TW202231679A - 交聯的具有醯胺基團與羧基和/或其銨鹽的重複單元和α-單烯烴的重複單元的共聚物 - Google Patents
交聯的具有醯胺基團與羧基和/或其銨鹽的重複單元和α-單烯烴的重複單元的共聚物 Download PDFInfo
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Abstract
本揭露關於一種共聚物A,其具有(i)至少一種帶有醯胺基團與羧基和/或其銨鹽的重複單元,(ii)至少一種得自直鏈或支化的C2-C18 α-單烯烴的重複單元,和(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。本揭露還關於包含由本發明黏合劑形成的組分的製品。
Description
本揭露關於一種共聚物A,其具有(i)至少一種帶有醯胺基團與羧基和/或其銨鹽的重複單元,(ii)至少一種得自直鏈或支化的C2-C18 α-單烯烴的重複單元,和(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。本揭露還關於包含共聚物A的黏合劑以及包含由本發明的黏合劑形成的組分的製品。
在目前的黏合劑,特別是用於人造板生產的黏合劑中,以甲醛為原料製備的“三醛膠”(脲醛樹脂、酚醛樹脂和三聚氰胺甲醛樹脂)佔有較大的比重,超過80%。“三醛膠”製備簡單,價格低廉,但這類板材在使用過程中會長期釋放游離甲醛,污染室內環境,嚴重威脅居民的身體健康。
一些文獻中對減少“三醛膠”型人造板的甲醛釋放量提出過解決方案,例如CN 107033309 A試圖藉由調控原料的配比和各個聚合階段的pH值,
加入甲醛捕捉劑等方法來減少甲醛釋放。CN 203344147 U公開了,在板材的生產中,混入活性炭,竹炭,矽藻土等,賦予板材一定的氣體吸附能力。但是,上述的方法並沒有從根本上解決問題,板材在使用過程中仍有甲醛釋放。
以大豆蛋白、單寧、澱粉、明膠等生物質原料為基礎製備的黏合劑不涉及甲醛的使用,但是生物質原料降解速度快,又帶來了板材易老化的問題。雖然藉由添加抗老化劑能在一定程度上延緩降解,但是生物質材類黏合劑仍然有成本較高和資源方面的問題。這也限制了其實際使用。
另外,也可以利用如聚氯乙烯,高分子量聚乙烯,氯丁橡膠等聚合物進行板材的生產,但是這些聚合物都不具有水溶性,不能形成水性黏合劑,只能藉由熱熔或者有機溶劑將聚合物與木材原料混合,仍然存在成本高、消耗能源和不環保的缺點。
因此,從安全環保、低生產成本、施加工藝簡便性以及成品耐久性等方面考慮,開發出一種新型無甲醛可用於黏合劑的共聚物顯得尤為重要。
鑑於現有技術的上述狀況,本發明的發明人對黏合劑領域的共聚物進行了廣泛而深入的研究,以期發現一種無甲醛釋放、低成本、施加簡便且性能優異的可用於黏合劑的共聚物。本發明人發現了一種特定的共聚物A和包含該特定共聚物A的黏合劑,該黏合劑不僅無甲醛釋放、成本低、施加簡便且具有優異的性能。
本發明正是基於以上發現得以完成。
本發明的目的是提供一種共聚物A。
本發明的另一目的是提供一種包含共聚物A的黏合劑,該黏合劑具有安全環保、低成本、施加簡便和性能優異的優點。
本發明的另一目的是提供一種包含由本發明的黏合劑形成的組分的製品。
實現本發明目的的技術方案可以概括如下:
1.一種共聚物A,其具有
(i)至少一種帶有醯胺基團與羧基和/或其銨鹽的重複單元,
(ii)至少一種得自直鏈或支化的C2-C18 α-單烯烴的重複單元,和
(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。
2.根據第1項的共聚物A,其中在該共聚物A中,重複單元(i)的量為10-80重量%,較佳20-80重量%或22-79重量%,基於共聚物A的重複單元的總量。
3.根據第1或2項的黏合劑,其中該直鏈或支化的C2-C18 α-單烯烴為直鏈或支化的C2-C12 α-單烯烴,較佳直鏈或支化的C2-C8 α-單烯烴。
4.根據第1至3項中任一項的共聚物A,其中在該共聚物A中,重複單元(ii)的量為10-75重量%,較佳15-74重量%或20-70重量%,基於共聚物A的重複單元的總量。
5.根據第1至4項中任一項的共聚物A,其中該具有至少兩個碳-碳不飽和雙鍵的單體中的碳-碳不飽和雙鍵選自(甲基)丙烯酸酯基團、(甲基)丙烯醯胺基團、乙烯基、烯丙基以及鏈烯或環烯中的碳-碳雙鍵。
6.根據第1至5項中任一項的共聚物A,其中在該共聚物A中,重複單元(iii)的量為0.1-70重量%,較佳0.1-30重量%,基於共聚物A的重複單元的總量。
7.根據第1至6項中任一項共聚物A,其中該共聚物A衍生自共聚物B,該共聚物B具有:
(i’)至少一種帶有酸酐基團的重複單元,
(ii)至少一種得自直鏈或支化的C2-C18 α-單烯烴的重複單元,和
(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。
8.根據第7項的共聚物A,其中該共聚物B的帶有酸酐基團的重複單元(i’)得自至少一種具有碳-碳不飽和雙鍵和酸酐基團的單體。
9.根據第8項的共聚物A,其中該具有碳-碳不飽和雙鍵和酸酐基團的單體選自具有4-8個碳原子的單烯屬不飽和二羧酸酐,較佳馬來酸酐、衣康酸酐、檸康酸酐和亞甲基丙二酸酐,更佳馬來酸酐。
10.根據第1至9項中任一項的共聚物A,其中該共聚物A得自共聚物B與氨的反應。
11.一種包含第1至10項中任一項的共聚物A的黏合劑。
12.根據第11項的黏合劑,其中該黏合劑呈固體,較佳粉末形式;或者呈含水組成物,較佳呈水溶液形式,較佳該共聚物A的含量為2-40重量%,尤其是5-30重量%,基於含水組成物的總重量。
13.根據第11或12項的黏合劑,其中該黏合劑不含能夠與共聚物A的醯胺基團和/或羧基發生共價交聯反應的有機交聯劑。
14.一種包含由第11至13項中任一項的黏合劑形成的組分的製品。
15.根據第14項的製品,其中該製品為人造板、紙張、布或塗料。
