CN112391142A - 一种粘合剂及其制备和应用 - Google Patents
一种粘合剂及其制备和应用 Download PDFInfo
- Publication number
- CN112391142A CN112391142A CN202010566427.3A CN202010566427A CN112391142A CN 112391142 A CN112391142 A CN 112391142A CN 202010566427 A CN202010566427 A CN 202010566427A CN 112391142 A CN112391142 A CN 112391142A
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- Prior art keywords
- adhesive
- hydroxyl
- epoxy
- polyol
- polyether polyol
- Prior art date
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- 229920005862 polyol Polymers 0.000 claims abstract description 112
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 64
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 52
- 229920000570 polyether Polymers 0.000 claims abstract description 52
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 32
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 21
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- -1 persulfides Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
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- 238000000034 method Methods 0.000 claims description 11
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- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
本发明涉及一种粘合剂、粘合剂的制备方法和应用,特别是在粘接玻璃纤维复合材料中的应用,以及使用该粘合剂粘结得到的粘接制品。该粘合剂包含:一异氰酸酯官能度不小于2的多异氰酸酯;一环氧改性的聚醚多元醇;一含羟基的丙烯酸酯;一氧化还原催化剂;一硅烷偶联剂、可选的一含双酚A结构的多元醇;和可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇。本发明的粘合剂具有对湿气不敏感、粘接性能好和可操作时间长的优点。
Description
技术领域
本发明涉及一种粘合剂、粘合剂的制备方法和应用,特别是在粘接玻璃纤维复合材料中的应用,以及使用该粘合剂粘结得到的粘接制品。
背景技术
聚氨酯树脂是一种高交联密度的热固性高分子材料,可以用作粘合剂。在一些工业领域例如风机叶片领域、枕木领域,由于其需要的施胶量大,因此适合的粘合剂除满足基本的粘接性能外,还应当具有长有效加工时间(即可操作时间长)的特点。然而,通常情况下,含聚氨酯树脂的粘合剂的制备过程中,异氰酸酯和多元醇混合后反应速度很快,会迅速凝胶固化,可操作时间短。此缺点限制了含聚氨酯树脂的粘合剂的应用,尤其限制了含聚氨酯树脂的粘合剂在需要较长的可操作时间的领域的应用,例如风机叶片领域或枕木领域。
CN103314027B提及一种延迟交联的双组分聚氨酯体系,包含下列组分:多元醇、添加剂、65-100重量%的芳族聚异氰酸酯、0-35重量%的脂族聚异氰酸酯和 0.1-3.0重量%的延迟剂,其中混合物在25℃下的粘度(EN ISO2555)为100mPas至3000mPas,混合物的玻璃态转变温度为高于50℃,可操作时间为长于60分钟。然而,该聚氨酯体系的组分易与空气中的水反应,产生泡沫,影响聚氨酯的粘接性能。
CN101525439B提及一种含改性环氧树脂的粘合剂,包含以下组分:双酚A型环氧树脂、双酚F型环氧树脂、用于将环氧树脂改性的分子量为2000-3000的二官能度聚氨酯预聚体、含端胺基且分子量为500-1500的硅树脂、分子量为800-1400的含羟基的线型酚醛树脂、四官能环氧树脂和聚醚胺固化剂。该改性环氧树脂的制备方法是:1. 制备聚氨酯预聚体;2. 制备环氧树脂;3. 将环氧树脂改性。制备得到的改性环氧树脂可以应用于风力发电叶片阴、阳模的合模粘合。然而,含该改性环氧树脂的粘合剂通常需要较长的固化时间和大于100℃的固化温度,在工业上的使用效率低。
