4.0~5.5。藉由在此pH範圍,可使三聚氰胺甲醛預聚物化合物(三聚氰胺樹脂時)、或脲甲醛預聚物(脲樹脂時)進行In-situ聚合。
第3步驟:
第3步驟係將第1步驟所得之(a)成分與第2步驟所得之(A)成分進行混合‧攪拌,調製(A)成分成為連續相,(a)成分成為分散相而成之O/W乳膠的步驟。
本發明中,將(a)成分與(A)成分進行混合、攪拌,作為O/W乳膠的方法,考慮欲製造之微球的粒徑,可藉由適宜習知的方法,進行混合‧攪拌來調製。此外,調製O/W乳膠之步驟中,也可調製溫度或pH。
其中,使(a)成分與(A)成分混合後,攪拌適合採用使用高速剪切式、摩擦式、高壓噴射式、超音波式等之公知的分散機進行分散的方法,作為O/W乳膠化的方法,此等之中,較佳為高速剪切式。使用高速剪切式分散機時,旋轉數較佳為500~20,000rpm,又更佳為1,000~10,000rpm。分散時間較佳為0.1~60分鐘,較佳為0.5~30分鐘。分散溫度,較佳為20~90℃。
又,本發明中,(a)成分與(A)成分之重量比係當(a)成分設為100質量份時,(A)成分較佳為100~1000質量份,又更佳為150~500質量份。在此範圍時,可得到良好的乳膠。
第4步驟:
第4步驟係在前述O/W乳膠中加入三聚氰胺甲醛預聚物化合物(三聚氰胺樹脂時)、或脲甲醛預聚物(脲樹脂時),在O/W乳膠之界面上進行In-situ聚合,形成樹脂膜,作為微球,得到分散有形成之微球之微球分散液的步驟。
使用之三聚氰胺甲醛預聚物化合物(三聚氰胺樹脂時)、或脲甲醛預聚物(脲樹脂時)之使用量,無特別限制,為了良好形成微球時,在第1步驟使用的有機溶劑100質量份時,較佳為0.5~50質量份,更佳為1~20質量份。
又,將三聚氰胺甲醛預聚物化合物(三聚氰胺樹脂時)、或脲甲醛預聚物(脲樹脂時)加入O/W乳膠中時,可直接加入使用,也可溶解於水來使用。
溶解於水時,三聚氰胺甲醛預聚物化合物(三聚氰胺樹脂時)、或脲甲醛預聚物(脲樹脂時)之合計量設為100質量份時,較佳為水在50~10,000質量份之範圍內使用。
連續相之水相之pH可在第2步驟調整,也可在第4步驟中,前述O/W乳膠中加入三聚氰胺甲醛預聚物化合物(三聚氰胺樹脂時)、或脲甲醛預聚物(脲樹脂時)後,進行調整。連續相之水相之pH係與前述同樣,較佳為未達7,又更佳為pH為3.5~6.5,最佳為pH調整為4.0~5.5。較佳之反應溫度係在40~90℃之範圍內實施反應較佳。反應時間為1~48小時之範圍內實施較佳。
第5步驟
第5步驟係自前述微球分散液分離微球的步驟。自微球分散液分離微球的分離方法,無特別限制,選自一般的分離手法即可,具體而言,可使用過濾或離心分離等。
第6步驟
第6步驟係自第5步驟所得之前述微球去除內部的油相,形成中空微球的步驟。自微球去除油相的方法,無特別限制,可選自一般的分離手法即可,具體而言,可使用循風乾燥機、噴霧乾燥機、流動層式乾燥機、真空乾燥機等。乾燥時之溫度條件,較佳為40~250℃,又更佳為50~200℃。
前述CMP研磨墊用中空微球為由醯胺樹脂所構成時,可藉由界面聚合製作。該界面聚合係製作O/W乳膠或、油中水(W/O)乳膠(以下也稱為W/O乳膠)後,乳膠之界面上進行聚合的方法。本發明,可選擇O/W乳膠、或W/O乳膠,以O/W乳膠之界面聚合可有效率製作中空微球,故較佳。下述例示藉由O/W乳膠之界面聚合製作中空微球的方法。
將前述CMP研磨墊用中空微球為由醯胺樹脂所構成時之O/W乳膠的聚合方法細分時,第1步驟:調製(c)包含具有至少2個羧基的多官能羧酸化合物與有機溶劑的油相(以下也稱為(c)成分)的步驟,第2步驟:調製(d)包含乳化劑之水相(以下也稱為(d)成分)的步驟,第3步驟:將前述(c)成分與前述(d)成分進行混合‧攪拌,調製前述水相為連續相,前述油相為分散相而成之O/W乳膠的步驟,第4步驟:在前述O/W乳膠中加入具有至少2個胺基的多官能胺化合物,在前述O/W乳膠之界面上進行界面聚合,形成樹脂膜,作為微球,得到分散有微球之微球分散液的步驟,第5步驟:自前述微球分散液分離微球的步驟,第6步驟:由前述微球之內部去除有機溶劑溶液,作為中空微球的步驟。
第1步驟:
第1步驟係調製O/W乳膠中成為分散相之(c)包含具有至少2個羧基的多官能羧酸化合物與有機溶劑之油相的步驟。
此步驟係在後述之有機溶劑中,使具有至少2個羧基的多官能羧酸化合物溶解作為油相的步驟,以習知的方法溶解作為均勻的溶液即可。
相對於有機溶劑100質量份,較佳之具有至少2個羧基的多官能羧酸化合物之使用量為0.1~50質量份,較佳為0.5~20質量份,又更佳為1~10質量份。此外,相對於具有至少2個羧基的多官能羧酸化合物所含有之羧酸基的莫耳數(n1),具有至少2個胺基的多官能胺化合物之合計之含胺基之化合物的莫耳數為(n2)時,較佳為0.5≦(n1)/(n2)≦2的範圍。
又,(c)成分中,為了促進界面聚合之反應之目的,可添加後述的觸媒。
第2步驟:
第2步驟係調製在O/W乳膠成為連續相之(d)包含乳化劑與水之水相的步驟。
此步驟係使後述之乳化劑溶解於水中,作為水相的步驟,以習知的方法溶解,作為均勻的溶液即可。
本發明中,相對於水相100質量份,乳化劑之使用量為0.01~20質量份,較佳為0.1~10質量份。在此範圍時,可避免O/W乳膠中之分散相之液滴之凝聚,可容易得到平均粒徑完整的微球。
又,(d)成分中,為了促進界面聚合之反應之目的,可添加後述的觸媒。
第3步驟:
第3步驟係將第1步驟所得之(c)成分與第2步驟所得之(d)成分進行混合‧攪拌,調製(d)成分為連續相,(c)成分為分散相而成之O/W乳膠的步驟。
本發明中,將(c)成分與(d)成分進行混合、攪拌,作為O/W乳膠的方法,考慮欲製造之微球的粒徑,可藉由適宜習知的方法,進行混合‧攪拌來調製。
其中,使(c)成分與(d)成分混合後,攪拌適合採用使用高速剪切式、摩擦式、高壓噴射式、超音波式等之公知的分散機進行分散的方法,作為O/W乳膠化的方法,此等之中,較佳為高速剪切式。使用高速剪切式分散機時,旋轉數較佳為500~20,000rpm,又更佳為1,000~10,000rpm。分散時間較佳為0.1~60分鐘,較佳為0.5~30分鐘。分散溫度,較佳為10~40℃。
又,本發明中,(c)成分與(d)成分之重量比係當(c)成分設為100質量份時,(d)成分較佳為100~1000質量份,又更佳為150~500質量份。在此範圍時,可得到良好的乳膠。
第4步驟:
第4步驟係在前述O/W乳膠中加入具有至少2個胺基的多官能胺化合物,在O/W乳膠之界面上使界面聚合,形成樹脂膜,作為微球,得到分散有該微球之微球分散液的步驟。該具有至少2個胺基的多官能胺化合物之使用量係如前述。
又,將具有至少2個胺基的多官能胺化合物加入於O/W乳膠中時,可直接加入使用,也可溶解於水來使用。
溶解於水時,具有至少2個胺基的多官能胺化合物之合計量設為100質量份時,較佳為水在50~10,000質量份之範圍內使用。
聚合溫度係不會破壞O/W乳膠的溫度時,即無特別限制,較佳為5~70℃之範圍實施反應。聚合時間只要可形成微球時,即無特別限制,通常選自0.5~24小時的範圍。
第5步驟、第6步驟
第5步驟、第6步驟係與前述CMP研磨墊用中空微球為由三聚氰胺樹脂、或脲樹脂所構成時相同的步驟。
以下說明本發明使用的各成分。
本發明中,(A)成分或(d)成分所使用的乳化劑,包含分散劑、界面活性劑、或此等之組合。
分散劑可列舉例如聚乙烯醇及其改性物(例如,陰離子改性聚乙烯醇)、纖維素系化合物(例如,甲基纖維素、乙基纖維素、羥基乙基纖維素、乙基羥基乙基纖維素、羧基甲基纖維素、羥基丙基纖維素及彼等之皂化物等)、聚丙烯酸醯胺及其衍生物、乙烯-乙酸乙烯酯共聚物、苯乙烯-馬來酸酐共聚物、乙烯-馬來酸酐共聚物、異丁烯-馬來酸酐共聚物、聚乙烯基吡咯烷酮、乙烯-丙烯酸共聚物、乙酸乙烯酯-丙烯酸共聚物、聚丙烯酸鈉、聚丙烯酸鉀、聚丙烯酸銨、聚丙烯酸之部分中和物、丙烯酸鈉-丙烯酸酯共聚物、羧基甲基纖維素、酪蛋白、明膠、糊精、幾丁聚醣、殼聚糖、澱粉衍生物、阿拉伯膠及褐藻酸鈉等。
此等之分散劑,較佳為不會與本發明使用之聚合性單體反應,或反應非常困難,例如明膠等之分子鏈中具有反應性之胺基者,預先實施使失去反應性之處理為佳。
界面活性劑,可列舉陰離子界面活性劑、陽離子界面活性劑、兩性界面活性劑、非離子界面活性劑等。界面活性劑也可併用2種以上之界面活性劑者。
陰離子界面活性劑,可列舉羧酸或其鹽、硫酸酯鹽、羧基甲基化物之鹽、磺酸鹽及磷酸酯鹽。
羧酸或其鹽,可列舉碳數8~22之飽和或不飽和脂肪酸或其鹽,具體而言,可列舉癸酸、月桂酸、肉豆蔻酸、棕櫚酸、硬脂酸、花生酸、二十二酸、油酸、亞麻油酸、亞油酸及椰子油、棕櫚仁油、米糠油、牛脂等進行皂化所得之高級脂肪酸的混合物。鹽可列舉彼等之鈉、鉀、銨、烷醇胺等之鹽。
硫酸酯鹽,可列舉高級醇硫酸酯鹽(碳數8~18之脂肪族醇的硫酸酯鹽)、高級烷醚硫酸酯鹽(碳數8~18之脂肪族醇之環氧乙烷加成物之硫酸酯鹽)、硫酸化油(不飽和油脂或不飽和之蠟直接硫酸化,進行中和者)、硫酸化脂肪酸酯(不飽和脂肪酸之低級醇酯進行硫酸化,進行中和者)及硫酸化烯烴(碳數12~18之烯烴進行硫酸化,進行中和者)。鹽可列舉鈉鹽,鉀鹽,銨鹽,烷醇胺鹽。
高級醇硫酸酯鹽之具體例,可列舉辛基醇硫酸酯鹽、癸基醇硫酸酯鹽、月桂基醇硫酸酯鹽、十八烷基醇硫酸酯鹽、羰氧化法所合成之醇(OXOCOL 900、三癸醇:協和發酵製)的硫酸酯鹽。
高級烷醚硫酸酯鹽之具體例,可列舉月桂基醇環氧乙烷2莫耳加成物硫酸酯鹽、辛基醇環氧乙烷3莫耳加成物硫酸酯鹽。
硫酸化油之具體例,可列舉蓖麻油、落花生油、橄欖油、芥菜籽油、牛脂、羊脂等之硫酸化物之鈉、鉀、銨、烷醇胺鹽。
硫酸化脂肪酸酯之具體例,可列舉油酸丁酯,蓖麻油酸丁酯等之硫酸化物之鈉、鉀、銨、烷醇胺鹽。