16.根據第15項的製品,其中該製品為由木素纖維素材料和該黏合劑形成的人造板。
17.根據第16項的製品,其中該黏合劑用作基體樹脂,較佳該黏合劑填充木素纖維素材料之間的縫隙。
18.根據第14至17項中任一項的製品,其中以固含量計的黏合劑用量基於製品的總重量為1-45重量%,較佳2-35重量%,更佳3-30重量%。
19.根據第14至18項中任一項的製品,其中如第1-10項中任一項所定義的共聚物A的用量基於製品的總重量為1-40重量%,較佳2-30重量%,更佳3-25重量%。
20.如第11至13項中任一項的黏合劑在製備人造板、紙張、布或塗料中的用途。
圖1為實施例3中不同聚合物的紅外譜圖,由下往上分別為1:交聯的異丁烯-馬來酸酐共聚物的紅外譜圖;2:轉化為醯胺酸的共聚物的紅外譜圖;3:熱壓後的共聚物的紅外譜圖。
本文對相關特徵公開具體值(包括所公開範圍的端點值)可以相互結合成新的範圍。
共聚物A
本發明的一個方面關於一種共聚物A,其具有
(i)至少一種帶有醯胺基團與羧基和/或其銨鹽的重複單元,
(ii)至少一種得自直鏈或支化的C2-C18 α-單烯烴的重複單元,和
(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。
根據本發明,共聚物A中的重複單元(i)不同於重複單元(ii)和重複單元(iii)。
根據本發明,共聚物A的重複單元(i)中的羧基的一部分(例如1-10重量%)可以呈其銨鹽的形式。
所屬技術領域具有通常知識者可以理解,表述“得自”還包括共聚物具有某種重複單元,但是該重複單元並非直接由該重複單元對應的單體形成的情形。例如羧基亞乙基重複單元()可以得自丙烯酸的聚合,也可藉由將丙烯酸酯聚合,然後水解而得到。
在本發明的一個實施方案中,重複單元(i)的量可以為10-80重量%,例如20-80重量%、22-79重量%、22-78重量%、25-75重量%、30-70重量%或35-65重量%,基於共聚物A的重複單元的總量。
根據本發明,該至少一種重複單元(ii)得自直鏈或支化的C2-C18 α-單烯烴。該直鏈或支化的C2-C18 α-單烯烴可以為直鏈或支化的C2-C16 α-單烯烴或C4-C16 α-單烯烴,直鏈或支化的C2-C14 α-單烯烴或C4-C14 α-單烯烴,
直鏈或支化的C2-C12 α-單烯烴或C4-C12 α-單烯烴,直鏈或支化的C2-C10 α-單烯烴或C4-C10 α-單烯烴,較佳直鏈或支化的C2-C8 α-單烯烴或C4-C8 α-單烯烴。
這些直鏈或支化的C2-C18 α-單烯烴的具體實例可以提及乙烯、丙烯、1-丁烯、異丁烯、1-戊烯、1-己烯、1-辛烯、1-癸烯、1-十二碳烯、1-十四碳烯、1-十六碳烯和1-十八碳烯。
在該共聚物A中,重複單元(ii)的量可以為10-75重量%、15-74重量%、17-73重量%、20-70重量%、25-65重量%或30-60重量%,基於共聚物A的重複單元的總量。
根據本發明,該至少一種重複單元(iii)得自具有至少兩個碳-碳不飽和雙鍵的單體。根據本發明的一個實施方案,該具有至少兩個(如2-4個)碳-碳不飽和雙鍵的單體中的碳-碳不飽和雙鍵選自(甲基)丙烯酸酯基團、(甲基)丙烯醯胺基團、乙烯基、烯丙基以及鏈烯或環烯中的碳-碳雙鍵。
該重複單元(iii)的量可以為0.1-70重量%,例如0.1-30重量%、0.2-20重量%、0.2-10重量%或0.5-5重量%,基於共聚物A的重複單元的總量。
由於共聚物A具有至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元(iii),共聚物A一般是交聯的。
根據本發明,共聚物A可視需要含有補充重複單元。該補充重複單元例如可以選自得自如下單體的重複單元:
單烯屬不飽和C3-C8單羧酸、單烯屬不飽和C3-C8單羧酸的C1-C10烷基酯、單烯屬不飽和C3-C8單羧酸的醯胺、具有C1-C8烷基的乙烯基烷基醚、苯乙烯、非α-單烯烴的C4-C22單烯烴、被一個或多個選自C1-C12烷基、C1-C12烷氧基和
鹵素的取代基取代的苯乙烯、C1-C20羧酸的乙烯基酯、乙烯基吡咯烷酮、(甲基)丙烯腈、包含羥基的烯屬不飽和單體、N-乙烯基甲醯胺、乙烯基咪唑、烯丙苯、茚、甲茚和含呋喃環的化合物,
或者
該補充重複單元得自源自汽油、C4餾分、C5餾分、C8餾分、C9餾分或煤焦油輕餾分的反應物料的至少一種含碳-碳不飽和雙鍵的單體。
關於這些重複單元(i)的單體、以及重複單元(ii)的單體、重複單元(iii)的單體以及補充重複單元的單體以及反應物料的細節在下文中如對共聚物B詳細描述。
根據本發明的一個較佳實施方案,該共聚物A衍生自共聚物B,該共聚物B具有:
(i’)至少一種帶有酸酐基團的重複單元,
(ii)至少一種得自直鏈或支化的C2-C18 α-烯烴的重複單元,和
(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。
在一個較佳實施方案中,該共聚物A得自該共聚物B與氨的反應。
根據本發明的一個較佳實施方案,其中該共聚物B的帶有酸酐基團的重複單元(i’)得自至少一種具有碳-碳不飽和雙鍵和酸酐基團的單體。根據本發明,該具有碳-碳不飽和雙鍵和酸酐基團的單體可以選自具有4-8個碳原子的單烯屬不飽和二羧酸酐,較佳馬來酸酐、衣康酸酐、檸康酸酐、亞甲基丙二酸酐及其混合物,更佳馬來酸酐。
在共聚物B中,重複單元(i’)的量可以為10-80重量%,例如20-80重量%、22-79重量%、22-78重量%、25-75重量%、30-70重量%或35-65重量%,基於共聚物B的重複單元的總量。
共聚物B中的重複單元(ii)如上對共聚物(A)所述。在該共聚物B中,重複單元(ii)的量可以為10-75重量%、15-74重量%、17-73重量%、20-70重量%、25-65重量%或30-60重量%,基於共聚物B的重複單元的總量。