CN101903433B涉及一种基于芳族多异氰酸酯和聚酯二醇、聚碳酸酯多元醇、聚丁二烯多元醇、蓖麻油或二聚物二元醇或油脂化学品多元醇的双组份聚氨酯粘合剂。其包含NCO/OH比为0.9∶1至1.5∶1的多元醇组份和由多异氰酸酯制得的交联组分,所述多元醇组份含有:重量百分比为2至30的至少一种分子量大于1000g/mol的聚酯二醇;重量百分比为5至35的至少一种3-至14-官能多元醇;重量百分比为5至35的疏水性多元醇;重量百分比为2至65的附加添加剂或辅助剂,重量百分比总和为100%,其中交联的粘合剂的玻璃化温度Tg高于60℃但低于130℃。该双组份聚氨酯粘合剂用于粘合基于聚酯树脂或聚环氧树脂的玻璃纤维、碳纤维或纺织纤维模制件。该聚氨酯粘合剂可操作时间短且易与空气中的水反应。
WO201696277涉及一种基于高官能度芳族和脂肪族异氰酸酯的双组份聚氨酯粘合剂。该双组份聚氨酯粘合剂的NCO/OH比为0.9∶1至1.5∶1,粘合剂交联后玻璃化温度高于60℃、弹性模量为4000MPa、拉伸强度大于40MPa。该双组分聚氨酯粘合剂适合用于粘合不平整表面和基于聚酯树脂或聚环氧树脂的玻璃纤维、碳纤维或纺织纤维模制件。该双组分聚氨酯粘合剂可操作时间短且易与空气中的水反应。
CN102079810A公开了一种含聚氨酯-丙烯酸-环氧树脂光敏预聚物的高性能UV固化聚氨酯改性丙烯酸环氧树脂粘合剂。制备该光敏预聚物的方法包括:第一步,合成一种较低粘度的环氧丙烯酸酯的预聚物;第二步,制备聚氨酯丙烯酸酯树脂的预聚物;第三步,将上述两种预聚物按一定比率混合或反应而得所述聚氨酯-丙烯酸-环氧树脂光敏预聚物,通过添加光敏引发剂、光敏稀释剂、光固化交联剂和其它必要的助剂等,进一步制备所述聚氨酯-丙烯酸-环氧树脂UV固化粘合剂。由于该粘合剂需UV固化,其适用于粘接尼龙类薄膜等仅需要较薄粘合剂层的材料,不适用于风机叶片等需要较厚粘合剂层的材料。
CN106634789A涉及一种紫外光固化型粘合剂,包括以下重量份的组分:聚氨酯丙烯酸树脂20-30份、环氧丙烯酸树脂20-30份、活性单体30-40份、填料5-10份、光引发剂4-7份和偶联剂0.5-1份。由于该粘合剂需UV固化,其适用于粘接需要较薄粘合剂层的材料,不适用于风机叶片等需要较厚粘合剂层的材料。
CN103540288A提供一种紫外线固化型粘合剂,在含有使多元醇和聚异氰酸酯以及具有羟基的(甲基)丙烯酸类化合物反应而得到的聚氨酯(甲基)丙烯酸树脂、(甲基)丙烯酸类单体、以及光聚合引发剂的紫外线固化型粘合剂中,还含有重量比在95/5-5/95的范围中含有光稳定剂和抗氧化剂。由于该粘合剂需UV固化,其适用于粘接需要较薄粘合剂层的材料,不适用于风机叶片等需要较厚粘合剂层的材料。
因此,希望开发一种适用于风机叶片等需要较厚粘合剂层的应用,且兼具对湿气不敏感、良好的粘接性能和长可操作时间等优点的粘合剂。
发明内容
本发明的目的是提供一种粘合剂,粘合剂的制备方法和应用,特别是在粘接玻璃纤维复合材料中的应用,以及使用该粘合剂粘结得到的粘接制品。
根据本发明的粘合剂包含以下组分:
a. 一异氰酸酯官能度不小于2的多异氰酸酯;
b. 一环氧改性的聚醚多元醇;
c. 一含羟基的丙烯酸酯;
d. 一氧化还原催化剂;
e. 一硅烷偶联剂;
f. 可选的一含双酚A结构的多元醇;和
g. 可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇;
所述含羟基的丙烯酸酯符合以下通式:
其中R1为氢或甲基或–CH2-OH,和R2为饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团,其中所述饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团可以任选地包含氧原子和/或羟基基团;
和其中所述氧化还原催化剂为下列的一种或多种:过氧化物、过硫化物、过氧化碳酸酯、过氧化硼酸和叠氮化合物;所述环氧改性的聚醚多元醇的量是50重量%-70重量%,和所述含羟基的丙烯酸酯的量为25重量%-50重量%,以所述组分b、c、f和g的重量之和为100重量%计。
根据本发明的一个方面,提供了本发明所提供的粘合剂的制备方法,包含以下步骤:以任意方式混合所述异氰酸酯官能度不小于2的多异氰酸酯(a)、环氧改性的聚醚多元醇(b)、含羟基的丙烯酸酯(c)、氧化还原催化剂(d)、硅烷偶联剂(e)、可选的一含双酚A结构的多元醇(f)和可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇(g);
所述含羟基的丙烯酸酯符合以下通式:
其中R1为氢或甲基或–CH2-OH,和R2为饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团,其中所述饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团可以任选地包含氧原子和/或羟基基团;
和其中所述氧化还原催化剂为下列的一种或多种:过氧化物、过硫化物、过氧化碳酸酯、过氧化硼酸和叠氮化合物;
所述环氧改性的聚醚多元醇的量是50重量%-70重量%,和所述含羟基的丙烯酸酯的量为25重量%-50重量%,以所述组分b、c、f和g的重量之和为100重量%计。
根据本发明的又一个方面,提供了根据本发明所提供的粘合剂用于粘接玻璃纤维复合材料的应用。
根据本发明的再一个方面,提供了根据本发明所提供的粘合剂用于制备粘接制品的用途。
根据本发明的还一个方面,提供了一种包含根据本发明所提供的粘合剂的粘接制品。
根据本发明的还一个方面,提供了制造粘接产品的方法,包含以下步骤:
i. 将根据本发明所提供的粘合剂注入所需粘结部件的腔体中或涂覆到所需粘结的基材上;和
ii. 加热和固化所述粘合剂得到所述粘接制品。