羧基甲基化物之鹽,可列舉碳數8~16之脂肪族醇之羧基甲基化物之鹽及碳數8~16之脂肪族醇之環氧乙烷加成物之羧基甲基化物之鹽。
脂肪族醇之羧基甲基化物之鹽的具體例,可列舉辛基醇羧基甲基化鈉鹽、癸基醇羧基甲基化鈉鹽、月桂基醇羧基甲基化鈉鹽、三癸醇羧基甲基化鈉鹽等。
脂肪族醇之環氧乙烷加成物之羧基甲基化物之鹽的具體例,可列舉辛基醇環氧乙烷3莫耳加成物羧基甲基化鈉鹽、月桂基醇環氧乙烷4莫耳加成物羧基甲基化鈉鹽、三癸醇環氧乙烷5莫耳加成物羧基甲基化鈉鹽等。
磺酸鹽,可列舉烷基苯磺酸鹽、烷基萘磺酸鹽、硫代琥珀酸二酯型、α-烯烴磺酸鹽、IgeponT型、其他含有芳香環之化合物的磺酸鹽。
烷基苯磺酸鹽之具體例,可列舉十二烷基苯磺酸鈉鹽等。
烷基萘磺酸鹽之具體例,可列舉十二烷基萘磺酸鈉鹽等。
硫代琥珀酸二酯型之具體例,可列舉硫代琥珀酸二-2-乙基己酯鈉鹽等。
含有芳香環之化合物的磺酸鹽,可列舉烷基化二苯醚之單或二磺酸鹽、苯乙烯化苯酚磺酸鹽等。
磷酸酯鹽,可列舉高級醇磷酸酯鹽、及高級醇環氧乙烷加成物磷酸酯鹽。
高級醇磷酸酯鹽之具體例,可列舉月桂基醇磷酸單酯二鈉鹽、月桂基醇磷酸二酯鈉鹽等。
高級醇環氧乙烷加成物磷酸酯鹽之具體例,可列舉油醇環氧乙烷5莫耳加成物磷酸單酯二鈉鹽。
陽離子界面活性劑,可列舉四級銨鹽型、胺鹽型等。
四級銨鹽型,可列舉3級胺類與4級化劑(甲基氯化物、甲基溴化物、乙基氯化物、苄基氯化物、二甲基硫酸等之烷基化劑、環氧乙烷等)之反應所得,可列舉例如月桂基三甲基銨氯化物、二癸基二甲基銨氯化物、二辛基二甲基銨溴化物、十八烷基三甲基銨溴化物、月桂基二甲基苄基銨氯化物(苯扎氯銨(benzalkonium chloride))、西吡氯銨(cetylpyridinium chloride)、聚氧乙烯三甲基銨氯化物、硬脂醯胺乙基二乙基甲基銨甲基硫酸鹽(methosulfate)等。
胺鹽型,可列舉將1~3級胺類以無機酸(鹽酸、硝酸、硫酸、氫碘酸等)或有機酸(乙酸、甲酸、草酸、乳酸、葡萄糖酸、己二酸、烷基燐酸等)進行中和而得者。例如一級胺鹽型者,可列舉脂肪族高級胺(月桂基胺、十八烷基胺、鯨蠟胺(Cetylamine)、硬化牛脂胺、松香胺等之高級胺)之無機酸鹽或有機酸鹽、低級胺類之高級脂肪酸(硬脂酸、油酸等)鹽等。
二級胺鹽型者,可列舉例如脂肪族胺之環氧乙烷加成物等之無機酸鹽或有機酸鹽。
又,三級胺鹽型者,可列舉例如脂肪族胺(三乙基胺、乙基二甲基胺、N,N,N’,N’-四甲基乙二胺等)、脂肪族胺之環氧乙烷加成物、脂環式胺(N-甲基吡咯烷、N-甲基哌啶、N-甲基六亞甲基亞胺(hexamethyleneimine)、N-甲基嗎啉、1,8-二氮雙環(5,4,0)-7-十一碳烯等)、含氮雜環芳香族胺(4-二甲基胺基吡啶、N-甲基咪唑、4,4’-聯吡啶(dipyridyl)等)之無機酸鹽或有機酸鹽、三乙醇胺單硬脂酸酯、硬脂醯胺乙基二乙基甲基乙醇胺等之3級胺類之無機酸鹽或有機酸鹽等。
兩性界面活性劑,可列舉羧酸鹽型兩性界面活性劑、硫酸酯鹽型兩性界面活性劑、磺酸鹽型兩性界面活性劑、磷酸酯鹽型兩性界面活性劑等,羧酸鹽型兩性界面活性劑,可列舉胺基酸型兩性界面活性劑與甜菜鹼型兩性界面活性劑。
羧酸鹽型兩性界面活性劑,可列舉胺基酸型兩性界面活性劑、甜菜鹼型兩性界面活性劑、咪唑啉型兩性界面活性劑等,此等之中,胺基酸型兩性界面活性劑係分子內具有胺基與羧基之兩性界面活性劑,具體而言,可列舉例如烷基胺基丙酸型兩性界面活性劑(十八烷基胺基丙酸鈉、月桂基胺基丙酸鈉等)、烷基胺基乙酸型兩性界面活性劑(月桂基胺基乙酸鈉等)等。
甜菜鹼型兩性界面活性劑係分子內具有四級銨鹽型之陽離子部分與羧酸型之陰離子部分之兩性界面活性劑,可列舉例如烷基二甲基甜菜鹼(十八烷基二甲基胺基乙酸甜菜鹼、月桂基二甲基胺基乙酸甜菜鹼等)、醯胺甜菜鹼(椰子油脂肪酸醯胺丙基甜菜鹼等)、烷基二羥基烷基甜菜鹼(月桂基二羥基乙基甜菜鹼等)等。
此外,咪唑啉型兩性界面活性劑,可列舉例如2-十一烷基-N-羧基甲基-N-羥基乙基咪唑鎓(imidazolium)甜菜鹼等。
其他之兩性界面活性劑,可列舉例如月桂醯甘胺酸鈉(Sodium Lauroyl Glycine)、月桂醯二胺基乙基甘胺酸鈉、月桂基二胺基乙基甘胺酸鹽酸鹽、二辛基二胺基乙基甘胺酸鹽酸鹽等之甘胺酸型兩性界面活性劑、十五烷基硫代牛磺酸等之磺基甜菜鹼(sulfobetaine)型兩性界面活性劑等。
非離子界面活性劑,可列舉環氧烷加成型非離子界面活性劑及多元醇型非離子界面活性劑等。
環氧烷加成型非離子界面活性劑係對於高級醇、高級脂肪酸或烷基胺等直接加成環氧烷,或對於乙二醇類加成環氧烷所得之聚伸烷二醇類與高級脂肪酸等反應,或對於多元醇與高級脂肪酸反應所得之酯化物,加成環氧烷或對高級脂肪酸醯胺加成環氧烷所得者。
環氧烷,可列舉例如環氧乙烷、環氧丙烷及環氧丁烷。
環氧烷加成型非離子界面活性劑之具體例,可列舉氧化烯烷醚(例如辛基醇環氧乙烷加成物、月桂基醇環氧乙烷加成物、十八烷基醇環氧乙烷加成物、油醇環氧乙烷加成物、月桂醇環氧乙烷環氧丙烷嵌段加成物等)、聚氧化烯高級脂肪酸酯(例如十八烷基酸環氧乙烷加成物、月桂基酸環氧乙烷加成物等)、聚氧化烯多元醇高級脂肪酸酯(例如聚乙二醇之月桂酸二酯、聚乙二醇之油酸二酯、聚乙二醇之硬脂酸二酯等)、聚氧化烯烷基苯醚(例如壬基苯酚環氧乙烷加成物、壬基苯酚環氧乙烷環氧丙烷嵌段加成物、辛基苯酚環氧乙烷加成物、雙酚A環氧乙烷加成物、二壬基苯酚環氧乙烷加成物、苯乙烯化苯酚環氧乙烷加成物等)、聚氧化烯烷基胺醚(例如月桂基胺環氧乙烷加成物,十八烷基胺環氧乙烷加成物等)、聚氧化烯烷基烷醇醯胺(例如羥基乙基月桂酸醯胺之環氧乙烷加成物、羥基丙基油酸醯胺之環氧乙烷加成物、二羥基乙基月桂酸醯胺之環氧乙烷加成物等)。
多元醇型非離子界面活性劑,可列舉多元醇脂肪酸酯、多元醇脂肪酸酯環氧烷加成物、多元醇烷醚、多元醇烷醚環氧烷加成物。
多元醇脂肪酸酯之具體例,可列舉季戊四醇單月桂酸酯、季戊四醇單油酸酯、山梨糖醇酐單月桂酸酯、山梨糖醇酐單硬脂酸酯、山梨糖醇酐單月桂酸酯、山梨糖醇酐二月桂酸酯、山梨糖醇酐二油酸酯、蔗糖單硬脂酸酯等。
多元醇脂肪酸酯環氧烷加成物之具體例,可列舉乙二醇單油酸酯環氧乙烷加成物、乙二醇單硬脂酸酯環氧乙烷加成物、三羥甲基丙烷單硬脂酸酯環氧乙烷環氧丙烷無規加成物、山梨糖醇酐單月桂酸酯環氧乙烷加成物、山梨糖醇酐單硬脂酸酯環氧乙烷加成物、山梨糖醇酐二硬脂酸酯環氧乙烷加成物、山梨糖醇酐二月桂酸酯環氧乙烷環氧丙烷無規加成物等。
多元醇烷醚之具體例,可列舉季戊四醇單丁醚、季戊四醇單月桂醚、山梨糖醇酐單甲醚、山梨糖醇酐單十八烷醚、甲基糖苷(glycoside)、月桂基糖苷等。
多元醇烷醚環氧烷加成物之具體例,可列舉山梨糖醇酐單十八烷醚環氧乙烷加成物、甲基糖苷環氧乙烷環氧丙烷無規加成物、月桂基糖苷環氧乙烷加成物、十八烷基糖苷環氧乙烷環氧丙烷無規加成物等。
此等之中,本發明所使用的乳化劑,較佳為選自分散劑或非離子界面活性劑,更佳之乳化劑之具體例,本發明之CMP研磨墊用中空微球為由三聚氰胺樹脂、脲樹脂所構成時,作為乳化劑,較佳為苯乙烯-馬來酸酐共聚物、乙烯-馬來酸酐共聚物、異丁烯-馬來酸酐共聚物。將此等以氫氧化鈉等的鹼性化合物中和,成為高密度之陰離子性聚合物,三聚氰胺甲醛預聚物化合物或脲甲醛預聚物化合物,可進行聚合。
又,該CMP研磨墊用中空微球為由醯胺樹脂所構成時,較佳為丙烯酸鈉-丙烯酸酯共聚物。藉由選擇此等,可形成安定的乳膠。
本發明中,(a)成分或(c)成分所使用的有機溶劑,只要是溶解具有至少2個羧基的多官能羧酸化合物者時,即無特別限制,可列舉例如烴系、鹵化系、酮系溶劑等。
其中,由微球之內部去除該有機溶劑,作為中空微球,較佳為沸點為200℃以下者,更佳為沸點為150℃以下者。例示此等時,可列舉以下者。
(烴系)
可列舉n-己烷、n-庚烷、n-辛烷等之碳數為6~11之脂肪族烴、苯、甲苯、二甲苯等之芳香族烴、環己烷、環戊烷、甲基環己烷等之脂環式烴。
(鹵化系)
可列舉氯仿、二氯甲烷、四氯乙烷、單或二氯苯等。
(酮系)
可列舉甲基異丁酮等。
此等之有機溶劑可單獨使用,也可作為二種以上之混合溶劑。
本發明所使用的有機溶劑,其中,更佳為n-己烷、n-庚烷、n-辛烷、苯、甲苯、二甲苯等。
又,本發明中,為了使乳膠更安定化,在不損及本發明效果的範圍內,可將添加劑添加於水相中。這種添加劑,可列舉碳酸鈉、碳酸鈣、碳酸鉀、磷酸鈉、磷酸鉀、磷酸鈣、氯化鈉、氯化鉀等的水溶性鹽。此等的添加劑,可單獨使用或組合2種以上使用。
本發明中,可使用的觸媒,可使用以下者。
前述CMP研磨墊用中空微球為由醯胺樹脂所構成時所使用的醯胺化觸媒,可使用任意適當者,無特別限制可使用。具體例示時,可列舉硼或磷酸二氫鈉等。
本發明之CMP研磨墊用中空微球,適合作為CMP研磨墊用之中空微球,藉由構成CMP研磨墊之聚胺基甲酸酯(脲)樹脂中含有該中空微球,可以優異的製造安定性製造CMP研磨墊,此外,可作為展現了優異研磨特性的CMP研磨墊。
製作這種CMP研磨墊的方法,習知的方法無限制可採用,將含有本發明之CMP研磨墊用中空微球的聚胺基甲酸酯(脲)樹脂切斷,表面研磨,可作為在該聚胺基甲酸酯(脲)樹脂之研磨表面具有細孔的CMP研磨墊。
本發明之CMP研磨墊所使用的聚胺基甲酸酯(脲)樹脂,無特別限制,藉由習知的方法製作即可,可列舉例如(B)多官能異氰酸酯化合物(以下也稱為(B)成分)與(C)活性氫基,可列舉例如使包含具有2個以上之羥基、硫醇基及胺基的化合物(以下也稱為(C)成分)的聚合性組成物進行聚合的方法。
又,本發明中,聚胺基甲酸酯(脲)樹脂係指統稱聚胺基甲酸酯樹脂、聚脲樹脂、及聚胺基甲酸酯脲樹脂者。
以下分別詳細說明構成聚胺基甲酸酯(脲)樹脂的各成分。
<(B)多官能異氰酸酯化合物;(B)成分>