根據本發明,該至少一種重複單元(iii)得自具有至少兩個碳-碳不飽和雙鍵的單體。根據本發明的一個實施方案,該具有至少兩個(如2-4個)碳-碳不飽和雙鍵的單體中的碳-碳不飽和雙鍵選自(甲基)丙烯酸酯基團、(甲基)丙烯醯胺基團、乙烯基、烯丙基以及鏈烯或環烯中的碳-碳雙鍵。
該具有至少兩個碳-碳不飽和雙鍵的單體例如可以選自具有至少2個羥基的醇的(甲基)丙烯酸酯、具有至少2個羥基的醇的乙烯基醚、具有至少2個羥基的醇的烯丙基醚、氧化乙烯和/氧化丙烯低聚物的二(甲基)丙烯酸酯、(甲基)丙烯酸酯乙烯酯、(甲基)丙烯酸酯烯丙酯、亞甲基二(甲基)丙烯醯胺、具有至少兩個乙烯基的芳族化合物和C4-C22二烯。
該具有至少兩個羥基的醇例如可以具有2-6個,較佳2-4個羥基。這些醇可以選自具有2-6個碳原子的二元醇如乙二醇、丙二醇、丁二醇、戊二醇和己二醇、甘油、三羥甲基丙烷和季戊四醇等。
因此,具有至少2個羥基的醇的(甲基)丙烯酸酯,可以為含有2-6個碳原子的二元醇的二(甲基)丙烯酸酯,其可選自乙二醇二丙烯酸酯、乙二醇二甲基丙烯酸酯、1,2-丙二醇二丙烯酸酯、1,2-丙二醇二甲基丙烯酸酯、丁二醇二(甲基)丙烯酸酯、如丁烷-1,4-二醇二丙烯酸酯、丁烷-1,4-二醇二甲基丙烯酸酯、
己二醇二丙烯酸酯、己二醇二甲基丙烯酸酯、新戊二醇二丙烯酸酯、新戊二醇二甲基丙烯酸酯、3-甲基戊二醇二丙烯酸酯和3-甲基戊二醇二甲基丙烯酸酯。
氧化乙烯和/或氧化丙烯低聚物的二(甲基)丙烯酸酯的實例為二甘醇二丙烯酸酯、二甘醇二甲基丙烯酸酯、三甘醇二丙烯酸酯、三甘醇二甲基丙烯酸酯、四甘醇二丙烯酸酯和四甘醇二甲基丙烯酸酯。
具有至少兩個乙烯基的芳族化合物的實例可以提及二乙烯基苯、二乙烯基甲苯、三乙烯基苯和二乙烯基萘等。
C4-C22二烯可以是鏈二烯或環二烯。該C4-C22二烯可以是共軛或非共軛的。該C4-C22二烯例如為共軛或非共軛的C4-C16或C5-C16鏈二烯或環二烯,共軛或非共軛的C4-C12或C5-C12鏈二烯或環二烯,共軛或非共軛的C4-C8或C5-C8鏈二烯或環二烯;以及具有8-20個碳原子,較佳8-16或8-12個碳原子的雙環烯,如雙環戊二烯系單體,如雙環戊二烯、甲基雙環戊二烯(如2-甲基雙環戊二烯、5-甲基雙環戊二烯)、乙基雙環戊二烯(如2-乙基雙環戊二烯)和5,5-二甲基雙環戊二烯等。
C4-C22鏈二烯或環二烯的具體實例可以提及1,3-丁二烯、1,3-戊二烯、異戊二烯、1,3-己二烯、環戊二烯、甲基環戊二烯、1,3-環己二烯、1,4-戊二烯、1,4-己二烯、1,5-己二烯、1,4-環己二烯、1,5-環辛二烯等。
具有至少兩個(如2-4個)碳-碳不飽和雙鍵的單體其他具體實例可以提及三羥甲基丙烷三(甲基)丙烯酸酯、丁二醇二乙烯基醚、三羥甲基丙烷三乙烯基醚、季戊四醇三烯丙基醚、亞甲基二(甲基)丙烯醯胺、鄰苯二甲酸二烯丙基酯等。
該重複單元(iii)的量可以為0.1-70重量%,例如0.1-30重量%、0.2-20重量%、0.2-10重量%或0.5-5重量%,基於共聚物B的重複單元的總量。
根據本發明,共聚物B可視需要含有補充重複單元。該補充重複單元例如可以選自得自如下單體的重複單元:
單烯屬不飽和C3-C8單羧酸、單烯屬不飽和C3-C8單羧酸的C1-C10烷基酯、單烯屬不飽和C3-C8單羧酸的醯胺、具有C1-C8烷基的乙烯基烷基醚、苯乙烯、非α-單烯烴的C4-C22單烯烴、被一個或多個選自C1-C12烷基、C1-C12烷氧基和鹵素的取代基取代的苯乙烯、C1-C20羧酸的乙烯基酯、乙烯基吡咯烷酮、(甲基)丙烯腈、包含羥基的烯屬不飽和單體、N-乙烯基甲醯胺、乙烯基咪唑、烯丙苯、茚、甲茚和含呋喃環的化合物,
或者
該補充重複單元得自源自汽油、C4餾分、C5餾分、C8餾分、C9餾分或煤焦油輕餾分的反應物料的至少一種含碳-碳不飽和雙鍵的單體。
作為單烯屬不飽和C3-C8單羧酸的實例可以提及如丙烯酸、甲基丙烯酸、巴豆酸和乙烯基乙酸,較佳丙烯酸和甲基丙烯酸。
單烯屬不飽和C3-C8單羧酸的C1-C10烷基酯的實例可以提及C1-C10烷基的(甲基)丙烯酸烷基酯,尤其是甲基丙烯酸甲酯、丙烯酸甲酯、丙烯酸正丁酯、丙烯酸乙酯和丙烯酸2-乙基己酯或其混合物。
作為單烯屬不飽和C3-C8單羧酸的醯胺的實例尤其可以提及(甲基)丙烯醯胺。
作為具有C1-C8烷基的乙烯基烷基醚,較佳可以提及具有C1-C4烷基的乙烯基烷基醚,如甲基乙烯基醚、乙基乙烯基醚、異丁基乙烯基醚、正丁基
乙烯基醚、第三丁基乙烯基醚、正戊基乙烯基醚、異戊基乙烯基醚、正己基乙烯基醚、正辛基乙烯基醚和2-乙基己基乙烯基醚。
非α-單烯烴的C4-C22單烯烴可以是鏈烯和環烯,例如具有4-20或5-20個碳原子,如4-16或5-16個碳原子,或4-8或5-8個碳原子的鏈烯或環烯,如2-丁烯、2-戊烯、2-甲基-2-丁烯、環戊烯、環己烯、環庚烯等;具有5-20個碳原子,較佳5-16或8-12個碳原子的二氫雙環烯,特別是二氫雙環戊二烯(如2,3-二氫雙環戊二烯)、二氫甲基雙環戊二烯和二氫二甲基雙環戊二烯等。
對於被一個或多個選自C1-C12烷基、C1-C12烷氧基和鹵素的取代基取代的苯乙烯,其中的烷基或烷氧基較佳具有1-10個碳原子,如1-4個碳原子;其中的鹵素較佳為氯和溴。具體實例可以提及乙烯基甲苯(如α-甲基苯乙烯和對甲基苯乙烯)、α-丁基苯乙烯、4-正丁基苯乙烯、4-正癸基苯乙烯、對甲氧基苯乙烯、氯苯乙烯和溴苯乙烯。
C1-C20羧酸的乙烯基酯的實例可以提及月桂酸乙烯酯、硬脂酸乙烯酯、丙酸乙烯酯、新癸酸乙烯基酯和乙酸乙烯酯。
包含羥基的烯屬不飽和單體例如包括(甲基)丙烯酸C1-C10羥烷基酯,例如丙烯酸羥乙酯、甲基丙烯酸羥乙酯、丙烯酸2-羥丙酯、丙烯酸3-羥丙酯、甲基丙烯酸2-羥丙酯和甲基丙烯酸3-羥丙酯。
含呋喃環的化合物的實例可以提及呋喃環被一個或多個(如2-4個)選自C1-C12烷基和C1-C12羥烷基的取代基取代的單體,如糠醇,該呋喃環還可以進一步與苯環稠合,例如甲基苯并呋喃。
在本發明的一個實施方案中,可以不經過分離直接使用包含該至少一種含碳-碳不飽和雙鍵的單體以及飽和烴、不參與聚合的其他雜質的反應物料,