本发明的粘合剂对湿气不敏感且具有长可操作时间,并能兼具良好的粘接性能。因此,特别适用于粘接需要较厚粘合剂层的玻璃纤维复合材料。
具体实施方式
本发明提供一种粘合剂,包含以下组分:
a. 一异氰酸酯官能度不小于2的多异氰酸酯;
b. 一环氧改性的聚醚多元醇;
c. 一含羟基的丙烯酸酯;
d. 一氧化还原催化剂;
e. 一硅烷偶联剂;
f. 可选的一含双酚A结构的多元醇;和
g. 可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇;
所述含羟基的丙烯酸酯符合以下通式:
其中R1为氢或甲基或–CH2-OH,和R2为饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团,其中所述饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团可以任选地包含氧原子和/或羟基基团;
和其中所述氧化还原催化剂为下列的一种或多种:过氧化物、过硫化物、过氧化碳酸酯、过氧化硼酸和叠氮化合物;所述环氧改性的聚醚多元醇的量是50重量%-70重量%,和所述含羟基的丙烯酸酯的量为25重量%-50重量%,以所述组分b、c、f和g的重量之和为100重量%计。本发明还提供了该粘合剂的制备方法和应用,特别是在粘接玻璃纤维复合材料中的应用,以及使用该粘合剂粘结得到的粘接制品。
本文所用的术语“固化”是指粘合剂从液态到固化态的过程。
本文所用的术语“粘合剂”是指包含可固化并具有粘性的化学组分的混合物,也用作胶黏剂和/或密封剂和/或粘着剂的同义词。
本文所用的术语“聚氨酯”是指聚氨酯脲和/或聚氨酯聚脲和/或聚脲和/或聚硫氨酯。
本文所用的术语“各自独立地”是指可以相同或不相同。
异氰酸酯官能度不小于2的多异氰酸酯
所述异氰酸酯官能度不小于2的多异氰酸酯优选符合通式R(NCO)n,其中R是下列的一种或多种:含2-18个碳原子的脂肪族烃基、含6-15个碳原子的芳烃基和含8-15个碳原子芳脂族烃基,n是2-4。
所述多异氰酸酯的异氰酸酯官能度优选2-3。
所述多异氰酸酯的粘度优选小于50mPa·s-1000mPa·s,最优选50-700mPa·s,根据DIN EN ISO 3219:1994-10在 23oC,剪切速率为10s-1下测定。
所述多异氰酸酯的异氰酸酯基团含量优选20重量%-35重量%,以所述多异氰酸酯的重量为100重量%计。
所述多异氰酸酯优选下列的一种或多种:二苯甲烷-4,4’-二异氰酸酯(MDI)、二苯甲烷-2,4’-二异氰酸酯(MDI)、二苯甲烷-2,2’-二异氰酸酯(MDI)、乙烯基二异氰酸酯、四亚甲基1,4-二异氰酸酯、己二异氰酸酯(HDI)、十二烷基1,2-二异氰酸酯、环丁烷-1,3-二异氰酸酯、环己烷-1,3-二异氰酸酯、环己烷-1,4-二异氰酸酯、1-异氰酸酯基-3,3,5-三甲基-5-异氰酸酯基甲基环己烷、六氢甲苯-2,4-二异氰酸酯、六氢苯基-1,3-二异氰酸酯、六氢苯基-1,4-二异氰酸酯、全氢化-二苯甲烷2,4-二异氰酸酯、全氢化-二苯甲烷4,4-二异氰酸酯、亚苯基1,3-二异氰酸酯、亚苯基1,4-二异氰酸酯、杜烯1,4-二异氰酸酯、均二苯乙烯均二苯乙烯1,4-二异氰酸酯、3,3-二甲基4,4-二苯基二异氰酸酯、甲苯-2,4-二异氰酸酯(TDI)、甲苯-2,6-二异氰酸酯(TDI)、聚二苯基甲烷二异氰酸酯(PMDI)和碳化二亚胺改性的异氰酸酯、脲基甲酸酯改性的异氰酸酯和上述异氰酸酯的异构体。
所述多异氰酸酯进一步优选下列的一种或多种:聚二苯基甲烷二异氰酸酯、甲苯二异氰酸酯和碳化二亚胺改性的二苯基甲烷二异氰酸酯,最优选聚二苯基甲烷二异氰酸酯。
所述多异氰酸酯的量优选38重量%-60重量%,最优选45重量%-53重量%,以所述粘合剂的量为100重量%计。
环氧改性的聚醚多元醇
所述环氧改性的聚醚多元醇的羟基官能度优选2-8,进一步优选2-6,最优选2-3。
所述环氧改性的聚醚多元醇的羟值优选18 mgKOH/g -1200mgKOH/g,进一步优选150 mgKOH/g -800mgKOH/g,最优选200 mgKOH/g -500mgKOH/g。
在本发明一个实施方案中,优选所述聚醚多元醇的官能度为2-8,羟值为18mgKOH/g -1200mgKOH/g;进一步优选所述聚醚多元醇的官能度为2-6,羟值为150 mgKOH/g-800 mgKOH/g;最优选所述聚醚多元醇的官能度为2-3,羟值为200 mgKOH/g -500 mgKOH/g。
所述环氧改性的聚醚多元醇的粘度优选20 mPa·s -500 mPa·s,数均分子量优选300-500。
所述环氧改性的聚醚多元醇优选由包含多元醇和环氧烷化合物的体系反应得到,其中进行环氧化物开环反应。
所述多元醇优选含有至少两个羟基。
所述多元醇的羟基官能度优选3-8,羟值优选18-1200 mgKOH/g。
所述羟基包括伯羟基、仲羟基、叔羟基或其组合。
所述多元醇优选下列的一种或多种:乙二醇、二乙二醇、三甘醇、四甘醇、1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、3-甲基-1,5-戊二醇、1,5-戊二醇、1,6-己二醇、1,10-癸二醇、甘油、1,2,4-丁三醇、1,2,5-正戊三醇、1,3,5-正戊三醇、1,2,6-正己三醇、1,2,5-正己三醇、1,3,6-正己三醇、三羟甲基丁烷、三羟甲基丙烷、二(三羟甲基丙烷)、三羟甲基乙烷、季戊四醇和二季戊四醇,最优选下列的一种或多种:丙二醇和甘油。