(B)多官能異氰酸酯化合物係具有至少2個之異(硫)氰酸酯基的化合物。
本說明書中,異(硫)氰酸酯基係指異氰酸酯基(NCO基)、或異硫氰酸酯基(NCS基)。(B)多官能異氰酸酯化合物,當然也選擇具有異氰酸酯基與異硫氰酸酯基兩者之基的化合物。因此,(B)多官能異氰酸酯化合物中之異(硫)氰酸酯基之數係指異氰酸酯基與異硫氰酸酯基之合計之數。
其中,較佳為分子內具有2~6個之異(硫)氰酸酯基的化合物,更佳為具有2~4個的化合物,又更佳為具有2~3個的化合物。
又,前述(B)成分,也可為後述之(B11)分子內,異(硫)氰酸酯基為2個之2官能異(硫)氰酸酯化合物(以下也稱為「(B11)成分」)與(C11)分子內具有2個活性氫基之含有2官能活性氫之化合物(以下也稱為「(C11)成分」)之反應來製造之(B1)胺基甲酸酯預聚物(以下也稱為「(B1)成分」)。相當於(B)成分之(B1)胺基甲酸酯預聚物係包含2個以上之未反應之異氰酸酯基或異硫氰酸酯基之一般使用者,無特別限制,本發明中也可使用,較佳為包含2個以上之異氰酸酯基之(B1)胺基甲酸酯預聚物。
又,前述(C11)成分中之活性氫基係選自羥基、硫醇基、胺基之基。
前述(B)成分,大分類時,可分類成脂肪族異氰酸酯、脂環族異氰酸酯、芳香族異氰酸酯、異硫氰酸酯、其他的異氰酸酯、(B1)胺基甲酸酯預聚物。又,前述(B)成分可使用1種類的化合物,也可使用複數種類的化合物。使用複數種類的化合物時,成為基準的質量係複數種類之化合物的合計量。此等(B)成分具體例示時,可列舉以下者。
脂肪族異氰酸酯;(B)成分
亞甲基二異氰酸酯、三亞甲基二異氰酸酯、四亞甲基二異氰酸酯、六亞甲基二異氰酸酯、八亞甲基二異氰酸酯、九亞甲基二異氰酸酯、2,2’-二甲基戊烷二異氰酸酯、2,2,4-三甲基六亞甲基二異氰酸酯、十亞甲基二異氰酸酯、丁烯二異氰酸酯、1,3-丁二烯-1,4-二異氰酸酯、2,4,4-三甲基六亞甲基二異氰酸酯、1,6,11-三甲基十一亞甲基二異氰酸酯、1,3,6-三甲基六亞甲基二異氰酸酯、1,8-二異氰酸酯-4-異氰酸酯甲基辛烷、2,5,7-三甲基-1,8-二異氰酸酯-5-異氰酸酯甲基辛烷、雙(異氰酸酯乙基)碳酸酯、雙(異氰酸酯乙基)醚、1,4-丁二醇二丙醚-ω,ω’-二異氰酸酯、離胺酸二異氰酸酯甲基酯、2,4,4,-三甲基六亞甲基二異氰酸酯等之2官能異氰酸酯(相當於構成下述詳述之(B1)胺基甲酸酯預聚物的(B11)成分)。
脂環族異氰酸酯;(B)成分
異佛爾酮二異氰酸酯、(雙環[2.2.1]庚烷-2,5-二基)雙亞甲基二異氰酸酯、(雙環[2.2.1]庚烷-2,6-二基)雙亞甲基二異氰酸酯、2β,5α-雙(異氰酸酯)降莰烷、2β,5β-雙(異氰酸酯)降莰烷、2β,6α-雙(異氰酸酯)降莰烷、2β,6β-雙(異氰酸酯)降莰烷、2,6-二(異氰酸酯甲基)呋喃、雙(異氰酸酯甲基)環己烷、二環己基甲烷-4,4’-二異氰酸酯、4,4-異亞丙基雙(環己基異氰酸酯)、環己烷二異氰酸酯、甲基環己烷二異氰酸酯、二環己基二甲基甲烷二異氰酸酯、2,2’-二甲基二環己基甲烷二異氰酸酯、雙(4-異氰酸酯-n-亞丁基)季戊四醇、二聚酸二異氰酸酯、2,5-雙(異氰酸酯甲基)-雙環[2,2,1]-庚烷、2,6-雙(異氰酸酯甲基)-雙環[2,2,1]-庚烷、3,8-雙(異氰酸酯甲基)三環癸烷、3,9-雙(異氰酸酯甲基)三環癸烷、4,8-雙(異氰酸酯甲基)三環癸烷、4,9-雙(異氰酸酯甲基)三環癸烷、1,5-二異氰酸酯十氫萘、2,7-二異氰酸酯十氫萘、1,4-二異氰酸酯十氫萘、2,6-二異氰酸酯十氫萘、雙環[4.3.0]壬烷-3,7-二異氰酸酯、雙環[4.3.0]壬烷-4,8-二異氰酸酯、雙環[2.2.1]庚烷-2,5-二異氰酸酯與雙環[2.2.1]庚烷-2,6-二異氰酸酯、雙環[2,2,2]辛烷-2,5-二異氰酸酯、雙環[2,2,2]辛烷-2,6-二異氰酸酯、三環[5.2.1.02.6
]癸烷-3,8-二異氰酸酯、三環[5.2.1.02.6
]癸烷-4,9-二異氰酸酯等之2官能異氰酸酯(相當於構成下述詳述之(B1)胺基甲酸酯預聚物的(B11)成分)。
2-異氰酸酯甲基-3-(3-異氰酸酯丙基)-5-異氰酸酯甲基-雙環[2,2,1]-庚烷、2-異氰酸酯甲基-3-(3-異氰酸酯丙基)-6-異氰酸酯甲基-雙環[2,2,1]-庚烷、2-異氰酸酯甲基-2-(3-異氰酸酯丙基)-5-異氰酸酯甲基-雙環[2,2,1]-庚烷、2-異氰酸酯甲基-2-(3-異氰酸酯丙基)-6-異氰酸酯甲基-雙環[2,2,1]-庚烷、2-異氰酸酯甲基-3-(3-異氰酸酯丙基)-5-(2-異氰酸酯乙基)-雙環[2,2,1]-庚烷、2-異氰酸酯甲基-3-(3-異氰酸酯丙基)-6-(2-異氰酸酯乙基)-雙環[2,1,1]-庚烷、2-異氰酸酯甲基-2-(3-異氰酸酯丙基)-5-(2-異氰酸酯乙基)-雙環[2,2,1]-庚烷、2-異氰酸酯甲基-2-(3-異氰酸酯丙基)-6-(2-異氰酸酯乙基)-雙環[2,2,1]-庚烷、1,3,5-三(異氰酸酯甲基)環己烷等之多官能異氰酸酯。
芳香族異氰酸酯;(B)成分
二甲苯二異氰酸酯(o-、m-,p-)、四氯-m-二甲苯二異氰酸酯、亞甲基二苯基-4,4’-二異氰酸酯、4-氯-m-二甲苯二異氰酸酯、4,5-二氯-m-二甲苯二異氰酸酯、2,3,5,6-四溴-p-二甲苯二異氰酸酯、4-甲基-m-二甲苯二異氰酸酯、4-乙基-m-二甲苯二異氰酸酯、雙(異氰酸酯乙基)苯、雙(異氰酸酯丙基)苯、1,3-雙(α,α-二甲基異氰酸酯甲基)苯、1,4-雙(α,α-二甲基異氰酸酯甲基)苯、α,α,α’,α’-四甲基二甲苯二異氰酸酯、雙(異氰酸酯丁基)苯、雙(異氰酸酯甲基)萘、雙(異氰酸酯甲基)二苯醚、雙(異氰酸酯乙基)苯二甲酸酯、2,6-二(異氰酸酯甲基)呋喃、伸苯基二異氰酸酯(o-,m-,p-)、甲伸苯基二異氰酸酯、乙基伸苯基二異氰酸酯、異丙基伸苯基二異氰酸酯、二甲基伸苯基二異氰酸酯、二乙基伸苯基二異氰酸酯、二異丙基伸苯基二異氰酸酯、三甲基苯三異氰酸酯、苯三異氰酸酯、1,3,5-三異氰酸酯甲基苯、1,5-萘二異氰酸酯、甲基萘二異氰酸酯、聯苯基二異氰酸酯、2,4-甲伸苯基二異氰酸酯、2,6-甲伸苯基二異氰酸酯、4,4’-二苯基甲烷二異氰酸酯、2,2’-二苯基甲烷二異氰酸酯、2,4’-二苯基甲烷二異氰酸酯、3,3’-二甲基二苯基甲烷-4,4’-二異氰酸酯、聯苄-4,4’-二異氰酸酯、雙(異氰酸酯苯基)乙烯、3,3’-二甲氧基聯苯基-4,4’-二異氰酸酯、苯基異氰酸酯甲基異氰酸酯、苯基異氰酸酯乙基異氰酸酯、四氫伸萘基二異氰酸酯、六氫化苯二異氰酸酯、六氫化二苯基甲烷-4,4’-二異氰酸酯、二苯醚二異氰酸酯、乙二醇二苯醚二異氰酸酯、1,3-丙二醇二苯醚二異氰酸酯、二苯甲酮二異氰酸酯、二乙二醇二苯醚二異氰酸酯、二苯并呋喃二異氰酸酯、咔唑二異氰酸酯、乙基咔唑二異氰酸酯、二氯咔唑二異氰酸酯、2,4-甲伸苯基二異氰酸酯、2,6-甲伸苯基二異氰酸酯等之2官能異氰酸酯(相當於構成下述詳述之(B1)胺基甲酸酯預聚物的(B11)成分)。
均三甲苯三異氰酸酯、三苯基甲烷三異氰酸酯、Polymeric MDI、萘三異氰酸酯、二苯基甲烷-2,4,4’-三異氰酸酯、3-甲基二苯基甲烷-4,4’,6-三異氰酸酯、4-甲基-二苯基甲烷-2,3,4’,5,6-五異氰酸酯等之多官能異氰酸酯化合物。
異硫氰酸酯;(B)成分
p-伸苯基二異硫氰酸酯、亞二甲苯基-1,4-二異硫氰酸酯、及次乙基二異硫氰酸酯等之2官能異硫氰酸酯(相當於構成下述詳述之(B1)胺基甲酸酯預聚物的(B11)成分)。
其他的異氰酸酯:(B)成分
其他的異氰酸酯,可列舉以六亞甲基二異氰酸酯或甲伸苯基二異氰酸酯等之二異氰酸酯類為主原料之具有縮二脲(biuret)結構、脲二酮結構、異氰脲酸酯結構(例如日本特開2004-534870號公報揭示脂肪族聚異氰酸酯之縮二脲結構、脲二酮結構、異氰脲酸酯結構之改性的方法)之多官能異氰酸酯或三羥甲基丙烷等之3官能以上之多元醇之加合物的多官能者等(成書(岩田敬治編 聚胺基甲酸酯樹脂手冊便覽 日刊工業新聞社(1987))等所揭示)。
(B1)胺基甲酸酯預聚物;兩末端具有異(硫)氰酸酯基的(B)成分
本發明中,藉由前述(B11)成分與後述(C11)成分之反應可製造之(B1)胺基甲酸酯預聚物也可作為(B)成分使用。
前述(B1)胺基甲酸酯預聚物,無特別限制,作為(B11)成分,特別是可使用以下例示之單體較佳。具體而言,使用1,5-萘二異氰酸酯、二甲苯二異氰酸酯(o-,m-,p-)、2,4-甲伸苯基二異氰酸酯、2,6-甲伸苯基二異氰酸酯、伸苯基二異氰酸酯(o-,m-,p-)、2,2’-二苯基甲烷二異氰酸酯、2,4’-二苯基甲烷二異氰酸酯、4,4’-二苯基甲烷二異氰酸酯、異佛爾酮 二異氰酸酯、1,3-雙(異氰酸酯甲基)環己烷、二環己基甲烷-4,4’-二異氰酸酯、(雙環[2.2.1]庚烷-2,5(2,6)-二基)雙亞甲基二異氰酸酯較佳。此等與(C11)成分反應,作為在兩末端具有異氰酸酯基及/或異硫氰酸酯基之(B1)成分較佳。
又,最終所得之前述聚胺基甲酸酯(脲)樹脂,為了發揮特別優異的特性,較佳為使用至少1種類之分子量(數平均分子量)為300~2000的(C11)成分,製造(B1)胺基甲酸酯預聚物。活性氫基係指羥基、硫醇基、胺基。其中,考慮反應性時,(C11)成分中之活性氫基,較佳為羥基。
前述分子量(數平均分子量)為300~2000的(C11)成分,可組合使用不同種類者,不同分子量者。又,為了調整最終所得之前述聚胺基甲酸酯(脲)樹脂之硬度或強度等,(B1)胺基甲酸酯預聚物,較佳為使用將分子量(數平均分子量)為300~2000的(C11)成分與該分子量(數平均分子量)為90~300的(C11)成分組合所製造者。此時,因使用之(C11)成分、及(B11)成分的種類、及彼等的使用量而異,分子量300~2000的(C11)成分設為100質量份時,分子量90~300的(C11)成分較佳為0~50質量份,分子量90~300的(C11)成分更佳為1~40質量份。