例如汽油、C4餾分、C5餾分、C8餾分、C9餾分、煤焦油輕餾分,以得到補充重複單元。在使用這些反應物料形成共聚物B時(如經由自由基聚合),這些反應物料中的含碳-碳不飽和雙鍵的單體之外的成分可以用作製備過程中的溶劑。當使用這些餾分作為反應物料時,可以進一步降低本發明黏合劑和人造板的成本。
作為C4餾分可以提及作為石油裂解或催化裂化制乙烯產生的副產物,其通常含異丁烯、1-丁烯-1、2-丁烯和丁烷等組分。
C4餾分可以具有如下具體組成:
C5餾分通常為來自石油裂解的C5餾分。C5餾分中含有約45-55%的二烯烴和8-15%的單烯烴。C5餾分中的其他組分包括18-25%的烷烴、1%左右的炔烴、10-20%的C4、苯和其他組分。
C5餾分可以具有如下具體組成:
C8和C9餾分主要來源於蒸汽裂解製乙烯工藝和石腦油鉑重整工藝,還有一部分來源於甲苯歧化或烷基轉移產物及煤焦油等。
C8餾分中通常包含22-35%的單烯烴,例如苯乙烯、烯丙苯、乙烯基甲苯、茚、甲茚。C8餾分中的其他組分包括45-55%的芳烴以及約20%的其他未知組分。
C8餾分可以具有如下具體組成:
C9餾分中通常含有20-30%的單烯烴(如苯乙烯、烯丙苯、乙烯基甲苯、茚)、8-15%的二烯。C9餾分中的其他組分包括約5%的烷烴、40-50%的芳烴以及10%左右的其他未知組分。C9餾分可以具有如下具體組成:
煤焦油中的輕油組分主要含苯乙烯、α-甲基苯乙烯、烷基苯、乙烯基甲苯、雙環戊二烯、苯并呋喃、茚、甲茚和甲基苯并呋喃等,目前主要作為深色-淺色的古馬隆樹脂原料。煤焦油輕餾分可以具有如下具體組成:
製備共聚物B的聚合可以使用油溶性自由基引發劑進行。該油溶性自由基引發劑例如包括偶氮類引發劑或者過氧化物引發劑。該偶氮類引發劑包括:偶氮二異丁腈、偶氮二異庚腈、偶氮二異丁酸二甲酯等;該過氧化物引發劑包括:過氧化二苯甲醯、過氧化二異丙苯、過氧化二(2,4-二氯苯甲醯)、過氧化二第三丁基、過氧化十二醯、過氧化苯甲酸第三丁酯、過氧化二碳酸二異丙基酯和過氧化二碳酸二環己酯等。該引發劑的用量基於單體重量為0.05-10重量%,較佳0.5-6重量%。
聚合反應可以在溶劑存在下進行。溶劑可以包括芳烴,烷烴與酮的混合物,羧酸酯,烷烴和芳烴等混合物,芳烴和羧酸酯的混合物,或者烷烴與羧酸酯的混合物,或者烷烴、芳烴和羧酸酯的混合物。
芳烴的實例可以提及甲苯、二甲苯和乙苯等。
羧酸酯可以包括C1-C6羧酸的C1-C8烷基酯、苯基酯或苄基酯以及具有6-10個碳原子的芳族羧酸的C1-C8烷基酯,具體實例可以提及甲酸乙酯、甲酸丙酯、甲酸異丁酯、甲酸戊酯、乙酸乙酯、乙酸丁酯、乙酸異丁酯、乙酸戊酯、乙酸異戊酯、乙酸苄酯、乙酸苯酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸丁酯、丁酸甲酯、丁酸乙酯、丁酸丙酯、丁酸丁酯、丁酸異丁酯、丁酸異戊酯、異丁酸乙酯、異戊酸乙酯、異戊酸異戊酯、苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸丁酯、苯甲酸異戊酯、苯乙酸甲酯、苯乙酸乙酯、苯乙酸丙酯、苯乙酸丁酯、苯乙酸異戊酯等酯類溶劑。
烷烴與酮的混合物中的酮可以選自丙酮、丁酮、環己酮、甲基異丁基酮、甲基異丙基酮,該烷烴可以選自正戊烷、正己烷、環己烷、正庚烷、正辛烷和異辛烷等。在烷烴與酮的混合物中,酮通常占5-65體積%。
聚合反應可以在惰性氣體如氮氣存在下進行。聚合反應的溫度通常為55-120℃,較佳60-100℃;聚合反應的時間通常為1-12小時,較佳2-8小時。在聚合反應之後,可以將所得共聚物B分離和乾燥。
在一個較佳實施方案中,該聚合反應藉由沉澱聚合進行。該沉澱聚合可以藉由選擇能夠溶解單體但是不能溶解所得共聚物B的溶劑而進行。藉由沉澱聚合,可以直接得到粉末形式的共聚物B。
根據本發明,如果使用汽油、C4餾分、C5餾分、C8餾分、C9餾分和煤焦油輕餾分作為反應物料的話,反應完成後未反應的烷烴或芳烴混合物只需簡單蒸餾即可分離,進而得到各種高附加值的溶劑和工業原料。
根據本發明,該共聚物B可以藉由與氨反應而得到共聚物A(在下文中進一步詳細描述)。
黏合劑
本發明的一個方面關於包含本發明共聚物A的黏合劑。
在本發明的黏合劑中,除了共聚物A之外,需要的話,本發明的黏合劑還可以包含至少一種添加劑。該添加劑可以是下面的一種或多種:除氧劑、乳化劑、染料、顏料、防遷移助劑、UV吸收劑、生物殺傷劑、消泡劑、著色劑、抗靜電劑和抗氧化劑。
根據一個實施方案,本發明的黏合劑不含能夠與共聚物A的醯胺基團和/或羧基發生共價交聯反應的有機交聯劑,如多元醇,多胺,多鏈烷醇胺或它們的混合物。
根據本發明,該黏合劑可以呈固體,較佳粉末形式;或者呈含水組成物,較佳呈水溶液形式。
在本發明的黏合劑中,共聚物A的量基於黏合劑的總量(如果黏合劑呈液態,如含水組成物或水溶液,則基於固含量)可以為30-100重量%,如50-100重量%,60-100重量%,70-100重量%,80-100重量%,或50-98重量%,或60-90重量%。
若該黏合劑呈含水組成物,較佳水溶液的形式,黏合劑的固含量可以為2-40重量%,或5-30重量%,或8-25重量%。
製備黏合劑的方法
本發明的一個方面涉及一種製備本發明的黏合劑的方法,其包括使共聚物B在反應介質(如水)存在或不存在下與氨反應。
共聚物B可以藉由與氨反應,即氨解形成共聚物A。該反應通常包括使共聚物B在低於100℃,較佳15-70℃的溫度下,例如在室溫下在含水介質中與氨在攪拌下反應。反應時間通常為0.1-10小時,較佳0.5-6小時。
在反應之後,所得反應混合物通常為含水組成物,較佳呈水溶液形式。所得含水組成物,較佳水溶液可以直接用作黏合劑。也可將反應混合物與上述至少一種添加劑混合後用作黏合劑。
較佳共聚物B與氨反應之前呈粉末的形式。較佳該粉末形式的共聚物B可以藉由沉澱聚合製備。粉末形式的共聚物B也可藉由將共聚物B(例如塊狀)研磨成粉末形式而得到。該粉末形式的共聚物B的平均粒徑可以為0.01-10μm,較佳0.05-8μm,更佳0.1-5μm。該粉末形式的共聚物A的平均粒徑可以為0.01-10μm,較佳0.05-8μm,更佳0.1-5μm。