所述环氧烷化合物优选符合以下通式:
其中,R3和R3'各自独立地是氢、C1-C6直链烷基、C1-C6支链烷基、苯基或取代苯基。
R3和R3'各自独立地优选氢、甲基、乙基、丙基或苯基。
所述环氧烷化合物优选下列的一种或多种:1,2-环氧丙烷、1,2-环氧丁烷、2,3-环氧丁烷、氧化苯乙烯和氧化杂烷烃。
所述氧化杂烷烃优选下列的一种或多种:四氢呋喃和氧杂环丁烷。
所述环氧烷化合物的制备方法可以是本领域技术人员熟知的,例如可以通过烯烃化合物的氧化反应获得。
所述可用于本发明的环氧改性的聚醚多元醇优选下列的一种或多种:可购自中国石化股份有限公司上海高桥分公司的GE 303(以甘油为起始剂,羟值为480 mgKOH/g)、GR635s(以山梨醇和甘油为起始剂,羟值为500 mgKOH/g)、GSU -450L(以蔗糖和甘油为起始剂,羟值为435 mgKOH/g)、GMN -450 (以甘油为起始剂,羟值为450 mgKOH/g)、可购自BayerMaterial Science的Desmophen 3601(以蔗糖和甘油为起始剂,羟值为260 mgKOH/g)和Desmophen 21AP27(以蔗糖和乙二醇为起始剂,羟值为440 mgKOH/g)。
本文中羟值的测量方法采用Houben Weyl, Methoden der Organischen Chemie,vol. XIV/2 Makromolekulare Stoffe, p.17, Georg Thieme Verlag; Stuttgart 1963中所公开的方法。将该文献的全部内容以引用的方式合并入本文中。
所述环氧改性的聚醚多元醇的量为50重量%-70重量%,以所述组分b、c、f和g的重量之和为100重量%计。
不同于所述环氧改性的聚醚多元醇的聚合物多元醇
所述不同于环氧改性的聚醚多元醇的聚合物多元醇优选下列的一种或多种:聚酯多元醇、聚醚多元醇、聚碳酸酯多元醇、聚四氢呋喃多元醇、聚己内酯多元醇、SAN聚合物多元醇、PHD聚合物多元醇、PIPA聚合物多元醇、植物油和植物油多元醇。
所述聚酯多元醇可以由包含二元羧酸或二元羧酸酐与多元醇的体系反应制得。所述二元羧酸优选含2-12个碳原子的脂肪族羧酸,例如:丁二酸、丙二酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十二烷基羧酸、顺丁烯二酸、反丁烯二酸、邻苯二甲酸、异酞酸、对苯二酸或它们的混合物。所述二元酸酐优选下列的一种或多种:邻苯二甲酸酐、四氯苯酐和马来酸酐。所述多元醇优选下列的一种或多种:乙二醇、二甘醇、1,2-丙二醇、1,3-丙二醇、二丙二醇、1,3-甲基丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、新戊二醇、1,10-癸二醇、丙三醇和三羟甲基丙烷。
所述聚酯多元醇也可以由包含内酯的体系反应制备得到,优选ε-己内酯。
所述聚醚多元醇可以通过众所周知的工艺过程制备,例如,在催化剂存在下,由烯烃氧化物与起始剂反应制得。所述催化剂优选下列的一种或多种:碱性氢氧化物、碱性醇盐、五氯化锑和氟化硼合乙醚。所述烯烃氧化物优选下列的一种或多种:四氢呋喃、环氧乙烷、1,2-环氧丙烷、1,2-环氧丁烷、2,3-环氧丁烷和氧化苯乙烯。所述起始剂优选多羟基化合物,例如:水、乙二醇、1,2-丙二醇、1,3-丙二醇、二甘醇、甘油、三羟甲基丙烷、季戊四醇、山梨醇、蔗糖或它们的混合物。
所述聚醚多元醇优选下列的一种或多种:聚环氧丙烷多元醇、聚环氧乙烷多元醇和聚四氢呋喃多元醇。
所述聚碳酸酯多元醇优选聚碳酸酯二醇。所述聚碳酸酯二醇可以由二醇与二烃基或二芳基碳酸酯或光气反应制得。所述二烃基或二芳基碳酸酯优选二苯基碳酸酯。所述聚碳酸酯二醇优选下列的一种或多种:1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、二甘醇和三聚甲醛二醇。
所述SAN聚合物多元醇、PHD聚合物多元醇、PIPA聚合物多元醇是固体增强颗粒在多元醇液体中形成的稳定分散体。
所述SAN聚合物多元醇优选由含丙烯腈和苯乙烯的混合物在基本多元醇中原位聚合得到。
所述PHD聚合物多元醇优选由含异氰酸酯和二胺的混合物在基本多元醇中原位聚合得到。
所述PIPA聚合物多元醇优选由含异氰酸酯和二醇和/或二醇-胺的混合物在基本多元醇中原位聚合得到。
所述植物油优选由不饱和脂肪酸和甘油合成得到或者从植物的果实、种子、胚芽中得到。所述植物油优选下列的一种或多种:花生油、豆油、亚麻油、蓖麻油、菜子油和棕榈油,最优选蓖麻油。
所述植物油多元醇优选由一种或多种植物油为起始剂通过裂解、氧化或酯交换等工艺制备得到。所述植物油优选下列的一种或多种:大豆油,棕榈油、花生油、低芥酸菜子油和含有羟基基团和不饱和双键的蓖麻油酸。
所述不同于环氧改性的聚醚多元醇的聚合物多元醇的量优选10重量%-20重量%,以所述粘合剂的量为100重量%计。
所述环氧改性的聚醚多元醇和可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇的重量之和与多异氰酸酯的重量比为0.4-1.2,最优选0.45-1.15。
含羟基的丙烯酸酯
所述含羟基的丙烯酸酯的量为25重量%-50重量%和优选30重量%-50重量%,以所述组分b、c、f和g的重量之和为100重量%计。
所述含羟基的丙烯酸酯优选符合以下通式:
其中R1为氢或甲基或–CH2-OH,和R2为饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团,其中所述饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团可以任选地包含氧原子和/或羟基基团。