又,(B1)胺基甲酸酯預聚物,必須是分子的兩末端為異(硫)氰酸酯基。因此,(B1)胺基甲酸酯預聚物,較佳為(B11)成分中之異(硫)氰酸酯基之合計莫耳數(n5)與(C11)成分之活性氫基(羥基、硫醇基、或胺基)之合計莫耳數(n6)在1<(n5)/(n6)≦2.3的範圍內製造。2種類以上之使用分子的末端為(B11)成分時,該異(硫)氰酸酯基之莫耳數(n5)當然為(B11)成分之異(硫)氰酸酯基的合計莫耳數。又,2種類以上之(C11)成分之活性氫基的莫耳數(n6)當然為活性氫基之合計之活性氫的莫耳數。活性氫基為第一級胺基時,第一級胺基為1莫耳。換言之,第一級胺基中,第2個胺基(-NH)反應時,需要非常大的能量(即使第一級胺基,第2個之-NH反應困難)。因此,本發明中,即使使用具有第一級胺基之(C11)成分,第一級胺基可計算為1莫耳。
該(B1)胺基甲酸酯預聚物之異(硫)氰酸酯當量(異氰酸酯當量及/或異硫氰酸酯當量的總量),可藉由(B1)胺基甲酸酯預聚物所具有之異(硫)氰酸酯基依據JIS K 7301進行定量,而求得。該異(硫)氰酸酯基可藉由以下的逆滴定法定量。首先,使所得之(B1)胺基甲酸酯預聚物溶解於乾燥溶劑。其次,相較於(B1)胺基甲酸酯預聚物所具有之異(硫)氰酸酯基的量,明顯過剩量,且濃度為已知的二-n-丁基胺加入於該乾燥溶劑中,使(B1)胺基甲酸酯預聚物之全異(硫)氰酸酯基與二-n-丁基胺反應。接著,未被消耗之(未參與反應)二-n-丁基胺使用酸滴定,求被消耗之二-n-丁基胺的量。此消耗之二-n-丁基胺與(B1)胺基甲酸酯預聚物所具有之異(硫)氰酸酯基為同量,因此,可求得異(硫)氰酸酯當量。又,(B1)胺基甲酸酯預聚物係兩末端為異(硫)氰酸酯基之直鏈狀之胺基甲酸酯預聚物,因此,(B1)胺基甲酸酯預聚物之數平均分子量為異(硫)氰酸酯當量的2倍。此(B1)胺基甲酸酯預聚物的分子量容易與以膠體滲透層析(GPC)測定的值一致。又,例如併用該(B1)胺基甲酸酯預聚物與(B11)成分使用時,依據上述方法測定兩者的混合物即可。
前述(B1)胺基甲酸酯預聚物,無特別限制,異(硫)氰酸酯當量,較佳為300~5000,更佳為350~3000,特佳為350~2000。此理由雖不明,可考慮如下述。藉由使用(B1)胺基甲酸酯預聚物,前述聚胺基甲酸酯(脲)樹脂中之交聯點容易分散,可忽視,且均勻地存在,發揮安定的性能者。然後,使用(B1)胺基甲酸酯預聚物所得之前述聚胺基甲酸酯(脲)樹脂,製造時控制變得容易。例如,將本發明使用的聚合性組成物作為研磨墊使用時,變得適合使用。這種效果在併用(B1)胺基甲酸酯預聚物與(B11)成分時,聚異(硫)氰酸酯化合物之平均的異(硫)氰酸酯當量即使為300~5000,也能展現。但是僅(B1)胺基甲酸酯預聚物時,前述效果變得顯著。
本發明用之(B1)胺基甲酸酯預聚物之製造方法係使羥基、胺基、或硫醇基等之分子內具有2個活性氫基之(C11)成分與(B11)成分反應,製造分子之末端具有異氰酸酯基、或異硫氰酸酯基之(B1)胺基甲酸酯預聚物即可。可得到末端具有異氰酸酯基、或異硫氰酸酯基之預聚物時,即無特別限制。
如上述,為了得到(B1)胺基甲酸酯預聚物之較佳的(C11)成分與(B11)成分之調配量,如下述。具體而言,(B11)成分中之異(硫)氰酸酯基之莫耳數(n5)與(C11)成分之活性氫之莫耳數(n6)成為1<(n5)/(n6)≦2.3的範圍內製造為佳。
又,為了製造(B1)胺基甲酸酯預聚物時,反應中必要時可加熱或添加胺基甲酸酯化觸媒來製造。
本發明所使用的(B)成分,舉最佳之例時,就所形成之前述聚胺基甲酸酯(脲)樹脂的強度或反應性之控制的觀點,可列舉異佛爾酮 二異氰酸酯、1,3-雙(異氰酸酯甲基)環己烷、(雙環[2.2.1]庚烷-2,5(2,6)-二基)雙亞甲基二異氰酸酯之脂環族異氰酸酯、2,4-甲伸苯基二異氰酸酯、2,6-甲伸苯基二異氰酸酯、4,4’-二苯基甲烷二異氰酸酯、二甲苯二異氰酸酯(o-、m-,p-)之芳香族異氰酸酯、六亞甲基二異氰酸酯或甲伸苯基二異氰酸酯等之二異氰酸酯類作為主原料之縮二脲結構、脲二酮結構、異氰脲酸酯結構之多官能異氰酸酯、3官能以上之多元醇之加合物為多官能異氰酸酯、或(B1)胺基甲酸酯預聚物。
其中,可列舉特佳者為(B1)胺基甲酸酯預聚物。
<(C)具有2個以上之活性氫基的化合物;(C)成分>
(C)具有2個以上之活性氫基的化合物係至少1分子中具有2個以上選自由羥基、硫醇基及胺基所構成群組之基的化合物時,即無特別限制,可使用。當然,羥基、硫醇基及胺基之中,也可選擇具有任2個或全部之基的化合物。
其中,(C)成分,較佳為包含(CA)具有2個以上之胺基的化合物(以下也稱為(CA)成分),此外,更佳為包含(CB)具有3個以上之羥基及/或硫醇基的化合物(以下也稱為(CB)成分)。又,本說明書中,具有n個以上之羥基及/或硫醇基的化合物係指該化合物中之羥基與硫醇基之合計為n個以上,可為具有羥基,不具有硫醇基之化合物,也可為具有硫醇基,不具有羥基的化合物,也可為具有羥基與硫醇基兩者的化合物。
前述(CB)成分,特佳為具有5個以上之羥基及/或硫醇基的化合物。又,(CB)成分之質量中之羥基及/或硫醇基的莫耳數,較佳為0.5mmol/g~35mmol/g,更佳為0.8mmol/g~20mmol/g。
((CA)具有2個以上之胺基的化合物;(CA)成分)
(C)成分之中,(CA)具有2個以上之胺基的化合物,只要是一分子中具有2個以上之1級及/或2級之胺基的化合物時,即無特別限制,可使用。將前述具有2個以上之胺基的化合物大分類時,可分類為脂肪族胺、脂環族胺、芳香族胺、及具有可與異氰酸酯基聚合之胺基的聚輪烷。
脂肪族胺;(CA)成分
乙二胺、己二胺、九亞甲基二胺、十一烷亞甲基二胺、十亞甲基二胺、間二甲苯二胺、1,3-丙二胺、丁二胺等之2官能胺(相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分)。
二伸乙三胺等之多胺等之多官能胺。
脂環族胺;(CA)成分
異佛爾酮二胺、環己基二胺等之2官能胺(相當於構成前述(B1)胺基甲酸酯預聚物之(C11)成分)。
芳香族胺;(CA)成分
4,4’-亞甲基雙(o-氯苯胺)(MOCA)、2,6-二氯-p-伸苯基二胺、4,4’-亞甲基雙(2,3-二氯苯胺)、4,4’-亞甲基雙(2-乙基-6-甲基苯胺)、3,5-雙(甲硫基)-2,4-甲苯二胺、3,5-雙(甲硫基)-2,6-甲苯二胺、3,5-二乙基甲苯-2,4-二胺、3,5-二乙基甲苯-2,6-二胺、三亞甲基乙二醇-二-p-胺基苯甲酸酯、聚丁二醇-二-p-胺基苯甲酸酯、4,4’-二胺基-3,3’,5,5’-四乙基二苯基甲烷、4,4’-二胺基-3,3’-二異丙基-5,5’-二甲基二苯基甲烷、4,4’-二胺基-3,3’,5,5’-四異丙基二苯基甲烷、1,2-雙(2-胺基苯基硫)乙烷、4,4’-二胺基-3,3’-二乙基-5,5’-二甲基二苯基甲烷、N,N’-二-sec-丁基-4,4’-二胺基二苯基甲烷、3,3’-二乙基-4,4’-二胺基二苯基甲烷、m-苯二甲胺、N,N’-二-sec-丁基-p-伸苯基二胺、m-伸苯基二胺、p-苯二甲胺、p-伸苯基二胺、3,3’-亞甲基雙(甲基-6-胺基苯甲酸酯)、2,4-二胺基-4-氯苯甲酸-2-甲基丙基、2,4-二胺基-4-氯苯甲酸-異丙基、2,4-二胺基-4-氯苯基乙酸-異丙基、對苯二甲酸-二-(2-胺基苯基)硫乙基、二苯基甲烷二胺、甲伸苯基二胺、哌嗪等之2官能胺(相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分)。
1,3,5-苯三胺、三聚氰胺等之多官能胺。
具有胺基之聚輪烷;(CA)成分
本發明所使用之具有胺基的聚輪烷,無特別限定,可列舉例如國際申請第2018/092826號公報所記載的聚輪烷。
本發明所使用的(CA)成分之中,較佳者可列舉4,4’-亞甲基雙(o-氯苯胺)(MOCA)、4,4’-二胺基-3,3’-二乙基-5,5’-二甲基二苯基甲烷、3,5-二乙基甲苯-2,4-二胺、3,5-二乙基甲苯-2,6-二胺、3,5-雙(甲硫基)-2,4-甲苯二胺、3,5-雙(甲硫基)-2,6-甲苯二胺、三亞甲基乙二醇-二-p-胺基苯甲酸酯。
前述(C)成分之中,具有羥基及/或硫醇基的化合物,大分類時,可分類成脂肪族醇、脂環族醇、芳香族醇、聚酯多元醇、聚醚多元醇、聚己內酯多元醇、聚碳酸酯多元醇、聚丙烯酸多元醇、蓖麻油系多元醇、硫醇、OH/SH型含有聚合性基之單體、具有羥基及/或硫醇基之聚輪烷。具體例,可列舉如以下者。
((C)具有2個以上之羥基的化合物;(C)成分)
脂肪族醇;(C)成分
乙二醇、二乙二醇、丙二醇、二丙二醇、丁二醇、1,5-二羥基戊烷、1,6-二羥基己烷、1,7-二羥基庚烷、1,8-二羥基辛烷、1,9-二羥基壬烷、1,10-二羥基癸烷、1,11-二羥基十一烷、1,12-二羥基十二烷、新戊二醇、單油酸甘油基、單油酸甘油酯、聚乙二醇、3-甲基-1,5-二羥基戊烷、二羥基新戊基、2-乙基-1,2-二羥基己烷、2-甲基-1,3-二羥基丙烷等之2官能多元醇(相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分)。
丙三醇、三羥甲基乙烷、三羥甲基丙烷、二(三羥甲基丙烷)、三羥甲基丙烷三聚氧乙烯醚(例如日本乳化劑股份公司之TMP-30、TMP-60、TMP-90等)、丁烷三醇、1,2-甲基葡萄糖苷、季戊四醇、二季戊四醇、三季戊四醇、山梨醣醇、紅蘚醇、蘇糖醇、核糖醇、阿糖醇、木糖醇、蒜糖醇、鄰苯三酚、甜醇、艾杜糖醇、乙二醇、肌醇、己烷三醇、三丙三醇、二丙三醇、三乙二醇等之多官能多元醇(相當於前述(CB)成分)。