固體形式的共聚物B與氨反應時間通常為2-300分鐘,如5-120分鐘。
在具體應用時,可以將固體形式的共聚物A溶於水中,視需要與上述至少一種添加劑混合後再施加。
共聚物B的酸酐基團的轉化率通常超過90%,較佳超過95%,更佳超過98%,如100%。
在共聚物B與氨的反應中,羧基還可以與氨形成銨鹽。
包含由本發明的黏合劑形成的組分的製品
本發明的一個方面關於包含由本發明黏合劑形成的組分的製品。
根據本發明,該製品可以為人造板、紙張、布或塗料。
在本發明的製品中,其中以固含量計的黏合劑用量基於製品的總重量可為1-45重量%,較佳2-40重量%,更佳3-35重量%或4-30重量%,如5-25重量%,6-25重量%,7-25重量%,8-19重量%。
在本發明的製品中,共聚物A用量基於製品的總重量可為1-40重量%,較佳2-30重量%,更佳3-25重量%或4-20重量%,如5-20重量%,6-20重量%或7-18重量%。
在一個實施方案中,該製品為由木素纖維素材料和本發明黏合劑形成的人造板。本發明的人造板應在寬的意義上理解,即由任何木素纖維素材料和本發明的黏合劑形成的板材。本發明的人造板並不局限於僅僅由木材形成的那些,還可以包括由竹子和秸稈等如下所述材料形成的板材。本發明的人造板可以是各種類型的人造板。在一個實施方案中,該人造板包括但不限於刨花板、膠合板、纖維板、密度板、秸稈板和指接板。
木素纖維素材料可以得自各種木素纖維素材料,例如木材、竹子、甘蔗渣、秸稈(如麥稈)、亞麻殘渣、堅果殼、穀粒殼等,以及它們的混合物。其中木材包括各種軟木和/或硬木。
木素纖維素材料可以呈鋸末、碎料、木片、條料、薄片、纖維、片材、木屑、刨花、顆粒和類似材料形式以及這些材料的組合的形式如條料和鋸末的組合。
木素纖維素材料可以藉由各種常規技術進行加工。可以將大木料在圓木刨片機中加工為木片。也可將大塊木料和邊角料切成碎料。還可將大木料在環形刨片機中刨片。通常在刨片之前將大木料去皮。
木素纖維素材料的尺寸通常並不關鍵。針對不同類型的人造板可以使用不同的尺寸。例如木素纖維素材料的尺寸可以為1-30目,較佳2-15目。對於片材類的木素纖維素材料,片材的厚度可以例如為0.5mm-5cm,較佳1mm-3cm。
在本發明的人造板中,該黏合劑用作基體樹脂,較佳該黏合劑填充木素纖維素材料之間的縫隙。
本發明的另一方面關於一種製備本發明製品的方法,該方法包括使用本發明的黏合劑。
根據本發明,人造板可以藉由如下方法製備,該方法包括將木素纖維素材料和本發明的黏合劑的混合物在105-300℃的溫度下和在0.4-10MPa的壓力下壓製,較佳壓製2-60分鐘,更佳壓製3-30分鐘,例如5-30分鐘。
用於壓製的木素纖維素材料和本發明的黏合劑的混合物可以藉由將木素纖維素材料與本發明的黏合劑混合而製備。當黏合劑為固體時,可以首先將黏合劑溶於水中後再與木素纖維素材料混合。
在壓製之前,較佳除去木素纖維素材料和黏合劑的混合物中的一部分水分,例如將木素纖維素材料和黏合劑的混合物的水份含量降至低於30重量%,較佳低於25重量%,例如低於22重量%,或低於18重量%。該混合物的水份含量通常高於5重量%或高於8重量%。該水份的除去可以藉由加熱進行,例如加熱溫度可以為50-90℃,較佳60-80℃。
在一個較佳實施方案中,該壓製在120-220℃的溫度下和/或在1-6MPa的壓力下進行。
當共聚物A具有呈其銨鹽形式的羧基時,羧基的銨鹽在壓製條件下又分解為羧基。
黏合劑的用途
最後,本發明還關於本發明的黏合劑在製備人造板、紙張、布或塗料中的用途。
包含本發明共聚物A的黏合劑安全、環保,沒有甲醛等有毒有害物質的釋放,施加簡單且成本低,同時本發明的黏合劑性能優異,特別適用於人造板、紙張、布或塗料的製造,尤其是木素纖維素基人造板的製造,並且用本發明的黏合劑製造的製品具有優異的機械性能和耐水性。
[實施例]
以下結合本發明中的具體實施例,對本發明中的技術方案進一步描述,但不應將其理解為對本發明保護範圍的限制。以下所描述的實施例僅是本
發明一部分實施例,並非全部的實施例。基於本發明中所列舉的實施例,所屬技術領域具有通常知識者在沒有採用創造性勞動的前提下所提出的其他實施例,均屬於本發明保護的範圍。除非另有說明,實施例中的百分數為重量百分數,實施例中的份數為質量份。
實施例1:乙烯共聚物體系
按照質量份數,將5.8份乙烯,19.6份馬來酸酐,0.3份交聯劑二乙烯基苯,300份苯和0.5份偶氮二異丁腈在高壓反應釜內混合溶解,升溫至70℃反應6小時。將產物離心分離,用苯洗滌,乾燥後獲得粉末狀產物為交聯的乙烯-馬來酸酐共聚物,其中馬來酸酐單元質量分數約為78%。
將10份該乙烯-馬來酸酐共聚物,5份37%氨水,85份水在室溫下攪拌4小時,獲得質量濃度10%的乙烯-馬來醯胺酸共聚物(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)懸浮液。將該懸浮液與楊木刨花(含水量5%,5-10目)混合均勻,每100份刨花中該共聚物用量8份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量15%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度170℃,壓力0.4MPa,熱壓時間15分鐘,獲得厚度為3mm刨花板。
實施例2:(正丁烯共聚物體系)
按照質量份數,將11.2份正丁烯,19.6份馬來酸酐,0.4份交聯劑雙甲基丙烯酸乙二醇酯,300份乙酸異戊酯和0.7份偶氮二異丁腈在高壓反應釜內混合溶解,升溫至70℃反應6小時。將產物離心分離、洗滌、乾燥後獲得粉末狀產物為交聯的正丁烯-馬來酸酐共聚物,其中馬來酸酐單元質量分數約為64%。