所述含羟基的丙烯酸酯进一步优选下列的一种或多种:含羟基的丙烯酸和甲基丙烯酸的衍生物、3-羟丙酯、2-羟丙酯、羟丁酯、聚乙烯醇单羟酯、甲基羟基丙烯酸酯羟烷酯和聚丙烯醇单羟酯,再优选下列的一种或多种:含羟基的丙烯酸和甲基丙烯酸的衍生物、3-羟丙酯、2-羟丙酯、羟丁酯和聚乙烯醇单羟酯,还优选含羟基的丙烯酸和甲基丙烯酸的衍生物,最优选甲基丙烯酸羟丙酯。
所述组分b、组分c、组份f和组分g的重量之和优选30重量%-60重量%,最优选40重量%-55重量%,以所述粘合剂的量为100重量%计。
氧化还原催化剂
所述氧化还原催化剂是可以引发含双键化合物固化的自由基引发剂。
所述氧化还原催化剂优选下列的一种或多种:过氧化苯甲酰(BPO)、过氧化苯甲酸叔丁酯(TBPB)、过氧化甲乙酮和过氧化二异丙苯(DCP),最优选下列的一种或多种:过氧化苯甲酰和过氧化甲乙酮。
所述氧化还原催化剂可以直接与所述环氧改性的聚醚多元醇混合,也可以直接与所述异氰酸酯官能度不小于2的多异氰酸酯混合,还可以直接与所述环氧改性的聚醚多元醇和所述异氰酸酯官能度不小于2的多异氰酸酯混合。
所述氧化还原催化剂的量优选0.5重量%-1.5重量%,最优选0.9重量%-1.1重量%,以所述粘合剂的量为100重量%计。
硅烷偶联剂
所述硅烷偶联剂优选符合通式XSi(OR4)3,其中X是下列的一种或多种:乙烯基、γ-甲基丙烯酰氧基丙基和γ-异氰酸基丙基;R4是下列的一种或多种:甲基和乙基。
所述硅烷偶联剂进一步优选下列的一种或多种:乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基-三-(2-甲氧基乙氧基)硅烷、乙烯基甲基二甲氧基硅烷、乙烯基三异丙氧基硅烷、γ-异氰酸基丙基三甲氧基硅烷、γ-异氰酸基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三异丙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-甲基丙烯酰氧基丙基三乙氧基硅烷、 甲苯磺酰异氰酸酯和三-(3-三甲氧基硅基丙基)异氰脲酸酯,最优选乙烯基三乙氧基硅烷。
所述硅烷偶联剂的量优选0.5重量%-1.5重量%,最优选0.9重量%-1.1重量%,以所述粘合剂的量为100重量%计。
含双酚A结构的多元醇
所述含双酚A结构的多元醇的量优选0-30重量%,进一步优选5重量%-25重量%,最优选5重量%-8重量%,以所述粘合剂的量为100重量%计。
所述含双酚A结构的多元醇优选符合以下通式:
其中, m和n各自独立地为1-200的整数,R5和R6各自独立地为烷基。
m和n各自独立地优选1-10的整数,各自独立地最优选1-5的整数。
R5和R6各自独立地优选下列的一种或多种:甲基和乙基,各自独立地最优选甲基。
所述含双酚A结构的多元醇最优选Innonyx P263。
其他组分
所述粘合剂还可以进一步包含下列的一种或多种:脱水剂、消泡剂、抑制剂、表面活性剂、色膏和填料。
所述脱水剂优选下列的一种或多种:原甲酸(三)乙酯、噁唑烷和分子筛,最优选硅铝酸盐类无机脱水剂。
所述抑制剂优选下列的一种或多种:苯甲酰基醌、对苯醌、叔丁基儿茶酚、氢醌例如甲基氢醌和甲基乙基氢醌(MEHQ)、丁基化羟基甲苯(BHT)、丁基化羟基苯胺(BHA)和2-羟基-4甲氧基二苯甲酮。
所述填料优选下列的一种或多种:膨润土、粉煤灰、硅灰石、珍珠岩粉、漂珠、碳酸钙、滑石粉、云母粉、瓷土、气相白炭黑、可膨胀微球、硅藻土、火山灰、硫酸钡、硫酸钙、玻璃微球、石粉、木粉、木屑、竹粉、竹屑、稻粒、秸秆碎屑、高粱杆碎屑、石墨粉、金属粉末、热固性复合材料回收粉料、塑料颗粒和塑料粉末。
上述其他组分选择和使用计量原则上是本领域普通技术人员已知的并且容易测定的。
应用
所述玻璃纤维复合材料优选下列的一种或多种:玻璃纤维增强环氧树脂、玻璃纤维增强聚氨酯树脂和玻璃纤维增强发泡聚氨酯。
制造粘接产品的方法
所述所需粘结部件的腔体优选是玻璃纤维复合材料构成的。
所述所需粘结的基材优选是玻璃纤维复合材料构成的。
所述玻璃纤维复合材料优选下列的一种或多种:玻璃纤维增强环氧树脂、玻璃纤维增强聚氨酯树脂和玻璃纤维增强发泡聚氨酯。
所述粘接制品优选风机叶片或枕木。
所述粘合剂加热和固化后的厚度优选5mm-20mm。
所述加热并干燥可以除去易挥发组分。所述易挥发组分可以是水。
所述加热的温度越高越好,但不应当高于材料以不可控方式变形或遭遇其它破坏的温度界限。
所述加热优选120℃-210℃,进一步优选150℃-200℃,最优选160℃-180℃。
实施例
除非另外限定,本文所使用的所有技术和科学术语具有本发明所属领域技术人员通常理解的相同意义。当本说明书中术语的定义与本发明所属领域技术人员通常理解的意义有矛盾时,以本文中所述的定义为准。
除非另有说明,否则在说明书和权利要求书中使用的表达成分的量、反应条件等的所有数值被理解为在被术语“约”修饰。因此,除非有相反指示,否则在这里阐述的数值参数是能够根据需要获得的所需性能来变化的近似值。
本文中所用的“和/或”是指所提及的要素之一或全部。
本文中所用“包括”和“包含”涵盖只有所提及要素的情形以及除了所提及要素还存在其它未提及要素的情形。
本发明中所有百分比均为重量百分比,另有说明的除外。
本发明的分析测量都在23℃下进行,另有说明的除外。