脂環族醇;(C)成分
氫化雙酚A、環丁二醇、環戊二醇、環己二醇、環庚二醇、環辛二醇、環己烷二甲醇、羥基丙基環己醇、三環[5,2,1,02,6
]癸烷-二甲醇、雙環[4,3,0]-壬二醇、二環己二醇、三環[5,3,1,13,9]十二烷二醇、雙環[4,3,0]壬烷二甲醇、三環[5,3,1,13,9
]十二烷-二乙醇、羥基丙基三環[5,3,1,13,9
]十二烷醇、螺[3,4]辛二醇、丁基環己二醇、1,1’-雙環己二醇、1,4-環己烷二甲醇、1,3-環己烷二甲醇、1,2-環己烷二甲醇、及o-二羥基亞二甲苯基等之2官能多元醇(相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分)。
三(2-羥基乙基)異氰脲酸酯、環己烷三醇、蔗糖、異麥芽酮糖醇、乳糖醇等之多官能多元醇(相當於前述(CB)成分)。
芳香族醇;(C)成分
二羥基萘、二羥基苯、雙酚A、雙酚F、亞二甲苯基乙二醇、四溴雙酚A、雙(4-羥基苯基)甲烷、1,1-雙(4-羥基苯基)乙烷、1,2-雙(4-羥基苯基)乙烷、雙(4-羥基苯基)苯基甲烷、雙(4-羥基苯基)二苯基甲烷、雙(4-羥基苯基)-1-萘基甲烷、1,1-雙(4-羥基苯基)-1-苯基乙烷、2-(4-羥基苯基)-2-(3-羥基苯基)丙烷、2,2-雙(4-羥基苯基)丁烷、1,1-雙(4-羥基苯基)丁烷、2,2-雙(4-羥基苯基)-3-甲基丁烷、2,2-雙(4-羥基苯基)戊烷、3,3-雙(4-羥基苯基)戊烷、2,2-雙(4-羥基苯基)己烷、2,2-雙(4-羥基苯基)辛烷、2,2-雙(4-羥基苯基)-4-甲基戊烷、2,2-雙(4-羥基苯基)庚烷、4,4-雙(4-羥基苯基)庚烷、2,2-雙(4-羥基苯基)十三烷、2,2-雙(4-羥基苯基)辛烷、2,2-雙(3-甲基-4-羥基苯基)丙烷、2,2-雙(3-乙基-4-羥基苯基)丙烷、2,2-雙(3-n-丙基-4-羥基苯基)丙烷、2,2-雙(3-異丙基-4-羥基苯基)丙烷、2,2-雙(3-sec-丁基-4-羥基苯基)丙烷、2,2-雙(3-tert-丁基-4-羥基苯基)丙烷、2,2-雙(3-環己基-4-羥基苯基)丙烷、2,2-雙(3-烯丙基-4’-羥基苯基)丙烷、2,2-雙(3-甲氧基-4-羥基苯基)丙烷、2,2-雙(3,5-二甲基-4-羥基苯基)丙烷、2,2-雙(2,3,5,6-四甲基-4-羥基苯基)丙烷、雙(4-羥基苯基)氰基甲烷、1-氰基-3,3-雙(4-羥基苯基)丁烷、2,2-雙(4-羥基苯基)六氟丙烷、1,1-雙(4-羥基苯基)環戊烷、1,1-雙(4-羥基苯基)環己烷、1,1-雙(4-羥基苯基)環庚烷、1,1-雙(3-甲基-4-羥基苯基)環己烷、1,1-雙(3,5-二甲基-4-羥基苯基)環己烷、1,1-雙(3,5-二氯-4-羥基苯基)環己烷、1,1-雙(3-甲基-4-羥基苯基)-4-甲基環己烷、1,1-雙(4-羥基苯基)-3,3,5-三甲基環己烷、2,2-雙(4-羥基苯基)降莰烷、2,2-雙(4-羥基苯基)金剛烷、4,4’-二羥基二苯醚、4,4’-二羥基-3,3’-二甲基二苯醚、乙二醇雙(4-羥基苯基)醚、4,4’-二羥基二苯硫醚、3,3’-二甲基-4,4’-二羥基二苯硫醚、3,3’-二環己基-4,4’-二羥基二苯硫醚、3,3’-二苯基-4,4’-二羥基二苯硫醚、4,4’-二羥基二苯基亞碸、3,3’-二甲基-4,4’-二羥基二苯基亞碸、4,4’-二羥基二苯基碸、4,4’-二羥基-3,3’-二甲基二苯基碸、雙(4-羥基苯基)酮、雙(4-羥基-3-甲基苯基)酮、7,7’-二羥基-3,3’,4,4’-四氫-4,4,4’,4’-四甲基-2,2’-螺雙(2H-1-苯并吡喃)、反式-2,3-雙(4-羥基苯基)-2-丁烯、9,9-雙(4-羥基苯基)茀、3,3-雙(4-羥基苯基)-2-丁酮、1,6-雙(4-羥基苯基)-1,6-己烷二酮、4,4’-二羥基聯苯、m-二羥基亞二甲苯基、p-二羥基亞二甲苯基、1,4-雙(2-羥基乙基)苯、1,4-雙(3-羥基丙基)苯、1,4-雙(4-羥基丁基)苯、1,4-雙(5-羥基戊基)苯、1,4-雙(6-羥基己基)苯、2,2-雙[4-(2”-羥基乙氧基)苯基]丙烷、及對苯二酚、間苯二酚等之2官能多元醇(相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分)。
三羥基萘、四羥基萘、苯三醇、聯苯四醇、鄰苯三酚、(羥基萘基)鄰苯三酚、三羥基菲等之多官能多元醇(相當於前述(CB)成分)。
聚酯多元醇;(C)成分
可列舉藉由多元醇與多元酸之縮合反應所得的化合物。其中,較佳為數平均分子量為400~2000,更佳為500~1500,最佳為600~1200。又,在分子之兩末端僅具有(分子內,2個之)羥基者,相當於構成前述(B1)胺基甲酸酯預聚物之(C11)成分,分子中具有3個以上之羥基者,相當於前述(CB)成分。
在此,前述多元醇,可列舉乙二醇、1,2-丙二醇、1,3-丁二醇、1,4-丁二醇、3-甲基-1,5-戊二醇、1,6-己二醇、3,3’-二羥甲基庚烷、1,4-環己烷二甲醇、新戊二醇、3,3-雙(羥基甲基)庚烷、二乙二醇、二丙二醇、丙三醇、三羥甲基丙烷等,此等可單獨使用,也可混合2種類以上使用。又,前述多元酸,可列舉琥珀酸、己二酸、壬二酸、癸二酸、十四烷二酸、環戊烷二羧酸、環己烷二羧酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、萘二甲酸等,此等可單獨使用,也可混合2種類以上使用。
此等聚酯多元醇,可以試劑或工業上取得,市售者例示時,可列舉DIC股份公司製「Polylite(註冊商標)」系列、Nippon Polyurethane工業股份公司製「Nipporan(註冊商標)」系列、川崎化成工業股份公司製「MAXIMOL(註冊商標)」系列、股份公司kuraray製「kuraray多元醇(註冊商標)」系列等。
聚醚多元醇;(C)成分
可列舉環氧烷之開環聚合、或分子中具有2個以上之活性氫基的化合物與環氧烷之反應所得的化合物及其改性體。其中,較佳為數平均分子量為400~2000,更佳為500~1500,最佳為600~1200。又,分子之兩末端僅有(分子內2個之)羥基者,相當於構成前述(B1)胺基甲酸酯預聚物之(C11)成分,分子中具有3個以上之羥基者,相當於前述(CB)成分。
在此,前述聚醚多元醇,可列舉聚合物多元醇、胺基甲酸酯改性聚醚多元醇、聚醚酯共聚物多元醇等,上述分子中具有2個以上之活性氫基的化合物,可列舉水、乙二醇、丙二醇、丁二醇、丙三醇、三羥甲基丙烷、己烷三醇、三乙醇胺、二丙三醇、季戊四醇、三羥甲基丙烷、己烷三醇等之分子中具有1個以上之羥基的乙二醇、丙三醇等之多元醇化合物,此等可單獨使用,也可混合2種類以上使用。
又,前述環氧烷,可列舉環氧乙烷、環氧丙烷、四氫呋喃等之環狀醚化合物,此等可單獨使用,也可混合2種類以上使用。
這種聚醚多元醇,可以試劑或工業上取得,市售者例示時,可列舉旭硝子股份公司製「excenol(註冊商標)」系列、「elmastar(註冊商標)」、股份公司ADEKA製「ADEKA polyether」系列等。
聚己內酯多元醇;(C)成分
可列舉藉由ε-己內酯之開環聚合所得的化合物。其中,較佳為數平均分子量為400~2000,更佳為500~1500,最佳為600~1200。又,分子之兩末端僅有(分子內2個之)羥基者,相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分,分子中具有3個以上之羥基者,相當於前述(CB)成分。
此等聚己內酯多元醇,可以試劑或工業上取得,市售者例示時,可列舉DAICEL化學工業股份公司製「Placcel(註冊商標)」系列等。
聚碳酸酯多元醇;(C)成分
可列舉將低分子多元醇之1種類以上進行光氣化所得的化合物或使用碳酸乙烯酯、碳酸二乙酯、二苯基碳酸酯等,進行酯交換所得的化合物。其中,較佳為數平均分子量為400~2000,更佳為500~1500,最佳為600~1200。又,分子之兩末端僅有(分子內2個之)羥基者,相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分,分子中具有3個以上之羥基者,相當於前述(CB)成分。
在此,前述低分子多元醇,可列舉乙二醇、1,2-丙二醇、1,3-丙二醇、2-甲基-1,3-丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、3-甲基-1,5-戊二醇、2-乙基-4-丁基-1,3-丙二醇、二乙二醇、二丙二醇、新戊二醇、環己烷-1,4-二醇、環己烷-1,4-二甲醇、二聚酸二醇、雙酚A之環氧乙烷或環氧丙烷加成物、雙(β-羥基乙基)苯、亞二甲苯基乙二醇、丙三醇、三羥甲基丙烷、季戊四醇等之低分子多元醇類。
聚丙烯酸多元醇;(C)成分
可列舉使(甲基)丙烯酸酯或使乙烯基單體聚合所得的多元醇化合物。又,分子之兩末端僅有(分子內2個之)羥基者,相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分,分子中具有3個以上之羥基者,相當於前述(CB)成分。
蓖麻油系多元醇;(C)成分
蓖麻油系多元醇,可列舉以天然油脂的蓖麻油為起始原料的多元醇化合物。又,分子之兩末端僅有(分子內2個之)羥基者,相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分,分子中具有3個以上之羥基者,相當於前述(CB)成分。
此等蓖麻油多元醇,可以試劑或工業上取得,市售者例示時,可列舉伊藤製油股份公司製「URIC(註冊商標)」系列等。