將10份該正丁烯-馬來酸酐共聚物,5份37%氨水,85份水在室溫下攪拌4小時,獲得質量濃度10%的正丁烯-馬來醯胺酸共聚物(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)懸浮液。將該懸浮液與楊木刨花(含水量5%,5-10目)混合均勻,每100份刨花中該共聚物用量8份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量10%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度160℃,壓力0.8MPa,熱壓時間12分鐘,獲得厚度為3mm刨花板。
實施例3:(異丁烯共聚物體系)
按照質量份數,將11.2份異丁烯,19.6份馬來酸酐,0.4份交聯劑雙甲基丙烯酸乙二醇酯,300份乙酸異戊酯和0.6份偶氮二異丁腈在高壓反應釜內混合溶解,升溫至70℃反應6小時。將產物離心分離、洗滌、乾燥後獲得粉末狀產物為交聯的異丁烯-馬來酸酐共聚物,其中馬來酸酐單元質量分數約為64%。
將10份該異丁烯-馬來酸酐共聚物,5份37%氨水,85份水在室溫下攪拌4小時,獲得質量濃度10%的異丁烯-馬來醯胺酸共聚物(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)懸浮液。將該懸浮液與楊木刨花(含水量5%,5-10目)混合均勻,每100份刨花中該共聚物用量8份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量15%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度170℃,壓力0.4MPa,熱壓時間15分鐘,獲得厚度為3mm刨花板。
圖1中由下往上分別為1:交聯的異丁烯-馬來酸酐共聚物的紅外譜圖,2:轉化為醯胺酸的共聚物的紅外譜圖,3:熱壓後的共聚物的紅外譜圖,其中:
曲線1:1858cm-1,1778cm-1處為酸酐上兩個羰基C=O伸縮振動峰;
曲線2:1661cm-1處為醯胺C=O伸縮振動峰,1557cm-1處為羧酸鹽C=O振動峰,原來的酸酐基團特徵峰基本消失;
曲線3:1778cm-1,1715cm-1處為環狀醯亞胺的特徵峰。
實施例4:(1-戊烯共聚物體系)
按照質量份數,將14份1-戊烯,19.6份馬來酸酐,0.3份交聯劑二乙烯基苯,300份乙酸異戊酯和0.7份偶氮二異丁腈混合溶解,體系通氮氣20分鐘後在70℃反應6小時。將產物離心,洗滌,乾燥獲得白色粉末形式的交聯的1-戊烯-馬來酸酐共聚物,共聚物中馬來酸酐單體單元的質量百分數為58%。
將20份該1-戊烯-馬來酸酐共聚物,10份37%氨水,70份水在室溫下攪拌4小時,獲得質量濃度20%的1-戊烯-馬來醯胺酸共聚物懸浮液(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)。將該懸浮液與楊木刨花(含水量5%,5-10目)混合,每100份刨花中該共聚物用量12份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量20%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度180℃,壓力1MPa,熱壓時間15分鐘,獲得厚度為3mm刨花板。
實施例5:(1-癸烯共聚物體系)
按照質量份數,將28份1-癸烯,19.6份馬來酸酐,0.3份交聯劑二乙烯基苯,300份乙酸異戊酯和0.7份偶氮二異丁腈混合溶解,體系通氮氣20分鐘後在70℃反應6小時。將產物離心,洗滌,乾燥獲得白色粉末形式的交聯1-癸烯-馬來酸酐共聚物,共聚物中馬來酸酐單體單元的質量百分數為41%。
將20份該1-癸烯-馬來酸酐共聚物,10份37%氨水,70份水在室溫下攪拌4小時,獲得質量濃度20%的1-癸烯-馬來醯胺酸共聚物懸浮液(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)。將該懸浮液與楊木刨花(含水量5%,5-10目)混合,每100份刨花中該共聚物用量12份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量10%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度160℃,壓力1MPa,熱壓時間15分鐘,獲得厚度為3mm刨花板。
實施例6:(1-十四烯共聚物體系)
按照質量份數,將39.2份1-十四烯,19.6份馬來酸酐,0.4份交聯劑雙甲基丙烯酸乙二醇酯,300份乙酸異戊酯和0.7份偶氮二異丁腈混合溶解,體系通氮氣20分鐘後在70℃反應6小時。將產物離心,洗滌,乾燥獲得白色粉末形式的交聯的1-十四烯-馬來酸酐共聚物,共聚物中馬來酸酐單體單元的質量百分數為33%。
將20份該1-十四烯-馬來酸酐共聚物,10份37%氨水,70份水在室溫下攪拌4小時,獲得質量濃度20%的1-十四烯-馬來醯胺酸共聚物懸浮液(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)。將該懸浮液與楊木刨花(含水量5%,5-10目)混合,每100份刨花中該共聚物用量12份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量20%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度170℃,壓力0.5MPa,熱壓時間15分鐘,獲得厚度為3mm刨花板。
實施例7:(1-十八烯共聚物體系)
按照質量份數,將50.4份1-十八烯,19.6份馬來酸酐,0.3份交聯劑二乙烯基苯,300份乙酸異戊酯和0.7份偶氮二異丁腈混合溶解,體系通氮氣20分鐘後在70℃反應6小時。將產物離心,洗滌,乾燥獲得白色粉末形式的交聯的1-十八烯-馬來酸酐共聚物,共聚物中馬來酸酐單體單元的質量百分數為28%。