除非另有说明,否则在本说明书中所用的“一”、“一种”、“一个”和“该”意在包括“至少一种”或“一种或多种”。例如,“一组分”是指一种或多种组分,因此在所述实施方案的实施中可能考虑并可能采用或使用多于一种组分。
异氰酸酯基团(NCO)含量根据DIN-EN ISO 11909按体积测定,测定的数据包括游离的和潜在游离的NCO含量。
异氰酸酯官能度根据GPC测定。
数均分子量采用凝胶渗透色谱法以四氢呋喃为流动相,对照聚苯乙烯标样在23℃下测定。
多异氰酸酯的异氰酸酯的指数=异氰酸酯官能度不小于2的多异氰酸酯的异氰酸酯基团的摩尔数)/粘合剂中的异氰酸酯基团反应性基团的摩尔数。
粘度根据DIN EN ISO 3219:1994-10在23℃,剪切速率为10s-1下测定,选择MV-DIN转子。
对湿气敏感性的测试:将熟化的混凝土板在水中泡4小时后,用纸擦干;将混合好的粘合剂涂覆在混凝土板表面,涂覆厚度约1mm,在室温下固化24小时后,观察固化的粘合剂表面是否发泡。对湿气敏感性测试的等级分为发泡、略发泡、无发泡,无发泡视为合格,既对湿气不敏感。
可操作时间的测试;在25℃下,将多异氰酸酯和环氧改性的聚醚多元醇分别真空脱气1-2 小时后待用,随后将粘合剂的各组分混合搅拌均匀,按DIN EN ISO 3219标准测试粘合剂的粘度值,粘合剂从混合均匀到粘度值大于600 mPa·s的时间即为粘合剂的可操作时间。可操作时间越长越好。
最高放热峰的测试:在500毫升纸质反应杯的中间设置测量温度的热电偶,并与计算机相连。在25℃下,将300g的多异氰酸酯和300g的环氧改性的聚醚多元醇分别真空脱气1-2 小时后待用,随后将粘合剂的各组分混合搅拌均匀,倒入反应杯中,开始测试温度-时间曲线并记录,温度最高点即为最高放热峰。最高放热峰低,粘合剂后熟化时间短,生产效率高。
耐冲击性的测定:将模具放入160℃的烘箱中控温10分钟。按照粘合剂的化学配比所需组成,将各组分混合并搅拌均匀,再放入转速为1500 rpm的离心搅拌器中混合10分钟得到混合物,将混合物倒入直径*厚度为5cm*0.5cm模具中,在160℃下固化10分钟后室温放置24小时后得到样品。使用重量为2公斤、直径为0.5cm的冲击头,从50 厘米高度以自由落体下落冲击样品。 测试结果可以依次用击穿、有裂痕和未击穿表示,并依次表示粘接性能由差到好。
巴氏硬度的测试:根据美国标准ASTM B648测试。
拉伸模量的测试:DIN EN ISO 14125。
拉伸强度的测试:DIN EN ISO 14125。
拉伸断裂伸长率的测试:DIN EN ISO 14125。
体积收缩率的测试:ASTM D696。
弯曲强度的测试:GB /T 9341-2000。
热变形温度:ASTM D648, ISO 75-2, GB/T 1634.2。
拉伸剪切强度:刚性材料对刚性材料,GB 7124-2008 T。
下述性能指标巴氏硬度、拉伸模量、拉伸强度、弯曲强度、拉伸断裂伸长率、热变形温度、体积收缩率和拉伸剪切强度越大,说明粘合剂的粘接性能越好。
原料和试剂
Desmodur 1511L:聚二苯基甲烷二异氰酸酯(PMDI),异氰酸酯官能度为2.7,NCO基团含量30.5-32.5重量%,粘度160-240 mPa.s,可由科思创聚合物有限公司有限公司购得。
Desmodur 88TM12:多异氰酸酯,异氰酸酯官能度为2.0,NCO基团含量 23.5重量%,粘度350-550mPa.s,可由科思创聚合物有限公司有限公司购得。
环氧改性的聚醚多元醇1:环氧改性聚醚多元醇NJ-303E,可由宁武新材料有限公司购得,以甘油作为起始剂,环氧丙烷作为聚合反应的主体反应得到,羟值470 mgKOH/g,羟基官能度3,粘度450mPa·s,数均分子量350。
环氧改性的聚醚多元醇2:环氧改性聚醚多元醇GY-420,可由国都化工(昆山)有限公司购得,以甘油作为起始剂,环氧丙烷作为聚合反应的主体反应得到,羟值350 mgKOH/g,羟基官能度3,粘度450mPa·s,数均分子量480。
环氧改性的聚醚多元醇3:环氧改性聚醚多元醇NJ-204;可由宁武新材料有限公司购得,以丙二醇作为起始剂,环氧丙烷作为聚合反应的主体反应得到,羟值280 mgKOH/g,羟基官能度2,粘度70 mPa.s,数均分子量400。
甲基丙烯酸羟丙酯(HPMA):可由上海医药集团购得。
Trigonox 400:过氧化甲乙酮,可由阿克苏公司购得。
过氧化苯甲酰:市售化学纯产品。
NOROX KP-925H:过氧化丁酮,可由硕津公司购得。
Innonyx P263:含双酚A结构的多元醇, OHNO= 326,羟基官能度2,可购自台湾伊诺士国际有限公司。
EPIKOTE™ Resin RIM 135:环氧树脂,常用于标准风机叶片生产,可购自Hexion公司。
EPIKURE™RIM 135H:环氧树脂,常用于标准风机叶片生产,可购自Hexion公司。
A 151:乙烯基三乙氧基硅烷。
实施例1-3和对比实施例1-3
将模具放入160℃的烘箱中控温10分钟。按照表1所示的粘合剂的组成,将各组分混合并搅拌均匀,再放入转速为1500rpm的离心搅拌器中混合10分钟得到混合物,将混合物倒入模具中,在160℃下固化120分钟,得到对比实施例1-3和实施例1-3的固化的粘合剂。测试粘合剂的对湿气敏感性、可操作时间、巴氏硬度、拉伸模量、拉伸强度、拉伸断裂伸长率、体积收缩率、热变形温度和耐冲击性。
表1 列出了实施例1-3和对比实施例1-3的粘合剂的组成和粘合剂的性能指标。
表1:粘合剂组成和性能指标
粘合剂组成 | 对比实施例 1 | 对比实施例2 | 对比实施例3 | 实施例1 | 实施例2 | 实施例3 |