((C)具有2個以上之硫醇基的化合物;(C)成分)
前述(C)成分之中,具有硫醇基之化合物之較佳的具體例,可使用國際公開第WO2015/068798號小冊子所記載者。其中,特佳者例示時,可列舉以下者。
四乙二醇雙(3-巰基丙酸酯)、1,4-丁二醇雙(3-巰基丙酸酯)、1,6-己二醇雙(3-巰基丙酸酯)、1,4-雙(巰基丙基硫代甲基)苯(相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分)。
三羥甲基丙烷三(3-巰基丙酸酯)、季戊四醇四(3-巰基丙酸酯)、二季戊四醇六(3-巰基丙酸酯)、1,2-雙[(2-巰基乙基)硫代]-3-巰基丙烷、2,2-雙(巰基甲基)-1,4-丁烷二硫醇、2,5-雙(巰基甲基)-1,4-二噻烷、4-巰基甲基-1,8-二巰基-3,6-二硫辛烷(dithiaoctane)、1,1,1,1-四(巰基甲基)甲烷、1,1,3,3-四(巰基甲硫基)丙烷、1,1,2,2-四(巰基甲硫基)乙烷、4,6-雙(巰基甲硫基)-1,3-二噻烷、三-{(3-巰基丙醯氧基)乙基}-異氰脲酸酯(isocyanurate)等之硫醇(相當於前述(CB)成分)。
含有OH/SH型聚合性基之單體;(C)成分
前述(C)成分之中,羥基與硫醇基之兩者作為化合物,可列舉以下者。
2-巰基乙醇、1-羥基-4-巰基環己烷、2-巰基對苯二酚、4-巰基苯酚、1-羥基乙硫基-3-巰基乙硫基苯、4-羥基-4’-巰基二苯基碸、2-(2-巰基乙硫基)乙醇、二羥基乙基硫醚單(3-巰基丙酸酯)、二巰基乙烷單(水楊酸酯(Salicylate))(相當於構成前述(B1)胺基甲酸酯預聚物的(C11)成分)。
3-巰基-1,2-丙二醇、甘油二(巰基乙酸酯)、2,4-二巰基苯酚、1,3-二巰基-2-丙醇、2,3-二巰基-1-丙醇、1,2-二巰基-1,3-丁二醇、季戊四醇三(3-巰基丙酸酯)、季戊四醇單(3-巰基丙酸酯)、季戊四醇雙(3-巰基丙酸酯)、季戊四醇三(巰基乙酸酯)、季戊四醇五(3-巰基丙酸酯)、羥基甲基-三(巰基乙硫基甲基)甲烷、羥基乙硫基甲基三(巰基乙硫基)甲烷等之多官能OH/SH型含有聚合性基之單體(相當於前述(CB)成分)。
具有羥基及/或硫醇基的聚輪烷;(C)成分
聚輪烷係指鏈狀之軸分子貫通複數之環狀分子的環內,且軸分子之兩端鍵結大體積基,具有因立體障礙,環狀分子無法由軸分子穿過之結構之分子的複合體,也稱為超分子(Supramolecule)。本發明之(C)成分可使用的聚輪烷係具有可與異氰酸酯基聚合之羥基及/或硫醇基的聚輪烷,具有3個以上之羥基及/或硫醇基者,相當於前述(CB)成分。本發明之(C)成分使用之具有羥基及/或硫醇基的聚輪烷,無特別限定,例如國際申請第2018/092826號公報所記載的聚輪烷。
本發明所使用之(CB)成分之中較佳者,可列舉丙三醇、三羥甲基乙烷、三羥甲基丙烷、二(三羥甲基丙烷)、三羥甲基丙烷三聚氧乙烯醚(日本乳化劑股份公司之TMP-30)、羥基為3個以上的聚酯多元醇、羥基為3個以上的聚醚多元醇、羥基為3個以上的蓖麻油系多元醇、具有羥基及/或硫醇基之聚輪烷,具有3個以上之羥基及/或硫醇基的聚輪烷更佳。
<聚合性組成物之調配比例>
本發明所使用的聚合性組成物中,(B)成分與(C)成分之調配比例,無特別限制。其中,為了發揮優異的效果,該聚合性組成物中之(B)成分之異(硫)氰酸酯基之合計設為1莫耳時,(C)成分之活性氫基之合計莫耳數較佳為0.8~2.0莫耳。前述異(硫)氰酸酯基過多,或過少時,所得之聚胺基甲酸酯(脲)樹脂中,容易產生硬化不良,或耐摩耗性降低的傾向。更進一步,為了得到硬化狀態佳,均勻的狀態,且耐摩耗性優異的聚胺基甲酸酯(脲)樹脂時,前述異(硫)氰酸酯基之合計設為1莫耳時,前述活性氫基之合計莫耳數更佳為0.85~1.75莫耳,又更佳為0.9~1.5莫耳。又,算出(C)成分之活性氫基之全莫耳數時,使用(CA)具有2個以上之胺基的化合物時,具有2個以上之該胺基之化合物之活性氫之莫耳數與胺基之莫耳數相等。
又,本發明所使用的聚合性組成物中,硬化時,為了展現優異之研磨特性,因此,如前述,(C)成分,較佳為含有(CA)成分,此外,更佳為含有(CA)成分及(CB)成分。
亦即,本發明所使用的聚合性組成物,較佳為含有(B)成分及(CA)成分,更佳為含有(B)成分、(CA)成分、及(CB)成分。
例如,前述聚合性組成物中,含有(B)成分、(CA)成分、及(CB)成分時之各自的調配比例為(B)成分、(CA)成分、及(CB)成分之合計100質量份時,較佳為(B)成分含有60~95質量份,(CA)成分含有2~20質量份,(CB)成分含有1~30質量份,更佳為(B)成分含有70~85質量份,(CA)成分含有2~15質量份,(CB)成分含有3~25質量份。
<調配於聚合性組成物之其他的調配成分>
本發明所使用的聚合性組成物中,為了快速促進該聚合,可使用胺基甲酸酯或脲用反應觸媒。本發明適合使用的上述胺基甲酸酯或脲用反應觸媒,具體例可使用國際公開第WO2015/068798號所記載者。
此等胺基甲酸酯或脲用反應觸媒,各自可1種單獨使用,也可併用2種以上,其使用量可為所謂觸媒量,例如(B)成分與(C)成分之合計100質量份時,可為0.001~10質量份,特別是可為0.01~5質量份的範圍。
又,本發明所使用的聚合性組成物,在不損及本發明效果的範圍內。可使用公知的各種調配劑。例如,可添加研磨粒、抗氧化劑、紫外線吸收劑、紅外線吸收劑、著色防止劑、螢光染料、染料、光變色化合物、顏料、香料、界面活性劑、難燃劑、可塑劑、填充劑、抗靜電劑、泡沫穩定劑(foam stabilizer)、溶劑、平坦劑、其他的添加劑。此等之添加劑可單獨使用,也可併用2種以上。
本發明所使用的聚合方法,無特別限制,採用習知的方法即可。例如,可採用國際公開第WO2015/ 068798號、國際公開第WO2016/143910、WO2018-092826所記載的條件。具體而言,可使用一鍋法、預聚物法等之乾式法、及使用溶劑的濕式法等。其中,較佳為採用乾式法。
本發明之CMP研磨墊,只要含有本發明之中空微球與前述聚胺基甲酸酯(脲)樹脂時,無特別限制。其製法也無特別限制,其中,在含有前述(B)成分與(C)成分的聚合性組成物中,均勻混合‧分散本發明之中空微球後,進行聚合的方法較適合。
本發明之中空微球對聚胺基甲酸酯(脲)樹脂之調配量係以如前述的方法,(B)成分及(C)成分之合計100質量份時,較佳為本發明之中空微球為0.1~20質量份,更佳為0.2~15質量份,又更佳為0.5~10質量份。藉由在此範圍,可展現優異的研磨特性。
又,相對於聚胺基甲酸酯(脲)樹脂100質量份,本發明之CMP研磨墊中之中空微球之含量,較佳為0.1~20質量份,更佳為0.2~15質量份,又更佳為0.5~10質量份。藉由在此範圍,可展現優異的研磨特性。
本發明之CMP研磨墊,可使用經發泡的聚胺基甲酸酯(脲)樹脂。該發泡之聚胺基甲酸酯(脲)樹脂的密度,較佳為0.40~0.95g/cm3
。又,使聚胺基甲酸酯(脲)樹脂發泡的方法,可無限制使用習知的方法。例如添加水的發泡劑發泡法係水與異(硫)氰酸酯基反應後,生成二氧化碳與胺基。前述二氧化碳成為發泡氣體,前述胺基再與異(硫)氰酸酯基反應,形成脲鍵及/或硫脲鍵。
本發明之CMP研磨墊,可具有任意之適合的硬度。本發明中之硬度可依據蕭氏(Shore)法測定,例如可依據JIS規格(硬度試驗)K6253測定。本發明中,CMP研磨墊之蕭氏硬度,較佳為30A~70D,又更佳為40A~60D(又,「A」表示蕭氏「A」刻度(scale),「D」表示蕭氏「D」刻度的硬度)。亦即,例如,30A~70D係指蕭氏A硬度為30以上,且蕭氏D硬度為70以下。
硬度係必要時改變調配組成、及調配量,可形成任意的硬度。
此外,本發明之CMP研磨墊,在以下範圍的壓縮率展現被研磨物的平坦性上較佳。壓縮率可依據JIS L 1096之方法測定。前述壓縮率,較佳為0.5%~50%。藉由在上述範圍內,可展現優異之被研磨物的平坦性。
本發明之CMP研磨墊之耐摩耗性,較佳為Taber摩耗試驗中為60mg以下,又更佳為50mg以下。因Taber摩耗量變少,作為CMP研磨墊使用時,可展現優異的耐摩耗性。Taber摩耗試驗之詳細的實施方法,可使用後述實施例記載的方法。
又,本發明之CMP研磨墊,可以複數層所構成。此時,至少任一層可使用前述聚胺基甲酸酯(脲)樹脂。例如以2層構成CMP研磨墊時,進行研磨時,具有與被研磨物接觸之研磨面的研磨層(也稱為第1層)與以相對於前述第1層之研磨面的面,與前述第1層接觸之基底層(也稱為第2層)之2層構成。此時,藉由使第2層與第1層不同之硬度或彈性模數,可調整CMP研磨墊的特性。此時,基底層,較佳為硬度比研磨層小。本發明中,將前述聚胺基甲酸酯(脲)樹脂作為研磨層使用較合適,基底層也可使用前述聚胺基甲酸酯(脲)樹脂。
又,前述聚胺基甲酸酯(脲)樹脂係藉由使前述聚合性組成物含有研磨粒,進行聚合,可形成固定研磨粒聚胺基甲酸酯(脲)樹脂。前述研磨粒,可列舉例如選自由氧化鈰、氧化矽、氧化鋁、碳化矽、二氧化鋯、氧化鐵、二氧化錳、氧化鈦及金剛石之材料所構成的粒子、或由此等材料所構成之二種以上的粒子等。含有此等研磨粒的方法,無特別限定,例如上述聚合性組成物分散有此等研磨粒後,使該聚合性組成物聚合的方法。
本發明中,CMP研磨墊的樣態無特別限制,例如可在其表面形成溝構造。該CMP研磨墊之溝構造,較佳為將漿料(slurry)保持‧更新的形狀,具體而言,可列舉X(帶狀(Stripe))溝、XY格子溝、同心圓狀溝、貫通孔、未貫通之孔、多角柱、圓柱、螺旋狀溝、偏心圓狀溝、放射狀溝、及組合此等溝者。