將20份該1-十八烯-馬來酸酐共聚物,10份37%氨水,70份水在室溫下攪拌4小時,獲得質量濃度20%的1-十八烯-馬來醯胺酸共聚物懸浮液(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)。將該懸浮液與楊木刨花(含水量5%,5-10目)混合,每100份刨花中該共聚物用量12份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量15%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度160℃,壓力1MPa,熱壓時間15分鐘,獲得厚度為3mm刨花板。
實施例8:(混合α-烯烴共聚物體系)
按照質量份數,將4.7份1-戊烯,9.3份1-癸烯和14.9份1-十六烯,0.3份交聯劑二乙烯基苯,19.6份馬來酸酐,300份乙酸異戊酯和0.7份偶氮二異丁腈混合溶解,體系通氮氣20分鐘後在70℃反應6小時。將產物離心,洗滌,乾燥獲得白色粉末形式的混合烯烴-馬來酸酐共聚物,共聚物中馬來酸酐單體單元的質量百分數為43%。
將20份該混合烯烴-馬來酸酐共聚物,10份37%氨水,70份水在室溫下攪拌4小時,獲得質量濃度20%的混合烯烴-馬來醯胺酸共聚物懸浮液(共聚物中已氨解的馬來酸酐單體單元的莫耳百分數為99%)。將該懸浮液與楊木刨花(含水量5%,5-10目)混合,每100份刨花中該共聚物用量12份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量20%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度180℃,壓力1MPa,熱壓時間15分鐘,獲得厚度為3mm刨花板。
對比例1
按照質量份數,將10份異丁烯,17.5份馬來酸酐,100份乙酸異戊酯和0.3份BPO混合溶解,體系通氮氣20分鐘後在70℃反應8小時。將產物離心,用石油醚洗滌三次,乾燥獲得白色粉末形式的異丁烯-馬來酸酐共聚物,共聚物中馬來酸酐單體單元的質量百分數為63%。
將10份異丁烯-馬來酸酐共聚物與10份37%氨水,80份水在室溫下攪拌4小時,獲得質量濃度10%的黏稠液。將該黏稠液與楊木刨花(含水量5%,5-10目)混合,每100份刨花中該共聚物用量20份,混合均勻,獲得預混料。將預混料在70℃下烘除水份至含水量10%。
將上述預混料置於25cm×25cm×2.5cm的壓模中,熱壓溫度170℃,壓力0.4MPa,熱壓時間12分鐘,獲得厚度為3mm刨花板。
性能測試
根據GB/T 4897-2015對實施例1-8和對比例1得到的刨花板進行內結合強度、24h吸水厚度膨脹率以及防潮性能(沸水煮後內結合強度)進行測試,結果列於下表6中。
實施例1-8中的刨花板的各項性能都優於國標中對於在潮濕狀態下使用的家具型刨花板的性能要求,同時優於對比例1的刨花板的性能。
不希望受到任何理論的束縛,據信本發明黏合劑中的聚合物上的醯胺基團與羧基在壓製條件下可以脫水生成醯亞胺基團,而羧基還可以脫水生成酸酐基團,所得酸酐基團可以與木素纖維素材料上的羥基發生反應形成酯,這有助於提高所得人造板的機械性能和耐水性。
以上所述僅僅為本發明的較佳實施方式,需要指出的是,對於所屬技術領域具有通常知識者來說,在本發明原理的範圍內,所作出的若干改進和修飾,這些改進和修飾也應被同樣視為本發明的保護範圍。
Claims (20)
- 一種共聚物A,其具有(i)至少一種帶有醯胺基團與羧基和/或其銨鹽的重複單元,(ii)至少一種得自直鏈或支化的C2-C18 α-單烯烴的重複單元,和(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。
- 如請求項1所述的共聚物A,其中在該共聚物A中,重複單元(i)的量為10-80重量%,較佳20-80重量%或22-79重量%,基於共聚物A的重複單元的總量。
- 如請求項1或2所述的共聚物A,其中該直鏈或支化的C2-C18 α-單烯烴為直鏈或支化的C2-C12 α-單烯烴,較佳直鏈或支化的C2-C8 α-單烯烴。
- 如請求項1至3中任一項所述的共聚物A,其中在該共聚物A中,重複單元(ii)的量為10-75重量%,較佳15-74重量%或20-70重量%,基於共聚物A的重複單元的總量。
- 如請求項1至4中任一項所述的共聚物A,其中該具有至少兩個碳-碳不飽和雙鍵的單體中的碳-碳不飽和雙鍵選自(甲基)丙烯酸酯基團、(甲基)丙烯醯胺基團、乙烯基、烯丙基以及鏈烯或環烯中的碳-碳雙鍵。
- 如請求項1至5中任一項所述的共聚物A,其中在該共聚物A中,重複單元(iii)的量為0.1-70重量%,較佳0.1-30重量%,基於共聚物A的重複單元的總量。
- 如請求項1至6中任一項所述的共聚物A,其中該共聚物A衍生自共聚物B,該共聚物B具有:(i’)至少一種帶有酸酐基團的重複單元,(ii)至少一種得自直鏈或支化的C2-C18 α-單烯烴的重複單元,和(iii)至少一種得自具有至少兩個碳-碳不飽和雙鍵的單體的重複單元。
- 如請求項7所述的共聚物A,其中該共聚物B的帶有酸酐基團的重複單元(i’)得自至少一種具有碳-碳不飽和雙鍵和酸酐基團的單體。
- 如請求項8所述的共聚物A,其中該具有碳-碳不飽和雙鍵和酸酐基團的單體選自具有4-8個碳原子的單烯屬不飽和二羧酸酐,較佳馬來酸酐、衣康酸酐、檸康酸酐和亞甲基丙二酸酐,更佳馬來酸酐。
- 如請求項1至9中任一項所述的共聚物A,其中該共聚物A得自共聚物B與氨的反應。
- 一種包含如請求項1至10中任一項所述的共聚物A的黏合劑。
- 如請求項11所述的黏合劑,其中該黏合劑呈固體,較佳粉末形式;或者呈含水組成物,較佳呈水溶液形式,較佳該共聚物A的含量為2-40重量%,尤其是5-30重量%,基於含水組成物的總重量。
- 如請求項11或12所述的黏合劑,其中該黏合劑不含能夠與共聚物A的醯胺基團和/或羧基發生共價交聯反應的有機交聯劑。
- 一種包含由如請求項11至13中任一項所述的黏合劑形成的組分的製品。
- 如請求項14所述的製品,其中該製品為人造板、紙張、布或塗料。