环氧改性的聚醚多元醇1 | 100 | 90 | 80 | 70 | 60 | 50 |
甲基丙烯酸羟丙酯 | / | 10 | 20 | 30 | 40 | 50 |
A151 | 2 | 2 | 2 | 2 | 2 | 2 |
过氧化苯甲酰 | / | 2 | 2 | 2 | 2 | 2 |
Desmodur 1511L | 117 | 115 | 112 | 110 | 108 | 106 |
异氰酸酯指数 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 |
对湿气敏感性 | 发泡 | 发泡 | 略发泡 | 无发泡 | 无发泡 | 无发泡 |
可操作时间(min) | 82 | 125 | 140 | 172 | 214 | 275 |
巴氏硬度(Hba) | 36 | 37 | 40 | 43 | 48 | 52 |
拉伸模量(MPa) | 3100 | 3300 | 3500 | 3700 | 3900 | 3900 |
拉伸强度(MPa) | 80 | 85 | 87 | 90 | 93 | 95 |
拉伸断裂伸长率(%) | 5.6 | 4.6 | 3.8 | 3.6 | 3.4 | 3.1 |
体积收缩率(%) | 8.4 | 9.1 | 9.2 | 9.3 | 9.5 | 9.8 |
热变形温度(℃) | 62 | 73 | 82 | 91 | 98 | 105 |
耐冲击性 | 击穿 | 击穿 | 有裂痕 | 未击穿 | 未击穿 | 未击穿 |
比较对比实施例1-3与实施例1-3,可以看出本发明的粘合剂无发泡即粘合剂对湿气不敏感,粘合剂可操作时间大幅提高,粘合剂粘接性能优良。当含羟基的丙烯酸酯的含量为30重量%-50重量%,环氧改性的聚醚多元醇的含量为50重量%-70重量%时,相应的粘合剂的整体性能指标,包括对湿气不敏感、可操作时间和粘接性能最优。
实施例5-7和对比实施例4
在25℃下将多异氰酸酯和环氧改性的聚醚多元醇2分别抽真空0.1-2h脱去原料中的气泡。将模具放入160℃的烘箱中控温10分钟。按照表2所示的粘合剂的组成,将各组分混合并搅拌均匀,再放入转速为1500rpm的离心搅拌器中混合10分钟得到混合物,将混合物倒入模具中,在160℃下固化120分钟,得到对比实施例4和实施例5-7的固化的粘合剂。测试粘合剂的对湿气敏感性、可操作时间、巴氏硬度拉伸模量、拉伸强度、弯曲强度、拉伸断裂伸长率、热变形温度和耐冲击性。
表2 列出了实施例5-7和对比实施例4的粘合剂的组成和这些粘合剂的性能指标。
表2:粘合剂组成和性能指标
比较对比实施例4与实施例5-7,可以看出本发明的粘合剂无发泡即对湿气不敏感,粘合剂的可操作时间大幅提高且粘接性能优良。
比较实施例5-7可以看出,当粘合剂进一步包含含有双酚A结构的多元醇时,粘合剂在保持对湿气不敏感和长可操作时间的基础上,粘接性能进一步提高。
实施例8-9和对比实施例5
在25℃下用清洗液(甲乙酮 95重量份、乙烯基三甲氧基硅烷2重量份和γ-氨丙基三甲氧基硅烷A-1100 3重量份)分别清洗待粘结样片的表面(样品尺寸(100±0.25 mm)*(25±0.25 mm)*(1.5±0.1 mm),粘结面长度(12.5±0.25 mm,样片材料为玻璃钢),25℃下自然干燥20分钟。在25℃下将多异氰酸酯和环氧改性的聚醚多元醇分别抽真空0.1-2h脱去原料中的气泡。将模具放入160℃的烘箱中控温10分钟。按照表3所示的粘合剂的组成,将各组分混合并搅拌均匀,再放入转速为1500rpm的离心搅拌器中混合10分钟得到混合物,用刷子将混合物均匀涂覆在样片表面,将两片样片的各自涂覆有混合物的一面贴合并用夹子夹紧,在80℃下固化180分钟,室温冷却30分钟后,测试粘结好的样片的对湿气敏感性、可操作时间、巴氏硬度和拉伸剪切强度。
表3列出了实施例8-9和对比实施例5的粘合剂的组成和性能指标。
表3:粘合剂组成和性能指标
比较对比实施例5与实施例8-9,可以看出本发明的粘合剂无发泡即对湿气不敏感,粘合剂可操作时间大幅提高且粘接性能优良。
从实施例8、9可以看出,包含不同的多异氰酸酯的粘合剂都对湿气不敏感,且都具有长可操作时间和良好的粘接性能,其中包含PMDI的粘合剂的整体性能比包含异氰酸酯预聚体的粘合剂的整体性能更优。
实施例10和对比实施例6
在25℃下将多异氰酸酯和环氧改性的聚醚多元醇分别抽真空0.1-2h脱去原料中的气泡。将模具放入160℃的烘箱中控温10分钟。按照表4所示的粘合剂的组成,将各组分混合并搅拌均匀,再放入转速为1500rpm的离心搅拌器中混合5分钟得到混合物,将一部分混合物倒入粘度测试杯测量粘度,剩余的混合物倒入模具中,在160℃下固化120分钟,室温放置3天,得到对比实施例6和实施批例10的固化的粘合剂。测试粘合剂的粘度、对湿气敏感性、可操作时间、拉伸模量、拉伸强度、拉伸断裂伸长率、热变形温度、耐冲击性和最高放热峰。
表4列出了实施例10和对比实施例6的粘合剂的组成和性能指标。
表4:粘合剂组成和性能指标
比较对比实施例6与实施例10,可以看出本发明的粘合剂与市售的常用于风机叶片的环氧树脂相比,两者的可操作时间和对湿气敏感性指标相当,但本发明的粘合剂相比常用的环氧树脂具有更好的粘接性能。并且,本发明的粘合剂的最高放热峰低于环氧树脂的,本发明的粘合剂后熟化时间短,即本发明的粘合剂的生产效率高于环氧树脂的。