又,上述CMP研磨墊之溝構造的製作方法,無特別限定。可列舉例如使用特定尺寸之切削工具進行機械切削的方法、將樹脂流入具有特定表面形狀的模具中,藉由使硬化,製作的方法、以具有特定表面形狀之壓製板,壓製樹脂進行製作的方法、使用光微影製作的方法、使用印刷手法製作的方法、藉由碳酸氣體雷射等雷射光之製作方法等。
[實施例]
其次,使用實施例及比較例,詳細地說明本發明,本發明不限於本實施例者。以下實施例及比較例中使用的各成分及評價方法係如下述。
[各成分]
(a)成分;有機溶劑
‧Tol;甲苯
(A)成分;乳化劑
‧聚乙烯-馬來酸酐(平均分子量為100,000~500,000)
‧PVA:完全皂化型,平均聚合度約500之聚乙烯醇
(聚合性單體)
‧三聚氰胺甲醛預聚物化合物
NikaresinS-260(NIPPON CARBIDE工業股份公司製);水溶性羥甲基三聚氰胺(三聚氰胺-甲醛初期縮合物)
‧脲
‧甲醛
‧間苯二甲酸二氯化物
‧p-伸苯基二胺
(B)成分
‧Pre-1;異氰酸酯當量為905之末端異氰酸酯胺基甲酸酯預聚物
(Pre-1之製造例)
在具備氮導入管、溫度計、攪拌機之燒瓶中,在氮環境下,使2,4-甲伸苯基二異氰酸酯:50g、聚氧丁二醇(數平均分子量;1,000):90g與二乙二醇:12g,在80℃下反應6小時,得到異氰酸酯當量為905之末端異氰酸酯胺基甲酸酯預聚物(Pre-1)。
‧Pre-2;異氰酸酯當量為460之兩末端具有異氰酸酯基的胺基甲酸酯預聚物
(Pre-2之製造例)
在具備氮導入管、溫度計、攪拌機之燒瓶中,在氮環境下,使2,4-甲伸苯基二異氰酸酯:1000g與聚丙二醇(數平均分子量;500):1100g,在80℃下反應4小時後,添加二乙二醇:120g,在80℃下,反應5小時,得到異(硫)氰酸酯當量為460之末端異氰酸酯胺基甲酸酯預聚物(Pre-2)。
(C)成分‧MOCA;4,4’-亞甲基雙(o-氯苯胺)((CA)成分)
‧HARDCURE30;Kumiai化學工業股份公司製二甲硫基甲苯二胺((CA)成分)
‧TMP;三羥甲基丙烷((CB)成分)
‧Poly♯10;伊藤製油股份公司製之POLYCASTOR♯10。活性氫基係單位重量為2.8mmol/g、羥基為5~6官能的蓖麻油系多元醇((CB)成分)。
‧RX-1;側鏈具有羥基,側鏈之分子量平均為約350、重量平均分子量為165,000的聚輪烷單體((CB)成分)
RX-1係如以下製造。
(1-1)PEG-COOH之調製;
準備分子量10,000之直鏈狀聚乙二醇(PEG)作為軸分子用聚合物,使PEG:10g、2,2,6,6-四甲基-1-哌啶氧基自由基:100mg、溴化鈉:1g溶解於水100mL中。此溶液中,添加次氯酸鈉水溶液(有效氯濃度5%):5mL,在室溫下攪拌10分鐘。然後,添加乙醇:5mL,結束反應。然後,使用二氯甲烷:50mL萃取後,餾除二氯甲烷,溶解於乙醇:250mL後,在-4℃之溫度下,再沉澱12小時,回收PEG-COOH,進行乾燥。
(1-2)聚輪烷之調製;
將上述所調製之PEG-COOH:3g及α-環糊精(α-CD):12g分別溶解於70℃的水50mL中,將所得之各溶液進行混合,充分搖混(shake)。接著,將此混合溶液在4℃之溫度,使再沉澱12小時,析出的包接錯合物進行凍結乾燥、回收。然後,室溫下,將金剛烷胺0.13g溶解於二甲基甲醯胺(DMF):50ml後,添加上述包接錯合物,快速地充分搖混。接著,再添加將苯并三唑-1-基-氧-三(二甲基胺基)鏻六氟磷酸酯試劑:0.38g溶解於DMF:5mL的溶液,充分搖混。再添加將二異丙基乙基胺:0.14ml溶解於DMF:5mL的溶液,充分搖混得到漿料狀的試劑。
上述所得之漿料狀的試劑,在4℃下靜置12小時。然後,添加DMF/甲醇混合溶劑(體積比1/1):50ml,進行混合、離心分離,去除上清液。進一步,藉由上述DMF/甲醇混合溶液洗淨後,使用甲醇進行洗淨、離心分離,得到沉澱物。所得的沉澱物以真空乾燥使乾燥後,溶解於二甲基亞碸(DMSO):50mL,將所得之透明溶液滴下至700mL的水中,使析出聚輪烷。將析出的聚輪烷以離心分離回收,真空乾燥。再溶解於DMSO中,在水中析出,進行回收、乾燥,得到純化聚輪烷。此時之α-CD之包接數為0.25。
在此,包接數係將聚輪烷溶解於DMSO-d6
,藉由1
H-NMR測定裝置(日本電子製JNM-LA500)測定,使用以下方法算出。
在此,X,Y及X/(Y-X)係表示以下的意義。
X:4~6ppm之來自環糊精之羥基之質子的積分值
Y:3~4ppm之來自環糊精及PEG之亞甲基鏈之質子的積分值
X/(Y-X):環糊精對PEG之質子比
首先,預先算出理論上最大包接數1時的X/(Y-X),由此值與實際之化合物的分析值算出的X/(Y-X)進行比較,算出包接數。
(1-3)末端羥基導入側鏈修飾聚輪烷(RX-1)之調製;
將上述純化的聚輪烷:500mg溶解於1mol/L之NaOH水溶液:50mL中,添加環氧丙烷:3.83g(66mmol),在氬環境下,室溫下攪拌12小時。接著,使用1mol/L的HCl水溶液,將上述聚輪烷溶液進行中和,使pH成為7~8,以透析軟管透析後,進行冷凍乾燥(freeze-drying),得到羥基丙基化聚輪烷。所得之羥基丙基化聚輪烷以1
H-NMR及GPC鑑定,確認具有所期望之結構的羥基丙基化聚輪烷。
又,藉由羥基丙基對環狀分子之羥基的修飾度為0.5,藉由GPC測定,重量平均分子量Mw:50,000。
調製將所得之羥基丙基化聚輪烷:5g在80℃溶解於ε-己內酯:15g的混合液。將此混合液在邊吹入乾燥氮,邊以110℃攪拌1小時後,加入2-乙基己酸錫(II)之50wt%二甲苯溶液:0.16g,130℃下攪拌6小時。然後,添加二甲苯,得到導入有不揮發濃度為約35質量%之側鏈的ε-己內酯修飾聚輪烷二甲苯溶液。
將上述調製之ε-己內酯修飾聚輪烷二甲苯溶液滴下至己烷中,進行回收、乾燥,得到ε-己內酯修飾聚輪烷(RX-1)。
[評價方法]
(1)密度:
使用東洋精機製之(DSG-1)測定密度(g/cm3
)。
(2)研磨速率:
使用下述條件,測定實施研磨時之研磨速率。研磨速率為2吋藍寶石晶圓10片之平均值。
CMP研磨墊:表面形成有同心圓狀之溝之大小500mmφ、厚度1mm的墊(pad)
漿料:FUJIMI COMPOL 80原液
壓力:4psi
旋轉數:45rpm
時間:1小時
(3)表面粗糙度(Ra):
將以上述(2)記載的條件研磨時之10片之2吋藍寶石晶圓的表面藉由Nano Search顯微鏡SFT-4500(股份公司島津製作所製)測定表面粗糙度(Ra)。表面粗糙度係2吋藍寶石晶圓10片的平均值。
(4)灰分:
將中空微球以600℃之溫度燃燒後之燃燒殘渣的質量與燃燒前之中空微球之質量的比例。
(5)耐刮痕性:
以上述(2)所記載的條件研磨後之2吋藍寶石晶圓確認刮痕之有無。評價係以下的基準實施。
1:以雷射顯微鏡測定,10片的晶圓全部無缺陷者
2:以雷射顯微鏡測定,10片的晶圓中,確認1~2片有缺陷者
3:以雷射顯微鏡測定,10片的晶圓中,確認3~5片有缺陷者
(6)D硬度:
依據JIS規格(硬度試驗)K6253,藉由高分子計器製之硬度計(Durometer)測定蕭氏D硬度。重疊使厚度成為6mm來測定。硬度比較低者,以蕭氏A硬度測定,硬度比較高者以蕭氏D硬度測定。
(7)耐摩耗性:
使用Taber公司製之5130型的裝置測定Taber摩耗。荷重為1Kg,旋轉速度為60rpm,旋轉數為1000旋轉,摩耗輪係以H-18實施Taber摩耗試驗,測定摩耗量。
<實施例1>
僅以甲苯:100質量份調製(a)成分。其次,在水:200質量份中混合聚乙烯-馬來酸酐:10質量份,將此混合液使用10%氫氧化鈉水溶液,調製成pH4,調製(A)成分。其次,將調製的(a)成分與(A)成分進行混合,使用高速剪切式分散機,在2,000rpm×10分鐘、25℃的條件下進行攪拌,調製O/W乳膠。調製的O/W乳膠中,加入三聚氰胺甲醛預聚物化合物的NikaresinS-260:9質量份,在65℃下攪拌24小時後,冷卻至30℃後,添加氨水直到pH7.5為止,得到樹脂膜為由三聚氰胺樹脂所構成的微球分散液。所得之微球分散液藉由過濾取出微球,溫度60℃下,真空乾燥24小時,得到中空微球。然後,藉由分級機過篩,得到中空微球1。
所得之中空微球1係由三聚氰胺樹脂所構成,平均粒徑為30μm,體積密度為0.13g/cm3
,灰分未測定。
<實施例2>
將脲:20質量份,37wt%甲醛水溶液:40.5質量份,25質量%氨水:2質量份邊攪拌,邊昇溫至70℃。同溫度下,保持1小時後,冷卻至30℃,得到含有脲甲醛預聚物化合物的水溶液。
另外,僅以甲苯:100質量份調製(a)成分。其次,在水:200質量份中混合苯乙烯馬來酸酐共聚物之鈉鹽:10質量份,將此混合液使用10%氫氧化鈉水溶液,調製成pH4.5,調製(A)成分。其次,將調製的(a)成分與(A)成分進行混合,使用高速剪切式分散機,在2,000rpm×10分鐘、25℃的條件下進行攪拌,調製O/W乳膠。調製的O/W乳膠中,加入上述調合之含有脲甲醛預聚物化合物的水溶液:45質量份,在65℃下攪拌24小時後,冷卻至30℃後,添加氨水直到pH7.5為止,得到脲樹脂所構成之微球分散液。所得之微球分散液藉由過濾取出微球,溫度60℃下,真空乾燥24小時,然後,藉由分級機過篩,得到中空微球4。
所得之中空微球4係由脲樹脂所構成,平均粒徑為20μm,體積密度為0.14g/cm3
,灰分未測定。
<實施例3>