- 如請求項15所述的製品,其中該製品為由木素纖維素材料和該黏合劑形成的人造板。
- 如請求項16所述的製品,其中該黏合劑用作基體樹脂,較佳該黏合劑填充木素纖維素材料之間的縫隙。
- 如請求項14至17中任一項所述的製品,其中以固含量計的黏合劑用量基於製品的總重量為1-45重量%,較佳2-35重量%,更佳3-30重量%。
- 如請求項14至18中任一項所述的製品,其中如請求項1至10中任一項所定義的共聚物A的用量基於製品的總重量為1-40重量%,較佳2-30重量%,更佳3-25重量%。
- 一種如請求項11至13中任一項所述的黏合劑在製備人造板、紙張、布或塗料中的用途。
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CN115652474A (zh) * | 2022-09-28 | 2023-01-31 | 清华大学 | 由酰胺酸共聚物制备酰亚胺共聚物的纤维的方法和由其制备的纤维 |
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GB756269A (en) * | 1953-10-09 | 1956-09-05 | Us Rubber Co | Adhesive compositions containing elastomers |
GB1363512A (en) * | 1971-03-25 | 1974-08-14 | Ethylene Plastique Sa | Adhesives based on copolymer of ethylene and maleic anhydride |
US3891576A (en) * | 1972-05-31 | 1975-06-24 | Ici Australia Ltd | Process |
JPS49131243A (zh) * | 1973-04-21 | 1974-12-16 | ||
JPS5649706A (en) * | 1980-09-05 | 1981-05-06 | Nippon Oil Co Ltd | Production of new composition |
DD228092A1 (de) * | 1984-10-08 | 1985-10-02 | Wolfen Filmfab Veb | Fotografisches silberhalogenidhaltiges material mit einer lichthofschutzschicht |
JPS62235380A (ja) * | 1986-04-04 | 1987-10-15 | Idemitsu Petrochem Co Ltd | 接着剤 |
DE10335673B4 (de) * | 2003-08-04 | 2007-01-18 | Celanese Emulsions Gmbh | Wässrige Dispersionsklebstoffe, Verfahren zu deren Herstellung und deren Verwendung |
CA2560044C (en) * | 2005-10-03 | 2010-11-23 | Rohm And Haas Company | Composite materials and methods of making the same |
DE102010015575A1 (de) * | 2010-04-19 | 2011-10-20 | Celanese Emulsions Gmbh | Mineralwollfasermatten, Verfahren zu deren Herstellung und Verwendung |
BR112014017220A8 (pt) * | 2012-01-13 | 2017-07-04 | Georgia Pacific Chemicals Llc | composições aglutinantes e métodos para fabricar e utilizar as mesmas |
CN203344147U (zh) | 2013-04-19 | 2013-12-18 | 苏州佰家丽新材料科技有限公司 | 纤维板 |
US20160001506A1 (en) * | 2014-07-02 | 2016-01-07 | Seiko Epson Corporation | Method of manufacturing three-dimensional structure, three-dimensional structure, and three-dimension formation composition |
CN107033309A (zh) | 2017-03-28 | 2017-08-11 | 曾华 | 一种纤维板胶黏剂的制备方法 |
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US20240109993A1 (en) | 2024-04-04 |
JP2023552988A (ja) | 2023-12-20 |
CN112625181A (zh) | 2021-04-09 |
MX2023006506A (es) | 2023-10-27 |
WO2022116364A1 (zh) | 2022-06-09 |
CN114591467B (zh) | 2023-06-20 |
CA3200291A1 (en) | 2022-06-09 |
KR20230140560A (ko) | 2023-10-06 |
EP4257655A1 (en) | 2023-10-11 |
CN112625181B (zh) | 2022-07-19 |
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