所属领域的技术人员易知,本发明不仅限于前述的具体细节,且在不脱离本发明的精神或主要特性的前提下,本发明可实施为其他特定形式。因此从任何角度来说都应将所述实施例视作例示性而非限制性的,从而由权利要求书而非前述说明来指出本发明的范围;且因此任何改变,只要其属于权利要求等效物的含义和范围中,都应视作属于本发明。
Claims (15)
1.一种粘合剂,包含以下组分:
a. 一异氰酸酯官能度不小于2的多异氰酸酯;
b. 一环氧改性的聚醚多元醇;
c. 一含羟基的丙烯酸酯;
d. 一氧化还原催化剂;
e. 一硅烷偶联剂;
f. 可选的一含双酚A结构的多元醇;和
g. 可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇;
所述含羟基的丙烯酸酯符合以下通式:
其中R1为氢或甲基或–CH2-OH,和R2为饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团,其中所述饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团可以任选地包含氧原子和/或羟基基团;
和其中所述氧化还原催化剂为下列的一种或多种:过氧化物、过硫化物、过氧化碳酸酯、过氧化硼酸和叠氮化合物;
所述环氧改性的聚醚多元醇的量是50重量%-70重量%,和所述含羟基的丙烯酸酯的量为25重量%-50重量%,以所述组分b、c、f和g的重量之和为100重量%计。
2.如权利要求1所述的粘合剂,其特征在于,所述含羟基的丙烯酸酯是下列的一种或多种:含羟基的丙烯酸或甲基丙烯酸的衍生物、3-羟丙酯、2-羟丙酯、羟丁酯、聚乙烯醇单羟酯、甲基羟基丙烯酸酯羟烷酯和聚丙烯醇单羟酯;再优选下列的一种或多种:含羟基的丙烯酸和甲基丙烯酸的衍生物、3-羟丙酯、2-羟丙酯、羟丁酯和聚乙烯醇单羟酯;还优选含羟基的丙烯酸和甲基丙烯酸的衍生物;和最优选甲基丙烯酸羟丙酯。
3.如权利要求1或2所述的粘合剂,其特征在于,所述含羟基的丙烯酸酯的量为30重量%-50重量%,以所述组分b、c、f和g的重量之和为100重量%计。
4.如权利要求1-3任一项所述的粘合剂,其特征在于,所述氧化还原催化剂是下列的一种或多种:过氧化苯甲酰、过氧化苯甲酸叔丁酯、过氧化甲乙酮和过氧化二异丙苯。
5.如权利要求1-4任一项所述的粘合剂,其特征在于,所述硅烷偶联剂符合通式XSi(OR4)3,其中X是下列的一种或多种:乙烯基、γ-甲基丙烯酰氧基丙基和γ-异氰酸基丙基;R4是下列的一种或多种:甲基和乙基。
6.如权利要求1-5任一项所述的粘合剂,其特征在于,所述硅烷偶联剂的量为0.5重量%-1.5重量%,以所述粘合剂的量为100重量%计。
7.如权利要求1-6任一项所述的粘合剂,其特征在于,所述环氧改性的聚醚多元醇和可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇的重量之和与多异氰酸酯的重量比为0.4-1.2,最优选0.45-1.15。
8.如权利要求1-7任一项所述的粘合剂的制备方法,包含以下步骤:以任意方式混合所述异氰酸酯官能度不小于2的多异氰酸酯(a)、环氧改性的聚醚多元醇(b)、含羟基的丙烯酸酯(c)、氧化还原催化剂(d)、硅烷偶联剂(e)、可选的一含双酚A结构的多元醇(f)和可选的一不同于所述环氧改性的聚醚多元醇的聚合物多元醇(g)得到所述粘合剂;
其中所述含羟基的丙烯酸酯符合以下通式:
其中R1为氢或甲基或–CH2-OH,和R2为饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团,其中所述饱和或不饱和的、线性或支化的、脂族或脂环族的、具有至多18个碳原子的二价基团可以任选地包含氧原子和/或羟基基团;
和其中所述氧化还原催化剂为下列的一种或多种:过氧化物、过硫化物、过氧化碳酸酯、过氧化硼酸和叠氮化合物;
所述环氧改性的聚醚多元醇的量是50重量%-70重量%,和所述含羟基的丙烯酸酯的量为25重量%-50重量%,以所述组分b、c、f和g的重量之和为100重量%计。
9.根据权利要求1-7任一项所述的粘合剂用于粘接玻璃纤维复合材料的用途。
10.根据权利要求1-7任一项所述的粘合剂用于制备粘接制品的用途。
11.一种包含根据权利要求1-7任一项所述的粘合剂的粘接制品。
12.制造粘接制品的方法,包含以下步骤:
i. 将根据权利要求1-7任一项所述的粘合剂注入所需粘结部件的腔体中或涂覆到所需粘结的基材上;和
ii. 加热和固化所述粘合剂得到所述粘接制品。
13.如权利要求12所述的方法,其特征在于,所述所需粘结部件的腔体或所需粘结的基材是玻璃纤维复合材料构成的。
14.如权利要求12或13所述的方法,其特征在于,所述粘接制品是风机叶片或枕木。
15.如权利要求12-14任一项所述的方法,其特征在于,所述粘合剂加热和固化后的厚度是5mm-20mm。
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CN115595112A (zh) * | 2022-12-12 | 2023-01-13 | 万华化学集团股份有限公司(Cn) | 聚氨酯胶黏剂、无醛添加模压托盘及其制备方法 |
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CN117186833B (zh) * | 2023-09-25 | 2024-03-15 | 佛山市金德利粘胶有限公司 | 一种快速固化型硅酮胶及其制备方法 |
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