混合間苯二甲酸二氯化物:40質量份、甲苯:50質量份,調製(c)成分。其次,在水:50質量份中加入PVA:2.5質量份與碳酸鈉:21質量份,調製(d)成分。其次,將調製之(c)成分與(d)成分混合,使用高速剪切式分散機,在2,000rpm×10分鐘、25℃的條件下進行攪拌,調製O/W乳膠。調製的O/W乳膠中,加入將p-伸苯基二胺:32質量份溶解於水:50質量份的水溶液,在50℃下攪拌24小時,得到聚醯胺樹脂所構成之微球分散液。所得之微球分散液藉由過濾取出微球,溫度60℃下,真空乾燥24小時,然後,藉由分級機過篩,得到中空微球5。
所得之中空微球5係由聚醯胺樹脂所構成,平均粒徑為35μm,體積密度為0.15g/cm3
,灰分未測定。
<參考例1>
將前述Pre-1:1質量份溶解於甲苯:15質量份,調製油相成分。其次,在水:150質量份中溶解PVA:10質量份,調製水相成分。其次,將調製的油相成分與水相成分混合,使用高速剪切式分散機,在2,000rpm×10分鐘、25℃的條件下進行攪拌,調製O/W乳膠。在25℃下,將乙二胺:0.05質量份溶解於水:30質量份的水溶液滴下至調製的O/W乳膠中。滴下後,25℃下緩慢攪拌60分鐘後,60℃下攪拌4小時,得到胺基甲酸酯(脲)樹脂所構成之微球分散液。所得之微球分散液藉由過濾取出微球,溫度60℃下,真空乾燥24小時,然後,藉由分級機過篩,得到中空胺基甲酸酯微球2。
所得之中空微球2係由胺基甲酸酯(脲)樹脂所構成,平均粒徑為25μm,體積密度為0.10g/cm3
,灰分未測定。
<參考例2>
中空微球3係市售之微囊920-40(日本fillite公司製、表面覆蓋無機粉體之丙烯腈樹脂所構成的中空微球),平均粒徑為40μm,體積密度為0.03g/cm3
,灰分為1.87質量份。
<實施例4>
使用上述製造的中空微球1,製作CMP研磨墊。
將4,4’-亞甲基雙(o-氯苯胺)(MOCA):12質量份在120℃下充分地脫氣,調製B液。另外,加熱至70℃之上述製造例1製造的Pre-1:88質量份中,加入實施例1所得之中空微球1:3.3質量份,以自轉公轉攪拌機攪拌,形成均勻溶液的A液。
在此,中空微球之安定性評價係藉由以下的2個方法,得到CMP研磨墊用聚胺基甲酸酯(脲)樹脂。
(製造方法1)
A液調合後,在70℃之加溫下,保溫30分鐘後,加入調製成120℃的B液,以自轉公轉攪拌機攪拌,形成均勻的聚合性組成物。將前述聚合性組成物注入模具,100℃使硬化15小時,得到聚胺基甲酸酯(脲)樹脂。
(製造方法2)
A液調合後,在70℃之加溫下,保溫6小時後,加入調製成120℃的B液,以自轉公轉攪拌機攪拌,形成均勻的聚合性組成物。將前述聚合性組成物注入模具,100℃使硬化15小時,得到聚胺基甲酸酯(脲)樹脂。
所得之聚胺基甲酸酯(脲)樹脂分別切薄片,得到表面形成有同心圓狀之溝之大小500mmφ,厚度1mm之由聚胺基甲酸酯(脲)樹脂所構成的CMP研磨墊,因A液之保溫時間差異,比較各自的物性。
上述所得之由聚胺基甲酸酯(脲)樹脂所構成之CMP研磨墊,(製造方法1)密度0.85g/cm3
、研磨速率2.1μm/hr、被研磨物之晶圓研磨後的表面粗糙度0.25nm,(製造方法2)密度0.85g/cm3
、研磨速率2.1μm/hr、被研磨物之晶圓研磨後的表面粗糙度0.25nm,無差異。
<實施例5>
除了將RX-1:24質量份與4,4’-亞甲基雙(o-氯苯胺)(MOCA):5質量份,以120℃混合形成均勻溶液後,充分地脫氣,調製B液,Pre-1使用71質量份外,與實施例1同樣的方法,製作由聚胺基甲酸酯(脲)樹脂所構成的CMP研磨墊,進行評價。結果記載於表1。
<實施例6~13、比較例1、2>
除使用表1所示的組成外,與實施例1同樣的方法,製作由聚胺基甲酸酯(脲)樹脂所構成的CMP研磨墊,進行評價。結果記載於表1。
由表1的結果得知,本發明之中空微球具有優異之研磨速率,可作為可更平滑地研磨被研磨物之晶圓的CMP研磨墊,又,相較於由聚胺基甲酸酯(脲)樹脂所構成的中空微球,即使與聚合性單體長時間調配,研磨特性也不會降低,可安定製造CMP研磨墊。
此外,作為具有含有可與異氰酸酯基聚合之活性氫之活性氫基的化合物,藉由將使用了具有含有可與異氰酸酯基聚合之活性氫之活性氫基之聚輪烷的聚胺基甲酸酯(脲)樹脂,用於CMP研磨墊基材,可展現更優異的研磨特性。
Claims (9)
- 一種CMP研磨墊用中空微球,其係由選自由三聚氰胺樹脂、脲樹脂,及醯胺樹脂所成群組之至少1種樹脂所構成之平均粒徑為1~100μm。
- 如請求項1之CMP研磨墊用中空微球,其中前述中空微球之體積密度(bulk density) 為0.01~0.6g/cm3 。
- 如請求項1或2之CMP研磨墊用中空微球,其中該中空微球設為100質量份時,前述中空微球之灰分(ash)為0.5質量份以下。
- 一種CMP研磨墊,其係由包含如請求項1~3中任一項之CMP研磨墊用中空微球與聚胺基甲酸酯(脲)樹脂而成。
- 如請求項4之CMP研磨墊,其中蕭氏硬度(shore D hardness)為30A~70D。
- 如請求項4或5之CMP研磨墊,其中前述聚胺基甲酸酯(脲)樹脂為使含有(B)多官能異氰酸酯化合物與(CA)具有2個以上之胺基之化合物的聚合性組成物,進行聚合的樹脂。
- 如請求項4~6中任一項之CMP研磨墊,其中前述聚胺基甲酸酯(脲)樹脂為使含有(B)多官能異氰酸酯化合物、(CA)具有2個以上之胺基之化合物及(CB)具有3個以上之羥基及/或硫醇基之化合物的聚合性組成物,進行聚合的樹脂。
- 如請求項7之CMP研磨墊,其中前述聚合性組成物中之前述(B)多官能異氰酸酯化合物、前述(CA)具有2個以上之胺基之化合物,及前述(CB)具有3個以上之羥基及/或硫醇基之化合物之調配比例為(B)成分、(CA)成分,及(CB)成分之合計100質量份時,(B)成分為60~95質量份,(CA)成分為2~20質量份,及(CB)成分為1~30質量份。
- 如請求項7或8之CMP研磨墊,其中前述(CB)具有3個以上之羥基及/或硫醇基之化合物為具有3個以上之羥基及/或硫醇基的聚輪烷(polyrotaxane)。
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SE540837C2 (en) * | 2013-12-26 | 2018-11-27 | Matsumoto Yushi Seiyaku Kk | Process for producing heat-expandable microspheres and application thereof |
JP6749755B2 (ja) * | 2015-11-30 | 2020-09-02 | 富士紡ホールディングス株式会社 | 研磨用保持具及びその製造方法 |
JP2017177301A (ja) * | 2016-03-31 | 2017-10-05 | 富士紡ホールディングス株式会社 | 研磨パッド |
CN109790274B (zh) * | 2016-11-17 | 2021-11-02 | 株式会社德山 | 使用聚轮烷的氨基甲酸酯树脂、以及抛光垫 |
CN106891246B (zh) * | 2017-03-30 | 2019-05-07 | 湖北鼎龙控股股份有限公司 | 一种用于半导体、光学材料和磁性材料表面平坦化的化学机械抛光垫 |
JP7137301B2 (ja) * | 2017-09-29 | 2022-09-14 | 富士紡ホールディングス株式会社 | 研磨パッド |
SG11202009860PA (en) * | 2018-04-10 | 2020-11-27 | Tokuyama Corp | Urethane resin using polyrotaxane, and pad for polishing |
JP7141283B2 (ja) * | 2018-09-06 | 2022-09-22 | 富士紡ホールディングス株式会社 | 研磨パッド、研磨パッドの製造方法、及び被研磨物の表面を研磨する方法 |
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2021
- 2021-03-31 US US17/915,006 patent/US20230151179A1/en active Pending
- 2021-03-31 WO PCT/JP2021/013796 patent/WO2021201088A1/ja active Application Filing
- 2021-03-31 TW TW110111892A patent/TW202204461A/zh unknown
- 2021-03-31 KR KR1020227033542A patent/KR20220161318A/ko unknown
- 2021-03-31 CN CN202180025673.0A patent/CN115379926A/zh active Pending
- 2021-03-31 JP JP2022512611A patent/JPWO2021201088A1/ja active Pending
Also Published As
Publication number | Publication date |
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CN115379926A (zh) | 2022-11-22 |
KR20220161318A (ko) | 2022-12-06 |
WO2021201088A1 (ja) | 2021-10-07 |
US20230151179A1 (en) | 2023-05-18 |
JPWO2021201088A1 (zh) | 2021-10-07 |
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